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Biotransformation of (+)-isofraxinellone by Aspergillus niger and insect antifeedant activity |
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| Authors: | Yoshiharu Okuno Shinsuke Marumoto Jun Tsurumi |
| Affiliation: | 1. Department of Applied Chemistry and Biochemistry, National Institute of Technology, Wakayama Collage, Gobo-shi, Japan;2. Joint Research Centre, Kindai University (Former name :Kinki University), Higashiosaka-shi, Japan;3. Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, Japan |
| Abstract: | The biotransformation of (+)-isofraxinellone (1) by Aspergillus niger was investigated. Compound 1 was transformed to only one new compound 2. The structure of 2 was identified as (-)-(4S)-4-hydroxyisofraxinellone which was regio- and stereo-selective hydroxylated at the C-4 position by IR, EI-MS 1D and 2D NMR. Absolute configuration of hydroxyl group at the C-4 position was detected by modified Mosher’s method. Antifeedant activity of compounds 1 and 2 against larvae of Spodoptera litura was assayed. These compounds showed potent antifeedant activity and ED50 (50% of effective dose) values were 3.91 and 4.43 μg/cm2, respectively. |
| Keywords: | (+)-isofraxinellone (4S)-4-hydroxyisofraxinellone biotransformation Aspergillus niger antifeedant Spodoptera litura |