Biohydroxylation of (−)-Ambrox®, (−)-Sclareol, and (+)-Sclareolide by Whole Cells of Brazilian Marine-Derived Fungi

Abstract

A screening was performed using nine marine-derived fungi as biocatalysts and the natural products (-)-ambrox® (1), (-)-sclareol (2), and (+)-sclareolide (3) in order to select the microorganisms able to catalyze the biooxidation of these compounds. It was observed that only the Aspergillus sydowii CBMAI 934, Botryosphaeria sp., Eutypella sp., and Xylaria sp. presented active oxidoreductases and catalyzed the regioselective hydroxylation in the natural products. The hydroxylated metabolites obtained were 1β-hydroxy-ambrox (1a) (14%, A. sydowii CBMAI 934); 3β-hydroxy-ambrox (1b) (17%, Botryosphaeria sp.; 11%, Eutypella sp.); 3β-hydroxy-sclareol (2a) (31%, Xylaria sp.; 69%, Botryosphaeria sp.; 55%, Eutypella sp.); 18-hydroxy-sclareol (2b) (10%, Xylaria sp.); and 3β-hydroxy-sclareolide (3a) (34%, Botryosphaeria sp.; 7%, Eutypella sp.). This is the first report of biohydroxylation of (-)-ambrox® (1), (-)-sclareol (2), and (+)-sclareolide (3) by whole mycelia of marine-derived fungi.

Biotransformation of methyl parathion by marine-derived fungi isolated from ascidian Didemnum ligulum

“…CBMAI 1196 and Botryosphaeria sp. CBMAI 1197), which presents CYP-450 enzymes (Martins et al, 2015).…”

Salt mine microorganisms used for the biotransformation of chlorolactones

“…The only fungal strain used as biocatalyst in the present work, A . sydowii , was able to catalyse asymmetric bioreduction of 4-methoxyacetophenone [ 37 ], hydroxylation of the natural products (–)-ambrox ® , (–)-sclareol, and (+)-sclareolide [ 38 ]; and transformation of 2-phenylacetonitrile to 2-hydroxyphenylacetic acid [ 39 ]. This strain can also degrade lignin [ 40 ] methyl parathion chlorpyrifos [ 41 , 42 ]–an important organophosphate pesticides, and 1,1-dichloro-2,2-bis-(4-chlorophenyl)ethane (DDD)–a chlorinated aromatic insecticide [ 43 ].…”

Sporochartines A–E, A New Family of Natural Products from the Marine Fungus Hypoxylon monticulosum Isolated from a Sphaerocladina Sponge

“…The selectivity of the chemical catalysis and the proportion of different isomers will be compared to the microbial counterpart. According to our expertise in biocatalysis-based chemodiversification of natural compounds (Adelin et al, 2011;Martins et al, 2015), sporothriolide will be submitted to a …”