Enzymatic Synthesis of 4-Hydroxyphenyl β-D-Oligoxylosides and Their Notable Tyrosinase Inhibitory Activity

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概要

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• 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 β-D-oligoxylosides, β-(Xyl)n-HQ (n=1–4), by one step reaction. The obtained β-(Xyl)n-HQ inhibited mushroom tyrosinase, which catalyzes the oxidation of L-DOPA to L-DOPA quinine, and the IC50 values of β-Xyl-HQ, β-(Xyl)2-HQ, β-(Xyl)3-HQ, and β-(Xyl)4-HQ were 3.0, 0.74, 0.48, and 0.18 mM respectively. β-(Xyl)4-HQ showed 35-fold more potent inhibitory activity than β-arbutin (4-hydroxyphenyl β-D-glucopyranoside), of which the IC50 value was measured to be 6.3 mM. Kinetic analysis revealed that β-(Xyl)2-HQ, β-(Xyl)3-HQ, and β-(Xyl)4-HQ competitively inhibited the enzyme, and the corresponding Ki values were calculated to be 0.20, 0.29, and 0.057 mM respectively.

• 2009-05-23

著者

• Nishida Yoshihiro

  Department Of Applied Biological Chemistry Faculty Of Agriculture Tohoku University

• Ando Akikazu

  Department Of Agricultural Chemistry Chiba University

• SHINOYAMA HIROFUMI

  School of Art and Design, Meisei University

• Dohi Hirofumi

  Department Of Bioorganic Chemistry Graduate School Of Horticulture

• Ando Akikazu

  Department Of Nanobiology Graduate School Of Advanced Integration Science

• Saito Akihiro

  Department Of Nanobiology Graduate School Of Advanced Integration Science

• Shinoyama Hirofumi

  School Of Art And Design Meisei University

• Chiku Kazuhiro

  Department Of Advanced Bioresource Science Graduate School Of Science And Technology

• Saito Akihiro

  Department Of Applied Biology And Chemistry Tokyo University Of Agriculture

• EBISE Hiroshi

  Department of Bioresource Chemistry, Faculty of Horticulture, Chiba University

• KOUZAI Yusuke

  Department of Nanobiology, Graduate School of Advanced Integration Science

• Kouzai Yusuke

  Department Of Nanobiology Graduate School Of Advanced Integration Science

• Ebise Hiroshi

  Department Of Bioresource Chemistry Faculty Of Horticulture Chiba University

• Nishida Yoshihiro

  Department Of Bioorganic Chemistry Graduate School Of Horticulture

• Saito Akihiro

  Department Of Applied Biology And Chemistry Faculty Of Applied Bio-science Tokyo University Of Agric

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