15(R)-hydroxylinoleic acid, an oxylipin from oat seeds

Hámberg, Mats; Hamberg, Gunvor

doi:10.1016/0031-9422(96)00059-3

Cited by 26 publications

(29 citation statements)

References 16 publications

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“…2, Panel B4) (Hamberg and Hamberg, 1996). It is possible that a FAD3-like gene may exhibit, in addition to its dominant D15-desaturation activity, low levels of a-linolenate 15,16-epoxidase activity and/or linoleate 15-hydroxylase activity.…”

Section: Fatty Acid and Lipid Accumulation In C Sativa Seeds During mentioning

confidence: 96%

Lipid analysis of developing Camelina sativa seeds and cultured embryos

2015

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Camelina sativa is a cultivated oilseed rich in triacylglycerols containing oleic, linoleic, α-linolenic and eicosenoic acids. As it holds promise as a model species, its lipid synthesis was characterized in vivo and in culture. Lipid accumulates at a maximum rate of about 26 μg/day/seed (11.5 mg lipid/day/g fresh seed weight), a rate comparable with other oilseeds. Noteworthy is a late stage surge in α-linolenic acid accumulation. Small amounts of unusual epoxy and hydroxy fatty acids are also present in the triacylglycerols. These include 15,16-epoxy- and 15-hydroxy-octadecadienoic acids and homologous series of ω7-hydroxy-alk-ω9-enoic and ω9/10-hydroxy-alkanoic acids. Mid-maturation embryos cultured in vitro have growth and lipid deposition rates and fatty acid compositions that closely match that of seeds, but extended culture periods allow these rates to rise and surpass those observed in planta. Optimized thin layer chromatography systems for characterization of labeled products from acetate or glycerol labeling are described. Glycerol label is only found in acylglycerols, largely as the intact glyceryl backbone, but acetate can label acyl groups and sterols, the latter to a much higher relative specific activity. This presumably occurs because mevalonic acid precursor is derived from the non-plastid pool of acetyl-CoA that is also the source for malonyl-CoA to drive FAE1-dependent chain elongation. Particular attention has been paid to the separation of sterols and diacylglycerols, and to hydrogenation of triacylglycerols to simplify their analysis. These improved methods will allow more accurate analyses of the fluxes of lipid metabolism in cultured plant embryos.

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Section: Fatty Acid and Lipid Accumulation In C Sativa Seeds During mentioning

confidence: 96%

Lipid analysis of developing Camelina sativa seeds and cultured embryos

2015

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“…An additional oxygenated fatty acid, 15 hydroxy-9,12-octadecadienoic acid (avenoleic acid) is readily detectable in crude lipid extracts by GC-MS, with characteristic fragments of m/z 73 [TMSi + ], m/z 145 [TMSiO-CH-(CH 2 ) 2 -CH 3 ] + , m/z 310 [M-OHC-(CH 2 ) 2 -CH 3 ] + , and m/z 367 [M-CH 3 ] + (Hamberg and Hamberg 1996b). An additional oxygenated fatty acid, 15 hydroxy-9,12-octadecadienoic acid (avenoleic acid) is readily detectable in crude lipid extracts by GC-MS, with characteristic fragments of m/z 73 [TMSi + ], m/z 145 [TMSiO-CH-(CH 2 ) 2 -CH 3 ] + , m/z 310 [M-OHC-(CH 2 ) 2 -CH 3 ] + , and m/z 367 [M-CH 3 ] + (Hamberg and Hamberg 1996b).…”

Section: Resultsmentioning

confidence: 99%

Accumulation of Oxygenated Fatty Acids in Oat Lipids During Storage

2010

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Cereal Chem. 87(6):532-537Oxygenated fatty acids were identified in oat grain by gas chromatography-mass spectrometry. We hypothesized that most of these were the results of lipoxygenase activity. This hypothesis was tested by measuring concentrations of these compounds after hydrothermal treatments and storage of oat groats or oat flour for 22 weeks at 37°C and 65% relative humidity. Steam treatments inactivated lipases, whereas roasting at 106°C did not. Free fatty acids accumulated quickly in untreated or roasted flour, but not in steamed flour or groats. A total of six hydroxy and epoxy fatty acids were identified. Oxidized fatty acids were found in both esterified lipids and free fatty acids, indicating that lipase action was not necessary for lipid oxidation. More oxidation products were found in flour than in groats, and less were found in the steamed treatments. Lipoperoxygenase appeared to be involved in the formation of oxidation products, although nonenzymatic mechanisms may also operate. Hydroxy-fatty acids are associated with strongly bitter flavors and are undesirable. Results indicate the importance of enzyme inactivation before storage of processed oat products.

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“…Phenolic compounds are oxidized to toxic deriva tives (quinones). Compounds having ortho-hy droxyl groups, including catechol resorcinol deriv atives (Hamberg and Hamberg, 1996) and others are detrimental to greenbug growth and progeny survival; however, the role o f these com pounds in plants is not clear. Most o f them are thought to affect plant growth regulation (Corcuera, 1993).…”

Section: Ni Plants (4) Appeared In Methanol Extracts and In Epicuticmentioning

confidence: 99%

“…Several hydroxylated and high unsaturated deriva tives of linoleic acid, isolated from rice have been implicated as defensive substance against attack by plant pathogens; for example, a new oxylipin 15(/? )-hydroxy-9(Z), 12(Z)-octadecadienoic acid has also been isolated from oat seeds (Hamberg and Hamberg, 1996). The amount found in seeds of barley and wheat, however was less than 1 |ig/g fresh weight.…”

Section: Introductionmentioning

confidence: 98%

Chemical Constituents from Shoots of Hordeum vulgare Infested by the Aphid Schizaphis graminum

Muñoz

Argandoña

Corcuerac

1998

Zeitschrift Für Naturforschung C

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Stress, pathogens or insects induce profound changes in the expression of the chemical constituents of plants. Some of these changes could be adaptations to the new conditions or the expression of new defensive characteristics. The purpose of this paper was to analyze the effect of aphid infestation on the composition of endogenous compound, in barley leaves. Leaf waxes were obtained by washing with dichloromethane and remaining compounds were extracted with ethyl acetate and ethanol from homogenized leaves. The identification of compounds was done by combined capillary gas chromatography and mass spectrometry. Epicuticular compounds detected in barley after 6 days of aphid infestation were as follows (%): (1) 1-docosene (1.98), (2) 1-octadecene (2.07), (3) phytol (0.81). Epicuticular compounds in non-infested plants were (4) isophytol (0.83), (5) N-cyclohexyl-cyclohexanamine, (0.11) (6) 5-pentadecyl-1,3-benzenediol (2.10). In ethyl acetate extracts from infested plants the main compounds were: (1) (2.02), (7) 2,5-diethylpyrazine (0.61), (8) (5E)-eicosene (1.61), (9) (3E)-eicosene (1.93), (10) (9E)-eicosene (1.80). In non-infested plants the only detected compounds were (1) (1.02), (6) (1.91), and (7) (0.43). In methanol extracts from infested plants the following compounds were identified: (6) (2.15), (7) (0.21), (11) 2,2,6.6 tetramethyl- piperidine (0.12), (12) indole (1.01), (13) heptadecane (0.10), (14) methyl-β-ᴅ-glucopyranoside (0.21), (15) 2,5- dihydroxybenzaldehyde (0.27) and (16) N-phenyl-2-naphthalenamine (0.29). In polar extracts from non-infested plants the most abundant compounds were (4) (1.40), (7) (0.18), (17) (9Z,12Z,15Z)-octadecatrienoic methyl ester (1.01), (18) (9Z,15Z)- octadienoic methyl ester (2.01), and (19) hexadecanoic methyl ester (1.93). Compounds 4, 5 and 7 -1 9 are described for the first time in Hordeum vulgare.

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15(R)-hydroxylinoleic acid, an oxylipin from oat seeds

Cited by 26 publications

References 16 publications

Lipid analysis of developing Camelina sativa seeds and cultured embryos

Lipid analysis of developing Camelina sativa seeds and cultured embryos

Accumulation of Oxygenated Fatty Acids in Oat Lipids During Storage

Chemical Constituents from Shoots of Hordeum vulgare Infested by the Aphid Schizaphis graminum

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