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.
Department of Advanced Bioresource Science, Graduate School of Science and Technology, Matsudo, Chiba, Japan. chiku06UD7204@graduate.chiba-u.jp
Kazuhiro
K
Chiku
Hirofumi
H
Dohi
Akihiro
A
Saito
Hiroki
H
Ebise
Yusuke
Y
Kouzai
Hirofumi
H
Shinoyama
Yoshihiro
Y
Nishida
Akikazu
A
Ando
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