Phenylpropanoid Metabolism

Phenylpropanoid compounds encompass a wide range of structural classes with diverse biological functions; their biosynthesis is associated with normal plant development and is regulated by diverse environmental stimuli. Phenylpropanoid metabolism occupies a central place in the general aromatic metabolism of plants.

Keywords: shikimate pathway; hydroxycinnamic acids; coumarins; lignins; lignans

Scheme 1. The shikimate pathway enzymes: (1) 3-deoxy-d-arabino-heptulosonate 7-phosphate (DAHP); (2) 3-dehydroquinate (DHQ) synthase; (3) 3-dehydroquinate dehydratase; (4) shikimate oxidoreductase; (5) shikimate kinase; (6) 5-enol-puruvylshikimate 3-phosphate synthase; (7) chorismate synthase; (8) chorismate mutase; (9) prephenate aminotransferase; (10) arogenate dehydratase; (11) arogenate dehydrogenase; (12) anthranilate synthase; (13) anthranilate P-ribosyltransferase; (14) P-ribosylanthranilate isomerase; (15) indole 3-glycerol-P synthase; (16) tryptophan synthase; P, H2PO3.
Scheme 2. The hydroxycinnamic acids and their derivatives: (1) phenylalanine ammonia-lyase; (2) cinnamate 4-hydroxylase; (3) 4-coumarate 3-hydroxylase; (4) caffeic/5-hydroxyferulic bispecific O-methyltransferase; (5) ferulate 5-hydroxylase.
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 References
    Boudet AM (1998) A new view of lignification. Trends in Plant Science 3: 67–71.
    book Brown SA (1981) "Coumarins". In: Conn EE (ed.) The Biochemistry of Plants, vol. 7. Natural Products, pp. 269–300. New York: Academic Press.
    Davin LB, Wang HB, Crowell AL et al. (1997) Stereoselective bimolecular phenoxy radical coupling by an auxillary (dirigent) protein without an active center. Science 275: 362–366.
    Dewick PM (1993) The biosynthesis of shikimate metabolites. Natural Product Reports 9: 233–263.
    Gang DR, Costa MA, Fujita M et al. (1999) Regiochemical control of monolignol radical coupling: a new paradigm of lignin and lignan biosynthesis. Chemistry and Biology 6: 143–151.
    book Grossbard E and Atkinson D (1986) The Herbicide Glyphosate. London: Butterworths.
    Hatton D, Sablowski R, Yung MH, Smith C, Schuch W and Bevan M (1995) Two classes of cis sequences contribute to tissue-specific expression of a PAL2 promoter in transgenic tobacco. Plant Journal 7: 859–876.
    book Ibrahim RK and Barron D (1989) "Phenylpropanoids". In: Harborne JB (ed.) Methods in Plant Biochemistry, vol. 1, pp. 75–111. London: Academic Press.
    Klessig DF and Malamy J (1994) The salicylic acid signal in plants. Plant Molecular Biology 26: 1439–1458.
    book Lewis NG and Davin LB (1999) "Lignans: biosynthesis and function". In: Barton D and Nakanishi K (eds) Comprehensive Natural Products Chemistry, vol. 1, pp. 639–712. Amsterdam: Elsevier.
    Molgaard P and Ravn H (1988) Evolutionary aspects of caffeoyl ester distribution in dicotyledons. Phytochemistry 27: 2411–2421.
    book Murray R, Méndez DH and Brown SA (1982) The Natural Coumarins: Occurrence, Chemistry and Biochemistry. New York: Wiley.
    Rasmussen S and Dixon RA (1999) Transgene-mediated and elicitor-induced perturbation of metabolic channeling at the entry point into the phenylpropanoid pathway. Plant Cell 11: 1537–1551.
    Razal RA, Ellis S, Singh S, Lewis NG and Towers GHN (1996) Nitrogen recycling in phenylpropanoid metabolism. Phytochemistry 41: 31–35.
    Schuster B and Rétey J (1995) The mechanism of action of phenylalanine ammonia-lyase. Proceedings of the National Academy of Sciences of the USA 92: 8433–8437.
    Shintani D and DellaPenna D (1998) Elevating the vitamin E content of plants through metabolic engineering. Science 282: 2098–2100.
    Tamagnone L, Merida A, Parr A et al. (1998) The AmMYB308 and AmMYB330 transcription factors from Antirrhinum regulate phenylpropanoid and lignin biosynthesis in transgenic tobacco. Plant Cell 10: 135–154.
 Further Reading
    Bentley R (1990) The shikimate pathway – a metabolic tree with multiple branches. Critical Reviews in Biochemistry and Molecular Biology 25: 307–384.
    book Conn EE (ed.) (1981) The Biochemistry of Plants, vol. 7, Natural Products, chaps. 10, 11, 13, 15, 20, 22, 23. New York: Academic Press.
    Harborne JB (1989) Recent advances in chemical ecology. Natural Product Reports 6: 85–109.
    Hermann KM (1995) The shikimate pathway: early steps in the biosynthesis of aromatic amino acids. Plant Cell 7: 907–919.
    book Lewis NG and Davin LB (1999) "Lignans: biosynthesis and function". In: Barton D and Nakanishi K (eds) Comprehensive Natural Products Chemistry, vol. 1, pp. 639–712. Amsterdam: Elsevier.
    Lewis NG and Yamamoto E (1990) Lignin: occurrence, biogenesis and biodegradation. Annual Review of Plant Physiology and Plant Molecular Biology 41: 455–496.
    book Lewis NG, Davin LB and Sarkanen S (1999) "The nature and functions of lignins". In: Barton D, Nakanishi K and Meth-Cohn J (eds) Comprehensive Natural Products Chemistry, vol. 3, pp. 617–745. Amsterdam: Elsevier.
    book Luckner M (1990) Secondary Metabolism in Microorganisms, Plants and Animals. Berlin: Springer-Verlag.
    Martin C and Pas-Ares J (1997) MYB transcription factors in plants. Trends in Genetics 13: 67–73.
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Ibrahim, Ragaï K(Apr 2001) Phenylpropanoid Metabolism. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1038/npg.els.0001912]