Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus Botrytis cinerea

Abstract

Indanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives exhibiting antifungal activity against the phytopathogenic fungus Botrytis cinerea were prepared using biocatalytic methods. As a result of the biotransformation of racemic 6-chloroindanol (1) and 5-chloroindanol (2) by the fungus B. cinerea, the compounds anti-(+)-6-chloroindan-1,2-diol (anti-(+)-7), anti-(+)-5-chloroindan-1,3-diol (anti-(+)-8), syn-(+)-5-chloroindan-1,3-diol (syn-(+)-8), syn-(-)-5-chloroindan-1,3-diol (syn-(-)-8), and anti-(+)-5-chloroindan-1,2-diol (anti-(+)-9) were isolated for the first time. These products were characterized by spectroscopic techniques and their enantiomeric excesses studied by chromatographic techniques. The results obtained in the biotransformation seem to suggest that the fungus B. cinerea uses oxidation reactions as a detoxification mechanism.

Bio-Guided Isolation of New Compounds from Baccharis spp. as Antifungal against Botrytis cinerea

“…The fungicidal properties of most active compounds, 5 and 10, were assessed by the "poisoned food" technique (Figures S28 and S29) [41]. The bioassay was carried out by measuring radial growth inhibition on an agar medium in a Petri dish in the presence of test compounds at 28 • C. The test compound was dissolved in ethanol, resulting in a final compound concentration of 0.06-30 µg/mL.…”

A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity

“…On the other hand, microbial transformations have advantages over conventional organic synthesis due to their high stereo- and regioselectivity under mild reaction conditions [ 32 , 33 , 34 , 35 ]. In the literature, there are few examples of microbial transformations of lathyrane-type compounds involving regioselective hydroxylations, glycosylations, deoxygenations, and cyclopropane ring openings [ 36 , 37 , 38 ].…”