Enzymatic oxidations of linoleic acid and glycerol‐1‐monolinoleate in doughs and flour‐water suspensions

Graveland, A.

doi:10.1007/bf02639001

Cited by 147 publications

(50 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Formation of hydroxyoctadecadienoic acids and epoxyhydroxyoctadecenoic acids upon incubation of linoleic acid with wheat (Triticum aestivum) flour-water suspensions was described by Graveland (1970). In the same year, the presence of a "lipoperoxidase" activity in oat (Avena sntiva) seed was postulated to explain reduction of linoleic acid 9-and 13-hydroperoxides (9-HPOD and 13-HPOD) into the corresponding alcohols (9-and 13-HOD) (Heimann and Schreier, 1970).…”

Section: Dihydroxy-9(z)-octadecenoic Acid and 12(r)13(s)-epoxy-9(s)mentioning

confidence: 99%

“…lncubation of linoleic acid with the 105,OOOg particle fraction gave a similar, but not identical, pattern of metabolites. Conversion of linoleic acid into 9(S),12(S),13(S)-trihydroxy-1 O(€)-octadecenoic acid, a naturally occurring oxylipin with antifungal properties, took place by a pathway involving sequential catalysis by lipoxygenase, peroxygenase, and epoxide hydrolase.Formation of hydroxyoctadecadienoic acids and epoxyhydroxyoctadecenoic acids upon incubation of linoleic acid with wheat (Triticum aestivum) flour-water suspensions was described by Graveland (1970). In the same year, the presence of a "lipoperoxidase" activity in oat (Avena sntiva) seed was postulated to explain reduction of linoleic acid 9-and 13-hydroperoxides (9-HPOD and 13-HPOD) into the corresponding alcohols (9-and 13-HOD) (Heimann and Schreier, 1970).…”

mentioning

confidence: 99%

“…Regioisomeric 9,10,13-and 9,12,13-trihydroxyoctadecenoic acids, hydrolysis products of epoxy-hydroxyoctadecenoic acids, have also been isolated following incubation of linoleic acid and linoleic acid hydroperoxides with preparations of cereal seeds (Graveland, 1970;Esterbauer and Schauenstein, 1977). Epoxyhydroxyoctadecenoic acids have been reported to be formed from linoleic acid hydroperoxides mainly by an intermolecular reaction (Heimann and Klaiber, 1977); however, the exact mechanism of epoxy-hydroxy acid biosynthesis in cereal seeds is not known.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Peroxygenase-Catalyzed Fatty Acid Epoxidation in Cereal Seeds (Sequential Oxidation of Linoleic Acid into 9(S),12(S),13(S)-Trihydroxy-10(E)-Octadecenoic Acid)

Hámberg

Hamberg

1996

Plant Physiol.

View full text Add to dashboard Cite

Peroxygenase-catalyzed epoxidation of oleic acid in preparations of cereal seeds was investigated. The 105,OOOg particle fraction of oat (Avena safiva) seed homogenate showed high peroxygenase activity, i.e. 3034 2 288 and 2441 f 168 nmol (10 min)-' mg-' protein in two cultivars, whereas the corresponding fraction obtained from barley (Hordeum vulgare and Hordeum distichum), rye (Secale cereale), and wheat (Trificum aesfivum) showed only weak activity, i.e. dihydroxy-9(Z)-octadecenoic acid, and 12(R),13(S)-epoxy-9(S)-hy-droxy-1 O(€)-octadecenoic acid. lncubation of linoleic acid with the 105,OOOg particle fraction gave a similar, but not identical, pattern of metabolites. Conversion of linoleic acid into 9(S),12(S),13(S)-trihydroxy-1 O(€)-octadecenoic acid, a naturally occurring oxylipin with antifungal properties, took place by a pathway involving sequential catalysis by lipoxygenase, peroxygenase, and epoxide hydrolase.Formation of hydroxyoctadecadienoic acids and epoxyhydroxyoctadecenoic acids upon incubation of linoleic acid with wheat (Triticum aestivum) flour-water suspensions was described by Graveland (1970). In the same year, the presence of a "lipoperoxidase" activity in oat (Avena sntiva) seed was postulated to explain reduction of linoleic acid 9-and 13-hydroperoxides (9-HPOD and 13-HPOD) into the corresponding alcohols (9-and 13-HOD) (Heimann and Schreier, 1970). In a further study, oat seed was reported to '

show abstract

Section: Dihydroxy-9(z)-octadecenoic Acid and 12(r)13(s)-epoxy-9(s)mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Peroxygenase-Catalyzed Fatty Acid Epoxidation in Cereal Seeds (Sequential Oxidation of Linoleic Acid into 9(S),12(S),13(S)-Trihydroxy-10(E)-Octadecenoic Acid)

Hámberg

Hamberg

1996

Plant Physiol.

View full text Add to dashboard Cite

show abstract

“…Thus, for instance, lipid extracts of homogenized tissue samples are subjected to hydrogenation, 12,13 then the acidic groups are converted by treatment with diazomethane to methyl esters. 13 Subsequently the hydroxy fatty acid methyl esters are enriched by silica-gel column chromatography.…”

Section: Introductionmentioning

confidence: 99%

Linoleic acid peroxidation products are metabolized by hydrogenation in porcine liver tissue

Hecht¹,

Spiteller²

1998

Eur. J. Mass Spectrom.

View full text Add to dashboard Cite

Homogenization of mammalian tissue activates enzymes which cause degradation. This effect was used to elucidate the metabolism of 13-S-hydroxy-9,11-octadecadienoic acid (13-S-HODE) and 9-S-hydroxy-10,12-octadecadienoic acid (9-S-HODE), physiologically active products of lipid peroxidation (LPO) processes, by electron ionization GC/MS. 13-S-HODE was added to a porcine liver homogenate, samples withdrawn at timed intervals and extracts of polar fatty acids then subjected to GC/MS analysis, after methylation and trimethylsilylation, to give mass spectra of derivatised hydroxy acids that showed that degradation starts with the hydrogenation of one double bond. The position of the remaining double bond was determined by reacting the hydroxyoctadecenoic acid thus obtained with osmium tetroxide to give a trihydroxystearic acid. After appropriate derivatization (methylation, trimethylsilylation), the mass spectrum unambiguously demonstrated the presence of a 9,10,13-trihydroxystearic acid derivative and hence the double bond in the precursor molecule is located in position 9. Enzymatic hydrogenation of 13-S-HODE is enhanced by the addition of NADH and, to an even greater extent, by NADPH. Similarly, 9-S-HODE is metabolized to 9-S-hydroxy-12-octadecenoic acid.

show abstract

“…As with cis-epoxy type, methyl trans-9,10-epoxyoctadecanoate was prepard from methyl eladiate. Methyl a-hydroxyoleate (methyl a-hydroxyoctadecenoate) was prepared by the reduction of methyl ahydroperoxyoleate depending on sodium borohydride 9) . This compound, a-methyl hydroxyoleate, is a mixture of four positional isomers same as methyl a-hydroperoxyoleates.…”

mentioning

confidence: 99%

Effect of the Amount of Liquid Phase in Packed Column GC on Air Oxidation Product of Methyl Oleate

Mochida

Oka

Sugawara³

et al. 2009

J. Oleo Sci.

View full text Add to dashboard Cite

The analysis or preparative isolation of a specimen by a packed column gas chromatograph is affected by the kind and amount (concentration) of the liquid phase coated on the stationary phase. In particular, compounds having the same or similar molecular weight and similar functional groups are largely affected. Methyl oleate, which is a typical component of fats and oils, produces hydroperoxide by air oxidation as a first step. After that, various oxygenated compounds with a carbon number of 19 are produced. In this study, the effect of the concentration of ethylene glycol succinate polyester (EGS) as the liquid phase was examined for these compounds. The retention time of the hydroxides increased with an increase in the EGS concentration. The effect of the EGS concentration on the retention time decreased when these compounds were trimethyl silylated (TMS). The retention time of epoxides and oxo compounds increased with an increase in the EGS concentration independently of trimethyl silylation. Correction values were required for all quantitation.

show abstract

Enzymatic oxidations of linoleic acid and glycerol‐1‐monolinoleate in doughs and flour‐water suspensions

Cited by 147 publications

References 19 publications

Peroxygenase-Catalyzed Fatty Acid Epoxidation in Cereal Seeds (Sequential Oxidation of Linoleic Acid into 9(S),12(S),13(S)-Trihydroxy-10(E)-Octadecenoic Acid)

Peroxygenase-Catalyzed Fatty Acid Epoxidation in Cereal Seeds (Sequential Oxidation of Linoleic Acid into 9(S),12(S),13(S)-Trihydroxy-10(E)-Octadecenoic Acid)

Linoleic acid peroxidation products are metabolized by hydrogenation in porcine liver tissue

Effect of the Amount of Liquid Phase in Packed Column GC on Air Oxidation Product of Methyl Oleate

Contact Info

Product

Resources

About