Structure analysis of an allene-containing estolide tetraester triglyceride in the seed oil of Sebastiana commersoniana (Euphorbiaceae).
The seed oil of Sebastiana commersoniana (Euphorbiaceae) was separated into triglyceride and an estolide fraction by preparative thin-layer chromatography. The triglyceride band was characterized by spectroscopic methods, and its fatty acids have been analyzed by gas chromatography (GC) and GC-mass spectrometry (MS) as their methyl esters. Linolenic acid was the main fatty acid (65%). The estolide band was examined by a combination of spectroscopic and chromatographic methods (ultraviolet, infrared, nuclear magnetic resonance, fast atom bombardment-MS, GC-MS of the fatty acids before and after silylation) and was identified as a tetraglyceride, where one alpha-carbon of the triglyceride backbone was esterfied with 8-hydroxy-5,6-octadienoic acid, which itself was esterfied with trans-2,cis-4-decadienoic acid. The remaining positions of the triglyceride backbone were occupied by common fatty acids.
Spitzer
V
V
Faculty of Pharmacy, Federal University of Rio Grande do Sul (UFRGS), Porto Alerge/RS, Brazil.
Tomberg
W
W
Pohlentz
G
G
D000466:Alkadienes / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D004952:Esters / Q000737:chemistry; D005227:Fatty Acids / Q000032:analysis / Q000737:chemistry; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010938:Plant Oils / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*; D013020:South America; D017550:Spectroscopy, Fourier Transform Infrared; D014280:Triglycerides / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry; D017962:alpha-Linolenic Acid / Q000032:analysis
C106986:8-hydroxy-5,6-octadienoic acid; D000466:Alkadienes; D004952:Esters; D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D010938:Plant Oils; D014280:Triglycerides; D014297:Trimethylsilyl Compounds; D017962:alpha-Linolenic Acid; C025947:propadiene