Biotransformations of terpenes by fungi from Amazonian citrus plants

Abstract

The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The more active strains have been characterized, and they belong to the genus Penicillium and Fusarium. Different biotransformation products have been obtained depending on fungi and substrates. (RS)-Linalool (1) afforded the (E)- and (Z)-furanlinalool oxides (7 and 8, resp.; 39 and 37% yield, resp.) with Fusarium sp. (1D2), 6-methylhept-5-en-2-one (4; 49%) with F. fujikuroi, and 1-methyl-1-(4-methypentyl)oxiranemethanol (6; 42%) with F. concentricum. (S)-Citronellal (2) gave (S)-citronellol (12; 36-76%) and (S)-citronellic acid (11; 5-43%) with Fusarium species, while diastereoisomeric p-menthane-3,8-diols 13 and 14 (20 and 50% yield, resp.) were obtained as main products with Penicillium paxilli. Finally, both Fusarium species and P. paxilli biotransformed sabinene (3) to give mainly 4-terpineol (19; 23-56%), and (Z)- and (E)-sabinene hydrates (17 (3-21%) and 18 (11-17%), resp.).

Keywords: Biotranformations; Citronellal; Citrus species; Fungi; Fusarium species; Linalool; Penicillium species; Sabinene.