Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production

Methylation is a common structural modification that can alter and improve the biological activities of natural compounds. <i>O</i>-Methyltransferases (OMTs) catalyze the methylation of a wide array of secondary metabolites, including flavonoids, and are potentially useful tools for the...

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Main Authors: Hye Lin Park, Jae Chul Lee, Kyungha Lee, Jeong Min Lee, Hyo Jeong Nam, Seong Hee Bhoo, Tae Hoon Lee, Sang-Won Lee, Man-Ho Cho
Format: Article
Language:English
Published: MDPI AG 2020-09-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/19/4455
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author Hye Lin Park
Jae Chul Lee
Kyungha Lee
Jeong Min Lee
Hyo Jeong Nam
Seong Hee Bhoo
Tae Hoon Lee
Sang-Won Lee
Man-Ho Cho
author_facet Hye Lin Park
Jae Chul Lee
Kyungha Lee
Jeong Min Lee
Hyo Jeong Nam
Seong Hee Bhoo
Tae Hoon Lee
Sang-Won Lee
Man-Ho Cho
author_sort Hye Lin Park
collection DOAJ
description Methylation is a common structural modification that can alter and improve the biological activities of natural compounds. <i>O</i>-Methyltransferases (OMTs) catalyze the methylation of a wide array of secondary metabolites, including flavonoids, and are potentially useful tools for the biotechnological production of valuable natural products. An <i>OMT</i> gene (<i>PfOMT3</i>) was isolated from perilla leaves as a putative flavonoid OMT (FOMT). Phylogenetic analysis and sequence comparisons showed that PfOMT3 is a class II OMT. Recombinant PfOMT3 catalyzed the methylation of flavonoid substrates, whereas no methylated product was detected in PfOMT3 reactions with phenylpropanoid substrates. Structural analyses of the methylation products revealed that PfOMT3 regiospecifically transfers a methyl group to the 7-OH of flavonoids. These results indicate that PfOMT3 is an FOMT that catalyzes the 7-<i>O</i>-methylation of flavonoids. PfOMT3 methylated diverse flavonoids regardless of their backbone structure. Chrysin, naringenin and apigenin were found to be the preferred substrates of PfOMT3. Recombinant PfOMT3 showed moderate OMT activity toward eriodictyol, luteolin and kaempferol. To assess the biotechnological potential of PfOMT3, the biotransformation of flavonoids was performed using <i>PfOMT3</i>-transformed <i>Escherichia coli</i>. Naringenin and kaempferol were successfully bioconverted to the 7-methylated products sakuranetin and rhamnocitrin, respectively, by <i>E. coli</i> harboring <i>PfOMT3</i>.
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spelling doaj.art-1aebba98d49b478da207c22bfb97d3d62023-11-20T15:24:40ZengMDPI AGMolecules1420-30492020-09-012519445510.3390/molecules25194455Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid ProductionHye Lin Park0Jae Chul Lee1Kyungha Lee2Jeong Min Lee3Hyo Jeong Nam4Seong Hee Bhoo5Tae Hoon Lee6Sang-Won Lee7Man-Ho Cho8Department of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaDepartment of Applied Chemistry, Kyung Hee University, Yongin 17104, KoreaDepartment of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaDepartment of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaDepartment of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaDepartment of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaDepartment of Applied Chemistry, Kyung Hee University, Yongin 17104, KoreaDepartment of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaDepartment of Genetic Engineering, Kyung Hee University, Yongin 17104, KoreaMethylation is a common structural modification that can alter and improve the biological activities of natural compounds. <i>O</i>-Methyltransferases (OMTs) catalyze the methylation of a wide array of secondary metabolites, including flavonoids, and are potentially useful tools for the biotechnological production of valuable natural products. An <i>OMT</i> gene (<i>PfOMT3</i>) was isolated from perilla leaves as a putative flavonoid OMT (FOMT). Phylogenetic analysis and sequence comparisons showed that PfOMT3 is a class II OMT. Recombinant PfOMT3 catalyzed the methylation of flavonoid substrates, whereas no methylated product was detected in PfOMT3 reactions with phenylpropanoid substrates. Structural analyses of the methylation products revealed that PfOMT3 regiospecifically transfers a methyl group to the 7-OH of flavonoids. These results indicate that PfOMT3 is an FOMT that catalyzes the 7-<i>O</i>-methylation of flavonoids. PfOMT3 methylated diverse flavonoids regardless of their backbone structure. Chrysin, naringenin and apigenin were found to be the preferred substrates of PfOMT3. Recombinant PfOMT3 showed moderate OMT activity toward eriodictyol, luteolin and kaempferol. To assess the biotechnological potential of PfOMT3, the biotransformation of flavonoids was performed using <i>PfOMT3</i>-transformed <i>Escherichia coli</i>. Naringenin and kaempferol were successfully bioconverted to the 7-methylated products sakuranetin and rhamnocitrin, respectively, by <i>E. coli</i> harboring <i>PfOMT3</i>.https://www.mdpi.com/1420-3049/25/19/4455PfOMT3flavonoid 7-<i>O</i>-methyltransferaseperilla7-methoxyflavonoidbiotransformation
spellingShingle Hye Lin Park
Jae Chul Lee
Kyungha Lee
Jeong Min Lee
Hyo Jeong Nam
Seong Hee Bhoo
Tae Hoon Lee
Sang-Won Lee
Man-Ho Cho
Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
Molecules
PfOMT3
flavonoid 7-<i>O</i>-methyltransferase
perilla
7-methoxyflavonoid
biotransformation
title Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
title_full Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
title_fullStr Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
title_full_unstemmed Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
title_short Biochemical Characterization of a Flavonoid <i>O</i>-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
title_sort biochemical characterization of a flavonoid i o i methyltransferase from perilla leaves and its application in 7 methoxyflavonoid production
topic PfOMT3
flavonoid 7-<i>O</i>-methyltransferase
perilla
7-methoxyflavonoid
biotransformation
url https://www.mdpi.com/1420-3049/25/19/4455
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