Uptake and incorporation of pinolenic acid reduces n-6 polyunsaturated fatty acid and downstream prostaglandin formation in murine macrophage

Lu Te Chuang, Po Jung Tsai, Chia Long Lee, Yung Sheng Huang

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Many reports have shown the beneficial effects of consumption of pine seeds and pine seed oil. However, few studies have examined the biological effect of pinolenic acid (PNA; δ5,9,12-18:3), the main fatty acid in pine seed oil. In this study, using murine macrophage RAW264.7 cells as a model, we examined the effect of PNA on polyunsaturated fatty acid (PUFA) metabolism, prostaglandin (PG) biosynthesis and cyclooxygenase-2 (COX-2) expression. Results showed that PNA was readily taken up, incorporated and elongated to form eicosatrienoic acid (ETrA, δ7,11,14-20:3) in macrophage cells. A small portion of this elongated metabolite was further elongated to form δ9,13,16-22:3. The degree of incorporation of PNA and its metabolites into cellular phospholipids varied with the length of incubation time and the concentration of PNA in the medium. Incubation of PNA also modified the fatty acid profile of phospholipids: the levels of 18- and 20-carbon PUFA were significantly decreased, whereas those of 22-carbon fatty acids increased. This finding suggests that PNA enhances the elongation of 20-carbon fatty acids to 22-carbon fatty acids. The syntheses of PGE1 from dihomo-γ-linolenic acid (DGLA, δ8,11,14-20:4) and PGE2 from arachidonic acid (ARA, δ5,8,11,14-20:4) were also suppressed by the presence of PNA and its metabolite. As the expression of COX-2 was not suppressed, the inhibitory effect of PNA on PG activity was attributed in part to substrate competition between the PNA metabolite (i.e., δ7,11,14-20:3) and DGLA (or ARA).

Original languageEnglish
Pages (from-to)217-224
Number of pages8
JournalLipids
Volume44
Issue number3
DOIs
Publication statusPublished - 2009 Mar 1

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Macrophages
Unsaturated Fatty Acids
Prostaglandins
Metabolites
Fatty Acids
Carbon
Oilseeds
Seeds
Cyclooxygenase 2
Phospholipids
Oils
alpha-Linolenic Acid
Alprostadil
Biosynthesis
Prostaglandin-Endoperoxide Synthases
Dinoprostone
Arachidonic Acid
Metabolism
Seed
Elongation

Keywords

  • Cyclooxygenase 2
  • Gamma-linolenic acid
  • Non-methylene interrupted fatty acids
  • Sciadonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Cell Biology

Cite this

Uptake and incorporation of pinolenic acid reduces n-6 polyunsaturated fatty acid and downstream prostaglandin formation in murine macrophage. / Chuang, Lu Te; Tsai, Po Jung; Lee, Chia Long; Huang, Yung Sheng.

In: Lipids, Vol. 44, No. 3, 01.03.2009, p. 217-224.

Research output: Contribution to journalArticle

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