Regiospecific synthesis of prenylated flavonoids by a prenyltransferase cloned from Fusarium oxysporum

分类： 生物学 >> 植物学 提交时间： 2017-07-10

Yang, Xiaoman Yang, Jiali Jiang, Yueming Yang, Hongshun Yun, Ze Rong, Weiliang Yang, Bao

摘要： Due to their impressive pharmaceutical activities and safety, prenylated flavonoids have a high potent to be applied as medicines and nutraceuticals. Biocatalysis is an effective technique to synthesize prenylated flavonoids. The major concern of this technique is that the microbe-derived prenyltransferases usually have poor regiospecificity and generate multiple prenylated products. In this work, a highly regiospecific prenyltransferase (FoPT1) was found from Fusarium oxysporum. It could recognize apigenin, naringenin, genistein, dihydrogenistein, kampferol, luteolin and hesperetin as substrates, and only 6-C-prenylated flavonoids were detected as the products. The catalytic effeciency of FoPT1 on flavonoids was in a decreasing order with hesperetin > naringenin > apigenin > genistein > luteolin > dihydrogenistein > kaempferol. Chalcones, flavanols and stilbenes were not active when acting as the substrates. 5,7-Dihydroxy and 4-carbonyl in flavonoid skeleton were required for the catalysis. 2,3-alkenyl was beneficial to the catalysis whereas 3-hydroxy impaired the prenylation reaction. Docking studies simulated the prenyl transfer reaction of FoPT1. E186 was involved in the formation of prenyl carbonium ion. E98, F89, F182, Y197 and E246 positioned apigenin for catalysis.

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