Characterization of Hydroperoxides and Carbonyl Compounds Obtained by Lipoxygenase Extracts of Selected Microorganisms

Bisakowski, Barbara; Perraud, Xavier; Kermasha, Sélim

doi:10.1271/bbb.61.1262

Cited by 34 publications

(39 citation statements)

References 27 publications

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“…The characterization of the hydroperoxides formed shows the presence of the different isomers, i.e., 9-, 10-, 12-, 13-hydroperoxide of linoleic acid. 23 The presence of hexanal, dienals, and 1-octen-ol-3 among the volatile compounds isolated from this culture media or from Czapeck-modified medium, 24 strongly suggests the presence of a lipoxygenase activity in Penicillium roqueforti, more particularly, a 10-lipoxygenase activity comparable to that isolated from mushroom. 25 It was shown that this mushroom lipoxygenase catalyzes in a (S)-stereospecific mode, while the stereospecificity of microorganisms lipoxygenase action has not been determined until now.…”

Section: Determination Of Enantiomeric Compositionmentioning

confidence: 76%

Enantiodifferentiation of four ?-lactones produced byPenicillium Roqueforti

Chalier

Crouzet

1998

Chirality

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Section: Determination Of Enantiomeric Compositionmentioning

confidence: 76%

Enantiodifferentiation of four ?-lactones produced byPenicillium Roqueforti

Chalier

Crouzet

1998

Chirality

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“…The HPODs, HPOTs and HPETEs, obtained from the enzymatic oxidation of the selected PUFA substrates were reduced to hydroxides of octadecenoic acid (HODs), octatrienoic acid (HOTs) and eicosatetraenoic acid (HETEs), respectively, using NaBH 4 according to the procedure outlined by Bisakowski et al 8 The hydroxide regio-isomers were separated by HPLC using a Beckman Gold system (Beckman Instruments, Fullerton, CA) and an alphabond silica column (300 × 3.9 mm i.d., 5 µm; Alltech Associates Inc., Deerfield, IL), using an ultra-violet diode array detector (UV-DAD) (Beckman, Model 168) and an evaporative laser light scattering detector (LLSD) (Varex Corporation, Burtonsville, MD) according to the procedure reported by Perraud and Kermasha. 15 Portions of the hydroxides were collected and subjected to chiral phase HPLC (CP-HPLC) and to gas-liquid chromatography-mass spectrometry (GC-MS) analyses.…”

Section: High-performance Liquid Chromatography Of Hydroperoxide End mentioning

confidence: 99%

“…The HODs and HOTs were derivatized into their corresponding methyl trimethylsilyloxystearate (MTMS stearate) derivatives, whereas the HETEs were derivatized into their methyl trimethylsilyloxyarachidate (MTMS arachidate) derivatives, according to the method described by Bisakowski et al 8 The derivatized hydroxides were analysed using an HP 6890 Series GC System (HewlettPackard Co., Palo Alto, CA), with computerized integration and data handling, and a 5973 Mass Selective Detector (Hewlett-Packard), as outlined by Perraud and Kermasha. 15 Manual tuning of the mass spectrometer was accomplished with the use of perfluorotributylamine (PFTBA) calibrant, while selecting ion m/z ratios of 100, 264, and 414 for improved resolution.…”

Section: Gas-liquid Chromatography-mass Spectrometry Of Hydroperoxidementioning

confidence: 99%

“…The m/z ratios of 9-(m/z 229 and 259), 10-(m/z 215 and 273), 12-(m/z 187 and 301) and 13-MTMS (m/z 173 and 315), were consistent with the fragmentation of the four regio-isomeric HODs. 8,15 The LOX from P. candidum was determined to produce mostly unconjugated 9-and 13-HPODs, with 66% of total isomers produced. Other microbial LOX activity was determined to produce exclusively 13-and 9-HPOD when linoleic acid was used as substrate, including those of T. vulgaris 2 and G. candidum.…”

Section: Np-hplc and Gc-ms Of Lox End Productsmentioning

confidence: 99%

“…7 The regio-isomeric hydroperoxides can be derived from linoleic acid (octadecadienoic acid hydroperoxides, HPODs), linolenic acid (octadecatrienoic hydroperoxides, HPOTs), and arachidonic (eicosatetraenoic acid hydroperoxides, HPETEs), which have been considered flavour precursors, acting as substrates for subsequent enzymatic activities. 8,9 One such activity is that of hydroperoxide lyase (HPL), reported to cleave the hydroperoxide, producing a volatile compound such as an alcohol. 10 Selected moulds reported to possess LOX activity include Fusarium spp., [11][12][13] Geotrichum spp., 14 Penicillium spp.…”

Section: Introductionmentioning

confidence: 99%

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Production of flavour precursors byPenicilliumcandidum using selected polyunsaturated fatty acids

Hall

Husson²,

Kermasha

2005

Flavour Fragr. J.

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Biomass of Penicillium candidum was harvested and homogenized prior to centrifugation. The resultant supernatant, considered as the crude enzymatic extract, was enriched by ammonium sulphate precipitation. The enriched enzymatic extract was assayed for its lipoxygenase (LOX) activity, using selected polyunsaturated fatty acids (PUFAs) as substrates. Two pH optima for LOX activity were determined at 6.0 and 8.5. The results indicated a wide range of LOX activity towards free PUFAs, including linoleic, linolenic and arachidonic acids, as well as preferential substrate specificity towards linoleic acid over its alkyl esters. The catalytic efficiency values, defined as the ratio V max :K m , were 214, 163 and 160 for linolenic, linoleic and arachidonic acids, respectively. It was shown that the LOX activity produced many monohydroperoxy regio-isomers of the PUFAs, and there was a predominance of conjugated diene hydroperoxides. Significant production (16%) of the unconjugated 10-hydroperoxides of octadecadienoic acid (HPOD) and octadecatrienoic acid (HPOT) was also obtained by the enriched LOX activity. Four major hydroperoxy-eicosatetraenoic acid (HPETE) regioisomers, including the 8-, 9-, 12-and 15-HPETEs, were obtained from the bioconversion of arachidonic acid. Chiral studies of end products indicated varying degrees of enantio-selectivity, producing excesses in favour of the (S) stereo-isomer, for the hydroperoxide end-products resulted from the bioconversion of linoleic, linolenic and arachidonic acids.

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Anaerobic lipoxygenase activity fromChlorella pyrenoidosa responsible for the cleavage of the 13-hydroperoxides of linoleic and linolenic acids

Núñez¹,

Foglia

Savary

et al. 2000

Eur. J. Lipid Sci. Technol.

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An enzyme from the alga Chlorella pyrenoidosa, previously identified as a hydroperoxide lyase (HPLS), cleaves the 13‐hydroperoxide derivatives of linoleic and linolenic acids into a volatile C5 fragment and a C13 oxo‐product, 13‐oxo‐9(Z),11(E)tridecadienoic acid (13‐OTA). Gas chromatography/mass spectrometry (GC/MS) headspace analysis of the volatile products indicated the formation of pentane when the substrate was the 13‐hydroperoxide derivative of linoleic acid, whereas a more complex mixture of hydrocarbons was formed when the 13‐hydroperoxide derivative of linolenic acid was the substrate. Analysis of the nonvolatile products by GC/MS and liquid chromatography/mass spectrometry (LC/MS) indicated the formation of 13‐OTA along with the 13‐ketone derivative. This enzymatic activity was inhibited by oxygen but was restored with nitrogen. The enzymatic cleavage activity was coincidental in purified fractions with lipoxygenase activity that produced the 13‐ and 9‐hydroperoxide derivatives of linolenic acid. The results suggest that the enzymatic cleavage activity in Chlorella pyrenoidosa was not a consequence of hydroperoxide lyase activity as previously thought, but was due to anaerobic lipoxygenase activity. This enzyme fraction was purified by (NH4)2 SO4 precipitation, gel filtration, and hydrophobic interaction chromatography. The purified enzyme has an approximate MW of 120 KDa and maximum activity at pH 8.0.

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Characterization of Hydroperoxides and Carbonyl Compounds Obtained by Lipoxygenase Extracts of Selected Microorganisms

Cited by 34 publications

References 27 publications

Enantiodifferentiation of four ?-lactones produced byPenicillium Roqueforti

Enantiodifferentiation of four ?-lactones produced byPenicillium Roqueforti

Production of flavour precursors byPenicilliumcandidum using selected polyunsaturated fatty acids

Anaerobic lipoxygenase activity fromChlorella pyrenoidosa responsible for the cleavage of the 13-hydroperoxides of linoleic and linolenic acids

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