Lipoxygenase inhibitory activity of 6-pentadecanylsalicylic acid without prooxidant effect

Isao Kubo, Tae Joung Ha, Kuniyoshi Shimizu

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

6-Pentadecanylsalicylic acid, referred to as anacardic acid (C 15:0), was found to inhibit the linoleic acid peroxidation competitively catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, Type 1) with an IC50 of 14.3 μM (4.88 μg/mL). This inhibition is a reversible reaction without pro-oxidant effects. The inhibition kinetics analyzed by Dixon plots indicates that anacardic acid (C15:0) is a competitive inhibitor and the inhibition constant, KI, was established as 6.4 μM. The hydrophilic head (salicylic acid) portion first chelates the iron in the active site and then the hydrophobic tail portion begins reversibly interacting with the C-terminal domain where the iron is located. The inhibition of anacardic acid (C15:0) can be explained by a combination of iron ion-chelation and hydrophobic interaction abilities because of its specific structural feature.

Original languageEnglish
Pages (from-to)85-90
Number of pages6
JournalNatural product communications
Volume5
Issue number1
Publication statusPublished - Jul 5 2010

Fingerprint

Lipoxygenase
lipoxygenase
Acids
acids
iron
Iron
Iron Chelating Agents
Salicylic Acid
Linoleic Acid
Hydrophobic and Hydrophilic Interactions
Inhibitory Concentration 50
chelation
hydrophobic bonding
Reactive Oxygen Species
Catalytic Domain
peroxidation
chelates
Head
salicylic acid
active sites

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

Cite this

Lipoxygenase inhibitory activity of 6-pentadecanylsalicylic acid without prooxidant effect. / Kubo, Isao; Ha, Tae Joung; Shimizu, Kuniyoshi.

In: Natural product communications, Vol. 5, No. 1, 05.07.2010, p. 85-90.

Research output: Contribution to journalArticle

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