Effect on ergosterol biosynthesis of a fungicide, SSF-109, in Botrytis cinerea

Shirane, Noboru; Murabayashi, Akira; Masuko, Michio; Uomori, Atsuko; Yoshimura, Y.; Seo, Shujiro; Uchida, Keiji; Takeda, Ken’ichi

doi:10.1016/0031-9422(90)85178-i

Cited by 28 publications

(14 citation statements)

References 19 publications

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“…Because of the presence of eburicone, which is not a normal intermediate in sterol C‐4 demethylation, it could be concluded that DMIs have no effect on 3‐keto reduction. This sterone accumulation would be an indirect consequence of a detoxification process, as proposed by Shirane et al 28 Moreover, it has been shown with maize microsomes that sterone reduction appears insensitive to DMIs 13…”

Section: Discussionmentioning

confidence: 83%

“…Some sterone accumulation was seen following treatment of some fungi with some DMIs 27–32. Obtusifolione was always found, sometimes accompanied by 14α‐methylfecosterone, whereas eburicone was detected depending on the DMI and the fungus 28–30. Because of the presence of eburicone, which is not a normal intermediate in sterol C‐4 demethylation, it could be concluded that DMIs have no effect on 3‐keto reduction.…”

Section: Discussionmentioning

confidence: 99%

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The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

Debieu

Bach

Hugon

et al. 2001

Pest Management Science

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Fenhexamid, a recently developed botryticide, is shown here to inhibit sterol biosynthesis. When the fungus Botryotinia fuckeliana was grown in the presence of fenhexamid, the ergosterol content was reduced, and three 3-keto compounds, 4 alpha-methylfecosterone, fecosterone and episterone, accumulated, suggesting an inhibition of the 3-keto reductase involved in C-4 demethylation. Thus, fenhexamid belongs to a new, promising class of sterol biosynthesis inhibitors not previously used in agriculture or in medicine.

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Section: Discussionmentioning

confidence: 83%

Section: Discussionmentioning

confidence: 99%

The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

Debieu

Bach

Hugon

et al. 2001

Pest Management Science

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“…Chromatographic fractionation and purification of M. aeruginosa TC-3 led to the isolation of ergosterol (1), stigmasterol (2), and b-sitosterol (3). Their structures were identified by mean of spectroscopic data in comparison with those reported (Shirane et al, 1990;Greca et al, 1990;Chaurasia and Wichtl, 1987). Compound 1 strongly inhibited NF-jB activity with IC 50 of 0.91 lg/ml while 2 and 3 were inactive in TNF-a stimulated HeLa cells.…”

Section: Resultsmentioning

confidence: 99%

Inhibitory effects on nuclear factor κB of the Vietnamese freshwater cyanobacteria

Dat

Duong

et al. 2010

Med Chem Res

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Several Vietnamese freshwater cyanobacteria were collected and evaluated for their effects on the transcriptional nuclear factor jB (NF-jB) which are involving in the cancer and inflammatory diseases. Five extraction conditions were tested and a solution of 2% acetic acid in methanol provided highest yield of extract from bacterial biomass. The Microcystis aeruginosa TC-1 and TC-3 strains showed strong NF-jB inhibitory activity with IC 50 values of 6.1 and 5.3 lg/ml, respectively. Moreover, all tested cyanobacteria exhibited cytotoxicity on human cervical cancer HeLa cells in a dose-dependent manner. Ergosterol (1) isolated from M. aeruginosa TC-3 strains strongly inhibited NF-jB activation with IC 50 values of 0.91 lg/ml.

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“…Treated cultures with MCOD did not accumulate abnormal sterol resulting from alternative pathways. Shirane et al . (1990) reported that the fungicide (dL)‐ cis ‐1‐(4‐chlorophenyl)‐2(1 H‐1,2,4‐triazol‐1‐yl)cycloheptanol inhibited the biosynthesis of ergosterol at the 14‐demethylation step, resulting in the accumulation of several other sterols.…”

Section: Discussionmentioning

confidence: 99%

“…Treated cultures with MCOD did not accumulate abnormal sterol resulting from alternative pathways. Shirane et al (1990) reported that the fungicide (dL)-cis-1-(4-chlorophenyl)-2(1 H-1,2,4-triazol-1-yl)cycloheptanol inhibited the biosynthesis of ergosterol at the 14demethylation step, resulting in the accumulation of several other sterols. Quail et al (1993) determined that B. cinerea initially accumulated 24-methylene-24(25)-dihydrolanosterol, and then obtusifolione, during growth arrest.…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial activity of methyl cis-7-oxo deisopropyldehydroabietate on Botrytis cinerea and Lophodermium seditiosum: ultrastructural observations by transmission electron microscopy

Feio

França²,

Silva

et al. 2002

J Appl Microbiol

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Aims: To study the antifungal activity of methyl cis-7-oxo-deisopropyldehydroabietate (MCOD) against phytopathogenic fungi, Botrytis cinerea and Lophodermium seditiousm. The effect of the compound was studied by transmission electron microscopy (TEM) and the composition of sterols on both treated and untreated cultures was determined. Methods and Results: MCOD was tested at concentrations in the range 0AE003-0AE5% by the agar plate dilution method. The radial growth of the colonies treated with MCOD was measured against colonies from untreated cultures. The radial growth of colonies of both fungi and the spore germination of B. cinerea were partially or completely inhibited. Fragments of active growing colonies treated and untreated with MCOD were submitted to the conventional procedure for ultrastructural observation by TEM. Observations by TEM on colonies of B. cinerea and L. seditiosum under 0AE1% MCOD revealed several autophagic-like vacuoles, morphological alterations on lomasome and lipid accumulations in the apical zone of hyphae of both fungi. Observations on spore germination of B. cinerea revealed the presence of strongly stained lipid accumulations retained by vacuoles at the cell periphery of young hyphae. The sterol composition of B. cinerea and L. seditiosum was determined on MCOD treated and untreated cultures by gas-chromatography ⁄ mass-spectrometry (GC-MS) with molecular ions and fragmentation patterns characteristics of ergosterol (M + 396) and dihydroergosterol (M + 398) in both fungi. Conclusions: The morphological alterations are consistent with an unspecific mode of action of MCOD causing inhibition of normal growth or damaging the fungi cells. TEM observations suggest a mechanism of resistance based on the retention of MCOD by the lipid accumulation. Significance and Impact of the Study: The results obtained in the present work afforded a better understanding of the mode of action of a resin acid derivative on phytopathogenic fungi. The inhibition growth of both fungi by MCOD demonstrates the antifungal activity of this compound and the interest on further in vivo studies, in order to evaluate its potential as a benign alternative to conventional fungicides.

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Effect on ergosterol biosynthesis of a fungicide, SSF-109, in Botrytis cinerea

Cited by 28 publications

References 19 publications

The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

The hydroxyanilide fenhexamid, a new sterol biosynthesis inhibitor fungicide efficient against the plant pathogenic fungus Botryotinia fuckeliana (Botrytis cinerea)

Inhibitory effects on nuclear factor κB of the Vietnamese freshwater cyanobacteria

Antimicrobial activity of methyl cis-7-oxo deisopropyldehydroabietate on Botrytis cinerea and Lophodermium seditiosum: ultrastructural observations by transmission electron microscopy

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