Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea

Chen, Haifeng; Han, Xinya; Nian, Qin; Lin, Wenhan; Yang, Yanwen; Rao, Li; Chi, Bo; Feng, Lingling; Ren, Yanliang; Wan, Jian

doi:10.1016/j.bmc.2016.01.053

Cited by 12 publications

(19 citation statements)

References 34 publications

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“…Failure to melanise the fungal cell wall results in immature appressoria that cannot generate the turgor pressure required to penetrate host tissues [4,5]. Tricyclazole, pyroquilon and other commercial compounds that inhibit DHN melanin biosynthesis are highly effective at preventing rice blast [6–8]. The same role in plant penetration was reported in several other plant pathogens, including Colletotrichum kahawae and Diplocarpon rosae , pathogens of coffee berries and roses, respectively [9,10].…”

Section: Introductionmentioning

confidence: 99%

Assignment of a dubious gene cluster to melanin biosynthesis in the tomato fungal pathogen Cladosporium fulvum

et al. 2018

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Pigments and phytotoxins are crucial for the survival and spread of plant pathogenic fungi. The genome of the tomato biotrophic fungal pathogen Cladosporium fulvum contains a predicted gene cluster (CfPKS1, CfPRF1, CfRDT1 and CfTSF1) that is syntenic with the characterized elsinochrome toxin gene cluster in the citrus pathogen Elsinoë fawcettii. However, a previous phylogenetic analysis suggested that CfPks1 might instead be involved in pigment production. Here, we report the characterization of the CfPKS1 gene cluster to resolve this ambiguity. Activation of the regulator CfTSF1 specifically induced the expression of CfPKS1 and CfRDT1, but not of CfPRF1. These co-regulated genes that define the CfPKS1 gene cluster are orthologous to genes involved in 1,3-dihydroxynaphthalene (DHN) melanin biosynthesis in other fungi. Heterologous expression of CfPKS1 in Aspergillus oryzae yielded 1,3,6,8-tetrahydroxynaphthalene, a typical precursor of DHN melanin. Δcfpks1 deletion mutants showed similar altered pigmentation to wild type treated with DHN melanin inhibitors. These mutants remained virulent on tomato, showing this gene cluster is not involved in pathogenicity. Altogether, our results showed that the CfPKS1 gene cluster is involved in the production of DHN melanin and suggests that elsinochrome production in E. fawcettii likely involves another gene cluster.

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Section: Introductionmentioning

confidence: 99%

Assignment of a dubious gene cluster to melanin biosynthesis in the tomato fungal pathogen Cladosporium fulvum

et al. 2018

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“…β‐Nitrostyrenes derivatives display several biological activities: antibacterial, fungicidal, antileishmanial, anti‐inflammatory, antiplatelet, pro‐apoptotic, and anticancer . Nitroderivatives occur rarely in nature.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of the vasorelaxant effect induced by trans‐4‐methyl‐β‐nitrostyrene, a synthetic nitroderivative, in rat thoracic aorta

Teófilo

Arruda-Barbosa

Rodrigues-Silva

et al. 2017

Clin Exp Pharma Physio

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Mechanisms underlying the vasorelaxant effects of trans-4-methyl-β-nitrostyrene (T4MeN) were studied in rat aortic rings. In endothelium-intact preparations, T4MeN fully and similarly relaxed contractions induced by phenylephrine (PHE) (IC = 61.41 [35.40-87.42] μmol/L) and KCl (IC = 83.50 [56.63-110.50] μmol/L). The vasorelaxant effect of T4MeN was unchanged by endothelium removal, pretreatment with L-NAME, indomethacin, tetraethylammonium, ODQ or MDL-12,330A. Under Ca -free conditions, T4MeN significantly reduced with a similar potency: (i) phasic contractions induced by PHE, but not by caffeine; (ii) contractions due to CaCl in aortic preparations stimulated with PHE (in the presence of verapamil) or high KCl; (iii) contractions evoked by the restoration of external Ca levels after depletion of intracellular Ca stores in the presence of thapsigargin. In contrast, T4MeN was more potent at inhibiting contractions evoked by the tyrosine phosphatase inhibitor, sodium orthovanadate, than those induced by the activator of PKC, phorbol-12,13-dibutyrate. These results suggest that T4MeN induces an endothelium- independent vasorelaxation that appears to occur intracellularly through the inhibition of contractions that are independent of Ca influx from the extracellular milieu but involve phosphorylation of tyrosine residues.

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“…The organic phase was washed with saturated aqueous NaCl solution, dried over anhydrous Na 2 SO 4 , filtered, and evaporated under reduced pressure. The residue was used in the next step without purification . Step 2: LiAIH 4 (40 mL,1 M in THF) was added dropwise to a solution of the residue of previous step in anhydrous Et 2 O (20 mL) in three neck-flask over a period of 1 h at 0 °C with vigorous stirring.…”

Section: Methodsmentioning

confidence: 99%

“…Purification of products was performed by flash chromatography (FC) using silica gel or preparative thin-layer chromatography. 1 H and 13 C NMR spectra were recorded on a Bruker AVANCE III spectrometer (400 and 101 MHz, respectively) and a JEOL ECZ600S (600 and 151 MHz, respectively). Chemical shifts are reported parts per million (ppm) referenced to CDCl 3 (δ 7.26 ppm), tetramethylsilane (TMS, δ 0.00 ppm), and D 2 O (δ 4.79 ppm) for 1 H NMR; CDCl 3 (δ 77.16 ppm) for 13 C NMR.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed C(sp²)–H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines

et al. 2019

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A rapid construction of THIQs by a Pd(II)catalyzed C(sp 2 )−H olefination of free primary and secondary 2-phenylethylamines with high step-and atom-economy was reported. Notably, no substituent was required at the αposition to the amino group of the 2-phenylethylamines. The substrate scope was broad, and the reaction could also be applied to generate THIQs from the biologically active molecules such as the drug molecule baclofen and phenylalanine ester.

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Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea

Cited by 12 publications

References 34 publications

Assignment of a dubious gene cluster to melanin biosynthesis in the tomato fungal pathogen Cladosporium fulvum

Assignment of a dubious gene cluster to melanin biosynthesis in the tomato fungal pathogen Cladosporium fulvum

Mechanism of the vasorelaxant effect induced by trans‐4‐methyl‐β‐nitrostyrene, a synthetic nitroderivative, in rat thoracic aorta

Palladium-Catalyzed C(sp²)–H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines

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Synthesis and biological evaluation of novel inhibitors against 1,3,8-trihydroxynaphthalene reductase from Magnaporthe grisea

Cited by 12 publications

References 34 publications

Assignment of a dubious gene cluster to melanin biosynthesis in the tomato fungal pathogen Cladosporium fulvum

Assignment of a dubious gene cluster to melanin biosynthesis in the tomato fungal pathogen Cladosporium fulvum

Mechanism of the vasorelaxant effect induced by trans‐4‐methyl‐β‐nitrostyrene, a synthetic nitroderivative, in rat thoracic aorta

Palladium-Catalyzed C(sp2)–H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines

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Product

Resources

About

Palladium-Catalyzed C(sp²)–H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines