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

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Book cover Progress in the Chemistry of Organic Natural Products Vol. 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.

John A. Porco, Min Li-Weber, and Peter Proksch contributed equally to the writing of this chapter. Dedicated to Dr. Bambang Wahyu Nugroho, a pioneer of rocaglamide research (9, 14, 16, 17, 27, 54–56, 58, 59, 75, 84, 85) who passed away far too early.

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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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Authors and Affiliations

  1. Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University of Duesseldorf, Universitaetsstrasse 1, D-40225, Duesseldorf, Germany

    Sherif S. Ebada & Peter Proksch

  2. Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Ain-Shams University, Organization of African Unity 1, 11566, Cairo, Egypt

    Sherif S. Ebada

  3. Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Commonwealth Avenue 590, Boston, MA, 02215, USA

    Neil Lajkiewicz & John A. Porco Jr.

  4. Tumor Immunology Program (D030), German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69120, Heidelberg, Germany

    Min Li-Weber

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  1. Sherif S. Ebada
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  4. Min Li-Weber
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Correspondence to Peter Proksch .

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  1. College of Pharmacy, Div. Medicinal Chemistry &, Ohio State University, West 12th Ave. 500, Columbus, 43210, Ohio, USA

    A. Douglas Kinghorn

  2. Leonfeldner Str. 150, Linz, 4040, Austria

    Heinz Falk

  3. Graduate School of Medical Sciences, Dept. Developmental, Kyushu University, Maidashi 3-1-1, Fukuoka, 812-8582, Japan

    Junichi Kobayashi

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Ebada, S.S., Lajkiewicz, N., Porco, J.A., Li-Weber, M., Proksch, P. (2011). Chemistry and Biology of Rocaglamides (= Flavaglines) and Related Derivatives from Aglaia Species (Meliaceae). In: Kinghorn, A., Falk, H., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products Vol. 94. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 94. Springer, Vienna. https://doi.org/10.1007/978-3-7091-0748-5_1

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