Abstract

A novel microbial approach to the production of enantiomerically enriched and pure aroma compounds based on kinetic resolution via solid-state fermentation is proposed. Twenty-five filamentous fungi were screened for lipase activity and enantioselective hydrolysis of a volatile racemic ester (1-phenylethyl acetate (1)) and several racemic lactones (trans and cis whisky lactones (4, 5), γ-decalactone (7), δ-decalactone (8), (cis-3a,4,7,7a-tetrahydro-1(3H)-isobenzofuranone) (9)). Solid-state fermentation was conducted with linseed and rapeseed cakes. Kinetic resolution afforded enantiomerically enriched products with high enantiomeric excesses (ee = 82–99%). The results highlight the potential economic value of solid-state fermentation using agroindustrial side-stream feedstocks as an alternative to more expensive processes conducted in submerged fermentation.

Highlights

  • The food industry generates large quantities of wastes and by-products, and research interest in efficient use of agroindustrial residues has been increasing [1]

  • The stereoselectivity of hydrolysis catalyzed by enzymes produced by filamentous fungi in solid-state fermentation (SSF) was tested with various aroma compounds: 1-phenylethyl acetate (1), a mixture of trans and cis whisky lactones (4, 5), γ-decalactone (7), δ-decalactone (8), and cis-3a,4,7,7atetrahydro-1(3H)-isobenzofuranone (9) (Scheme 1)

  • SSF was conducted on oilseed cakes from linseeds and rapeseeds, which are by-products of the oleoindustry that contain all essential ingredients for fungal growth, especially the fatty acids that are required for lipase biosynthesis

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Summary

Introduction

The food industry generates large quantities of wastes and by-products, and research interest in efficient use of agroindustrial residues has been increasing [1]. Several bioprocesses that use these residues as substrates have been developed, including production of enzymes, single cell proteins, ethanol, organic acids, biopolymers, and secondary metabolites [2]. Constitutes a microbial culture method alternative to submerged fermentation (SmF). Because growth media account for approximately 40% of the total cost of bioprocessing, it is reasonable to use inexpensive raw materials such, as agricultural by-products [4]. Oilseed cakes are solid residues that are obtained after pressing of oil seeds. They can constitute up to 75% of total seed weight. Oilseed cakes are rich in carbohydrates, proteins, fat, and cellulose, and provide excellent media for growth of microorganisms [5]. The world market for oilseed cakes is dominated by soybean, rapeseed, cottonseed, groundnut, sunflower, and linseed cakes

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