SYNTHESIS OF MONOEPOXIDES OF ARACHIDONIC, EICOSAPENTAENOIC AND DOCOSAHEXAENOIC ACIDS

被引：0
|
作者：
KUKLEV, DV
RYBIN, VG
IMBS, AB
BEZUGLOV, VV
机构：
[1] RUSSIAN ACAD SCI,INST MARINE BIOL,VLADIVOSTOK,RUSSIA
[2] YA OVCHINNIKOV BIOORGAN CHEM INST,MOSCOW,RUSSIA
来源：
BIOORGANICHESKAYA KHIMIYA | 1993年 / 19卷 / 11期
关键词：
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A practical synthesis of cis-monoepoxides from free arachidonic 20 : 4 (n - 6), eicosapentaenoic 20: 5 (n - 3) and docosahexaenoic 22 : 6 (n - 3) acids, their Cytochrome P-450 epoxygenase metabolites, is described. The free polyunsaturated fatty acids (PUFA) were oxidized each by 1.25 eq. m-chloroperbenzoic acid in ethanol to give a mixture of PUFAs' mono-epoxy derivatives (45%) which was separated by HPLC and the individual isomers were characterised by mass spectrometry. All regioisomers of the free PUFAs' cis-monoepoxides were thus obtained.
引用
收藏
页码：1122 / 1127
页数：6
相关论文
共 50 条
  • [1] Enzymatic Synthesis of Epoxidized Metabolites of Docosahexaenoic, Eicosapentaenoic, and Arachidonic Acids
    Woodman, Joseph W.
    Cinelli, Mans A.
    Scharmen-Burgdolf, Amy
    Lee, Kin Sing Stephen
    JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2019, (148):
  • [2] LIPOXYGENASE IN TROUT GILL TISSUE ACTING ON ARACHIDONIC, EICOSAPENTAENOIC AND DOCOSAHEXAENOIC ACIDS
    GERMAN, JB
    BRUCKNER, GG
    KINSELLA, JE
    BIOCHIMICA ET BIOPHYSICA ACTA, 1986, 875 (01) : 12 - 20
  • [3] Eicosapentaenoic and docosahexaenoic acids reduce arachidonic acid release by rat kidney microsomes
    Yeo, YK
    Lim, AY
    Lee, JY
    Kim, HJ
    Farkas, T
    Kim, DG
    JOURNAL OF BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1999, 32 (01): : 33 - 38
  • [4] Fatty Acids and Their Derivatives in Cardiovascular Disease: Arachidonic, Eicosapentaenoic, and Docosahexaenoic Acids and Their Byproducts, the Eicosanoids and Docosanoids
    Baum, Seth J.
    Hamm, Aidan
    CURRENT CARDIOVASCULAR RISK REPORTS, 2012, 6 (02)
  • [5] Fatty Acids and Their Derivatives in Cardiovascular Disease: Arachidonic, Eicosapentaenoic, and Docosahexaenoic Acids and Their Byproducts, the Eicosanoids and Docosanoids
    Seth J. Baum
    Aidan Hamm
    Current Cardiovascular Risk Reports, 2012, 6 (2) : 146 - 154
  • [6] Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids
    Morisseau, Christophe
    Inceoglu, Bora
    Schmelzer, Kara
    Tsai, Hsing-Ju
    Jinks, Steven L.
    Hegedus, Christine M.
    Hammock, Bruce D.
    JOURNAL OF LIPID RESEARCH, 2010, 51 (12) : 3481 - 3490
  • [7] METABOLISM OF ARACHIDONIC, EICOSAPENTAENOIC, AND DOCOSAHEXAENOIC ACIDS IN HEPG2 CELLS AND RAT HEPATOCYTES
    FUJIYAMAFUJIWARA, Y
    UMEDA, R
    IGARASHI, O
    JOURNAL OF NUTRITIONAL SCIENCE AND VITAMINOLOGY, 1992, 38 (04) : 329 - 334
  • [8] Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids
    Haraldsson, GG
    Halldorsson, A
    Kulås, E
    JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2000, 77 (11) : 1139 - 1145
  • [9] COX-2, aspirin and metabolism of arachidonic, eicosapentaenoic and docosahexaenoic acids and their physiological and clinical significance
    Poorani, R.
    Bhatt, Anant N.
    Dwarakanath, B. S.
    Das, Undurti N.
    EUROPEAN JOURNAL OF PHARMACOLOGY, 2016, 785 : 116 - 132
  • [10] Effect of arachidonic, eicosapentaenoic and docosahexaenoic acids on the oxidative status of C6 glioma cells
    Leonardi, F
    Attorri, L
    Di Benedetto, R
    Di Biase, A
    Sanchez, M
    Nardini, M
    Salvati, S
    FREE RADICAL RESEARCH, 2005, 39 (08) : 865 - 874
12345