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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] |
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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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2. (Article ID: 10915)
Li-Xian G, Xiao-Bing H, Yu-Qun C
The structures of thirteen astrasieversianins from Astragalus sieversianus
Phytochemistry 25 (1986)
2389-2393
Based on spectroscopic analysis and chemical degradations, the structures of the five new glycosides, astrasieversianins I, III, V, XII and XIII were assigned as the 3-O-(2′,3′,4′-tri-O-acetyl)-β-d-xylopyranoside, 3-O-(2′,4′,-di-O-acetyl-β-d-xylopyranoside, 3-O-(3′-O-acetyl)-β-d-xylopyranosyl-6-O-β-d-xylopyranoside, 3-O-α-l-rhamno-pyranosyl(1→2)]-(3t́-O-acetyl)-β-d-xylopyranosyl-6-O-β-d-glucopyranoside and 3-O-α-l-rhamnopyranosyl(1→2)]-(4′-O-acetyl)-β-d-xylopyranosyl-6-O-β-d-glucopyranoside of astramembrangenin, respectively. Astrasieversianins II, VI, X and XVI were established as 20,24-epimers of cyclosieversiosides A, C, E and H respectively. Astrasieversianins IV, VII, VIII and XIV were identified as known naturally occurring triterpenoid glycosides.
Leguminosae, triterpenoid saponins, Astragalus sieversianus, cycloartane triterpene, astrasieversianin
Publication DOI: 10.1016/S0031-9422(00)81702-1Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Shanghai Institute of Organic Chemistry, Academia Sinica, Shanghai, China, Xinjian Institute of Chemistry, Academia Sinica, Wulumugi, China
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, methanolysis, FD-MS, methyaltion analysis
The publication contains the following compound(s):
- Compound ID: 27168
|
b-D-Xylp-(1-6)-+
|
b-D-Xylp2Ac3Ac4Ac-(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
; 881 [M+H]+
C46H72O16
Trivial name: astrasieversianin I
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49751, CBank-STR:2885
- Compound ID: 27169
|
b-D-Xylp-(1-6)-+
|
b-D-Xylp2Ac3Ac-(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
; 839 [M+H]+
C44H70O15
Trivial name: astrasieversianin II
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49752, CBank-STR:2883
- Compound ID: 27170
|
b-D-Xylp-(1-6)-+
|
b-D-Xylp2Ac4Ac-(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
; 838 [M]+
C44H70O15
Trivial name: astrasieversianin III
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49753, CBank-STR:2884
- Compound ID: 27171
|
b-D-Xylp-(1-6)-+
|
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
; 820 [M+Na+H]+
Trivial name: astrasieversianin V
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49754, CBank-STR:2881
- Compound ID: 27172
|
b-D-Xylp-(1-6)-+
|
b-D-Xylp2Ac-(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
; 797 [M+H]+
C42H64O14
Trivial name: astrasieversianin VI
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49755, CBank-STR:2880
- Compound ID: 27173
|
b-D-Xylp-(1-6)-+
|
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] |
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Structure type: oligomer
; 755 [M+H]+
C40H66O13
Trivial name: astrasieversianin X
Compound class: glycoside
Reference(s) to other database(s): CCSD:
49756, CBank-STR:2877
- Compound ID: 27174
|
b-D-Glcp-(1-6)-+
|
b-D-Xylp2Ac3Ac-(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
; 869 [M+H]+
C45H72O16
Trivial name: astrasieversianin IV (astragaloside I)
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49757, CBank-STR:2913
- Compound ID: 27175
|
b-D-Glcp-(1-6)-+
|
b-D-Xylp2Ac-(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
; 826 [M]+
C43H70O15
Trivial name: astrasieversianin VII (isoastragaloside)
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49758, CBank-STR:2908
- Compound ID: 27176
|
b-D-Glcp-(1-6)-+
|
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
; 826 [M]+
C43H70O15
Trivial name: astrasieversianin VIII (astragaloside II)
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49759, CBank-STR:2909
- Compound ID: 27177
|
b-D-Glcp-(1-6)-+
|
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] |
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Structure type: oligomer
; 785 [M+H]+
C41H68O14
Trivial name: astrasieversianin XIV
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49760, CBank-STR:2905
- Compound ID: 27178
|
b-D-Glcp-(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
; 995 [M+Na]+
C49H80O19
Trivial name: astrasieversianin XII
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49761, CBank-STR:6705
- Compound ID: 27179
|
b-D-Glcp-(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
; 973 [M+H]+
C49H80O19
Trivial name: astrasieversianin XIII
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49762, CBank-STR:6706
- Compound ID: 27180
|
b-D-Glcp-(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] |
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Structure type: oligomer
; 930 [M]+
C47H78O18
Trivial name: astrasieversianin XVI
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
49763, CBank-STR:6702
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