Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid.
The occurrence of petroselinic acid (18:1delta6cis) in seed oils was believed to be limited to the Umbelliferae or Apiaceae, and a few other members of the Umbelliflorae. A major occurrence of petroselinic acid outside the Umbelliflorae must therefore be regarded as highly unusual and surprising. The seed oil of Geranium sanguineum, a member of the family Geraniaceae, has now been found to contain petroselinic and vernolic acids as major FA in its seed oil TAG. These unusual FA have not been reported previously as constituents of Geraniaceae seed oils. The structure and composition of the seed oil FA from G. sanguineum were determined by combined use of chromatographic (TLC, capillary GLC) and spectroscopic (IR, GC-MS) techniques. The double-bond position in petroselinic acid was located unambiguously by the characteristic mass fragmentation of its dimethyldisulfide (DMDS) adduct. The epoxy FA was identified as vernolic acid by co-chromatography and by the mass fragments formed during GC-MS of the products of the epoxy ring-opening reaction with BF3 in methanol.
Tsevegsuren
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N
Department of Organic & Food Chemistry, Faculty of Chemistry, National University of Mongolia, Ulaanbaatar, Mongolia.
Aitzetmuller
K
K
Vosmann
K
K
D002845:Chromatography; D004852:Epoxy Compounds / Q000302:isolation & purification*; D005227:Fatty Acids / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D031315:Geranium / Q000737:chemistry*; D009829:Oleic Acids / Q000302:isolation & purification*; D010938:Plant Oils / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D013057:Spectrum Analysis
D004852:Epoxy Compounds; D005227:Fatty Acids; D009829:Oleic Acids; D010938:Plant Oils; C008820:petroselinic acid; C081136:vernolic acid