Very long chain fatty acid

A very-long-chain fatty acid (VLCFA) is a fatty acid with 22 or more carbons. Their biosynthesis occurs in the endoplasmic reticulum.[1] VLCFA's can represent up to a few percent of the total fatty acid content of a cell.[2]

Unlike most fatty acids, VLCFAs are too long to be metabolized in the mitochondria, {in the endoplasmic reticulum (ER) in plants} and must be metabolized in peroxisomes.

Certain peroxisomal disorders, such as adrenoleukodystrophy and Zellweger syndrome, can be associated with an accumulation of VLCFAs.[3][4] Enzymes that produce VLCFAs are the targets of herbicides including pyroxasulfone.[5][6]

Major VLCFAs

Some of the more common saturated VLCFAs: lignoceric acid (C24), cerotic acid (C26), montanic acid (C28), melissic acid (C30), lacceroic acid (C32), ghedoic acid (C34), and the odd-chain fatty acid ceroplastic acid (C35). Several monounsaturated VLCFAs are also known: nervonic acid (Δ15-24:1), ximenic acid (Δ17-26:1), and llumequeic acid (Δ21-30:1).[7]

See also

References
  1. Jakobsson, Andreas; Westerberg, Rolf; Jacobsson, Anders "Fatty acid elongases in mammals: their regulation and roles in metabolism" Progress in Lipid Research 2006, volume 45, pp. 237-249. doi:10.1016/j.plipres.2006.01.004
  2. "Very-long-chain fatty acids from the animal and plant kingdoms" Rezanka, Tomas Progress in Lipid Research 1989, volume 28, pp. 147-87. doi:10.1016/0163-7827(89)90011-8
  3. Kemp, Stephan and Watkins, Paul. "Very long-chain fatty acids". X-ald Database. Retrieved 5 January 2013.
  4. "Very long-chain acyl-CoA dehydrogenase deficiency". Genetics Home Reference, National Institutes of Health. Retrieved 5 January 2013.
  5. Nakatani, Masao; Yamaji, Yoshihiro; Honda, Hisashi; Uchida, Yukio (2016). "Development of the novel pre-emergence herbicide pyroxasulfone". Journal of Pesticide Science. 41 (3): 107–112. doi:10.1584/jpestics.J16-05. PMC 6140635. PMID 30363083.
  6. Trenkamp, S.; Martin, W.; Tietjen, K. (10 August 2004). "Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides". Proceedings of the National Academy of Sciences. 101 (32): 11903–11908. Bibcode:2004PNAS..10111903T. doi:10.1073/pnas.0404600101. PMC 511072. PMID 15277688.
  7. Řezanka, Tomáš; Sigler, Karel (2009). "Odd-Numbered Very-Long-Chain Fatty Acids from the Microbial, Animal and Plant Kingdoms". Progress in Lipid Research. 48 (3–4): 206–238. doi:10.1016/j.plipres.2009.03.003. PMID 19336244.

Bibliography


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