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1. (Article ID: 10870)
Siddiqui HL, Munesada K, Suga T
Biologically active clerodane-type diterpene alcohol and its glycosides from the root-stalks of ferns
Journal of the Chemical Society, Perkin Transactions 1 (1992)
781-785
A diterpene alcohol showing a growth inhibition of lettuce was isolated from the root-stalks of Dicranopteris pedata and Gleichenia japonica. Its structure was determined to be (6S,13S)-cleroda-3,14-diene-6,13-diol 1, an aglycone of the two glycosides previously isolated from G. japonica; the chirality at both C-6 and C-13 was assigned as S by application of the β-D-glucosylation-shift rule and by measurement of 13C NMR chemical shifts, respectively. Further, two glycosides showing growth inhibition were also isolated from D. pedata and they were characterised as the 13-O-β-L-fucopyranosyl-(1→2)-α-L-rhamnopyranoside 3 and 13-O-α-L-fuoopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-α-L-rhamnopyranoside 4 of the diterpene alcohol; the above assignment of the chirality at C-13 was established by measurement of nuclear Overhauser enhancement for the trisaccharide. In addition, a glycoside showing growth acceleration was also isolated and its structure was determined to be (6S,13S)-13-O-β-L-fucopyranosyl-6-O-α-L-rhamnopyranosylcleroda-3,14-diene-6,13-diol 2.
Publication DOI: 10.1039/P19920000781Journal NLM ID: 7505598Publisher: Chemical Society
Institutions: Department of Chemistry, Faculty of Science, Hiroshima University, Hiroshima, Japan
Methods: 13C NMR, 1H NMR, EI-MS, GLC-MS, FAB-MS, TLC, GLC, enzymatic digestion, biological assay, SI-MS, acetylation analysis
The publication contains the following compound(s):
- Compound ID: 27054
|
b-D-Glcp-(1-6)-Subst
Subst = cleroda-3,14-dien-6S,13S-diol = SMILES CC1=CCC[C@@]2([H])[C@](C)(CC{13}[C@@](C=C)(O)C)[C@@H](C)C{6}[C@H](O)[C@]12C |
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Structure type: monomer
; 467.3001 [M-H]-
C26H43O7
Reference(s) to other database(s): CCSD:
48260, CBank-STR:1223
- Compound ID: 27055
|
a-L-Rhap-(1-2)-b-D-Glcp-(1-6)-Subst
Subst = cleroda-3,14-dien-6S,13S-diol = SMILES CC1=CCC[C@@]2([H])[C@](C)(CC{13}[C@@](C=C)(O)C)[C@@H](C)C{6}[C@H](O)[C@]12C |
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Structure type: oligomer
; 613.3596 [M-H]-
C32H53O11
Reference(s) to other database(s): CCSD:
48261, CBank-STR:3447
- Compound ID: 27051
|
b-L-Fucp-(1-6)-+
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a-L-Rhap-(1-13)-Subst
Subst = cleroda-3,14-dien-6S,13S-diol = SMILES CC1=CCC[C@@]2([H])[C@](C)(CC{13}[C@@](C=C)(O)C)[C@@H](C)C{6}[C@H](O)[C@]12C |
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Structure type: oligomer
; 597.3629 [M-H]-
C32H53O10
Reference(s) to other database(s): CCSD:
48257, CBank-STR:1812
- Compound ID: 27052
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b-L-Fucp-(1-2)-a-L-Rhap-(1-13)-Subst
Subst = cleroda-3,14-dien-6S,13S-diol = SMILES CC1=CCC[C@@]2([H])[C@](C)(CC{13}[C@@](C=C)(O)C)[C@@H](C)C{6}[C@H](O)[C@]12C |
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Structure type: oligomer
; 597.3627 [M-H]-
C32H53O10
Reference(s) to other database(s): CCSD:
48258, CBank-STR:2334
- Compound ID: 27053
|
a-L-Rhap-(1-3)-+
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a-L-Fucp-(1-2)-a-L-Rhap-(1-13)-Subst
Subst = cleroda-3,14-dien-6S,13S-diol = SMILES CC1=CCC[C@@]2([H])[C@](C)(CC{13}[C@@](C=C)(O)C)[C@@H](C)C{6}[C@H](O)[C@]12C |
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Structure type: oligomer
; 743.4214 [M-H]-
C38H63O14
Reference(s) to other database(s): CCSD:
48259, CBank-STR:4778
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2. (Article ID: 10871)
Vleggaar R, van Heerden FR, Anderson LAP, Erasmus GL
Toxic constituents of the asclepiadaceae. Structure elucidation of sarcovimiside A-C, pregnane glycosides of Sarcostemma viminale
Journal of the Chemical Society, Perkin Transactions 1 (1993)
483-487
The structure elucidation of three related pregnane glycosides, sarcovimiside A, B, and C from Sarcostemma viminale, is based on a detailed study of their highfield 1H and 13C NMR spectra. The results show that all the sugars are (1→4)-linked and both (β-D- and α-L-cymarose residues are present in each glycoside chain. The aglycone of sarcovimiside A was identified as 12β-benzoyloxy-3β,8β,14.17-tetrahydroxy-14β,17α-pregn-5-en-20-one whereas in the case of both sarcovimiside B and C, oxidative cleavage of the C(8)–C(14) bond occurred and the aglycone is the 12,20-O,O-dibenzoyl derivative of (20S)-3β,5,12β,17,20-pentahydroxy-8,14-seco-5β,17α-pregn-6-ene-8,14-dione. Sarcovimiside C is the β-(1→4)-glucopyranosyl derivative of sarcovimiside B.
Publication DOI: 10.1039/P19930000483Journal NLM ID: 7505598Publisher: Chemical Society
Institutions: Department of Chemistry, University of Pretoria, Pretoria, South Africa, Department of Chemistry and Biochemistry, Rand Afrikaans University, Auckland Park, South Africa, Department of Toxicology, Onderstepoort, Veterinary Institute, Onderstepoort, South Africa
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, enzymatic digestion, PLC, CC
The publication contains the following compound(s):
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