title: A Straightforward Access to New Families of Lipophilic Polyphenols by Using Lipolytic Bacteria.
abstract: The chemical synthesis of new lipophilic polyphenols with improved properties presents technical difficulties. Here we describe the selection, isolation and identification of lipolytic bacteria from food-processing industrial wastes, and their use for tailoring a new set of compounds with great interest in the food industry. These bacteria were employed to produce lipolytic supernatants, which were applied without further purification as biocatalysts in the chemoselective and regioselective synthesis of lipophilic partially acetylated phenolic compounds derived from olive polyphenols. The chemoselectivity of polyphenols acylation/deacylation was analyzed, revealing the preference of the lipases for phenolic hydroxyl groups and phenolic esters. In addition, the alcoholysis of peracetylated 3,4-dihydroxyphenylglycol resulted in a series of lipophilic 2-alkoxy-2-(3,4-dihydroxyphenyl)ethyl acetate through an unexpected lipase-mediated etherification at the benzylic position. These new compounds are more lipophilic and retained their antioxidant properties. This approach can provide access to unprecedented derivatives of 3,4-dihydroxyphenylglycol with improved properties.
authors.affiliation: Department of Genetics, Faculty of Biology, University of Seville, Seville, Spain.|Department of Microbiology and Parasitology, Faculty of Pharmacy, University of Seville, Seville, Spain.
authors.forename: Leyre
authors.initials: L
authors.lastname: Sánchez-Barrionuevo
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain.
authors.forename: Alejandro
authors.initials: A
authors.lastname: González-Benjumea
authors.affiliation: Department of Genetics, Faculty of Biology, University of Seville, Seville, Spain.|Department of Microbiology and Parasitology, Faculty of Pharmacy, University of Seville, Seville, Spain.
authors.forename: Almudena
authors.initials: A
authors.lastname: Escobar-Niño
authors.affiliation: Department of Microbiology and Parasitology, Faculty of Pharmacy, University of Seville, Seville, Spain.
authors.forename: María Teresa
authors.initials: MT
authors.lastname: García
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain.
authors.forename: Óscar
authors.initials: Ó
authors.lastname: López
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain.
authors.forename: Inés
authors.initials: I
authors.lastname: Maya
authors.affiliation: Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain.
authors.forename: José G
authors.initials: JG
authors.lastname: Fernández-Bolaños
authors.affiliation: Department of Genetics, Faculty of Biology, University of Seville, Seville, Spain.
authors.forename: David
authors.initials: D
authors.lastname: Cánovas
authors.affiliation: Department of Microbiology and Parasitology, Faculty of Pharmacy, University of Seville, Seville, Spain.
authors.forename: Encarnación
authors.initials: E
authors.lastname: Mellado
mesh_terms: D000215:Acylation; D001419:Bacteria / Q000378:metabolism*; D055162:Biocatalysis; D001713:Biphenyl Compounds / Q000378:metabolism; D002175:Candida / Q000201:enzymology; D004951:Esterification; D016166:Free Radical Scavengers / Q000378:metabolism; D062385:Hydroxybenzoates / Q000378:metabolism; D008049:Lipase / Q000378:metabolism; D008066:Lipolysis; D008734:Methoxyhydroxyphenylglycol / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D010802:Phylogeny; D010851:Picrates / Q000378:metabolism; D059808:Polyphenols / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D062385:Hydroxybenzoates; D010851:Picrates; D059808:Polyphenols; C005975:3,4-dihydroxyphenylethanol; C009091:protocatechuic acid; D008734:Methoxyhydroxyphenylglycol; C004931:1,1-diphenyl-2-picrylhydrazyl; D008049:Lipase; D010626:Phenylethyl Alcohol; C010117:3,4-dihydroxyphenylglycol