| RRC ID |
60115
|
| Author |
Sakakura A, Pauze M, Namiki A, Funakoshi-Tago M, Tamura H, Hanaya K, Higashibayashi S, Sugai T.
|
| Title |
Chemoenzymatic synthesis of hydroxytyrosol monoesters and their suppression effect on nitric oxide production stimulated by lipopolysaccharides.
|
| Journal |
Biosci Biotechnol Biochem
|
| 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.
|
| Volume |
83(2)
|
| Pages |
185-191
|
| Published |
2019-2-1
|
| DOI |
10.1080/09168451.2018.1530970
|
| PMID |
30319060
|
| MeSH |
Acylation
Animals
Carbon-13 Magnetic Resonance Spectroscopy
Esters / chemical synthesis*
Esters / chemistry
Esters / pharmacology
Fungal Proteins / metabolism*
Hydroxylation
Inhibitory Concentration 50
Lipase / metabolism*
Lipopolysaccharides / pharmacology*
Mice
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide / biosynthesis*
Phenylethyl Alcohol / analogs & derivatives*
Phenylethyl Alcohol / chemical synthesis
Phenylethyl Alcohol / chemistry
Phenylethyl Alcohol / pharmacology
Proton Magnetic Resonance Spectroscopy
RAW 264.7 Cells
Spectrometry, Mass, Electrospray Ionization
|
| IF |
1.297
|
| Times Cited |
2
|
| Resource |
| Human and Animal Cells |
RAW 264(RCB0535) |
