title: Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity.
abstract: Microbial transformations of two natural compounds dihydrojasmone (1) and cis-jasmone (3) in the growing cultures of selected twenty strains have been investigated. The studies have demonstrated a biocatalytic potential of tested microorganisms for the enantioselective hydroxylation of jasmonates. The substrates underwent an effective regio- and stero-selective hydroxylation at the allylic position in the cyclopentenone ring, and the corresponding optically pure keto-alcohols (2, 4) were obtained. The process of biohydroxylation depended on the composition of reaction medium. In the studied cultures, (+)-(R)-4-hydroxydihydrojasmone (2) and (+) and (-)-4-hydroxyjasmone (4a, 4b) were produced in good yields and high enantiomeric excesses. Moreover, the introduction of the hydroxy group into the molecule of jasmonate ketones 1 and 3 leads to biologically active derivatives 2 and 4 that regulate the behaviour of aphids Myzus persicae by termination of their feeding.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375, Wrocław, Poland, anna.gliszczynska@wp.pl.
authors.forename: Anna
authors.initials: A
authors.lastname: Gliszczyńska
authors.forename: Witold
authors.initials: W
authors.lastname: Gładkowski
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Dancewicz
authors.forename: Beata
authors.initials: B
authors.lastname: Gabryś
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects*; D001711:Biotransformation; D003517:Cyclopentanes / Q000378:metabolism*; D006900:Hydroxylation; D007302:Insect Repellents / Q000378:metabolism*; D008958:Models, Molecular; D015394:Molecular Structure; D054883:Oxylipins / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D007302:Insect Repellents; D054883:Oxylipins; C011006:jasmonic acid