Oxylipins: Structurally diverse metabolites from fatty acid oxidation

Mosblech, Alina; Feußner, Ivo; Heilmann, Ingo

doi:10.1016/j.plaphy.2008.12.011

Cited by 376 publications

(331 citation statements)

References 119 publications

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“…FAOOHs can to be formed either chemically (e.g. in the presence of free radicals; Mosblech et al, 2009) or enzymatically by the oxygenation of C16 and C18 unsaturated fatty acids catalyzed by 9-and 13-lipoxygenases (9-LOXs and 13-LOXs; Feussner and Wasternack, 2002) or a-dioxygenases (a-DOXs; Hamberg et al, 1999). Thus, the biosynthesis of FAOOHS is well established, but the endogenous enzyme(s) reducing these hydroperoxides to FAOHs remain largely enigmatic.…”

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confidence: 99%

The Reductase Activity of the Arabidopsis Caleosin RESPONSIVE TO DESSICATION20 Mediates Gibberellin-Dependent Flowering Time, Abscisic Acid Sensitivity, and Tolerance to Oxidative Stress

et al. 2014

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Contrasting with the wealth of information available on the multiple roles of jasmonates in plant development and defense, knowledge about the functions and the biosynthesis of hydroxylated oxylipins remains scarce. By expressing the caleosin RESPONSIVE TO DESSICATION20 (RD20) in Saccharomyces cerevisiae, we show that the recombinant protein possesses an unusual peroxygenase activity with restricted specificity toward hydroperoxides of unsaturated fatty acid. Accordingly, Arabidopsis (Arabidopsis thaliana) plants overexpressing RD20 accumulate the product 13-hydroxy-9,11,15-octadecatrienoic acid, a linolenate-derived hydroxide. These plants exhibit elevated levels of reactive oxygen species (ROS) associated with early gibberellin-dependent flowering and abscisic acid hypersensitivity at seed germination. These phenotypes are dependent on the presence of active RD20, since they are abolished in the rd20 null mutant and in lines overexpressing RD20, in which peroxygenase was inactivated by a point mutation of a catalytic histidine residue. RD20 also confers tolerance against stress induced by Paraquat, Rose Bengal, heavy metal, and the synthetic auxins 1-naphthaleneacetic acid and 2,4-dichlorophenoxyacetic acid. Under oxidative stress, 13-hydroxy-9,11,15-octadecatrienoic acid still accumulates in RD20-overexpressing lines, but this lipid oxidation is associated with reduced ROS levels, minor cell death, and delayed floral transition. A model is discussed where the interplay between fatty acid hydroxides generated by RD20 and ROS is counteracted by ethylene during development in unstressed environments.

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confidence: 99%

The Reductase Activity of the Arabidopsis Caleosin RESPONSIVE TO DESSICATION20 Mediates Gibberellin-Dependent Flowering Time, Abscisic Acid Sensitivity, and Tolerance to Oxidative Stress

et al. 2014

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“…지질분해는 methyl jasmonate, cis-jasmone, 및 jasmine lactones등을 생성한다. 이들 향기는 Jasminum grandiflorum 꽃에서 분리한 fragrant volatiles이고 우롱차 및 녹차에서 많이 함유되어 있다 [18]. Methyl jasmonate는 우롱차에서 alpha-linolenic acid에서 분해된 대표적인 향기성분이다.…”

Section: Lipidunclassified

Formation Mechanism of Aroma Compound during Tea Manufacturing Process

조미자¹,

조기정²,

최현숙³

et al. 2016

KSBB Journal

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Tea is an aqueous infusion of dried leaves of the plant Camellia sinensis L. and is the second most widely consumed beverage around the world after water. Aroma compounds of tea differ largely depending on the manufacturing process, even from the same categories of different origins. The flavor of tea can be divided into two categories: taste (non-volatile compounds) and aroma (volatile compounds). In the present study, we review the formation mechanism of main aromas generated from carotenoids, lipids, glycosides as precursors, and Maillard reaction during the tea manufacturing process, with biological and chemical mechanisms.

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“…Oxylipin biosynthesis is initiated by the enzyme lipoxygenase (LOX; EC1.13.11.12), which is ubiquitous in plants and mammals and catalyses the hydroperoxidation of polyunsaturated fatty acids for further conversion into volatile aldehydes and JAs in plants (Mosblech et al, 2009), into diols and lactones in fungi (Tsitsigiannis and Keller, 2007), and into lipoxins and leukotrienes in mammals (Samuelsson et al, 1987;Sigal et al, 1994). In plants, two types of LOX, 13-LOX and 9-LOX, catalyse the formation of two different isomer products, (13S)-and (9S)-hydroperoxyoctadecadienoic acids (13-and 9-HPOD) by introducing molecular oxygen at either carbon atom 13 or carbon atom 9, respectively, of the hydrocarbon backbone (Wasternack, 2007).…”

Section: Introductionmentioning

confidence: 99%

PgLOX6 encoding a lipoxygenase contributes to jasmonic acid biosynthesis and ginsenoside production in Panax ginseng

Rahimi

Kim

Sukweenadhi

et al. 2016

EXBOTJ

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Ginsenosides, the valuable pharmaceutical compounds in Panax ginseng, are triterpene saponins that occur mainly in ginseng plants. It was shown that in vitro treatment with the phytohormone jasmonic acid (JA) is able to increase ginsenoside production in ginseng plants. To understand the molecular link between JA biosynthesis and ginsenoside biosynthesis, we identified a JA biosynthetic 13-lipoxygenase gene (PgLOX6) in P. ginseng that promotes ginsenoside production. The expression of PgLOX6 was high in vascular bundles, which corresponds with expression of ginsenoside biosynthetic genes. Consistent with the role of PgLOX6 in synthesizing JA and promoting ginsenoside synthesis, transgenic plants overexpressing PgLOX6 in Arabidopsis had increased amounts of JA and methyl jasmonate (MJ), increased expression of triterpene biosynthetic genes such as squalene synthase (AtSS1) and squalene epoxidase (AtSE1), and increased squalene content. Moreover, transgenic ginseng roots overexpressing PgLOX6 had around 1.4-fold increased ginsenoside content and upregulation of ginsenoside biosynthesis-related genes including PgSS1, PgSE1, and dammarenediol synthase (PgDDS), which is similar to that of treatment with MJ. However, MJ treatment of transgenic ginseng significantly enhanced JA and MJ, associated with a 2.8-fold increase of ginsenoside content compared with the non-treated, non-transgenic control plant, which was 1.4 times higher than the MJ treatment effect on non-transgenic plants. These results demonstrate that PgLOX6 is responsible for the biosynthesis of JA and promotion of the production of triterpenoid saponin through up-regulating the expression of ginsenoside biosynthetic genes. This work provides insight into the role of JA in biosynthesizing secondary metabolites and provides a molecular tool for increasing ginsenoside production.

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Oxylipins: Structurally diverse metabolites from fatty acid oxidation

Cited by 376 publications

References 119 publications

The Reductase Activity of the Arabidopsis Caleosin RESPONSIVE TO DESSICATION20 Mediates Gibberellin-Dependent Flowering Time, Abscisic Acid Sensitivity, and Tolerance to Oxidative Stress

The Reductase Activity of the Arabidopsis Caleosin RESPONSIVE TO DESSICATION20 Mediates Gibberellin-Dependent Flowering Time, Abscisic Acid Sensitivity, and Tolerance to Oxidative Stress

Formation Mechanism of Aroma Compound during Tea Manufacturing Process

PgLOX6 encoding a lipoxygenase contributes to jasmonic acid biosynthesis and ginsenoside production in Panax ginseng

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