Biology Reference
In-Depth Information
Chapter 4
Physicochemical Properties and Biomimetic
Reactions of Ellagitannins
Takashi Tanaka
Graduate School of Biomedical Sciences, College of Pharmaceutical
Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521,
Japan; t-tanaka@nagasaki-u.ac.jp
This chapter approaches ellagitannins from two different perspectives.
The first one has to do with the intriguing relationship between their
chemical structures and their water solubility. The oxidative metabolism
of hydrophobic gallotannins produces various ellagitannins of increasing
hydrophilicity. The hydrophobicity of ellagitannin monomers is
particularly relevant to their interaction with co-existing molecules and
to the biogenesis of their dimeric congeners. The second perspective
concerns the reactivity of a group of ellagitannins bearing highly
oxidized galloyl-derived units. Of particular interest is the special
chemical reactivity expressed by dehydrogenated hexahydroxydiphenoyl
ester units, which has been exploited in biomimetic synthesis, structural
determination and chromatographic analysis of some of the most
complex members of this fascinating family of natural products.
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