Selective increase in pinolenic acid (all-cis-5,9,12-18:3) in Korean pine nut oil by crystallization and its effect on LDL-receptor activity

Lipids. 2004 Apr;39(4):383-7. doi: 10.1007/s11745-004-1242-2.


The aims of this study were to obtain concentrated pinolenic acid (5,9,12-18:3) from dietary Korean pine (Pinus koraiensis) nut oil by urea complexation and to investigate its cholesterol-lowering effect on the LDL-receptor activity of human hepatoma HepG2 cells. Pine nut oil was hydrolyzed to provide a low-pinolenic acid-containing FA extract (LPAFAE), followed by crystallization with different ratios of urea in ethanol (EtOH) or methanol (MeOH) as a solvent to produce a high-pinolenic acid-containing FA extract (HPAFAE). The profiles of HPAFAE obtained by urea complexation showed different FA compositions compared with LPAFAE. The long-chain saturated FA palmitic acid (16:0) and stearic acid (18:0) were decreased with urea/FA ratios (UFR) of 1:1 (UFR1), 2:1 (UFR2), and 3:1 (UFR3). Linoleic acid (9,12-18:2) was increased 1.3 times with UFR2 in EtOH, and linolenic acid (9,12,15-18:3) was increased 1.5 times with UFR3 in MeOH after crystallization. The crystallization with UFR3 in EtOH provided the highest concentration of pinolenic acid, which was elevated by 3.2-fold from 14.1 to 45.1%, whereas that of linoleic acid (9,12-18:2) was not changed, and that of oleic acid (9-18:1) was decreased 7.2-fold. Treatment of HepG2 cells with HPAFE resulted in significantly higher internalization of 3,3'-dioctadecylindocarbocyanine-LDL (47.0 +/- 0.15) as compared with treatment with LPAFAE (25.6 +/- 0.36) (P< 0.05). Thus, we demonstrate a method for the concentration of pinolenic acid and suggest that this concentrate may have LDL-lowering properties by enhancing hepatic LDL uptake.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbocyanines / metabolism
  • Cell Line, Tumor
  • Crystallization
  • Dietary Fats, Unsaturated* / metabolism
  • Fluorescent Dyes / metabolism
  • Humans
  • Korea
  • Linolenic Acids* / chemistry
  • Linolenic Acids* / isolation & purification
  • Linolenic Acids* / metabolism
  • Nuts / chemistry*
  • Pinus / chemistry*
  • Plant Oils / chemistry*
  • Receptors, LDL / metabolism*
  • Urea / chemistry


  • Carbocyanines
  • Dietary Fats, Unsaturated
  • Fluorescent Dyes
  • Linolenic Acids
  • Plant Oils
  • Receptors, LDL
  • 5,9,12-octadecatrienoic acid
  • 3,3'-dioctadecylindocarbocyanine
  • Urea