TY - JOUR
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 - Funakoshi-Tago, Megumi
AU - Tamura, Hiroomi
AU - Hanaya, Kengo
AU - Higashibayashi, Shuhei
AU - Sugai, Takeshi
N1 - Funding Information:
M.P. thanks both of Graduate School of SIGMA Clermont and Graduate School of Pharmaceutical Sciences, Keio University, to participate in this study as a visiting research student under agreement from May to September in 2017. This work was supported by Japan society for the Promotion of Science KAKENHI (17K08286) for M.F.-T. and by a grant from a public interest incorporated foundation “Amano Institute of Technology” for T.S. and are gratefully acknowledged with thanks.
Publisher Copyright:
© 2018 Japan Society for Bioscience, Biotechnology, and Agrochemistry.
PY - 2019
Y1 - 2019
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 (IC 50 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 (IC 50 7.0 μM) among the tested compounds.
KW - Anti-inflammatory effect
KW - Chemoselective acylation
KW - Fatty acid monoesters
KW - Hydroxytyrosol
KW - Site-selective hydroxylation
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U2 - 10.1080/09168451.2018.1530970
DO - 10.1080/09168451.2018.1530970
M3 - Article
C2 - 30319060
AN - SCOPUS:85060392114
SN - 0916-8451
VL - 83
SP - 185
EP - 191
JO - Bioscience, Biotechnology and Biochemistry
JF - Bioscience, Biotechnology and Biochemistry
IS - 2
ER -