Regiospecific analysis of diricinoleoylacylglycerols in castor (Ricinus communis L.) oil by electrospray ionization-mass spectrometry.
HPLC fractions of diricinoleoylacylglycerols containing one non-ricinoleoyl chain from castor oil were used to identify the regiospecific location of this non-ricinoleoyl chain on the glycerol backbone using electrospray ionization-MS3 of lithium adducts. The regiospecific ions used were from the loss of alpha,beta-unsaturated fatty acid specific at the sn-2 position. The content of 1,3-diricinoleoyl-2-oleoyl-sn-glycerols (ROR) among the three stereospecific isomers, RRO, ROR and ORR, was about 91%. The contents of other 1,3-diricinoleoyl-2-acyl-glycerols among the three stereospecific isomers were as follows: 1,3-diricinoleoyl-2-linoleoyl-sn-glycerol, 95%; 1,3-diricinoleoyl-2-linolenoyl-sn-glycerol, 96%; 1,3-diricinoleoyl-2-stearoyl-sn-glycerol, 96%; 1,3-diricinoleoyl-2-palmitoyl-sn-glycerol, 78%; and 1,3-diricinoleoyl-2-lesqueroloyl-sn-glycerol, 31%. These non-hydroxyl fatty acids were mostly at the sn-2 position of triacylglycerols in castor oil. These results suggest that phospholipase A2 hydrolysis of phosphatidylcholine (PC) containing non-hydroxyl fatty acid at the sn-2 position is either blocked or partially blocked in vivo. Phospholipase A2 hydrolysis of 2-lesqueroloyl-PC is not blocked and is similar to that of 2-ricinoleoyl-PC. Transgenic inhibition of phospholipase C hydrolysis of PC might be used to block the incorporation of non-hydroxyl fatty acids into triacylglycerols, thus increasing the content of ricinoleate in seed oil.
Lin
Jiann-Tsyh
JT
Western Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture, 800 Buchanan Street, Albany, California 94710, USA. jtlin@pw.usda.gov
Arcinas
Arthur
A
D002368:Castor Oil / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005990:Glycerol / Q000032:analysis*; D010741:Phospholipases A / Q000378:metabolism; D054467:Phospholipases A2; D012277:Ricinoleic Acids / Q000032:analysis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D010738:Type C Phospholipases / Q000378:metabolism
D012277:Ricinoleic Acids; D002368:Castor Oil; D010741:Phospholipases A; D054467:Phospholipases A2; D010738:Type C Phospholipases; D005990:Glycerol