Metabolic profiling of oxylipins in germinating cucumber seedlings - lipoxygenase-dependent degradation of triacylglycerols and biosynthesis of volatile aldehydes

Weichert, Heiko; Kolbe, A.; Kraus, A.; Wasternack, Claus; Feußner, Ivo

doi:10.1007/s00425-002-0779-4

Cited by 48 publications

(33 citation statements)

References 32 publications

(35 reference statements)

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“…6). The enzymatic production of reactive aldehydes via the hydroperoxide lyase pathway is closely associated with chloroplast envelopes (Froehlich et al 2001) and lipid bodies (Weichert et al 2002). Under environmental stresses, the nonenzymatic production of reactive aldehydes would occur in a wider range of compartments.…”

Section: Discussionmentioning

confidence: 99%

The NADPH:Quinone Oxidoreductase P1-ζ-crystallin in Arabidopsis Catalyzes the α,β-Hydrogenation of 2-Alkenals: Detoxication of the Lipid Peroxide-Derived Reactive Aldehydes

Mano

Torii²,

Hayashi³

et al. 2002

Plant and Cell Physiology

135

118

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; P1-z-crystallin (P1-ZCr) is an oxidative stress-induced NADPH:quinone oxidoreductase in Arabidopsis thaliana, but its physiological electron acceptors have not been identified. We found that recombinant P1-ZCr catalyzed the reduction of 2-alkenals of carbon chain C 3 -C 9 with NADPH. Among these 2-alkenals, the highest specificity was observed for 4-hydroxy-(2E)-nonenal (HNE), one of the major toxic products generated from lipid peroxides. (3Z)-Hexenal and aldehydes without a,b -unsaturated bonds did not serve as electron acceptors. In the 2-alkenal molecules, P1-ZCr catalyzed the hydrogenation of a,b -unsaturated bonds, but not the reduction of the aldehyde moiety, to produce saturated aldehydes, as determined by gas chromatography/mass spectrometry. We propose the enzyme name NADPH:2-alkenal a,b -hydrogenase (ALH). A major portion of the NADPH-dependent HNE-reducing activity in A. thaliana leaves was inhibited by the specific antiserum against P1-ZCr, indicating that the endogenous P1-ZCr protein has ALH activity. Because expression of the P1-ZCr gene in A. thaliana is induced by oxidative stress treatments, we conclude that P1-ZCr functions as a defense against oxidative stress by scavenging the highly toxic, lipid peroxide-derived a,b -unsaturated aldehydes.

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Section: Discussionmentioning

confidence: 99%

The NADPH:Quinone Oxidoreductase P1-ζ-crystallin in Arabidopsis Catalyzes the α,β-Hydrogenation of 2-Alkenals: Detoxication of the Lipid Peroxide-Derived Reactive Aldehydes

Mano

Torii²,

Hayashi³

et al. 2002

Plant and Cell Physiology

135

118

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“…These types of lipid transformations are frequently associated with oxylipin metabolism in plants, which involves the production of various lipophilic hormone-like molecules associated with plant stress response and innate immunity ( 65 ). Alternatively, caleosins have been implicated in the degradation of polyunsaturated fatty acids, as the products of peroxidized linoleic acid can accumulate to high levels in germinated seeds, and these products can subsequently be broken down by ␤ -oxidation in glyoxysomes ( 66,67 ). Additional support for a role of caleosins in oil breakdown comes from the analysis of gene knockout mutants in Arabidopsis , where disruption of the major seed-expressed caleosin resulted in a decreased rate of fatty acid degradation ( 68 ).…”

Section: Steroleosinsmentioning

confidence: 99%

Biogenesis and functions of lipid droplets in plants

Chapman

Dyer

Mullen

2012

Journal of Lipid Research

327

162

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Journal of Lipid Research Volume 53, 2012 215developing seeds and other plant tissues that contribute to the synthesis of TAGs, although the relative contributions of these alternative pathways to TAG accumulation may vary depending on the tissue and/or species ( 1 ).There also has been a growing appreciation in the past few years that the compartmentation of neutral lipids in LDs of plants extends well beyond their role as simply static depots for carbon storage in seeds and, consequently, there is renewed interest in the cellular ontogeny and dynamics of this organelle. For instance, LDs are observed in nearly all cell types in plants, and although the biogenesis of LDs in nonseed tissues is still poorly understood, we now know that they are involved in many unique processes, such as stress response, pathogen resistance, and hormone metabolism. Furthermore, there are highly specialized roles for LDs in anther development, wherein LDs contribute signifi cantly to the formation of the hydrophobic barrier of the pollen coat as tapetal tissues undergo programmed cell death. Interestingly, this process is somewhat similar to the specialized role that LDs play in the formation of the hydrophobic barrier that comprises the outer layer of mammalian skin.Overall, knowledge of LD function in both seed and nonseed tissues has been greatly enhanced by efforts to characterize the major proteins that specifi cally associate with these organelles, namely oleosins, caleosins, and sterol dehydrogenases (steroleosins) ( Fig. 1 ). Here, after a brief description of LD biogenesis in plant cells, we review the functional properties of these major LD-associated proteins and discuss how they compare with the properties of their known or potential counterparts in yeasts and mammals. We also describe the specialized role of LDs in pollen coat formation and how this process has some The seeds of plants store signifi cant amounts of neutral lipids, namely triacylglycerols (TAGs), in cytosolic lipid droplets (LDs), most of which are subsequently mobilized immediately after germination in order to fuel the growth and development of the seedling prior to photosynthetic establishment. In developing seeds, TAGs are assembled in the endoplasmic reticulum (ER) from acyl-CoAs and glycerol by the conserved "Kennedy" pathway that operates in all eukaryotes. Recently, however, additional acylCoA-independent reactions have been identifi ed in

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“…This enzyme, which is expressed during the early stages of germination associates with lipid-body membranes and catalyzes stereospecific oxygenation of the linoleate moieties of TAGs to (9Z,11E,13S)-13-hydroperoxy-octadeca-9,11-dienoic acid (13-HPODE; Feussner et al 1998a). In addition, an enzyme activity responsible for the specific release of these oxygenated fatty acid residues from the TAGs has been characterized (Balkenhohl et al 1998), and large amounts of free (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid (13-HODE) have been demonstrated to occur in the cytosolic extract from cucumber cotyledons (Weichert et al 2002).…”

Section: Introductionmentioning

confidence: 99%

Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and ?-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes

Gerhardt

Fischer

Balkenhohl

et al. 2004

Planta

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During the early stages of germination, a lipid-body lipoxygenase is expressed in the cotyledons of sunflowers (Helianthus annuus L.). In order to obtain evidence for the in vivo activity of this enzyme during germination, we analyzed the lipoxygenase-dependent metabolism of polyunsaturated fatty acids esterified in the storage lipids. For this purpose, lipid bodies were isolated from etiolated sunflower cotyledons at different stages of germination, and the storage triacylglycerols were analyzed for oxygenated derivatives. During the time course of germination the amount of oxygenated storage lipids was strongly augmented, and we detected triacylglycerols containing one, two or three residues of (9Z,11E,13S)-13-hydro(pero)xy-octadeca-9,11-dienoic acid. Glyoxysomes from etiolated sunflower cotyledons converted (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid to (9Z,11E)-13-oxo-octadeca-9,11-dienoic acid via an NADH-dependent dehydrogenase reaction. Both oxygenated fatty acid derivatives were activated to the corresponding CoA esters and subsequently metabolized to compounds of shorter chain length. Cofactor requirement and formation of acetyl-CoA indicate degradation via beta-oxidation. However, beta-oxidation only proceeded for two consecutive cycles, leading to accumulation of a medium-chain metabolite carrying an oxo group at C-9, equivalent to C-13 of the parent (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid. Short-chain beta-oxidation intermediates were not detected during incubation. Similar results were obtained when 13-hydroxy octadecanoic acid was used as beta-oxidation substrate. On the other hand, the degradation of (9Z,11E)-octadeca-9,11-dienoic acid was accompanied by the appearance of short-chain beta-oxidation intermediates in the reaction mixture. The results suggest that the hydroxyl/oxo group at C-13 of lipoxygenase-derived fatty acids forms a barrier to continuous beta-oxidation by glyoxysomes.

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Metabolic profiling of oxylipins in germinating cucumber seedlings - lipoxygenase-dependent degradation of triacylglycerols and biosynthesis of volatile aldehydes

Cited by 48 publications

References 32 publications

The NADPH:Quinone Oxidoreductase P1-ζ-crystallin in Arabidopsis Catalyzes the α,β-Hydrogenation of 2-Alkenals: Detoxication of the Lipid Peroxide-Derived Reactive Aldehydes

The NADPH:Quinone Oxidoreductase P1-ζ-crystallin in Arabidopsis Catalyzes the α,β-Hydrogenation of 2-Alkenals: Detoxication of the Lipid Peroxide-Derived Reactive Aldehydes

Biogenesis and functions of lipid droplets in plants

Lipoxygenase-mediated metabolism of storage lipids in germinating sunflower cotyledons and ?-oxidation of (9Z,11E,13S)-13-hydroxy-octadeca-9,11-dienoic acid by the cotyledonary glyoxysomes

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