The impairing effect of chaetochromin A and related mycotoxins on mitochondrial respiration

Kawai, Kiyoshi; Hisada, Kazuo; Mori, Satoshi; Nozawa, Yoshinori; Koyama, Kiyotaka; Natori, Shinsaku

doi:10.2520/myco1975.1991.31

Cited by 11 publications

(13 citation statements)

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“…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%

“…Reactive oxygen species generation and loss of the mitochondrial membrane potential (MMP) were also markedly induced by cephalochromin [18]. Cephalochromin (11) 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%

“…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 potential applications of bis-naphtho-γ-pyrones as antitumor agents, antimicrobials, and antivirus agents as well as their promising bioactivities have led to considerable interest within the pharmaceutical community. Chemical syntheses have been achieved for a few bioactive bis-naphtho-γ-pyrones such as ustilaginoidin A (15) [67] and nigerone (55) [68,69]. After comprehensive understanding of biosynthetic pathways of some bis-naphtho-γ-pyrones in the next few years, we can effectively not only increase yields of the bioactive bis-naphtho-γ-pyrones (i.e., cephalochromin, isochaetochromins B 1 and B 2 ), but also prevent biosynthesis of some toxic bis-naphtho-γ-pyrones (i.e., ustilaginoidins A-J) [70].…”

Section: Conclusion and Future Perspectivesmentioning

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%

“…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%

Section: Conclusion and Future Perspectivesmentioning

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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“…Ustilaginoidins have been previously shown to have a certain toxicity and teratogenicity to embryonic limb bud and midbrain cells in mouse (Tsuchiya et al, 1987). Ustilaginoidins A was revealed to uncouple the oxidative phosphorylation, and thus, strongly inhibiting mitochondrial respiration (Kawai et al, 1991). Ustilaginoidins D and E exhibit a strong effect on mouth epidermal carcinoma cells in human by inhibiting the synthesis of DNA, RNA and proteins .…”

Section: Introductionmentioning

confidence: 99%

Towards understanding the biosynthetic pathway for ustilaginoidin mycotoxins in Ustilaginoidea virens

Wang

Liu

et al. 2019

Environmental Microbiology

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Summary Ustilaginoidins, toxic to plants, animals and human, are one of major types of mycotoxins produced by Ustilaginoidea virens. In this study, a gene cluster containing the polyketide synthase gene UvPKS1 was analysed via gene replacement and biochemical studies to determine ustilaginoidin biosynthetic pathway in U. virens. UvPKS1 was first proven to be responsible for the first step of ustilaginoidin biosynthesis, since neither ustilaginoidin derivatives nor intermediates were produced when UvPKS1 was deleted. Replacement of ugsO greatly reduced ustilaginoidin production but increased the ratios of dehydrogenated/hydrogenated ustilagioidin derivatives. The enhanced growth rate of the ΔugsO mutant indicates that accumulation of certain ustilaginoidin derivatives may adversely affect mycelial growth in U. virens. Deletion of ugsT encoding a putative MFS transporter disrupted the ability to generate ustilaginoidins. The ustilaginoidin derivatives produced in the ΔugsJ mutant all lack C3‐methyl, indicating that UgsJ is responsible for C3‐methylation. Only monomeric intermediates, such as 3‐methyl‐dihydro‐nor‐rubrofusarin, but no ustilaginoidin derivatives were generated in the ΔugsL mutant, indicating that UgsL is responsible for the dimerization of nor‐rubrofusarin derivatives to produce ustilaginoidins. However, ugsR2 deletion had no dramatic effect on ustilaginoidin biosynthesis. Together, biochemical analyses with bioinformatics and chemoinformatics uncover a multiple‐step enzyme‐catalysed pathway for ustilaginoidin biosynthesis in U. virens.

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Reexamination of respiration-impairing effect of bikaverin on isolated mitochondria

et al. 1998

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Kovac et al (1) have shown that bikaverin uncouples oxidative phosphorylation of mitochondria at 20µg/ml (52 nmol/ml) in the reaction system without magnesium (Mg(2+)). In the present study, the effects of bikaverin on mitochondrial reactions were reexamined in detail at various concentrations both in the reaction systems with and without magnesium, using isolated rat liver mitochondria and submitochondrial particles (SMP) to characterize its mode of actions to mitochondrial respiration at low concentrations (<30nmol/mg mitochondrial protein).It was concluded that bikaverin showed no uncoupling effect (no decrease in P/O ratio) at low concentrations and did it at high concentrations in consequence of disturbing the ion permeability in the mitochondrial inner membranes. At low concentrations, bikaverin repressed both NAD- and succinate-linked respirations, but did not interfere with electron transport and energy transfer systems of mitochondria.

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The impairing effect of chaetochromin A and related mycotoxins on mitochondrial respiration

Abstract: Chaetochromin A and related bis (naphtho-ƒÁ-pyrone) mycotoxins, cephalochromin and ustilaginoidin A, were examined for the injuring effects on mitochondrial respiration by using isolated rat liver mitochondria to gain insight into the molecular mechanism for their in vivo toxicity.

Cited by 11 publications

References 0 publications

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

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

Towards understanding the biosynthetic pathway for ustilaginoidin mycotoxins in Ustilaginoidea virens

Reexamination of respiration-impairing effect of bikaverin on isolated mitochondria

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