Isolation and structures of avicins D and G: in vitro tumor-inhibitory saponins derived from Acacia victoriae

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2003-06, Vol.66 (6), p.779-783
• Main Authors: Jayatilake, G.S, Freeberg, D.R, Liu, Z, Richheimer, S.L, Blake, M.E, Bailey, D.T, Haridas, V, Gutterman, J.U
• Format: Article
• Language: English
• Subjects: Acacia; Acacia - chemistry; Acacia victoriae; acacie acid; acid hydrolysis; apoptosis; Arizona; avicins; basic hydrolysis; biochemical pathways; Biological and medical sciences; carboxylic acids; cell lines; chemical structure; cytotoxicity; Drug Screening Assays, Antitumor; Fabaceae; General pharmacology; glycosides; Humans; Jurkat Cells; legumes; Medical sciences; Molecular Structure; monosaccharides; monoterpenoids; Nuclear Magnetic Resonance, Biomolecular; oligosaccharides; Oligosaccharides - chemistry; Oligosaccharides - isolation & purification; Oligosaccharides - pharmacology; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; plant extracts; Plants, Medicinal - chemistry; prosaponins; quinovose; saponins; Saponins - chemistry; Saponins - isolation & purification; Saponins - pharmacology; seeds; spectral analysis; sugars; Terpenes - chemistry; Terpenes - isolation & purification; Terpenes - pharmacology; triterpenoid saponins; Tumor Cells, Cultured - drug effects
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np020400v

Two new saponins named avicins D (1) and G (2) were isolated from the seed pods of the desert legume plant Acacia victoriae. The structures, elucidated by 1D and 2D NMR studies and by chemical means, were characterized as acacic acid-bearing oligosaccharides at C-3 and C-28 with a side chain linked to C-21 comprised of two monoterpene carboxylic acids and a quinovose moiety. Both compounds exhibited potent cytotoxicity (apoptosis) against human T-cell leukemia (Jurkat cells) in vitro.