2002 Fiscal Year Final Research Report Summary
Study of Convulsive Brasiliamides from Penicillium brasilianum Batista JV-379
| Project/Area Number |
13660111
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Osaka Prefecture University |
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Principal Investigator |
FUJITA Tomoyuki Osaka Prefecture University, Applied Biological Chemistry, Assistant professor, 農学生命科学研究科, 助教授 (10238579)
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| Project Period (FY) |
2001 – 2002
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| Keywords | convulsive activity / brasiliamide / Peniclllium brasilianum Batista / soy bean paste (okara) / fungus / structure elucidation |
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| Research Abstract |
New convulsive compounds, brasiliamides A and B, were isolated by activity-guided fractionation from okara fermented with a soil isolate of Penicillium brasilianum Batista JV-379. Their structures were elucidated on the basis of spectral and chemical evidence and by X-ray crystallography of the hydrogenated product of brasiliamide B. In the ^1H- and ^<13>C-NMR spectra of brasiliamide B, the signals were complicated, all being doubled or broadened in several deuterated solvents at room temperature. The conformational change of brasiliamide B was clarified as the rotational isomerization of amide bonds in solution by NMR measurements at various temperatures. Four rotamers of brasiliamide B at two amide bonds were presented at -60℃ in CDCl_3, whereas only two isomers were apparent at room temperature, owing to rapid rotation of one of the amide bonds. Additionally, three new brasiliamides congeners, brasiliamides C, D and E were isolated and their structures were determined. Brasiliamides A, B and C respectively showed convulsive activity against silkworms with ED_<50> values of 300, 50 and 300 μg/g of diet.
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