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1. (Article ID: 10914)
Li-Xian G, Xiao-Bing H, Yu-Qun C
Astrasieversianins IX, XI and XV, cycloartane derived saponins from Astragalus sieversianus
Phytochemistry 25 (1986)
1437-1441
Sixteen triterpenoid saponins, astrasieversianins I–XVI, have been isolated from the methanol extract of the roots of Astragalus sieversianus. By heterogeneous acidic hydrolysis, all glycosides produced only one common aglycone which was identified as the known natural product astramembrangenin or cycloastragenol. On the basis of spectral analysis and chemical reactions, the structures of two new triterpenoid glycosides, astrasieversianin IX and XI, were assigned as the 3-0-[α-l-rhamnopyranosyl(1→2)]-(3′-O-acetyl)-β-d-xylopyranosyl-6-O-β-d-xylopyranoside and the 3-O-[α-l-rhamnopyranosyl(1→2)]-(4′-O-acetyl)-β-d-xylopyranosyl-6-β-d-xylopyranoside of cycloastragenol. Astrasieversianin XV was identified as the 20,24-epimer (20R,24S) of cyclosieversiside G (20S,24R).
Leguminosae, triterpenoid saponins, Astragalus sieversianus, cycloartane triterpene, astrasieversianin, astrasieversiagenin
Publication DOI: 10.1016/S0031-9422(00)81305-9Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai, China, Xinjian Institute of Chemistry, Academic Sinica, Wulumugi, China
Methods: 13C NMR, 1H NMR, EI-MS, IR, TLC, acid hydrolysis, GLC, CD, methylation analysis, CC, oxidation, FD-MS, PC
The publication contains the following compound(s):
- Compound ID: 27165
|
b-D-Xylp-(1-6)-+
|
a-L-Rhap-(1-2)-b-D-Xylp3Ac-(1-3)-Subst
Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H] |
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Structure type: oligomer
; 965 [M+Na]+
Trivial name: astrasieversianin IX
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49748, CBank-STR:6666
- Compound ID: 27166
|
b-D-Xylp-(1-6)-+
|
a-L-Rhap-(1-2)-b-D-Xylp4Ac-(1-3)-Subst
Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H] |
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Structure type: oligomer
; 943 [M+H]+
Trivial name: astrasieversianin XI
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49749, CBank-STR:6667
- Compound ID: 27167
|
b-D-Xylp-(1-6)-+
|
a-L-Rhap-(1-2)-b-D-Xylp-(1-3)-Subst
Subst = astramembrangenin = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C3)C43CC[C@]5(C)[C@@H]([C@](C)(O6)CC[C@H]6{25}C(C)(O)C){16}[C@@H](O)C[C@](C)5[C@]4([H])C{6}[C@H](O)[C@@]12[H] |
Show graphically |
Structure type: oligomer
; 901 [M+H]+
Trivial name: astrasieversianin XV
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49750, CBank-STR:6665
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