Diversification of Chemical Structures of Methoxylated Flavonoids and Genes Encoding Flavonoid--Methyltransferases

Overview

Journal Plants (Basel)

Date 2022 Feb 26

PMID 35214897

Authors

Yuting Liu

Alisdair R Fernie

Takayuki Tohge

Affiliations

Soon will be listed here.

Abstract

The -methylation of specialized metabolites in plants is a unique decoration that provides structural and functional diversity of the metabolites with changes in chemical properties and intracellular localizations. The -methylation of flavonoids, which is a class of plant specialized metabolites, promotes their antimicrobial activities and liposolubility. Flavonoid -methyltransferases (FOMTs), which are responsible for the -methylation process of the flavonoid aglycone, generally accept a broad range of substrates across flavones, flavonols and lignin precursors, with different substrate preferences. Therefore, the characterization of FOMTs with the physiology roles of methoxylated flavonoids is useful for crop improvement and metabolic engineering. In this review, we summarized the chemodiversity and physiology roles of methoxylated flavonoids, which were already reported, and we performed a cross-species comparison to illustrate an overview of diversification and conserved catalytic sites of the flavonoid -methyltransferases.

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References

Salim V, Jones A, DellaPenna D . Camptotheca acuminata 10-hydroxycamptothecin O-methyltransferase: an alkaloid biosynthetic enzyme co-opted from flavonoid metabolism. Plant J. 2018; 95(1):112-125. DOI: 10.1111/tpj.13936. View

Han J, Wan H, Ge L, Zhu Z, Guo Y, Zhang Y . [Protective effect of 3'-methoxy puerarin on cerebral ischemic injury/ reperfusion in rats]. Zhongguo Zhong Yao Za Zhi. 2009; 34(11):1422-5. View

Uchida K, Sawada Y, Ochiai K, Sato M, Inaba J, Hirai M . Identification of a Unique Type of Isoflavone O-Methyltransferase, GmIOMT1, Based on Multi-Omics Analysis of Soybean under Biotic Stress. Plant Cell Physiol. 2020; 61(11):1974-1985. PMC: 7758036. DOI: 10.1093/pcp/pcaa112. View

Gauthier A, Gulick P, Ibrahim R . cDNA cloning and characterization of a 3'/5'-O-methyltransferase for partially methylated flavonols from Chrysosplenium americanum. Plant Mol Biol. 1996; 32(6):1163-9. DOI: 10.1007/BF00041401. View

Breakspear A, Liu C, Roy S, Stacey N, Rogers C, Trick M . The root hair "infectome" of Medicago truncatula uncovers changes in cell cycle genes and reveals a requirement for Auxin signaling in rhizobial infection. Plant Cell. 2014; 26(12):4680-701. PMC: 4311213. DOI: 10.1105/tpc.114.133496. View

Ferrer J, Zubieta C, Dixon R, Noel J . Crystal structures of alfalfa caffeoyl coenzyme A 3-O-methyltransferase. Plant Physiol. 2005; 137(3):1009-17. PMC: 1065401. DOI: 10.1104/pp.104.048751. View

Kim D, Kim B, Lee Y, Ryu J, Lim Y, Hur H . Regiospecific methylation of naringenin to ponciretin by soybean O-methyltransferase expressed in Escherichia coli. J Biotechnol. 2005; 119(2):155-62. DOI: 10.1016/j.jbiotec.2005.04.004. View

Schroder G, Wehinger E, Lukacin R, Wellmann F, Seefelder W, Schwab W . Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Phytochemistry. 2004; 65(8):1085-94. DOI: 10.1016/j.phytochem.2004.02.010. View

Tohge T, Wendenburg R, Ishihara H, Nakabayashi R, Watanabe M, Sulpice R . Characterization of a recently evolved flavonol-phenylacyltransferase gene provides signatures of natural light selection in Brassicaceae. Nat Commun. 2016; 7:12399. PMC: 4996938. DOI: 10.1038/ncomms12399. View

10.

Wils C, Brandt W, Manke K, Vogt T . A single amino acid determines position specificity of an Arabidopsis thaliana CCoAOMT-like O-methyltransferase. FEBS Lett. 2013; 587(6):683-9. DOI: 10.1016/j.febslet.2013.01.040. View

11.

Kumar S, Stecher G, Li M, Knyaz C, Tamura K . MEGA X: Molecular Evolutionary Genetics Analysis across Computing Platforms. Mol Biol Evol. 2018; 35(6):1547-1549. PMC: 5967553. DOI: 10.1093/molbev/msy096. View

12.

Kim B, Kim H, Hur H, Lim Y, Ahn J . Regioselectivity of 7-O-methyltransferase of poplar to flavones. J Biotechnol. 2006; 126(2):241-7. DOI: 10.1016/j.jbiotec.2006.04.019. View

13.

Liu C, Murray J . The Role of Flavonoids in Nodulation Host-Range Specificity: An Update. Plants (Basel). 2016; 5(3). PMC: 5039741. DOI: 10.3390/plants5030033. View

14.

Kovinich N, Saleem A, Arnason J, Miki B . Combined analysis of transcriptome and metabolite data reveals extensive differences between black and brown nearly-isogenic soybean (Glycine max) seed coats enabling the identification of pigment isogenes. BMC Genomics. 2011; 12:381. PMC: 3163566. DOI: 10.1186/1471-2164-12-381. View

15.

Koirala N, Thuan N, Ghimire G, Van Thang D, Sohng J . Methylation of flavonoids: Chemical structures, bioactivities, progress and perspectives for biotechnological production. Enzyme Microb Technol. 2016; 86:103-16. DOI: 10.1016/j.enzmictec.2016.02.003. View

16.

Barakat A, Choi A, Yassin N, Park J, Sun Z, Carlson J . Comparative genomics and evolutionary analyses of the O-methyltransferase gene family in Populus. Gene. 2011; 479(1-2):37-46. DOI: 10.1016/j.gene.2011.02.008. View

17.

Zhang Y, Xu R, Gao S, Cheng A . Enzymatic production of oroxylin A and hispidulin using a liverwort flavone 6-O-methyltransferase. FEBS Lett. 2016; 590(16):2619-28. DOI: 10.1002/1873-3468.12312. View

18.

Kornblatt J, Zhou J, Ibrahim R . Structure-activity relationships of wheat flavone O-methyltransferase: a homodimer of convenience. FEBS J. 2008; 275(9):2255-66. DOI: 10.1111/j.1742-4658.2008.06377.x. View

19.

Hugueney P, Provenzano S, Verries C, Ferrandino A, Meudec E, Batelli G . A novel cation-dependent O-methyltransferase involved in anthocyanin methylation in grapevine. Plant Physiol. 2009; 150(4):2057-70. PMC: 2719152. DOI: 10.1104/pp.109.140376. View

20.

Khouri H, Tahara S, Ibrahim R . Partial purification, characterization, and kinetic analysis of isoflavone 5-O-methyltransferase from yellow lupin roots. Arch Biochem Biophys. 1988; 262(2):592-8. DOI: 10.1016/0003-9861(88)90410-9. View