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

• Published in: Bioscience, Biotechnology, and Biochemistry
• Main Authors: Sakakura, Ayaka, Pauze, Martin, Namiki, Atsuhiro, Funakoshi-Tago, Megumi, Tamura, Hiroomi, Hanaya, Kengo, Higashibayashi, Shuhei, Sugai, Takeshi
• Other Authors: JSPS KAKENHI, Amano Institute of Technology
• Format: Article in Journal/Newspaper
• Language: English
• Published: Oxford University Press (OUP) 2019
• Subjects: Organic Chemistry; Molecular Biology; Applied Microbiology and Biotechnology; General Medicine; Biochemistry; Analytical Chemistry; Biotechnology; Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1080/09168451.2018.1530970; http://academic.oup.com/bbb/article-pdf/83/2/185/36834427/bbb0185.pdf

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.