Inhibitory compound of tyrosinase activity from the sprout of Polygonum hydropiper L. (Benitade).
A tyrosinase inhibitor was isolated from the sprout of Polygonum hydropiper L. (Benitade) by activity-guided fractionation and identified as (2R,3R)-+-taxifolin (1) by spectroscopic means. Compound 1 inhibited 70% of tyrosinase activity at a concentration of 0.50 mM. ID50 (50% inhibition dose) value of compound 1 was 0.24 mM. As compared with tyrosinase inhibitor known cosmetic agent such as arbutin and kojic acid, compound 1 was more inhibited than the former and showed inhibitory effect equal to that of the latter. To study the inhibitory effect of (2R,3R)-+-taxifolin derivatives against tyrosinase activity, 3,7,3',4'-taxifolin tetraacetate (2) and 5,7,3',4'-taxifolin teramethyl ether (3) were also assayed together with compound 1.
Miyazawa
Mitsuo
M
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosaka, Osaka 577-8502, Japan. miyazawa@apch.kindai.ac.jp
Tamura
Naotaka
N
D001104:Arbutin / Q000737:chemistry / Q000494:pharmacology; D005591:Chemical Fractionation / Q000379:methods; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D044948:Flavonols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D018520:Plant Shoots / Q000737:chemistry*; D028502:Polygonum / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry / Q000494:pharmacology; D011794:Quercetin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods
C522106:3,7,3',4'-taxifolin tetraacetate; C522107:5,7,3',4'-taxifolin teramethyl ether; D004791:Enzyme Inhibitors; D044948:Flavonols; D011753:Pyrones; C011890:kojic acid; D011794:Quercetin; C003377:taxifolin; D001104:Arbutin; D014442:Monophenol Monooxygenase