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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)-+
|
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
|
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 |
Show graphically |
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)-+
|
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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