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CHEM-705 Biosynthesis of Natural Products Set C February - 2014 1.

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Presentation on theme: "CHEM-705 Biosynthesis of Natural Products Set C February - 2014 1."— Presentation transcript:

1 CHEM-705 Biosynthesis of Natural Products Set C February - 2014 1

2 CHEM-705 Biosynthesis of Natural Products Set C Eighth-Twelveth Lectures Prof. Dr. Shaheen Faizi 2014 2

3 ALLAH is He Who has made perfect every thing he has created. (32:8) Our Lord is He Who gave unto everything its proper form and then guided it to its proper functions. (20:51) 3

4 The Biosynthesis of Shikimate metabolites 4

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38 1L. M. Poduct and D. H. Sherman, Diversity of P450 enzymes in the biosynthesis of natural products, Nat. Prod. Rep., 2012, 29, 1251-1266. 2N. C. Veitch and. R. J. Grayer, Flavonoids and their glycosides, including anthocyanins, Nat. Prod. Rep., 2011, 28, 1626-1695. 3R. Tsao, Chemistry and biochemistry of dietary polyphenols, Nutrie., 2010, 2, 1231-1246. 4K. Yoshida, M. Mori and T. Kondo, Blue flower color development by anthocyanins: from chemical structure to cell physiology, Nat. Prod. Rep., 2009, 26, 884-915. 5N. Erkan, Huseyin Cetin, E. Ayranci, Antioxidant activities of Sideritis congesta Davis et Huber-morath and Sideritis arguta boiss et heldr: Identification of free flavonoids and cinamic acid derivatives, Food Res. Inter., 2011, 44, 297-303. 6K. Nagy, K. Redeuil, G. Williamson, S. Rezzi, F. Dionisi, K. Longet, F. Destaillats, M. Renouf, First identification of dimethoxycinnamic acids in human plasma after coffee intake by liquid chromatography-mass spectrometry, J. Chromatog., 2011, 1218, 491-497. 7E. S.-Rodriquez, D. A. Moreno, F. Ferreres, M. D. M. R.-Wilhelmi, J. M. Ruiz, Differential responses of five cherry tomato varieties to water stress: changes on phenolic metabolites and related enzymes, Phytochem., 2011, 72, 723-729. 8X. Dong, T. Liu, J. Yan, P. Wu, J. Chen, Y. Hu, Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents, Bioorg. Med. Chem., 2009, 17, 716-726. 9S. Protti, A. Mezzetti, C. Lapouge and J.-P. Cornard, Photochemistry of metal complexes of 3-hydroxyflavone: towards a better understanding of the influence of solar light on the metal-soil organic matter interactions, Photochem. Photobiol. Sci., 2008, 7, 109-119. 10A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 2003, 20, 119-136. A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 2001, 18, 334-355. A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 2000, 17, 269-292. A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 1999, 16, 525-560. 38

39 11Flavonoid Biosynthesis, Nat. Prod. Rep., 2000, 17, 376. 12L. B. Davin, M. Jourdes, A. M. Patten, K. W. Kim, D. G. Vassao and N. G. Lewis, Processes in allyl/propenyl phenol and lignin biosynthesis, Nat. Prod. Rep., 2008, 25, 1015-1090. bA. Crozier, I. B. Jaganath and M. N. Clifford, Dietary phenolics : chemistry bioavailability and effects on health, Nat. Prod. Rep., 2009, 26, 1001-1043. 13N. C. Veitch and R. J. Grayer, Flavonoids and their glycosides, including anthocyannins, Nat. Prod. Rep., 2008, 25, 555-611. 14S. E. Drewes, S. F. van Vuuren. Antimicrobial acylphloroglucinols and dibenzyloxy flavonoids from flowers of Helichrysum gymnocomum. Phytochem., 2008, 69, 1745-1749. 15C. Canela, R. M. Moraesb, F. E. Dayana, D. Ferreira, Molecules of interest podophyllotoxin, Phytochem. 2000, 54, 115-120. 16P. J. Facchini, Kara L. H. Allanach, L. W. Tari, Plant aromatic L-amino acid decarboxylases: evolution, biochemistry, regulation, and metabolic engineering applications, Phytochem. 2000, 54, 121-138. 17P. Manitto, D. Monti, G. Speranza. Evidence for an NIH-shift as the origin of the apparently anomalous distribution of deuterium in natural cstragole. J. Nat. Prod., 2000, 63, 713-715. 18J. Schmid and N. Amrhein. Molecular organization of the shikimate pathway in higher plants, Phytochem., 1995, 39, 737-749. 19 Paul M. Dewick. Medicinal natural products, a biosynthetic approach. John Wiley & Sons, 2002. 20E. Haslam, S. D. Barton, and W. D. Ollis, Comprehensive organic chemistry, Shikimic acid metabolites, volume-5, Biological Compounds, 1979. 21 Enclopedia of chemical technology. Kirk-Orthmcr. Various Vols. 22R. Thomas. Biogenetic speculation and biosynthetic advances. Nat. Prod. Rep., 2004, 21, 224-248. 39

40 23M. Fullbck, E. Miehalsky. M. Dunkel and R. Preissner. Natural products: sources and databases. Nat. Prod. Rep., 2006, 23, 347-356. 24Turnbull, J. Jonathan et al. Figures l and 3 in mechanistic studies on three 2-oxoglutaratc-dependent oxygcnases of flavonoid biosynthesis: Anthocyanidin synthase, avonol synthase, and avanone 3{ }-hydroxylase. J. Biol. Chem., 2004, 279, 1206-1216. http://www.jbc.org/cgi/reprint/279/2/1206 25Fukusaki, Ei-ichiro et al. Figures 1 and 3 in flower color modulations of Torenia hybrida by downregulation of chalcone synthase genes with RNA intcrlèrence. J. Biotech. 2004, 111, 229-240. 26Xie, De-Yu et al. Figures 3 and 2 in role of anthocyanidin reductase, encoded by 13ANYULS in plant flavonoid biosynthesis. Science, 2003, 299, 396-399. 27Winkel-Shirley, Brenda. Figure 1 in Flavonoid Biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol., 2001, 126, 485-493. http://www.plantphysiol.org/gci/content/full/126/2/485 28Hashim, M. Faisal et al. Figure 2 in reaction mechamism of oxidative rearrangement of flavanone in isoflavone biosynthesis. FEBS Lett., 1990. 271. 219-222. 29H.-X. Xu, S. F. Lee, Activity of flavonoids against antibiotic-resistant bacteria, Phyto. Res., 2001, 15, 39-43. 30T.P. T. Cushnie, A. J. Lamb, Antimicrobial activity of flavonoids, Int. J. Antimicrob. Agents, 2005, 26, 343–356. 31J. E. Bassard, P. Ullmann, F. Bernier, D. W. Reichhart, Phenolamides: Bridging polyamines to the phenolic metabolism, Phytochem., 2010, 71, 1808-1824. 32S. Martens and A. Mithöfer, Flavones and flavone synthases, Phytochem., 2005, 66, 2399-2407. 33K. H. Pee, and J. M. Ligon, Biosynthesis of pyrrolnitrin and other phenylpyrrole derivatives by bacteria, Nat. Prod. Rep., 2000, 17, 157-164. 40

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