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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2020-09-01
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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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