Spirostanol glucosides from the leaves of Cestrum laevigatum L.

• Autor(a) principal: Ribeiro, Paulo Riceli Vasconcelos
• Data de Publicação: 2016
• Outros Autores: Araújo, Ana Jérsia, Costa-Lotufo, Letícia Veras, Braz-Filho, Raimundo, Nobre Júnior, Hélio Vitoriano, Silva, Cecília Rocha da, Andrade Neto, João Batista de, Silveira, Edilberto Rocha, Lima, Mary Anne Sousa
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da Universidade Federal do Ceará (UFC)
• Texto Completo: http://www.repositorio.ufc.br/handle/riufc/18970
• topic: Solanaceae; Glicosídeos

Two new steroidal saponins, (25R)-spirost-5-ene-3β,26β-diol 3-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 4)-[(1 → 2)-α-l-rhamnopyranosyl]-β-d-glucopyranoside (1) and (25R)-spirost-6-ene-3β,5β-diol 3-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 4)-[(1 → 2)-α-l-rhamnopyranosyl]-β-d-glucopyranoside (2), along with the known diosgenin 3-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranoside (3), chonglouoside SL-5 (4) and Paris saponin Pb (5) were isolated from the leaves of Cestrum laevigatum. The structures of the compounds were determined using spectroscopic analyses including HRESI-MS, 1D and 2D NMR data, followed by comparison with data from the literature. Among them, two are particularly unique, compound 1 is the first 6Δ-spirostanol saponin and compound 2 has an unusual C-26 hydroxyl in the 5Δ-spirostanol skeleton. Antifungal testing showed a potent activity to formosanin C against Candida albicans and Candida parapsilosis. Evaluation of the cytotoxic activity indicated that compound 1 has a moderate activity against HL-60 and SF-295 cell lines, while compound 2 were active only against HL-60.