Three new triterpene saponins from two species of Carpolobia

Anne-Claire Mitaine-Offer; Tomofumi Miyamoto; Ikhlas A Khan; Clément Delaude; Marie-Aleth Lacaille-Dubois

doi:10.1021/np010546e

Three new triterpene saponins from two species of Carpolobia

J Nat Prod. 2002 Apr;65(4):553-7. doi: 10.1021/np010546e.

Authors

Anne-Claire Mitaine-Offer¹, Tomofumi Miyamoto, Ikhlas A Khan, Clément Delaude, Marie-Aleth Lacaille-Dubois

Affiliation

¹ Laboratoire de Pharmacognosie, Unité MIB, J E 2244, Faculté de Pharmacie, Université de Bourgogne, 7, Bd. Jeanne D'Arc, BP 87900, 21079 Dijon Cedex, France.

PMID: 11975499
DOI: 10.1021/np010546e

Abstract

Three new acetylated triterpene saponins 1-3 were isolated from the roots of Carpolobia alba and C. lutea. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->3)]-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, and 3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-->4)-[beta-D-apiofuranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester, respectively.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology
Chromatography, Thin Layer
Cisplatin / pharmacology
Colonic Neoplasms
Drug Screening Assays, Antitumor
Humans
Hydrolysis
Molecular Structure
Nigeria
Nuclear Magnetic Resonance, Biomolecular
Oleanolic Acid* / analogs & derivatives*
Plants, Medicinal / chemistry*
Polygalaceae / chemistry*
Saponins / chemistry
Saponins / isolation & purification*
Saponins / pharmacology
Stereoisomerism
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / pharmacology
Tumor Cells, Cultured / drug effects

Substances

3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-4)-(alpha-L-arabinopyranosyl-(1-3))-beta-D-xylopyranosyl-(1-4)-alpha-L-rhamnopyranosyl-(1-2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester
3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-galactopyranosyl-(1-4)-(beta-D-xylopyranosyl-(1-3))-beta-D-xylopyranosyl-(1-4)-alpha-L-rhamnopyranosyl-(1-2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester
3-O-beta-D-glucopyranosylpresenegenin-28-O-beta-D-xylopyranosyl-(1-4)-(beta-D-apiofuranosyl-(1-3))-alpha-L-rhamnopyranosyl-(1-2)-(3,4-di-O-acetyl)-beta-D-fucopyranosyl ester
Antineoplastic Agents, Phytogenic
Saponins
Triterpenes
Oleanolic Acid
Cisplatin