Stereochemistry of Linoleic Acid Esters of Hydroxy Linoleic Acids

被引:9
作者
Wang, Huijing [1 ]
Kolar, Matthew J. [2 ]
Chang, Tina [2 ]
Rizo, Jose [1 ]
Konduri, Srihari [1 ]
McNerlin, Clare [1 ]
Saghatelian, Alan [2 ]
Siegel, Dionicio [1 ]
机构
[1] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, 9500 Gilman Dr, La Jolla, CA 92093 USA
[2] Salk Inst Biol Studies, Clayton Fdn Labs Peptide Biol, 10010 North Torrey Pines Rd, La Jolla, CA 92037 USA
关键词
FAHFAS;
D O I
10.1021/acs.orglett.9b03054
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of linoleic acid esters of hydroxy linoleic acids (LAHLAs) present in oat oil and human serum have been achieved, providing access to material for testing and the determination of the stereochemistry of the natural compounds. While 9- and 13-LAHLAs were found to be a mixture of enantiomers 15-LAHLA is generated in a single optical form in oat oil. The stereochemistry of 15-LAHLA in oat oil was found to be opposite to that reported for digalactosyldiacylglycerol that possesses an embedded 15-LAHLA.
引用
收藏
页码:8080 / 8084
页数:5
相关论文
共 30 条
[21]   First stereoselective total synthesis of Phomolide G and H via RCM protocol [J].
Ramesh, Palakuri ;
Reddy, B. Chennakesava ;
Meshram, H. M. .
TETRAHEDRON LETTERS, 2012, 53 (29) :3735-3738
[22]   A STEREOSELECTIVE SYNTHESIS OF CORIOLIC ACID AND DIMORPHECOLIC ACID [J].
RAO, AVR ;
REDDY, ER ;
SHARMA, GVM ;
YADAGIRI, P ;
YADAV, JS .
TETRAHEDRON LETTERS, 1985, 26 (04) :465-468
[23]   SHORT AND EFFICIENT SYNTHESES OF CORIOLIC ACID [J].
RAO, AVR ;
REDDY, SP ;
REDDY, ER .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) :4158-4159
[24]   Methodological Issues in Studying PAHSA Biology: Masking PAHSA Effects [J].
Syed, Ismail ;
Lee, Jennifer ;
Peroni, Odile D. ;
Yore, Mark M. ;
Moraes-Vieira, Pedro M. ;
Santoro, Anna ;
Wellenstein, Kerry ;
Smith, Ulf ;
McGraw, Timothy E. ;
Saghatelian, Alan ;
Kahn, Barbara B. .
CELL METABOLISM, 2018, 28 (04) :543-546
[25]   Palmitic Acid Hydroxystearic Acids Activate GPR40, Which Is Involved in Their Beneficial Effects on Glucose Homeostasis [J].
Syed, Ismail ;
Lee, Jennifer ;
Moraes-Vieira, Pedro M. ;
Donaldson, Cynthia J. ;
Sontheimer, Alexandra ;
Aryal, Pratik ;
Wellenstein, Kerry ;
Kolar, Matthew J. ;
Nelson, Andrew T. ;
Siegel, Dionicio ;
Mokrosinski, Jacek ;
Farooqi, I. Sadaf ;
Zhao, Juan Juan ;
Yore, Mark M. ;
Peroni, Odile D. ;
Saghatelian, Alan ;
Kahn, Barbara B. .
CELL METABOLISM, 2018, 27 (02) :419-+
[26]   Absence of Carbohydrate Response Element Binding Protein in Adipocytes Causes Systemic Insulin Resistance and Impairs Glucose Transport [J].
Vijayakumar, Archana ;
Aryal, Pratik ;
Wen, Jennifer ;
Syed, Ismail ;
Vazirani, Reema P. ;
Moraes-Vieira, Pedro M. ;
Camporez, Joao Paulo ;
Gallop, Molly R. ;
Perry, Rachel J. ;
Peroni, Odile D. ;
Shulman, Gerald I. ;
Saghatelian, Alan ;
McGraw, Timothy E. ;
Kahn, Barbara B. .
CELL REPORTS, 2017, 21 (04) :1021-1035
[27]   Synthesis of chemically edited derivatives of the endogenous regulator of inflammation 9-PAHSA [J].
Wang, Huijing ;
Chang, Tina ;
Konduri, Srihari ;
Huang, Jianbo ;
Saghatelian, Alan ;
Siegel, Dionicio .
JOURNAL OF ANTIBIOTICS, 2019, 72 (06) :498-506
[28]   Discovery of a Class of Endogenous Mammalian Lipids with Anti-Diabetic and Anti-inflammatory Effects [J].
Yore, Mark M. ;
Syed, Ismail ;
Moraes-Vieira, Pedro M. ;
Zhang, Tejia ;
Herman, Mark A. ;
Homan, Edwin A. ;
Patel, Rajesh T. ;
Lee, Jennifer ;
Chen, Shili ;
Peroni, Odile D. ;
Dhaneshwar, Abha S. ;
Hammarstedt, Ann ;
Smith, Ulf ;
McGraw, Timothy E. ;
Saghatelian, Alan ;
Kahn, Barbara B. .
CELL, 2014, 159 (02) :318-332
[29]   A LC-MS-based workflow for measurement of branched fatty acid esters of hydroxy fatty acids [J].
Zhang, Tejia ;
Chen, Shili ;
Syed, Ismail ;
Stahlman, Marcus ;
Kolar, Matthew J. ;
Homan, Edwin A. ;
Chu, Qian ;
Smith, Ulf ;
Boren, Jan ;
Kahn, Barbara B. ;
Saghatelian, Alan .
NATURE PROTOCOLS, 2016, 11 (04) :747-763
[30]   Comprehensive Screening and Identification of Fatty Acid Esters of Hydroxy Fatty Acids in Plant Tissues by Chemical Isotope Labeling Assisted Liquid Chromatography-Mass Spectrometry [J].
Zhu, Quan-Fei ;
Yan, Jing-Wen ;
Zhang, Tian-Yi ;
Xiao, Hua-Ming ;
Feng, Yu-Qi .
ANALYTICAL CHEMISTRY, 2018, 90 (16) :10056-10063