Found 149 structures.
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1. Compound ID: 19235
Structure type: monomer
; 567.1 [M-H]-
C28H23O13
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_139965,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7581
Heřmánková-Vavříková E, Křenková A, Petrásková L, Chambers CS, Zápal J, Kuzma M, Valentová K, Křen V "Synthesis and antiradical activity of isoquercitrin esters with aromatic acids and their homologues" -
International Journal of Molecular Sciences 18(5) (2017) E1074
Isoquercitrin, (IQ, quercetin-3-O-β-D-glucopyranoside) is known for strong chemoprotectant activities. Acylation of flavonoid glucosides with carboxylic acids containing an aromatic ring brings entirely new properties to these compounds. Here, we describe the chemical and enzymatic synthesis of a series of IQ derivatives at the C-6″. IQ benzoate, phenylacetate, phenylpropanoate and cinnamate were prepared from respective vinyl esters using Novozym 435 (Lipase B from Candida antarctica immobilized on acrylic resin). The enzymatic procedure gave no products with "hydroxyaromatic" acids, their vinyl esters nor with their benzyl-protected forms. A chemical protection/deprotection method using Steglich reaction yielded IQ 4-hydroxybenzoate, vanillate and gallate. In case of p-coumaric, caffeic, and ferulic acid, the deprotection lead to the saturation of the double bonds at the phenylpropanoic moiety and yielded 4-hydroxy-, 3,4-dihydroxy- and 3-methoxy-4-hydroxy-phenylpropanoates. Reducing capacity of the cinnamate, gallate and 4-hydroxyphenylpropanoate towards Folin-Ciocalteau reagent was significantly lower than that of IQ, while other derivatives displayed slightly better or comparable capacity. Compared to isoquercitrin, most derivatives were less active in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, but they showed significantly better 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) scavenging activity and were substantially more active in the inhibition of tert-butylhydroperoxide induced lipid peroxidation of rat liver microsomes. The most active compounds were the hydroxyphenylpropanoates.
Antioxidant activity, DPPH, lipase, Novozym 435, aromatic acid, cinnamic acid, gallic acid, isoquercitrin, lipoperoxidation
NCBI PubMed ID: 28513572Publication DOI: 10.3390/ijms18051074Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: kata.valentova@email.cz
Institutions: Laboratory of Biotransformation, Institute of Microbiology, Czech Academy of Sciences, Prague, Czech
Methods: 13C NMR, 1H NMR, ESI-MS, HPLC, TOCSY, HMBC, COSY, HSQC
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2. Compound ID: 19299
|
a-L-Rhap-(1-6)-b-D-Glcp4Bz-(1-9)-Subst
Subst = styron = SMILES O{9}C/C=C/c1ccccc1 |
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Structure type: oligomer
; 569.2031 [M+Na]+
C28H34O11
Trivial name: cinnamrutinose B
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_139965,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 7603
Jossang A, Jossang P, Bodo B "Cinnamrutinoses A and B, glycosides of Populus tremula" -
Phytochemistry 35(2) (1994) 547-549
The cinnamylrutinosides, cinnamrutinoses A and B, were isolated along with known phenolic glucosides, from the stem bark of Populus tremula infected with the pathogenic fungus Hypoxylon mammatum. The structures were determined from spectroscopic and chemical evidence.
Populus tremula, Salicaceae, stem bark, cinnamylglucosides, cinnamrutinose A, cinnamrutinose B
NCBI PubMed ID: 7764484Publication DOI: 10.1016/s0031-9422(00)94801-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Laboratoire de Chimie, URA 401 CNRS, Muséum National d'Histoire Naturelle, Paris, France
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, biological assays, UV, extraction, optical rotation measurement, CI-MS, column chromatography, HR-FAB-MS
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3. Compound ID: 23962
|
Tig-(1-11)-+
|
b-D-Glcp-(1-4)-b-D-6dAllp3Me-(1-4)-b-D-Olip3Me-(1-3)-Subst12Bz
Subst = tenacigenin B = SMILES O{3}[C@H]1CC[C@@]2(C)[C@](CC[C@]3(O4)[C@]2([H]){11}[C@H](O){12}[C@@H](O)[C@@]5(C)[C@]34CC[C@@]5([H])C(C)=O)([H])C1;
Tig = tiglic acid |
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Structure type: oligomer
Trivial name: tenacissoside C
Contained glycoepitopes: IEDB_139965,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9809
Miyakawa S, Yamaura K, Hayashi K, Kaneko K, Mitsuhashi H "Studies on the constituents of Asclepiadaceae plants. Part 63. Five glycosides from the Chinese drug Tong-guang-san: the stems of Marsdenia tenacissima" -
Phytochemistry 25 (1986) 2861-2865
Five new glycosides were isolated from the Chinese crude drug ‘Tong-guang-san’: the stems of Marsdenia tenacissima (Roth.) Wight et Arn. (Asclepiadaceae). The structures of tenacissosides A-E were deduced on the basis of chemical and spectral evidence as tenacigenin B-I 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D- allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-II 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy- β-Dallopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-III 3-O-β-Dglucopyranosyl-(1→4)-3-O-methyl-6- deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-IV 3-O-β-D-glucopyranosyl-(1→4)-3-O- methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside and tenacigenin B-V 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-allopyranosyl-(1→4)-β-D-oleandropyranoside, respectively.
Marsdenia tenacissima, Asclepiadaceae, pregnane glycosides, tenacissosides A-E
Publication DOI: 10.1016/S0031-9422(00)83756-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan
Methods: gel filtration, 13C NMR, 1H NMR, acid hydrolysis, HPLC, melting point determination
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4. Compound ID: 23964
|
aiVl-(1-11)-+
|
b-D-Glcp-(1-4)-b-D-6dAllp3Me-(1-4)-b-D-Olip3Me-(1-3)-Subst12Bz
Subst = tenacigenin B = SMILES O{3}[C@H]1CC[C@@]2(C)[C@](CC[C@]3(O4)[C@]2([H]){11}[C@H](O){12}[C@@H](O)[C@@]5(C)[C@]34CC[C@@]5([H])C(C)=O)([H])C1;
aiVl = anteisovaleric acid |
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Structure type: oligomer
Trivial name: tenacissoside E
Contained glycoepitopes: IEDB_139965,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9809
Miyakawa S, Yamaura K, Hayashi K, Kaneko K, Mitsuhashi H "Studies on the constituents of Asclepiadaceae plants. Part 63. Five glycosides from the Chinese drug Tong-guang-san: the stems of Marsdenia tenacissima" -
Phytochemistry 25 (1986) 2861-2865
Five new glycosides were isolated from the Chinese crude drug ‘Tong-guang-san’: the stems of Marsdenia tenacissima (Roth.) Wight et Arn. (Asclepiadaceae). The structures of tenacissosides A-E were deduced on the basis of chemical and spectral evidence as tenacigenin B-I 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D- allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-II 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy- β-Dallopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-III 3-O-β-Dglucopyranosyl-(1→4)-3-O-methyl-6- deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-IV 3-O-β-D-glucopyranosyl-(1→4)-3-O- methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside and tenacigenin B-V 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-allopyranosyl-(1→4)-β-D-oleandropyranoside, respectively.
Marsdenia tenacissima, Asclepiadaceae, pregnane glycosides, tenacissosides A-E
Publication DOI: 10.1016/S0031-9422(00)83756-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan
Methods: gel filtration, 13C NMR, 1H NMR, acid hydrolysis, HPLC, melting point determination
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5. Compound ID: 24266
|
b-D-Glcp-(1-2)-+ pCoum-(9-1)-+
| |
b-D-Glcp-(1-3)-b-D-Glcp4Ac6Ac-(1-3)-a-D-Glcp6Ac-(1-2)-b-D-Fruf3Bz
|
Fer-(9-4)-+
pCoum = p-coumaric acid;
Fer = ferulic acid;
Bz = benzoic acid |
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Structure type: oligomer
; 1381 [M+H]+
C62H76O35
Trivial name: tenuifoliose A
Contained glycoepitopes: IEDB_116879,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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6. Compound ID: 24268
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-2)-+ pCoum4Ac-(9-1)-+
| |
b-D-Glcp2Ac3Ac4Ac6Ac-(1-3)-b-D-Glcp2Ac4Ac6Ac-(1-3)-a-D-Glcp6Ac-(1-2)-b-D-Fruf3Bz4Ac6Ac
|
Fer4Ac-(9-4)-+
Bz = benzoic acid;
pCoum = p-coumaric acid;
Fer = ferulic acid |
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Structure type: oligomer
Trivial name: tenuifoliose A
Contained glycoepitopes: IEDB_116879,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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7. Compound ID: 24269
|
b-D-Glcp-(1-2)-+ pCoum-(9-1)-+
| |
b-D-Glcp-(1-3)-b-D-Glcp4Ac6Ac-(1-3)-a-D-Glcp-(1-2)-b-D-Fruf3Bz
|
Fer-(9-4)-+
Bz = benzoic acid;
pCoum = p-coumaric acid;
Fer = ferulic acid |
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Structure type: oligomer
Trivial name: tenuifoliose B
Contained glycoepitopes: IEDB_116879,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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8. Compound ID: 24270
|
b-D-Glcp-(1-2)-+ pCoum-(9-1)-+
| |
b-D-Glcp-(1-3)-b-D-Glcp6Ac-(1-3)-a-D-Glcp-(1-2)-b-D-Fruf3Bz
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Fer-(9-4)-+
Bz = benzoic acid;
pCoum = p-coumaric acid;
Fer = ferulic acid |
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Structure type: oligomer
Trivial name: tenuifoliose C
Contained glycoepitopes: IEDB_116879,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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9. Compound ID: 24271
|
b-D-Glcp-(1-2)-+ pCoum-(9-1)-+
| |
b-D-Glcp-(1-3)-b-D-Glcp6Ac-(1-3)-a-D-Glcp6Ac-(1-2)-b-D-Fruf3Bz
|
Fer-(9-4)-+
Bz = benzoic acid;
pCoum = p-coumaric acid;
Fer = ferulic acid |
Show graphically |
Structure type: oligomer
Trivial name: tenuifoliose D
Contained glycoepitopes: IEDB_116879,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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10. Compound ID: 24272
|
b-D-Glcp-(1-2)-+ pCoum-(9-1)-+
| |
b-D-Glcp-(1-3)-b-D-Glcp-(1-3)-a-D-Glcp6Ac-(1-2)-b-D-Fruf3Bz
|
Fer-(9-4)-+
Bz = benzoic acid;
pCoum = p-coumaric acid;
Fer = ferulic acid |
Show graphically |
Structure type: oligomer
Trivial name: tenuifoliose E
Contained glycoepitopes: IEDB_116879,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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11. Compound ID: 24273
|
a-Rha-(1-4)-Fer-(9-4)-+ pCoum-(9-1)-+
| |
b-D-Glcp-(1-3)-b-D-Glcp4Ac6Ac-(1-3)-a-D-Glcp6Ac-(1-2)-b-D-Fruf3Bz
|
b-D-Glcp-(1-2)-+
pCoum = p-coumaric acid;
Fer = ferulic acid;
Bz = benzoic acid |
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Structure type: oligomer
; 1549 [M+Na]+
C68H86O39
Trivial name: tenuifoliose F
Contained glycoepitopes: IEDB_116879,IEDB_136105,IEDB_1394181,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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12. Compound ID: 24274
|
a-Rha2Ac3Ac4Ac-(1-4)-Fer-(9-4)-+ pCoum4Ac-(9-1)-+
| |
b-D-Glcp2Ac3Ac4Ac6Ac-(1-3)-b-D-Glcp2Ac4Ac6Ac-(1-3)-a-D-Glcp6Ac-(1-2)-b-D-Fruf3Bz4Ac6Ac
|
b-D-Glcp2Ac3Ac4Ac6Ac-(1-2)-+
Bz = benzoic acid;
pCoum = p-coumaric acid;
Fer = ferulic acid |
Show graphically |
Structure type: oligomer
C68H86O39
Contained glycoepitopes: IEDB_116879,IEDB_130422,IEDB_136105,IEDB_1394181,IEDB_139965,IEDB_140628,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61
The structure is contained in the following publication(s):
- Article ID: 9913
Miyase T, Iwata Y, Ueno A "Tenuifolioses A-F, oligosaccharide multi-esters from the roots of Polygala tenuifolia Willd" -
Chemical and Pharmaceutical Bulletin 39 (1991) 3082-3084
From the roots of Polygala tenuifolia WILLD. six new oligosaccharides, named tenuifolioses A-F, were isolated and their structures were elucidated by spectroscopic data and chemical evidence. These oligosaccharides were esterified with acetic, benzoic, p-coumaric and ferulic acid.
oligosaccharide, acetate, Polygala tenuifolia, Polygalaceae, tenuifoliose, benzoate, p-coumarate, ferulate
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003629027Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, University of Shizuoka, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, acetylation analysis
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13. Compound ID: 24340
|
b-D-Glcp-(1-2)-+
|
b-D-Xylp4Bz-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst
Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])C{6}[C@@H](O)[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H];
Bz = benzoic acid |
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Structure type: oligomer
; 1152 [M-H2O]-
C57H86O25
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_137472,IEDB_139965,IEDB_140628,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 9942
Kawashima K, Mimaki Y, Sashida Y "Steroidal saponins from the bulbs of Allium schubertii" -
Phytochemistry 32 (1993) 1267-1272
Phytochemical examination of the fresh bulbs of Allium schubertii led to the isolation of four new steroidal saponins together with a known saponin. The structures of the new saponins were established by spectroscopic data, hydrolysis and chemical correlation as (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[3-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glu-copyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaroyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside and 26-O-β-d-glucopyranosyl-(25R and S)-5α-furostan-2α,3β,6β,22ξ,26-pentol 3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, respectively.
steroidal saponins, furostanol saponin, Allium schubertii, Liliaccae, bulbs, spirostanol saponins, aginoside, turoside A, benzoic acid esters, 3-hydroxy-3-methylglutaric acid ester
NCBI PubMed ID: 7763477Publication DOI: 10.1016/S0031-9422(00)95103-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Tokyo College of Pharmacy, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, methanolysis, HPLC, alkaline hydrolysis, enzymatic digestion, methylation analysis
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14. Compound ID: 24341
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b-D-Glcp-(1-2)-+
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b-D-Xylp3Bz-(1-3)-b-D-Glcp-(1-4)-b-D-Galp-(1-3)-Subst
Subst = 5α-spirostan-2α,3β,6β-triol = SMILES [H][C@]1(O[C@@]2(OCC(C)CC2)[C@H]3C)C[C@@]4([H])[C@]5([H])C{6}[C@@H](O)[C@@]6([H])C{3}[C@@H](O){2}[C@H](O)C[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H];
Bz = benzoic acid |
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Structure type: oligomer
; 1170 [M]-
C57H86O25
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136044,IEDB_137472,IEDB_139965,IEDB_140628,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 9942
Kawashima K, Mimaki Y, Sashida Y "Steroidal saponins from the bulbs of Allium schubertii" -
Phytochemistry 32 (1993) 1267-1272
Phytochemical examination of the fresh bulbs of Allium schubertii led to the isolation of four new steroidal saponins together with a known saponin. The structures of the new saponins were established by spectroscopic data, hydrolysis and chemical correlation as (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[3-O-benzoyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glu-copyranosyl-(1→4)-β-d-galactopyranoside, (25R and S)-5α-spirostan-2α,3β,6β-triol 3-O-β-d-glucopyranosyl-(1→2)-O-[4-O-(3S)-3-hydroxy-3-methylglutaroyl-β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside and 26-O-β-d-glucopyranosyl-(25R and S)-5α-furostan-2α,3β,6β,22ξ,26-pentol 3-O-β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside, respectively.
steroidal saponins, furostanol saponin, Allium schubertii, Liliaccae, bulbs, spirostanol saponins, aginoside, turoside A, benzoic acid esters, 3-hydroxy-3-methylglutaric acid ester
NCBI PubMed ID: 7763477Publication DOI: 10.1016/S0031-9422(00)95103-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Tokyo College of Pharmacy, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, methanolysis, HPLC, alkaline hydrolysis, enzymatic digestion, methylation analysis
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15. Compound ID: 24875
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b-D-Digp3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Olip3Me-(1-4)-b-D-Digp3Me-(1-4)-b-D-Digp3Me-(1-3)-Subst12Bz
Subst = lineolon = SMILES CC([C@@H]1CC{14}[C@]2(O){8}[C@]3(O)CC=C4C{3}[C@@H](O)CC[C@]4(C)[C@@]3([H])C{12}[C@@H](O)[C@]12C)=O |
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Structure type: oligomer
Trivial name: calotroposide A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_139965
The structure is contained in the following publication(s):
- Article ID: 10133
Shibuya H, Zhang RS, Park JD, Baek NI, Takeda Y, Yoshikawa M, Kitagawa I "Indonesian medicinal plants. V. Chemical structures of calotroposides C, D, E, F, and G, five additional new oxypregnane-oligoglycosides from the root of Calotropis gigantea (Asclepiadaceae)" -
Chemical and Pharmaceutical Bulletin 40 (1992) 2647-2653
Following the chemical characterization of calotroposides A (1) and B (2), five related oxypregnane-oligoglycosides named calotroposides C (3), D (4), E (5), F (6), and G (7) have benn additionally isolated from the root of Calotropis gigantea (Asclepiadaceae), an Indonesian medicinal plant. The chemical structures of the new calotroposides have been elucidated on the basis of chemical and physicochemical properties as 12-O-benzoyldeacetylmetaplexigenin 3-O-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside for 3, 12-O-benzoyllineolon 3-O-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside for 4, 12-O-benzoyldeacetylmetaplexigenin 3-O-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside for 5, 12-O-benzoyllineolon 3-O-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside for 6, and 12-O-benzoyllineolon 3-O-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside for 7.
Asclepiadaceae, Indonesian medicinal plant, Calotropis gigantea, oxypregnane-oligoglycoside, calotroposide, cymarose, oleandrose
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003654890Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Osaka University, Osaka, japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, partial acid hydrolysis, acid hydrolysis, methanolysis, UV, acetylation analysis
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