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A Novel Approach for Microbial Synthesis of Enantiomerically Pure Whisky Lactones Based on Solid-State Fermentation. 2018

Filip Boratyński, and Ewa Szczepańska, and Aleksandra Grudniewska, and Bartłomiej Skalny, and Teresa Olejniczak
Department of Chemistry, Wroclaw University of Environmental and Life Sciences, 50-375 Wrocław, Poland. filip.boratynski@upwr.edu.pl.

In this study, solid-state fermentation (SSF) was proposed as an alternative approach to obtain optically pure forms of one of the most common aroma compounds, whisky lactone. Filamentous fungi were used for enantioselective hydrolysis of a racemate of trans and cis whisky lactones, utilizing rapeseed cake as a growth medium. Among the tested fungi, Fusarium oxysporum AM13 and Papularia rosea AM17 were chosen for further studies. Various process parameters, including temperature, moisture content of solid media, and substrate concentration were optimized to maximize the efficiency of the kinetic resolution process. After optimization of the culture conditions (33 °C temperature, 60% moisture content, and substrate concentration of 3 mg/g oilseed cake), F. oxysporum AM13 resolved a mixture of trans-(+)-(4S,5R) and cis-(+)-(4R,5R) whisky lactones with enantiomeric excess (ee), ee > 99% and ee = 98%, respectively. This study presents an inexpensive and environmentally friendly method for the production of enantiomerically pure aroma lactones via the solid-state fermentation of oilseed cake. The results revealed that SSF is an effective method for acquiring highly valued and industrially demanded compounds with negligible economic cost.

UI MeSH Term Description Entries
D007783 Lactones Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure. Large cyclic lactones of over a dozen atoms are MACROLIDES. Lactone
D005285 Fermentation Anaerobic degradation of GLUCOSE or other organic nutrients to gain energy in the form of ATP. End products vary depending on organisms, substrates, and enzymatic pathways. Common fermentation products include ETHANOL and LACTIC ACID. Fermentations
D005658 Fungi A kingdom of eukaryotic, heterotrophic organisms that live parasitically as saprobes, including MUSHROOMS; YEASTS; smuts, molds, etc. They reproduce either sexually or asexually, and have life cycles that range from simple to complex. Filamentous fungi, commonly known as molds, refer to those that grow as multicellular colonies. Fungi, Filamentous,Molds,Filamentous Fungi,Filamentous Fungus,Fungus,Fungus, Filamentous,Mold
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D000434 Alcoholic Beverages Drinkable liquids containing ETHANOL. Alcoholic Beverage,Beverage, Alcoholic,Beverages, Alcoholic
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D029741 Brassica rapa A subspecies of Brassica that includes rape mustard. It is cultivated for the seed and used as animal feed. Field Mustard,Wild Rutabaga,Wild Turnip,Field Mustards,Mustard, Field,Mustards, Field,Rutabaga, Wild,Rutabagas, Wild,Turnip, Wild,Turnips, Wild,Wild Rutabagas,Wild Turnips

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