Benzopyrans from Curvularia sp., an endophytic fungus associated with Ocotea corymbosa (Lauraceae).
An isolate of Curvularia sp. was obtained from the leaves of Ocotea corymbosa, a native plant of the Brazilian Cerrado. The ethyl acetate extract from culture of this fungus afforded two benzopyran derivatives: (2'S)-2-(propan-2'-ol)-5-hydroxy-benzopyran-4-one (2) and 2,3-dihydro-2-methyl-benzopyran-4,5-diol (4); and two known benzopyrans: 2-methyl-5-methoxy-benzopyran-4-one (1) and (2R)-2,3-dihydro-2-methyl-5-methoxy-benzopyran-4-one (3). The structures of 2 and 4 were established on the basis of comprehensive spectroscopic analysis, mainly using 1D and 2D NMR experiments. The benzopyrans 1 and 2 showed weak in vitro antifungal activity against Cladosporium sphaerospermum and C. cladosporioides. Analyses of the biological activities were also carried out on HeLa (human cervix tumor) and CHO (Chinese hamster ovary) cells, aiming to evaluate their potential effects on mammalian cell line proliferation. Results from both cell lines indicated that compound 2 was able to induce cell proliferation: 70% on HeLa cells and 25% on CHO cells.
Teles
Helder Lopes
HL
NuBBE-Núcleo de Bioensaio, Biossíntese e Ecofisiologia de Produtos Naturais, Instituto de Química, Universidade Estadual Paulista, CP 355, CEP 14801-970, Araraquara, SP, Brazil.
Silva
Geraldo Humberto
GH
Castro-Gamboa
Ian
I
Bolzani
Vanderlan da Silva
Vda S
Pereira
José Odair
JO
Costa-Neto
Claudio Miguel
CM
Haddad
Renato
R
Eberlin
Marcos Nogueira
MN
Young
Maria Claudia Marx
MC
Araújo
Angela Regina
AR
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry* / Q000254:growth & development; D001578:Benzopyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D006224:Cricetinae; D003412:Cricetulus; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D027444:Ocotea / Q000382:microbiology*
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001578:Benzopyrans