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

Ayaka Sakakura, Martin Pauze, Atsuhiro Namiki, Megumi Funakoshi-Tago, Hiroomi Tamura, Kengo Hanaya, Shuhei Higashibayashi, Takeshi Sugai

Research output: Contribution to journalArticle

2 Citations (Scopus)

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 (IC 50 7.0 μM) among the tested compounds.

Original languageEnglish
Pages (from-to)185-191
Number of pages7
JournalBioscience, Biotechnology and Biochemistry
Volume83
Issue number2
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • Anti-inflammatory effect
  • Chemoselective acylation
  • Fatty acid monoesters
  • Hydroxytyrosol
  • Site-selective hydroxylation

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides'. Together they form a unique fingerprint.

  • Cite this