Artigo
Unusual C,O-fused glycosylapigenins from Serjania marginata leaves
Registro en:
Journal of Natural Products, v. 78, n. 1, p. 77-84, 2014.
0163-3864
10.1021/np500715x
7927877224326837
0000-0003-3032-2556
Autor
Heredia-Vieira, Silvia Cristina [UNESP]
Simonet, Ana Maria Morales
Vilegas, Wagner [UNESP]
Macías, Francisco Antonio
Resumen
A phytochemical study of a Serjania marginata leaf extract with antiulcer activity afforded 15 compounds, including the new 3-O-α-l-arabinopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)[β-d-glucopyranosyl(1→4)]-α-l-arabinopyranosyloleanolic acid (1) and 7,5″-anhydroapigenin 8-C-α-(2,6-dideoxy-5-hydroxy-ribo-hexopyranosyl)-4′-O-β-d-glucopyranoside (4). The structures of the new compounds were determined by spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Compound 4 is a C-hexopyranosylapigenin with an unusual cyclic ether linkage between C-5″ and C-7 of apigenin. The isolated proanthocyanidins have high antioxidant activities, and these compounds are probably responsible for the gastroprotective effect of the extract. Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) Universidade Estadual Paulista Júlio de Mesquita Filho, Campus do Litoral Paulista - Unidade São Vicente, São Vicente, Praça Infante Dom Henrique sn, Parque Bitarú, CEP 11330900, SP, Brasil Universidade Estadual Paulista Júlio de Mesquita Filho, Faculdade de Ciências Farmacêuticas de Araraquara Universidade Estadual Paulista Júlio de Mesquita Filho, Campus do Litoral Paulista - Unidade São Vicente FAPESP 2009/52237-9 FAPESP 2011/08880-4 CAPES 17995/12-4