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1. (Article ID: 11131)
Shirasuna K, Miyakoshi M, Mimoto S, Isoda S, Satoh Y, Hirai Y, Ida Y, Shoji J
Lupane triterpenoid glycosyl esters from leaves of Acanthopanax divaricatus
Phytochemistry 45(3) (1997)
579-584
Further investigation of the leaves of Acanthopanax divaricatus gave two analogues of chiisanoside, which is a lupane triterpenoid oligoglycosyl ester. The structures were established as 28-O-α-l-rhamnopyranosyl(1→4)-β-d-glucopyranosyl(1→6)β-d-glucopyranosyl esters of 1β,11α-dihydroxy-3-oxo-lup-20(29)-en-28-oic acid and 1(R),11α,22α-trihydroxy-3,4-seco-lupa-4(23),20(29)-diene-3,28-dioic acid 3,11α-lactone based on chemical and spectroscopic evidence. in biosynthetic terms, one is the precursor of chiisanoside and the other is an oxygenated derivative chiisanoside.
araliaceae, triterpenoid saponin, Acanthopanax divaricatus, lupane glycoside, chiisanoside, isochiisanoside, protochiisanoside, 22α-hydroxychiisanoside
Publication DOI: 10.1016/S0031-9422(97)00017-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: School of Pharmaceutical Sciences, Showa University, Hatamodai 1-5-8, Shinagawa-ku Tokyo 142, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, sugar analysis, TLC, enzymatic hydrolysis, acid hydrolysis, GC, chemical methods, extraction
The publication contains the following compound(s):
- Compound ID: 21989
Structure type: monomer
Trivial name: hyperoside, hyperin, hyperoside, hyperin, baohuoside-II, quercetin 3-galactoside, vulgarsaponin B
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside, flavanone glycoside
Reference(s) to other database(s): CCSD:
49969, CBank-STR:1983
- Compound ID: 22453
Structure type: monomer
C21H20O11
Trivial name: quercitrin, baohuoside-II, quercetin 3-rhamnoside, quercetin 3-O-rhamnoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside
Reference(s) to other database(s): CCSD:
49971, CBank-STR:599
- Compound ID: 27809
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a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = 3-oxo-lup-20(29)-en-1β,11α-diol-28-oic acid = SMILES CC1(C)C(C{1}[C@@H](O)[C@]2(C)[C@@]3([H]){11}[C@H](O)C[C@]4([H])[C@@]5([H])[C@H](C(C)=C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H])=O |
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Structure type: oligomer
; 955 [M-H]-
C48H76O19
Trivial name: protochiisanoside
Compound class: saponin glycoside
- Compound ID: 27810
Structure type: oligomer
Trivial name: protochiisanoside
Compound class: saponin glycoside
Reference(s) to other database(s): GTC:G80817ZD
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