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Recent progress in ellagitannin chemistry.

Abstract
Continuing studies on the total synthesis of ellagitannin plant metabolites have led to the preparation of the dimeric antitumor compound, coriariin A, as well as designed structural analogues. In related investigations, the synthesis of a 2,4-hexahydroxydiphenoyl (HHDP)-bearing glucopyranose structure has been achieved. This species is related to the geraniin family of ellagitannins, and its subsequent chemistry is suggestive of a mechanistic rationale for the observation that the HHDP units within (3,6-bridged)2,4-HHDP-containing ellagitannins invariably are oxidized further in vivo. Companion studies designed to assay the immunomodulatory properties of coriariin A and analogues have led to the thesis that tumor necrosis factor alpha (TNFalpha) serves as a mediator of this ellagitannin's tumor remissive activity. Furthermore, certain tannins and tannin analogues appear to act in an immunosuppressive capacity with peripheral blood monocytes that were exposed to the bacterially derived septic shock inducing agent lipid A.
AuthorsKen S Feldman
JournalPhytochemistry (Phytochemistry) Vol. 66 Issue 17 Pg. 1984-2000 (Sep 2005) ISSN: 0031-9422 [Print] England
PMID16153404 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, U.S. Gov't, P.H.S., Review)
Chemical References
  • Hydrolyzable Tannins
  • Immunosuppressive Agents
  • ellagitannin
Topics
  • Hydrolyzable Tannins (chemistry, pharmacology)
  • Immunosuppressive Agents (chemistry, pharmacology)

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