Enzymatic synthesis of phytosteryl docosahexaneates and evaluation of their anti-atherogenic effects in apo-E deficient mice

• Published in: Food chemistry 2012-10, Vol.134 (4), p.2097-2104
• Main Authors: Tan, Zhuliang, Le, Khuong, Moghadasian, Mohammed, Shahidi, Fereidoon
• Format: Article
• Language: English
• Subjects: Animals; Apolipoproteins E - deficiency; Apolipoproteins E - genetics; Atherosclerosis - drug therapy; Atherosclerosis - etiology; Atherosclerosis - metabolism; Atherosclerosis - prevention & control; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Cholesterol lowering effect; Diet, Atherogenic - adverse effects; Docosahexaenoic Acids - administration & dosage; Docosahexaenoic Acids - chemical synthesis; Docosahexaenoic Acids - chemistry; Enzymatic synthesis; Esterification; Food industries; Fundamental and applied biological sciences. Psychology; Humans; Lipase - chemistry; Lipids - blood; Male; Methods. Procedures. Technologies; Mice; Mice, Inbred C57BL; Mice, Knockout; Molecular Structure; Phytosterols - administration & dosage; Phytosterols - chemical synthesis; Phytosterols - chemistry; Phytosteryl docosahexaneates
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2012.04.009

► Enzymatic synthesis of phytosteryl docosahexaneates was successful. ► Structures of phytosteryl docosahexaneates were confirmed by IR and HPLC–MS. ► The phytosteryl docosahexaneates had anti-atherogenic effects in apo-E deficient mice. ► Phytosteryl docosahexaneates may be used as functional foods ingredient/nutraceuticals. Phytosterols have attracted much attention in recent years due to their health benefits, such as cholesterol lowering, anti-inflammatory, anti-atherogenicity, and anti-cancer potential. Docosahexaenoic acid (DHA) has been demonstrated to possess cardioprotective and immune-enhancing effects. Esterification of phytosterols with DHA may render improved physiochemical properties such as solubility, miscibility, oxidative stability and hence bioactivity and bioavailability. Thus, phytosteryl docosahexaneates (PS-DHA) may offer both the benefits of phytosterols and DHA, possibly in a synergistic manner. Here, we describe a method for enzymatic synthesis of phytosteryl docosahexaneates and evaluation of metabolic and cardiovascular benefits in apo-E deficient (apo E-KO) mice. The structures of phytosteryl docosahexaneates were confirmed by infrared (IR) and high performance liquid chromatography–mass spectrometry (HPLC–MS) using both normal and reverse phase chromatography. Apo E-KO mice were fed with an atherogenic diet containing 2% (w/w) PS-DHA for 7weeks. Plasma lipid levels and the extent and complexity of atherosclerotic lesions were examined and compared with those in the control group. The PS-DHA-treated mice had significantly lower plasma cholesterol levels and three times smaller atherosclerotic lesions in the aortic roots. This pilot study suggests cardiovascular benefits for PS-DHA. Further experimental and clinical studies are needed to confirm such benefits of PS-DHA.