Chemical constituents of Papulaspora immersa, an endophyte from Smallanthus sonchifolius (Asteraceae), and their cytotoxic activity |
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Authors: | Gallo Margareth Borges Coutinho Cavalcanti Bruno Coêlho Barros Francisco Washington Araújo Odorico de Moraes Manoel Costa-Lotufo Letícia Veras Pessoa Cláudia Bastos Jairo Kenupp Pupo Mônica Tallarico |
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Affiliation: | 1. Faculdade de Ciências Farmacêuticas de Ribeir?o Preto, Universidade de S?o Paulo, Avenida do Café, s/n, 14040‐903, Ribeir?o Preto, SP, Brazil, (phone: +55?16?36024710;2. fax: +55?16?36024178);3. Departamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, Fortaleza, CE, Brazil |
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Abstract: | Papulaspora immersa H. H. Hotson was isolated from roots and leaves of Smallanthus sonchifolius (Poepp. and Endl. ) H. Rob. (Asteraceae), traditionally known as Yacon. The fungus was cultured in rice, and, from the AcOEt fraction, 14 compounds were isolated. Among them, (22E,24R)‐8,14‐epoxyergosta‐4,22‐diene‐3,6‐dione ( 4 ), 2,3‐epoxy‐1,2,3,4‐tetrahydronaphthalene‐c‐1,c‐4,8‐triol ( 10 ), and the chromone papulasporin ( 13 ) were new secondary metabolites. The spectral data of the known natural products were compared with the literature data, and their structures were established as the (24R)‐stigmast‐4‐en‐3‐one ( 1 ), 24‐methylenecycloartan‐3β‐ol ( 2 ), (22E,24R)‐ergosta‐4,6,8(14),22‐tetraen‐3‐one ( 3 ), (?)‐(3R,4R)‐4‐hydroxymellein ( 5 ), (?)‐(3R)‐5‐hydroxymellein ( 6 ), 6,8‐dihydroxy‐3‐methylisocoumarin ( 7 ), (?)‐(4S)‐4,8‐dihydroxy‐α‐tetralone ( 8 ), naphthalene‐1,8‐diol ( 9 ), 6,7,8‐trihydroxy‐3‐methylisocoumarin ( 11 ), 7‐hydroxy‐2,5‐dimethylchromone ( 12 ), and tyrosol ( 14 ). Compound 4 showed the highest cytotoxic activity against the human tumor cell lines MDA‐MB435 (melanoma), HCT‐8 (colon), SF295 (glioblastoma), and HL‐60 (promyelocytic leukemia), with IC50 values of 3.3, 14.7, 5.0 and 1.6 μM , respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds. |
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Keywords: | Papulaspora immersa Smallanthus sonchifolius Cytotoxic activity Papulasporin Ergosta‐4,22‐diene‐3,6‐dione, 8,14‐epoxy‐ Naphthalene‐1,4,8‐triol, 2,3‐epoxy‐1,2,3,4‐tetrahydro‐ |
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