Inhibition of phenylalanine ammonia-lyase by cinnamic acid derivatives and related compounds

Toshitsugu Sato, Fumiyuki Kiuchi, Ushio Sankawa

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

Thirty-five derivatives of cinnamic acid and related compounds were tested for inhibition against phenylalanine ammonia-lyase (PAL) derived from sweet potato, pea and yeast. Caffeic and gallic acids showed inhibition against PAL originating from higher plants, but not against yeast PAL. In contrast, yeast PAL was specifically inhibited by p-hydroxycinnamic and p-hydroxybenzoic acids. The results suggest that caffeic and gallic acids may act as regulatory substances in phenylpropanoid metabolism in higher plants. Inhibition experiments with synthetic cinnamic acid derivatives have revealed that the presence of a hydrophobic aromatic ring, α,β-double bond and carboxyl group is essential for inhibitory activity. 2-Naphthoic acid which fulfills these structural requirements showed a strong inhibition. The size and shape of the active site is discussed from structure-activity relationships of cinnamic acid derivatives. o-Chlorocinnamic acid, one of the strongest inhibitors found in this study showed an inhibitory effect on the growth of the roots of rice seedlings.

Original languageEnglish
Pages (from-to)845-850
Number of pages6
JournalPhytochemistry
Volume21
Issue number4
DOIs
Publication statusPublished - 1982
Externally publishedYes

Fingerprint

Phenylalanine Ammonia-Lyase
cinnamic acid
phenylalanine ammonia-lyase
Caffeic Acids
chemical derivatives
Yeast
Derivatives
Gallic Acid
Yeasts
caffeic acid
yeasts
gallic acid
Ipomoea batatas
Enzyme inhibition
Hydroxybenzoates
4-hydroxybenzoic acid
acids
Peas
phenylpropanoids
structure-activity relationships

Keywords

  • ammonia-lyase
  • cinnamic acid.
  • Enzyme
  • growth
  • inhibitor
  • PAL
  • phenylalanine
  • tyrosine

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Inhibition of phenylalanine ammonia-lyase by cinnamic acid derivatives and related compounds. / Sato, Toshitsugu; Kiuchi, Fumiyuki; Sankawa, Ushio.

In: Phytochemistry, Vol. 21, No. 4, 1982, p. 845-850.

Research output: Contribution to journalArticle

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