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1. (Article ID: 11352)
Baykal T, Panayir T, Tasdemir D, Sticher O, Calis I
Triterpene saponins from Scabiosa rotata
Phytochemistry 48(5) (1998)
867-873
Four new allose-containing triterpenoid saponosides, scabriosides A, B, C and D were isolated from the roots of Scabiosa rotata. Their structures were established as 3-O-beta-D-xylopyranosyl-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, 3-O-[alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-allopyranosyl (1-->6)-beta-D-glucopyranosyl]-pomolic acid, and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->2)-beta-D-xylopyranosyl]-28-O-[beta-D-allopyranosyl(1-->6) -beta-D-glucopyranosyl]-pomolic acid, respectively, by the help of spectral evidence (IR, 1D- and 2D-NMR, FAB-MS).
pomolic acid, Dipsacaceae, Scabiosa rotata, triterpenoid saponosides, Scabrioside A, Scabrioside B, Scabrioside C, Scabrioside D
NCBI PubMed ID: 9664710Publication DOI: 10.1016/s0031-9422(97)00982-5Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: Calis I
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Institutions: Swiss Federal Institute of Technology (ETH) Zürich, Department of Pharmacy, Zürich, Switzerland, Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turkey, Department of Pharmacognosy, Faculty of Pharmacy, Hacettepe University Ankara, Turkey
Methods: 13C NMR, 1H NMR, IR, FAB-MS, GC-MS, TLC, extraction, CC, HMBC, HMQC, COSY, optical rotatin measurement
The publication contains the following compound(s):
- Compound ID: 28807
|
b-D-Xylp-(1-3)-+
|
b-D-Allp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 951 [M+Na]+
C47H76O18
Trivial name: scabrioside A
Compound class: triterpenoid glycoside
- Compound ID: 28808
|
a-L-Rhap-(1-2)-b-D-Xylp-(1-3)-+
|
b-D-Allp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1097 [M+Na]+
C53H86O22
Trivial name: scabrioside B
Compound class: triterpenoid glycoside
- Compound ID: 28809
|
a-L-Rhap-(1-2)-b-D-Arap-(1-3)-+
|
b-D-Allp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1097 [M+Na]+
C53H86O22
Trivial name: scabrioside C
Compound class: triterpenoid glycoside
- Compound ID: 28810
|
b-D-Allp-(1-6)-b-D-Glcp-(1-28)-+
|
b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Xylp-(1-3)-Subst
Subst = pomolic acid = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H]){19}[C@](C)(O)[C@H](C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
; 1259 [M+Na]+
C59H96O27
Trivial name: scabrioside D
Compound class: triterpenoid glycoside
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