, Volume 44, Issue 2, pp 97–102 | Cite as

The Depressive Effects of 5,8,11-Eicosatrienoic Acid (20:3n-9) on Osteoblasts

  • Tomohito Hamazaki
  • Nobuo Suzuki
  • Retno Widyowati
  • Tatsuro Miyahara
  • Shigetoshi Kadota
  • Hiroshi Ochiai
  • Kei Hamazaki
Original Article


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 °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 °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 μM) 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 μM) 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.


Bone Cartilage Co-culture Fatty acids Goldfish scales Osteoclasts 



5,8,11-Eicosatrienoic acid (20:3n-9, Mead acid)


Arachidonic acid


Alkaline phosphatase


Tartrate-resistant acid phosphatase


Cystic fibrosis


Receptor activator of NF-κB


Receptor activator of NF-κB ligand


Leukotriene B4


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Copyright information

© AOCS 2008

Authors and Affiliations

  • Tomohito Hamazaki
    • 1
  • Nobuo Suzuki
    • 2
  • Retno Widyowati
    • 3
  • Tatsuro Miyahara
    • 4
  • Shigetoshi Kadota
    • 3
  • Hiroshi Ochiai
    • 4
  • Kei Hamazaki
    • 1
  1. 1.Department of Clinical Sciences, Institute of Natural MedicineUniversity of ToyamaToyamaJapan
  2. 2.Noto Marine Laboratory, Institute of Nature and Environmental TechnologyKanazawa UniversityIshikawaJapan
  3. 3.Department of Natural Products Chemistry, Institute of Natural MedicineUniversity of ToyamaToyamaJapan
  4. 4.Department of Human Science, Faculty of MedicineUniversity of ToyamaToyamaJapan

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