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Article

Optimization of the Biosynthesis of B-Ring Ortho-Hydroxy Lated Flavonoids Using the 4-Hydroxyphenylacetate 3-Hydroxylase Complex (HpaBC) of Escherichia coli

by
Longji Wang
1,2,†,
Xiubing Ma
1,2,†,
Haixiang Ruan
1,2,
Yang Chen
1,
Liping Gao
1,
Ting Lei
1,
Yan Li
1,
Lin Gui
1,
Lina Guo
1,
Tao Xia
2 and
Yunsheng Wang
1,2,*
1
School of Life Science, Anhui Agricultural University, Hefei 230036, China
2
State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China
*
Author to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Molecules 2021, 26(10), 2919; https://doi.org/10.3390/molecules26102919
Submission received: 29 March 2021 / Revised: 27 April 2021 / Accepted: 8 May 2021 / Published: 14 May 2021
(This article belongs to the Section Applied Chemistry)
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Abstract

Flavonoids are important plant metabolites that exhibit a wide range of physiological and pharmaceutical functions. Because of their wide biological activities, such as anti-inflammatory, antioxidant, antiaging and anticancer, they have been widely used in foods, nutraceutical and pharmaceuticals industries. Here, the hydroxylase complex HpaBC was selected for the efficient in vivo production of ortho-hydroxylated flavonoids. Several HpaBC expression vectors were constructed, and the corresponding products were successfully detected by feeding naringenin to vector-carrying strains. However, when HpaC was linked with an S-Tag on the C terminus, the enzyme activity was significantly affected. The optimal culture conditions were determined, including a substrate concentration of 80 mg·L−1, an induction temperature of 28 °C, an M9 medium, and a substrate delay time of 6 h after IPTG induction. Finally, the efficiency of eriodictyol conversion from P2&3-carrying strains fed naringin was up to 57.67 ± 3.36%. The same strategy was used to produce catechin and caffeic acid, and the highest conversion efficiencies were 35.2 ± 3.14 and 32.93 ± 2.01%, respectively. In this paper, the catalytic activity of HpaBC on dihydrokaempferol and kaempferol was demonstrated for the first time. This study demonstrates a feasible method for efficiently synthesizing in vivo B-ring dihydroxylated flavonoids, such as catechins, flavanols, dihydroflavonols and flavonols, in a bacterial expression system.
Keywords: B-ring ortho-hydroxylation; Escherichia coli; flavonoids; 4-hydroxyphenylacetate 3-hydroxylase; biosynthesis B-ring ortho-hydroxylation; Escherichia coli; flavonoids; 4-hydroxyphenylacetate 3-hydroxylase; biosynthesis

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MDPI and ACS Style

Wang, L.; Ma, X.; Ruan, H.; Chen, Y.; Gao, L.; Lei, T.; Li, Y.; Gui, L.; Guo, L.; Xia, T.; et al. Optimization of the Biosynthesis of B-Ring Ortho-Hydroxy Lated Flavonoids Using the 4-Hydroxyphenylacetate 3-Hydroxylase Complex (HpaBC) of Escherichia coli. Molecules 2021, 26, 2919. https://doi.org/10.3390/molecules26102919

AMA Style

Wang L, Ma X, Ruan H, Chen Y, Gao L, Lei T, Li Y, Gui L, Guo L, Xia T, et al. Optimization of the Biosynthesis of B-Ring Ortho-Hydroxy Lated Flavonoids Using the 4-Hydroxyphenylacetate 3-Hydroxylase Complex (HpaBC) of Escherichia coli. Molecules. 2021; 26(10):2919. https://doi.org/10.3390/molecules26102919

Chicago/Turabian Style

Wang, Longji, Xiubing Ma, Haixiang Ruan, Yang Chen, Liping Gao, Ting Lei, Yan Li, Lin Gui, Lina Guo, Tao Xia, and et al. 2021. "Optimization of the Biosynthesis of B-Ring Ortho-Hydroxy Lated Flavonoids Using the 4-Hydroxyphenylacetate 3-Hydroxylase Complex (HpaBC) of Escherichia coli" Molecules 26, no. 10: 2919. https://doi.org/10.3390/molecules26102919

APA Style

Wang, L., Ma, X., Ruan, H., Chen, Y., Gao, L., Lei, T., Li, Y., Gui, L., Guo, L., Xia, T., & Wang, Y. (2021). Optimization of the Biosynthesis of B-Ring Ortho-Hydroxy Lated Flavonoids Using the 4-Hydroxyphenylacetate 3-Hydroxylase Complex (HpaBC) of Escherichia coli. Molecules, 26(10), 2919. https://doi.org/10.3390/molecules26102919

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