Divinylether fatty acids

Chemical structure of colneleic acid

Divinylether fatty acids contain a fatty acid chemically combined with a doubly unsaturated carbon chain linked by an oxygen atom (ether). Fatty acid hydroperoxides generated by plant lipoxygenases from linoleic and linolenic acids are known to serve as substrates for a divinyl ether synthase which produces divinyl ether fatty acids. Up to date divinyl ethers were detected only within the plant kingdom.

The discovery of that class of compounds dates back to 1972, when the structures of two ether C18 fatty acids generated by homogenates of the potato tuber were described.[1] These compounds, named colneleic acid (from linoleic acid) and colnelenicacid (from linolenic acid), could be also produced in potato leaves and tomato roots by rearrangement of 9-hydroperoxides.

Isomers of colneleic and colnelenic acids were isolated from homogenates of leaves of Clematis vitalba (Ranunculaceae).[2]

Similarly, 13-lipoxygenase-generated hydroperoxides serve as precursor of other divinyl ether fatty acids which are produced in bulbs of garlic [3] or Ranunculus leaves.[4] These compounds were named etheroleic and etherolenic acids. Etheroleic acid has systematic name 12-[1′E-hexenyloxy]-9Z,11Z-dodecadienoic acid. Etherolenic acid has systematic name (9Z,11E,1'E,3'Z)-12-(1',3'-Hexadienyloxy)-9,11-dodecadienoic acid.

The physiological significance of divinyl ethers is still not fully studied. As infection of potato leaves leads to increased levels of divinyl ether synthase, it was suggested that this pathway could be of importance in the defense of plants against attacking pathogens.[5] Similar structures have been discovered in the brown alga Laminaria sinclairii, with 18 or 20 carbons and 4, 5 or 6 double bonds,[6] and in the red alga Polyneura latissima, with 20 carbons and 5 double bonds.[7]

References

  1. ↑ Galliard, T.; Phillips, D. R. (September 1972). "The enzymic conversion of linoleic acid into 9-(nona-1′,3′-dienoxy)non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers". Biochemistry Journal. 129 (3): 743–753. PMC 1174176Freely accessible. PMID 4658996.
  2. ↑ Hamberg, M. (June 2004). "Isolation and structures of two divinyl ether fatty acids from Clematis vitalba". Lipids. 39 (6): 565–569. doi:10.1007/s11745-004-1264-9. PMID 15554156.
  3. ↑ Grechkin, Alexander N.; Fazliev, F. N.; Mukhtarova, L. S. (October 1995). "The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins". FEBS Letters. 371 (2): 159–162. doi:10.1016/0014-5793(95)00895-G.
  4. ↑ Hamberg, M. (November 1998). "A pathway for biosynthesis of divinyl ether fatty acids in green leaves". Lipids. 33 (11): 1061–1071. doi:10.1007/s11745-998-0306-7. PMID 9870900.
  5. ↑ Göbel, C; Feussner, I.; Hamberg M, M.; Rosahl, S. (5 September 2002). "Oxylipin profiling in pathogen-infected potato leaves". Biochim Biophys Acta. 1584 (1): 55–64. doi:10.1016/s1388-1981(02)00268-8. PMID 12213493.
  6. ↑ Proteau, P. J.; Gerwick, William H. (1993). "Divinyl ethers and hydroxy fatty acids from three species of Laminaria (brown algae)". Lipids. 28: 783–787. doi:10.1007/bf02536231.
  7. ↑ Jiang, Z. D.; Gerwick, William H. (1 March 1997). "Novel oxylipins from the temperate red alga Polyneura latissima". Lipids. 32 (3): 231–235. doi:10.1007/s11745-997-0029-9.
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