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Stereoselectivity of the Biosynthesis of Norlignans and Related Compounds

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The Biological Activity of Phytochemicals

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 41))

Abstract

Norlignans, lignans, and neolignans are biosynthesized by coupling two units of phenylpropanoid monomers including p-hydroxycinnamyl alcohols and allyl- and propenylphenols. Each molecule of the phenylpropanoid dimers is usually chiral, and naturally occurring norlignans, lignans, and neolignans are often optically active. The subunit compositions of norlignan synthase (hinokiresinol synthase) are known to control enantiomeric selectivity as well as cis/trans selectivity during norlignan formation. This contrasts sharply with the dirigent protein-mediated enantioselective control in lignan biosynthesis. Indeed, the dirigent protein is a unique asymmetric inducer that plays prominent roles in enantioselective lignan biosynthesis. Recently, however, enzymes that are involved in the subsequent metabolic steps, such as pinoresinol (/lariciresinol) reductase, were also found to play significant roles in the enantioselective formation of lignans. In this review, recent advances in the biosynthesis of norlignans, lignans, and neolignans are discussed in relation to enantioselective control mechanisms.

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Authors and Affiliations

  1. Research Institute for Sustainable Humanosphere, Kyoto University, Kyoto, 611-0011, Japan

    Toshiaki Umezawa, Masaomi Yamamura, Tomoyuki Nakatsubo, Shiro Suzuki & Takefumi Hattori

  2. Institute of Sustainability Science, Kyoto University, Kyoto, 611-0011, Japan

    Toshiaki Umezawa & Shiro Suzuki

  3. Central Laboratory, Rengo Co., Ltd., 4-1-186 Ohiraki Fukushima-ku, Osaka, 553-0007, Japan

    Tomoyuki Nakatsubo

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  1. Toshiaki Umezawa
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  2. Masaomi Yamamura
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  3. Tomoyuki Nakatsubo
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  4. Shiro Suzuki
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  5. Takefumi Hattori
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Correspondence to Toshiaki Umezawa .

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  1. , Institute of Biological Chemistry, Washington State University, P.O. Box 646340, Pullman, 99164-6340, USA

    David R. Gang

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Umezawa, T., Yamamura, M., Nakatsubo, T., Suzuki, S., Hattori, T. (2011). Stereoselectivity of the Biosynthesis of Norlignans and Related Compounds. In: Gang, D. (eds) The Biological Activity of Phytochemicals. Recent Advances in Phytochemistry, vol 41. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-7299-6_12

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