The biosynthesis of ‘unusual’ fatty acids with structures other than the common C16 and C18 fatty acids has evolved numerous times in the plant kingdom. A greater understanding of biochemical plasticity and oil functionality can be gained from the characterization of unusual fatty acid biosynthesis. Here, we report the identification of a novel pathway for hydroxy fatty acid biosynthesis uncovered during the serendipitous discovery of two C24 fatty acids containing hydroxyl groups at the 7 and 18 carbon atoms as major components of the seed oil of a native Chinese Brassicaceae species, Orychophragmus violaceus. Biochemical and genetic evidence are presented for premature or ‘discontinuous’ elongation of a 3-OH intermediate by a divergent beta-ketoacyl synthase as the origin of the 7-OH group of the dihydroxy fatty acids. Tribology studies revealed superior high-temperature lubricant properties for O. violaceus seed oil compared to castor oil, a high-performance vegetable oil lubricant. These findings provide a direct pathway for designing a new class of environmentally friendly plant-based and semisynthetic lubricants and unveil the potential of O. violaceus as a new industrial oilseed crop.

High temperature lubricants from novel hydroxylated fatty acid esters

2019 Spring National Meeting

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