Wax ester-synthesizing activity of lipases.
The synthesis/hydrolysis of wax esters was studied in an aqueous solution using purified rat pancreatic lipase, porcine pancreatic carboxylester lipase, and Pseudomonas fluorescens lipase. The equilibrium between wax ester synthesis and hydrolysis favored ester formation at neutral pH. The synthesizing activities were measured using free fatty acid or triacylglycerol as the acyl donor and an equimolar amount of long-chain alcohol as the acyl acceptor. When oleic acid and hexadecanol emulsified with gum arabic were incubated with these lipases, wax ester was synthesized, in a dose- and time-dependent manner, and the apparent equilibrium ratio of palmityl oleate/free oleic acid was about 0.9/0.1. These lipases catalyzed the hydrolysis of palmityl oleate emulsified with gum arabic, and the apparent equilibrium ratio of palmityl oleate/free oleic acid was also about 0.9/0.1. The apparent equilibrium ratio of wax ester/free fatty acid catalyzed by lipase depended on incubation pH and fatty alcohol chain length. When equimolar amounts of trioleoylglycerol and fatty acyl alcohol were incubated with pancreatic lipase, carboxylester lipase, or P. fluorescens lipase, wax esters were synthesized dose-dependently. These results suggest that lipases can catalyze the synthesis of wax esters from free fatty acids or through degradation of triacylglycerol in an aqueous medium.
Tsujita
T
T
Central Research Laboratory, School of Medicine, Ehime University, Onsen-gun, Japan. tsujita@m.ehime-u.ac.jp
Sumiyoshi
M
M
Okuda
H
H
D000255:Adenosine Triphosphate / Q000494:pharmacology; D000818:Animals; D003065:Coenzyme A / Q000494:pharmacology; D004952:Esters / Q000378:metabolism*; D005230:Fatty Acids, Nonesterified / Q000378:metabolism; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis*; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism*; D008274:Magnesium / Q000494:pharmacology; D019301:Oleic Acid / Q000378:metabolism; D010179:Pancreas / Q000201:enzymology; D011551:Pseudomonas fluorescens / Q000201:enzymology; D051381:Rats; D017208:Rats, Wistar; D012996:Solutions; D013552:Swine; D014280:Triglycerides / Q000378:metabolism; D014885:Waxes / Q000378:metabolism*
D004952:Esters; D005230:Fatty Acids, Nonesterified; D005231:Fatty Acids, Unsaturated; D005233:Fatty Alcohols; D012996:Solutions; D014280:Triglycerides; D014885:Waxes; D019301:Oleic Acid; C402677:palmityl oleate; D000255:Adenosine Triphosphate; D008049:Lipase; D008274:Magnesium; D003065:Coenzyme A