Show legend Show as text

Structure type: oligomer
C₅₃H₈₆O₂₂
Trivial name: Kizutasaponin, pericarpsaponin PJ3
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 9829
  Hattori M, Kawata Y, Kakiuchi N, Matsuura K, Tomimori T, Namba T "Application of liquid chromatography/mass spectrometry to the qualitative analysis of saponins. II" - Chemical and Pharmaceutical Bulletin 36(11) (1988) 4467-4473
  

  Qualitative analysis of crude saponin fractions from Panax ginseng, Panax japonicus and Bupleurum falcatum, as well as authentic saponins, was performed with a new type of liquid chromatography/mass spectrometry(LC/MS)system equipped with a frit-fast atom bombardment (FRIT-FAB) interface. The separation of saponins was achieved on a semi-micro column by gradient high performance liquid chromatography using an acetonitrile and water system as a mobile phase, and the elution profile was monitored by fast atom bombardment mass spectrometry (FAB-MS). The peaks were readily identified from their retention times and negative ion FAB spectra. Thus, LC/MS in the gradient-elution mode was demonstrated to be useful for qualitative analysis of saponins in crude drugs.

  ginsenoside, saikosaponin, chikusetsusaponin, LC/MS

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003654710
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Research Institute for Wakan-Yaku, Toyama Medical and Pharmaceutical University, Toyama, Japan, Scientific Instrument Division, JEOL Ltd., Tokyo, Japan, School of Pharmacy, Hokuriku University, Kanazawa, Japan
  Methods: HPLC, LC-MS
  
   
  
  Hedera rhombea
  CSDB ID 119510 (all data & tools)
• Article ID: 10379
  Higuchi R, Kawasaki T "Pericarp saponins of Akebia quinata Decne. I. Glycosides of hederagenin and oleanolic acid" - Chemical and Pharmaceutical Bulletin 24(5) (1976) 1021-1032
  

  Two free triterpenoids and twelve triterpenoid saponins were isolated from the fresh pericarps of Akebia quinata DECNE. (Lardizabalaceae). Ten saponins, P_, P_, P_ and P_K, of the above twelve were characterized as follows : P_A (I), hederagenin (hederag.) 3-O-α-L-ara・pyranoside ; P_F (II), hederag. 3-O-β-D-glc・pyr-(1→2)-α-L-ara・pyranoside ; P_B (III), oleanolic acid (ol. acid) 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; Pc (VI), hederag. 3-O-β-D-xyl・pyr-(1→3)-α-L-ara・pyranoside ; P_D (IX), hederag. 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; P_E (XI), ol, acid 3-O-β-D-glc・pyr-(1→2)-α-L-ara・pyranoside ; P_G (XIII), hederag. 3-O-β-D-xyl・pyr-(1→3)-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; P_ (XV') 3-O-α-L-ara・pyranosyl-hederag. 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside ; P_ (XIX'), 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranosyl-ol. acid 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside ; P_K (XXI), 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranosyl-hederag. 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside. VI, XI and XV'are new members of the group of hederagenin and oleanolic acid oligoglycosides. It is noted that they all have the common unit, 3-O-α-L-ara・pyranoside, and that XV', XIX'and XX, having the same trisaccharide combined with the 28-carboxyl group of the aglycone, are corresponding to I, III and IX, respectively.

  Publication DOI: 10.1248/cpb.24.1021
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003635083
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  Methods: 1H NMR, IR, acid hydrolysis, GLC, MS, methanolysis, permethylation, reduction
  
   
  
  Akebia quinata
  CSDB ID 118917 (all data & tools)
• Article ID: 10698
  Sano K, Sanada S, Ida Y, Shoji J "Studies on the constituents of the bark of Kalopanax pictus Nakai" - Chemical and Pharmaceutical Bulletin 39(4) (1991) 865-870
  

  Five new compounds, kalopanaxsaponin G (2) and kalopanaxins A (6), B (8), C (11) and D (13), were isolated from the bark of Kalopanax pictus together with nine known compounds, kalopanaxsaponins A (1) and B (5), pericarpsaponin P_ (3), hederasaponin B (4), syringin (7), protocatechuic acid (9), coniferin (10), liriodendrin (=dl-syringaresinol di-O-glucopyranoside) (12), glucosyringic acid (14) and chlorogenic acid (15). The structures of the new compounds were characterized as hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-glucopyranosyl(1→6)-β-D-glucopyranoside (2), ferulyldehyde (=coniferylaldehyde) 4-O-β-D-glucopyranoside (6), coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate (8), 2-methoxyhydroquinone 4-O-[6-O-(4-O-α-L-rhamnopyranosyl)-syringyl]-β-D-glucopyranoside (11) and coniferyl alcohol 4-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (=coniferin 2'-O-β-D-apiofuranoside) (13).

  glycoside, hederagenin, triterpenoid, araliaceae, oleanolic acid, saponin, Kalopanax pictus, phenylpropanoid, kalopanaxin, phenolic compound

  Publication DOI: 10.1248/cpb.39.865
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Showa University, Hatanodai, Japan
  Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, MS, methanolysis, alkaline hydrolysis, enzymatic digestion, CC
  
   
  
  Kalopanax pictus
  CSDB ID 119758 (all data & tools)
• Article ID: 11733
  Baykal T, Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Two oleanene glycosides from the aerial parts of Caltha polypetala" - Phytochemistry 51(8) (1999) 1059-1063
  

  Two new oleanene glycosides (1-2) possessing hederagenin as the aglycone were isolated from the methanolic extract of the aerial parts of Caltha polypetala together with four known glycosides. The saccharide portion linked to C-3 of the aglycone is made up of α-L-arabinopyranose, α-L-rhamnopyranose and galactopyranose in the new compounds; while compound 1 possesses linked to C-28 a trisaccharide moiety made up of two β-D-glucopyranose and one α-L-rhamnopyranose unit, in compound 2 the 28-COOH group is free. The structures were elucidated by 1D and 2D NMR experiments including 1H-1H (DQF-COSY, 1D-TOCSY, 2D-ROESY) and 1H-13C (HSQC, HMBC) spectroscopy.

  NMR analysis, saponins, Ranunculaceae, Caltha polypetala

  NCBI PubMed ID: 10444860
  Publication DOI: 10.1016/S0031-9422(99)00164-8
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HMBC, DEPT, HSQC
  
   
  
  Caltha polypetala
  CSDB ID 62710 (all data & tools)
• Article ID: 11778
  Yakovishin LA, Grishkovets VI, Arnautov NN, Chirva VY "Triterpene glycosides of Hedera canariensis. V. Structure of glycosides from canary ivy stems" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 587-588
  

  Triterpene glycosides from leaves of canary ivy Hedera canariensis Willd, were previously isolated and characterized [1-4]. The glycosidic composition of the plant stems is reported in the present article.

  triterpene glycosides, Hedera canariensis

  Publication DOI: 10.1007/BF02323306
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, St. Petersburg, Russia, Botanical Garden, Botanical Institute, Russian Academy of Sciences, St. Petersburg, Russia
  
   
  
  Hedera canariensis, Hedera taurica
  CSDB ID 62894 (all data & tools)
• Article ID: 12201
  Grishkovets VI, Sobolev EA, Shashkov AS, Chirva VY "Triterpenoid glycosides of Fatsia japonica. II. Isolation and structure of glycosides from the leaves" - Chemistry of Natural Compounds 36 (2000) 501-505
  

  The previously known triterpenoid 3-O-α-L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ethers of the 3-O-α-L-arabinopyranoside of hederagenin, and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical methods and 13C NMR spectroscopy.

  COSY, triterpenoid glycosides, Fatsia japonica, NMR (13C, ROESY)

  Publication DOI: 10.1023/A:1002891507725
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, alkaline hydrolysis, extraction, CC, evaporation
  
   
  
  Fatsia japonica
  CSDB ID 65600 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65608 (all data & tools)
• Article ID: 12706
  Sobolev EA, Grishkovets VI, Shashkov AS, Tolkacheva NV, Chirva VY "Triterpenoid glycosides of Fatsia japonica. III. Isolation and structure of glycosides from fruit pericarp" - Chemistry of Natural Compounds 36(5) (2000) 538-539
  
  Publication DOI: 10.1023/A:1002868330015
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
  
   
  
  Fatsia japonica
  CSDB ID 67959 (all data & tools)
• Article ID: 12820
  Wegner C, Hamburger M, Kunert O, Haslinger E "Tensioactive compounds from the aquatic plant Ranunculus fluitans L. (Ranunculaceae)" - Helvetica Chimica Acta 83(7) (2000) 1454-1464
  

  In the search for the cause for the formation of persistent foam in the Rhine River below the Rhine Fall at Schaffhausen, an investigation of the tensioactive principles from the aquatic plant Ranunculus fluitans L. (Ranunculaceae) was carried out. Two new (see 1 and 2) and four known bisdesmosidic triterpene saponins (see 4 – 6) were isolated along with the two known diacylglycerol galactosides 7 and 8. The saponin structures were established by the identification of the aglycon and sugar moieties by HPLC and chiral capillary zone electrophoresis (CZE), ion-spray LC/MS and extensive 1- and 2D homo- and heteronuclear NMR spectroscopy. The structures of the new oleanane-type saponins were identified as 3-O-[β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl]-28-O-[α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]hederagenin (1) and 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl]oleanolic acid [α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl] ester (2). LC/MS Studies of tensioactive fractions revealed the presence of additional glycoglycerolipids.

  hederagenin glycoside, Ranunculus fluitans, bisdesmosidic triterpene saponins

  Publication DOI: 10.1002/1522-2675(20000705)83:7<1454::AID-HLCA1454>3.0.CO;2-7
  Journal NLM ID: 2985094R
  Publisher: Verlag Helvetica Chimica Acta
  Institutions: Institute of Pharmaceutical Chemistry, University of Graz, Graz, Austria, Institute of Pharmaceutical Biology, University of Jena, Jena, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, HPLC, extraction, CC
  
   
  
  Ranunculus fluitans
  CSDB ID 68591 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₅₉H₉₆O₂₆
Trivial name: Kizutasaponin, Kalopanax-saponin B, kalopanax-saponin B, kalopanaxsaponin B, Kizutasaponin K12, hederasaponin C
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 9829
  Hattori M, Kawata Y, Kakiuchi N, Matsuura K, Tomimori T, Namba T "Application of liquid chromatography/mass spectrometry to the qualitative analysis of saponins. II" - Chemical and Pharmaceutical Bulletin 36(11) (1988) 4467-4473
  

  Qualitative analysis of crude saponin fractions from Panax ginseng, Panax japonicus and Bupleurum falcatum, as well as authentic saponins, was performed with a new type of liquid chromatography/mass spectrometry(LC/MS)system equipped with a frit-fast atom bombardment (FRIT-FAB) interface. The separation of saponins was achieved on a semi-micro column by gradient high performance liquid chromatography using an acetonitrile and water system as a mobile phase, and the elution profile was monitored by fast atom bombardment mass spectrometry (FAB-MS). The peaks were readily identified from their retention times and negative ion FAB spectra. Thus, LC/MS in the gradient-elution mode was demonstrated to be useful for qualitative analysis of saponins in crude drugs.

  ginsenoside, saikosaponin, chikusetsusaponin, LC/MS

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003654710
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Research Institute for Wakan-Yaku, Toyama Medical and Pharmaceutical University, Toyama, Japan, Scientific Instrument Division, JEOL Ltd., Tokyo, Japan, School of Pharmacy, Hokuriku University, Kanazawa, Japan
  Methods: HPLC, LC-MS
  
   
  
  Hedera rhombea
  CSDB ID 119513 (all data & tools)
• Article ID: 9835
  Shao CJ, Kasai R, Xu JD, Tanaka O "Saponins from roots of Kalopanax septemlobus (Thunb.) Koidz., Ciqiu: structures of kalopanax-saponins C, D, E and F" - Chemical and Pharmaceutical Bulletin 37(2) (1989) 311-314
  

  Four new triterpenois saponins named kalopanax-saponins C (4), D (5), E (6) and F (7) were isolated from the roots of Kalopanax septemlobus (THUNB.) KOIDZ. together with three known saponins, kalopanax-saponins A (1) and B (2), and chikusetsusaponin IV (3). On the basis of chemical and spectral data, the structures of these new saponins were elucidated to be as follows : (4), 3-O-α-rhamnopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-α-arabinopyranosyl hederagenin 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; (5), 3-O-α-rhamno-pyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-α-arabinopyranosyl oleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; (6), 3-O-β-glucopyranosyl-(1→3)-β-glucuronopyranosyl oleanolic acid; (7), 3-O-α-arabinopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]β-glucuronopyranosyl oleanolic acid 28-O-β-glucopyranosyl ester.

  araliaceae, saponin, Kalopanax septemlobus, kalopanax-saponin, oleanolic acid glycoside, hederagenin glycoside, Chinese folk medicine, ciqiu

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003627497
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of Chemistry, Bethune University of Medical Sciences, Changchun, China, Institute of Pharmaceutical Sciences, Hiroshima University of Medicine, Hiroshima, Japan
  Methods: 13C NMR, 1H NMR, partial acid hydrolysis, GC-MS, acid hydrolysis, GLC, HPLC, melting point determination
  
   
  
  Kalopanax septemlobus
  CSDB ID 119527 (all data & tools)
• Article ID: 9941
  Saito S, Sumita S, Tamura N, Nagamura Y, Nishida K, Ito M, Ishiguro I "Saponins from the leaves of Aralia elata SEEM. (Araliaceae)" - Chemical and Pharmaceutical Bulletin 38 (1990) 411-414
  

  Eleven triterpenoidal saponins having oleanolic acid or hederagenin as the aglycone and two flavonoidal glycosides were isolated from the leaves of Aralia elata SEEM. (Araliaceae). The structures of four new saponins (1,2,3,and 4) were established to be 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-oleanolic acid 28-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L arabinopyranosyl-hederagenin, respectively, on the basis of spectroscopic and chemical evidence.

  araliaceae, bisdesmoside, oleanolic acid glycoside, hederagenin glycoside, Aralia elata, triterpenoidal saponin, monodesmoside

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/lognavi?name=nels&lang=en&type=pdf&id=ART0004135125
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Josai University:Fujita Gakuen Health University, Japan, School of Medicine:Fujita Gakuen Health University, Japan, Department of Chemistry, School of Dentistry, Meikai University:Fujita Gakuen Health University, Japan, School of Hygiene:Fujita Gakuen Health University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, HPLC, alkaline hydrolysis
  
   
  
  Aralia elata
  CSDB ID 119619 (all data & tools)
• Article ID: 10210
  Shao CJ, Kasai R, Ohtani K, Tanaka O, Kohda H "Saponins from leaves of Kalopanax pictus (THUNB) NAKAI, harigiri: structures of Kalopanax-saponins JLa and JLb" - Chemical and Pharmaceutical Bulletin 38 (1990) 1087-1089
  

  From leaves of Kalopanax pictus (THUNB) NAKAI., collected in Japan, two new saponins named kalopanax-saponins JLa (4) and JLb (5) were isolated together with three known saponins, kalopanax-saponins A (1) and B (2) and kizuta saponin K_<11> (3). On the basis of chemical and spectral data, the structures of these new saponins were concluded to be as follows : 4 : 3-O-α-arabinopyranosyl-(1→2)-α-rhamnopyranosyl hederagenin 28-O-(2-O-acetyl-α-rhamnopyranosyl)-(1→4)-(6-O-acetyl-β-glucopyranosyl)-(1→6)-β-glucopyranosyl ester; 5 : 3-O-α-arabinopyranosyl-(1→2)-α-rhamnopyranosyl hederagenin 28-O-(3-O-acetyl-α-rhamnopyranosyl)-(1→4)-(6-O-acetyl-β-glucopyranosyl)-(1→6)-β-glycopyranosyl ester.

  araliaceae, saponin, kalopanax-saponin, hederagenin glycoside, Kalopanax pictus, harigiri, acetyl-saponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003628495
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of Chemistry, Bethune University of Medical Sciences, China, Institute of Pharmaceutical Sciences, Hiroshima University, School of Medicine, Japan
  Methods: 13C NMR, 1H NMR, gel filtration, deacetylation, FAB-MS, acid hydrolysis, HPLC, alkaline hydrolysis
  
   
  
  Kalopanax pictus
  CSDB ID 119653 (all data & tools)
• Article ID: 10379
  Higuchi R, Kawasaki T "Pericarp saponins of Akebia quinata Decne. I. Glycosides of hederagenin and oleanolic acid" - Chemical and Pharmaceutical Bulletin 24(5) (1976) 1021-1032
  

  Two free triterpenoids and twelve triterpenoid saponins were isolated from the fresh pericarps of Akebia quinata DECNE. (Lardizabalaceae). Ten saponins, P_, P_, P_ and P_K, of the above twelve were characterized as follows : P_A (I), hederagenin (hederag.) 3-O-α-L-ara・pyranoside ; P_F (II), hederag. 3-O-β-D-glc・pyr-(1→2)-α-L-ara・pyranoside ; P_B (III), oleanolic acid (ol. acid) 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; Pc (VI), hederag. 3-O-β-D-xyl・pyr-(1→3)-α-L-ara・pyranoside ; P_D (IX), hederag. 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; P_E (XI), ol, acid 3-O-β-D-glc・pyr-(1→2)-α-L-ara・pyranoside ; P_G (XIII), hederag. 3-O-β-D-xyl・pyr-(1→3)-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; P_ (XV') 3-O-α-L-ara・pyranosyl-hederag. 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside ; P_ (XIX'), 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranosyl-ol. acid 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside ; P_K (XXI), 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranosyl-hederag. 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside. VI, XI and XV'are new members of the group of hederagenin and oleanolic acid oligoglycosides. It is noted that they all have the common unit, 3-O-α-L-ara・pyranoside, and that XV', XIX'and XX, having the same trisaccharide combined with the 28-carboxyl group of the aglycone, are corresponding to I, III and IX, respectively.

  Publication DOI: 10.1248/cpb.24.1021
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003635083
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  Methods: 1H NMR, IR, acid hydrolysis, GLC, MS, methanolysis, permethylation, reduction
  
   
  
  Akebia quinata
  CSDB ID 118918 (all data & tools)
• Article ID: 10513
  Saito S, Ebashi J, Sumita S, Furumoto T, Nagamura Y, Nishida K, Isiguro I "Comparison of cytoprotective effects of saponins isolated from leaves of Aralia elata SEEM. (Araliaceae) with synthesized bisdesmosides of oleanoic acid and hederagenin on carbon tetrachloride-induced hepatic injury" - Chemical and Pharmaceutical Bulletin 41 (1993) 1395-1401
  

  Glycosylations of 3-O-{2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl(1→2)-3,4-di-O-acetyl-α-L-arabinopyranosyl}-23-O-acetylhederagenin (15) with mono- (16), di- (17) and trisaccharide bromide (18) gave the bisdesmoside peracetates 19,20 and 22,respectively, which were treated with 5% KOH in MeOH to give the bisdesmosides 25-27. Hydrolysis of the glycosides 6 and 9 having β-D-glucopyranose as a terminal sugar component with β-glucosidase in acetate buffer (pH 4.7) gave compounds 28 and 29,respectively. Cytoprotective effects of the synthesized triterpenoidal saponins against CCl_4-induced hepatic injury were compared with those of saponins isolated from the leaves of Aralia elata SEEM. (Araliaceae) using isolated hepatocytes from rat liver. Although the monodesmosides 1-4 having neutral sugar components only at the O-3 position on the aglycones showed no cytoprotective effect, bisdesmosides having sugar components at both the O-3 and O-28 positions on the aglycones had potent effects, even when the species of the sugar components were different. The bisdesmosides 10,11,and 27 having five monosaccharides in the molecules exhibited the most potent cytoprotective effects.

  glycosylation, hederagenin, bisdesmoside, cytoprotective effect, carbon tetrachloride-induced hepatic injury, oleanoic acid

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630629
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Josai University, Japan, Shiratori Pharmaceutical Co., Ltd., Japan, School of Hygiene, Fujita Health University, Japan, School of Medicine, Fujita Health University, Japan
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, enzymatic digestion, biological assay
  
   
  
  Aralia elata
  CSDB ID 120202 (all data & tools)
• Article ID: 10698
  Sano K, Sanada S, Ida Y, Shoji J "Studies on the constituents of the bark of Kalopanax pictus Nakai" - Chemical and Pharmaceutical Bulletin 39(4) (1991) 865-870
  

  Five new compounds, kalopanaxsaponin G (2) and kalopanaxins A (6), B (8), C (11) and D (13), were isolated from the bark of Kalopanax pictus together with nine known compounds, kalopanaxsaponins A (1) and B (5), pericarpsaponin P_ (3), hederasaponin B (4), syringin (7), protocatechuic acid (9), coniferin (10), liriodendrin (=dl-syringaresinol di-O-glucopyranoside) (12), glucosyringic acid (14) and chlorogenic acid (15). The structures of the new compounds were characterized as hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-glucopyranosyl(1→6)-β-D-glucopyranoside (2), ferulyldehyde (=coniferylaldehyde) 4-O-β-D-glucopyranoside (6), coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate (8), 2-methoxyhydroquinone 4-O-[6-O-(4-O-α-L-rhamnopyranosyl)-syringyl]-β-D-glucopyranoside (11) and coniferyl alcohol 4-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (=coniferin 2'-O-β-D-apiofuranoside) (13).

  glycoside, hederagenin, triterpenoid, araliaceae, oleanolic acid, saponin, Kalopanax pictus, phenylpropanoid, kalopanaxin, phenolic compound

  Publication DOI: 10.1248/cpb.39.865
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Showa University, Hatanodai, Japan
  Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, MS, methanolysis, alkaline hydrolysis, enzymatic digestion, CC
  
   
  
  Kalopanax pictus
  CSDB ID 119760 (all data & tools)
• Article ID: 10901
  Kizu H, Shimana H, Tomimori T "Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc" - Chemical and Pharmaceutical Bulletin 43(12) (1995) 2187-2194
  

  From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'-O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K_<12>, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows : clemastanoside A, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanin A, (7S, 8R)-3-methoxy-3', 4,9,9'-tetrahydroxy-4', 7-epoxy-5', 8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.

  Ranunculaceae, lignan glycoside, Clematis stans, oleanolic acid bisdesmoside, hederagenin bisdesmoside, quercetin glycoside

  NCBI PubMed ID: 8582022
  Publication DOI: 10.1248/cpb.43.2187
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Hokuriku University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, CD, HR-FAB-MS
  
   
  
  Clematis stans
  CSDB ID 120699 (all data & tools)
• Article ID: 11492
  Park HJ, Kim DH, Choi JW, Park JH, Han YN "A potent anti-diabetic agent from Kalopanax pictus" - Archives of Pharmacal Research 21(1) (1998) 24-29
  

  To search for the anti-diabetic principle from the stem bark of Kalopanax pictus, seven kinds of chemical constituents including hederagenin glycosides and phenolic glycosides were isolated. The anti-diabetic evaluation of these isolates in the streptozotocin-induced diabetic rats exhibited that kalopanaxsaponin A has a potent anti-diabetic activity in contrast to a mild activity of hederagenin. In addition, significant hypocholesterolemic and hypolipidemic activities of kalopanaxsaponin A and hederagenin were observed. The structure-activity relationship of kalopanaxsaponin A was also investigated in the present work.

  araliaceae, anti-diabetic, Kalopnax pictus, kalopnaxsapoinin A, hedearagenin

  NCBI PubMed ID: 9875510
  Publication DOI: 10.1007/BF03216748
  Journal NLM ID: 8000036
  Publisher: Pharmaceutical Society of Korea
  Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, Department of Botanical Resources, Sangji University, Wonju, South Korea, College of Pharmacy, Kyung-Hee University, Seoul, South Korea, College of Pharmacy, Kyungsung University, Pusan, South Korea, College of Pharmacy, Pusan Universoty, Pusan, South Korea
  Methods: 13C NMR, 1H NMR, biological assays, extraction, optical rotation measurement, CC, melting point determination
  
   
  
  Kalopanax pictus
  CSDB ID 62135 (all data & tools)
• Article ID: 11733
  Baykal T, Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Two oleanene glycosides from the aerial parts of Caltha polypetala" - Phytochemistry 51(8) (1999) 1059-1063
  

  Two new oleanene glycosides (1-2) possessing hederagenin as the aglycone were isolated from the methanolic extract of the aerial parts of Caltha polypetala together with four known glycosides. The saccharide portion linked to C-3 of the aglycone is made up of α-L-arabinopyranose, α-L-rhamnopyranose and galactopyranose in the new compounds; while compound 1 possesses linked to C-28 a trisaccharide moiety made up of two β-D-glucopyranose and one α-L-rhamnopyranose unit, in compound 2 the 28-COOH group is free. The structures were elucidated by 1D and 2D NMR experiments including 1H-1H (DQF-COSY, 1D-TOCSY, 2D-ROESY) and 1H-13C (HSQC, HMBC) spectroscopy.

  NMR analysis, saponins, Ranunculaceae, Caltha polypetala

  NCBI PubMed ID: 10444860
  Publication DOI: 10.1016/S0031-9422(99)00164-8
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HMBC, DEPT, HSQC
  
   
  
  Caltha polypetala
  CSDB ID 62711 (all data & tools)
• Article ID: 11778
  Yakovishin LA, Grishkovets VI, Arnautov NN, Chirva VY "Triterpene glycosides of Hedera canariensis. V. Structure of glycosides from canary ivy stems" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 587-588
  

  Triterpene glycosides from leaves of canary ivy Hedera canariensis Willd, were previously isolated and characterized [1-4]. The glycosidic composition of the plant stems is reported in the present article.

  triterpene glycosides, Hedera canariensis

  Publication DOI: 10.1007/BF02323306
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, St. Petersburg, Russia, Botanical Garden, Botanical Institute, Russian Academy of Sciences, St. Petersburg, Russia
  
   
  
  Hedera canariensis, Hedera taurica
  CSDB ID 62896 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65611 (all data & tools)
• Article ID: 12609
  Rao AV, Gurfinkel DM "The bioactivity of saponins: triterpenoid and steroidal glycosides" - Drug Metabolism and Drug Interactions 17(1-4) (2000) 211-235
  

  Triterpenoid and steroidal glycosides, referred to collectively as saponins, are bioactive compounds present naturally in many plants. They have considerable potential as pharmaceutical and/or nutraceutical agents in natural or synthetic form. Saponins, from a variety of sources, have been shown to have hypocholesterolemic, anticoagulant, anticarcinogenic, hepatoprotective, hypoglycemic, immunomodulatory, neuroprotective, anti-inflammatory and anti-oxidant activity. This paper reviews saponin research of the last decade, focussing on developments in understanding their mechanism of action and structure-activity relationships. Virtually all of this work has used animal and in vitro models. To date there are very few human data.

  immunomodulation, hypoglycemic activity, antiinflammatory activity, anti-oxidant activity, Hepatoprotection, steroidal glycosides, saponins, neuroprotection, triterpenoid glycosides, hypocholesterolemic activity, anti-coagulation, anticarcinogen

  NCBI PubMed ID: 11201296
  Publication DOI: 10.1515/dmdi.2000.17.1-4.211
  Journal NLM ID: 8904736
  Publisher: Berlin: De Gruyter
  Correspondence: v.rao@utoronto.ca
  Institutions: Department of Nutritional Sciences, University of Toronto, Toronto, Canada
  
   
  
  Kalopanax pictus
  CSDB ID 67415 (all data & tools)
• Article ID: 12662
  Press JB, Reynolds RC, May RD, Marciani DJ "Structure/function relationships of immunostimulating saponins" - Book: Studies in Natural Products Chemistry (2000) Vol. 24, Chapter E, 131-174
  

  Saponins are widely distributed plant glycosides comprising either steroidal or triterpene aglycones linked to carbohydrate chains. The triterpene saponins from Quillaja saponaria Molina, Gypsophila sp., and Saponaria officinalis, have unique immunostimulating and immunomodulating properties. Analysis of their structure/function relationships shows common structural characteristics (i.e. a triterpene aglycone containing an aldehyde group at C-4, and oligosaccharide chains attached to positions 3 and 28) that appear to account for these saponins’ effects on the immune system. The crucial role of the saponin's triterpene imine-forming carbonyl group in immune stimulating and modulating activities is supported by the following: i) saponins lacking such an aldehyde group are devoid of these activities, and ii) modification of the quillaja saponin's aldehyde group results in the loss of such activities. The oligosaccharide chains of these saponins appear to mediate targeting of saponins to antigen presenting cells (APCs), thus enhancing their immunological properties. The saponins from Quillaja saponaria Molina also contain two acyl moieties: a normonoterpene carboxylic acid and a normonoterpene carboxylic acid glycoside, which are linked linearly to a fucosyl residue attached at position C-28. These acyl groups appear to be responsible for the stimulation of cytotoxic T cells (CTLs) against exogenous antigens. Removal of the acyl moieties by mild basic hydrolysis yields deacylated quillaja saponins that are structurally and functionally comparable to the non-acylated Gypsophila sp. and Saponaria officinalis saponins; all these non-acylated saponins stimulate a poor primary immune response. Replacement of the quillaja saponin's acyl moieties with other hydrophobic groups alters their immune stimulating and modulating properties.

  plant, Immunomodulating activity, saponins

  Publication DOI: 10.1016/S1572-5995(00)80045-9
  Publisher: New York: Elsevier
  Editors: Atta-ur-Rahman
  Institutions: Galenica Pharmaceuticals, Inc., Frederick, USA, Southern Research Institute, Birmingham, USA
  
   
  
  (plant)
  CSDB ID 67771 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₁H₆₆O₁₂
Trivial name: Kalopanax-saponin A, α-hederin, kalopanaxsaponin A
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 9835
  Shao CJ, Kasai R, Xu JD, Tanaka O "Saponins from roots of Kalopanax septemlobus (Thunb.) Koidz., Ciqiu: structures of kalopanax-saponins C, D, E and F" - Chemical and Pharmaceutical Bulletin 37(2) (1989) 311-314
  

  Four new triterpenois saponins named kalopanax-saponins C (4), D (5), E (6) and F (7) were isolated from the roots of Kalopanax septemlobus (THUNB.) KOIDZ. together with three known saponins, kalopanax-saponins A (1) and B (2), and chikusetsusaponin IV (3). On the basis of chemical and spectral data, the structures of these new saponins were elucidated to be as follows : (4), 3-O-α-rhamnopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-α-arabinopyranosyl hederagenin 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; (5), 3-O-α-rhamno-pyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-α-arabinopyranosyl oleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; (6), 3-O-β-glucopyranosyl-(1→3)-β-glucuronopyranosyl oleanolic acid; (7), 3-O-α-arabinopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]β-glucuronopyranosyl oleanolic acid 28-O-β-glucopyranosyl ester.

  araliaceae, saponin, Kalopanax septemlobus, kalopanax-saponin, oleanolic acid glycoside, hederagenin glycoside, Chinese folk medicine, ciqiu

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003627497
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of Chemistry, Bethune University of Medical Sciences, Changchun, China, Institute of Pharmaceutical Sciences, Hiroshima University of Medicine, Hiroshima, Japan
  Methods: 13C NMR, 1H NMR, partial acid hydrolysis, GC-MS, acid hydrolysis, GLC, HPLC, melting point determination
  
   
  
  Kalopanax septemlobus
  CSDB ID 119526 (all data & tools)
• Article ID: 9941
  Saito S, Sumita S, Tamura N, Nagamura Y, Nishida K, Ito M, Ishiguro I "Saponins from the leaves of Aralia elata SEEM. (Araliaceae)" - Chemical and Pharmaceutical Bulletin 38 (1990) 411-414
  

  Eleven triterpenoidal saponins having oleanolic acid or hederagenin as the aglycone and two flavonoidal glycosides were isolated from the leaves of Aralia elata SEEM. (Araliaceae). The structures of four new saponins (1,2,3,and 4) were established to be 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl ester, 3-O-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-oleanolic acid 28-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl ester, 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L arabinopyranosyl-hederagenin, respectively, on the basis of spectroscopic and chemical evidence.

  araliaceae, bisdesmoside, oleanolic acid glycoside, hederagenin glycoside, Aralia elata, triterpenoidal saponin, monodesmoside

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/lognavi?name=nels&lang=en&type=pdf&id=ART0004135125
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Josai University:Fujita Gakuen Health University, Japan, School of Medicine:Fujita Gakuen Health University, Japan, Department of Chemistry, School of Dentistry, Meikai University:Fujita Gakuen Health University, Japan, School of Hygiene:Fujita Gakuen Health University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, HPLC, alkaline hydrolysis
  
   
  
  Aralia elata
  CSDB ID 119621 (all data & tools)
• Article ID: 10210
  Shao CJ, Kasai R, Ohtani K, Tanaka O, Kohda H "Saponins from leaves of Kalopanax pictus (THUNB) NAKAI, harigiri: structures of Kalopanax-saponins JLa and JLb" - Chemical and Pharmaceutical Bulletin 38 (1990) 1087-1089
  

  From leaves of Kalopanax pictus (THUNB) NAKAI., collected in Japan, two new saponins named kalopanax-saponins JLa (4) and JLb (5) were isolated together with three known saponins, kalopanax-saponins A (1) and B (2) and kizuta saponin K_<11> (3). On the basis of chemical and spectral data, the structures of these new saponins were concluded to be as follows : 4 : 3-O-α-arabinopyranosyl-(1→2)-α-rhamnopyranosyl hederagenin 28-O-(2-O-acetyl-α-rhamnopyranosyl)-(1→4)-(6-O-acetyl-β-glucopyranosyl)-(1→6)-β-glucopyranosyl ester; 5 : 3-O-α-arabinopyranosyl-(1→2)-α-rhamnopyranosyl hederagenin 28-O-(3-O-acetyl-α-rhamnopyranosyl)-(1→4)-(6-O-acetyl-β-glucopyranosyl)-(1→6)-β-glycopyranosyl ester.

  araliaceae, saponin, kalopanax-saponin, hederagenin glycoside, Kalopanax pictus, harigiri, acetyl-saponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003628495
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Department of Chemistry, Bethune University of Medical Sciences, China, Institute of Pharmaceutical Sciences, Hiroshima University, School of Medicine, Japan
  Methods: 13C NMR, 1H NMR, gel filtration, deacetylation, FAB-MS, acid hydrolysis, HPLC, alkaline hydrolysis
  
   
  
  Kalopanax pictus
  CSDB ID 119652 (all data & tools)
• Article ID: 10283
  Elias R, De Méo M, Vidal-Ollivier E, Laget M, Balansard G, Dumenil G "Antimutagenic activity of some saponins isolated from Calendula officinalis L., C. arvensis L. and Hedera helix L." - Mutagenesis 5 (1990) 327-331
  

  Thirteen saponins were isolated and identified from Calendula officinalis, C. arvensis and Hedera helix. Mutagenic and antimutagenic activities of these products were investigated using a modified liquid incubation technique of the Salmonella/microsomal assay. The Salmonella tester strain TA98 +/- S9 mix was used. Screening of the antimutagenic activity was performed with a known promutagen: benzo-[a]pyrene (BaP) and a mutagenic urine concentrate from a smoker (SU). Antimutagenic activities were also compared with the activity of chlorophyllin. All the saponins were found to be non-toxic and non-mutagenic for doses of 400 micrograms. Chlorophyllin inhibited the mutagenic activities of BaP (1 microgram) and SU (5 microliters) in a dose-dependent manner. The four saponins from C. arvensis and the three saponins from H. helix showed antimutagenic activity against BaP (1 microgram) and SU (5 microliters) with a dose-response relationship. The possible mechanism of the antimutagenic activity of saponins is discussed.

  NCBI PubMed ID: 2204784
  Journal NLM ID: 8707812
  Publisher: Oxford University Press
  Institutions: Laboratoire de Pharmacognosie, Faculté de Pharmacie, Marseille, France
  Methods: 13C NMR, 1H NMR, gel filtration, FAB-MS, biological assays
  
   
  
  Hedera helix
  CSDB ID 144147 (all data & tools)
• Article ID: 10379
  Higuchi R, Kawasaki T "Pericarp saponins of Akebia quinata Decne. I. Glycosides of hederagenin and oleanolic acid" - Chemical and Pharmaceutical Bulletin 24(5) (1976) 1021-1032
  

  Two free triterpenoids and twelve triterpenoid saponins were isolated from the fresh pericarps of Akebia quinata DECNE. (Lardizabalaceae). Ten saponins, P_, P_, P_ and P_K, of the above twelve were characterized as follows : P_A (I), hederagenin (hederag.) 3-O-α-L-ara・pyranoside ; P_F (II), hederag. 3-O-β-D-glc・pyr-(1→2)-α-L-ara・pyranoside ; P_B (III), oleanolic acid (ol. acid) 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; Pc (VI), hederag. 3-O-β-D-xyl・pyr-(1→3)-α-L-ara・pyranoside ; P_D (IX), hederag. 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; P_E (XI), ol, acid 3-O-β-D-glc・pyr-(1→2)-α-L-ara・pyranoside ; P_G (XIII), hederag. 3-O-β-D-xyl・pyr-(1→3)-α-L-rha・pyr-(1→2)-α-L-ara・pyranoside ; P_ (XV') 3-O-α-L-ara・pyranosyl-hederag. 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside ; P_ (XIX'), 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranosyl-ol. acid 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside ; P_K (XXI), 3-O-α-L-rha・pyr-(1→2)-α-L-ara・pyranosyl-hederag. 28-O-α-L-rha・pyr-(1→4)-β-D-glc・pyr-(1→6)-β-D-glc・pyranoside. VI, XI and XV'are new members of the group of hederagenin and oleanolic acid oligoglycosides. It is noted that they all have the common unit, 3-O-α-L-ara・pyranoside, and that XV', XIX'and XX, having the same trisaccharide combined with the 28-carboxyl group of the aglycone, are corresponding to I, III and IX, respectively.

  Publication DOI: 10.1248/cpb.24.1021
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003635083
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  Methods: 1H NMR, IR, acid hydrolysis, GLC, MS, methanolysis, permethylation, reduction
  
   
  
  Akebia quinata
  CSDB ID 268919 (all data & tools)
• Article ID: 10513
  Saito S, Ebashi J, Sumita S, Furumoto T, Nagamura Y, Nishida K, Isiguro I "Comparison of cytoprotective effects of saponins isolated from leaves of Aralia elata SEEM. (Araliaceae) with synthesized bisdesmosides of oleanoic acid and hederagenin on carbon tetrachloride-induced hepatic injury" - Chemical and Pharmaceutical Bulletin 41 (1993) 1395-1401
  

  Glycosylations of 3-O-{2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl(1→2)-3,4-di-O-acetyl-α-L-arabinopyranosyl}-23-O-acetylhederagenin (15) with mono- (16), di- (17) and trisaccharide bromide (18) gave the bisdesmoside peracetates 19,20 and 22,respectively, which were treated with 5% KOH in MeOH to give the bisdesmosides 25-27. Hydrolysis of the glycosides 6 and 9 having β-D-glucopyranose as a terminal sugar component with β-glucosidase in acetate buffer (pH 4.7) gave compounds 28 and 29,respectively. Cytoprotective effects of the synthesized triterpenoidal saponins against CCl_4-induced hepatic injury were compared with those of saponins isolated from the leaves of Aralia elata SEEM. (Araliaceae) using isolated hepatocytes from rat liver. Although the monodesmosides 1-4 having neutral sugar components only at the O-3 position on the aglycones showed no cytoprotective effect, bisdesmosides having sugar components at both the O-3 and O-28 positions on the aglycones had potent effects, even when the species of the sugar components were different. The bisdesmosides 10,11,and 27 having five monosaccharides in the molecules exhibited the most potent cytoprotective effects.

  glycosylation, hederagenin, bisdesmoside, cytoprotective effect, carbon tetrachloride-induced hepatic injury, oleanoic acid

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003630629
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Josai University, Japan, Shiratori Pharmaceutical Co., Ltd., Japan, School of Hygiene, Fujita Health University, Japan, School of Medicine, Fujita Health University, Japan
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, enzymatic digestion, biological assay
  
   
  
  Aralia elata
  CSDB ID 120194 (all data & tools)
• Article ID: 10526
  Danloy S, Quetin-Leclercq J, Coucke P, De Pauw-Gillet MC, Elias R, Balansard G, Angenot L, Bassleer R "Effects of α-hederin, a saponin extracted from Hedera helix, on cells cultured in vitro" - Planta Medica 60 (1994) 45-49
  

  In this work, we have analysed the effects of α-hederin, a monodesmosidic triterpenoid saponin isolated from Hedera helix, on mouse B16 melanoma cells and non-cancer mouse 3T3 fibroblasts cultured in vitro. Our results indicate that, in a serum-free medium, α-hederin is cytotoxic and inhibits proliferation in both cell lines at rather low concentrations (< 5 micrograms/ml) after only 8 hours of treatment. Its cytotoxicity decreases in the presence of serum in which BSA seems to be able to bind the saponin. α-Hederin also induces vacuolization of the cytoplasm and membrane alterations leading to cell death.

  NCBI PubMed ID: 8134416
  Publication DOI: 10.1055/s-2006-959406
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Laboratoire d'Histologie et de Cytologie, Université de Liège, Liège, Belgium
  
   
  
  Hedera helix
  CSDB ID 147291 (all data & tools)
• Article ID: 10527
  Favel A, Steinmetz MD, Regli P, Vidal-Ollivier E, Elias R, Balansard G "In vitro antifungal activity of triterpenoid saponins" - Planta Medica 60 (1994) 50-53
  

  The antifungal activity of triterpenoid saponins, with hederagenin or oleanolic acid as aglycone, was investigated in vitro by the agar dilution method. Monodesmosidic hederagenin derivatives were shown to exhibit a broad spectrum of activity against yeast as well as dermatophyte species. α-Hederin was the most active compound, and Candida glabrata was the most susceptible strain. The structure-activity relationships are discussed.

  antifungal activity, Candida glabrata, hederagenin, triterpenoid saponins, monodesmosides, dermatophytes

  NCBI PubMed ID: 8134417
  Publication DOI: 10.1055/s-2006-959407
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Laboratoire de Pharmacognosie, Faculté de Pharmacie, Marseille, France, Laboratoire de Botanique et Cryptogamie, Faculté de Pharmacie, Marseille, France
  
   
  
  Hedera helix
  CSDB ID 147295 (all data & tools)
• Article ID: 10698
  Sano K, Sanada S, Ida Y, Shoji J "Studies on the constituents of the bark of Kalopanax pictus Nakai" - Chemical and Pharmaceutical Bulletin 39(4) (1991) 865-870
  

  Five new compounds, kalopanaxsaponin G (2) and kalopanaxins A (6), B (8), C (11) and D (13), were isolated from the bark of Kalopanax pictus together with nine known compounds, kalopanaxsaponins A (1) and B (5), pericarpsaponin P_ (3), hederasaponin B (4), syringin (7), protocatechuic acid (9), coniferin (10), liriodendrin (=dl-syringaresinol di-O-glucopyranoside) (12), glucosyringic acid (14) and chlorogenic acid (15). The structures of the new compounds were characterized as hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-glucopyranosyl(1→6)-β-D-glucopyranoside (2), ferulyldehyde (=coniferylaldehyde) 4-O-β-D-glucopyranoside (6), coniferin 6'-O-(4-O-α-L-rhamnopyranosyl)-syringate (8), 2-methoxyhydroquinone 4-O-[6-O-(4-O-α-L-rhamnopyranosyl)-syringyl]-β-D-glucopyranoside (11) and coniferyl alcohol 4-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside (=coniferin 2'-O-β-D-apiofuranoside) (13).

  glycoside, hederagenin, triterpenoid, araliaceae, oleanolic acid, saponin, Kalopanax pictus, phenylpropanoid, kalopanaxin, phenolic compound

  Publication DOI: 10.1248/cpb.39.865
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Showa University, Hatanodai, Japan
  Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, MS, methanolysis, alkaline hydrolysis, enzymatic digestion, CC
  
   
  
  Kalopanax pictus
  CSDB ID 119756 (all data & tools)
• Article ID: 11492
  Park HJ, Kim DH, Choi JW, Park JH, Han YN "A potent anti-diabetic agent from Kalopanax pictus" - Archives of Pharmacal Research 21(1) (1998) 24-29
  

  To search for the anti-diabetic principle from the stem bark of Kalopanax pictus, seven kinds of chemical constituents including hederagenin glycosides and phenolic glycosides were isolated. The anti-diabetic evaluation of these isolates in the streptozotocin-induced diabetic rats exhibited that kalopanaxsaponin A has a potent anti-diabetic activity in contrast to a mild activity of hederagenin. In addition, significant hypocholesterolemic and hypolipidemic activities of kalopanaxsaponin A and hederagenin were observed. The structure-activity relationship of kalopanaxsaponin A was also investigated in the present work.

  araliaceae, anti-diabetic, Kalopnax pictus, kalopnaxsapoinin A, hedearagenin

  NCBI PubMed ID: 9875510
  Publication DOI: 10.1007/BF03216748
  Journal NLM ID: 8000036
  Publisher: Pharmaceutical Society of Korea
  Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, Department of Botanical Resources, Sangji University, Wonju, South Korea, College of Pharmacy, Kyung-Hee University, Seoul, South Korea, College of Pharmacy, Kyungsung University, Pusan, South Korea, College of Pharmacy, Pusan Universoty, Pusan, South Korea
  Methods: 13C NMR, 1H NMR, biological assays, extraction, optical rotation measurement, CC, melting point determination
  
   
  
  Kalopanax pictus
  CSDB ID 62131 (all data & tools)
• Article ID: 11733
  Baykal T, Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Two oleanene glycosides from the aerial parts of Caltha polypetala" - Phytochemistry 51(8) (1999) 1059-1063
  

  Two new oleanene glycosides (1-2) possessing hederagenin as the aglycone were isolated from the methanolic extract of the aerial parts of Caltha polypetala together with four known glycosides. The saccharide portion linked to C-3 of the aglycone is made up of α-L-arabinopyranose, α-L-rhamnopyranose and galactopyranose in the new compounds; while compound 1 possesses linked to C-28 a trisaccharide moiety made up of two β-D-glucopyranose and one α-L-rhamnopyranose unit, in compound 2 the 28-COOH group is free. The structures were elucidated by 1D and 2D NMR experiments including 1H-1H (DQF-COSY, 1D-TOCSY, 2D-ROESY) and 1H-13C (HSQC, HMBC) spectroscopy.

  NMR analysis, saponins, Ranunculaceae, Caltha polypetala

  NCBI PubMed ID: 10444860
  Publication DOI: 10.1016/S0031-9422(99)00164-8
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HMBC, DEPT, HSQC
  
   
  
  Caltha polypetala
  CSDB ID 62709 (all data & tools)
• Article ID: 11754
  Bhandari P, Gray AI, Rastogi RP "Triterpenoid Saponins from Caltha palustris" - Planta Medica 53(1) (1987) 98-100
  

  Three triterpenoid saponins, hederagenin-3-O-α-L-arabinopyranoside, oleanolic acid-3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside and hederagenin-3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside, have been isolated from Caltha palustris (Ranunculaceae). The structures were determined by spectroscopic analysis of the acetates.

  structure elucidation, spectroscopic analysis, triterpenoid saponin, Caltha palustris

  NCBI PubMed ID: 17268975
  Publication DOI: 10.1055/s-2006-962634
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India, Department of Pharmacognosy, School of Pharmacy, Trinity College Dublin, 18 Shrewsbury Road, Dublin 4, Ireland, Phytochemistry Research Laboratories, Department of Pharmacy (Pharm. Chem.), University of Strathclyde, Glasgow G1 1XW, Scotland, UK
  Methods: 13C NMR, 1H NMR, methylation, MS, optical rotation measurement, acetylation, PC, HCl hydrolysis
  
   
  
  Caltha palustris
  CSDB ID 62787 (all data & tools)
• Article ID: 11778
  Yakovishin LA, Grishkovets VI, Arnautov NN, Chirva VY "Triterpene glycosides of Hedera canariensis. V. Structure of glycosides from canary ivy stems" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 587-588
  

  Triterpene glycosides from leaves of canary ivy Hedera canariensis Willd, were previously isolated and characterized [1-4]. The glycosidic composition of the plant stems is reported in the present article.

  triterpene glycosides, Hedera canariensis

  Publication DOI: 10.1007/BF02323306
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, St. Petersburg, Russia, Botanical Garden, Botanical Institute, Russian Academy of Sciences, St. Petersburg, Russia
  
   
  
  Hedera canariensis, Hedera taurica
  CSDB ID 62890 (all data & tools)
• Article ID: 11882
  Mimaki Y, Kuroda M, Asano T, Sashida Y "Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells" - Journal of Natural Products 62(9) (1999) 1279-1283
  

  Two new triterpene saponins (8 and 9) and seven previously reported triterpene saponins (1-7) based upon oleanolic acid or hederagenin, along with two known lignans, (+)-pinoresinol (10) and β-peltatin (11), were isolated from a saponin fraction prepared from the MeOH extract of the roots of Pulsatilla chinensis. The structures of the new saponins were determined by spectroscopic analysis, including 2D NMR spectroscopic techniques, and the results of hydrolytic cleavage. The isolated compounds and some derivatives were evaluated for their cytotoxic activity against HL-60 human leukemia cells.

  cytotoxic activity, triterpene saponin, Pulsatilla chinensis

  NCBI PubMed ID: 10514313
  Publication DOI: 10.1021/np9901837
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Mimaki Y
  Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
  Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, TLC, HPLC, optical rotation measurement, TOCSY, cytotoxicity assay, HMQC, DEPT, COSY, MTT, HR-FAB-MS, HCl hydrolysis
  
   
  
  Pulsatilla chinensis
  CSDB ID 63351 (all data & tools)
• Article ID: 12124
  Delmas F, Di Giorgio C, Elias R, Gasquet M, Azas N, Mshvildadze V, Dekanosidze G, Kemertelidze E, Timon-David P "Antileishmanial activity of three saponins isolated from ivy, α-hederin, β-hederin and hederacolchiside A1, as compared to their action on mammalian cells cultured in vitro" - Planta Medica 66(4) (2000) 343-347
  

  The in vitro antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A1, was investigated on Leishmania infantum. The assessment of possible targets (membrane integrity, membrane potential, DNA synthesis and protein content) was performed in both Leishmania promastigotes and human monocytes (THP1 cells). Results observed in Leishmania showed that the saponins exhibited a strong antiproliferative activity on all stages of development of the parasite by altering membrane integrity and potential: hederacolchiside A1 appeared to be the most active compound against both promastigotes and amastigotes. Results observed in THP1 cells demonstrated that the saponins exerted also a potent antiproliferative activity against human monocytes, by producing a significant DNA synthesis inhibition. The ratio between antileishmanial activity on amastigotes and toxicity to human cells suggested that the saponins could be considered as possible antileishmanial drugs.

  flow cytometry, saponins, antileishmanial activity, araliaceae, Hedera spec., ivy, human monocytes

  NCBI PubMed ID: 10865451
  Publication DOI: 10.1055/s-2000-8541
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: delmasf@Hotmail.com
  Institutions: Laboratoire de Parasitologie, Université de la Méditerranée, Marseille, France, Laboratoire de Pharmacognosie, Université de la Méditerranée, Marseille, France, Institute of Pharmacochemistry, Academy of Sciences of Georgia, Tbilisi, Georgia
  Methods: microscopy, flow cytometry analysis, cytotoxicity assay, staining, antileishmanial assays
  
   
  
  Hedera helix, Hedera colchica
  CSDB ID 65289 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65606 (all data & tools)
• Article ID: 12340
  Lee KT, Sohn IC, Park HJ, Kim DW, Jung GO, Park KY "Essential moiety for antimutagenic and cytotoxic activity of hederagenin monodesmosides and bisdesmosides isolated from the stem bark of Kalopanax pictus" - Planta Medica 66(4) (2000) 329-332
  

  For the elucidation of the antimutagenic and cytotoxic principles from the stem bark of Kalopanax pictus, seven isolated components of this crude drug were tested in the Ames test and the MTT test. Hederagenin and its monodesmosides, kalopanaxsaponin A and I in addition to its bisdesmosides, kalopanaxsaponin B and H, showed potent antimutagenic activities against aflatoxin B1 (AFB1). However, they had no inhibitory effects on mutagenicity induced by the direct mutagen, N-methyl-N'-nitro-N-nitrosoguanidine (MNNG). This suggested that hederagenin glycosides might effectively prevent the metabolic activation of AFB1 or scavenge the electrophilic intermediate capable of inducing mutation. Hederagenin was found to be an essential moiety for the exhibition of antimutagenicity. Moreover, hederagenin and its 3-O-glycosides were found to be cytotoxic on various tumor cell lines, P-388, L-1210, U-937, HL-60, SNU-5 and HepG2, while 3,28-di-O-glycosides of hederagenin were not cytotoxic. Hence, hederagenin and its 3-O-glycosides could be suitable for cancer treatment chemopreventive drugs.

  hederagenin, araliaceae, cytotoxic, Kalopanax pictus, kalopanaxsaponin, antimutagenic

  NCBI PubMed ID: 10865448
  Publication DOI: 10.1055/s-2000-8539
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: hjpark@chiak.sangji.ac.kr
  Institutions: Research Institute for Wakan-Yaku, Toyama Medical and Pharmaceutical University, Toyama, Japan, Department of Botanical Resources, Sangji University, Wonju, South Korea, College of Pharmacy, Kyung-Hee University, Seoul, South Korea, Department of Food and Nutrition, Pusan National University, Pusan, South Korea
  
   
  
  Kalopanax pictus
  CSDB ID 66217 (all data & tools)
• Article ID: 12506
  Mshvildadze V, Favel A, Delmas F, Elias R, Faure R, Decanosidze G, Kemertelidze E, Balansard G "Antifungal and antiprotozoal activities of saponins from Hedera colchica" - Die Pharmazie 55(4) (2000) 325-326
  

  antifungal activity, hederagenin, saponins, oleanolic acid, Hedera colchica, antiprotozoal activity

  NCBI PubMed ID: 10798254
  Journal NLM ID: 9800766
  Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
  Correspondence: Favel A
  Institutions: Laboratory of Pharmacognosy, Faculty of Pharmacy, Marseille, France, Institute of Pharmacochemistry, Academy of Sciences, Tbilisi, Georgia, Laboratory of Botany and Cryptogamy, Faculty of Pharmacy, Marseille, France, Laboratory of Parasitologie, Faculty of Pharmacy, Marseille, France, Faculty of St Jérome, Marseille, France
  Methods: biological assays
  
   
  
  Hedera colchica
  CSDB ID 66954 (all data & tools)
• Article ID: 12609
  Rao AV, Gurfinkel DM "The bioactivity of saponins: triterpenoid and steroidal glycosides" - Drug Metabolism and Drug Interactions 17(1-4) (2000) 211-235
  

  Triterpenoid and steroidal glycosides, referred to collectively as saponins, are bioactive compounds present naturally in many plants. They have considerable potential as pharmaceutical and/or nutraceutical agents in natural or synthetic form. Saponins, from a variety of sources, have been shown to have hypocholesterolemic, anticoagulant, anticarcinogenic, hepatoprotective, hypoglycemic, immunomodulatory, neuroprotective, anti-inflammatory and anti-oxidant activity. This paper reviews saponin research of the last decade, focussing on developments in understanding their mechanism of action and structure-activity relationships. Virtually all of this work has used animal and in vitro models. To date there are very few human data.

  immunomodulation, hypoglycemic activity, antiinflammatory activity, anti-oxidant activity, Hepatoprotection, steroidal glycosides, saponins, neuroprotection, triterpenoid glycosides, hypocholesterolemic activity, anti-coagulation, anticarcinogen

  NCBI PubMed ID: 11201296
  Publication DOI: 10.1515/dmdi.2000.17.1-4.211
  Journal NLM ID: 8904736
  Publisher: Berlin: De Gruyter
  Correspondence: v.rao@utoronto.ca
  Institutions: Department of Nutritional Sciences, University of Toronto, Toronto, Canada
  
   
  
  (plant)
  CSDB ID 67401 (all data & tools)
• Article ID: 12662
  Press JB, Reynolds RC, May RD, Marciani DJ "Structure/function relationships of immunostimulating saponins" - Book: Studies in Natural Products Chemistry (2000) Vol. 24, Chapter E, 131-174
  

  Saponins are widely distributed plant glycosides comprising either steroidal or triterpene aglycones linked to carbohydrate chains. The triterpene saponins from Quillaja saponaria Molina, Gypsophila sp., and Saponaria officinalis, have unique immunostimulating and immunomodulating properties. Analysis of their structure/function relationships shows common structural characteristics (i.e. a triterpene aglycone containing an aldehyde group at C-4, and oligosaccharide chains attached to positions 3 and 28) that appear to account for these saponins’ effects on the immune system. The crucial role of the saponin's triterpene imine-forming carbonyl group in immune stimulating and modulating activities is supported by the following: i) saponins lacking such an aldehyde group are devoid of these activities, and ii) modification of the quillaja saponin's aldehyde group results in the loss of such activities. The oligosaccharide chains of these saponins appear to mediate targeting of saponins to antigen presenting cells (APCs), thus enhancing their immunological properties. The saponins from Quillaja saponaria Molina also contain two acyl moieties: a normonoterpene carboxylic acid and a normonoterpene carboxylic acid glycoside, which are linked linearly to a fucosyl residue attached at position C-28. These acyl groups appear to be responsible for the stimulation of cytotoxic T cells (CTLs) against exogenous antigens. Removal of the acyl moieties by mild basic hydrolysis yields deacylated quillaja saponins that are structurally and functionally comparable to the non-acylated Gypsophila sp. and Saponaria officinalis saponins; all these non-acylated saponins stimulate a poor primary immune response. Replacement of the quillaja saponin's acyl moieties with other hydrophobic groups alters their immune stimulating and modulating properties.

  plant, Immunomodulating activity, saponins

  Publication DOI: 10.1016/S1572-5995(00)80045-9
  Publisher: New York: Elsevier
  Editors: Atta-ur-Rahman
  Institutions: Galenica Pharmaceuticals, Inc., Frederick, USA, Southern Research Institute, Birmingham, USA
  
   
  
  (plant)
  CSDB ID 67772 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: sieboldianoside A
Compound class: saponin glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10471
  Sawada H, Miyakoshi M, Isoda S, Ida Y, Shoji J "Saponins from leaves of Acanthopanax sieboldianus" - Phytochemistry 34 (1993) 1117-1121
  

  Two new triterpenoid saponins named sieboldianoside A and B were isolated from the leaves of Acanthopanax sieboldianus together with five known triterpenoid saponins, kalopanax-saponins A and B, saponin A, CP3, sapindoside B, and a known flavonol glycoside, kaempferol 3-O-rutinoside. On the basis of chemical and spectral evidence, the structures of the new saponins (sieboldianoside A and B) were concluded to be α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)- β-D-glucopyranosyl esters of hederagenin and oleanolic acid 3-O-β-D- xylopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosides, respectively.

  NCBI PubMed ID: 7764238
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 146123 (all data & tools)
• Article ID: 11492
  Park HJ, Kim DH, Choi JW, Park JH, Han YN "A potent anti-diabetic agent from Kalopanax pictus" - Archives of Pharmacal Research 21(1) (1998) 24-29
  

  To search for the anti-diabetic principle from the stem bark of Kalopanax pictus, seven kinds of chemical constituents including hederagenin glycosides and phenolic glycosides were isolated. The anti-diabetic evaluation of these isolates in the streptozotocin-induced diabetic rats exhibited that kalopanaxsaponin A has a potent anti-diabetic activity in contrast to a mild activity of hederagenin. In addition, significant hypocholesterolemic and hypolipidemic activities of kalopanaxsaponin A and hederagenin were observed. The structure-activity relationship of kalopanaxsaponin A was also investigated in the present work.

  araliaceae, anti-diabetic, Kalopnax pictus, kalopnaxsapoinin A, hedearagenin

  NCBI PubMed ID: 9875510
  Publication DOI: 10.1007/BF03216748
  Journal NLM ID: 8000036
  Publisher: Pharmaceutical Society of Korea
  Institutions: Natural Products Research Institute, Seoul National University, Seoul, South Korea, Department of Botanical Resources, Sangji University, Wonju, South Korea, College of Pharmacy, Kyung-Hee University, Seoul, South Korea, College of Pharmacy, Kyungsung University, Pusan, South Korea, College of Pharmacy, Pusan Universoty, Pusan, South Korea
  Methods: 13C NMR, 1H NMR, biological assays, extraction, optical rotation measurement, CC, melting point determination
  
   
  
  Kalopanax pictus
  CSDB ID 62136 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: sieboldianoside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10471
  Sawada H, Miyakoshi M, Isoda S, Ida Y, Shoji J "Saponins from leaves of Acanthopanax sieboldianus" - Phytochemistry 34 (1993) 1117-1121
  

  Two new triterpenoid saponins named sieboldianoside A and B were isolated from the leaves of Acanthopanax sieboldianus together with five known triterpenoid saponins, kalopanax-saponins A and B, saponin A, CP3, sapindoside B, and a known flavonol glycoside, kaempferol 3-O-rutinoside. On the basis of chemical and spectral evidence, the structures of the new saponins (sieboldianoside A and B) were concluded to be α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)- β-D-glucopyranosyl esters of hederagenin and oleanolic acid 3-O-β-D- xylopyranosyl(1→3)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosides, respectively.

  NCBI PubMed ID: 7764238
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 146124 (all data & tools)
• Article ID: 10901
  Kizu H, Shimana H, Tomimori T "Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc" - Chemical and Pharmaceutical Bulletin 43(12) (1995) 2187-2194
  

  From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'-O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K_<12>, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, rutin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows : clemastanoside A, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanin A, (7S, 8R)-3-methoxy-3', 4,9,9'-tetrahydroxy-4', 7-epoxy-5', 8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.

  Ranunculaceae, lignan glycoside, Clematis stans, oleanolic acid bisdesmoside, hederagenin bisdesmoside, quercetin glycoside

  NCBI PubMed ID: 8582022
  Publication DOI: 10.1248/cpb.43.2187
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Hokuriku University, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, CD, HR-FAB-MS
  
   
  
  Clematis stans
  CSDB ID 120700 (all data & tools)

Show legend Show as text

Structure type: monomer
C₃₅H₅₆O₈
Trivial name: akeboside Stb, leontoside A, PA (seed saponin A), β2-fatsin, fatsiaside B1, koelreuteria saponin A, δ-hederin
Compound class: saponin glycoside, glycoside, triterpenoid glycoside

• Article ID: 10880
  Joshi BS, Moore KM, Pelletier SW, Puar MS, Pramanik BN "Saponins from Collinsonia canadensis" - Journal of Natural Products 55 (1992) 1468-1476
  

  Akeboside Stb, [1] and two new saponins named collinsonin and collinsonidin were isolated from the roots of Collinsonia canadensis. On the basis of chemical and spectral studies, the structure of collinsonin [2] has been established as 3-O-a-L-arabinopyranosylcollinsogenin. 16α-Hydroxyhederagenin, obtained by the hydrolysis of 2, is a new sapogenin named collinsogenin [5]. Collinsonidin [6] has been identified as 3-O-b-D-glucopyranosyl=(1''→3')-a-L-arabinopyranosylhederagenin.

  Publication DOI: 10.1021/np50088a013
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Institutions: Institute of Natural Products Research and Department of Chemistry, The University of Georgia, Athens, Georgia, USA, Schering-Plough Research Center, Bloomfield, New Jersey, USA
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, VLC
  
   
  
  Collinsonia canadensis
  CSDB ID 140791 (all data & tools)
• Article ID: 11733
  Baykal T, Bedir E, Calis I, Aquino R, Piacente S, Pizza C "Two oleanene glycosides from the aerial parts of Caltha polypetala" - Phytochemistry 51(8) (1999) 1059-1063
  

  Two new oleanene glycosides (1-2) possessing hederagenin as the aglycone were isolated from the methanolic extract of the aerial parts of Caltha polypetala together with four known glycosides. The saccharide portion linked to C-3 of the aglycone is made up of α-L-arabinopyranose, α-L-rhamnopyranose and galactopyranose in the new compounds; while compound 1 possesses linked to C-28 a trisaccharide moiety made up of two β-D-glucopyranose and one α-L-rhamnopyranose unit, in compound 2 the 28-COOH group is free. The structures were elucidated by 1D and 2D NMR experiments including 1H-1H (DQF-COSY, 1D-TOCSY, 2D-ROESY) and 1H-13C (HSQC, HMBC) spectroscopy.

  NMR analysis, saponins, Ranunculaceae, Caltha polypetala

  NCBI PubMed ID: 10444860
  Publication DOI: 10.1016/S0031-9422(99)00164-8
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Calis I
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, 84084 Penta di Fisciano, Salerno, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, optical rotation measurement, ROESY, TOCSY, DQF-COSY, HMBC, DEPT, HSQC
  
   
  
  Caltha polypetala
  CSDB ID 62708 (all data & tools)
• Article ID: 11754
  Bhandari P, Gray AI, Rastogi RP "Triterpenoid Saponins from Caltha palustris" - Planta Medica 53(1) (1987) 98-100
  

  Three triterpenoid saponins, hederagenin-3-O-α-L-arabinopyranoside, oleanolic acid-3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside and hederagenin-3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside, have been isolated from Caltha palustris (Ranunculaceae). The structures were determined by spectroscopic analysis of the acetates.

  structure elucidation, spectroscopic analysis, triterpenoid saponin, Caltha palustris

  NCBI PubMed ID: 17268975
  Publication DOI: 10.1055/s-2006-962634
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Institutions: Medicinal Chemistry Division, Central Drug Research Institute, Lucknow, India, Department of Pharmacognosy, School of Pharmacy, Trinity College Dublin, 18 Shrewsbury Road, Dublin 4, Ireland, Phytochemistry Research Laboratories, Department of Pharmacy (Pharm. Chem.), University of Strathclyde, Glasgow G1 1XW, Scotland, UK
  Methods: 13C NMR, 1H NMR, methylation, MS, optical rotation measurement, acetylation, PC, HCl hydrolysis
  
   
  
  Caltha palustris
  CSDB ID 62783 (all data & tools)
• Article ID: 11778
  Yakovishin LA, Grishkovets VI, Arnautov NN, Chirva VY "Triterpene glycosides of Hedera canariensis. V. Structure of glycosides from canary ivy stems" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 587-588
  

  Triterpene glycosides from leaves of canary ivy Hedera canariensis Willd, were previously isolated and characterized [1-4]. The glycosidic composition of the plant stems is reported in the present article.

  triterpene glycosides, Hedera canariensis

  Publication DOI: 10.1007/BF02323306
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, St. Petersburg, Russia, Botanical Garden, Botanical Institute, Russian Academy of Sciences, St. Petersburg, Russia
  
   
  
  Hedera canariensis, Hedera taurica
  CSDB ID 62888 (all data & tools)
• Article ID: 12007
  Rahman A, Shahwar D, Choudhary MI, Sener B, Toker G, Baser KH "Triterpenoid saponins from Bongardia chrysogonum" - Journal of Natural Products 63(2) (2000) 251-253
  

  Two new triterpenoid saponins, 3-O-[β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl]-hederagenin (1) and 3-O-[β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl]-hederagenin 28-O-[β-L-glucopyranosyl-(1→6)-β-L-glucopyranosyl] ester (2), together with five known saponins, were isolated from an ethanolic extract of the tubers of Bongardia chrysogonum. The structures of 1 and 2 were determined on the basis of spectroscopic studies.

  NCBI PubMed ID: 10691720
  Publication DOI: 10.1021/np9801312
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Rahman A
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, International Center of Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi, Pakistan, Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, Eskisehir, Turkey
  Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, HPLC, alkaline hydrolysis, UV, extraction, optical rotation measurement, CC, evaporation, HR-FAB-MS, VLC
  
   
  
  Bongardia chrysogonum
  CSDB ID 64763 (all data & tools)
• Article ID: 12201
  Grishkovets VI, Sobolev EA, Shashkov AS, Chirva VY "Triterpenoid glycosides of Fatsia japonica. II. Isolation and structure of glycosides from the leaves" - Chemistry of Natural Compounds 36 (2000) 501-505
  

  The previously known triterpenoid 3-O-α-L-arabinopyranosides of oleanolic and echinocystic acids and hederagenin, 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, in addition to 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ethers of the 3-O-α-L-arabinopyranoside of hederagenin, and 3-O-β-D-glucopyranosyl-(1→2)-O-α-L-arabinopyranosides of oleanolic acid and hederagenin, respectively, are isolated from leaves of Fatsia japonica (Araliaceae). The structures of the glycosides are confirmed by chemical methods and 13C NMR spectroscopy.

  COSY, triterpenoid glycosides, Fatsia japonica, NMR (13C, ROESY)

  Publication DOI: 10.1023/A:1002891507725
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, alkaline hydrolysis, extraction, CC, evaporation
  
   
  
  Fatsia japonica
  CSDB ID 65597 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65603 (all data & tools)
• Article ID: 12203
  Grishkovets VI, Sobolev EA, Shashkov AS, Chirva VY "Triterpene glycosides of Fatsia japonica. I. Isolation and structure of glycosides from Fatsia japonica seeds" - Chemistry of Natural Compounds 36 (2000) 166-160
  

  The known triterpene glycosides hederagenin 3-O-α-L-arabinopyranoside, hederagenin 3-O-β-D-glucopyranoside, oleanolic acid 3-O-β-sophoroside, hederagenin 3-O-β-sophoroside, and their 28-O-β-gentiobiosyl esters, respectively, in addition to the new triterpene glycoside 3-O-β-sophorosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-gentiobiosyl hederagenin are isolated from Fatsia japonica (Araliaceae) seeds. The structures of these glycosides are established using chemical and spectral methods.

  triterpene glycosides, Fatsia japonica, 3-O-β-sophorosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-gentiobiosyl hederagenin, structure proof

  Publication DOI: 10.1007/BF02236422
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, alkaline hydrolysis, extraction, CC, evaporation
  
   
  
  Fatsia japonica
  CSDB ID 65613 (all data & tools)
• Article ID: 12506
  Mshvildadze V, Favel A, Delmas F, Elias R, Faure R, Decanosidze G, Kemertelidze E, Balansard G "Antifungal and antiprotozoal activities of saponins from Hedera colchica" - Die Pharmazie 55(4) (2000) 325-326
  

  antifungal activity, hederagenin, saponins, oleanolic acid, Hedera colchica, antiprotozoal activity

  NCBI PubMed ID: 10798254
  Journal NLM ID: 9800766
  Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
  Correspondence: Favel A
  Institutions: Laboratory of Pharmacognosy, Faculty of Pharmacy, Marseille, France, Institute of Pharmacochemistry, Academy of Sciences, Tbilisi, Georgia, Laboratory of Botany and Cryptogamy, Faculty of Pharmacy, Marseille, France, Laboratory of Parasitologie, Faculty of Pharmacy, Marseille, France, Faculty of St Jérome, Marseille, France
  Methods: biological assays
  
   
  
  Hedera colchica
  CSDB ID 66956 (all data & tools)
• Article ID: 12706
  Sobolev EA, Grishkovets VI, Shashkov AS, Tolkacheva NV, Chirva VY "Triterpenoid glycosides of Fatsia japonica. III. Isolation and structure of glycosides from fruit pericarp" - Chemistry of Natural Compounds 36(5) (2000) 538-539
  
  Publication DOI: 10.1023/A:1002868330015
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, extraction, optical rotation measurement, melting point determination, HR-FAB-MS
  
   
  
  Fatsia japonica
  CSDB ID 67956 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: β-hederin
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 11777
  Grishkovets VI "Triterpene glycosides from Tupidanthus calyptratus. I. Structure of glycosides B1, B2, F1, and F2 from leaves of hooded Tupidanthus" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 547-551
  

  Chromatographically inseparable mixtures of oleanolic and urisolic 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosides glycosides B1 and B2) and their 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl eaters (glycosides F1 and F2) arc isolated from the leaves of Tupidanthus calyptratus Hook. f. (Araliaceae). The structures of the isolated glycosides are established from chemical methods and 1H and 13C NMR spectra. Glycoside F2 is a new triterpene glycoside.

  structure elucidation, triterpene glycoside, Tupidanthus calyptratus

  Publication DOI: 10.1007/BF02323292
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, Ukraine, Simferopol' State University, St. Petersburg, Russia
  Methods: 13C NMR, 1H NMR, TLC, alkaline hydrolysis, TFA hydrolysis, sulfuric acid hydrolysis
  
   
  
  Tupidanthus calyptratus
  CSDB ID 62883 (all data & tools)
• Article ID: 11882
  Mimaki Y, Kuroda M, Asano T, Sashida Y "Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells" - Journal of Natural Products 62(9) (1999) 1279-1283
  

  Two new triterpene saponins (8 and 9) and seven previously reported triterpene saponins (1-7) based upon oleanolic acid or hederagenin, along with two known lignans, (+)-pinoresinol (10) and β-peltatin (11), were isolated from a saponin fraction prepared from the MeOH extract of the roots of Pulsatilla chinensis. The structures of the new saponins were determined by spectroscopic analysis, including 2D NMR spectroscopic techniques, and the results of hydrolytic cleavage. The isolated compounds and some derivatives were evaluated for their cytotoxic activity against HL-60 human leukemia cells.

  cytotoxic activity, triterpene saponin, Pulsatilla chinensis

  NCBI PubMed ID: 10514313
  Publication DOI: 10.1021/np9901837
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Mimaki Y
  Institutions: School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
  Methods: 13C NMR, 1H NMR, methylation, IR, FAB-MS, TLC, HPLC, optical rotation measurement, TOCSY, cytotoxicity assay, HMQC, DEPT, COSY, MTT, HR-FAB-MS, HCl hydrolysis
  
   
  
  Pulsatilla chinensis
  CSDB ID 63350 (all data & tools)
• Article ID: 12124
  Delmas F, Di Giorgio C, Elias R, Gasquet M, Azas N, Mshvildadze V, Dekanosidze G, Kemertelidze E, Timon-David P "Antileishmanial activity of three saponins isolated from ivy, α-hederin, β-hederin and hederacolchiside A1, as compared to their action on mammalian cells cultured in vitro" - Planta Medica 66(4) (2000) 343-347
  

  The in vitro antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A1, was investigated on Leishmania infantum. The assessment of possible targets (membrane integrity, membrane potential, DNA synthesis and protein content) was performed in both Leishmania promastigotes and human monocytes (THP1 cells). Results observed in Leishmania showed that the saponins exhibited a strong antiproliferative activity on all stages of development of the parasite by altering membrane integrity and potential: hederacolchiside A1 appeared to be the most active compound against both promastigotes and amastigotes. Results observed in THP1 cells demonstrated that the saponins exerted also a potent antiproliferative activity against human monocytes, by producing a significant DNA synthesis inhibition. The ratio between antileishmanial activity on amastigotes and toxicity to human cells suggested that the saponins could be considered as possible antileishmanial drugs.

  flow cytometry, saponins, antileishmanial activity, araliaceae, Hedera spec., ivy, human monocytes

  NCBI PubMed ID: 10865451
  Publication DOI: 10.1055/s-2000-8541
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: delmasf@Hotmail.com
  Institutions: Laboratoire de Parasitologie, Université de la Méditerranée, Marseille, France, Laboratoire de Pharmacognosie, Université de la Méditerranée, Marseille, France, Institute of Pharmacochemistry, Academy of Sciences of Georgia, Tbilisi, Georgia
  Methods: microscopy, flow cytometry analysis, cytotoxicity assay, staining, antileishmanial assays
  
   
  
  Hedera helix, Hedera colchica
  CSDB ID 65290 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65604 (all data & tools)
• Article ID: 12506
  Mshvildadze V, Favel A, Delmas F, Elias R, Faure R, Decanosidze G, Kemertelidze E, Balansard G "Antifungal and antiprotozoal activities of saponins from Hedera colchica" - Die Pharmazie 55(4) (2000) 325-326
  

  antifungal activity, hederagenin, saponins, oleanolic acid, Hedera colchica, antiprotozoal activity

  NCBI PubMed ID: 10798254
  Journal NLM ID: 9800766
  Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
  Correspondence: Favel A
  Institutions: Laboratory of Pharmacognosy, Faculty of Pharmacy, Marseille, France, Institute of Pharmacochemistry, Academy of Sciences, Tbilisi, Georgia, Laboratory of Botany and Cryptogamy, Faculty of Pharmacy, Marseille, France, Laboratory of Parasitologie, Faculty of Pharmacy, Marseille, France, Faculty of St Jérome, Marseille, France
  Methods: biological assays
  
   
  
  Hedera colchica
  CSDB ID 66955 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: hederasaponin B
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 11777
  Grishkovets VI "Triterpene glycosides from Tupidanthus calyptratus. I. Structure of glycosides B1, B2, F1, and F2 from leaves of hooded Tupidanthus" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 547-551
  

  Chromatographically inseparable mixtures of oleanolic and urisolic 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabinopyranosides glycosides B1 and B2) and their 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl eaters (glycosides F1 and F2) arc isolated from the leaves of Tupidanthus calyptratus Hook. f. (Araliaceae). The structures of the isolated glycosides are established from chemical methods and 1H and 13C NMR spectra. Glycoside F2 is a new triterpene glycoside.

  structure elucidation, triterpene glycoside, Tupidanthus calyptratus

  Publication DOI: 10.1007/BF02323292
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, Ukraine, Simferopol' State University, St. Petersburg, Russia
  Methods: 13C NMR, 1H NMR, TLC, alkaline hydrolysis, TFA hydrolysis, sulfuric acid hydrolysis
  
   
  
  Tupidanthus calyptratus
  CSDB ID 62885 (all data & tools)
• Article ID: 12110
  Davydov M, Krikorian AD "Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. (Araliaceae) as an adaptogen: a closer look" - Journal of Ethnopharmacology 72(3) (2000) 345-393
  

  The adaptogen concept is examined from an historical, biological, chemical, pharmacological and medical perspective using a wide variety of primary and secondary literature. The definition of an adaptogen first proposed by Soviet scientists in the late 1950s, namely that an adaptogen is any substance that exerts effects on both sick and healthy individuals by 'correcting' any dysfunction(s) without producing unwanted side effects, was used as a point of departure. We attempted to identify critically what an adaptogen supposedly does and to determine whether the word embodies in and of itself any concept(s) acceptable to western conventional (allopathic) medicine. Special attention was paid to the reported pharmacological effects of the 'adaptogen-containing plant' Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. (Araliaceae), referred to by some as 'Siberian ginseng', and to its secondary chemical composition. We conclude that so far as specific pharmacological activities are concerned there are a number of valid arguments for equating the action of so-called adaptogens with those of medicinal agents that have activities as anti-oxidants, and/or anti-cancerogenic, immunomodulatory and hypocholesteroletic as well as hypoglycemic and choleretic action. However, 'adaptogens' and 'anti-oxidants' etc. also show significant dissimilarities and these are discussed. Significantly, the classical definition of an adaptogen has much in common with views currently being invoked to describe and explain the 'placebo effect'. Nevertheless, the chemistry of the secondary compounds of Eleutherococcus isolated thus far and their pharmacological effects support our hypothesis that the reported beneficial effects of adaptogens derive from their capacity to exert protective and/or inhibitory action against free radicals. An inventory of the secondary substances contained in Eleutherococcus discloses a potential for a wide range of activities reported from work on cultured cell lines, small laboratory animals and human subjects. Much of the cited work (although not all) has been published in peer-reviewed journals. Six compounds show various levels of activity as anti-oxidants, four show anti-cancer action, three show hypocholesterolemic activity, two show immunostimulatory effects, one has choleretic activity and one has the ability to decrease/moderate insulin levels, one has activity as a radioprotectant, one shows anti-inflammatory and anti-pyretic activities and yet another has shown activity as an antibacterial agent. Some of the compounds show more than one pharmacological effect and some show similar effects although they belong to different chemical classes. Clearly, Eleutherococcus contains pharmacologically active compounds but one wishes that the term adaptogen could be dropped from the literature because it is vague and conveys no insights into the mechanism(s) of action. If a precise action can be attributed to it, then the exact term for said action should obviously be used; if not, we strongly urge that generalities be avoided. Also, comparison of Eleutherococcus with the more familiar Panax ginseng C.A. Meyer (Araliaceae), 'true ginseng' has underscored that they differ considerably chemically and pharmacologically and cannot be justifiably considered as mutually interchangeable. Accordingly, we recommend that the designation 'Siberian ginseng' be dropped and be replaced with 'Eleutherococcus'. In the case of both Eleutherococcus and true ginseng, problems inherent in herbal preparation use include inconsistencies not only in terms of indications for use, but in the nomenclature of constituent chemical compounds, standardization, dosage and product labeling. Finally, our re-examination and fresh interpretation of the literature on Eleutherococcus and comparison with true ginseng shows that the potential for a scientifically more complete and defensible exploitation of these plants will be better served by investigating and considering them in a context that consciously ignores the fact that the word ‘adaptogen’ was ever invented.

  saponins, Panax ginseng, lignans, adaptogen, adaptogenic activity, Eleutherococcus senticosus, anti-cancer agents, anti-oxidants, placebo effect, true ginseng, ‘Siberian ginseng’

  NCBI PubMed ID: 10996277
  Publication DOI: 10.1016/s0378-8741(00)00181-1
  Journal NLM ID: 7903310
  Publisher: Limerick: Elsevier Sequoia
  Correspondence: Davydov M , Krikorian AD
  Institutions: Department of Biochemistry and Cell Biology, State University of New York at Stony Brook, Stony Brook, USA
  
   
  
  Hedera helix
  CSDB ID 65224 (all data & tools)
• Article ID: 12130
  De Tommasi N, Autore G, Bellino A, Pinto A, Pizza C, Sorrentino R, Venturella P "Antiproliferative triterpene saponins from Trevesia palmata" - Journal of Natural Products 63(3) (2000) 308-314
  

  During the course of a study of plants of the family Araliaceae, antiproliferative activity was demonstrated by the crude saponin fraction of Trevesia palmata. After chromatographic purification, six new bisdesmosidic saponins (1-6), along with two known triterpenoid saponins, (7 and 8), were isolated. The structures of 1-6 were determined by (1)H-(1)H correlation spectroscopy (COSY-DQF, 1D TOCSY, 2D HOHAHA, 1D ROESY) and (1)H-(13)C (HSQC, HMBC) spectroscopy. The antiproliferative activity of compounds 1-8 and of their prosapogenins (2a-7a) prepared by alkaline hydrolysis, was evaluated using three continuous culture cell lines.

  NMR, hederagenin, saponins, oleanolic acid, echinocystic acid, Trevesia palmata

  NCBI PubMed ID: 10757708
  Publication DOI: 10.1021/np990231n
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: detommasi@unisa.it
  Institutions: Dipartimento di Scienze Farmaceutiche, Fisciano, Italy, Dipartimento di Farmacologia Sperimentale, Napoli, Italy, Dipartimento di Scienze Botaniche, Sezione Fitochimica, Palermo, Italy
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, FAB-MS, TLC, acid hydrolysis, GC, methanolysis, alkaline hydrolysis, extraction, optical rotation measurement, CC, evaporation, MTT, optical density measurement, proliferation assay, DCCC
  
   
  
  Trevesia palmata
  CSDB ID 65312 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65609 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823

• Article ID: 11778
  Yakovishin LA, Grishkovets VI, Arnautov NN, Chirva VY "Triterpene glycosides of Hedera canariensis. V. Structure of glycosides from canary ivy stems" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 587-588
  

  Triterpene glycosides from leaves of canary ivy Hedera canariensis Willd, were previously isolated and characterized [1-4]. The glycosidic composition of the plant stems is reported in the present article.

  triterpene glycosides, Hedera canariensis

  Publication DOI: 10.1007/BF02323306
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, St. Petersburg, Russia, Botanical Garden, Botanical Institute, Russian Academy of Sciences, St. Petersburg, Russia
  
   
  
  Hedera canariensis, Hedera taurica
  CSDB ID 62889 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65605 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 11778
  Yakovishin LA, Grishkovets VI, Arnautov NN, Chirva VY "Triterpene glycosides of Hedera canariensis. V. Structure of glycosides from canary ivy stems" - Khimiia Prirodnykh Soedineniĭ = Chemistry of Natural Compounds [Russian] 35(5) (1999) 587-588
  

  Triterpene glycosides from leaves of canary ivy Hedera canariensis Willd, were previously isolated and characterized [1-4]. The glycosidic composition of the plant stems is reported in the present article.

  triterpene glycosides, Hedera canariensis

  Publication DOI: 10.1007/BF02323306
  Journal NLM ID: 0151571
  Publisher: Tashkent: Izdatelstvo Fan
  Institutions: Simferopol' State University, St. Petersburg, Russia, Botanical Garden, Botanical Institute, Russian Academy of Sciences, St. Petersburg, Russia
  
   
  
  Hedera canariensis, Hedera taurica
  CSDB ID 62895 (all data & tools)
• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65610 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823

• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65607 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

• Article ID: 12202
  Grishkovets VI, Pyatygin AM, Chirva VY "Triterpene glycosides from leaves of Acanthopanax sieboldianus introduced to Ukraine and Crimea" - Chemistry of Natural Compounds 36(3) (2000) 325-326
  

  The glycoside composition of A. sieboldianus (Eleutherococcus sieboldianus) leaves collected in Kiev, L'vov, and Simferopol, Ukraine, was studied and compared with that of leaves collected from the natural habitat. Total acid hydrolysis of the leaf extract and TLC analysis of the resulting aglycones showed a large quantity of hederagenin glycosides and a small quantity of oleanolic and echinocystic acid glycosides. The chemical structures of these triterpene glycosides are presented.

  glycoside, triterpene glycoside, organic chemistry, Acanthopanax sieboldianus

  Publication DOI: 10.1007/BF02238349
  Journal NLM ID: 0047757
  Publisher: New York: Kluwer Academic/Plenum Publishers
  Institutions: V. I. Vernadskii Tavricheskii National University, Simferopol'
  Methods: 13C NMR, TLC, acid hydrolysis, extraction, CC, evaporation
  
   
  
  Acanthopanax sieboldianus
  CSDB ID 65612 (all data & tools)