DEVELOPING A DOMESTIC SOURCE FOR PRODUCTION OF RICINOLEATE AND OTHER INDUSTRIAL-USE FATTY ACIDS
Location: Crop Improvement & Utilization Research
Title: Identification of (12-Ricinoleoyl-Ricinoleoyl)-Diricinoleoyl-Glycerol in Castor Oil by Esi-Ms/ms and Its Biosynthesis
Submitted to: American Oil Chemists' Society Meeting
Publication Type: Abstract Only
Publication Acceptance Date: March 15, 2006
Publication Date: April 29, 2006
Citation: Lin, J.T., Arcinas, A.J., Harden, L.A., Fagerquist, C.K. 2006. Identification of (12-ricinoleoyl-ricinoleoyl)-diricinoleoyl-glycerol in castor oil by esi-ms/ms and its biosynthesis. American Oil Chemists' Society Meeting.
Interpretive Summary: Acylglycerols (AG), an acyl lipid class, including the subclasses of triacylglycerols, diacylglycerols and monoacylglycerols, from various natural sources are the most abundant acyl lipid class. Ricinoleate (R), a hydroxy fatty acid (FA), has many industrial uses, such as the manufacture of aviation lubricant, plastics, paints and cosmetics. Ricinoleate occurs as AG in castor oil and about 70% of AG in castor oil is triricinolein (triricinoleoylglycerol, RRR). Glycerol contains three hydroxyl groups, therefore, up to three FA can be directly attached (esterified) to the glycerol to form AG. A fourth FA can be attached to a hydroxyl group on acyl chains. We have positively identified for the first time in a natural source a new AG containing four acyl chains, (12-ricinoleoyl-ricinoleoyl)-diricinoleoyl-glycerol (RRRR), in castor oil using ESI-MS (electrospray ionization-mass spectrometry). AG containing four acyl chains have been previously suggested or tentatively identified. However, this new acyl lipid subclass (acylacyl-diacyl-glycerol or tetraacylglycerols) was not included in the new comprehensive classification system for lipids shown in the May issue of the Journal of Lipid Research. The positive identification of an AG in a new subclass will add the new subclass into the comprehensive classification system for lipids and the new lipids will eventually become useful.
We have positively identified for the first time in a natural source a new acylglycerol (AG) containing four acyl chains, (12-ricinoleoyl-ricinoleoyl)-diricinoleoyl-glycerol (RRRR), in castor oil using ESI-MS (electrospray ionization-mass spectrometry). HPLC purified RRRR from castor oil was used for high resolution ESI-MS/MS. The precursor and fragment ions of [RRRR + Na]+ showed the exact masses and the fragment ions of both diacylglycerols and fatty acids were detected. Since in the study of ESI-MS/MS using [AG + NH4]' adducts, only fragment ions of diacylglycerol can be detected, therefore, using [AG + Na]' adducts is more informative than using [AG + NH4]'. Incorporation of radiolabeled triricinolein (RRR) into RRRR in castor microsomal incubation showed that RRRR is biosynthesized in castor bean. The newly identified RRRR is in the new subclass of acylacyl-diacyl-glycerol (or tetraacylglycerols) in the lipid class of AG.