Cyclopropane fatty acid

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mycolic acids, a class of mono- and dicyclopropane fatty acids found in the cell wall of the bacterium Mycobacterium tuberculosis

Cyclopropane fatty acids (CPA) are a subgroup of

cyclopropane group.[1] Although they are usually rare, the seed oil from lychee contains nearly 40% CPAs in the form of triglycerides.[2]


Biosynthesis

CPAs are derived from unsaturated fatty acids by

S-adenosylmethionine (SAM). The conversion is catalyzed by cyclopropane-fatty-acyl-phospholipid synthase.[3] The mechanism is proposed to involve transfer of a CH3+ group from SAM to the alkene, followed by deprotonation of the newly attached methyl group and ring closure.[4]

Cyclopropene fatty acids

malvalic acid, a cyclopropene fatty acid

Cyclopropene fatty acids are even rarer than CPAs. The best-known examples are malvalic acid and sterculic acid. Sterculic acid as its triglyceride is present in sterculia oils and at low levels in the seed oil of species of Malvaceae[a] (~12%), cottonseed oil (~1%), and in the seeds of the tree Sterculia foetida (~65-78%). These acids are highly reactive but the cyclopropene ring is destroyed during refining and hydrogenation of the oils. They have attracted interest because they reduce levels of the enzyme stearoyl-CoA 9-desaturase (SCD), which catalyzes the biodesaturation of stearic acid to oleic acid.[7]

At least one review indicates that CPFA are carcinogenic, co-carcinogenic, and have medical and other effects on animals;[8] according to this review, "CPFA in food is dangerous to human health".

Notes

  1. ^ A number of species in several genera of the Malvaceae family are known as 'Kapok trees'. For example: Ceiba pentandra, Bombax ceiba and B. costatum are all widely and ambiguously called "the kapok".[5][6]

References

  1. ^ "Natural alicyclic fatty acids, cyclopropane, cyclopropene, cyclopentene - structure, composition, analysis, biosynthesis". Archived from the original on 2014-12-17. Retrieved 2015-02-02.
  2. doi:10.1021/jf00030a009
  3. ^ Grogan DW, Cronan JE Jr: Cyclopropane ring formation in membrane lipids of bacteria" Microbiol Mol Biol Rev 1997, vol. 61, pp. 429-441. http://mmbr.asm.org/content/61/4/429.full.pdf+html
  4. doi:10.1021/cr0100188
  5. S2CID 4017359
    .
  6. PMID 21612656
    .
  7. ISBN 9780080177625
    .
  8. ^ L. O. Hanus, P. Goldshlag, V. M. Dembitsky (2008). IDENTIFICATION OF CYCLOPROPYL FATTY ACIDS IN WALNUT (JUGLANS REGIA L.) OIL. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2008, 152(1):41–45.

Further reading

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