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1. (Article ID: 10717)
Sakurai N, Koeda M, Inoue T, Nagai M
Studies on the chinese crude drug 'shoma.' VIII. Two new triterpenol bisdesmosides, 3-arabinosyl-24-O-acetylhydroshengmanol 15-glucoside and 3- xylosyl-24-O-acetylhydroshengmanol 15-glucoside, from Cimicifuga dahurica
Chemical and Pharmaceutical Bulletin 42(1) (1994)
48-51
Two new triterpenol glycosides were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae) : 3-arabinosyl-24-O-acetylhydroshengmanol 15-glucoside (1), C_<43>H_<70>O_<16>, mp 222-223℃, [α]_D +21.0° and 3-xylosyl-24-O-acetylhydroshengmanol 15-glucoside (2), C_<43>H_<70>O_<16>, mp 208-210℃, [α]_D+9.5°. On acidic hydrolysis, 1 afforded cimigenol (3) as an aglycone, and glucose and arabinose as sugars. On enzymatic hydrolysis with molsin, 1 afforded 24-O-acetylhydroshengmanol 15-O-glucoside (4). On the basis of chemical and spectral data, the structure of 1 was proposed to be (23R, 24S)-24-acetoxy-3-O-α-L-arabinopyranosyloxy-16,23-epoxy-9,19-cyclolanostane-15α,16ξ,25-triol 15-O-β-D-glucopyranoside.The other glycoside (2) showed, in its ^<13>C-NMR spectrum, a pattern of chemical shifts very similar to that of 1. On acidic hydrolysis, 2 afforded cimigenol (3), xylose and glucose. On enzymatic hydrolysis with molsin, 2 afforded 4. From these results, the structure of 2 was proposed to be (23R, 24S)-24-acetoxy-3-O-β-D-xylo-pyranosyloxy-16,23-epoxy-9,19-cyclolanostane-15α,16ξ,25-triol 15-O-β-D-glucopyranoside.
NCBI PubMed ID: 8124764Publication DOI: 10.1248/cpb.42.48Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Science, Hoshi University, Japan
The publication contains the following compound(s):
- Compound ID: 26625
|
a-L-Arap-(1-3)-+
|
b-D-Glcp-(1-15)-Subst24Ac
Subst = SMILES C[C@@H]1C[C@H]({24}[C@H](O)C(C)(C)O)O{16}C2(O)[C@H]1[C@@]3(C)CC[C@@]45C[C@@]46CC{3}[C@H](O)C(C)(C)[C@@H]6CC[C@H]5[C@]3(C){15}[C@H]2O |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40095, CBank-STR:3634
- Compound ID: 26626
|
b-D-Xylp-(1-3)-+
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b-D-Glcp-(1-15)-Subst24Ac
Subst = SMILES C[C@@H]1C[C@H]({24}[C@H](O)C(C)(C)O)O{16}C2(O)[C@H]1[C@@]3(C)CC[C@@]45C[C@@]46CC{3}[C@H](O)C(C)(C)[C@@H]6CC[C@H]5[C@]3(C){15}[C@H]2O |
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Structure type: oligomer
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
40096, CBank-STR:4553
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2. (Article ID: 11805)
Ye W, Zhang J, Che CT, Ye T, Zhao S
New cycloartane glycosides from Cimicifuga dahurica
Planta Medica 65(8) (1999)
770-772
Two new cylcoartane glycosides along with a known compound, 12β-hydroxycimigenol 3-O-α-L-arabinopyranoside, were isolated from the rhizomes of Cimicifuga dahurica (Ranunculaceae). The structures of the new compounds were elucidated as cimigenol 3-O-α-L-arabinopyranoside and 25-O-acetylcimigenol 3-O-α-L-arabinopyranoside on the basis of chemical and spectral evidence.
glycoside, saponin, cycloartane, Cimicifuga dahurica
NCBI PubMed ID: 17260302Publication DOI: 10.1055/s-2006-960865Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: Che CT
cuhk.edu.hk>
Institutions: Department of Phytochemistry, China Pharmaceutical University, Nanjing, China, Department of Chemistry, the Hong Kong University of Science and Technology, Hong Kong, China, School of Chinese Medicine, the Chinese University of Hong Kong, Shatin, Hong Kong, China, Department of Chemistry, The University of Hong Kong, Hong Kong, China
Methods: 13C NMR, 1H NMR, IR, TLC, ESI-MS, alkaline hydrolysis, optical rotation measurement, HPTLC, ROESY, HMBC, DEPT, COSY, HCl hydrolysis
The publication contains the following compound(s):
- Compound ID: 30501
|
a-L-Arap-(1-3)-Subst
Subst = 12β-hydroxycimigenol = SMILES C[C@@H]1C[C@@H]2O[C@]3(O[C@@H]2{25}C(C)(C)O)[C@@H]1[C@@]1(C){12}[C@H](O)C[C@@]24C[C@@]25CC{3}[C@H](O)C(C)(C)[C@@H]5CC[C@H]4[C@]1(C){15}[C@H]3O |
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Structure type: monomer
; 637 [M+H]+
Compound class: saponin glycoside
- Compound ID: 30502
|
a-L-Arap-(1-3)-Subst
Subst = cimigenol = SMILES C[C@@H]1C[C@H]2O[C@@]3(O[C@@H]2{25}C(C)(C)O){15}[C@H](O)[C@@]2(C)[C@@H]4CC[C@H]5C(C)(C){3}[C@@H](O)CC[C@@]56C[C@@]46CC[C@]2(C)[C@@H]13 |
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Structure type: monomer
; 621 [M+H]+
C35H56O9
Compound class: saponin glycoside
- Compound ID: 30503
|
a-L-Arap-(1-3)-Subst25Ac
Subst = cimigenol = SMILES C[C@@H]1C[C@H]2O[C@@]3(O[C@@H]2{25}C(C)(C)O){15}[C@H](O)[C@@]2(C)[C@@H]4CC[C@H]5C(C)(C){3}[C@@H](O)CC[C@@]56C[C@@]46CC[C@]2(C)[C@@H]13 |
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Structure type: monomer
; 663 [M+H]+
C37H58O10
Compound class: saponin glycoside
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