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1. (Article ID: 10772)
Takaashi Y, Mimaki Y, Kameyama A, Kuroda M, Sashida Y, Nikaido T, Koike K, Ohmoto T
Three new cholestane bisdesmosides from Nolina recurvata stems and their inhibitory activity on cAMP phosphodiesterase and Na+/K+ ATPase
Chemical and Pharmaceutical Bulletin 43 (1995)
1180-1185
Fresh stems of Nolina recurvata were found to contain three new cholestane bisdesmosides. Their structures were determined on the basis of spectroscopic data and acid-catalyzed hydrolysis to be (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 1-O-β-D-glucopyranoside 16-O-α-L-rhamnopyranoside (1), (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 1,16-di-O-β-D-glucopyranoside (2) and (22S)-cholest-5-ene-1β,3β,16β,22-tetrol 1-O-{O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside} 16-O-α-L-rhamnopyranoside (3), respectively. The prominent downfield shift of the aglycone 19-Me of 3,compared with that of 1 and 2,is likely caused by the interaction between the 19-Me and 6'''-Me of the rhamnose attached to C-2 of the inner glucose, evidence for which was provided through molecular mechanics and molecular dynamics calculation studies and by the nuclear Overhauser effect (NOE) correlation spectrum. The isolated compounds and their derivatives were evaluated for their inhibitory activity on cAMP phosphodiesterase and Na^+/K^+ ATPase.
conformational analysis, Na+/K+ ATPase inhibition, Agavaceae, cAMP phosphodiesterase inhibition, Nolina recurvata, cholestane bisdesmoside
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003631631Publisher: Pharmaceutical Society Of Japan
Institutions: School of Pharmaceutical Sciences, Toho University, Japan, School of Pharmacy, Tokyo University of Pharmacy and Life Science (formerly, Tokyo College of Pharmacy), Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, partial acid hydrolysis, TLC, acid hydrolysis, HPLC, UV, CI-MS, biological assay, acetylation analysis
The publication contains the following compound(s):
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2. (Article ID: 10976)
Takaashi Y, Mimaki Y, Kuroda M, Sashida Y, Nikaido T, Ohmoto T
Recurvosides A-E, new polyhydroxylated steroidal saponins from Nolina recurvata stems
Tetrahedron 51 (1995)
2281-2292
A series of five new polyhydroxylated steroidal saponins, named recurvosides A - E, were isolated from the stems of Nolina recurvata (Agavaceae). Their structures were determined through detailed interpretation of various spectra, including two-dimensional (2D) NMR, and by acid-catalized hydrolysis. Among them, recurvoside E was revealed to be very unique in structure being a trisdesmoside with a β-d-fructofuranose as the monosaccharide component attached to the C-21 hydroxyl group of the aglycone. The isolated saponins were evaluated for inhibitory activity on cAMP phosphodiesterase as a primary screening test to find new biologically active compounds.
Publication DOI: 10.1016/0040-4020(94)01098-KJournal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: School of Pharmaceutical Sciences, Toho University, Miyama, Funabashi, Chiba, Japan, School of Pharmacy, Tokyo University of Pharmacy and Life Science (formerly, Tokyo College of Pharmacy), Tokyo, Japan
Methods: 13C NMR, 1H NMR, IR, FAB-MS, partial acid hydrolysis, TLC, acid hydrolysis, HPLC, CC, biological assay
The publication contains the following compound(s):
- Compound ID: 27360
|
b-D-Xylp-(1-3)-+
|
a-L-Rhap-(1-2)-a-L-Arap-(1-1)-Subst
Subst = spirosta-5,25(27)-diene-1β,3β,23S-triol = SMILES [H][C@]1(O[C@](OCC2=C)({23}[C@@H](O)C2)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 853 [M-H]-
C43H66O17
Trivial name: recurvoside A
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
50590, CBank-STR:5296
- Compound ID: 27361
|
b-D-Xylp-(1-3)-+
|
a-L-Rhap-(1-2)-a-L-Arap-(1-1)-Subst
Subst = spirosta-5,25(27)-diene-1β,3β,23S,24S-tetrol = SMILES [H][C@]1(O[C@](OCC2=C)({23}[C@@H](O){24}[C@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 869 [M-H]-
C43H66O18
Trivial name: recurvoside B
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
50591, CBank-STR:5297
- Compound ID: 27362
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b-D-Fucp-(1-24)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap-(1-2)-a-L-Arap-(1-1)-Subst
Subst = spirosta-5,25(27)-diene-1β,3β,23S,24S-tetrol = SMILES [H][C@]1(O[C@](OCC2=C)({23}[C@@H](O){24}[C@H]2O)[C@H]3C)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1015 [M-H]-
C49H76O22
Trivial name: recurvoside C
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
50592, CBank-STR:9468
- Compound ID: 27363
|
b-D-Fucp-(1-24)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap-(1-2)-a-L-Arap-(1-1)-Subst
Subst = spirosta-5,25(27)-diene-1β,3β,21,23S,24S-pentol = SMILES [H][C@]1(O[C@](OCC2=C)({23}[C@@H](O){24}[C@H]2O)[C@H]3{21}CO)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1031 [M-H]-
C49H76O23
Trivial name: recurvoside D
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
50593, CBank-STR:9469
- Compound ID: 27364
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b-D-Fruf-(2-21)-+
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b-D-Xylp-(1-3)-+ |
| |
a-L-Rhap-(1-2)-a-L-Arap-(1-1)-Subst
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b-D-Fucp-(1-24)-+
Subst = spirosta-5,25(27)-diene-1β,3β,21,23S,24S-pentol = SMILES [H][C@]1(O[C@](OCC2=C)({23}[C@@H](O){24}[C@H]2O)[C@H]3{21}CO)C[C@@]4([H])[C@]5([H])CC=C6C{3}[C@@H](O)C{1}[C@@H](O)[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@]13[H] |
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Structure type: oligomer
; 1194 [M]-
C55H86O28
Trivial name: recurvoside E
Compound class: saponin glycoside
Reference(s) to other database(s): CCSD:
50594, CBank-STR:11877
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