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Lipids

, Volume 26, Issue 7, pp 512–516 | Cite as

Sesamin is a potent and specific inhibitor of Δ5 desaturase in polyunsaturated fatty acid biosynthesis

  • Sakayu Shimizu
  • Kengo Akimoto
  • Yoshifumi Shinmen
  • Hiroshi Kawashima
  • Michihiro Sugano
  • Hideaki Yamada
Article

Abstract

Incubation with sesame oil increases the mycelial dihomo-γ-linolenic acid content of an arachidonic acid-producing fungus,Mortierella alpina, but decreases its arachidonic acid content [Shimizu, S., K. Akimoto, H. Kawashima, Y. Shinmen and H. Yamada (1989)J. Am. Oil Chem. Soc. 66, 237–241]. The factor causing these effects was isolated and identified to be (+)-sesamin. The results obtained in experiments with both a cell-free extract of the fungus and with rat liver microsomes demonstrated that (+)-sesamin specifically inhibits Δ5 desaturase at low concentrations, but does not inhibit Δ6, Δ9 and Δ12 desaturases. Kinetic analysis showed that (+)-sesamin is a noncompetitive inhibitor (Ki for rat liver Δ5 desaturase, 155 μM). (+)-Sesamolin, (+)-sesaminol and (+)-episesamin, also inhibited only Δ5 desaturases of the fungus and liver. These results demonstrate that (+)-sesamin and related lignan compounds present in sesame seeds or its oil are specific inhibitors of Δ5 desaturase in polyunsaturated fatty acid biosynthesis in both microorganisms and animals.

Keywords

Sesamin Sesamol Sesamolin Arachidonic Acid Content Episesamin 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Abbreviations

AA or 20∶4

arachidonic acid

DGLA or 20∶3

dihomo-γ-linolenic acid

HPLC

high-performance liquid chromatography

MS

mass spectrometry

NMR

nuclear magnetic resonance

PUFA

polyunsaturated fatty acids

TLC

thin-layer chromatography

18∶0

stearic acid

18∶1

oleic acid

18∶2

linoleic acid

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Copyright information

© American Oil Chemists’ Society 1991

Authors and Affiliations

  • Sakayu Shimizu
    • 1
  • Kengo Akimoto
    • 1
  • Yoshifumi Shinmen
    • 1
  • Hiroshi Kawashima
    • 1
  • Michihiro Sugano
    • 2
  • Hideaki Yamada
    • 1
  1. 1.Department of Agricultural ChemistryKyoto UniversityKyoto
  2. 2.Department of Food Science and TechnologyKyushu UniversityFukuokaJapan

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