Further characterization of seven bis(naphtho-.GAMMA.-pyrone) congeners of ustilaginoidins, coloring matters of Claviceps virens (Ustilaginoidea virens).

Koyama, Kiyotaka; Natori, Shinsaku

doi:10.1248/cpb.36.146

Cited by 54 publications

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“…Ustiloxins inhibit cell division, especially by inhibiting microtubule assembly and cell skeleton formation 8 . Ustilaginoidins are bi(naphtho-g-pyrone) derivatives, which exhibit weak antitumor cytotoxicity to human epidermoid carcinoma 9,10 . RFS thus not only results in severe yield losses in rice 4 but also contaminates rice grain and straw to potentially cause human or animal poisoning 11 .…”

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confidence: 99%

Specific adaptation of Ustilaginoidea virens in occupying host florets revealed by comparative and functional genomics

et al. 2014

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Ustilaginoidea virens (Cooke) Takah is an ascomycetous fungus that causes rice false smut, a devastating emerging disease worldwide. Here we report a 39.4 Mb draft genome sequence of U. virens that encodes 8,426 predicted genes. The genome has B25% repetitive sequences that have been affected by repeat-induced point mutations. Evolutionarily, U. virens is close to the entomopathogenic Metarhizium spp., suggesting potential host jumping across kingdoms. U. virens possesses reduced gene inventories for polysaccharide degradation, nutrient uptake and secondary metabolism, which may result from adaptations to the specific floret infection and biotrophic lifestyles. Consistent with their potential roles in pathogenicity, genes for secreted proteins and secondary metabolism and the pathogen-host interaction database genes are highly enriched in the transcriptome during early infection. We further show that 18 candidate effectors can suppress plant hypersensitive responses. Together, our analyses offer new insights into molecular mechanisms of evolution, biotrophy and pathogenesis of U. virens.

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confidence: 99%

Specific adaptation of Ustilaginoidea virens in occupying host florets revealed by comparative and functional genomics

et al. 2014

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“…Nakamura et al [6] reported that the crude fraction obtained from the water extract of false smut balls or purified ustiloxin A caused liver and kidney damage in mice. Other biologically active substances in the balls, ustilaginoidins, have also been identified from ether extract of the balls [3]. These bis (naphtho-γ-pyrone) derivatives exhibited weak cytotoxicity to human epidermoid carcinoma cells [4].…”

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confidence: 99%

High-Performance Liquid Chromatographic Determination of Ustiloxin A in Forage Rice Silage

Miyazaki

Matsumoto

Uchihara

et al. 2009

The Journal of Veterinary Medical Science

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ABSTRACT. We describe a high-performance liquid chromatographic method for determining ustiloxin A, a mycotoxin produced by Ustilaginoidea virens, in forage rice silage. Lyophilized silage samples were ground and extracted with water. The extracts were purified by solid-phase extraction and subjected to high-performance liquid chromatography using an octadecylsilane-bonded column. Separated ustiloxin A was detected with ultraviolet (UV) absorption at 254 nm. The limit of quantitation for ustiloxin A in silage found to be 2.5 mg/kg. The present method can be used for routine monitoring of the contamination of ustiloxin A in forage rice silage. KEY WORDS: Forage Rice, HPLC, Silage, Ustiloxin A.

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“…Theoretically, there are 16 isomers for the same structure of this dimer. Among them, six isomers, chaetochromins A and B, 3,4 ustilaginoidin D 6 and isochaetochromins A 1 , B 1 and B 2 1,2 ( Figure 3), have been reported so far. Chaetochromin A is a symmetrical dimer having two trans-2,3-dimethyl groups on the 5,6,8-trihydroxy-naphtho-g-pyrone ring, and the absolute stereochemistry was established by CD and X-ray crystallography of p-bromobenzoate derivative.…”

Section: Discussionmentioning

confidence: 99%

“…However, the absolute stereochemistry was not determined. 6 On the other hand, chaetochromin B and isochaetochromins B 1 /B 2 were unsymmetrical dimers having one trans-2,3-dimethyl group and one cis-2,3-dimethyl group, and these axial stereochemistries were elucidated to be aS, aS and aR by CD spectroscopy, respectively. However, it appeared difficult to elucidate the complete stereochemistry of these compounds.…”

Section: Discussionmentioning

confidence: 99%

New isochaetochromin, an inhibitor of triacylglycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: II. structure elucidation

et al. 2011

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The structure of a new congener of chaetochromin, an inhibitor of triacylglycerol synthesis in CHO-K1 cells produced by Penicillium sp. FKI-4942, was elucidated by spectroscopic methods, including various NMR experiments. Isochaetochromin A 1 has a bis-naphtho-c-pyrone moiety. The Journal of Antibiotics (2012) 1 from the culture broth of Penicillium sp. FKI-4942. These compounds were found to inhibit triacylglycerol synthesis in CHO-K1 cells. The taxonomy of the producing fungus, fermentation, isolation and biological properties of isochaetochromins were described in a previous paper. 2 In this study, the physico-chemical properties and structure elucidation of isochaetochromin A 1 are described.

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Further characterization of seven bis(naphtho-.GAMMA.-pyrone) congeners of ustilaginoidins, coloring matters of Claviceps virens (Ustilaginoidea virens).

Cited by 54 publications

References 0 publications

Specific adaptation of Ustilaginoidea virens in occupying host florets revealed by comparative and functional genomics

Specific adaptation of Ustilaginoidea virens in occupying host florets revealed by comparative and functional genomics

High-Performance Liquid Chromatographic Determination of Ustiloxin A in Forage Rice Silage

New isochaetochromin, an inhibitor of triacylglycerol synthesis in mammalian cells, produced by Penicillium sp. FKI-4942: II. structure elucidation

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