927-38-8Relevant academic research and scientific papers
10(S)-hydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of oleic acid to 7,10-dihydroxy-8(E)-octadecenoic acid
Kim, Hakryul,Gardner, Harold W.,Hou, Ching T.
, p. 95 - 99 (2000)
The new microbial isolate Pseudomonas aeruginosa (PR3) has been reported to produce from oleic acid a new compound, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD), with 10-hydroxy-8-octadecenoic acid (HOD) being a probable intermediate. The production of DOD involves the introduction of two hydroxyl groups at carbon numbers 7 and 10, and a rearrangement of the double bond from carbons 9-10 to 8-9. It has been shown that the 8-9 unsaturation of HOD was possibly in the cis configuration. Now we report that the rearranged double bond of HOD is trans rather than cis, as determined by spectral data. Also, it was found that the 10-hydroxyl was in the S-configuration as determined by gas chromatographic separation of R- and S-isomers after preparation of the (-)-menthoxycarbonyl derivative of the hydroxyl group followed by oxidative cleavage of the double bond and methyl esterification. This latter result coincides with our recent finding that the main final product, DOD, is in the 7(S),10(S)-dihydroxy configuration. In addition, a minor isomer of HOD (about 3%) with the 10(R)-hydroxyl configuration was also detected. From the data obtained herein, we concluded that 10(S)-hydroxy-8(E)-octadecenoic acid is the probable intermediate in the bioconversion of oleic acid to 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid by PR3.
Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity
Ishibashi, Fumito,Kuwano, Kazuyoshi,Shibahara, Tomohiro,Zha, Shijiao
, (2020/06/05)
Bioassay-guided separation of a methanol extract of Tricleocarpa jejuensis by monitoring algicidal activity against the red tide phytoplankton Chattonella antiqua led to the isolation of an active fraction consisting of a mixture of four isomeric compounds. The active compounds were identified as (E)-9-hydroxyoctadec-10-enoic acid (1), (E)-10-hydroxyoctadec-8-enoic acid (2), (E)-11-hydroxyoctadec-12-enoic acid (3) and (E)-12-hydroxyoctadec-10-enoic acid (4) by NMR, IR and mass spectral data. The structures were confirmed by comparison of the NMR and MS data with those of authentic samples of 1–4 obtained by unambiguous syntheses. Synthesized hydroxy acids 1–4 and related compounds were assessed for algicidal activity against C. antiqua and it was found that all of 1–4 had high activity (>80% mortality at 24 h) at a concentration of 20 μg/mL. A structure–activity relationship study using 11 related compounds revealed that the presence of the hydroxyl group is important for the activity and the double bond may be replaced with a triple bond.
Production of 10(S)-hydroxy-8(E)-octadecenoic acid mono-estolides by lipases in non-aqueous media
Martin-Arjol,Busquets,Manresa
, p. 224 - 230 (2013/05/22)
In this study, Novozym 435, a lipase B from Candida antarctica, was used for fatty acid polymerization. For the first time, an apolar reaction media, n-hexane, was used to synthesize in vitro estolides from trans-hydroxy-fatty acids derived from the biotransformation of oleic acid by Pseudomonas aeruginosa 42A2 NCIMB 40045. We studied the effects of the substrate, the enzyme ratio, the enzyme stability and the reusability of the biocatalyst. To determine the structure of the oligomers formed, both liquid chromatography mass spectrometry and MALDI-TOF mass spectrometry, with a DHB matrix neutralized with lithium hydroxide, were used to obtain simpler mass spectra. Estolides composed of two units of (10S)-HOME were synthesized with a reaction yield of 30%. Finally, various lipases were screened, and another apolar organic solvent, iso-octane, was assayed to try to increase the reaction yield.
PpoC from Aspergillus nidulans is a fusion protein with only one active haem
Brodhun, Florian,Schneider, Stefan,Goebel, Cornelia,Hornung, Ellen,Feussner, Ivo
experimental part, p. 553 - 565 (2011/02/23)
In Aspergillus nidulans Ppos [psi (precocious sexual inducer)-producing oxygenases] are required for the production of so-called psi factors, compounds that control the balance between the sexual and asexual life cycle of the fungus. The genome of A. nidulans harbours three different ppo genes: ppoA, ppoB and ppoC. For all three enzymes two different haem-containing domains are predicted: a fatty acid haem peroxidase/ dioxygenase domain in the N-terminal region and a P450 haem-thiolate domain in the C-terminal region. Whereas PpoA was shown to use both haem domains for its bifunctional catalytic activity (linoleic acid 8-dioxygenation and 8-hydroperoxide isomerization), we found that PpoC apparently only harbours a functional haem peroxidase/dioxygenase domain. Consequently, we observed that PpoC catalyses mainly the dioxygenation of linoleic acid (18:2Δ 9Z,12Z), yielding 10-HPODE (10-hydroperoxyoctadecadienoic acid). No isomerase activity was detected. Additionally, 10-HPODE was converted at lower rates into 10-KODE (10-keto-octadecadienoic acid) and 10-HODE (10-hydroxyoctadecadienoic acid). In parallel, decomposition of 10-HPODE into 10-ODA (10-octadecynoic acid) and volatile C-8 alcohols that are, among other things, responsible for the characteristic mushroom flavour. Besides these principle differences we also found that PpoA and PpoC can convert 8-HPODE and 10-HPODE into the respective epoxy alcohols: 12,13-epoxy-8-HOME (where HOME is hydroxyoctadecenoic acid) and 12,13-epoxy-10-HOME. By using site-directed mutagenesis we demonstrated that both enzymes share a similar mechanism for the oxidation of 18:2Δ9Z,12Z; they both use a conserved tyrosine residue for catalysis and the directed oxygenation at the C-8 and C-10 is most likely controlled by conserved valine/leucine residues in the dioxygenase domain. The Authors Journal compilation
Natural Estolides Produced by Pseudomonas sp. 42A2 Grown on Oleic Acid: Production and Characterization
Pelaez,Orellana,Marques,Busquets,Guerrero,Manresa
, p. 859 - 866 (2007/10/03)
Estolides are a group of FA polyesters resulting from ester bond formation between a hydroxyi or olefinic group of one FA and the terminal carboxyl group of a second FA. These products are commonly found in trace amounts, forming tetraglycerides in several oil seed plants, and have been produced by acid clay and enzymatic catalysis in vitro. In this study, natural estolides produced by a bacterial culture are presented for the first time. Pseudomonas sp. 42A2 produced (E)-10-hydroxy-8-octadecenoic acid and (E)-7,10-dihydroxy-8-octadecenoic acid when grown on oleic acid. It is suggested that these FA were polymerized in culture by a lipase produced by the bacterial strain, resulting in a mixture of estolides. These compounds amounted to 3.8 g/L after 72 h of incubation. LC-MS analysis indicated that the types of estolides formed were dimers (m/z 560-610), trimers (m/z 845-906), tetramers (m/z 1122-1202), pentamers (m/z 1328-1424), and hexarners (m/z 1554-1788), with a relative abundance of 27.5, 19.4, 15, 9.7, and 11%, respectively. This is the first report in which hexamers were detected in a bacterial culture.
Preparation of fatty acid cholesterol ester hydroperoxides by photosensitized oxidation
El Hafidi,Michel,Bascoul,Crastes De Paulet
, p. 127 - 138 (2007/10/03)
Preparation of fatty acid cholesterol ester hydroperoxides was undertaken with the purpose of evaluating their biological effects on cell growth. Cholesterol stearate, oleate, linoleate and α-linolenate were oxidized using methylene blue as a photosensitizer. The structures of all compounds were established by mass spectrometry and by nuclear magnetic resonance. The photosensitized oxidation of cholesterol oleate gave two hydroperoxide isomers: 9-hydroperoxy-trans-10-octadecenoate, and 10-hydroperoxy-trans-8-octadecenoate. In the case of the cholesterol linoleate, hydroperoxide isomers formed were: 9-hydroperoxy-trans-10, cis-12-octadecadienoate; 10-hydroperoxy-trans-8, cis-12-octadecadienoate; 12-hydroperoxy-cis-9, trans-13-octadecadienoate; 13-hydroperoxy-cis-9, trans-11-octadecadienoate. The oxidation of the cholesterol α-linolenate gave a mixture of six hydroperoxide isomers, at positions 9, 10, 12, 13, 15 and 16 of the fatty acid chain. The photosensitized oxidation of cholesterol stearate produced a formation of hydroperoxide at position 5α of cholesterol. The same hydroperoxide isomers on the fatty acid chain were obtained as described in the literature for the fatty acid methyl esters. Copyright (C) 1999 Elsevier Science Ireland Ltd.
A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids
Zhang, Lian-Ying,Hamberg, Mats
, p. 151 - 161 (2007/10/02)
A method was developed for assignment of the absolute configuration of oxylipin-derived 2-hydroxy acids, 3-hydroxy acids and 2,3-dihydroxy acids.The monohydroxy acids were converted into diastereomeric N-(propionoxyacyl)-L-phenylalanine-methyl ester (PAP) derivatives by coupling to the methyl ester of L-phenylalanine followed by propionylation, whereas 2,3-dihydroxy acids were derivatized by treatment with L-phenylalanine methyl ester followed by acetone and perchloric acid, to afford diastereomeric N-(2,3-isopropylidenedioxyacyl)-L-phenylalanine methyl ester (IAP) derivatives.The PAP and IAP derivatives were readily resolved by capillary gas-liquid chromatography.In addition, the method described allowed steric analysis of 3-hydroxy-3-methylheptanoic acid, a branched chain hydroxy acid derived from the prostaglandin analogue, misoprostol. - Keywords: Hydroxy acid; Phenylalanine; Steric analysis; Gas-liquid chromatography
Titanium(III) mediated regiospecific reduction of vinyl epoxides
Yadav,Shekharam,Srinivas
, p. 7973 - 7976 (2007/10/02)
A highly regiospecific reduction of vinyl epoxides to allyl alcohols with Cp2TiCl is described.
ISOMERIZATION OF EPOXIDES TO ALLYLIC ALCOHOLS USING METHYLMAGNESIUM N-CYCLOHEXYLISOPROPYLAMIDE
Mosset, Paul,Manna, Sukumar,Viala, Jacques,Falck, J.R.
, p. 299 - 302 (2007/10/02)
The scope of methylmagnesium N-cyclohexylisopropylamide promoted isomerizations of epoxides to allylic alcohols is described.
