The depressive effects of 5,8,11-eicosatrienoic Acid (20:3n-9) on osteoblasts

Lipids. 2009 Feb;44(2):97-102. doi: 10.1007/s11745-008-3252-8. Epub 2008 Oct 22.


In cases of essential fatty acid deficiency, 5,8,11-eicosatrienoic acid (Mead acid, 20:3n-9) is synthesized from oleic acid as a 20-carbon analog of arachidonic acid. It was reported that 20:3n-9 levels were markedly higher in human fetal cartilage than in the muscle, liver and spleen. We, therefore, hypothesized that 20:3n-9 decreased osteoblastic activity. Goldfish scales were incubated either with 20:3n-9 or with oleic acid at 15 degrees C for 6 and 18 h. Both osteoblastic and osteoclastic activities in the scale were assessed by measuring alkaline phosphatase (ALP) and tartrate-resistant acid phosphatase, respectively. MC3T3-E1 cells (an osteoblast cell line derived from the mouse) were incubated with 20:3n-9 or oleic acid at 37 degrees C for 6 and 18 h. ALP activity in cell lysate was measured. In the case of experiments with scales, 20:3n-9 (1-100 muM) significantly suppressed osteoblastic activity after 6 and 18 h of incubation, whereas oleic acid did not change this activity. Osteoclastic activity was not affected either by 20:3n-9 or by oleic acid. In the case with the cell line, osteoblastic activity was again significantly decreased with 20:3n-9 (10-30 muM) after 6-h incubation but not after 18 h incubation. The presence of 20:3n-9 in fetal cartilage may be important for the prevention of calcification in the cartilage. 20:3n-9 could be applied to some clinical situations where bone formation should be inhibited.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 8,11,14-Eicosatrienoic Acid / analogs & derivatives*
  • 8,11,14-Eicosatrienoic Acid / pharmacology
  • Acid Phosphatase / metabolism
  • Alkaline Phosphatase / metabolism
  • Animals
  • Cell Line
  • Depression, Chemical
  • Female
  • Goldfish
  • Isoenzymes / metabolism
  • Mice
  • Oleic Acid / pharmacology
  • Osteoblasts / drug effects*
  • Osteoblasts / physiology
  • Osteoclasts / drug effects
  • Osteoclasts / physiology
  • Tartrate-Resistant Acid Phosphatase


  • Isoenzymes
  • Oleic Acid
  • Alkaline Phosphatase
  • Acid Phosphatase
  • Tartrate-Resistant Acid Phosphatase
  • 8,11,14-Eicosatrienoic Acid
  • mead acid