79790-32-2Relevant academic research and scientific papers
Bioactive constituents of Chinese natural medicines. I. New sesquiterpene ketones with vasorelaxant effect from Chinese moxa, the processed leaves of Artemisia argyi LEVL. et VANT.: Moxartenone and moxartenolide
Yoshikawa, Masayuki,Shimada, Hiromi,Matsuda, Hisashi,Yamahara, Johji,Murakami, Nobutoshi
, p. 1656 - 1662 (1996)
Two new sesquiterpene ketones, moxartenone and moxartenolide, and three octadecadienoic acids were isolated from Chinese moxa, the processed leaves of Artemisia argyi LEVL. et VANT., together with two sesquiterpenes, five triterpenes, two phenyl propanoids and three polyoxyflavones. The chemical structures of new sesquiterpenes, moxartenone, moxartenolide, and octadecadienoic acids were determined on the basis of chemical and physicochemical evidence. Moxartenolide was found to inhibit the contractions induced by a high concentration of K+, by norepinephrine, and by serotonin in isolated aortic strips of rat, while moxartenone showed little activity.
Quantitation of hydroperoxy-, keto- and hydroxy-dienes during oxidation of FAMEs from high-linoleic and high-oleic sunflower oils
Morales, Arturo,Dobarganes, Carmen,Marquez-Ruiz, Gloria,Velasco, Joaquin
experimental part, p. 1271 - 1279 (2011/08/21)
The objective of this work was to study the quantitative formation of hydroperoxydienes, ketodienes and hydroxydienes during autoxidation at 40 °C of fatty acid methyl esters derived from two sunflower oils with different degree of unsaturation, high-linoleic sunflower oil and high-oleic sunflower oil. The analysis of the oxidation compounds was carried out by NP-HPLC-UV and results were compared to the specific extinction at 232 nm (K 232) and the peroxide value (PV). Analysis of FAME polymers by HPSEC was also performed to discard samples of advanced oxidation. Results showed that the contents of hydroperoxydienes with respect to the PV were higher for the high linoleic (HL) sample. At the end of the period of slow polymerization (ΔPol ≤ 1 wt%), the content of hydroperoxydienes was found to be 86.0 and 30.7 μg/mg for the HL and high oleic (HO) samples, respectively. Throughout this period, hydroperoxydienes constituted around 90 and 50 wt% of the total hydroperoxides in the HL and HO samples, respectively, suggesting that a significant oxidation of oleic acid also occurred in both samples. The contents of ketodienes and hydroxydienes as a whole constituted 2-3 wt% of the diene compounds analyzed at the end of the period of slow polymerization. Higher contents of ketodienes than of hydroxydienes were found throughout the oxidation time, and the ratio between the contents of ketodienes and hydroxydienes increased with a factor that changed from 1 to 2 throughout the period of slow polymerization.
Biomimetic nitration of the linoleic acid metabolite 13-hydroxyoctadecadienoic acid: isolation and spectral characterization of novel chain-rearranged epoxy nitro derivatives
Manini, Paola,Camera, Emanuela,Picardo, Mauro,Napolitano, Alessandra,d'Ischia, Marco
, p. 51 - 61 (2008/09/20)
Nitration of unsaturated fatty acids is a (patho)physiologically important pathway of lipid modification induced by nitric oxide-derived species. We report herein on the unexpected chain rearrangement undergone by (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid (1), a linoleic acid metabolite, when exposed to nitrating agents of biological relevance. At pH 7.4 and at room temperature, reaction of 1 with peroxynitrite (ONOO-) as well as Fe2+-EDTA/H2O2/NO2- and horseradish peroxidase/H2O2/NO2- led to the formation of two nitration products, which could be isolated as the methyl esters and were identified as diastereoisomeric methyl (12S)-10,11-epoxy-12-hydroxy-9-nitromethylheptadecanoates by extensive 1H, 13C, 15N NMR and MS analysis.
Allylic oxidation: Easy synthesis of alkenones from activated alkenes with TEMPO
Breton, Tony,Liaigre, Denis,Belgsir, El Mustapha
, p. 2487 - 2490 (2007/10/03)
Activated alkenes and dienes are converted into the corresponding alkenone in excellent yields (>90%). In aqueous acetonitrile, the transformations are catalyzed by 2,2,6,6-tetramethyl-1-oxopiperidinium (TEMPO+) in the presence of water and 2,6-lutidine. TEMPO+ cations were regenerated electrochemically from the radical parent (TEMPO.) at a vitreous carbon anode.
Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols
Iacazio, Gilles
, p. 115 - 121 (2007/10/03)
Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH 4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides.
New geometric isomers of oxooctadecadienoate in copper-catalyzed decomposition products of linoleate hydroperoxide
Tokita, Masako,Iwahara, Jyunko,Morita, Makio
, p. 993 - 997 (2007/10/03)
Methyl linoleate hydroperoxide produced by autoxidation was refluxed with 10-4 M Cu-naphthenate in benzene. Two new geometrical isomers of oxooctadecadienoate (compounds I and II) were found in addition to the four known isomers. They were isolated by a Sephadex LH-20 column chromatography with chloroform-hexane (2:1) and purified by HPLC on Nucleosil 100-5 and Zorbax ODS columns. UV, IR, MS, and 1H-NMR spectra were measured. The geometry of conjugated dienes were assigned from the coupling constants of the olefinic protons. Compounds I and II were identified as 13-oxo-trans-9, cis-11- and 9-oxo-cis-10, trans-12-octadecadienoate, respectively. Each of them had a cis double bond adjacent to the oxo group. The hydroperoxides of the same geometry as compounds I and II were also detected in autoxidation products.
Evaluation of the Cytotoxic Activity of Chiral (E)-13-Hydroxy-10-oxo-11-octadecenoic Acid and Its Lactone
Hayashi, Yoshiki,Nishikawa, Yasushi,Mori, Hirotaka,Matsushita, Yoh-ichi,Sugamoto, Kazuhiro,Matsui, Takanao
, p. 1771 - 1773 (2007/10/03)
Both the S and R enantiomers of (E)-13-hydroxy-10-oxo-11-octadecenoic acid (1) and (E)-10-oxo-11-octadecen-13-olide (2) had similar IC50 values against P388 mouse leukemia cells; i.e. the stereochemistry of the asymmetric center of 1 and 2 had no influence on the cytotoxic activity. Bioassay results of various compounds related to 1 and 2 suggests that the 1O-oxo and lactone moieties of 2 were important for enhancing the cytotoxicity. - Keywords: corn; cytotoxicity; fatty acid; (E)-13-hydroxy-10-oxo-11octadecenoic acid; (E)-10-oxo-11-octadecen-13-olide.
Synthesis of keto- and hydroxydienoic compounds from linoleic acid
Kuklev, Dmitry V.,Christie, William W.,Durand, Thierry,Rossi, Jean Claude,Vidal, Jean Pierre,Kasyanov, Sergey P.,Akulin, Valery N.,Bezuglov, Vladimir V.
, p. 125 - 134 (2007/10/03)
A convenient preparative method has been developed for the synthesis of hydroxydienoic (9-HODE and 13-HODE) and ketodienoic compounds (9-KODE and 13-KODE) from natural linoleic acid. Methyl linoleate was treated with 1.25 eq. of m-chloroperbenzoic acid in alcoholic solution, giving a mixture of mono-epoxides (yield 60%), that was treated with a solution of HBr in MeOH to yield a mixture of the bromohydrins (yield 92%). The last was oxidized by Jones reagent to a mixture of bromoketones (yield 64%) and the mixture obtained was dehydrobrominated by DBU to produce a mixture of ketodienoic compounds (yield 94%). Reduction of the ketodienoic compounds by KBH4 in MeOH led to the corresponding hydroxydienoic (9-HODE and 13-HODE) methyl esters (yield 83%). The synthetic approach described is simple and gives reliable results. The keto- and hydroxy fatty acids obtained were characterized thoroughly by TLC, HPLC, UV, FT-IR, 1H-, 1H1H- and 13C-NMR.
IRON-PEPLOMYCIN CATALYZED OXYGENATION OF LINOLEIC ACID
Nagata, Ryu,Morimoto, Shinji,Saito, Isao
, p. 4485 - 4488 (2007/10/02)
Incubation of linoleic acid with Fe(III)-peplomycin under aerobic conditions produced a mixture of hydroperoxides 1a-d as primary products which then gave rise to the formation of the corresponding dienones (2a-d), alcohols (3a-d) and epoxyenones (4a,b).
