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• W1498682634 abstract "This chapter reviews our current knowledge of the chemistry and chemical ecology of ellagitannins (ETs), placing particular emphasis on the role these under-appreciated polyphenols play in plant–herbivore interactions. Instead of the traditional tannin-linked activity that comes from their complex formation with proteins, it discusses tannins' less well-known pro-oxidant activity. ETs are likely the most active tannin pro-oxidants. Plant cells synthesize ETs via the shikimate pathway, utilizing the enzymatic conversion of dehydroshikimic acid into gallic acid and further to galloyl glucoses. During the biosynthetic steps from monogalloyl glucose towards pentagalloyl glucose, the pro-oxidant activity of the polyphenols decreases, but it begins to increase again as soon as pentagalloyl glucose is transformed to glucopyranose-based ETs and further to very active C-glycosidic ETs. Thus, the tannin-based pro-oxidant capacity of a plant cell is highly dependent on the total and relative concentrations of different types of products or intermediates of the hydrolyzable tannin pathway. Within plant species that accumulate different types of galloyl glucoses and ETs differing in pro-oxidant activities, this balance typically varies significantly. The situation is further complicated by the variation in ETs observed seasonally and between individual plants. In addition, ETs may also derive their antiherbivore activities via their hydrolysis products, which is largely an unexplored area of research. Historically, ETs have not been taken specifically into account as plant-defense compounds, mainly due to difficulties in their compound-specific analysis from the plant cell. Recent developments in tannin chemistry have diminished these problems and the joint effort of ecologists and chemists can be used to verify the true ecological and evolutionary significance of ETs in plant–herbivore interactions." @default.
• W1498682634 created "2016-06-24" @default.
• W1498682634 creator A5090778651 @default.
• W1498682634 date "2014-08-11" @default.
• W1498682634 modified "2023-10-11" @default.
• W1498682634 title "The Chemistry and Chemical Ecology of Ellagitannins in Plant–Insect Interactions: From Underestimated Molecules to Bioactive Plant Constituents" @default.
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• W1498682634 doi "https://doi.org/10.1002/9781118329634.ch4" @default.
• W1498682634 hasPublicationYear "2014" @default.
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