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Evolution of Novel O-methyltransferases from the Vanilla planifolia Caffeic Acid O-methyltransferase

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Abstract

The biosynthesis of many plant secondary compounds involves the methylation of one or more hydroxyl groups, catalyzed by O-methyltransferases (OMTs). Here, we report the characterization of two OMTs, Van OMT-2 and Van OMT-3, from the orchid Vanilla planifolia Andrews. These enzymes catalyze the methylation of a single outer hydroxyl group in substrates possessing a 1,2,3-trihydroxybenzene moiety, such as methyl gallate and myricetin. This is a substrate requirement not previously reported for any OMTs. Based on sequence analysis these enzymes are most similar to caffeic acid O-methyltransferases (COMTs), but they have negligible activity with typical COMT substrates. Seven of 12 conserved substrate-binding residues in COMTs are altered in Van OMT-2 and Van OMT-3. Phylogenetic analysis of the sequences suggests that Van OMT-2 and Van OMT-3 evolved from the V. planifolia COMT. These V. planifolia OMTs are new instances of COMT-like enzymes with novel substrate preferences.

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Abbreviations

COMT:

Caffeic acid O-methyltransferase

FOMT:

flavonoid O-methyltransferase

IEMT:

(iso)eugenol O-methyltransferase

IPTG:

isopropyl-β-d-thiogalactopyranoside

OMT:

O-methyltransferase

PCR:

polymerase chain reaction

SAM:

S-adenosyl-l-methionine

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Authors and Affiliations

  1. Department of Plant Biology and Pathology and The Biotechnology Center for Agriculture & the Environment, Cook College, Rutgers University, 59 Dudley Road, New Brunswick, NJ, 08901, USA

    Huaijun Michael Li, David Rotter, Fulya E. Pak, Daphna Havkin-Frenkel & Faith C. Belanger

  2. Center for Advanced Food Technology, Cook College, Rutgers University, New Brunswick, NJ, 08901, USA

    Thomas G. Hartman

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  1. Huaijun Michael Li
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  2. David Rotter
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  3. Thomas G. Hartman
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  4. Fulya E. Pak
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  5. Daphna Havkin-Frenkel
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  6. Faith C. Belanger
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Correspondence to Faith C. Belanger.

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Li, H.M., Rotter, D., Hartman, T.G. et al. Evolution of Novel O-methyltransferases from the Vanilla planifolia Caffeic Acid O-methyltransferase. Plant Mol Biol 61, 537–552 (2006). https://doi.org/10.1007/s11103-006-0029-4

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  • DOI: https://doi.org/10.1007/s11103-006-0029-4

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