Title

Production of novel antioxidative prenyl naphthalen-ols by combinational bioconversion with dioxygenase PhnA1A2A3A4 and prenyltransferase NphB or SCO7190

Abstract

We performed combinational bioconversion of substituted naphthalenes with PhnA1A2A3A4 (an aromatic dihydroxylating dioxygenase from marine bacterium Cycloclasticus sp. strain A5) and prenyltransferase NphB (geranyltransferase from Streptomyces sp. strain CL190) or SCO7190 (dimethylallyltransferase from Streptomyces coelicolor A3(2)) to produce prenyl naphthalen-ols. Using 2-methylnaphthalene, 1-methoxynaphthalene, and 1-ethoxynaphthalene as the starting substrates, 10 novel prenyl naphthalen-ols were produced by combinational bioconversion. These novel prenyl naphthalen-ols each showed potent antioxidative activity against a rat brain homogenate model. 2-(2,3-Dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one (2',3'-dihydroxychrysin) generated with another aromatic dihydroxylating dioxygenase and subsequent dehydrogenase was also geranylated at the C-5'-carbon by the action of NphB.

Authors

Kazutoshi SHINDO, Ayako TACHIBANA, Ayumi TANAKA, Shizuka TOBA, Emi YUKI, Taro OZAKI, Takuto KUMANO, Makoto NISHIYAMA, Norihiko MISAWA, Tomohisa KUZUYAMA

Journal

Bioscience, Biotechnology and Biochemistry

Year, Volume, Page

2011, 75, 505

Reactions

3



Tag Element Regiochemistry Product Substrate Cofactor Enzyme
PTDBREC00301 C Regular SCO7190
PTDBREC00302 C Regular SCO7190
PTDBREC00303 C Regular SCO7190