Self defensive substances in rice plant against rice blast disease

Kato, Tadahiro; Yamaguchi, Yoshihiro; Uyehara, Tadao; Yokoyama, Toshiro; Namai, Tsuneo; Yamanaka, Susumu

doi:10.1016/s0040-4039(00)86236-x

Cited by 90 publications

(26 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, the presence of a glucuronide moiety on one of the hydroxyl groups indicates that the compounds we have observed were formed in vivo, since conjugation with glucuronic acid implies hepatic processing. Epoxy fatty acids, which can be precursors of fatty acids with vicinal hydroxyl groups, may be derived from the diet (25)(26)(27) or synthesized in vitro.…”

Section: Similarly (M ϫ H)mentioning

confidence: 99%

Glucuronic Acid-conjugated Dihydroxy Fatty Acids in the Urine of Patients with Generalized Peroxisomal Disorders

Street

Evans

Natowicz

1996

Journal of Biological Chemistry

View full text Add to dashboard Cite

Urine extracts from children diagnosed with generalized peroxisomal disorders were screened by continuous flow-negative ion fast atom bombardment-mass spectrometry. In 45 of 60 children with generalized peroxisomal disorders, we observed one or more intense ions (m/z 489, 505, 461, and others) that are infrequently found in children with cholestatic liver disease or normal children. Compounds giving rise to these ions were isolated using reverse phase and anion exchange chromatography. After appropriate derivatization and/or methanolysis the compounds were analyzed using capillary gas chromatography-mass spectrometry. The major compounds were found to be 12,13-dihydroxy-9-octadecenoic acid and 9,10-dihydroxy-12-octadecenoic acid, with one of the hydroxyl groups in glycosidic linkage with glucuronic acid. Minor compounds were glucuronic acid conjugates of 9,10-dihydroxy-octadecanoic acid, and 12,13-dihydroxy-6,9-, 15,16-dihydroxy-9,12-, and 9,10-dihydroxy-12,15-octadecadienoic acids. A series of hexadecanoic, hexadecenoic, and hexadecadienoic acid glucuronides which appear to be ␤-oxidation products of the C18 fatty acids were also observed, with the major species being 10,11-dihydroxy-7-hexadecenoic acid glucuronide. In all, 16 C16 and C18 dihydroxy fatty acids were identified by gas chromatography-mass spectrometry. A series of at least 11 trihydroxy fatty acids was also observed but not fully characterized. Measurement of these compounds may prove to be useful in the diagnosis of some peroxisomal disorders.

show abstract

Section: Similarly (M ϫ H)mentioning

confidence: 99%

Glucuronic Acid-conjugated Dihydroxy Fatty Acids in the Urine of Patients with Generalized Peroxisomal Disorders

Street

Evans

Natowicz

1996

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

“…In microorganisms hydroxy fatty acids are produced from the biotransformation of unsaturated fatty acids (Culleré et al, 2001;Rodríguez et al, 2001;Kuo et al, 2002). Such compounds belong to a class of oxylipins with antifungal activity which have been found in Oryza sativa plants resistant to rice blast disease, and isolated from timothy plants infected by the fungus Epichloe typhina ( Kato et al, 1988). In addition, these type of compounds are reported to perform a variety of biological functions such as anti-inflammatory activity (Dong et al, 2000) or cytotoxic activity (Yoshiki.…”

Section: Introductionmentioning

confidence: 99%

Identification of oxylipins with antifungal activity by LC–MS/MS from the supernatant of Pseudomonas 42A2

Martin-Arjol

Bassas-Galià

Bermudo

et al. 2010

Chemistry and Physics of Lipids

View full text Add to dashboard Cite

In microorganisms hydroxy fatty acids are produced from the biotransformation of unsaturated fatty acids. Such compounds belong to a class of oxylipins which are reported to perform a variety of biological functions such as anti-inflammatory or cytotoxic activity. These compounds have been found in rice and timothy plants after being infected by specific fungus. When grown in submerged culture with linoleic acid, Pseudomonas 42A2 accumulated in the supernatant several hydroxy fatty acids. In this work LC-MS/MS has been used to elucidate the structure of the components form the organic extract: 9-hydroxy-10, 12-octadecadienoic acid; 13-hydroxy-9, 11-octadecadienoic acid; 7, 10-dihydroxy-8E-octadecenoic acid; 9, 10, 13-trihydroxy-11-octadecenoic acid and 9, 12, 13-trihydroxy-10-octadecenoic acid. Antimicrobial activity against several pathogenic fungal strains is presented: MIC (µg/mL) Verticillium dhaliae, 32; Macrophonia phaesolina, 32; Arthroderma uncinatum, 32; Trycophyton mentagrophytes, 64.1

show abstract

“…They can be found in mammalian and microbial cells but also in many plants, where they are involved in defense mechanisms [5]. Rice plants, e.g., utilize linoleic acid ( (9Z,12Z)-octadeca-9,12-dienoic acid) to produce ()-coronaric acid ( (9R,10S,12Z)-9,10-epoxyoctadec-12-enoic acid) [6], seeds from Euphorbia sp. contain optically active ()-vernolic acid ((9Z,12S,13R)-12,13-epoxyoctadec-9-enoic acid) [7].…”

mentioning

confidence: 99%

Metabolism of Deuterated Isomeric 6,7‐Dihydroxydodecanoic Acids in Saccharomyces cerevisiae – Diastereo‐ and Enantioselective Formation and Characterization of 5‐Hydroxydecano‐4‐lactone (=4,5‐Dihydro‐5‐(1‐hydroxyhexyl)furan‐2(3H)‐one) Isomers

Garbe

Tressl

2003

Helvetica Chimica Acta

View full text Add to dashboard Cite

The chemical synthesis of deuterated isomeric 6,7‐dihydroxydodecanoic acid methyl esters 1 and the subsequent metabolism of esters 1 and the corresponding acids 1a in liquid cultures of the yeast Saccharomyces cerevisiae was investigated. Incubation experiments with (6R,7R)‐ or (6S,7S)‐6,7‐dihydroxy(6,7‐2H2)dodecanoic acid methyl ester ((6R,7R)‐ or (6S,7S)‐(6,7‐2H2)‐1, resp.) and (±)‐threo‐ or (±)‐erythro‐6,7‐dihydroxy(6,7‐2H2)dodecanoic acid ((±)‐threo‐ or (±)‐erythro‐(6,7‐2H2)‐1a, resp.) elucidated their metabolic pathway in yeast (Tables 1–3). The main products were isomeric 2H‐labeled 5‐hydroxydecano‐4‐lactones 2. The absolute configuration of the four isomeric lactones 2 was assigned by chemical synthesis via Sharpless asymmetric dihydroxylation and chiral gas chromatography (Lipodex ® E). The enantiomers of threo‐2 were separated without derivatization on Lipodex ® E; in contrast, the enantiomers of erythro‐2 could be separated only after transformation to their 5‐O‐(trifluoroacetyl) derivatives. Biotransformation of the methyl ester (6R,7R)‐(6,7‐2H2)‐1 led to (4R,5R)‐ and (4S,5R)‐(2,5‐2H2)‐2 (ratio ca. 4 : 1; Table 2). Estimation of the label content and position of (4S,5R)‐(2,5‐2H2)‐2 showed 95% label at C(5), 68% label at C(2), and no 2H at C(4) (Table 2). Therefore, oxidation and subsequent reduction with inversion at C(4) of 4,5‐dihydroxydecanoic acid and transfer of 2H from C(4) to C(2) is postulated. The 5‐hydroxydecano‐4‐lactones 2 are of biochemical importance: during the fermentation of Streptomyces griseus, (4S,5R)‐2, known as L‐factor, occurs temporarily before the antibiotic production, and (−)‐muricatacin (=(4R,5R)‐5‐hydroxy‐heptadecano‐4‐lactone), a homologue of (4R,5R)‐2, is an anticancer agent.

show abstract

Self defensive substances in rice plant against rice blast disease

Cited by 90 publications

References 6 publications

Glucuronic Acid-conjugated Dihydroxy Fatty Acids in the Urine of Patients with Generalized Peroxisomal Disorders

Glucuronic Acid-conjugated Dihydroxy Fatty Acids in the Urine of Patients with Generalized Peroxisomal Disorders

Identification of oxylipins with antifungal activity by LC–MS/MS from the supernatant of Pseudomonas 42A2

Metabolism of Deuterated Isomeric 6,7‐Dihydroxydodecanoic Acids in Saccharomyces cerevisiae – Diastereo‐ and Enantioselective Formation and Characterization of 5‐Hydroxydecano‐4‐lactone (=4,5‐Dihydro‐5‐(1‐hydroxyhexyl)furan‐2(3H)‐one) Isomers

Contact Info

Product

Resources

About