Description and references

Polyunsaturated fatty acid produced in the body as the Δ⁶-desaturase metabolite of linoleic acid, q.v. Converted to dihomo-γ-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE₁. Present to varying extents in the fatty acid fraction of evening primrose oil (7-10%), in borage oil (18-26%), in black currant oil (15-20%) and in oils from different fungal sources (6-24%). Isoln from evening primrose oil, q.v.: A. Heiduschka, K. Luft, Arch. Pharm. 257, 33 (1919). Proposed structure: Eibner et al., Chem. Umschau. 34, 312 (1927). Confirmation of structure: J. P. Riley, J. Chem. Soc. 1949, 2728. Discussion of occurrence, esp. in fungi: R. Shaw, Biochim. Biophys. Acta 98, 230 (1965). Synthesis: J. M. Osbond et al., J. Chem. Soc. 1961, 2779; J. M. Osbond, ibid. 5270. Metabolism studies: J. F. Mead, D. R. Howton, J. Biol. Chem. 229, 575 (1957); K. J. Stone et al., Lipids 14, 174 (1979). Effect of source on essential fatty acid and prostanoid metabolite formation: D. K. Jenkins et al., Med. Sci. Res. 16, 525 (1988).

Derivative