RESUMO
From the roots of three species of Acanthophyllum (Caryophyllaceae), two new gypsogenic acid glycosides, 1 and 2, were isolated, 1 from A. sordidum and A. lilacinum, 2 from A. elatius and A. lilacinum, together with three known saponins, glandulosides B and C, and SAPO50. The structures of 1 and 2 were established mainly by 2D NMR techniques as 23-O-beta-D-galactopyranosylgypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (1) and gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-galactopyranoside (2). The cytotoxicity of several of these saponins was evaluated against two human colon cancer cell lines (HT-29 and HCT 116).
Assuntos
Caryophyllaceae/química , Ácido Oleanólico/análogos & derivados , Configuração de Carboidratos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Ácido Oleanólico/química , Especificidade da EspécieRESUMO
A phytochemical analysis of the whole plant of Allium schoenoprasum, has led to the isolation of four spirostane-type glycosides (1-4), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25S)-spirost-5-en-3ß,12ß,21-triol 3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside (1), (20S,25S)-spirost-5-en-3ß,11α,21-triol 3-O-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranoside (2), laxogenin 3-O-α-L-rhamnopyranosyl-(1â2)-[ß-D-glucopyranosyl-(1â4)]-ß-D-glucopyranoside (3), and (25R)-5α-spirostan-3ß,11α-diol 3-O-ß-D-glucopyranosyl-(1â3)-[ß-D-glucopyranosyl-(1â4)]-ß-D-galactopyranoside (4). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines.
Assuntos
Cebolinha-Francesa/química , Glicosídeos/química , Glicosídeos/toxicidade , Estruturas Vegetais/química , Sobrevivência Celular/efeitos dos fármacos , Neoplasias do Colo/tratamento farmacológico , Glicosídeos/farmacologia , Células HCT116 , Células HT29 , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Saponinas/química , Saponinas/farmacologiaRESUMO
Three oleanane-type saponins, 3-O-ß-d-glucopyranosylechinocystic acid 28-O-ß-d-xylopyranosyl-(1â4)-[α-l-rhamnopyranosyl-(1â2)]-α-l-rhamnopyranosyl ester (1), 3-O-ß-d-glucopyranosylechinocystic acid 28-O-α-l-arabinopyranosyl-(1â3)-ß-d-xylopyranosyl-(1â4)-[α-l-rhamnopyranosyl-(1â2)]-α-l-rhamnopyranosyl ester (2), 3-O-ß-d-glucopyranosylcaulophyllogenin 28-O-ß-d-apiofuranosyl-(1â3)-ß-d-xylopyranosyl-(1â4)-[ß-d-apiofuranosyl-(1â3)]-α-l-rhamnopyranosyl-(1â2)-α-l-rhamnopyranosyl ester (3) were isolated from the whole plant of Arenaria montana. Their unusual structures for the Caryophyllaceae family were established mainly by 2D NMR techniques and mass spectrometry.