Chemistry and Biology of Rocaglamides (= Flavaglines) and Related Derivatives from Aglaia Species (Meliaceae)

  • Sherif S. Ebada
  • Neil Lajkiewicz
  • John A. PorcoJr.
  • Min Li-Weber
  • Peter Proksch
Chapter
First Online:
Part of the Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products book series (POGRCHEM, volume 94)

Abstract

Rocaglamide (1) is the parent cyclopenta[b]benzofuran derivative which was first identified as an antileukemic agent from the dried roots and stems of Aglaia elliptifolia Merr. (family Meliaceae) in 1982. Based on these findings, phytochemical interest in this genus increased sharply and up to date, more than 100 rocaglamide-type (= flavagline) compounds and structurally related derivatives have been identified from over 30 Aglaia species. Rocaglamide-type compounds show pronounced pharmacological activities including primarily (but not exclusively) antiproliferative and anti-inflammatory activity. The molecular mechanisms underlying these activities have been elucidated in recent years and established rocaglamide and several of its derivatives as interesting candidates for drug development especially in the field of anti-cancer research. Due to their unique structural features and promising pharmacological activities, several strategies leading to total synthesis of enantiomeric rocaglamide derivatives were developed and optimized. This chapter reviews the chemistry and biology of the rocaglamide-type derivatives and related compounds, with emphasis on their structural diversity, biosynthesis, pharmacological significance and total synthesis.

Keywords

Insecticidal Activity Relative Configuration Excited State Intramolecular Proton Transfer Reductive Cyclization Methyl Cinnamate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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Notes

Acknowledgements

Preparation of this chapter was supported by a grant of BMBF (to P.P.). A scholarship granted and financed by the Egyptian government (predoctoral fellowship for S.S.E.) is gratefully acknowledged.

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Copyright information

© Springer-Verlag/Wien 2011

Authors and Affiliations

  • Sherif S. Ebada
    • 1
    • 2
  • Neil Lajkiewicz
    • 3
  • John A. PorcoJr.
    • 3
  • Min Li-Weber
    • 4
  • Peter Proksch
    • 1
  1. 1.Institute of Pharmaceutical Biology and BiotechnologyHeinrich-Heine University of DuesseldorfDuesseldorfGermany
  2. 2.Department of Pharmacognosy and Phytochemistry, Faculty of PharmacyAin-Shams UniversityCairoEgypt
  3. 3.Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU)Boston UniversityBostonUSA
  4. 4.Tumor Immunology Program (D030)German Cancer Research Center (DKFZ)HeidelbergGermany

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