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1. (Article ID: 11375)
Bedir E, Calis I, Aquino R, Piacente S, Pizza C
Cycloartane triterpene glycosides from the roots of Astragalus brachypterus and Astragalus microcephalus
Journal of Natural Products 61(12) (1998)
1469-1472
Three new cycloartane-type triterpene glycosides, brachyosides A (1), B (3), and C (2), from the roots of Astragalus brachypterus and one new glycoside, cyclocephaloside II (4), from the roots of Astragalusmicrocephalus have been isolated together with five known saponins, astragalosides I, II, and IV, cyclocanthoside E, and cycloastragenol. The structures of the new compounds were established as 3-O-[beta-D-xylopyranosyl(1-->3)-beta-D-xylopyranosyl-6-O-beta-D-gluc opyranosyl-3beta,6alpha,16beta,24(S),25-pentahydrox ycycloartane (1), 3-O-beta-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-24-O-beta-D-glucop yranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxyc ycloartane (2), 20(R),24(S)-epoxy-6-O-beta-D-glucopyranosyl-3beta,6alpha,16beta , 25-tetrahydroxycycloartane (3), and 20(R), 24(S)-epoxy-3-O-(4'-O-acetyl)-beta-D-xylopyranosyl-6-O-beta-D-glucopy ranosyl-3beta,6alpha,16beta,25-tetrahydroxycycloart ane (4). For the structure elucidations, 1D- and 2D-NMR experiments and FABMS were used.
NMR, spectroscopy
NCBI PubMed ID: 9868145Publication DOI: 10.1021/np9801763Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Calis I
dominet.in.com.tr>
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey, Facoltà di Farmacia, Università degli Studi di Salerno, Penta di Fisciano, Salerno, Italy
Methods: 13C NMR, 1H NMR, FAB-MS, extraction, optical rotation measurement, TOCSY, CC, DQF-COSY, HMBC, DEPT, HOHAHA, HSQC
The publication contains the following compound(s):
- Compound ID: 27852
|
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] |
Show graphically |
Structure type: oligomer
C41H68O14
Trivial name: astragaloside I, astragaloside I (astrasieversianin IV)
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
- Compound ID: 28878
|
b-D-Glcp-(1-6)-+
|
b-D-Xylp-(1-3)-Subst
Subst = 3β,6α,16β,24(S),25-pentahydroxycycloartane = SMILES C[C@H](CC{24}[C@@H](O){25}C(C)(C)O)C4{16}[C@@H](O)C[C@@]5(C)C2C{6}[C@H](O)C1[C@@](C)(C){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C |
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Structure type: oligomer
C30H52O5
Trivial name: cyclocanthoside E
Compound class: saponin glycoside, triterpenoid glycoside
- Compound ID: 28879
|
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
Trivial name: astragaloside IV, astragalus saponin AS I, cycloastragenol
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
- Compound ID: 28882
|
b-D-Glcp-(1-6)-+
|
b-D-Xylp-(1-3)-b-D-Xylp-(1-3)-Subst
Subst = 3β,6α,16β,24(S),25-pentahydroxycycloartane = SMILES C[C@H](CC{24}[C@@H](O){25}C(C)(C)O)C4{16}[C@@H](O)C[C@@]5(C)C2C{6}[C@H](O)C1[C@@](C)(C){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C |
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Structure type: oligomer
; 917 [M-H]-
C46H78O18
Trivial name: brachyoside A
Compound class: triterpenoid glycoside
- Compound ID: 28883
|
b-D-Xylp-(1-3)-+
|
b-D-Glcp-(1-24)-Subst
|
b-D-Glcp-(1-6)-+
Subst = 3β,6α,16β,24(S),25-pentahydroxycycloartane = SMILES C[C@H](CC{24}[C@@H](O){25}C(C)(C)O)C4{16}[C@@H](O)C[C@@]5(C)C2C{6}[C@H](O)C1[C@@](C)(C){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C |
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Structure type: oligomer
; 947 [M-H]-
C47H80O19
Trivial name: brachyoside C
Compound class: triterpenoid glycoside
- Compound ID: 28884
|
b-D-Glcp-(1-6)-Subst
Subst = 3β,6α,16β,24(S),25-pentahydroxycycloartane = SMILES C[C@H](CC{24}[C@@H](O){25}C(C)(C)O)C4{16}[C@@H](O)C[C@@]5(C)C2C{6}[C@H](O)C1[C@@](C)(C){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C |
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Structure type: monomer
; 651
C36H60O10
Trivial name: brachyoside B
Compound class: triterpenoid glycoside
- Compound ID: 28885
|
b-D-Glcp-(1-6)-+
|
b-D-Xylp4Ac-(1-3)-Subst
Subst = 3β,6α,16β,24(S),25-pentahydroxycycloartane = SMILES C[C@H](CC{24}[C@@H](O){25}C(C)(C)O)C4{16}[C@@H](O)C[C@@]5(C)C2C{6}[C@H](O)C1[C@@](C)(C){3}[C@@H](O)CC[C@@]13C[C@@]23CC[C@]45C |
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Structure type: oligomer
; 825 [M-H]-
C43H70O15
Trivial name: cyclocephaloside II
Compound class: triterpenoid glycoside
- Compound ID: 28886
|
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] |
Show graphically |
Structure type: oligomer
Trivial name: astragaloside II
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
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