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BIBTEX RIS

Síntese e avaliação da atividade fitotóxica de derivados da α-Santonina

2009; Brazilian Chemical Society; Volume: 32; Issue: 2 Linguagem: Inglês

10.1590/s0100-40422009000200025

ISSN

1678-7064

Autores

Elson S. Alvarenga, Luiz C. A. Barbosa, William Argolo Saliba, Francisco F. P. Arantes, Antônio J. Demuner, A.A. Silva,

Tópico(s)

Phytochemical compounds biological activities

Resumo

THE PHYTOTOXIC ACTIVITY OF α-SANTONIN DERIVATIVES.Mixtures of α-Santonin and various solvents were irradiated by either high or low pressure mercury lamps.The photochemical reactions afforded lumisantonin (11) (76% in acetonitrile), (3S,3aS,9bS)-3,6,6-trimethyl-3,3a,4,5-tetrahydronafto[1,2-b]furan-2,7(6H,9bH)dione (12) (100% in acetonitrile), 10α-acetoxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (8) (26% in acetic acid), 10α-hydroxy-3-oxo-1,7αH,6,11βHguaia-4-en-6,12-olide (10) (32%) and (E)-3-((3S,3aS,7aS)-3-methyl-2-oxo-6-(propan-2-ylidene)hexahydrobenzofuran-7-(7aH)ylidene)propanoic acid (9) (44%) (in water/ acetic acid 1:1, v/v).Lactone 12 was also prepared by irradiation of lumisantonin in diethyl ether.Lactones 8 and 10 were converted, respectively, into the 10α-acetoxy-3β-hydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (13) (87%) and 3β,10α-dihydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (14) (75%) by sodium borohydride reduction.The effects of the compounds on the development of radicle of Sorghum bicolor and Cucumis sativus were evaluated.

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