Improved Method for the Synthesis of trans-Feruloyl-β-sitostanol

Abstract

Phytosterols and phytostanols are known to lower low-density lipoprotein-cholesterol (LDL-C) levels in humans by up to 15%, and at least two products, Benecol and Take Control, are now on the market as naturally derived fatty acid esters of phytostanols (stanol esters) and phytosterols (sterol esters), respectively. A synthetic process was developed to synthesize gram quantities of trans-feruloyl-beta-sitostanol from ferulic acid and beta-sitostanol, with high purity and yields of approximately 60%. The process involves (a) condensation of trans-4-O-acetylferulic acid with the appropriate phytostanol or phytostanol mixture in the presence of N,N-dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine, (b) separation of the trans-4-O-acetylferuloyl products by preparative liquid chromatography, (c) selective deacetylation of the feruloyl acetate, and (d) chromatographic purification of the feruloylated phytostanols. The process was successfully applied to synthesize stanol trans-feruloyl esters from "Vegetable Stanols", a mixture of approximately 70:30 beta-sitostanol and beta-campestanol, in comparable purity and yield.

Novel Conjugates of 1,3-Diacylglycerol and Lipoic Acid: Synthesis, DPPH Assay, and RP-LC-MS-APCI Analysis

“…Fatty acids in 1,3-DAG are presumed to be utilized mainly for energy formation [2, 3]. It is common approach to synthesise new hybrid molecules with the anticipation of synergistic and/or dual effects due to their modified physical, chemical, and biological effects such as solubility and bioavailability, compared with the parent molecules [22, 24, 33, 34]. …”

The in vitro hydrolysis of phytosterol conjugates in food matrices by mammalian digestive enzymes

“…Oryzanol was purchased from CTS Organics (Atlanta, GA). Sitostanyl ferulate (~99%) was synthesized by the method of Condo et al (14). Take Control ® and Benecol ® were purchased at a local supermarket.…”

Corn fiber oil and sitostanol decrease cholesterol absorption independently of intestinal sterol transporters in hamsters

“…Except for the noncholesterol-control group, all diets contained 0.1% (wt/wt) cholesterol. Other dietary groups contained: (a) 10% CFO (USDA, Wyndmoor, PA); (b) 0.5% sitostanol (Research Plus, Manasaquan, NJ); (c) 0.23% ferulic acid (Sigma Chemical, St. Louis, MO); or (d) 0.73% FPE [19]. All diets contained 10 wt.% added fat provided in the form of a mixture of safflower oil and beef tallow to yield a polyunsaturated fatty acid/saturated fatty acid ratio of 0.4, while the CFO group contained 10 wt.% of CFO, replacing the 10 wt.% added fat.…”