2097130-84-0Relevant articles and documents
Stereochemistry of Endogenous Palmitic Acid Ester of 9-Hydroxystearic Acid and Relevance of Absolute Configuration to Regulation
Nelson, Andrew T.,Kolar, Matthew J.,Chu, Qian,Syed, Ismail,Kahn, Barbara B.,Saghatelian, Alan,Siegel, Dionicio
, p. 4943 - 4947 (2017)
Lipids have fundamental roles in the structure, energetics, and signaling of cells and organisms. The recent discovery of fatty acid esters of hydroxy fatty acids (FAHFAs), lipids with potent antidiabetic and anti-inflammatory activities, indicates that our understanding of the composition of lipidome and the function of lipids is incomplete. The ability to synthesize and test FAHFAs was critical in elucidating the roles of these lipids, but these studies were performed with racemic mixtures, and the role of stereochemistry remains unexplored. Here, we synthesized the R- and S- palmitic acid ester of 9-hydroxystearic acid (R-9-PAHSA, S-9-PAHSA). Access to highly enantioenriched PAHSAs enabled the development of a liquid chromatography-mass spectrometry (LC-MS) method to separate and quantify R- and S-9-PAHSA, and this approach identified R-9-PAHSA as the predominant stereoisomer that accumulates in adipose tissues from transgenic mice where FAHFAs were first discovered. Furthermore, biochemical analysis of 9-PAHSA biosynthesis and degradation indicate that the enzymes and pathways for PAHSA production are stereospecific, with cell lines favoring the production of R-9-PAHSA and carboxyl ester lipase (CEL), a PAHSA degradative enzyme, selectively hydrolyzing S-9-PAHSA. These studies highlight the role of stereochemistry in the production and degradation of PAHSAs and define the endogenous stereochemistry of 9-PAHSA in adipose tissue. This information will be useful in the identification and characterization of the pathway responsible for PAHSA biosynthesis, and access to enantiopure PAHSAs will elucidate the role of stereochemistry in PAHSA activity and metabolism in vivo.
Asymmetric Synthesis of Saturated Hydroxy Fatty Acids and Fatty Acid Esters of Hydroxy Fatty Acids
Mountanea, Olga G.,Limnios, Dimitris,Kokotou, Maroula G.,Bourboula, Asimina,Kokotos, George
, p. 2010 - 2019 (2019/03/07)
The recent discovery of a novel class of endogenous lipids, named Fatty Acid esters of Hydroxy Fatty Acids (FAHFAs), that present antidiabetic and anti-inflammatory activities, has attracted the interest on hydroxy fatty acids (HFAs) and their derivatives
Organic matter enantiomer pure OA and uses of organic matter enantiomer pure OA in preparation of drugs for type 2 diabetes and vascular complications
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, (2018/09/08)
The invention belongs to the technical field of medicinal chemistry and medicine, and relates to a novel organic matter enantiomer pure octadecanoic acid (OA) extracted from natural food, a preparation method and uses thereof. According to the present invention, the test results show that OA has good pharmacological activity and pharmacokinetic properties in the fields of blood glucose lowering, blood fat regulating, inflammation resistance, insulin sensitivity enhancement and the like, and can further be used as the active ingredient to preparing pharmacological compounds for treatment of various diabetic complications including but being not limited to atherosclerosis, cardiovascular and cerebrovascular diseases, lower extremity atherosclerosis, diabetic foot, diabetic peripheral neuropathy, diabetic nephropathy, diabetic cognitive dysfunction, diabetic retinopathy and the like; the preparation method has characteristics of relatively simple operation, easy industrial production andthe like; and the organic matter enantiomer pure OA of the present invention has significantly enhanced blood glucose lowering activity, significantly enhanced blood fat regulating activity and significantly enhanced anti-inflammatory activity compared to the un-modified OA, and further ha excellent pharmacokinetics. The structure of the organic matter enantiomer pure OA is defined in the specification.
