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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

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

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, N. C. Veitch and. R. J. Grayer, Flavonoids and their glycosides, including anthocyanins, Nat. Prod. Rep., 2011, 28, R. Tsao, Chemistry and biochemistry of dietary polyphenols, Nutrie., 2010, 2, K. Yoshida, M. Mori and T. Kondo, Blue flower color development by anthocyanins: from chemical structure to cell physiology, Nat. Prod. Rep., 2009, 26, N. 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, K. 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, E. 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, X. 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, S. 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, A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 2003, 20, A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 2001, 18, A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 2000, 17, A. R. Knaggs, The biosynthesis of shikimate metabolites, Nat. Prod. Rep., 1999, 16,

39 11Flavonoid Biosynthesis, Nat. Prod. Rep., 2000, 17, L. 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, bA. Crozier, I. B. Jaganath and M. N. Clifford, Dietary phenolics : chemistry bioavailability and effects on health, Nat. Prod. Rep., 2009, 26, N. C. Veitch and R. J. Grayer, Flavonoids and their glycosides, including anthocyannins, Nat. Prod. Rep., 2008, 25, S. E. Drewes, S. F. van Vuuren. Antimicrobial acylphloroglucinols and dibenzyloxy flavonoids from flowers of Helichrysum gymnocomum. Phytochem., 2008, 69, C. Canela, R. M. Moraesb, F. E. Dayana, D. Ferreira, Molecules of interest podophyllotoxin, Phytochem. 2000, 54, P. 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, P. 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, J. Schmid and N. Amrhein. Molecular organization of the shikimate pathway in higher plants, Phytochem., 1995, 39, Paul M. Dewick. Medicinal natural products, a biosynthetic approach. John Wiley & Sons, E. Haslam, S. D. Barton, and W. D. Ollis, Comprehensive organic chemistry, Shikimic acid metabolites, volume-5, Biological Compounds, Enclopedia of chemical technology. Kirk-Orthmcr. Various Vols. 22R. Thomas. Biogenetic speculation and biosynthetic advances. Nat. Prod. Rep., 2004, 21,

40 23M. Fullbck, E. Miehalsky. M. Dunkel and R. Preissner. Natural products: sources and databases. Nat. Prod. Rep., 2006, 23, Turnbull, 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, Fukusaki, 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, Xie, De-Yu et al. Figures 3 and 2 in role of anthocyanidin reductase, encoded by 13ANYULS in plant flavonoid biosynthesis. Science, 2003, 299, Winkel-Shirley, Brenda. Figure 1 in Flavonoid Biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol., 2001, 126, Hashim, M. Faisal et al. Figure 2 in reaction mechamism of oxidative rearrangement of flavanone in isoflavone biosynthesis. FEBS Lett., H.-X. Xu, S. F. Lee, Activity of flavonoids against antibiotic-resistant bacteria, Phyto. Res., 2001, 15, T.P. T. Cushnie, A. J. Lamb, Antimicrobial activity of flavonoids, Int. J. Antimicrob. Agents, 2005, 26, 343– J. E. Bassard, P. Ullmann, F. Bernier, D. W. Reichhart, Phenolamides: Bridging polyamines to the phenolic metabolism, Phytochem., 2010, 71, S. Martens and A. Mithöfer, Flavones and flavone synthases, Phytochem., 2005, 66, K. H. Pee, and J. M. Ligon, Biosynthesis of pyrrolnitrin and other phenylpyrrole derivatives by bacteria, Nat. Prod. Rep., 2000, 17,

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