Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides

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 tyr...

Full description

Bibliographic Details
Published in:Bioscience, Biotechnology, and Biochemistry
Main Authors: Sakakura, Ayaka, Pauze, Martin, Namiki, Atsuhiro, Funakoshi-Tago, Megumi, Tamura, Hiroomi, Hanaya, Kengo, Higashibayashi, Shuhei, Sugai, Takeshi
Other Authors: JSPS KAKENHI, Amano Institute of Technology
Format: Article in Journal/Newspaper
Language:English
Published: Oxford University Press (OUP) 2019
Subjects:
Organic Chemistry
Molecular Biology
Applied Microbiology and Biotechnology
General Medicine
Biochemistry
Analytical Chemistry
Biotechnology
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1080/09168451.2018.1530970
http://academic.oup.com/bbb/article-pdf/83/2/185/36834427/bbb0185.pdf
Description
Summary: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.

Similar Items