Mushroom tyrosinase inhibitory activity of esculetin isolated from seeds of Euphorbia lathyris L

A tyrosinase inhibitor was isolated from the seeds of Euphorbia lathyris L. by bioassay-guided fractionation and purification, using silica gel column chromatography. It was identified as esculetin by comparing its physical properties and spectral data with those of an authentic sample. The IC 50 va...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2003-03, Vol.67 (3), p.631-634
Main Authors: Masamoto, Y. (Okayama Univ. (Japan)), Ando, H, Murata, Y, Shimoishi, Y, Tada, M, Takahata, K
Format: Article
Language:English
Subjects:
Agaricales - enzymology
Binding, Competitive
Biological and medical sciences
coumarin
Coumarins - chemistry
EDIBLE FUNGI
ENZYME INHIBITORS
esculetin
EUPHORBIA LATHYRIS
Euphorbia lathyris L
Euphorbiaceae - chemistry
Fundamental and applied biological sciences. Psychology
Inhibitory Concentration 50
Kinetics
Levodopa - metabolism
mushroom tyrosinase inhibitory activity
OXIDOREDUCTASES
Peptides - chemistry
Peptides - isolation & purification
Peptides - pharmacology
Pyrones - pharmacology
SEEDS
Seeds - chemistry
Structure-Activity Relationship
TYROSINE
Umbelliferones - chemistry
Umbelliferones - isolation & purification
Umbelliferones - pharmacology
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Summary:A tyrosinase inhibitor was isolated from the seeds of Euphorbia lathyris L. by bioassay-guided fractionation and purification, using silica gel column chromatography. It was identified as esculetin by comparing its physical properties and spectral data with those of an authentic sample. The IC 50 value of esculetin in the mushroom tyrosinase activity test was 43 μM. The kinetic study indicates that esculetin exhibited competitive inhibition against the oxidation of 3-(3,4-dihydroxyphenyl)-alanine by mushroom tyrosinase. The structure-activity relationships among five esculetin analogs suggest that hydroxyl groups at the C6 and C7 positions of the coumarin skeleton played an important role in the expression of tyrosinase inhibitory activity.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.67.631