Lipophilization of Ascorbic Acid: A Monolayer Study and Biological and Antileishmanial Activities

Ascorbyl lipophilic derivatives (Asc-C2 to Asc-C18:1) 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 est...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 2014-09, Vol.62 (37), p.9118-9127
Main Authors: Kharrat, Nadia, Aissa, Imen, Sghaier, Manel, Bouaziz, Mohamed, Sellami, Mohamed, Laouini, Dhafer, Gargouri, Youssef
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents
antibacterial properties
antioxidant activity
Antioxidants
Ascorbic Acid
Ascorbic Acid - chemistry
Ascorbic Acid - metabolism
Ascorbic Acid - pharmacology
Emulsifying Agents
Esterification
Esters
Esters - chemistry
Esters - metabolism
ethanol
fatty acid esters
Fatty Acids
Fatty Acids - metabolism
Leishmania infantum
Leishmania infantum - drug effects
Leishmania major
Life Sciences
Lipase
Lipase - metabolism
Lipids
long chain fatty acids
Microbial Sensitivity Tests
Microbiology and Parasitology
oxidation
parasites
phospholipids
Protistology
silica
Staphylococcus
Staphylococcus - enzymology
Staphylococcus xylosus
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Ascorbyl lipophilic derivatives (Asc-C2 to Asc-C18:1) 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-C18:1 exhibited antileishmanial activities. The interaction of ascorbyl esters with a phospholipid monolayer showed that only medium and unsaturated long chain (Asc-C10 to Asc-C18:1) 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.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf5029398