New Convulsive Compounds, Brasiliamides A and B, from Penicillium brasilianum Batista JV-379

作者: Tomoyuki FUJITA , Daisuke MAKISHIMA , Kohki AKIYAMA , Hideo HAYASHI

DOI: 10.1271/BBB.66.1697

关键词: Conformational changeIsomerizationPenicillium brasilianumConformational isomerismFractionationFermentationChemistryAmide bondsDeuteriumStereochemistryBiotechnologyOrganic chemistryAnalytical chemistryApplied Microbiology and BiotechnologyBiochemistryMolecular biologyGeneral Medicine

摘要: New convulsive compounds, brasiliamides A (1) and B (2), were isolated by activity-guided fractionation from okara fermented with a soil isolate of Penicillium brasilianum Batista JV-379. Their structures elucidated on the basis spectral chemical evidence X-ray crystallography hydrogenated product 2. In 1H- 13C-NMR spectra 2, signals complicated, all being doubled or broadened in several deuterated solvents at room temperature. The conformational change 2 was clarified as rotational isomerization amide bonds solution NMR measurements various temperatures. Four rotamers two presented −60°C CDCl3, whereas only isomers apparent temperature, owing to rapid rotation one bonds. Brasiliamides respectively showed activity against silkworms ED50 values 300 50 μg/g diet.

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