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Cyclopropane fatty acid

Cyclopropane fatty acids (CPA) are a subgroup of fatty acids that contain a cyclopropane group. Although they are usually rare, the seed oil from lychee contains nearly 40% CPAs in the form of triglycerides.

Biosynthesis

CPAs are derived from unsaturated fatty acids by cyclopropanation. The methylene donor is a methyl group on S-adenosylmethionine (SAM). The conversion is catalyzed by cyclopropane-fatty-acyl-phospholipid synthase. 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.

Cyclopropene fatty acids

Cyclopropene fatty acids are even rarer molecules. The best-known examples are malvalic acid and sterculic acid. A triglyceride made of 3 sterculic acid molecules esterified with glycerol is present in Sterculia foetida seed oil (in amounts greater than 60%) and at low levels in the seed oil of other species of Malvaceae (~12%), cottonseed oil (~1%). 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.

At least one review indicates that these compounds are carcinogenic.

Notes

References

References

  1. "Natural alicyclic fatty acids, cyclopropane, cyclopropene, cyclopentene - structure, composition, analysis, biosynthesis".
  2. Gaydou, E. M.; Ralaimanarivo, A.; Bianchini, J. P. "Cyclopropanoic Fatty-Acids of Litchi (Litchi-Chinensis) Seed Oil - a Reinvestigation" J. Agr. Food Chem. 1993, vol. 41, pp. 886-890. {{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. Ludger A. Wessjohann and Wolfgang Brandt, Thies Thiemann "Biosynthesis and Metabolism of Cyclopropane Rings in Natural Compounds" Chem. Rev., 2003, volume 103, pp 1625–1648. {{doi. 10.1021/cr0100188
  5. (April 1978). "Cyclopropene fatty acids of selected seed oils from bombacaceae, malvaceae, and sterculiaceae". Lipids.
  6. (December 2011). "Characterization and analysis of the cotton cyclopropane fatty acid synthase family and their contribution to cyclopropane fatty acid synthesis". BMC Plant Biology.
  7. Abraham, Samuel. (1975). "International encyclopedia of pharmacology and therapeutics: Pharmacology of lipid transport and atherosclerotic processes, Volume 1". Pergamon Press.
  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.
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