Biosynthesis of pentahydroxystearic acid of cutin from linoleic acid in Rosmarinus officinalis |
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Authors: | R Croteau P E Kolattukudy |
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Institution: | Department of Agricultural Chemistry, Washington State University, Pullman, Washington 99163 USA |
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Abstract: | The hydroxyfatty acid polymer, cutin, is the structural component of plant cuticle. Combined gas chromatography-mass spectrometry of the hydrogenolysis and deuterolysis products of rosemary cutin (Rosmarinus officinalis) revealed a series of components suggesting the conversion of linoleic acid to 9,10,12,13,18-pentahydroxy-stearic acid. U-14C]Linoleic acid was incorporated into the insoluble residue of rapidly expanding rosemary leaves. Depolymerization of the insoluble material followed by isolation of individual components and chemical degradation studies showed that linoleic acid was directly converted into 18-hydroxylinoleic acid, 18-hydroxy-9, 10-epoxyoctadec-12-enoic acid, 9,10,18-trihydroxyoctadec-12-enoic acid, 9,10,18-trihydroxy-12,13-epoxystearic acid, and 9,10,12,13,18-pentahydroxystearic acid. These results strongly suggest that, in the biosynthesis of the phytopolymer, linoleic acid is first converted into 18-hydroxylinoleic acid and that this precursor then undergoes sequential epoxidation-hydration at the Δ9 and Δ12 double bonds to yield 9,10,12,13,18-pentahydroxystearic acid. |
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Keywords: | Author to whom inquiries should be made |
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