ABSTRACT
Five oleanane-type saponins, 3-O-ß-D-glucuronopyranosylzanhic acid 28-O-ß-D-xylopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-(4-O-acetyl)-ß-D-fucopyranosyl ester (1), 3-O-ß-D-glucopyranosylzanhic acid 28-O-ß-D-xylopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-(4-O-acetyl)-ß-D-fucopyranosyl ester (2), zanhic acid 28-O-ß-D-xylopyranosyl-(1â3)-[α-L-rhamnopyranosyl-(1â2)]-(4-O-acetyl)-ß-D-fucopyranosyl ester (3), zanhic acid 28-O-α-L-rhamnopyranosyl-(1â2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-ß-D-fucopyranosyl ester (4), medicagenic acid 28-O-α-L-rhamnopyranosyl-(1â2)-4-O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-ß-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the ß-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/chemical synthesis , Antineoplastic Agents, Phytogenic/chemical synthesis , Biological Products/chemical synthesis , Oleanolic Acid/analogs & derivatives , Sapindaceae/chemistry , Saponins/chemical synthesis , Acylation , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Biological Products/chemistry , Biological Products/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Hydrolysis , Inflammation/drug therapy , Mice , Molecular Conformation , Oleanolic Acid/chemistry , Plant Roots/chemistry , Saponins/chemistry , Saponins/pharmacology , Structure-Activity RelationshipABSTRACT
Four known serjanic acid glycosides were isolated from the fruits of Phytolacca rugosa and characterized mainly by 2D NMR spectroscopy and mass spectrometry. This aglycon has a chemotaxonomic significance for the genus Phytolacca.
Subject(s)
Fruit/chemistry , Phytolacca/chemistry , Plant Extracts/isolation & purification , Saponins/isolation & purification , Triterpenes/isolation & purification , Chromatography, Liquid , Magnetic Resonance Spectroscopy , Mass Spectrometry , VenezuelaABSTRACT
One new diterpene, 2 alpha-hydroxy-12beta-hydroxy-isopimara-8(14), 15-diene, and six known compounds as triterpenes, sterols and fatty acid, were isolated from the stem bark of Tanaecium jaroba (Bignoniaceae), a Bolivian plant used in traditional medicine. Their structures were established mainly by 1D and 2D NMR (COSY, HMQC, HMBC, ROESY) and their antiplasmodial activities were evaluated in vitro against Plasmodium falciparum.