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

Ayaka Sakakura, Martin Pauze, Atsuhiro Namiki, Megumi 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 (IC50 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

Fingerprint

Lipopolysaccharides
Nitric Oxide
Acylation
Hydroxylation
Butyrates
Inhibitory Concentration 50
Fatty Acids
4-hydroxyphenylethanol
3,4-dihydroxyphenylethanol
Candida antarctica lipase B
2-iodoxybenzoic acid

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

Cite this

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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.",
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author = "Ayaka Sakakura and Martin Pauze and Atsuhiro Namiki and Megumi Tago and Hiroomi Tamura and Kengo Hanaya and Shuhei Higashibayashi and Takeshi Sugai",
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T1 - Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides

AU - Sakakura, Ayaka

AU - Pauze, Martin

AU - Namiki, Atsuhiro

AU - Tago, Megumi

AU - Tamura, Hiroomi

AU - Hanaya, Kengo

AU - Higashibayashi, Shuhei

AU - Sugai, Takeshi

PY - 2019/1/1

Y1 - 2019/1/1

N2 - 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.

AB - 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.

KW - Anti-inflammatory effect

KW - Chemoselective acylation

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KW - Hydroxytyrosol

KW - Site-selective hydroxylation

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