title: 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.).
authors.affiliation: Dipartimento di Scienze della Vita e Biotecnologie, Università di Ferrara, Via L. Borsari 46, IT-44121 Ferrara (phone +39 0532 455700; fax +39 0532 455715).
authors.forename: Maria Gabriela
authors.initials: MG
authors.lastname: Moreno Rueda
authors.forename: Alessandra
authors.initials: A
authors.lastname: Guerrini
authors.forename: Pier Paolo
authors.initials: PP
authors.lastname: Giovannini
authors.forename: Alessandro
authors.initials: A
authors.lastname: Medici
authors.forename: Alessandro
authors.initials: A
authors.lastname: Grandini
authors.forename: Gianni
authors.initials: G
authors.lastname: Sacchetti
authors.forename: Paola
authors.initials: P
authors.lastname: Pedrini
mesh_terms: D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D000081008:Bicyclic Monoterpenes; D001711:Biotransformation; D002957:Citrus / Q000382:microbiology*; D004484:Ecuador; D005638:Fruit / Q000382:microbiology; D005658:Fungi / Q000302:isolation & purification / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; C035127:sabinene; C018584:linalool; C108217:citronellal
keywords: Biotranformations; Citronellal; Citrus species; Fungi; Fusarium species; Linalool; Penicillium species; Sabinene