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

研究成果: Article査読

2 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)185-191
ページ数7
ジャーナルBioscience, Biotechnology and Biochemistry
83
2
DOI
出版ステータスPublished - 2019

ASJC Scopus subject areas

  • バイオテクノロジー
  • 分析化学
  • 生化学
  • 応用微生物学とバイオテクノロジー
  • 分子生物学
  • 有機化学

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