Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

Abstract

Fermentation broths of Ashbya gossypii from the industrial production of riboflavin emit an intense floral, fruity, and nutty smell. Typical Ehrlich pathway products, such as 2-phenylethan-1-ol and 2-/3-methylbutan-1-ol, were detected in large amounts as well as some intensely smelling saturated and unsaturated lactones, e.g., γ-decalactone and γ-(Z)-dodec-6-enlactone. An aroma extract dilution analysis identified 2-phenylethan-1-ol and γ-(Z)-dodec-6-enlactone as the main contributors to the overall aroma, with flavor dilution factors of 32 768. The position of the double bonds of unsaturated lactones was determined by the Paternò-Büchi reaction, and reference compounds that were not available commercially were synthesized to elucidate the structures of the uncommon lactones. The absolute configuration and enantiomeric excess values of the lactones were determined by converting the lactones to their corresponding Mosher's esters. In addition, the odor impressions and odor thresholds in air were determined.

Keywords: Ashbya gossypii; Paternò−Büchi reaction; flavor; unsaturated lactones.