| Project/Area Number |
16380142
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Fisheries chemistry
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| Research Institution | The University of Tokyo |
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Principal Investigator |
MATSUNAGA Shigeki The University of Tokyo, Graduate School of Agricultural and Life Sciences, Professor, 大学院農学生命科学研究科, 教授 (60183951)
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| Co-Investigator(Kenkyū-buntansha) |
OGAWA Kazuo The University of Tokyo, Graduate School of Agricultural and Life Sciences, Professor, 大学院農学生命科学研究科, 教授 (20092174)
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| Project Period (FY) |
2004 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥15,200,000 (Direct Cost: ¥15,200,000)
Fiscal Year 2006: ¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2005: ¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2004: ¥7,800,000 (Direct Cost: ¥7,800,000)
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| Keywords | tunicate / Didemnidae / Vibrio anguillarum / fish pathogenic bacteria / antimicrobial / serinolipid / structure elucidation / spectral analysis / Vibrio anguillarum / セルノリピッド / 海綿 / ホヤ / 二次元NMR / 単離 / Aeromonas hydrophila |
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| Research Abstract |
We searched for antimicrobial compounds against Vibrio anguillarum from a tunicate collected at Shishi Island. The methanol extract of the organism was subjected solvent partitioning followed by reversed phase HPLC to afford five antimicrobial compounds. The molecular formula of the major constituent shishididemniol A was shown to be C45H81N3O11 on the basis of HRFABMS. Interpretation of a variety of 2D NMR spectra showed that the compound was composed of two serinol units, a substituted octopamine, and a C28 fatty acids with six sites of oxygenation. Further analysis of the 2D NMR data in conjunction with tandem FABMS analysis allowed the assignment of the planar structure of this compound. The absolute stereochemistry of the eight stereogenic centers in the molecule was determined by application of the modified Mosher analysis to the fragments obtained by chemical degradation. Especially the stereochemistry of the isolated secondary alcohol was determined by the application of the 2-NMA method, which is a modification of the Mosher analysis. The structures of other congeners were determined in the same manner.
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