title: Lipophilization of ascorbic acid: a monolayer study and biological and antileishmanial activities.
abstract: Ascorbyl lipophilic derivatives (Asc-C2 to Asc-C(18:1)) were synthesized in a good yield using lipase from Staphylococcus xylosus produced in our laboratory and immobilized onto silica aerogel. Results showed that esterification had little effect on radical-scavenging capacity of purified ascorbyl esters using DPPH assay in ethanol. However, long chain fatty acid esters displayed higher protection of target lipids from oxidation. Moreover, compared to ascorbic acid, synthesized derivatives exhibited an antibacterial effect. Furthermore, ascorbyl derivatives were evaluated, for the first time, for their antileishmanial effects against visceral (Leishmania infantum) and cutaneous parasites (Leishmania major). Among all the tested compounds, only Asc-C10, Asc-C12, and Asc-C(18:1) exhibited antileishmanial activities. The interaction of ascorbyl esters with a phospholipid monolayer showed that only medium and unsaturated long chain (Asc-C10 to Asc-C(18:1)) derivative esters were found to interact efficiently with mimetic membrane of leishmania. These properties would make ascorbyl derivatives good candidates to be used in cosmetic and pharmaceutical lipophilic formulations.
authors.affiliation: Laboratoire de Biochimie et de Génie Enzymatique des Lipases, ENIS, Université de Sfax , Route de Soukra, BPW 1173, 3038 Sfax, Tunisia.
authors.forename: Nadia
authors.initials: N
authors.lastname: Kharrat
authors.forename: Imen
authors.initials: I
authors.lastname: Aissa
authors.forename: Manel
authors.initials: M
authors.lastname: Sghaier
authors.forename: Mohamed
authors.initials: M
authors.lastname: Bouaziz
authors.forename: Mohamed
authors.initials: M
authors.lastname: Sellami
authors.forename: Dhafer
authors.initials: D
authors.lastname: Laouini
authors.forename: Youssef
authors.initials: Y
authors.lastname: Gargouri
mesh_terms: D000900:Anti-Bacterial Agents; D000975:Antioxidants; D001205:Ascorbic Acid / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D045703:Emulsifying Agents; D004951:Esterification; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism; D018314:Leishmania infantum / Q000187:drug effects*; D008049:Lipase / Q000378:metabolism; D008055:Lipids; D008826:Microbial Sensitivity Tests; D013210:Staphylococcus / Q000201:enzymology
chemical_list: D000900:Anti-Bacterial Agents; D000975:Antioxidants; D045703:Emulsifying Agents; D004952:Esters; D005227:Fatty Acids; D008055:Lipids; D008049:Lipase; D001205:Ascorbic Acid
keywords: antimicrobial activity; ascorbic acid; leishmanicidal activity; lipophilic derivatives; phospholipid monolayers