ABSTRACT
The haemolytic activity of saponins has been a known phenomenon for many years. In this work, structure-activity relationships were established from various triterpene saponins distinguishing hemolytic activity between mono- and bidesmosidic saponins. Saponins structure in Sapindaceae serve as a chimiotaxonomic criteria for dividing the species into two sub-families. In order to verify this criteria, five species were studied: Smelophyllum capense and Dimocarpus fumatus from the sub-family Sapindoideae, Filicium decipiens, Hippobromus pauciflorus, and Harpullia cupanioides from the sub-family Dodonaeoideae. Structure of eleven new saponins were elucidated from four species by the study of homo- and heteronuclear advanced NMR experiments and MS. Other metabolites were also isolated from Dimocarpus fumatus, including isoprenypchromenes and three new glycosides of long chain fatty alcohols.
Subject(s)
Glycosides/pharmacology , Hemolysis/drug effects , Sapindaceae/chemistry , Saponins/pharmacology , Carbohydrate Sequence , Glycosides/isolation & purification , Humans , In Vitro Techniques , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Sequence Data , Saponins/isolation & purification , Species SpecificityABSTRACT
The isolation and spectral data of three saponins from the roots of Chenopodium album L. are reported. One of them is a seco-glycoside analogous to compounds that were previously found in species belonging to Caryophyllales.
Subject(s)
Chenopodiaceae , Plants, Medicinal , Saponins/chemistry , Triterpenes/chemistry , Humans , Plant Extracts/chemistryABSTRACT
The ethanolic extract from the stem bark of Dimocarpus fumatus, showed in vitro cytotoxic activity against KB cells. Fractionation of the extract gave compounds belonging to different classes. The two major components have been identified as a benzoquinone, sargaquinone, and a chromene, sargaol. One sphingolipid, soyacerebroside I, two glycosides of sitosterol, and fatty acids were also identified. Besides these known compounds, two new glycosides of long-chain fatty alcohols have been identified as 1-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D- glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->6)-beta-D- glucopyranosyl]hexadecanol and 1-O-[[alpha-L-arabinopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1 -->2)- beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->6)-beta-D- glucopyranosyl] hexadecanol, and a mixture of three new diacylglycerylglucosides has been isolated. These structures were elucidated by analysis of 2D-NMR and mass spectra.
Subject(s)
Antineoplastic Agents, Phytogenic/chemistry , Glycosides/chemistry , Oligosaccharides/chemistry , Trees , Animals , Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/toxicity , Carbohydrate Conformation , Carbohydrate Sequence , Cell Survival/drug effects , Glycosides/isolation & purification , Glycosides/toxicity , Humans , KB Cells , Leukemia P388 , Mice , Models, Molecular , Molecular Sequence Data , Oligosaccharides/isolation & purification , Oligosaccharides/toxicity , Plant Stems , Tumor Cells, CulturedABSTRACT
Four new saponins have been isolated from the stem bark of Filicium decipiens and identified as 3-O-{beta-D-glucopyranosyl(1-->2)-beta- D-glucopyranosyl}-28-O-{[alpha-L-arabinopyranosyl(1-->2)-beta- D-xylopyranosyl (1-->6)]. [4-O-angeloyloxy-alpha-L-arabinopyranosyl(1-->2)-alpha-L- rhamnopyranosyl(1-->2)]}-beta-D-glucopyranosyl gypsogenic acid, 3-O-{beta-D-glucopyranosyl(1-->2)-beta-D- glucopyranosyl}-28-O-{[alpha-L-arabinopyranosyl(1-->2)- beta-D-xylopyranosyl(1-->6)] [4-O-angeloyloxy-alpha-L- arabinopyranosyl(1-->2)-alpha-L-rhamnopyranosyl(1-->2)]}-beta-D- glucopyranosyl medicagenic acid, 3-O-{beta-D-glucopyranosyl(1-->2)-beta-D- glucopyranosyl}-28-O-{[alpha-L-arabinopyranosyl(1-->2)] [beta-D-xylopyranosyl(1-->4)]alpha-L-rhamnopyranosyl(1-->2)-4-O-[3'- hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy++ +]-beta-D- fucopyranosyl} medicagenic acid and 3-O-beta-D-glucopyranosyl-28-O- {[alpha-L-arabinopyranosyl(1-->2)] [beta-D-xylopyranosyl(1-->4)] alpha-L-rhamnopyranosyl(1-->2)-4- O-[(3'-hydroxy-2'-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyro yloxy]-beta- D-fucopyranosyl} zanhic acid. These structures were elucidated by analysis of 2D-NMR spectra and of electrospray ionization mass spectra.
Subject(s)
Saponins/chemistry , Trees , Carbohydrate Sequence , Molecular Conformation , Molecular Sequence Data , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Stems/chemistry , Saponins/isolation & purification , Spectrometry, Mass, Secondary Ion , Structure-Activity RelationshipABSTRACT
Five new saponins have been isolated from the stem bark of Harpullia cupanioides and identified as 3-O-beta-D-glucopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 22-O-angeloyl-A1-barrigenol, 3-O-beta-D-glucopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 28-O-angeloyl-A1-barrigenol, 3-O-beta-D-galactopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 28-O-angeloyl-A1-barrigenol. 3-O-beta-D-galactopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 16-O-beta, beta-dimethylacryloyl-camelliagenin A and 3-O-beta-D-glucopyranosyl(1-->2)[alpha-L-rhamnopyranosyl(1-->3)] beta-D-glucuronopyranosyl 28-O-angeloyl-camelliagenin A. The structures were elucidated by analysis of 2D-NMR spectra and mass spectra.