Microbial Transformation of Isopimpinellin by Glomerella cingulata

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  • Marumoto Shinsuke
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
  • Miyazawa Mitsuo
    Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University

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Abstract

Microbial transformation studies conducted on isopimpinellin (1) by the fungus Glomerella cingulata have revealed that 1 was metabolized to give the corresponding reduced acid, 5,8-dimethoxy-6,7-furano-hydrocoumaric acid (2). The structure of metabolite 2 was elucidated by high-resolution mass spectrometry (HR-MS), extensive NMR techniques, including 1H NMR, 13C NMR, 1H-1H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteonuclear multiple bond coherence (HMBC). The biotransformed product 2 showed weak a in vitro β-secretase (BACE1) inhibitory effect.

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