Recent Work on Cinnamoyl CoA Derivatives

  • M. H. Zenk
Part of the Recent Advances in Phytochemistry book series (RAPT, volume 12)


The rapid increase in knowledge of biochemical events in primary metabolism in the 1950’s have enabled biochemists and physiologists to tackle the difficult problems involved in plant secondary metabolism over the last decade. Due to isotope incorporation studies which laid the basis of our present knowledge, biosynthetic reactions were postulated in plant secondary metabolism by analogy with established pathways in primary metabolism. It was, therefore, logical that reactions in plant phenolic metabolism involving carboxyl activation were though to involve coenzyme A thiolesters; analogous to reactions known in acetate and malonate metabolism.


Ferulic Acid Cell Suspension Culture Chlorogenic Acid Cinnamic Acid Shikimic Acid 
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  1. 1.
    Al-Arif, A. and M. Blech. 1969. Synthesis of fatty acyl CoA and other thiolesters using N-hydroxysuccinimide esters of fatty acids. J. Lipid Res.10: 344–45.PubMedGoogle Scholar
  2. 2.
    Alibert, G. and R. Ranjeva. 1971. Recherches sur catalysant la biosynthese des acides phenoliques Chezquercus pedunculata(Ehrh): I. Formation des premiers termes des series cinnamique et benzoique. FEBS Lett.19: 11–14.PubMedCrossRefGoogle Scholar
  3. 3.
    Alibert, G., R. Ranjeva and A. Boudet. 1972. II. Localisation intracellulaire de la phenylalanine ammoniaque-lyase, de la cinnamate 4-hydroxylase, et de la “benzoate synthase”. Biochim. Biophys. Acta279: 282–89.PubMedCrossRefGoogle Scholar
  4. 4.
    Amrhein N. and M. H. Zenk. 1970. Concomitant induction of phenylalanine ammonialyase and cinnamic acid 4-hyroxylase during illumination of excised buckwheat hypocotyls. Naturwissenschaften57: 312.CrossRefGoogle Scholar
  5. 5.
    Barenholz, Y., I. Edelman, and S. Gatt. 1974. Amine: acetyl coenzyme A acetyl transferase from the soluble fraction ofHansenula ciferri: Isolation and properties. Biochim. Biophys. Acta358: 262–74.CrossRefGoogle Scholar
  6. 6.
    Berlin, J. and W. Barz. 1975. Oxidative decarboxylation of para-hydroxybenzoic acids by peroxidase under tovivoandvitroconditions. Z. Naturforsch.30c: 650–58.Google Scholar
  7. 7.
    Billek, G. and F. P. Schmook. 1966, Biosynthese der Benzoesauren. Osterr. Chemiker Zeitung67: 401–09.Google Scholar
  8. 8.
    Birch, A. J. and F. W. Donovan. 1953. Studies in relation to biosynthesis. I. some possible routes to derivatives of orcinol and phloroglucinol. Austr. J. Chem.6: 360–68.CrossRefGoogle Scholar
  9. 9.
    Brown, S. A., D. Wright and A. C. Neish. 1959. Studies of lignin biosynthesis using isotopic carbon. VII. The role of p-hydroxyphenylpyruvic acid. Can. J. Biochem. Physiol.37:25–34.PubMedCrossRefGoogle Scholar
  10. 10.
    Brown, S. A. 1966. Lignins. Ann. Rev. Plant Physiol.17: 223–44.CrossRefGoogle Scholar
  11. 11.
    Cartwright, N. J. and A. R. W. Smith. 1967. Bacterial attack on phenolic ethers & enzyme system demethylating vanillic acid. Biochein J.102: 826–41.Google Scholar
  12. 12.
    Davie, E. W., V. V. Koningsberger and F. Lipmann.1956. The isolation of tryptophan-activating enzyme from pancreas. Arch. Biochem. Biophys.65:21–38.PubMedCrossRefGoogle Scholar
  13. 13.
    Dekker, K. 1959. Die aktivierte Essigsaure. Ferdinand Enke-Verlag, Stuttgart.Google Scholar
  14. 14.
    Ebel, J. and H. Grisebach. 1973. Reduction of cinnamic acids to cinnamoyl alcohols with an enzyme preparation from cell suspension cultures of soybean (Glycine max.). FEBS Lett.30: 141–43.PubMedCrossRefGoogle Scholar
  15. 15.
    El-Basyouni, S. Z. and A. C. Neish. 1966. Occurrence of metabolically-active bound forms of cinnamic acid and its phenolic derivatives in acetone powders of wheat and barley plants. Phytochemistry5: 683–91.CrossRefGoogle Scholar
  16. 16.
    Enzyme Nomenclature. 1973. Elsevier Press, Amsterdam.Google Scholar
  17. 17.
    Floss, H. G. and A. Rettig. 1964. Biosyntheseversuche mit Gentianaceae. I. Biosynthese des Gentisins. Z. Naturforsch.19b: 1103–05.Google Scholar
  18. 18.
    French, C. J., C. P. Vance and G. H. N. Towers. 1976. Conversion of p-coumaric acid to p-hydroxybenzoic acid by cell-free extracts of potato tubers andPolyporus hispidus. Phytochemistry15: 564–66CrossRefGoogle Scholar
  19. 19.
    Grisebach, H. 1962. The biosynthesis of flavonoids. Planta medica10: 385–97.CrossRefGoogle Scholar
  20. 20.
    Grisebach, H., W. Barz, K. Hahlbrock, S. Kellner and L. Patschke. 1966. Recent investigation on the biosynthesis of flavonoids. In: Billek, G. ed., Biosynthesis of aromatic compounds. Proceedings of the 2nd meeting of the Federation of European Biochemical Societies, Oxford, Pergamon Press, Vol. 3, p. 25–36.Google Scholar
  21. 21.
    Grisebach, H. and W. Barz. 1969. Biochemie der Flav onoide. Naturwissenschaften56: 538–44.PubMedCrossRefGoogle Scholar
  22. 22.
    Gross, G. G. and M. H. Zenk. 1966. Darstellung und Eigenschaften von Coenzyme A-thiolestern substituierter Zimtsauren. Z. Naturforsch.21b:683–90.Google Scholar
  23. 23.
    Gross, G. G., J. Stockigt, R. L. Hansell, and M. H. Zenk. 1973. Three novel enzymes involved in the reduction of ferulic acid to coniferyl alcohol in higher plants: Ferulate: CoA ligase, feruloyl-CoA reductase and coniferyl alcohol oxidoreductase. FEBS Lett.31: 283–86.CrossRefGoogle Scholar
  24. 24.
    Gross, G. G. and M. H. Zenk. 1974. Isolation and properties of hydroxycinnamate: CoA ligase from lignifying tissue ofForsythia. Eur. J. Biochem.42: 453–59.PubMedCrossRefGoogle Scholar
  25. 25.
    Gross, G. G., R. L. Hansell, and H. H. Zenk. 1975. Hydroxycinnamate:coenzyme A ligase from lignifying tissue of higher plants. Some properties and taxonomic distribution. Biochem. Physiol. Pflanzen168: 41–51.Google Scholar
  26. 25a.
    Gross, G. G. and W. Kreiten. 1975. Reduction of coenzyme A. Thiolesters of cinnamic acids with an enzyme preparation from lignifying tissue ofForsythia. FEBS Lett.54: 259–62.PubMedCrossRefGoogle Scholar
  27. 26.
    Gross, G. G. 1977. Biosynthesis of lignin and related monomers. In: The Structure, Biosynthesis and Degradation of Wood. Loewus, F. A. and V. C. Runeckles, eds. Recent Advances in Phytochemistry Vol. 11, p. 141–84.CrossRefGoogle Scholar
  28. 27.
    Hagel, P. and H. Kindl. 1975. p-Hydroxybenzoate synthase: A complex associated with mitochondrial membranes of roots ofCucumis sativus. FEBS Lett.59: 120–24.PubMedCrossRefGoogle Scholar
  29. 28.
    Hanson, K. R. 1966. Chlorogenic acid biosynthesis incorporation of (β–14C) cinnamic acid into the cinnamoyl and hydroxycinnamoyl conjugates of the potato tuber. Phytochemistry5: 491–99.CrossRefGoogle Scholar
  30. 29.
    Harborne, J. B., T. J. Mabry and H. Mabry. 1975. The Flavonoids. Chapman and Hall, London.Google Scholar
  31. 30.
    Haslam, E. 1974. The Shikimate Pathway. Butterworths, London.Google Scholar
  32. 31.
    Heinzmann, U., U. Seitz, and U. Seitz. 1977. Purification and subsrate specificities of hydroxycin- namate: CoA ligase from anthocyanin-containing and anthocyanin-free carrot cells. Planta135: 313–18.CrossRefGoogle Scholar
  33. 32.
    Hess, D. 1968. Biochemische Genetik. Springer Verlag, Berlin.CrossRefGoogle Scholar
  34. 33.
    Higuchi, T. and S. A. Brown. 1963. Studies of lignin biosynthesis using isotopic carbon. VIII. The phenylpropanoid system in lignification. Can. J. Biochem. Physiol.41:621–28.PubMedCrossRefGoogle Scholar
  35. 34.
    Hrazdina, G., F. Kreuzaler, K. Hahlbrock and H. Grisebach. 1976. Substrate specificity of flavanone synthase from cell suspension cultures of parsley and structure of release productsvitroArch. Biochem. Biophys.175: 392–99.Google Scholar
  36. 35.
    Johns, N. 1974. Synthesis and characterisation of acyl coenzyme A derivatives of aromatic carboxy- lic acids, z. Naturforsch.29c: 469–74.Google Scholar
  37. 36.
    Kindl, H. and H. Ruis. 1971. Subcellular distribution of p-hydroxybenzoic acid formation in castor bean endosperm. Z. Naturforsch.26b: 1379–80.Google Scholar
  38. 36a.
    Knobloch, K. H. and K. Hahlbrock. 1975. Isoenzymes of p-coumarate:CoA ligase from cell suspension cultures ofGlycine max. Eur. J. Biochem.52: 311–20.PubMedCrossRefGoogle Scholar
  39. 37.
    Kreuzaler, F. and K. Hahlbrock. 1972. Enzymatic synthesis of aromatic compounds in higher plants: formation of naringenin (5,7,4’-trihydroxy-flav- anone) from p-coumaroyl coenzyme A and malonyl coenzyme A. FEBS Lett.28:69–72.PubMedCrossRefGoogle Scholar
  40. 38.
    Kreuzaler, F. and K. Hahlbrock. 1975. Partial purification and some properties of flavanone synthase from cell suspension cultures ofPetroselinum hortense. Eur. J. Biochem.56: 205–13.PubMedCrossRefGoogle Scholar
  41. 39.
    Kreuzaler, F. and K. Hahlbrock. 1975. Enzymatic synthesis of aromatic compounds in higher plants. Formation of bis-noryangonin ((4-hydroxy–6(4-hy- droxystyrl)–2-pyrone)) from p-coumaroyl-CoA and malonyl-CoA. Arch. Biochem. Biophys.169: 84–90.PubMedCrossRefGoogle Scholar
  42. 40.
    Lamb, C. J. 1977. trans-Cinnamic acid as a mediator of the light-stimulated increase in hydroxycinna- moyl-CoA:quinate hydroxycinnamoyl transferase. FEES Lett.75: 37–40.CrossRefGoogle Scholar
  43. 41.
    Lindl, T., F. Kreuzler, and K. Hahlbrock. 1973. Synthesis of p-coumaroyl coenzyme A with a partially purified p-coumarate:CoA ligase from cell suspension cultures of soybean (Glycine max.). Biochim. Biophys. Acta302: 457–64.PubMedCrossRefGoogle Scholar
  44. 42.
    Lipmann, F. and L. C. Tuttle 1945. A specific micro-method for the determination of acyl phosphates. J. Biol. Chem.159: 21–28.Google Scholar
  45. 43.
    Loffelhardt, W. and H. Kindl. 1975. The conversion of L-phenylalanine into benzoic acid on the thy- lakoid membrane of higher plants. H-S. Z. Physiol. Chem.356:487–93.CrossRefGoogle Scholar
  46. 44.
    Loffelhardt, W. and H. Kindl. 1976. Formation of benzoic acid and p-hydroxybenzoic acid in the blue green algaAnacystis nidulans: A thylakoid- bound enzyme complex analogous to the chloroplast system. Z. Naturforsch.31c: 693–99.Google Scholar
  47. 45.
    Mahler, H. R., S. J. Wakil and R. M. Bock. 1953. Studies on fatty acid oxidation. I. Enzymatic activation of fatty acids. J. Biol. Chemistry204: 453–68.Google Scholar
  48. 46.
    Majak, W. and G. H. N. Towers. 1973. Incorporation of14CO214C-phenylalanine14 of CO,14C-phenylalanine and C-cinnamate into soluble and insoluble cinnamic derivatives inMentha arvensis. Phytochemistry12: 2189–95.CrossRefGoogle Scholar
  49. 47.
    Mansell, R. L., J. Stockigt and M. H. Zenk. 1972. Reduction of ferulic acid to coniferyl alcohol in a cell-free system from a higher plant. Z. Pflanzenphysiol.68: 286–88.Google Scholar
  50. 48.
    Murakoshi, I., K. Sugimoto, J. Haginiwa, S. Ohmiya, and H. Otomasu. 1975. (-)-(trans–4’-hydroxycinnamoyl] lupinine, a new alkaloid inLupinusseedlings. Phytochemistry14: 2714–15.CrossRefGoogle Scholar
  51. 49.
    Murakoshi, I., M. Ogawa, K. Toriizuka, J. Haginiwa, S. Ohmiya and H. Otomasu. 1977. The enzymatic conversion of (-) lupinine to (-)-(trans–4’-hy- droxycinnamoyDlupinine by extracts ofLupinusseedlings. Chem. Pharm. Bull.25:527–29.CrossRefGoogle Scholar
  52. 50.
    Nagels, L. and F. Parmentier. 1976. Kinetic study of possible intermediates in the biosynthesis of chlorogenic acid inOestrum poeppigu. Phytochemistry15: 703–96.CrossRefGoogle Scholar
  53. 51.
    Neish, A. C. 1959. Biosynthesis of pungenin from C-labelled compounds by Colorado spruce. Can. J. Bot.37:1085–00.CrossRefGoogle Scholar
  54. 52.
    Neish, A. C. 1964. Cinnamic acid derivatives as inter mediates in the biosynthesis of lignin and related compounds. In: The Formation of Wood in Forest Trees (M. H. Zimmermann, ed.), pp. 219–39. Academic Press. New York, London.Google Scholar
  55. 53.
    Ranganathan, S. and T. Ramasarma. 1971. Enzymatic formation of p-hydroxybenzoate from p-hydroxycinnamate. Biochem. J.122: 487–493.PubMedGoogle Scholar
  56. 54.
    Ranjeva, R. and R. Faggion. 1975. Metabolisme des composes phenoliques des tissue dePetunia. III. Physiol. Veg.13: 735–42.Google Scholar
  57. 54a.
    Ranjeva, R., A. M. Boudet and R. Faggion. 1976. Phenolic metabolism inPetuniatissue. IV. Properties of p-coumarate:coenzyme A Ligase isoenzymes. Biochimie,58:1255–62PubMedCrossRefGoogle Scholar
  58. 55a.
    Rhodes, M. J. C. and L. S. C. Wooltorton. 1973. Formation of CoA esters of cinnamic acid derivatives by extracts ofBrassica napo-brassicaroot tissue. Phytochemistry12: 2381–87.CrossRefGoogle Scholar
  59. 55.
    Rhodes, M. J. C. and L. S. C. Wooltorton. 1975. Enzymes involved in the reduction of ferulic acid to coniferyl alcohol during the aging of disks of swede root tissue. Phytochemistry14: 1235–40.CrossRefGoogle Scholar
  60. 56.
    Rhodes, M. J. C., A. C. R. Hill, and L. S. C. Wooltorton. 1976. Activity of enzymes involved in lignin biosynthesis in swede root disks. Phytochemistry 15: 707–10.CrossRefGoogle Scholar
  61. 57.
    Rhodes, M. J. C. and L. S. C. Wooltorton. 1976.The enzymic conversion of hydroxycinnamic acids to p-coumarylquinic and chlorogenic acid in tomato fruits. Phytochemistry25: 947–51.CrossRefGoogle Scholar
  62. 58.
    Saylor, M. H. and R. L. Hansell. 1977. Hydroxycinna-moyl: Coenzyme. A transferase involved in the biosynthesis of kaempferol–3-(p-coumaroyltriglu- coside) inPisum sativum. Z. Naturforsch.32c: in press.Google Scholar
  63. 59.
    Seiler, N. and M. J. Al-Therib. 1974. Acetyl-CoA: 1,4-diaminobutane-N-acetyltransferase. Biochim. Biophys. Acta.354: 206–12.PubMedCrossRefGoogle Scholar
  64. 60.
    Subba-Rao, P. V., A. M. D. Nambudiri and J. V. Bhat. 1971. Microbial degradation of phenylpropanoid compounds. J. Scient. Indust. Research30: 663–79.Google Scholar
  65. 61.
    Sumere, Van C F., H. de Footer, H. Ali and M. D. van Bussel. 1973. N-Feruloylglycyl-L-phenyla- lanine: A sequence in barley proteins. Phytochemistry12: 407–11.CrossRefGoogle Scholar
  66. 62.
    Sutfeld, R. and R. Wiermann. 1976. The formation of flavanones from hydroxycinnamoyl coenzyme A thiolesters and malonyl-CoA by enzyme extracts from anthers. Z.Pflanzenphysiol.79: 467–72.Google Scholar
  67. 63.
    Schachter, D. and J. V. Taggart. 1953. Benzoyl-CoA and hippurate synthesis. J. Biol. Chem.203: 925–34.PubMedGoogle Scholar
  68. 64.
    Schachter, D. and J. V. Taggart. 1954. Glycine N-acylase: Purification and properties. J. Biol. Chemistry,208:263–75.Google Scholar
  69. 65.
    Stafford, H. A. 1974. The metabolism of aromatic compounds. In: Ann. Rev. Plant Physiol.25: 459–86.CrossRefGoogle Scholar
  70. 66.
    Stockigt, J., R. L. Hansell, G. G. Gross and M. H. Zenk. 1973. Enzymic reduction of p-coumaric acid via p-coumaroyl-CoA to £-coumaryl alcohols by a cell-free system fromForsythiasp. Z. Pflanzenphysiol.70: 305–07.Google Scholar
  71. 67.
    Stockigt, J. and M. H. Zenk. 1974. Enzymatic synthesis of chlorogenic acid from caffeoyl coenzyme A and quinic acid. FEBS Lett.42:131–34.PubMedCrossRefGoogle Scholar
  72. 68.
    Stockigt, J. and M. H. Zenk. 1975. Chemical syn thesis and properties of hydroxycinnamoyl coenzyme A derivatives. Z. Naturforsch.30c: 352–58.Google Scholar
  73. 69.
    Toms, A. and J. M. Wood. 1970. The degradation of trans-ferulic acid byPseudomonas acidovorans. Biochemistry9: 337–43.PubMedCrossRefGoogle Scholar
  74. 70.
    Ulbrich, B., J. Stockigt and M. H. Zenk. 1976. Induction by light of hydroxycinnamoyl-CoA quinate transferase activity in buckwheat hypocotyls. Naturwissenschaften63: 484.PubMedCrossRefGoogle Scholar
  75. 71.
    Ulbrich, B. and M. H. Zenk. 1977. to be published.Google Scholar
  76. 72.
    Ulbrich, B. and N. Amrhein. 1977. Induction by light of hydroxycinnamoyl-CoA: quinate hydroxycinnamoyl transferase in buckwheat (Fagopyrum esculentumMoench): Absence of feed-forward controle by trans-cinnamate. submitted for publication.Google Scholar
  77. 73.
    Vance, C. P., A. M. D. Numbudiri, C.-K. Wat and G. H. N. Towers. 1975. Isolation and properties of hydroxycinnamate CoA ligase fromPolyporus hispidus. Phytochem.14: 967–69.CrossRefGoogle Scholar
  78. 74.
    Walton, E. and V. S. Butt. 1971. The demonstration of einnamoyl-CoA synthetase activity in leaf extracts. Phytochem.1O: 295–04.CrossRefGoogle Scholar
  79. 75.
    Wengenmayer, H., J. Ebel and H. Grisebach. 1976. Enzymatic synthesis of lignin precursors. Purification and properties of cinnamoyl-CoA:NADPH reductase from cell suspension cultures of soybean (Glycinemax.). Eur. J. Biochem.65: 529–36.PubMedCrossRefGoogle Scholar
  80. 76.
    Zenk, M. H. 1960. Enzymatische Aktivierung von Auxi nen und ihre Konjugierung mit Glycin. Z. Naturforsch.15b: 436–41.Google Scholar
  81. 77.
    Zenk, M. H. 1965. Biosynthese von Vannillin inVanilla planifolia. Z. Pflanzenphysiol. 53:404–414.Google Scholar
  82. 78.
    Zenk M H. 1966. Biosynthesis of C6-C1-compounds.In: Billek, G. ed., Biosynthesis of aromatic compounds. Proceedings of the 2nd. Meeting of the Federation of European Biochemical Societies, Oxford, Pergamon Press, Vol. 31 p. 45–60, presented 1964.Google Scholar
  83. 79.
    Zenk, M. H. 1967. Pathways of salicyl alcohol and salicin formation inSalix purpureal. Phytochemistry6: 245–52.CrossRefGoogle Scholar
  84. 80.
    Zenk, M. H. 1971. Metabolism of prearomatic and aromatic compound in plants. In: Pharmacognosy and Phytochemistry, H. Wagner and L. Horhammer eds., Springer-Verlag, Berlin, Heidelberg, New York, p. 314–46.CrossRefGoogle Scholar
  85. 81.
    Zenk, M. H., B. Ulbrich, J. Busse and J. Stockigt. 1977. Procedure for enzymatic synthesis and isolation of hydroxycinnamoyl-CoA esters, in preparationGoogle Scholar

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© Plenum Press, New York 1979

Authors and Affiliations

  • M. H. Zenk
    • 1
  1. 1.Lehrstuhl für PflanzenphysiologieRuhr-Universität BochumBochumWest Germany

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