29907-57-1Relevant articles and documents
Synthesis of (E)-9,10,13-trihydroxy-11-octadecanoic acids
Kato,Hirukawa,Yano
, p. 839 - 842 (1994)
Our previous research concerning anti-rice blast fungus substances from the rice plants has led to the isolation of various types of oxygenated fatty acids as exemplified by 9,12,13-trihydroxy C-18 fatty acid. The fatty acids play an important role in the defense of the rice plants against this fungus. For evaluation of biological activity, we needed the isomeric trihydroxy fatty acids. This paper describes the synthesis of four stereoisomers of 9,10,13-trihydroxy fatty acid.
Characterization of Bitter-Tasting Oxylipins in Poppy Seeds (Papaver somniferum L.)
Lainer, Johanna,Dawid, Corinna,Dunkel, Andreas,Glaser, Peter,Wittl, Stephanie,Hofmann, Thomas
, p. 10361 - 10373 (2020/01/31)
Activity-guided fractionation of poppy seed (Papaver somniferum L.) extracts and analysis of fatty acid oxidation model experiments, followed by liquid chromatography time-of-flight mass spectrometry, tandem mass spectrometry, and one-/two-dimensional nuclear magnetic resonance experiments, revealed the chemical structures of five bitter-tasting fatty acids (1-5), three monoglycerides (6-8), six C18-lipidoxidation products (9-14), and four lipid oxidation degradation products (15 and 17-19) as well as two previously unreported monoglyceride oxidation degradation products, namely, 9-(2′,3′-dihydroxypropyloxy)-9-oxononaic acid (1-azeloyl-rac-glycerol, 16) and 1-(2′,3′-dihydroxypropyl)-8-(5″-oxo-2″,5″-dihydrofruan-2″-yl)-octonoate (1-ODFO-rac-glycerol, 20). Sensory studies exhibited low bitter taste threshold concentrations between 0.08 and 0.29 mmol/L, particularly for the higher oxidated C18-fatty acids trihydroxyoctadecenoic acid (THOE, 12), 12,13-dihydroxy-9-oxo-10-octadecenoic acid (12,13-diOH-9-oxo, 13), and 9,10-dihydroxy-13-oxo-11-octadecenoic acid (9,10-diOH-13-oxo, 14) as well as for the lipidoxidation degradation products 4-hydroxy-2-noneic acid (4-HNA, 17), 4-hydroxy-2-docecendienoic acid (HDdiA, 18), and 8-(5′-oxo-2′,5′-dihydrofuran-2′-yl)-octanoic acid (ODFO, 20).
FATTY ACID DERIVATIVES AND THEIR USE
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, (2019/01/21)
This disclosure concerns fatty acid derivatives, pharmaceutical compositions comprising the fatty acid derivatives, and methods of using the fatty acid derivatives, for example, to treat inflammation, chronic itch, chronic pain, an autoimmune disorder, atherosclerosis, a skin disorder, arthritis, a neurodegenerative disorder, or a psychiatric disorder in a subject. In some embodiments, the fatty acid derivative is a compound, or a stereoisomer, tautomer, or pharmaceutically acceptable salt thereof, having a structure according to: (I) wherein X is from 1-16 carbons in length, Z is aliphatic from 1-16 carbons in length, or is not present, Y is selected from: (II) R1, R2, and R3 are independently hydrogen or lower alkyl, R4 is lower alkyl, hydroxyl, carboxyl, or amine, R5 is hydrogen, lower alkyl, or halide, R6 is hydroxyl or substituted thiol, and each R7 is independently hydrogen or fluoride or is not present and the adjacent carbons form alkyne.
Catalytic activities of mammalian epoxide hydrolases with cis and trans fatty acid epoxides relevant to skin barrier function
Yamanashi, Haruto,Boeglin, William E.,Morisseau, Christophe,Davis, Robert W.,Sulikowski, Gary A.,Hammock, Bruce D.,Brash, Alan R.
, p. 684 - 695 (2018/04/12)
Lipoxygenase (LOX)-catalyzed oxidation of the essential fatty acid, linoleate, represents a vital step in construction of the mammalian epidermal permeability barrier. Analysis of epidermal lipids indicates that linoleate is converted to a trihydroxy derivative by hydrolysis of an epoxy-hydroxy precursor. We evaluated different epoxide hydrolase (EH) enzymes in the hydrolysis of skin-relevant fatty acid epoxides and compared the products to those of acid-catalyzed hydrolysis. In the absence of enzyme, exposure to pH 5 or pH 6 at 37°C for 30 min hydrolyzed fatty acid allylic epoxyalcohols to four trihydroxy products. By contrast, human soluble EH [sEH (EPHX2)] and human or murine epoxide hydrolase-3 [EH3 (EPHX3)] hydrolyzed cis or trans allylic epoxides to single diastereomers, identical to the major isomers detected in epidermis. Microsomal EH [mEH (EPHX1)] was inactive with these substrates. At low substrate concentrations (10 μM), EPHX2 hydrolyzed 14,15-epoxye-icosatrienoic acid (EET) at twice the rate of the epidermal epoxyalcohol, 9R,10R-trans-epoxy-11E-13R-hydroxy-octadec-enoic acid, whereas human or murine EPHX3 hydrolyzed the allylic epoxyalcohol at 31-fold and 39-fold higher rates, respectively. These data implicate the activities of EPHX2 and EPHX3 in production of the linoleate triols detected as end products of the 12R-LOX pathway in the epidermis and implicate their functioning in formation of the mammalian water permeability barrier.
Glycinoeclepins, Natural Hatching Stimuli for the Soybean Cyst Nematode, Heterodera Glycines. I. Isolation
Masamune, Tadashi,Anetai, Masaki,Fukuzawa, Akio,Tagasuki, Mitsuo,Matsue, Hideki,et al.
, p. 981 - 1000 (2007/10/02)
Hatching stimuli, designated as glycinoeclepins, for the soybean cyst nematode (Heterodera glycines) have been isolated by repeated chromatography of the aqueous extracts of dried roots of kidney bean (Phaseolus vulgaris), one of the host plants of the nematode.One of these compounds, glycinoeclepin A, stimulates the hatching and emergence of larvae in vitro in highly diluted aqueous solutions.
