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Title: Identification of 6-octadecynoic acid from a methanol extract of Marrubium vulgare L. as a peroxisome proliferator-activated receptor γ agonist

Highlights: •6-ODA, a rare fatty acid with a triple bond, was identified from Marrubium vulgare. •6-ODA was synthesized from petroselinic acid as a starting material. •6-ODA stimulated lipid accumulation in HSC-T6 and 3T3-L1 cells. •The first report of a fatty acid with a triple bond functioning as a PPARγ agonist. •This study sheds light on novel functions of a fatty acid with a triple bond. -- Abstract: 6-Octadecynoic acid (6-ODA), a fatty acid with a triple bond, was identified in the methanol extract of Marrubium vulgare L. as an agonist of peroxisome proliferator-activated receptor γ (PPARγ). Fibrogenesis caused by hepatic stellate cells is inhibited by PPARγ whose ligands are clinically used for the treatment of diabetes. Plant extracts of Marrubium vulgare L., were screened for activity to inhibit fibrosis in the hepatic stellate cell line HSC-T6 using Oil Red-O staining, which detects lipids that typically accumulate in quiescent hepatic stellate cells. A methanol extract with activity to stimulate accumulation of lipids was obtained. This extract was found to have PPARγ agonist activity using a luciferase reporter assay. After purification using several chromatographic methods, 6-ODA, a fatty acid with a triple bond, was identified as a candidate of PPARγ agonist. Synthesizedmore » 6-ODA and its derivative 9-octadecynoic acid (9-ODA), which both have a triple bond but in different positions, activated PPARγ in a luciferase reporter assay and increased lipid accumulation in 3T3-L1 adipocytes in a PPARγ-dependent manner. There is little information about the biological activity of fatty acids with a triple bond, and to our knowledge, this is the first report that 6-ODA and 9-ODA function as PPARγ agonists.« less
Authors:
; ;  [1] ; ; ; ;  [2] ;  [3] ;  [4] ; ;  [5] ; ;  [1] ; ;  [6] ;  [1]
  1. Graduate School of Biostudies, Kyoto University, Kyoto 606-8502 (Japan)
  2. Alliance for Research on North Africa (ARENA), University of Tsukuba, Ibaraki 305-8572 (Japan)
  3. (Japan)
  4. Arid Zone Research Institute (IRA), Médenine 4119 (Tunisia)
  5. Nippon Shinyaku CO., LTD., Kyoto 601-8550 (Japan)
  6. Graduate School of Agriculture, Kyoto University, Kyoto 606-8502 (Japan)
Publication Date:
OSTI Identifier:
22242139
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biochemical and Biophysical Research Communications; Journal Volume: 440; Journal Issue: 2; Other Information: Copyright (c) 2013 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved.; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES; BUILDUP; CARBOXYLIC ACIDS; CHROMATOGRAPHY; FIBROSIS; LIGANDS; LIPIDS; LIVER; LUCIFERASE; METHANOL; PROSTAGLANDINS; RECEPTORS