New brasiliamide congeners, brasiliamides C, D and E, from Penicillium brasilianum Batista JV-379.
Three new brasiliamide congeners, brasiliamides C, D and E, were isolated from okara fermented with Penicillium brasilianum Batista JV-379. Their structures were elucidated on the basis of spectral data and chemical evidence. NMR spectra of these brasiliamides exhibited a mixture of four or two conformers due to the restricted rotation of an amide bond in a solution. The (1)H- and (13)C-NMR spectral data were analyzed for a major rotamer at an appropriate temperature, since the signals were broadened at room temperature. Both brasiliamides C and D showed convulsive activity against silkworms with an ED(50) value of 400 microg/g of diet, whereas brasiliamide E showed less activity than the others.
Fujita
Tomoyuki
T
Division of Applied Biological Chemistry, Graduate School of Agriculture and Biological Sciences, Osaka Prefecture University, Sakai, Japan. fujita@biochem.osakafu-u.ac.jp
Hayashi
Hideo
H
D004149:Dioxoles / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry* / Q000378:metabolism; D010879:Piperazines / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D012996:Solutions
D004149:Dioxoles; D010879:Piperazines; D012996:Solutions; C494867:brasiliamide C; C494868:brasiliamide D; C494869:brasiliamide E