Formation of novel poly(hydroxyalkanoates) from long-chain fatty acids.
Poly(hydroxyalkanoates) (PHAs) were isolated from Pseudomonas aeruginosa 44T1 cultivated on euphorbia oil and castor oil. With the aid of 2-D proton NMR spectra and proton-detected multiple bond coherence NMR spectra the structures of the PHAs were determined. In addition to the usual PHA constituents (C6-C14 3-hydroxy fatty acids), PHAs formed from euphorbia oil contained delta 8,9-epoxy-3-hydroxy-5c-tetradecenoate, and probably delta 6,7-epoxy-3-hydroxydodecanoate and delta 4,5-epoxy-3-hydroxydecanoate. These novel constituents account for approximately 15% of the total amount of monomers and are clearly generated via beta-oxidation of vernolic acid (delta 12,13-epoxy-9c-octadecenoic acid), the main component of euphorbia oil. In PHAs formed from castor oil, 7% of the monomers found were derived from ricinoleic acid (12-hydroxy-9c-octadecenoic acid). The presence of 3,8-dihydroxy-5c-tetradecenoate was clearly demonstrated. Furthermore, NMR analysis strongly suggested the presence of 3,6-dihydroxydodecanoate, 6-hydroxy-3c-dodecenoate, and 4-hydroxydecanoate.
Eggink
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Agrotechnological Research Institute (ATO-DLO), Wageningen, The Netherlands.
de Waard
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P
Huijberts
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GN
D002368:Castor Oil / Q000378:metabolism; D004852:Epoxy Compounds / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism*; D006880:Hydroxy Acids / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009829:Oleic Acids / Q000378:metabolism; D010084:Oxidation-Reduction; D010938:Plant Oils / Q000378:metabolism; D011091:Polyesters / Q000737:chemistry / Q000378:metabolism*; D011550:Pseudomonas aeruginosa / Q000378:metabolism*; D012277:Ricinoleic Acids / Q000378:metabolism
D004852:Epoxy Compounds; D005227:Fatty Acids; D006880:Hydroxy Acids; D009829:Oleic Acids; D010938:Plant Oils; D011091:Polyesters; D012277:Ricinoleic Acids; C081136:vernolic acid; D002368:Castor Oil; C030521:ricinoleic acid