Unsaturated Hydroxy Fatty Acids, the Self Defensive Substances in Rice Plant Against Rice Blast Disease

Kato, Tadahiro; Yamaguchi, Yoshihiro; Hirano, Takumi; Yokoyama, Toshiro; Uyehara, Tadao; Namai, Tsuneo; Yamanaka, Susumu; Harada, Nobuyuki

doi:10.1246/cl.1984.409

Cited by 150 publications

(52 citation statements)

References 4 publications

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“…From a phylogenic point of view, it is interesting that the metabolic pathway of C18-epoxides resembles that already described in higher plants (39). Interestingly, it has been shown that certain cutin monomers (i.e., 9,10,18-TriSTA), which are released from the plant cuticle by fungal cutinases, may protect the plant against fungal infection by inducing the plant defense mechanisms (2). It will be of great interest to further examine the possible metabolic and functional effects of these metabolites in mammals at the molecular and physiological levels.…”

Section: Discussionmentioning

confidence: 76%

“…Epoxidized fatty acids from the C18 family (C18-epoxides) such as Z 9(10)-epoxyoctadecanoic acid [ Z 9(10)-EpSTA], Z 9(10)-epoxyoctadec-Z 12-enoic acid [ Z 9(10)-EpOME, leukotoxin], and Z 12(13)-epoxyoctadec-Z 9-enoic acid [ Z 12(13)-EpOME, isoleukotoxin] should be regarded as toxic and/or defensive substances in living beings because they have been described as toxic metabolites in mammals (1) and as defense compounds in infected plants (2,3). The conversion of fatty acid epoxides to the corresponding vicinal diol by epoxide hydrolases (EHs) is thought to be the general pathway for fatty acid epoxide clearance (4-9), although recently, Fang et al (10) reported the conversion of epoxyeicosatrienoic acid (EET) to a chain-shortened epoxide.…”

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confidence: 99%

“…We investigated the metabolism of three epoxides derived from unsaturated fatty acids of the C18 family and of four isomeric EETs using both human microsomes and a series of human recombinant cytochrome P450s. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] C] Z 9(10)-EpOME (6.4 Ci/mol), and [1-14 C] Z 12(13)-EpOME (6.2 Ci/mol) were from Commissariat à l'Energie Atomique (Gif sur Yvette, France). AA, Z 5(6)EET, Z 8(9)EET, Z 11(12)EET, Z 14(15)EET, Z 9(10)-EpSTA, Z 9(10)-EpOME, Z 12(13)-EpOME, palmitoleic acid, lauric acid, and ␣ -tocopherol were obtained from Cayman Chemicals (SPI Bio, Massy, France).…”

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confidence: 99%

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Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides

Quéré

Plée-Gautier

Potin

et al. 2004

Journal of Lipid Research

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CYP4F isoforms are involved in the oxidation of important cellular mediators such as leukotriene B 4 (LTB4) and prostaglandins. The proinflammatory agent LTB4 and cytotoxic leukotoxins have been associated with several inflammatory diseases. We present evidence that the hydroxylation of Z 9(10)-epoxyoctadecanoic, Z 9(10)-epoxyoctadec-Z 12-enoic, and Z 12(13)-epoxyoctadec-Z 9-enoic acids and that of monoepoxides from arachidonic acid [epoxyeicosatrienoic acid (EET)] is important in the regulation of leukotoxin and EET activity. These three epoxidized derivatives from the C18 family (C18-epoxides) were converted to 18-hydroxy-C18-epoxides by human hepatic microsomes with apparent K m values of between 27.6 and 175 M. Among recombinant P450 enzymes, CYP4F2 and CYP4F3B catalyzed mainly the -hydroxylation of C18-epoxides with an apparent V max of between 0.84 and 15.0 min ؊ 1 , whereas the apparent V max displayed by CYP4F3A, the isoform found in leukocytes, ranged from 3.0 to 21.2 min ؊ 1 . The rate of -hydroxylation by CYP4A11 was experimentally found to be between 0.3 and 2.7 min ؊ 1 . CYP4F2 and CYP4F3 exhibited preferences for -hydroxylation of Z 8(9)-EET, whereas human liver microsomes preferred Z 11(12)-EET and, to a lesser extent, Z 8(9)-EET. Moreover, vicinal diol from both C18-epoxides and EETs were -hydroxylated by liver microsomes and by CYP4F2 and CYP4F3. These data support the hypothesis that the human CYP4F subfamily is involved in the -hydroxylation of fatty acid epoxides. These findings demonstrate that another pathway besides conversion to vicinal diol or chain shortening by ␤ -oxidation exists for fatty acid epoxide inactivation. -Le Quéré, V., E. Plée-Gautier, P. Potin, S. Madec, and J-P. Salaün. Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides.

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Section: Discussionmentioning

confidence: 76%

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confidence: 99%

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confidence: 99%

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Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides

Quéré

Plée-Gautier

Potin

et al. 2004

Journal of Lipid Research

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“…Our previous work showed that an activity that decomposed lipid hydroperoxides (LHDA) was present in rice seeds (17). The results indicated that the activity converted 1 3-HPODD (9-HPODD) to 1 3-HODD (9-HODD) and 9,10,1 3-trihydroxyoctadec-11 -enoic acid (9,12,1 3-trihydroxyoctadec-lO-enoic acid), which had antifungal activity against the rice blast fungus (10,1,17). We observed that LHDA in rice leaves also produced the hydroxy fatty acids, but it is possible that other enzymes that convert lipid hydroperoxides to their special products are present in the fungus-infected leaves.…”

Section: Antifungal Activities Of Hydroperoxy and Hydroxy Fatty Acidsmentioning

confidence: 99%

A Lipoxygenase Pathway Is Activated in Rice after Infection with the Rice Blast Fungus Magnaporthe grisea

Ohta¹,

Shida²,

Peng³

et al. 1991

Plant Physiol.

111

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Lipoxygenase (LOX) and lipid hydroperoxide-decomposing activity (LHDA) markedly increased in the fifth leaves of rice (Oryza sativa cv Aichiasahi) after infection with the rice blast fungus, Magnaporthe grisea. The increases in the enzyme activities were significantly higher in response to infection with an incompatible strain (race 131) compared with infection with a compatible strain (race 007) of the fungus. Using ion-exchange chromatography, we isolated three LOX activities (leaf LOX-1, -2, -3) from both uninoculated and infected leaves. The activity of leaf LOX-3, in particular, increased in the incompatible race-infected leaves. The leaf LOX-3 had a pH optimum of 5.0 and produced preferentially 13-L-hydroperoxy-9,11 (Z,E)-octadecadienoic acid (13-HPODD) from linoleic acid. 13-HPODD and 13-L-hydroxy-9,11 (Z,E)-octadecadienoic acid, one of the reaction products from 13-HPODD by LHDA, were highly inhibitory to the germination of conidia of the fungus. The present study provides correlative evidence for important roles of LOX and LHDA in the resistance response of rice against the blast fungus.Rice (Oryza sativa) blast, caused by Magnaporthe grisea, is one of the most destructive rice diseases. Many studies have been concerned with resistance mechanisms of rice to the blast fungus, and, thus, several antifungal substances have been isolated from rice leaves (1, 4, 9-1 1, 14). However, the biosynthetic mechanisms of these substances in fungal-infected leaves have not been established. Therefore, it is not known whether the antifungal substances isolated from rice leaves are actually involved in the defense response of rice against the fungus.We recently found an activity that decomposed lipid hy-

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“…LOX has been found to participate in the synthesis of hydroperoxy fatty acids as exemplified in the case of linolenic acid (1), which is oxidized to a hydroperoxy derivative (2) by the action of LOX and oxygen molecules. The corresponding allyl alcohol (3), the main anti-rice blast fungus substance isolated from infected rice plants, has a strong inhibitory activity toward germination of rice blast fungus while 2 has quite powerful cytotoxicity to rice leaves as well as an anti-blast fungus activity.2,3) Thus the LOX activity increment has been proposed to be correlated with the defense of rice plants against rice blast disease.…”

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confidence: 99%

Lipoxygenase Activity Increment in Infected Tomato Leaves and Oxidation Product of Linolenic Acid by ItsIn VitroEnzyme Reaction

Kato

Maeda

Hirukawa

et al. 1992

Bioscience, Biotechnology, and Biochemistry

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Unsaturated Hydroxy Fatty Acids, the Self Defensive Substances in Rice Plant Against Rice Blast Disease

Abstract: In addition to the previously described epoxy fatty acids, five hydroxy fatty acids were characterized as self defensive substances produced in the rice plant against rice blast disease.

Cited by 150 publications

References 4 publications

Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides

Human CYP4F3s are the main catalysts in the oxidation of fatty acid epoxides

A Lipoxygenase Pathway Is Activated in Rice after Infection with the Rice Blast Fungus Magnaporthe grisea

Lipoxygenase Activity Increment in Infected Tomato Leaves and Oxidation Product of Linolenic Acid by ItsIn VitroEnzyme Reaction

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