The botanical magazine = Shokubutsu-gaku-zasshi

, Volume 97, Issue 3, pp 355–367 | Cite as

Biosynthesis of gallic and ellagic acids with14C-labeled compounds inAcer andRhus leaves

  • Nariyuki Ishikura
  • Shunzo Hayashida
  • Kiyoshi Tazaki


The biosynthetic pathway for gallic and ellagic acids in young, mature and autumn leaves ofAcer buergerianum andRhus succedanea was examined by tracer experiments, and also by isotope competition, withd-shikimic acid-14C,l-phenylalanine-U-14C,l-phenyllactic acid-U-14C, gallic acid-G-14C and their unlabeled compounds. In young leaves of both plants, the incorporation rate of labeled shikimic acid into gallic acid was significantly higher than that of labeled phenylalanine, whereas in the mature and autumn leaves the latter was a good precursor rather than the former for the gallic acid biosynthesis. Therefore, two pathways for gallic acid formation, through β-oxidation of phenylpropanoid and through dehydrogenation of shikimic acid, could be operating inAcer andRhus leaves, and the preferential pathway is altered by leaf age. In both plants, the incorporation rate of labeled phenyllactic acid during a 24 hr metabolic period was almost the same as that of labeled phenylalanine. The incorporation ofd-skikimic acid-G-14C,l-phenylalanine-U-14C andl-phenyllactic acid-U-14C into ellagic acid was very similar to the case of the radioactive gallic acid formation. Furthermore, regardless of the presence of unlabeled shikimic acid and/or phenylalanine, incorporation of the radioactivity of labeled gallic acid into ellagic acid occurred at a very high rate, suggesting the reciprocal radical reaction of gallic acid for the ellagic acid formation. The incorporation of labeled compounds into ellagitanins was also examined and their biosynthesis discussed further.

Key words

Acer buergerianum Biosynthesis Ellagic acid Gallic acid 14C-labeled compounds Rhus succedanea 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Amagasa, T. andS. Yoshida. 1979. Transfer of label from aspartate to malate by the cell-free extract ofSedum mexicanum leaves. Plant Cell Physiol.20: 1191–1197.Google Scholar
  2. Browning, B.L. 1966. Phenolic Substances in Methods of Wood Chemistry I: 223–251. Interscience, New York.Google Scholar
  3. Cartwright, R.A. and E.A.H. Roberts. 1955. Theogallin as a galloyl ester of quinic acid. Chem. and Ind. 230–231.Google Scholar
  4. Conn, E.E. and T. Swain. 1961. Biosynthesis of gallic acid in higher plants. Chem. and Ind. 592–593.Google Scholar
  5. Gaines, C.G., G.S. Byng, R.J. Whitaker andR.A. Jensen 1982. L-Tyrosine regulation and biosynthesisvia arogenate dehydrogenase in suspension-cultured cells ofNicotiana sylvestris Speg. et Comes. Planta156: 233–240.CrossRefGoogle Scholar
  6. Haslam, E. 1974. The Shikimate Pathway. London Butterworths London.Google Scholar
  7. Haslam, E., R.D. Haworth and P.F. Knowles. 1961. Gallotannins. Part IV. The biosynthesis of gallic acid. J. Chem. Soc. 1854–1859.Google Scholar
  8. Higuchi, T. andS.A. Brown. 1963. Studies of lignin biosynthesis using isotopic carbon XIII. The phenylpropanoid system in lignification. Can. J. Biochem. Physiol.41: 621–628.PubMedGoogle Scholar
  9. Ishikura, N. 1971. Flavonol glycosides and anthocyanin from the capsule ofEuscaphis japonica. Bot. Mag. Tokyo84: 1–7.Google Scholar
  10. — 1972. Anthocyanins and other phenolics in autumn leaves. Phytochemistry11: 2555–2558.CrossRefGoogle Scholar
  11. — 1975. Incorporation rate of shikimic acid-14C and phenylalanine-14C into gallic acid inRhus andAcer leaves. Experientia31: 1407–1408CrossRefGoogle Scholar
  12. — 1976. Seasonal changes in contents of phenolic compounds and sugar inRhus, Euonymus andAcer leaves with special references to anthocyanin formation in autumn. Bot. Mag. Tokyo89: 251–257.CrossRefGoogle Scholar
  13. Kato, M., M. Shiroya, S. Yoshida andM. Hasegawa. 1968. Biosynthesis of gallic acid by a homogenate of the leaves ofPelargonium inquinans. Bot. Mag. Tokyo81: 506–507.Google Scholar
  14. Saijo, R. 1983. Pathway of gallic acid biosynthesis and its, esterification with catechins in young tea shoots. Agric. Biol. Chem.47: 455–460.Google Scholar
  15. Schmidt, O. Th. andW. Mayer. 1956. Naturliche Gerbstoffe. Angew. Chem.68: 103–115.Google Scholar
  16. Taneyama, M. and S. Yoshida. 1982. Bisynthesis of gallic acid in the protoplast, ofSaxifraga stolonifera leaves. Proc. 47th Annu. Meet. Bot. Soc. Japan p. 132 (in Japanese).Google Scholar
  17. Tateoka, T.N. 1968. Formation of protocatechuic acid from 5-dehydroshikimic acid in the extract of mung bean seedling. Bot. Mag. Tokyo.81: 103–104.Google Scholar
  18. Wat, C.-K. andG.H.N. Towers. 1979. Metabolism of the aromatic amino acids by fungi.In: T. Swainet al., ed., Biochemistry of Plant Phenolics, Recent Advances in Phytochemistry12: 371–432. Plenum Press, New York.Google Scholar
  19. Wenkert, E. 1959. Biosynthesis of hydrolyzable tannins. Chem. and Ind. 906–907.Google Scholar
  20. Zenk, M.H. 1964. Zur Frage der Biosynthese von Gallussäure. Z. Naturforsch.19b: 83–84.Google Scholar

Copyright information

© The Botanical Society of Japan 1984

Authors and Affiliations

  • Nariyuki Ishikura
    • 1
  • Shunzo Hayashida
    • 1
  • Kiyoshi Tazaki
    • 1
  1. 1.Department of Biology, Faculty of ScienceKumamoto UniversityKumamoto

Personalised recommendations