Enzymatic synthesis of 4-hydroxyphenyl beta-D-oligoxylosides and their notable tyrosinase inhibitory activity.
We have purified and characterized an oligoxylosyl transfer enzyme (OxtA) from Bacillus sp. strain KT12. In the present study, a N-terminally His-tagged recombinant form of the enzyme, OxtA(H)(E), was overproduced in Escherichia coli and applied to the reaction with xylan and hydroquinone to produce 4-hydroxyphenyl beta-D-oligoxylosides, beta-(Xyl)(n)-HQ (n=1-4), by one step reaction. The obtained beta-(Xyl)(n)-HQ inhibited mushroom tyrosinase, which catalyzes the oxidation of L-DOPA to L-DOPA quinine, and the IC(50) values of beta-Xyl-HQ, beta-(Xyl)(2)-HQ, beta-(Xyl)(3)-HQ, and beta-(Xyl)(4)-HQ were 3.0, 0.74, 0.48, and 0.18 mM respectively. beta-(Xyl)(4)-HQ showed 35-fold more potent inhibitory activity than beta-arbutin (4-hydroxyphenyl beta-D-glucopyranoside), of which the IC(50) value was measured to be 6.3 mM. Kinetic analysis revealed that beta-(Xyl)(2)-HQ, beta-(Xyl)(3)-HQ, and beta-(Xyl)(4)-HQ competitively inhibited the enzyme, and the corresponding K(i) values were calculated to be 0.20, 0.29, and 0.057 mM respectively.
Chiku
Kazuhiro
K
Department of Advanced Bioresource Science, Graduate School of Science and Technology, Matsudo, Chiba, Japan. chiku06UD7204@graduate.chiba-u.jp
Dohi
Hirofumi
H
Saito
Akihiro
A
Ebise
Hiroki
H
Kouzai
Yusuke
Y
Shinoyama
Hirofumi
H
Nishida
Yoshihiro
Y
Ando
Akikazu
A
D000363:Agaricales / Q000201:enzymology; D001407:Bacillus / Q000201:enzymology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004926:Escherichia coli / Q000235:genetics; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016695:Glycosyltransferases / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D006873:Hydroquinones / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D014994:Xylose / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D004791:Enzyme Inhibitors; D006027:Glycosides; D006873:Hydroquinones; C089329:hydroquinone (1-4)-xyloside; C077140:4-hydroxyphenyl-O-xyloside; D014994:Xylose; D014442:Monophenol Monooxygenase; D016695:Glycosyltransferases