Cytotoxicity and antitumor activities of fungal bis(naphtho-.GAMMA.-pyrone) derivatives.

Koyama, Kiyotaka; Ominato, Kimie; Natori, Shinsaku; Tashiro, Tazuko; Tsuruo, Takashi

doi:10.1248/bpb1978.11.630

Cited by 64 publications

(65 citation statements)

References 9 publications

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“…Ustilaginoidin A (15) from Ustilaginoidea virens showed relatively weak cytotoxic activity [54]. Chaetochromins A (1), B (4), C (8) and D (9) exhibited strong cytotoxicity on KB cells by inhibiting deoxyribonucleic acid, ribonucleic acid and protein biosynthesis [2]. Further mechanism of action investigations for chaetochromin A (1) revealed that the ATP synthesis in mitochondria was inhibited by uncoupling oxidative phosphorylation and depressing state-3 respiration of mitochondria, which may explain their cytotoxicity and in vivo toxicity to animals [55].…”

Section: Cytotoxic and Antitumor Activitymentioning

confidence: 99%

“…Both ustilaginoidins D (20) and E (21) exhibited strong cytotoxicity on KB cells by inhibiting biosynthesis of nucleic acid and protein [2]. Ustilaginoidin A (15) also inhibited ATP synthesis in mitochondria by uncoupling oxidative phosphorylation and depressing state-3 respiration of mitochondria [55].…”

Section: Cytotoxic and Antitumor Activitymentioning

confidence: 99%

“…The interest of many OPEN ACCESS investigators in this class of compounds is due to their broad-range biological activities with potential applications in medicine and agriculture [2][3][4]. Until now, fungal bis-naphtho-γ-pyrones and their biological activities have not been reviewed.…”

Section: Introductionmentioning

confidence: 99%

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Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities

Tian

Sun

et al. 2014

Molecules

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Bis-naphtho-γ-pyrones are an important group of aromatic polyketides derived from fungi. They have a variety of biological activities including cytotoxic, antitumor, antimicrobial, tyrosine kinase and HIV-1 integrase inhibition properties, demonstrating their potential applications in medicine and agriculture. At least 59 bis-naphtho-γ-pyrones from fungi have been reported in the past few decades. This mini-review aims to briefly summarize their occurrence, biosynthesis, and structure, as well as their biological activities. Some considerations regarding to synthesis, production, and medicinal and agricultural applications of bis-naphtho-γ-pyrones are also discussed.

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Section: Cytotoxic and Antitumor Activitymentioning

confidence: 99%

Section: Cytotoxic and Antitumor Activitymentioning

confidence: 99%

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Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities

Tian

Sun

et al. 2014

Molecules

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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 .…”

mentioning

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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“…Since crystal structures of HDAC3 and HDAC4 in complex with SAHA have not been determined so far, we used the crystal structure of HDAC8 in complex with SAHA which shows sequence similarity (46%) to HDAC4 [1], for docking experiments of compound 5 g , 5 h , and 6 k . We implemented control docking experiments with SAHA to the crystal structure of HDAC8 using AutoDock program [26,27].…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Design, Synthesis, Molecular Modelling and Biological Evaluation of Novel α-Naphtholhydroxamate Derivatives as Potential Anticancer Agents

Abdelrahim¹,

Mohan²,

Albarrati³

et al. 2016

Med chem (Los Angeles)

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Chemotherapy is one of the treatment options for cancer. A major problem in cancer chemotherapy is the lack of selective toxicity of many commonly used anti-cancer agents towards tumor tissue compared to normal tissue. Studies have shown that α-naphthol is selectively toxic to cultures of human tumor tissue compared to normal tissues in vitro. Hence, this study was conducted to synthesize a series of new hydroxamate derivatives containing α-naphthol nucleus by the reaction of naphthol acetic acid with amino acid methyl ester derivatives which were directly reacted with hydroxyl amine at room temperature. Structures of these compounds were confirmed by standard studies of IR, 1 H NMR, 13 CNMR, MS and elemental analysis. The cytotoxicity of the synthesized compounds were studied using the MTT assay in four human cancer cell lines, including HepG2, PC-3, HT-29 and MCF-7. Among the compounds, compound 6 g and 6 h exhibited a significant cytotoxicity against almost all the used cells including the normal cells . Further studies have shown that the cell death observed was closely associated with generation of reactive oxygen species (ROS). In this study, other naphthol derivatives have shown significant increase in the level of ROS in concentration dependent manner in treated cells. In conclusion, the study has shown that among the synthesized compounds, compounds 6 g , 6 k and 6 h hold the potential for further research. Furthermore, a molecular docking of the tested compounds was carried out to investigate their binding pattern with the prospective target, HDAC (PDB-code: 1T69).

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Cytotoxicity and antitumor activities of fungal bis(naphtho-.GAMMA.-pyrone) derivatives.

Cited by 64 publications

References 9 publications

Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities

Bis-naphtho-γ-pyrones from Fungi and Their Bioactivities

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

Design, Synthesis, Molecular Modelling and Biological Evaluation of Novel α-Naphtholhydroxamate Derivatives as Potential Anticancer Agents

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