Nervonic acid (Selacholeic acid)

Nervonic acid (24:1n-9) is a very long chain fatty acid produced by elongation of oleic acid (18:1n-9) and derived from erucic acid (22:1n-9) .¹ It is enriched in nervous tissue and is particularly abundant in sphingolipids, such as sphingomyelin in the myelin sheath of nerve fibers.² Nervonic acid is poorly produced in demyelinating disorders, including multiple sclerosis and adrenoleukodystrophy, suggesting that dietary supplementation may be beneficial.³ In addition, it is deficient in mice which are homozygous for the quaking mutation, a model of Parkinson’s disease.^4,5 Nervonic acid also binds and inhibits DNA polymerase β (K_i = 4.0 uM) and HIV-1 reverse transcriptase (K_i = 1.2 ?M).⁶

1.Taylor, D.C., Francis, T., Guo, Y., et al.Molecular cloning and characterization of a KCS gene from Cardamine graeca and its heterologous expression in Brassica oilseeds to engineer high nervonic acid oils for potential medical and industrial usePlant Biotechnol. J.7(9)925-938(2009) 2.Hirvisalo, E.L., and Renkonen, O.Composition of human serum sphingomyelinsJ. Lipid Res.11(1)54-59(1970) 3.Sargent, J.R., Coupland, K., and Wilson, R.Nervonic acid and demyelinating diseaseMed. Hypotheses42(4)237-242(1994) 4.Baumann, N.A., Jacque, C.M., Pollet, S.A., et al.Fatty acid and lipid composition of the brain of a myelin deficient mutant, the "quaking" mouseEur. J. Biochem.4(3)340-344(1968) 5.Cook, C., Barnett, J., Coupland, K., et al.Effects of feeding Lunaria oil rich in nervonic and erucic acids on the fatty acid compositions of sphingomyelins from erythrocytes, liver, and brain of the quaking mouse mutantLipids33(10)993-1000(1998) 6.Kasai, N., Mizushina, Y., Sugawara, F., et al.Three-dimensional structural model analysis of the binding site of an inhibitor, nervonic acid, of both DNA polymerase β and HIV-1 reverse transcriptaseJ. Biochem.132(5)819-828(2002)