RESUMO
Saponins with an aldehyde function bound at C-4 from different plant origins increase the cytotoxicity of the lectin agrostin by enhancing its penetration through the cell membrane. Experiments with different pure saponins in combination with agrostin showed that also the glycosidic part of acidic bisdesmosidic saponins especially the oligosaccharidic ester chain at C-28 plays an important role in the potentiation of agrostin's cytotoxicity as result of an interaction between saponins and lectins at the cell membrane.
Assuntos
Proteínas de Plantas/toxicidade , Saponinas/química , Saponinas/farmacologia , Antineoplásicos/metabolismo , Antineoplásicos/toxicidade , Linhagem Celular Tumoral , Humanos , Estrutura Molecular , Proteínas de Plantas/metabolismo , Proteínas Inativadoras de Ribossomos Tipo 1 , Relação Estrutura-AtividadeRESUMO
A novel triterpene saponin, 3-Osulfate-gypsogenic acid-23-O-beta-D-4-O-sulfate-glucopyranoside (junceoside D), has been isolated from the roots of Arenaria juncea. The structure was characterized mainly by a combination of 2D-NMR techniques, mass spectrometry and chemical methods.
Assuntos
Caryophyllaceae/química , Saponinas/química , Triterpenos/química , Espectroscopia de Ressonância Magnética , Extratos Vegetais , Raízes de Plantas/química , Saponinas/isolamento & purificação , Saponinas/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Triterpenos/farmacologiaRESUMO
Three new triterpenoid saponins, 1-3, were isolated from the roots of Acanthophyllum squarrosum. Their structures were established mainly by 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-3-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-3,4-di-O-acetyl-beta-D-fucopyranoside (1), 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl-gypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[5-O-acetyl-alpha-L-arabinofuranosyl-(1-->3)]-4-O-acetyl-beta-D-fucopyranoside (2), and 3-O-beta-D-glucopyranosyl-quillaic acid-28-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (3).
Assuntos
Ácido Oleanólico/análogos & derivados , Plantas/química , Saponinas/isolamento & purificação , Terpenos/isolamento & purificação , Triterpenos/isolamento & purificação , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Dados de Sequência Molecular , Estrutura Molecular , Raízes de Plantas/química , Saponinas/química , Terpenos/química , Triterpenos/químicaRESUMO
Three novel triterpenoid saponins, junceosides A (1), B (2), and C (3), together with two known saponins have been isolated from the roots of Arenaria juncea. Their structures were elucidated using a combination of homo- and heteronuclear 2D NMR techniques (COSY, TOCSY, NOESY, HSQC, and HMBC) and by FABMS. The new compounds were characterized as 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-glucopyranosyl(1-->3)-[beta-D-xylopyranosyl-(1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (1), 3-O-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (2), and 3-O-beta-D-xylopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranoside (3).
Assuntos
Caryophyllaceae/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Ácido Oleanólico/análogos & derivados , Plantas Medicinais/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Fenômenos Químicos , Físico-Química , Cromatografia em Camada Fina , Medicamentos de Ervas Chinesas/química , Hidrólise , Estrutura Molecular , Raízes de Plantas/química , Saponinas/química , Espectrofotometria Infravermelho , Triterpenos/químicaRESUMO
Two novel triterpenoid saponins (1 and 2) have been isolated from the roots of Acanthophyllum squarrosum. The structures were established mainly by a combination of 2D NMR techniques as 3-O-beta-D-galactopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-be ta-D-glucuronopyranosylgypsogenin-28-O-beta-D-xylopyranosyl-(1-->3 )-b eta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L- rhamnopyranosyl-(1-->3)]-beta-D-fucopyranoside (1) and 3-O-beta-D-glucopyranosylgypsogenin-28-O-alpha-L-rhamnopyranosyl-( 1-- >2)-alpha-L-arabinopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6 )]- beta-D-glucopyranoside (2). Compound 1 showed a moderate concentration-dependent immunomodulatory effect in an in vitro lymphocyte proliferation assay.
Assuntos
Adjuvantes Imunológicos/isolamento & purificação , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/isolamento & purificação , Plantas Medicinais/química , Saponinas/isolamento & purificação , Adjuvantes Imunológicos/farmacologia , Sequência de Carboidratos , Divisão Celular/efeitos dos fármacos , Hidrólise , Linfócitos/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Ácido Oleanólico/farmacologia , Extratos Vegetais/análise , Raízes de Plantas/química , Saponinas/farmacologia , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria InfravermelhoRESUMO
Foetidissimoside B (1), a novel triterpene saponin, was isolated from the roots of Cucurbita foetidissima. Based on spectroscopic data, especially direct and long-range heteronuclear 2D NMR analysis and on chemical transformations, the structure of 1 was elucidated as 3-O-beta-D-glucuronopyranosyl-echinocystic acid 28-O-beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranosyl(1-->3)-[beta- D-xylopyranosyl (1-->4)]-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside . Compound 1 did not show any ability to potentiate in vitro cisplatin cytotoxicity in a human colon cancer cell line.
