1. Triterpenoid Glycosides from Leaves of Medicago arborea L
- Author
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Pinarosa Avato, Aldo Tava, Zbigniew Bialy, Mariella Mella, Marian Jurzysta, and Maria Pia Argentieri
- Subjects
Spectrometry, Mass, Electrospray Ionization ,Stereochemistry ,Chemical structure ,Carbohydrates ,Saponin ,Spectrometry, Mass, Fast Atom Bombardment ,Hydrolysis ,Triterpene ,Medicago ,Glycosides ,Chromatography, High Pressure Liquid ,chemistry.chemical_classification ,biology ,Plant Extracts ,Chemistry ,Medicago arborea ,Glycoside ,General Chemistry ,Saponins ,Fast atom bombardment ,biology.organism_classification ,Triterpenes ,Terpenoid ,Plant Leaves ,Chromatography, Thin Layer ,General Agricultural and Biological Sciences - Abstract
Eighteen triterpene saponins (1-18) from Medicago arborea leaves have been isolated and their structures elucidated by spectroscopic, spectrometric (1D and 2D NMR, FAB-MS, ESI-MS/MS), and chemical methods. They have been identified as glycosides of medicagenic, zanhic, and 2beta-hydroxyoleanolic acids, soyasapogenol B, bayogenin, and 2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid. Twelve of them, identified as 3-O-beta-D-glucopyranosyl-28-O-[alpha-L-arabinopyranosyl(1--3)-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside] zanhic acid (3), 3-O-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1--4)-[alpha-L-arabinopyranosyl-(1--3)]-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside] zanhic acid (4), 3-O-[alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranosyl(1--2)-beta-D-glucopyranosyl]-2beta-hydroxyoleanolic acid (5), 3-O-beta-D-glucuronopyranosyl-28-O-[alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside]medicagenic acid (6), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1--4)-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside]bayogenin (9), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1--4)-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside]-2beta,3beta-dihydroxyolean-12-en-23-al-28-oic acid (10), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1--4)-[beta-D-apiofuranosyl(1--3)]-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside]zanhic acid (12), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1--4)-[alpha-L-arabinopyranoside(1--3)]-alpha-L-rhamnopyrano-syl(1--2)-alpha-L-arabinopyranoside]zanhic acid (13), 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyrano-syl(1--4)-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside]zanhic acid (14), 3-O-[alpha-L-arabinopyranosyl-(1--2)-beta-D-glucopyranosyl(1--2)-beta-D-glucopyranosyl]-28-O-[beta-D-xylopyranosyl(1--4)-[beta-D-apiofurano-syl(1--3)]-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyranoside]zanhic acid (16), 3-O-[beta-D-glucopyrano-syl(1--2)-beta-D-glucopyranosyl]-28-O-[beta-D-xylopyranosyl(1--4)-[alpha-L-arabinopyranosyl(1--3)]-alpha-L-rhamno-pyranosyl (1--2)-alpha-L-arabinopyranoside]zanhic acid (17), and 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl(1--4)-[beta-D-apiofuranosyl(1--3)]-alpha-L-rhamnopyranosyl(1--2)-alpha-L-arabinopyrano-side]medicagenic acid (18), are reported as new natural compounds. The presence of the aldehydic group on the sapogenin moiety of saponin 10 is discussed in the framework of a possible elucidation of the biosynthesis of these metabolites.
- Published
- 2005
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