Flavaglines are a family of natural products that are found in plants of the genus Aglaia (Meliaceae). These compounds are characterized by a cyclopenta[b]benzofuran skeleton. In 1982 King and colleagues discovered the first member of this family, rocaglamide, based on its antileukemic activity.[1] Since then, about 50 other flavaglines have been characterized. These molecules display strong insecticidal, antifungal, anti-inflammatory, neuroprotective, cardioprotective and anticancer activities.[2][3] In mouse models of cancer, flavaglines enhance the efficacy of chemotherapies[4][5] and also alleviate the cardiac adverse effect of these chemotherapies.[6]
The challenge raised by their structural complexity has attracted the attention of some organic chemists. In 1990, Barry Trost presented an enantioselective synthesis of rocaglamide in 18 steps and confirmed its absolute configuration.[7]
^King, M. L.; Chiang, C. C.; Ling, H. C.; Fujita, E.; Ochiai, M.; McPhail, A. T. "X-Ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia". J Chem Soc Chem Commun. 1982: 1150–1151.
^Ebada, S. S.; Lajkiewicz, N.; Porco, J. A. Jr.; Li-Weber, M.; Proksch, P. (2011). "Chemistry and biology of rocaglamides (= flavaglines) and related derivatives from aglaia species (meliaceae)". Fortschr Chem Org Naturst. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. 94: 1–58. doi:10.1007/978-3-7091-0748-5_1. ISBN978-3-7091-0747-8. PMC4157394. PMID 21833837.
^Ribeiro, N.; Thuaud, F.; Nebigil, C.; Désaubry, L., Recent advances in the biology and chemistry of the flavaglines. Bioorg Med Chem 2012, in press.
^Bordeleau, M. E.; Robert, F.; Gerard, B.; Lindqvist, L.; Chen, S. M.; Wendel, H. G.; Brem, B.; Greger, H.; Lowe, S. W.; Porco, J. A. Jr.; Pelletier, J. (2008). "Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model" (PDF). J Clin Invest. 118 (7): 2651–60. doi:10.1172/JCI34753. PMC2423864. PMID 18551192.
^Zhu, J. Y.; Giaisi, M.; Kohler, R.; Muller, W. W.; Muhleisen, A.; Proksch, P.; Krammer, P. H.; Li-Weber, M. (2009). "Rocaglamide sensitizes leukemic T cells to activation-induced cell death by differential regulation of CD95L and c-FLIP expression". Cell Death Differ. 16 (9): 1289–99. doi:10.1038/cdd.2009.42. PMID 19373244.
^Trost, B. M.; Greenspan, P. D.; Yang, B. V.; Saulnier, M. G. (1990). "An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of (−)-rocaglamide". J Am Chem Soc. 112 (24): 9022–4. doi:10.1021/ja00180a081.
January 01, 1970
flavagline, family, natural, products, that, found, plants, genus, aglaia, meliaceae, these, compounds, characterized, cyclopenta, benzofuran, skeleton, 1982, king, colleagues, discovered, first, member, this, family, rocaglamide, based, antileukemic, activity. Flavaglines are a family of natural products that are found in plants of the genus Aglaia Meliaceae These compounds are characterized by a cyclopenta b benzofuran skeleton In 1982 King and colleagues discovered the first member of this family rocaglamide based on its antileukemic activity 1 Since then about 50 other flavaglines have been characterized These molecules display strong insecticidal antifungal anti inflammatory neuroprotective cardioprotective and anticancer activities 2 3 In mouse models of cancer flavaglines enhance the efficacy of chemotherapies 4 5 and also alleviate the cardiac adverse effect of these chemotherapies 6 Chemical structure of the flavagline FL3 The challenge raised by their structural complexity has attracted the attention of some organic chemists In 1990 Barry Trost presented an enantioselective synthesis of rocaglamide in 18 steps and confirmed its absolute configuration 7 See also editFL3 flavagline Rocaglamide Silvestrol AglafolineReferences edit King M L Chiang C C Ling H C Fujita E Ochiai M McPhail A T X Ray crystal structure of rocaglamide a novel antileukemic 1H cyclopenta b benzofuran from Aglaia elliptifolia J Chem Soc Chem Commun 1982 1150 1151 Ebada S S Lajkiewicz N Porco J A Jr Li Weber M Proksch P 2011 Chemistry and biology of rocaglamides flavaglines and related derivatives from aglaia species meliaceae Fortschr Chem Org Naturst Fortschritte der Chemie organischer Naturstoffe Progress in the Chemistry of Organic Natural Products 94 1 58 doi 10 1007 978 3 7091 0748 5 1 ISBN 978 3 7091 0747 8 PMC 4157394 PMID 21833837 Ribeiro N Thuaud F Nebigil C Desaubry L Recent advances in the biology and chemistry of the flavaglines Bioorg Med Chem 2012 in press Bordeleau M E Robert F Gerard B Lindqvist L Chen S M Wendel H G Brem B Greger H Lowe S W Porco J A Jr Pelletier J 2008 Therapeutic suppression of translation initiation modulates chemosensitivity in a mouse lymphoma model PDF J Clin Invest 118 7 2651 60 doi 10 1172 JCI34753 PMC 2423864 PMID 18551192 Zhu J Y Giaisi M Kohler R Muller W W Muhleisen A Proksch P Krammer P H Li Weber M 2009 Rocaglamide sensitizes leukemic T cells to activation induced cell death by differential regulation of CD95L and c FLIP expression Cell Death Differ 16 9 1289 99 doi 10 1038 cdd 2009 42 PMID 19373244 Bernard Y Ribeiro N Thuaud F Turkeri G Dirr R Boulberdaa M Nebigil C Desaubry L 2011 Flavaglines Alleviate Doxorubicin Cardiotoxicity Implication of Hsp27 PLoS ONE 6 10 e25302 Bibcode 2011PLoSO 625302B doi 10 1371 journal pone 0025302 PMC 3204970 PMID 22065986 Trost B M Greenspan P D Yang B V Saulnier M G 1990 An unusual oxidative cyclization A synthesis and absolute stereochemical assignment of rocaglamide J Am Chem Soc 112 24 9022 4 doi 10 1021 ja00180a081 Retrieved from https en wikipedia org w index php title Flavagline amp oldid 1218530154, wikipedia, wiki, book, books, library,
