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Chemical Constituents of Papulaspora immersa , an Endophyte from Smallanthus sonchifolius (Asteraceae), and Their Cytotoxic Activity
Author(s) -
Borges Coutinho Gallo Margareth,
Coêlho Cavalcanti Bruno,
Washington Araújo Barros Francisco,
Odorico de Moraes Manoel,
Veras CostaLotufo Letícia,
Pessoa Cláudia,
Kenupp Bastos Jairo,
Tallarico Pupo Mônica
Publication year - 2010
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201000011
Subject(s) - chemistry , asteraceae , stereochemistry , chromone , endophyte , tyrosol , cordycepin , traditional medicine , botany , biochemistry , phenols , medicine , biology
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, (22 E ,24 R )‐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 (24 R )‐stigmast‐4‐en‐3‐one ( 1 ), 24‐methylenecycloartan‐3 β ‐ol ( 2 ), (22 E ,24 R )‐ergosta‐4,6,8(14),22‐tetraen‐3‐one ( 3 ), (−)‐(3 R ,4 R )‐4‐hydroxymellein ( 5 ), (−)‐(3 R )‐5‐hydroxymellein ( 6 ), 6,8‐dihydroxy‐3‐methylisocoumarin ( 7 ), (−)‐(4 S )‐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 IC 50 values of 3.3, 14.7, 5.0 and 1.6 μ M , respectively. Strong synergistic effects were also observed with compound 5 and some of the isolated steroidal compounds.