Gas-phase Reagents for Carbon-Carbon Double Bond Location: New Applications. Part I-Nitric Oxide Chemical Ionization Mass Spectrometry of 1-O-Alkenylglycerols from the Deep-sea Shark Centrophorus Squamosus Liver Oil

• Published in: Journal of mass spectrometry. 1997-07, Vol.32 (7), p.723-727
• Main Authors: Sellier, Nicole, Bordier, Catherine, Kerhoas, Lucien, Einhorn, Jacques
• Format: Article
• Language: English
• Subjects: alkenylglycerol; Analytical, structural and metabolic biochemistry; Biological and medical sciences; Chemical and Process Engineering; chemical ionization mass spectrometry; deep-sea shark; double bond location; Engineering Sciences; Food engineering; Fundamental and applied biological sciences. Psychology; General pharmacology; Glycerolipids, phospholipids; Life Sciences; Lipids; Medical sciences; nitric oxide; Other biological molecules; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments
• ISSN: 1076-5174; 1096-9888
• DOI: 10.1002/(SICI)1096-9888(199707)32:7<723::AID-JMS524>3.0.CO;2-0

Nitric oxide chemical ionization (CI) mass spectrometry (MS) has proved to be a very efficient tool for locating the carbon–carbon double bond in monoalkenylglycerols of the HOCH2CHOHCH2O(CH2)nCH=CH(CH2)mCH3 type. Such compounds, e.g. containing a ω‐7 C16:1, ω‐8 C17:1 (minor) and ω‐9 C18:1 alkenyl chain, were extracted from the liver oil of the deep‐sea shark Centrophorus squamosus and found among the most characteristic substances of the species. Double bond location was unambiguously deduced from the abundant CH3(CH2)mCO+ acylium ion being produced when examining the permethylated compounds under gas chromato‐graphic (GC) nitric oxide CIMS conditions. This ion probably results, as suggested by GC/MS/MS studies, from mechanisms similar to those previously reported for mono‐ or bifunctional alkenes. © 1997 by John Wiley & Sons, Ltd.