RRC ID 60115
Author Sakakura A, Pauze M, Namiki A, Funakoshi-Tago M, Tamura H, Hanaya K, Higashibayashi S, Sugai T.
Title Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides.
Journal Biosci Biotechnol Biochem
Abstract Fatty acid monoesters of hydroxytyrosol [2-(3,4-dihydroxyphenyl)ethanol] were synthesized in two steps from tyrosol (4-hydroxyphenylethanol) by successive Candida antarctica lipase B-catalyzed chemoselective acylation on the primary aliphatic hydroxy group over phenolic hydroxy group in tyrosol, and 2-iodoxybenzoic acid (IBX)-mediated hydroxylation adjacent to the remaining free phenolic hydroxy group. Examination of their suppression effects on nitric oxide production stimulated by lipopolysaccharides in RAW264.7 cells showed that hydroxytyrosol butyrate exhibited the highest inhibition (IC50 7.0 μM) among the tested compounds.
Volume 83(2)
Pages 185-191
Published 2019-2-1
DOI 10.1080/09168451.2018.1530970
PMID 30319060
MeSH Acylation Animals Carbon-13 Magnetic Resonance Spectroscopy Esters / chemical synthesis* Esters / chemistry Esters / pharmacology Fungal Proteins / metabolism* Hydroxylation Inhibitory Concentration 50 Lipase / metabolism* Lipopolysaccharides / pharmacology* Mice Nitric Oxide / antagonists & inhibitors* Nitric Oxide / biosynthesis* Phenylethyl Alcohol / analogs & derivatives* Phenylethyl Alcohol / chemical synthesis Phenylethyl Alcohol / chemistry Phenylethyl Alcohol / pharmacology Proton Magnetic Resonance Spectroscopy RAW 264.7 Cells Spectrometry, Mass, Electrospray Ionization
IF 1.297
Times Cited 2
Human and Animal Cells RAW 264(RCB0535)