Chemistry and Biology of Rocaglamides (= Flavaglines) and Related Derivatives from Aglaia Species (Meliaceae)
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
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Contents 1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2. Structural Classification of Rocaglamides and Related Compounds . . . . . . . . . . . . . . . . . . . . . . 2.1. Rocaglamide Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.2. Aglain Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.3. Aglaforbesin Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2.4. Forbagline Derivatives . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3. Biosynthesis of Rocaglamides and Related Metabolites . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
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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. S.S. Ebada Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University of Duesseldorf, Universitaetsstrasse 1, D-40225, Duesseldorf, Germany Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Ain-Shams University, Organization of African Unity 1, 11566 Cairo, Egypt e-mail: [email protected] N. Lajkiewicz • J.A. Porco Jr. Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Commonwealth Avenue 590, Boston, MA 02215, USA e-mail: [email protected]; [email protected] M. Li-Weber Tumor Immunology Program (D030), German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69120, Heidelberg, Germany e-mail: [email protected] P. Proksch (*) Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University of Duesseldorf, Universitaetsstrasse 1, D-40225, Duesseldorf, Germany e-mail: [email protected] A.D. Kinghorn, H. Falk, J. Kobayashi (eds.), Progress in the Chemistry of Organic Natural Products, Vol. 94, DOI 10.1007/978-3-7091-0748-5_1, # Springer-Verlag/Wien 2011
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4. Pharmacological Significance of Rocaglamides and Related Compounds . . . . . . . . . . . . . . . . 4.1. Insecticidal Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.2. Anti-inflammatory Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 4.3. Anticancer Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5. Chemical Synthesis of Cyclopenta[b
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