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Isolation of 6-hydroxy-L-tryptophan from the fruiting body of Lyophyllum decastes for use as a tyrosinase inhibitor.

Isolation of 6-hydroxy-L-tryptophan from the fruiting body of Lyophyllum decastes for use as a tyrosinase inhibitor.

Authors :
Ishihara A
Sugai N
Bito T
Ube N
Ueno K
Okuda Y
Fukushima-Sakuno E
Source :
Bioscience, biotechnology, and biochemistry [Biosci Biotechnol Biochem] 2019 Oct; Vol. 83 (10), pp. 1800-1806. Date of Electronic Publication: 2019 May 26.
Publication Year :
2019

Abstract

Tyrosinase is the key enzyme that controls melanin formation. We found that a hot water extract of the lyophilized fruiting body of the fungus Lyophyllum decastes inhibited tyrosinase from Agaricus bisporus . The extract was fractionated by ODS column chromatography, and an active compound was obtained by purification through successive preparative HPLC using an ODS and a HILIC column. Using spectroscopic data, the compound was identified to be an uncommon amino acid, 6-hydroxytryptophan. 6-Hydroxy-L-tryptophan and 6-hydroxy-D-tryptophan were prepared through a Fenton reaction from L-tryptophan and D-tryptophan, respectively. The active compound was determined to be 6-hydroxy-L-tryptophan by comparison of their circular dichroism spectra and retention time on HPLC analysis of the N <superscript>α</superscript> -(5-fluoro-2,4-dinitrophenyl)-L-leuciamide derivative with those of 6-hydroxy-L-tryptophan and 6-hydroxy-D-tryptophan. A Lineweaver-Burk plot of the enzyme reaction in the presence of 6-hydroxy-L-tryptophan indicated that this compound was a competitive inhibitor. The IC <subscript>50</subscript> values of 6-hydroxy-L-tryptophan was 0.23 mM.

Details

Language :
English
ISSN :
1347-6947
Volume :
83
Issue :
10
Database :
MEDLINE
Journal :
Bioscience, biotechnology, and biochemistry
Publication Type :
Academic Journal
Accession number :
31131717
Full Text :
https://doi.org/10.1080/09168451.2019.1621157