Lipase-catalyzed methanolysis of triricinolein in organic solvent to produce 1,2(2,3)-diricinolein.
The objective of this study was to find the optimal parameters for lipase-catalyzed methanolysis of triricinolein to produce 1,2(2,3)-diricinolein. Four different immobilized lipases were tested, Candida antarctica type B (CALB), Rhizomucor miehei (RML), Pseudomonas cepacia (PCL), and Penicillium roquefortii (PRL). n-Hexane and diisopropyl ether (DIPE) were examined as reaction media at three different water activities (a(w)), 0.11, 0.53, and 0.97. The consumption of triricinolein and the formation of 1,2(2,3)-diricinolein, methyl ricinoleate, and ricinoleic acid were followed for up to 48 h. PRL gave the highest yield of 1,2(2,3)-diricinolein. Moreover, this lipase showed the highest specificity for the studied reaction, i.e., high selectivity for the reaction with triricinolein but low for 1,2(2,3)-diricinolein. Recoveries of 93 and 88% DAG were obtained using PRL in DIPE at a(w) of 0.11 and 0.53, respectively. Further, NMR studies showed that a higher purity of the 1,2(2,3)-isomer vs. the 1,3-isomer was achieved at higher a(w) (88% at a(w) = 0.53), compared to lower a(w) (71% at a(w) = 0.11). The DAG obtained was acylated by the DAG acyltransferase from Arabidopsis thaliana. Therefore, this enzymatic product is a useful enzyme substrate for lipid biosynthesis. Accordingly, the use of PRL in DIPE at a(w) 0.53 is considered optimal for the synthesis of 1,2(2,3)-diricinolein from triricinolein.
Turner
Charlotta
C
Western Regional Research Center, USDA, Albany, California 94710, USA.
He
Xiaohua
X
Nguyen
Tasha
T
Lin
Jiann-Tsyh
JT
Wong
Rosalind Y
RY
Lundin
Robert E
RE
Harden
Leslie
L
McKeon
Thomas
T
D002851:Chromatography, High Pressure Liquid; D004800:Enzymes, Immobilized / Q000378:metabolism; D005230:Fatty Acids, Nonesterified / Q000378:metabolism; D005990:Glycerol / Q000378:metabolism; D008049:Lipase / Q000378:metabolism*; D050356:Lipid Metabolism; D008055:Lipids / Q000737:chemistry; D013058:Mass Spectrometry; D012278:Ricinus / Q000378:metabolism; D013997:Time Factors; D014280:Triglycerides / Q000378:metabolism
D004800:Enzymes, Immobilized; D005230:Fatty Acids, Nonesterified; D008055:Lipids; D014280:Triglycerides; D008049:Lipase; D005990:Glycerol