title: Phenol esterase activity of porcine skin.
abstract: The alkyl esters of plant-derived phenols may serve as slow-release sources for cutaneous delivery of antioxidants. The ability of skin esterases to hydrolyze phenolic esters was examined. Esters of tyrosol and hydroxytyrosol were prepared from decanoic and lipoic acids. Ferulic acid was esterified with octadecanol, glycerol, and dioleoylglycerol. These phenolic derivatives were treated in taurodeoxycholate microemulsion and unilamellar liposomes with ex vivo porcine skin and an aqueous extract of the skin. Extracted esterases hydrolyzed the microemulsions at rates in the order: tyrosyl lipoate > tyrosyl decanoate > hydroxytyrosyl lipoate > hydroxytyrosyl decanoate. The tyrosyl decanoate was subject to comparatively little hydrolysis (10-30% after 24h) when incorporated into liposomes, while hydroxytyrosyl decanoate in liposomes was not hydrolyzed at all by the skin extract. Ferulate esters were not hydrolyzed by the extract in aqueous buffer, microemulsion, nor liposomes. Tyrosyl decanoate applied topically to skin explants in microemulsion were readily hydrolyzed within 4h, while hydrolysis was minimal when applied in liposomes. These findings indicate that porcine skin displays a general esterase activity toward medium-chain esters of tyrosol and hydroxytyrosol, which can be moderated by the physiochemical properties of the lipid vehicle, but no feruloyl esterase activity.
authors.affiliation: Renewable Product Technology, USDA-Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA. Electronic address: Joe.Laszlo@ars.usda.gov.
authors.forename: Joseph A
authors.initials: JA
authors.lastname: Laszlo
authors.affiliation: Renewable Product Technology, USDA-Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: Leslie J
authors.initials: LJ
authors.lastname: Smith
authors.affiliation: Renewable Product Technology, USDA-Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: Kervin O
authors.initials: KO
authors.lastname: Evans
authors.affiliation: Renewable Product Technology, USDA-Agricultural Research Service, National Center for Agricultural Utilization Research, Peoria, IL, USA.
authors.forename: David L
authors.initials: DL
authors.lastname: Compton
mesh_terms: D000818:Animals; D003651:Decanoates / Q000737:chemistry / Q000378:metabolism; D004655:Emulsions / Q000737:chemistry / Q000378:metabolism; D004950:Esterases / Q000737:chemistry / Q000378:metabolism*; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D006868:Hydrolysis; D008081:Liposomes / Q000737:chemistry; D019800:Phenol / Q000737:chemistry / Q000378:metabolism*; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D012867:Skin / Q000737:chemistry / Q000201:enzymology* / Q000378:metabolism*; D013552:Swine / Q000378:metabolism*
chemical_list: D003651:Decanoates; D004655:Emulsions; D004952:Esters; D008081:Liposomes; C005975:3,4-dihydroxyphenylethanol; C011867:4-hydroxyphenylethanol; D019800:Phenol; D004950:Esterases; D010626:Phenylethyl Alcohol
keywords: Antioxidant; Ferulic acid; Ferulic acid (PubChem CID 445858); Hydroxytyrosol; Hydroxytyrosol (PubChem CID 82755); Lipoic acid; Lipoic acid (PubChem CID 864); Skin penetration; Tyrosol; Tyrosol (PubChem CID 10393)