title: Unusual fatty acids in the fat body of the early nesting bumblebee, Bombus pratorum.
abstract: Unusual fatty acids with 24, 26, and 28 carbon atoms were found in triacylglycerols (TAGs) isolated from fat body tissue of bumblebee Bombus pratorum. The most abundant one was (Z,Z)-9,19-hexacosadienoic acid. Its structure was determined by mass spectrometry after derivatization with dimethyl disulfide and by infrared spectroscopy. ECL (equivalent chain length) values of its methyl ester were determined on both DB-1 and DB-WAX capillary columns. (Z,Z)-9,19-Hexacosadienoic acid is quite rare in nature. So far it has been identified only in marine sponges, and this work is the first evidence of its occurrence in a terrestrial organism. HPLC/MS analysis of the bumblebee TAGs showed that (Z,Z)-9,19-hexacosadienoic acid is present in one third of all TAG molecular species. As it was found in all sn-TAG positions, it is likely that (Z,Z)-9,19-hexacosadienoic acid is transported to tissues. Interestingly, labial gland secretion of B. pratorum was found to contain (Z,Z)-7,17-pentacosadiene, a hydrocarbon with markedly similar double bond positions and geometry. Possible biosynthetic relationships between these two compounds are discussed.
authors: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague, Czech Republic.
authors: Josef
authors: J
authors: Cvacka
authors: Edita
authors: E
authors: Kofronová
authors: Sona
authors: S
authors: Vasícková
authors: Karel
authors: K
authors: Stránský
authors: Pavel
authors: P
authors: Jiros
authors: Oldrich
authors: O
authors: Hovorka
authors: Jirí
authors: J
authors: Kindl
authors: Irena
authors: I
authors: Valterová
mesh_terms: D000818:Animals; D001516:Bees / Q000378:metabolism*; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D004951:Esterification; D005216:Fat Body / Q000378:metabolism*; D005227:Fatty Acids / Q000378:metabolism*; D013058:Mass Spectrometry; D009425:Nesting Behavior; D014280:Triglycerides / Q000378:metabolism
chemical_list: D005227:Fatty Acids; D014280:Triglycerides