title: Spirostanol glucosides from the leaves of Cestrum laevigatum L.
abstract: 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.
authors.affiliation: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, CEP 60.021-940 Fortaleza, CE, Brazil.
authors.forename: Paulo Riceli Vasconcelos
authors.initials: PR
authors.lastname: Ribeiro
authors.affiliation: Departamento de Farmacologia e Fisiologia, Faculdade de Medicina, Universidade Federal do Ceará, CP 12.200, 60430-270 Fortaleza-CE, Brazil.
authors.forename: Ana Jérsia
authors.initials: AJ
authors.lastname: Araújo
authors.affiliation: Departamento de Farmacologia, Instituto de Ciências Biomédicas, Universidade de São Paulo, CEP 05508-900 São Paulo, SP, Brazil.
authors.forename: Letícia Veras
authors.initials: LV
authors.lastname: Costa-Lotufo
authors.affiliation: Laboratório de Ciências Químicas, Universidade Estadual do Norte Fluminense Darcy Ribeiro, 28013 602 Campos dos Goytacazes, RJ, Brazil; Departamento de Química, Universidade Federal Rural do Rio de Janeiro, CP 74541, 23890-000 Seropédica, RJ, Brazil.
authors.forename: Raimundo
authors.initials: R
authors.lastname: Braz-Filho
authors.affiliation: Departamento de Farmácia, Universidade Federal do Ceará, CP 12.200, 60430-170 Fortaleza, CE, Brazil.
authors.forename: Hélio Vitoriano
authors.initials: HV
authors.lastname: Nobre Junior
authors.affiliation: Departamento de Farmácia, Universidade Federal do Ceará, CP 12.200, 60430-170 Fortaleza, CE, Brazil.
authors.forename: Cecília Rocha
authors.initials: CR
authors.lastname: da Silva
authors.affiliation: Departamento de Farmácia, Universidade Federal do Ceará, CP 12.200, 60430-170 Fortaleza, CE, Brazil.
authors.forename: João Batista
authors.initials: JB
authors.lastname: de Andrade Neto
authors.affiliation: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, CEP 60.021-940 Fortaleza, CE, Brazil.
authors.forename: Edilberto Rocha
authors.initials: ER
authors.lastname: Silveira
authors.affiliation: Departamento de Química Orgânica e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12.200, CEP 60.021-940 Fortaleza, CE, Brazil. Electronic address: mary@dqoi.ufc.br.
authors.forename: Mary Anne Sousa
authors.initials: MA
authors.lastname: Lima
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D032301:Cestrum / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D018515:Plant Leaves / Q000737:chemistry*; D013150:Spirostans / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D005960:Glucosides; D013150:Spirostans
keywords: Antifungal; Cestrum laevigatum; Cytotoxic; Solanaceae; Spirostanol glycosides