Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants. Issue 10 (16th October 2013)

• Record Type: Journal Article
• Authors: Moreno Rueda, Maria Gabriela; Guerrini, Alessandra; Giovannini, Pier Paolo; Medici, Alessandro; Grandini, Alessandro; Sacchetti, Gianni; Pedrini, Paola
• Is Part Of: Chemistry & biodiversity. Volume 10:Issue 10(2013:Oct.)
• Page Start: 1909
• Page End: 1919
• Publication Date: 2013-10-16
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201300112
• Languages: English
• ISSNs: 1612-1872

Abstract

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