A novel compound, 7,10‐dihydroxy‐8(E)‐octadecenoic acid from oleic acid by bioconversion

Hou, Ching T.; Bagby, M. O.; Plattner, Ronald D.; Koritala, S.

doi:10.1007/bf02662326

Cited by 80 publications

(47 citation statements)

References 9 publications

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“…P450 catalyzes hydroxylation of the -end of fatty acids, epoxidation of double bonds, and hydroxylation with double bond migration (6). Oxygenation of fatty acids has mainly been studied in eukaryotes, but many studies now show that Pseudomonas aeruginosa can oxidize unsaturated fatty acids to hydroperoxy and dihydroxy metabolites (7)(8)(9)(10)(11)(12)(13)(14)(15).…”

Section: H]18:2n-6 and [8r-mentioning

confidence: 99%

“…In 1988, P. aeruginosa 42A2 was demonstrated to oxidize oleic acid to a new surfactant, a dihydroxy fatty acid metabolite (7). This product was later identified as (7S,10S)-dihydroxy-(8E)-octadecenoic acid ((7S,10S)-Di-HOME) by Hou and co-workers using the P. aeruginosa strain PR3 (8,10,15). We now know that production of (7S,10S)-DiHOME is a characteristic of P. aeruginosa (13).…”

Section: H]18:2n-6 and [8r-mentioning

confidence: 99%

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Biochemical Characterization of the Oxygenation of Unsaturated Fatty Acids by the Dioxygenase and Hydroperoxide Isomerase of Pseudomonas aeruginosa 42A2

Martínez

Hámberg

Busquets

et al. 2010

Journal of Biological Chemistry

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We have studied oxygenation of fatty acids by cell extract of Pseudomonas aeruginosa 42A2. Oleic acid ((9Z)-18:1) was transformed to (10S)-hydroperoxy-(8E)-octadecenoic acid ((10S)-HPOME) and to (7S,10S)-dihydroxy-(8E)-octadecenoic acid (7,10-DiHOME). Experiments under oxygen-18 showed that 7,10-DiHOME contained oxygen from air and was formed sequentially from (10S)-HPOME by isomerization. (10R)-HPOME was not isomerized. The (10S)-dioxygenase and hydroperoxide isomerase activities co-eluted on ion exchange chromatography and on gel filtration with an apparent molecular size of ϳ50 kDa. 16:1n-7, 18:2n-6, and 20:1n-11 were also oxygenated to 7,10-dihydroxy fatty acids, and ( 2 H]18:2n-6 as substrates. The pro-R hydrogen at C-8 was lost in the biosynthesis of (10S)-HPODE, whereas the pro-S hydrogen was lost and the pro-R hydrogen was retained at C-7 during biosynthesis of the 7,10-dihydroxy metabolites. Analysis of the fatty acid composition of P. aeruginosa revealed relatively large amounts of (9E/Z)-16:1 and (11E/Z)-18:1 and only traces of 18:1n-9. We found that (11Z)-18:1 (vaccenic acid) was transformed to (11S,14S)-dihydroxy-(12E)-octadecenoic acid and to a mixture of 11-and 12-HPOME, possibly due to reverse orientation of (11Z)-18:1 at the active site compared with oleic acid. The reaction mechanism of the hydroperoxide isomerase suggests catalytic similarities to cytochrome P450.

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Section: H]18:2n-6 and [8r-mentioning

confidence: 99%

Section: H]18:2n-6 and [8r-mentioning

confidence: 99%

Biochemical Characterization of the Oxygenation of Unsaturated Fatty Acids by the Dioxygenase and Hydroperoxide Isomerase of Pseudomonas aeruginosa 42A2

Martínez

Hámberg

Busquets

et al. 2010

Journal of Biological Chemistry

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“…3 This product was later identified as 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid (7,10-(OH) 2 -18:1) by Hou and coworkers using gas chromatography/mass spectrometry (GC/MS), nuclear magnetic resonance (NMR), infrared (IR), and steric analysis of the hydroxy groups after ozonolysis. 4,5 (for review, see Hou 6 ). In addition, P. aeruginosa also transformed oleic acid into 10(S)-hydroxy-8(E)-octadecenoic acid (10-OH-18:1) and 10(S)-hydroperoxy-8(E)-octadecenoic acid (10-OOH-18:1).…”

mentioning

confidence: 99%

“…10,[12][13][14] This was in contrast to its GC/MS spectrum. 4 The first goal of our study was to perform a systematic investigation of the MS/MS fragmentation mechanism of 7,10-(OH) 2 -18:1 and related dihydroxy fatty acids. We used isotopomers of 7,10-(OH) 2 -18:1 and 7(S),10(S)-dihydroxyoctadecanoic acid (7,10-(OH) 2 -18:0), and MS analysis to study the mechanism of fragmentation.…”

mentioning

confidence: 99%

Liquid chromatography/tandem mass spectrometric analysis of 7,10-dihydroxyoctadecenoic acid, its isotopomers, and other 7,10-dihydroxy fatty acids formed byPseudomonas aeruginosa42A2

Nilsson

Martínez

Manresa

et al. 2010

Rapid Commun. Mass Spectrom.

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Pseudomonas aeruginosa is an opportunistic pathogen, which oxidizes oleic acid to 7(S),10(S)-dihydroxy-8(E)-octadecenoic acid (7,10-(OH)(2)-18:1) of biological and industrial interest. Electrospray tandem mass spectrometric (MS/MS) analysis of hydroxylated fatty acids usually generates characteristic fragments containing the carboxylate anion and formed by alpha-cleavage at the oxidized carbon. These fragments indicate the positions of the hydroxyl group. In contrast, liquid chromatography (LC)/MS/MS analysis of 7,10-(OH)(2)-18:1 yielded a series of other ions with structural information. To study the fragmentation mechanism, we prepared (2)H- and (18)O-labeled isotopomers. We also performed MS(3) analysis of the major ions, and for comparison we generated the corresponding 7,10-dihydroxy metabolites of 16:1n-7, 18:2n-6, and 20:1n-11 with a protein extract of P. aeruginosa. The MS/MS spectra of 7,10-(OH)(2)-18:1 and its isotopomers, 7,10-(OH)(2)-16:1, and 7,10-(OH)(2)-20:1, contained a series of prominent fragments that all hold the omega end. The 8,9-double bond was not essential for this fragmentation, as 7,10-(OH)(2)-18:0, and its isotopomers, formed essentially the same fragments in the lower mass range. In contrast, 7,10-dihydroxy-8(E),12(Z)-octadecadienoic acid (7,10-(OH)(2)-18:2) fragmented by alpha-cleavage at the oxidized carbons with formation of carboxylate anions. Our results demonstrate that C(16)-C(20) fatty acids with a 7,10-dihydroxy-8(E) functionality undergo charge-driven fragmentation after charge migration to the omega-end, whereas the main ions of 7,10-(HO)(2)-18:2 retain charge at the carboxyl group.

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“…A number of microbial systems that convert oleic acid to monohydroxy and dihydroxy fatty acids have been found (1,2,6,10,14,15,27). Bioconversion of polyunsaturated fatty acids, such as linoleic acid and ␣-and ␥-linolenic acids, has also been studied (10,22,28,30).…”

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confidence: 99%

Production of Novel Tetrahydroxyfuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2

Hosokawa¹,

Hou²,

Weisleder

2003

Appl Environ Microbiol

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Previously, it was reported that a newly isolated microbial culture, Clavibacter sp. strain ALA2, produced trihydroxy unsaturated fatty acids, diepxoy bicyclic fatty acids, and tetrahydroxyfuranyl fatty acids ( ). In this study, we found that Clavibacter sp. strain ALA2 produced novel THFAs, including 13,16-dihydroxy-12-THFA, 15-epoxy-9(Z)-octadecenoic acid (13,16-dihydroxy-THFA), and 7,13,16-trihydroxy-12, 15-epoxy-9(Z)-octadecenoic acid (7,13,16-trihydroxy-THFA), from ␣-linolenic acid (9,12,15-octadecatrienoic acid). The chemical structures of these products were determined by gas chromatography-mass spectrometry and proton and 13 C nuclear magnetic resonance analyses. The optimum incubation temperature was 30°C for production of both hydroxyTHFAs. 13,16-Dihydroxy-THFA was detected after 2 days of incubation, and the concentration reached 45 mg/50 ml after 7 days of incubation; 7,13,16-trihydroxy-THFA was not detected after 2 days of incubation, but the concentration reached 9 mg/50 ml after 7 days of incubation. The total yield of both 13,16-dihydroxy-THFA and 7,13,16-trihydroxy-THFA was 67% (wt/wt) after 7 days of incubation at 30°C and 200 rpm. In previous studies, it was reported that Clavibacter sp. strain ALA2 oxidized the C-7, C-12, C-13, C-16, and C-17 positions of linoleic acid (n-6) into hydroxy groups. In this case, the bond between the C-16 and C-17 carbon atoms is saturated. In ␣-linolenic acid (n-3), however, the bond between the C-16 and C-17 carbon atoms is unsaturated. It seems that enzymes of strain ALA2 oxidized the C-12-C-13 and C-16-C-17 double bonds into dihydroxy groups first and then converted them to hydroxy-THFAs.

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A novel compound, 7,10‐dihydroxy‐8(E)‐octadecenoic acid from oleic acid by bioconversion

Cited by 80 publications

References 9 publications

Biochemical Characterization of the Oxygenation of Unsaturated Fatty Acids by the Dioxygenase and Hydroperoxide Isomerase of Pseudomonas aeruginosa 42A2

Biochemical Characterization of the Oxygenation of Unsaturated Fatty Acids by the Dioxygenase and Hydroperoxide Isomerase of Pseudomonas aeruginosa 42A2

Liquid chromatography/tandem mass spectrometric analysis of 7,10-dihydroxyoctadecenoic acid, its isotopomers, and other 7,10-dihydroxy fatty acids formed byPseudomonas aeruginosa42A2

Production of Novel Tetrahydroxyfuranyl Fatty Acids from α-Linolenic Acid by Clavibacter sp. Strain ALA2

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