Biotransformation of (+)-isofraxinellone by Aspergillus niger and insect antifeedant activity. Issue 10 (19th May 2019)

• Record Type: Journal Article
• Authors: Okuno, Yoshiharu; Marumoto, Shinsuke; Tsurumi, Jun; Miyazawa, Mitsuo
• Is Part Of: Natural product research. Volume 33:Issue 10(2019)
• Page Start: 1518
• Page End: 1521
• Publication Date: 2019-05-19
• Subjects: (+)-isofraxinellone -- (4S)-4-hydroxyisofraxinellone -- biotransformation -- Aspergillus niger -- antifeedant -- Spodoptera litura; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2017.1422180
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: The biotransformation of (+)-isofraxinellone (1 ) by Aspergillus niger was investigated. Compound1 was transformed to only one new compound2. The structure of 2 was identified as (-)-(4 S )-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 compounds1 and2 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/cm 2, respectively. Abstract :