Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides-Reference-Cited by-同舟云学术

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

Published:2019-02-01 Issue:2 Volume:83 Page:185-191
ISSN:0916-8451
Container-title:Bioscience, Biotechnology, and Biochemistry
language:en
Short-container-title:

Author:

Sakakura Ayaka¹,Pauze Martin¹²,Namiki Atsuhiro¹,Funakoshi-Tago Megumi¹,Tamura Hiroomi¹,Hanaya Kengo¹,Higashibayashi Shuhei¹,Sugai Takeshi¹

Affiliation:

1. Faculty of Pharmacy, Keio University, Tokyo, Japan

2. Department of Chemistry, Graduate School of SIGMA Clermont, Aubiere Cedex, France

Abstract

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.

Funder

JSPS KAKENHI

Amano Institute of Technology

Publisher

Oxford University Press (OUP)

Subject

Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology

Link

http://academic.oup.com/bbb/article-pdf/83/2/185/36834427/bbb0185.pdf

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