Stereochemical Characterization of Optically Active Indane and Phenylpropyl Derivatives Obtained Through Biotransformation by the Marine-Derived Fungi <i>Emericellopsis maritima</i> BC17 and <i>Purpureocillium lilacinum</i> BC17-2
Jorge R. Virués-Segovia | Salvador Muñoz-Mira | Nuria Cabrera-Gómez | Marta Pacheco | María Gómez-Marín | Javier Moraga | Rosa Durán-Patrón | Josefina Aleu
Indane and phenylpropyl derivatives are interesting precursors for the synthesis of bioactive compounds, including those with antifungal or anti-inflammatory properties. In light of the increasing interest in the biocatalytic potential of marine-derived fungi, a study was conducted in which the substrates indene (<b>1</b>), indanone (<b>2</b>), 5-chloroindanone (<b>2a</b>), 1-phenylpropyl acetate (<b>3</b>), and 1-(4′-chlorophenyl)propyl acetate (<b>3a</b>) were biotransformed by the marine sediment-derived fungal strains <i>Purpureocillium lilacinum</i> BC17-2 and <i>Emericellopsis maritima</i> BC17. Fermentations led to the isolation of sixteen derivatives, which exhibited noteworthy stereoselectivities. The absolute configurations of the optically active indane and phenylpropyl derivatives isolated were determined through electronic circular dichroism and optical rotation dispersion computational calculations. Furthermore, given the known biocatalytic potential of the phytopathogenic fungus <i>Botrytis cinerea</i> to modify the structures of certain antifungal phenylpropyl derivatives, substrates 3 and 3a were also subjected to biotransformation by the strain <i>B. cinerea</i> UCA992. The antifungal activities of the biotransformation products <b>(<i>R</i>)-5</b>, <b>(<i>S</i>)-6</b>, <b><i>syn</i>-(1<i>S</i>,2<i>R</i>)-7</b>, <i><b>anti</b></i><b>-(1<i>R</i>,2<i>R</i>)-7</b>, <b>(<i>R</i>)-8</b>, <b>(<i>R</i>)-9</b>, <b><i>threo</i>-(1<i>R</i>,2<i>R</i>)-11</b>, and <b><i>erythro</i>-(1<i>R</i>,2<i>S</i>)-11</b> were evaluated against <i>B. cinerea</i> UCA992 using a resazurin-based microdilution method.
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