Recent Advances in Lignan OMT Studies

  • Umezawa Toshiaki
    Research Institute for Sustainable Humanosphere, Kyoto University Research Unit for Development of Global Sustainability, Kyoto University
  • Yamamura Masaomi
    Research Institute for Sustainable Humanosphere, Kyoto University
  • Ono Eiichiro
    Suntory Global Innovation Center
  • Shiraishi Akira
    Suntory Foundation for Life Sciences, Bioorganic Research Institute
  • Ragamustari Safendrri Komara
    Research Institute for Sustainable Humanosphere, Kyoto University Research Unit for Development of Global Sustainability, Kyoto University

Bibliographic Information

Other Title
  • リグナンOMTに関する最新研究動向
  • リグナン OMT ニ カンスル サイシン ケンキュウ ドウコウ

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Description

<p>Lignans are phenylpropanoid dimers, where the phenylpropane units are linked by the central carbon (C8) of their propyl side chains. Lignans vary substantially in the chemical structure of their basic carbon frameworks, oxidation levels, and aromatic substitution patterns. O-Methylation on the aromatic rings is often crucial in determining the final product distribution. In the secondary or specialized metabolic processes of plants, O-methylation is usually catalyzed by S-adenosyl-L- methionine-dependent O-methyltransferases (OMTs). We have so far isolated six cDNAs encoding lignan OMTs: Carthamus tinctorius matairesinol OMT (CtMROMT), Sesamum indicum OMT1 (SiOMT1), Sesamum radiatum OMT1 (SrOMT1), Anthriscus sylvestris matairesinol OMT (AsMROMT), A. sylvestris thujaplicatin OMT (AsTJOMT), and Forsythia koreana matairesinol OMT (FkMROMT). Phylogenetic tree analysis indicated that CtMROMT and AsMROMT formed a small clade with plant OMTs including caffeic acid O-methyltransferase from Rosa chinensis var. spontanea (RcOMT3) and reticuline 7-O-methyltransferase from Papaver somniferum (PsOMT1). By contrast, in the phylogenetic tree SiOMT1 and SrOMT1 were located closely to the clade containing 5-hydroxyconiferaldehyde OMTs [CAldOMTs, caffeic acid OMTs (CAOMTs)]. AsTJOMT and FkMROMT were located in a small clade which is somewhat close to the clade of SiOMT1, SrOMT1, and CAldOMTs. In addition, two lignan OMT genes, PhOMT1 and PhOMT3, were detected in Podophyllum hexandrum that is known to produce an antitumor lignan, podophyllotoxin. PhOMT1 showed slight sequence similarity to AsTJOMT and FkMROMT, while PhOMT3 shared low sequence similarity with the other 7 lignan OMTs. These lignan OMTs show diverse substrate specificities and different meta/para selectivity in phenolic O-methylation. Taken together, the lignin OMTs may have arisen independently in various lignan-producing plants via acquisition of substrate specificity for lineage-specific lignan structures. These findings on lignan OMTs provide useful information for further identification of cDNAs encoding other lignan OMTs, as well as clues to understand diversity and plasticity of plant secondary metabolism beyond lignan biosynthesis.</p>

Journal

  • Mokuzai Gakkaishi

    Mokuzai Gakkaishi 65 (1), 1-12, 2019-01-25

    The Japan Wood Research Society

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