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Structure type: oligomer
Trivial name: saikosaponin a, saikosaponin-a
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_142489,IEDB_146664,IEDB_149135,IEDB_983931,SB_192,SB_86

• Article ID: 9769
  Kimura Y, Ohminami H, Okuda H, Tani T, Arichi S, Hayashi T "Effects of saikosaponins on the metabolic actions of adrenaline, ACTH and insulin on the fat cells" - Chemical and Pharmaceutical Bulletin 28(6) (1980) 1788-1794
  

  Saikosaponins a and d inhibited adrenaline-induced lipolysis in fat cells isolated from epididymal adipose tissue of rats. Saikosaponins a, b1, b2, b4, c and d inhibited ACTH-induced lipolysis in the fat cells. Insulin-stimulated lipogenesis in adipose tissue was significantly reduced by saikosaponin d. Propranolol (a β-blocker) inhibited not only lipolytic actions induced by adrenaline and ACTH but also lipogenesis stimulated by insulin. In contrast to propranolol, saikosaponins b1, b2, b4 and c selectively inhibited ACTH-induced lipolysis without affecting the lipogenetic effect of insulin. The structure-activity relationship of saikosaponins is discussed.

  structure-activity relationship, saikosaponin, Bupleurum falcatum, adrenaline-induced lipolysis, ACTH-induced lipolysis, insulin-stimulated lipogenesis, fat cells

  Publication DOI: 10.1248/cpb.28.1788
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003662561
  Publisher: Pharmaceutical Society Of Japan
  Institutions: The Research Institute of Oriental Medicine, Kinki University, Japan, School of Medicine, Ehime University, Japan, Koshiro Chuji Shoten Co, Japan
  Methods: biological activity assays
  
   
  
  Bupleurum falcatum
  CSDB ID 118978 (all data & tools)
• Article ID: 9770
  Ishii H, Nakamura M, Seo S, Tori K, Tozyo T, Yoshimura Y "Isolation, characterization, and nuclear magnetic resonance spectra of new saponins from the roots of Bupleurum falcatum L" - Chemical and Pharmaceutical Bulletin 28(8) (1980) 2367-2373
  

  A systematic separation of a saponin fraction of the root of Bupleurum falcatum L. furnished seven new saponins, i.e., five monoacetylsaikosaponins (15-18,20) and saikosaponins-e (19) and -f (21), besides the known saikosaponins-a, -b2,-b4,-c, and -d. α-Spinasteryl β-D-glucoside (22) was also isolated. The structures of these new saponins were determined by means of carbon-13 nuclear magnetic resonance spectroscopy.

  13C NMR spectroscopy, Bupleurum falcatum, separation of saikosaponins, saikogenins A-G, saikosaponin-a, saikosaponin-b1, saikosaponin-b2, saikosaponin-b3, saikosaponin-b4, saikosaponin-c, saikosaponin-d, saikosaponin-e, saikosaponin-f, monoacetylsaikosaponin, α-spinasteryl β-D-glucoside, acetylation shift

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003624035
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Shionogi Research Laboratory, Shionogi and Co, Japan
  Methods: 13C NMR, 1H NMR, TLC, melting point determination, acetylation analysis
  
   
  
  Bupleurum falcatum
  CSDB ID 118985 (all data & tools)
• Article ID: 10041
  Ding J, Fujino H, Kasai R, Fujimoto N, Tanaka O, Zhou J, Matsuura H, Fuwa T "Chemical evaluation of Bupleurum species collected in Yunnan, China" - Chemical and Pharmaceutical Bulletin 34 (1986) 1158-1167
  

  Saponins were isolated from roots of Bupleurum marginatum (Zhuye-Chaihu), B. marginatum var. stenophyllum (Zezhuye-Chaihu) and B. rockii (Lijiang-Chaihu) collected in Yunnan, China, and identified. For the evaluation of these plants as a medicine, quantitative analysis of pharmacologically active saponins, saikosaponins-a (1) and -d (3), in the plants was also conducted in comparison with B. falcatum and B. chinensis.

  saikosaponin, Umbelliferae, Chinese Bupleuri radix, Saiko, Chaihu, Bupleurum marginatum, B. marginatum var. stenophyllum, Bupleurum rockii, Yunnan medicinal plant, acetylsaikosaponin

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003626207
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Kunming Institute of Botany, Academia Sinica, Kunming, China, Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Central Research Laboratories, Wakunaga Pharmaceutical Co., Ltd., Osaka, Japan
  Methods: 13C NMR, 1H NMR, gel filtration, deacetylation, MS, HPLC
  
   
  
  Bupleurum marginatum var. stenophyllum, Bupleurum marginatum, Bupleurum rockii
  CSDB ID 119365 (all data & tools)
• Article ID: 10214
  Ebata N, Nakajima K, Taguchi H, Mitsuhashi H "Isolation of new saponins from the root of Bupleurum falcatum L." - Chemical and Pharmaceutical Bulletin 38 (1990) 1432-1434
  

  Two new malonylated oleanane-type triterpene oligoglycosides, named malonylsaikosaponins a (1) and d (2), were isolated from Bupleuri Radix, the root of Bupleurum falcatum L. Their structures were elucidated on the basis of the chemical and spectroscopic studies. Quantitative analysis of various Bupleuri Radixes by HPLC suggested that these malonylsaikosaponins are genuine saponins of this crude drug.

  malonic acid, saikosaponin, Bupleurum falcatum, Umbelliferae, Bupleuri Radix, malonylsaikosaponin, oleanane-type triterpene oligoglycoside

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003628569
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Research Institute for Biology & Chemistry, Tsumura & Co., Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS
  
   
  
  Bupleurum falcatum
  CSDB ID 219683 (all data & tools)
• Article ID: 10249
  Kanazawa H, Nagata Y, Matsushima Y, Tomoda M, Takai N "Simultaneous determination of ginsenosides and saikosaponins by high- performance liquid chromatography" - Journal of Chromatography 507 (1990) 327-332
  

  Octadecyl porous glass was used as the packing for reversed-phase high-performance liquid chromatography. A mixture of ginsenosides and saikosaponins (saponins of ginseng and bupleurum root, respectively) were analysed with detection at 203 nm. A well resolved chromatogram of ginsenoside Rb1, Rc, Rb2 and Rd and saikosaponin a, b2 and c was obtained with acetonitrile-water (25.5:74.5) as the mobile phase. The whole separation was achieved in 20 min with a flow-rate of 1.5 ml/min. Calibration graphs for ginsenoside Rb1, Rc, Rb2 and Rd and saikosaponin a and c were linear up to 5 micrograms. Rapid and accurate simultaneous determinations of the saponins are possible by the described method.

  NCBI PubMed ID: 2380300
  Publication DOI: 10.1016/S0021-9673(01)84210-2
  Journal NLM ID: 0427043
  Publisher: Amsterdam: Elsevier
  Institutions: Kyoritsu College of Pharmacy, Tokyo, Japan
  Methods: HPLC
  
   
  
  Bupleurum falcatum
  CSDB ID 138923 (all data & tools)
• Article ID: 10457
  Luo S, Lin LZ, Cordell GA "Saikosaponin derivatives from Bupleurum wenchuanense" - Phytochemistry 33 (1993) 1197-1205
  

  From the roots of Bupleurum wenchuanense 14 derivatives of saikosaponin were isolated and identified as 2″-O-β-d-xylopyranosylsaikosaponin b2, 3″,6″-O,O-diacetylsaikosaponin b2, 2″-O-β-d-glucopyranosylsaikosaponin b2, saikosaponin b2, 6″-O-acetylsaikosaponin b2, saikosaponin d, 2″-O-acetylsaikosaponin d, 3″-O-acetylsaikosaponin d, 6″-O-acetylsaikosaponin d, 16-epichikusaikoside, prosaikogenin G, saikosaponin a, 2″-O-acetylsaikosaponin a and 3″-O-acetylsaikosaponin a. The first two compounds are new derivatives of saikosaponin and this is the first isolation of prosaikogenin G from a plant. Their complete 1H and 13C NMR assignments were made by using a combination of 2D NMR techniques (DQF-COSY, HOHAHA, ROESY, HETCOR, HMQC and HMBC). Some of the compounds showed cytotoxic activity against the P-388 cell line.

  cytotoxicity, Umbelliferae, Bupleurum wenchuanense, saikosaponin glucosides, 2″-O-β-d-xylopyranosylsaikosaponin b2, 3″, 6″-O, O-diacetylsaikosaponin b2, 2″-O-β-d-glucopyranosylsaikosaponin b2, saikosaponin b2, 6″-O-acetylsaikosaponin b2, saikosaponin d, 2″-O-acetylsaikosaponin d, 3″-O-acetylsaikosaponin d, 6″-O-acetylsaikosaponin d, 16-epichikusaikoside, prosaikogenin G, saikosaponin a, 2″-O-acetylsaikosaponin a, 3″-O-acetylsaikosaponin a

  NCBI PubMed ID: 7764030
  Publication DOI: 10.1016/0031-9422(93)85049-W
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL, USA
  Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, cytotoxicity assay
  
   
  
  Bupleurum wenchuanense
  CSDB ID 295994 (all data & tools)
• Article ID: 11347
  Ahn BZ, Yoon YD, Lee YH, Kim BH, Sok DE "Inhibitory effect of bupleuri radix saponins on adhesion of some solid tumor cells and relation to hemolytic action: Screening of 232 herbal drugs for anti-cell adhesion" - Planta Medica 64(3) (1998) 220-224
  

  Anti-cell adhesive activity and hemolytic action of herbal drugs were investigated. Among 232 herbal drugs tested, six showed a remarkable anti-cell adhesive activity, and the extract from the roots of Bupleurum falcatum (Umbelliferae), the semen of Psorala corylifolia (Leguminosae), and the semen of Areca cotechu (Palmae) showed an anti-cell adhesive action at non-cytotoxic concentrations. Saikosaponins-a, d and e, isolated from the roots of Bupleurum folcatum, exhibited a potent anti-cell adhesive activity and a strong hemolytic action, In a structure-activity relationship for both activities, it seems that a sugar moiety and an ether linkage between C-13 and C-28 are required for good bioactivities. In addition, saikosaponin d with a beta-hydroxy group at C-16 was more potent than saikosaponin a possessing an alpha-hydroxy group. Taken together, it is suggested that the mechanism for anti-cell adhesive activity of sakosaponin may resemble that for their hemolytic action.

  saikosaponin, Bupleurum falcatum, Umbelliferae, anti-cell adhesion, hemolysis

  NCBI PubMed ID: 9581518
  Publication DOI: 10.1055/s-2006-957413
  Journal NLM ID: 0066751
  Publisher: George Thieme
  Correspondence: Ahn BZ
  Institutions: College of Pharmacy, Chungnam National University, Taejeon, South Korea, Korea Ginseng and Tobacco Research Institute, Taejeon, South Korea
  Methods: extraction, CC, adhesive activity, hemolysis activity
  
   
  
  Bupleurum falcatum
  CSDB ID 61361 (all data & tools)
• Article ID: 11379
  Kudo K, Tachikawa E, Kashimoto T, Takahashi E "Properties of ginseng saponin inhibition of catecholamine secretion in bovine adrenal chromaffin cells" - European Journal of Pharmacology 341(2-3) (1998) 139-144
  

  To investigate the relationship between the inhibitory effects of ginseng saponins (ginsenosides) on acetylcholine-evoked secretion of catecholamines and the structures of ginsenosides, we examined the effects of ginsenoside-Rg3 and -Rh2, which are panaxadiol saponins, 20(R)- and 20(S)-ginsenoside-Rg2, which are epimers involving the hydroxyl group at C-20 of sapogenin, and other plant saponins on the acetylcholine-evoked secretion of catecholamines from cultured bovine adrenal chromaffin cells. The ginsenoside-Rg3 (1-100 microM) and -Rh2 (10-100 microM) greatly reduced the acetylcholine-evoked secretion in a concentration-dependent manner comparable to that of ginsenoside-Rg2, a panaxatriol saponin, which was the most potent inhibitor in our previous study. 20(R)- and 20(S)-ginsenoside-Rg2 (1-100 microM) similarly reduced the acetylcholine-evoked secretion. In contrast, saikosaponin-a, glycyrrhizin and the cardiac glycosides (100 nM-100 microM), digitoxin and digoxin, had no significant inhibitory effect on catecholamine secretion. Saikosaponin-c (10-100 microM), however, had an inhibitory effect, which was less than that of ginsenoside-Rg2 and -Rg3. These results strongly suggest that the inhibitory effects of ginsenosides on the acetylcholine-evoked secretion of catecholamines from bovine adrenal chromaffin cells are a unique property of ginseng. Further, the relationship between the inhibitory effects and the structures of ginsenosides is discussed.

  ginsenoside, Ginseng saponin, catecholamine, chromaffin cell, acetylcholine

  NCBI PubMed ID: 9543231
  Publication DOI: 10.1016/s0014-2999(97)01350-2
  Journal NLM ID: 1254354
  Publisher: Amsterdam: Elsevier
  Correspondence: Tachikawa E
  Institutions: Department of Pharmacology, School of Medicine, Iwate Medical UniÍersity, Morioka, Japan, Department of Medicine, School of Dentistry, Iwate Medical UniÍersity, Morioka, Japan
  Methods: biological assays
  
   
  
  Bupleurum falcatum
  CSDB ID 61498 (all data & tools)
• Article ID: 11548
  Jung D, Sung C "Production of antibody against saikosaponin a, an active component of bupleuri radix" - Archives of Pharmacal Research 21(2) (1998) 135-139
  

  High titer rabbit polyclonal antibodies (pAbs) which show a specificity for saikosaponin a (SSA), have been generated. The immunogen used was a conjugate of SSA linked through its glucose moiety to bovine serum albumin by periodate oxidation method. The antibody titers obtained from two rabbits, innoculated with the immunogen, reached a plateau after the fourth and third booster injection, respectively. The specificity of the pAbs was determined by hapten inhibition assays using several SSA-like structures. SSA competitively inhibited the binding of the rabbit anti-SSA pAbs to SSA-ovalbumin on solid phase, a coated antigen on the well. The antibodies showed high specificity to SSA, exhibiting no significant cross-reactivity with any of SSA analogues tested.

  Periodate oxidation, polyclonal antibodies, saikosaponin a, Hapten inhibition assay

  NCBI PubMed ID: 9875420
  Publication DOI: 10.1007/BF02974017
  Journal NLM ID: 8000036
  Publisher: Pharmaceutical Society of Korea
  Institutions: College of Pharmacy, Chonnam National University, Kwangju, South Korea
  Methods: 13C NMR, 1H NMR, biological assays, extraction, Hapten inhibition test
  
   
  
  Bupleurum falcatum L
  CSDB ID 63407 (all data & tools)
• Article ID: 11917
  Ono M, Yoshida A, Ito Y, Nohara T "Phenethyl alcohol glycosides and isopentenol glycoside from fruit of Bupleurum falcatum" - Phytochemistry 51(6) (1999) 819-823
  

  Investigation on the constituents of the fruit of Bupleurum falcatum L. resulted in the isolation of the three new glycosides, phenethyl alcohol 8-O-β-D-glucopyranosyl-(1→2)-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, phenethyl alcohol 8-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside and isopentenol 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside along with five known glycosides, icariside D1, icariside F2, saikosaponin a, saikosaponin c and saikosaponin d. The structures of these compounds were elucidated on the basis of interpretation of chemical and spectral data.

  triterpene glycoside, Bupleurum falcatum, Umbelliferae, Bupleuri Radix, phenethyl alcohol glycoside, isopentenol glycoside

  NCBI PubMed ID: 10389276
  Publication DOI: 10.1016/S0031-9422(99)00073-4
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: Ono M
  Institutions: Faculty of Pharmaceutical Sciences, Kumamoto University, Oe-honmachi 5-1, Kumamoto 862-0973, Japan, Research Institute of General Education, Kyushu Tokai University, Choyo 5435, Aso, Kumamoto 869-1404, Japan, School of Agriculture, Kyushu Tokai University, Choyo 5435, Aso, Kumamoto 869-1404, Japan
  Methods: 13C NMR, 1H NMR, FAB-MS, enzymatic hydrolysis, GC, HPLC, optical rotation measurement, acetylation, COSY, HR-FAB-MS, HCl hydrolysis, trimethylsilylation
  
   
  
  Bupleurum falcatum
  CSDB ID 63920 (all data & tools)
• Article ID: 12329
  Kusakari K, Yokoyama M, Inomata S "Enhanced production of saikosaponins by root culture of Bupleurum falcatum L. using two-step control of sugar concentration" - Plant Cell Reports 19(11) (2000) 1115-1120
  

  The effect of sugar concentration on the production of saikosaponins was investigated using a root culture of Bupleurum falcatum L. The formation of the lateral roots, which were induced in the presence of indolebutyric acid, was suppressed as the sugar concentration was increased. After the lateral root tips had emerged from the inoculated roots, however, high concentrations of sugar showed no inhibitory effect on the development of the lateral roots. A two-step culture, with 1% sucrose at the beginning of the culture and addition of 6% sucrose at 14 days, when lateral roots have emerged, greatly improved the productivity, affording 0.8 g/l of saikosaponin-a and -d.

  sucrose, saikosaponin, Bupleurum falcatum, Linsmaier-Skoog medium, root culture, two-step culture

  NCBI PubMed ID: 30754779
  Publication DOI: 10.1007/s002990000240
  Journal NLM ID: 9880970
  Publisher: Berlin; New York: Springer
  Correspondence: ken.kusakari@to.shiseido.co.jp
  Institutions: Shiseido Research Center, Shiseido Co., Ltd., Yokohama-shi, Japan
  
   
  
  Bupleurum falcatum
  CSDB ID 66156 (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 67402 (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
  
   
  
  Bupleurum falcatum
  CSDB ID 67788 (all data & tools)