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1. Compound ID: 22479
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b-D-Glcp-(1-4')-+
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b-D-Glcp-(1-4")-Subst
Subst = (+)-syringaresinol = SMILES COC1=CC([C@@H]2[C@@]3([H])CO[C@H](C4=CC(OC)={104}C(O)C(OC)=C4)[C@@]3([H])CO2)=CC(OC)={54}C1O |
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Structure type: oligomer
Trivial name: liriodendrin
Compound class: glycoside, lignan glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9209
Yoshizawa F, Deyama T, Takizawa N, Usmanghani K, Ahmad M "The constituents of Cictanche tubulosa (Schrenk) Hook. f. II.: Isolation and structures of a new phenylethanoid glycoside and a new neolignan glycoside" -
Chemical and Pharmaceutical Bulletin 38(7) (1990) 1927-1930
A New phenylethanoid glycoside, named tubuloside E (I), and a new neolignan glycoside, dehydrodiconiferyl alcohol γ'-O-β-D-glucopyranoside (II), were isolated from the whole plants of Cistanche tubulosa (SCHRENK)HOOK. f. (Orobanchaceae), together with dehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (III), syringalide A 3'-α-L-rhamnopyranoside (IV), isosyringalide 3'-α-L-rhamnopyranoside (V), (+)-syringaresinol O-β-D-glucopyranoside (VI), (+)-pinoresinol O-β-D-glucopyranoside (VII), liriodendrin (VIII), 6-deoxycatalpol (IX), 8-epiloganic acid (X), 20-hydroxyecdysone (XI), 8-hydroxygeraniol 1-β-D-glucopyranoside (XII) and syringin (XIII). The structure of tubuloside E (I) was established as 2-(3, 4-dihydroxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→3)-2-O-acetyl-4-O-p-coumaroyl-β-D-glucopyranoside on the basis of chemical evidence and spectral data.
13C-NMR, Cistanche tubulosa, Orobanchaceae, phenylethanoid glycoside, iridoid, tubuloside E, dehydrodiconiferyl alcohol glycoside, syringalide rhamnoside, neolignan glycoside
Publication DOI: 10.1248/cpb.38.1927Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Central Research Laboratories, Yomeishu Seizo Co., Ltd., Minowa, Japan, Department of Pharmacognosy, Faculty of Pharmacy, University of Karachi, Karachi, Pakistan
Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GC, methanolysis, HPLC, UV, enzymatic digestion, extraction, optical rotation measurement, acetylation, CD, elemental analysis, reduction, CC, melting point determination
- Article ID: 10835
Yamazaki M, Hirota K, Chiba K, Mohri T "Promotion of neuronal differentiation of PC12h cells by Natural lignans and iridoids" -
Biological and Pharmaceutical Bulletin 17 (1994) 1604-1608
We studied the effect of (+)- and (-)-syringaresinol, (+)-syringaresinol glucosides, syringin, aucubin and catalpol on neurite outgrowth of a cultured cell line of paraneuron, PC12h cells. Of these compounds, (+)-syringaresinol diglucoside and partly glucosidase-hydrolyzed aucubin were found to be the most potent in promotion of the neurite outgrowth and stimulated responses to a high concentration of KCl and to carbachol in the cells, as observed by increase of the concentration of cytosolic free calcium. It is suggested that some of these herb-derived compounds can induce neuronal differentiation in PC12h cells.
PC12 cell, iridoid, lignan, neurite outgrowth, calcium channel
NCBI PubMed ID: 7735203Publication DOI: 10.1248/bpb.17.1604Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: 2nd Division of the Research Laboratory for Development of Medicine, Hokuriku University, Ishikawa, Japan
Methods: biological assays, enzymatic digestion
- Article ID: 10848
Kobayashi H, Karasawa H, Miyase T, Fukushima S "Studies on the constituents of Cistanchis Herba. V. Isolation and structures of two new phenylpropanoid glycosides, Cistanosides E and F" -
Chemical and Pharmaceutical Bulletin 33(4) (1985) 1452-1457
Two new phenylpropanoid glycosides, named cistanosides E (III) and F (IV), were isolated from Cistanchis Herba, the whole plant of Cistanche salsa (C. A. MEY.) G. BECK (Orobanchaceae), together with two known lignan glycosides, liriodendrin (I) and (+)-syringaresinol O-β-D-glucopyranoside (II). The structures of III and IV were determined to be 2-(4-hydroxy-3-methoxyphenyl) ethyl O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranoside and α-L-rhamnopyranosyl(1→3)-O-(4-O-caffeoyl)-D-glucopyranose, respectively, on the basis of chemical and spectral data.
13C NMR, phenylpropanoid glycoside, Orobanchaceae, lignan glycoside, Cistanche salsa, Cistanchis Herba, cistanoside E, cistanoside F, liriodendrin, (+)-syringaresinol O-b-D-glucoside
Publication DOI: 10.1248/cpb.33.1452Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Shizuoka College of Pharmacy, Japan, Central Research Laboratories, Yomeishu Seizo Co., Ltd., Japan
Methods: 13C NMR, 1H NMR, IR, TLC, acid hydrolysis, GLC, methanolysis, HPLC, alkaline hydrolysis, UV, enzymatic digestion, reduction, FD-MS, acetylation analysis
- Article ID: 12372
Ito H, Nishitani E, Konoshima T, Takasaki M, Kozuka M, Yoshida T "Flavonoid and benzophenone glycosides from Coleogyne ramosissima" -
Phytochemistry 54(7) (2000) 695-700
A benzophenone glucoside and two flavonol glycosides were isolated together with 27 known polyphenols from the aerial parts of Coleogyne ramosissima, and their structures were elucidated by spectroscopic and chemical methods as iriflophenone 2-O-β-glucopyranoside, isorhamnetin 3-O-2G-rhamnopyranosylrutinoside-7-O-α-rhamnopyranoside and limocitrin 3-O-rutinoside-7-O-β-glucopyranoside, respectively.
rosaceae, Coleogyne ramosissima, iriflophenone 2-O-glucopyranoside, isorhamnetin 3-O-2G-rhamnopyranosylrutinoside-7-O-rhamnopyranoside, limocitrin 3-O-rutinoside-7-O-glucopyranoside
NCBI PubMed ID: 10975504Publication DOI: 10.1016/s0031-9422(00)00192-8Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: yoshida@pheasant.pharm.okayama-u.ac.jp
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Faculty of Pharmaceutical Sciences, Okayama University, Okayama, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, HPLC, UV, enzymatic digestion, extraction, optical rotation measurement, CC, RP-HPLC, HR-ESI-MS
- Article ID: 12397
Kamel MS, Mohamed KM, Hassanean HA, Ohtani K, Kasai R, Yamasaki K "Iridoid and megastigmane glycosides from Phlomis aurea" -
Phytochemistry 55(4) (2000) 353-357
From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin (1) and phlomurin (2), a new megastigmane glucoside phlomuroside (3) and a new benzyl alcohol glycoside having the structure benzyl alcohol-O-β-xylopyranosyl-(1→2)-β-glucopyranoside (4) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl-O-β-xylopyranosyl-(1→2)-β-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7-O-β-glucopyranoside, acacetin-7-O-β-glucopyranoside and luteolin-7-O-β-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.
Lamiaceae, Iridoids, Phlomis aurea, megastigmane, benzyl alcohol glycosides
NCBI PubMed ID: 11117884Publication DOI: 10.1016/s0031-9422(00)00331-9Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: mkamel@mailcity.com
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut, Egypt
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, extraction, optical rotation measurement, CC, MPLC, HR-FAB-MS
- Article ID: 12525
Nikaido T, Ohmoto T, Kinoshita T, Sankawa U, Nishibe S, Hisada S "Inhibition of cyclic AMP phosphodiesterase by lignans" -
Chemical and Pharmaceutical Bulletin 29(12) (1981) 3586-3592
Cyclic adenosine monophosphate (AMP) phosphodiesterase inhibitors contained in Forsythia suspensa were identified as lignans, (+)-pinoresinol (Ia) and (+)-pinoresinol-β-D-glucoside (Id), and their structure-activity relationship was investigated. In pinoresinol congeners, the configuration of the two phenyl rings is very important in relation to the activity. When both of the p-hydroxyl groups in matairesinol congeners are substituted by methyl or glucose, the activities are decreased as compared with those of the unsubstituted compounds.
inhibitors, Forsythia suspensa, lignans, cAMP phosphodiesterase, (+)-pinoresinol, (+)-pinoresinol-β-D-glucoside, (-)-matairesinol
NCBI PubMed ID: 6280885Publication DOI: 10.1248/cpb.29.3586Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, University of Tokyo, Tokyo, Japan, Faculty of Pharmaceutical Sciences, Higashi Nippon Gakuen University, Ishikari-Tobetsu, Japan, Faculty of Pharmaceutical Sciences, Toho University, Funabashi, Japan
Methods: inhibition studies, biological assays
- Article ID: 12541
Nishibe S "Bioactive phenolic compounds in traditional medicines" -
Pure and Applied Chemistry 66(10-11) (1994) 2263-2266
Bioactive phenolic compounds in traditional medicines were investigated. Arctigenin, matairesinol, trachelogenin and nortrachelogenin from Caulis Trachelospermi, mauritianin from Herba Catharanthi, plantamajoside, acteoside and plantaginin from Plantago Herb, suspensaside, forsythiaside and (+)-pinoresinol O-β-D-glucoside from Forsythia Fruit, and (+)-syringaresinol di-O-β-D-glucoside from Eleutherococcus, were respectively isolated and subjected to assays for their biological activities.
Publication DOI: 10.1351/pac199466102263Journal NLM ID: 0376514Publisher: Oxford: Blackwell Scientific Publications
Institutions: Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen-University, Ishikari-Tobetsu, Japan
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2. Compound ID: 26218
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b-D-Glcp-(1-9)-Subst
Subst = sinapic alcohol = SMILES COC1={4}C(O)C(OC)=CC(/C=C/{9}CO)=C1 |
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Structure type: monomer
Trivial name: syringin
Compound class: glycoside, phenylpropanoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10623
Calis I, Saracoglu I, Basaran AA, Sticher O "Two phenethyl alcohol glycosides from Scutellaria orientalis subsp. Pinnatifida" -
Phytochemistry 32 (1993) 1621-1623
Two new phenethyl alcohol glycosides, darendoside A and B (= deacyl martynoside) were isolated from the methanolic extract of the aerial parts of Scutellaria orientalis subsp. pinnatifida, along with four known glycosides, syringin, martynoside, leucosceptoside A and verbascoside. On the basis of chemical and spectral evidence the structures of darendoside A and B were determined as β-(4-hydroxyphenyl)ethyl O-β-D-apiofuranosyl-(1→2)-O-β-D-glucopyranoside and β-(3-hydroxy-4-methoxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranoside (= deacyl martynoside), respectively.
Labiatae, Scutellaria orientalis subsp. pinnatifida, phenethyl alcohol glycosides, darendosides A and B (= deacyl martynoside)
NCBI PubMed ID: 7682816Publication DOI: 10.1016/0031-9422(93)85194-VJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Hacettepe University, Faculty of Pharmacy, Department of Pharmacognosy, Ankara, Turkey, Swiss Federal Institute of Technology (ETH) Zurich, Department of Pharmacy,Zürich, Switzerland
Methods: 13C NMR, 1H NMR, gel filtration, IR, FAB-MS, UV, MPLC, acetylation analysis
- Article ID: 10835
Yamazaki M, Hirota K, Chiba K, Mohri T "Promotion of neuronal differentiation of PC12h cells by Natural lignans and iridoids" -
Biological and Pharmaceutical Bulletin 17 (1994) 1604-1608
We studied the effect of (+)- and (-)-syringaresinol, (+)-syringaresinol glucosides, syringin, aucubin and catalpol on neurite outgrowth of a cultured cell line of paraneuron, PC12h cells. Of these compounds, (+)-syringaresinol diglucoside and partly glucosidase-hydrolyzed aucubin were found to be the most potent in promotion of the neurite outgrowth and stimulated responses to a high concentration of KCl and to carbachol in the cells, as observed by increase of the concentration of cytosolic free calcium. It is suggested that some of these herb-derived compounds can induce neuronal differentiation in PC12h cells.
PC12 cell, iridoid, lignan, neurite outgrowth, calcium channel
NCBI PubMed ID: 7735203Publication DOI: 10.1248/bpb.17.1604Journal NLM ID: 9311984Publisher: Pharmaceutical Society of Japan
Institutions: 2nd Division of the Research Laboratory for Development of Medicine, Hokuriku University, Ishikawa, Japan
Methods: biological assays, enzymatic digestion
- 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: 10996277Publication DOI: 10.1016/s0378-8741(00)00181-1Journal NLM ID: 7903310Publisher: 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
- Article ID: 12121
Deliorman D, Calis I, Ergun F, Doğan BSU, Buharalioğlu CK, Kanzik İ "Studies on the vascular effects of the fractions and phenolic compounds isolated from Viscum album ssp. album" -
Journal of Ethnopharmacology 72(1-2) (2000) 323-329
Viscum album L. has been used in the indigenous system of medicine for treatment of various diseases such as atherosclerosis and hypertension. In the literature, phenylpropan and flavonoid derivatives were suggested to play a role in the inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE) and a correlation was proposed between the in vitro inhibition of PDE and in vivo pharmacological activity. The vascular effects of the phenolic compounds and subfractions isolated from n-butanolic fraction of V. album ssp. album were studied on noradrenaline-contracted rat aortic rings. Isolated phenolic compounds (Syringin (VA-1), Coniferin (VA-9), 5, 7-dimethoxy-flavanone-4'-O-[β-D-apiofuranosyl(1→2)]-β-D-glucopyranoside (VA-4)) produced concentration-dependent contractions in rat aortic rings. Only one compound (Kalopanaxin D (VA-15)) displayed very slight relaxant response. The weak concentration-dependent relaxing effect of the subfractions gave the idea that vasodilator activity were observed in the less polar subfractions. In addition, there was no clear correlation between the weak relaxant effects of subfractions and an inhibitory effect on cAMP-PDE.
Viscum album ssp. album, Loranthaceae, rat aorta, vascular effects, Cyclic adenosine monophosphate-phosphodiesterase
NCBI PubMed ID: 10967490Publication DOI: 10.1016/s0378-8741(00)00251-8Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Institutions: Gazi University, Faculty of Pharmacy, Ankara, Turkey, Hacettepe University, Faculty of Pharmacy, Ankara, Turkey, İstanbul University, Faculty of Pharmacy, İstanbul, Turkey
Methods: 13C NMR, 1H NMR, IR, TLC, biological assays, MS, UV, extraction, CC, evaporation, MPLC
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3. Compound ID: 26987
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b-Glcp-(1-2)-a-Arap-(1-3)-+
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a-Rhap-(1-4)-b-Glcp-(1-6)-b-Glcp-(1-28)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
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Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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4. Compound ID: 26988
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b-Glcp-(1-2)-a-Arap-(1-3)-Oleanolic
Oleanolic = 3β-hydroxyolean-12-en-28-oic acid |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_581506,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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5. Compound ID: 26989
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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6. Compound ID: 26990
|
b-Glcp-(1-2)-a-Arap-(1-3)-Subst
Subst = 30-norolean-12,20(29)-dien-3β-ol-28-oic acid = SMILES CC(C)([C@](CC[C@@]([C@](CC[C@@](CC1)2{28}C(O)=O)3C)4C)5[H]){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])CC1=C |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_581506,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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7. Compound ID: 26991
|
a-Rhap-(1-2)-a-Arap-(1-3)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_225177,IEDB_581506,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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8. Compound ID: 26992
|
a-Arap-(1-3)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_581506
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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9. Compound ID: 26993
|
b-Glcp-(1-2)-a-Arap-(1-3)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_581506,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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10. Compound ID: 26994
|
a-Arap-(1-3)-+
|
a-Rhap-(1-4)-b-Glcp-(1-6)-b-Glcp-(1-28)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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11. Compound ID: 26995
|
b-Glcp-(1-2)-a-Arap-(1-3)-+
|
a-Rhap-(1-4)-b-Glcp-(1-6)-b-Glcp-(1-28)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A1
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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12. Compound ID: 26996
|
b-Glcp-(1-2)-a-Arap-(1-3)-+
|
a-Rhap-(1-4)-b-Glcp-(1-6)-b-Glcp-(1-28)-Subst
Subst = 30-norolean-12,20(29)-dien-3β-ol-28-oic acid = SMILES CC(C)([C@](CC[C@@]([C@](CC[C@@](CC1)2{28}C(O)=O)3C)4C)5[H]){3}[C@@H](O)CC[C@]5(C)[C@@]4([H])CC=C3[C@]2([H])CC1=C |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A2
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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13. Compound ID: 26997
|
a-Rhap-(1-2)-a-Arap-(1-3)-+
|
a-Rhap-(1-4)-b-Glcp-(1-6)-b-Glcp-(1-28)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside A3
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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14. Compound ID: 26998
|
a-Arap-(1-3)-+
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a-Rhap-(1-4)-b-Glcp6Ac-(1-6)-b-Glcp-(1-28)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: ciwujianoside D3
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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15. Compound ID: 26999
|
b-Glcp-(1-2)-a-Arap-(1-3)-+
|
a-Rhap-(1-4)-b-Glcp6Ac-(1-6)-b-Glcp-(1-28)-Subst
Subst = mesembryanthemoidigenic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])C[C@](C)({29}CO)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Structure type: oligomer
Trivial name: ciwujianoside D3
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_1394181,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_581506,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10850
Shao C, Kasai R, Xu J, Tanaka O "Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia. II. Structures of Ciwujianosides A1, A2, A3, A4 and D3" -
Chemical and Pharmaceutical Bulletin 37 (1989) 42-45
Further investigation of the chemical constituents of the leaves of Acanthopanax senticosus HARMS. resulted in the isolation of five new triterpenoid saponins, named ciwujianosides A_1 (1), A_2 (2), A_3 (3), D_3(4) and A_4 (5). The structures of these saponins were elucidated as follows : 1,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyloleanolic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 2,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 3,3-O-α-rhamnopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 4,3-O-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester; 5,3-O-β-glucopyranosyl-(1→2)-α-arabinopyranosylmesembryanthemoidigenic acid 28-O-α-rhamnopyranosyl-(1→4)-6-O-acetyl-β-glucopyranosyl-(1→6)-β-glucopyranosyl ester.
araliaceae, saponin, oleanolic acid glycoside, Chinese folk medicine, Acanthopanax senticosus, ciwujianoside, noroleanolic acid glycoside, mesembryanthemoidigenic acid glycoside, ciwujia
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003627232Publisher: Pharmaceutical Society Of Japan
Institutions: Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Hiroshima, Japan, Department of Chemistry, Bethune University of Medical Sciences, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, enzymatic digestion
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