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Spirostanol glucosides from the leaves of Cestrum laevigatum L.

2015; Elsevier BV; Volume: 106; Linguagem: Inglês

10.1016/j.steroids.2015.12.006

1878-5867

Paulo Riceli Vasconcelos Ribeiro, Ana Jérsia Araújo, Letícia V. Costa‐Lotufo, Raimundo Braz‐Filho, Hélio Vitoriano Nobre Júnior, Cecília Rocha da Silva, João Batista de Andrade Neto, Edilberto R. Silveira, Mary Anne Sousa Lima,

Natural product bioactivities and synthesis

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 (6)Δ-spirostanol saponin and compound 2 has an unusual C-26 hydroxyl in the (5)Δ-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.