Nervonic acid (24:1, n−9) is a

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...

. It is a monounsaturated analog of

lignoceric acid Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoc ...

(24:0). It is also known as selacholeic acid and ''cis''-15-tetracosenoic acid. Its name derives from the

Latin Latin (, or , ) is a classical language belonging to the Italic branch of the Indo-European languages. Latin was originally a dialect spoken in the lower Tiber area (then known as Latium) around present-day Rome, but through the power of the ...

word '' nervus'', meaning nerve or sinew. It exists in nature as an elongation product of

oleic acid Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega ...

(18:1 Δ9), its immediate precursor being

erucic acid Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula CH3(CH2)7CH=CH(CH2)11COOH. It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in h ...

. Nervonic acid is particularly abundant in the white matter of animal brains and in peripheral nervous tissue where nervonyl sphingolipids are enriched in the myelin sheath of nerve fibers. In the same way, recent studies have concluded that nervonic acid is implicated as an intermediate in the biosynthesis of nerve cell

myelin Myelin is a lipid-rich material that surrounds nerve cell axons (the nervous system's "wires") to insulate them and increase the rate at which electrical impulses (called action potentials) are passed along the axon. The myelinated axon can be ...

. This acid is an important member of the group of the cerebrosides, which are fatty acids of the glycosphingolipids group, important components of the muscles and the central nervous system and peripheral. Indeed, it is one of the major fatty acids in brain sphingolipids, normally accounting for approximately 40% of the total fatty acids in sphingolipids.

Structure

As it is defined as a

monounsaturated In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple est ...

fatty acid, it has one double bond in the fatty acid chain and all the remaining

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

atoms are single-bonded. It is classified in the sub-group of very long chain fatty acids (VLCFA), which includes molecules containing more than 20 carbon atoms. It has specifically 24-carbon backbone and the sole C=C double bond originating from the methyl end is in n-9 or omega-9 (ω-9).

Functions

Nervonic acid is an essential nutrient for the growth and maintenance of the

brain A brain is an organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It is located in the head, usually close to the sensory organs for senses such as vision. It is the most complex organ in a v ...

. This acid has been found in breast-milk: it is said it can speed the development in infants. It is the reason why it is recommended to pregnant and nursing women. This acid is a regulator of the Ca²⁺

ion channel Ion channels are pore-forming membrane proteins that allow ions to pass through the channel pore. Their functions include establishing a resting membrane potential, shaping action potentials and other electrical signals by gating the flow of io ...

in the cell membrane of nerve tissues, so nervonic acid plays an important role in the control of the levels of calcium of the cytosol. Nervonic acid can regulate the function of brain cell membranes and have a neuroprotective effect which is important to high-level training adults or athletes: it is an energy supplement. Moreover, due to its function as an intermediate in myelin biosynthesis, dietary therapy with nervonic acid-containing fats has been studied: nervonic acid appears to be beneficial for the treatment of genetic disorders of the lipid metabolism, such as

Zellweger syndrome Zellweger syndrome is a rare congenital disorder characterized by the reduction or absence of functional peroxisomes in the cells of an individual. It is one of a family of disorders called Zellweger spectrum disorders which are leukodystrophie ...

or adrenoleukodistrophy. Nervonic acid beta-oxidation takes place in

peroxisome A peroxisome () is a membrane-bound organelle, a type of microbody, found in the cytoplasm of virtually all eukaryotic cells. Peroxisomes are oxidative organelles. Frequently, molecular oxygen serves as a co-substrate, from which hydrogen pero ...

s, and this oxidation is impaired in X-ALD patients. Due to different mutations, people having these disorders have ineffective peroxisomes. It causes an important accumulation of very long chain fatty acids, that can be treated with oils enriched with 24:1 (Lorenzo's oil, Lunaria's oil). It is also used as a biomarker to predict who will suffer some psychoses. For instance, there is evidence of abnormal levels of fatty acids in individuals with schizophrenia. In particular, decreased levels of 24:1 are related with prodromal psychosis symptoms so it can be beneficial in the prevention and treatment of this kind of disorders. Nervonic acid can be an indicator of future neurodevelopmental disorders in male babies whose mother has preeclampsia. Recent studies show that cord nervonic acid levels were lower in women with preeclampsia delivering male babies as compared to normotensive control group. But this does not happen with girl babies. These results suggest that male babies born to mothers with preeclampsia may be at an increased risk of developing neurodevelopmental disorders as compared to female babies. This acid is present in the composition of aged eye lens, but it does not appear in normal eye lens. This data shows that we can use the presence of nervonic acid (together with heneicosylic acid and

docosahexaenoic acid Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, and retina. In physiological literature, it is given the name 22:6(n-3). It can be synthesized from alpha-lino ...

) as biomarkers of aging lens, which is the most vulnerable stage for cataract development.

Sources

Nervonic acid occurs in

seed oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fats ...

of plants, where significant amounts are contained. Indeed, more than 10% of the lipids contain nervonic acid, usually in the form of

triglyceride A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other vertebrates, as w ...

s. The seed oils of ''

Lunaria ''Lunaria'', common names honesty, dollar plant, money-in-both-pockets, money plant, moneywort, moonwort, and silver dollar; is a genus of flowering plants in the family Brassicaceae. It is native to central and southern Europe and North Americ ...

'' species ('' Lunaria biennis'' or ''

Lunaria annua ''Lunaria annua'', called honesty or annual honesty in English, is a species of flowering plant in the cabbage and mustard family Brassicaceae. It is native plant, native to the Balkans and south west Asia, and cultivated throughout the temperate ...

'', for example) are a quite important source of this long chain fatty acid, since they contain over 20% of it in the triglyceride lipid. Nervonic acid is also found in '' Cardamine gracea'', '' Heliophila longifola'', and '' Malania oleifera''. In all these species, 24:1 usually is esterified at the sn-1 and sn-3 positions on the glycerol backbone. Other sources can be the

mold A mold () or mould () is one of the structures certain fungus, fungi can form. The dust-like, colored appearance of molds is due to the formation of Spore#Fungi, spores containing Secondary metabolite#Fungal secondary metabolites, fungal seco ...

s ''

Neocallimastix frontalis ''Neocallimastix'' is a genus of obligately anaerobic rumen fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mu ...

'', the bacterium '' Pseudomonas atlantica'', the yeast ''

Saccharomyces cerevisiae ''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have been o ...

'', and the marine diatom '' Nitzschia cylindrus''.

References

Additional references

* Appelqvist (1976) Lipids in Cruciferae. In: Vaughan JG, Macleod AJ (Eds), ''The biology and the Chemistry of Cruciferae''. Academic Press, London, UK, pp. 221–277. {{Fatty acids Fatty acids Alkenoic acids