LIPID MAPS

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 (Ki = 4.0 uM) and HIV-1 reverse transcriptase (Ki = 1.2 µM).⁶

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References

1. 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" mouse. Eur. J. Biochem. 4(3), 340-344 (1968).

2. 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 mutant. Lipids 33(10), 993-1000 (1998).

3. Hirvisalo, E.L., and Renkonen, O. Composition of human serum sphingomyelins. J. Lipid Res. 11(1), 54-59 (1970).

4. 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 transcriptase. J. Biochem. 132(5), 819-828 (2002).

5. Sargent, J.R., Coupland, K., and Wilson, R. Nervonic acid and demyelinating disease. Med. Hypotheses 42(4), 237-242 (1994).

6. 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 use. Plant Biotechnol. J. 7(9), 925-938 (2009).