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Biosynthesis and Biodegradation of Complex Gallotannins

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Plant Polyphenols 2

Part of the book series: Basic Life Sciences ((BLSC,volume 66))

Abstract

According to an already classical definition formulated by Freudenberg in 1920,1 plant tannins are divided into condensed tannins (nowadays often referred to as proanthocyanidins), which are derived from C-C linked flavan-3-ol units, and into hydrolyzahle tannins. The latter are characterized by a central polyol moiety (β-D-glucose in most cases) whose hydroxy functions are partially or completely esterified with gallic acid (3,4,5-trihydroxybenzoic acid, 1) (fig. 1) or also with more complex derivatives of this phenol. Stepwise substitution of glucose begins with the 1-O-galloyl derivative, β-glucogallin (2), and finally ends with 1,2,3,4,6-penta-O-galloyl-β-D-glucose (3), which is regarded as the immediate precursor of the two subclasses of hydrolyzable tannins, i.e., gallotannins and ellagitannins. Ellagitannins are thought to result from oxidative processes that form C-C linkages between adjacent galloyl residues of pentagalloylglucose to yield (R) or (S)-3,4,5,3′,4′,5′-hexahydroxydiphenoyl residues and that also lead to the subsequent formation of dimeric and oligomeric derivatives. Unfortunately, no experimental evidence is available to date for the biochemistry of these conversions.

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Authors and Affiliations

  1. Department of General Botany, University of Ulm, D-89069, Ulm, Germany

    Ruth Niemetz, Joerg U. Niehaus & Georg G. Gross

Authors
  1. Ruth Niemetz
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  2. Joerg U. Niehaus
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  3. Georg G. Gross
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Editor information

Editors and Affiliations

  1. University of Ulm, Ulm, Germany

    Georg G. Gross

  2. United States Department of Agriculture, Forest Service, Pineville, Louisiana, USA

    Richard W. Hemingway

  3. University of Okayama, Okayama, Japan

    Takashi Yoshida

  4. Kenner, Louisiana, USA

    Susan J. Branham

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© 1999 Kluwer Academic / Plenum Publishers, New York

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Niemetz, R., Niehaus, J.U., Gross, G.G. (1999). Biosynthesis and Biodegradation of Complex Gallotannins. In: Gross, G.G., Hemingway, R.W., Yoshida, T., Branham, S.J. (eds) Plant Polyphenols 2. Basic Life Sciences, vol 66. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4139-4_4

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  • DOI: https://doi.org/10.1007/978-1-4615-4139-4_4

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-46218-4

  • Online ISBN: 978-1-4615-4139-4

  • eBook Packages: Springer Book Archive

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