Cytochalasins Z1, Z2 and Z3, three 24-oxa[14]cytochalasans produced by Pyrenophora semeniperda

Evidente, Antonio; Andolfi, Anna; Vurro, Maurizio; Zonno, Maria Chiara; Motta, Andréa

doi:10.1016/s0031-9422(02)00071-7

Cited by 62 publications

(85 citation statements)

References 10 publications

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“…Compounds with little or no activity in our bioassays include cavoxin, triacetyl-8-oxo-FC (keto), [14], fusicoccin [9], and seiridin [16] to have moderate phytotoxicity in other systems. However, we found cytochalasin B, 21,22-dihydrocytochalasin B, and ophiobolin A to have weak activity, while others found these compounds to be phytotoxic in other bioassays [7] [13] [45]. Termite Bioassay Results.…”

mentioning

confidence: 68%

“…Brefeldin [3], cyclopaldic acid [6], seiricuprolide [15], cytochalasin B [7], ophiobolin A [13], sphaeropsidin A [17], and cavoxin [4] were purified as pale yellow and white needles from the culture filtrates of Alternaria zinniae, Seridium cupressi, Pyrenophora semeniperda, Drechslera gigantea, and Phoma cava as previously reported. Papuline [14] and seiridin [16] were purified as pure oils from the culture filtrates of Pseudomonas syringae pv.…”

Section: Experimental Partmentioning

confidence: 98%

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A Survey of Phytotoxic Microbial and Plant Metabolites as Potential Natural Products for Pest Management

Schrader¹,

Andolfi

Cantrell³

et al. 2010

Chemistry & Biodiversity

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Phytotoxic microbial metabolites produced by certain phytopathogenic fungi and bacteria, and a group of phytotoxic plant metabolites including Amaryllidacea alkaloids and some derivatives of these compounds were evaluated for algicide, bactericide, insecticide, fungicide, and herbicide activities in order to discover natural compounds for potential use in the management and control of several important agricultural and household structural pests. Among the various compounds evaluated: i) ophiobolin A was found to be the most promising for potential use as a selective algicide; ii) ungeremine was discovered to be bactericidal against certain species of fish pathogenic bacteria; iii) cycasin caused significant mortality in termites; iv) cavoxin, ophiobolin A, and sphaeropsidin A were most active towards species of plant pathogenic fungi; and v) lycorine and some of its analogues (1-O-acetyllycorine and lycorine chlorohydrate) were highly phytotoxic in the herbicide bioassay. Our results further demonstrated that plants and microbes can provide a diverse and natural source of compounds with potential use as pesticides.

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confidence: 68%

Section: Experimental Partmentioning

confidence: 98%

A Survey of Phytotoxic Microbial and Plant Metabolites as Potential Natural Products for Pest Management

Schrader¹,

Andolfi

Cantrell³

et al. 2010

Chemistry & Biodiversity

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“…This fungal species produced a large amount of the phytotoxic CB, as well as CA, CF, deoxaphomin, and the three novel cytochalasins, Z1, Z2, and Z3 [201]. Masi et al [202] found that P. semeniperda was also able to produce phytotoxic sesquiterpenoid penta-2,4-dienoic acid, named pyrenophoric acid which showed strong phytotoxicity on cheatgrass, reducing coleoptile length relative to the control by approximately half at 10 M reduced coleoptile elongation 36% relative to the control.…”

Section: Phytoxicity and Mechanism Of Actionmentioning

confidence: 99%

Mycotoxins: Producing Fungi and Mechanisms of Phytotoxicity

2015

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Abstract:Mycotoxins are secondary fungal metabolites, toxic to humans, animals and plants. Among the hundreds of known mycotoxins, aflatoxins, citrinin, patulin, penicillic acid, tenuazonic acid, ochratoxin A, cytochalasins, deoxynivalenol, fumonisins, fusarin C, fusaric acid, and zearalenone are considered the types that most contaminate cereal grain. The majority of the mycotoxins in these groups are produced by three fungal genera: Aspergillus, Penicillium and Fusarium. These metabolites primarily affect the seed quality, germination, viability, seedling vigour, growth of root and cleoptile. Additionally, since the fungi responsible for the production of these mycotoxins are often endophytes that infect and colonize living plant tissues, accumulation of mycotoxins in the plant tissues may at times be associated with development of plant disease symptoms. The presence of mycotoxins, even in the absence of disease symptoms, may still have subtle biological effects on the physiology of plants. Several studies highlight the toxic effects of mycotoxins on animals and cell lines but little is known about the mode of action of most of these metabolites on plant cells. The most important mycotoxins with phytotoxic effects and their producers in addition to their discovery are briefly outlined below and will be addressed in this article.

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“…Compound 1 exhibited no cytotoxicity against above cell lines (IC 50 > 50 μM) (see Supporting Information Table S1). In seedling assays on wheat (China L-30), 14 compound 2 displayed root elongation inhibitory activity. Compound 2 was able to reduce root length by 4.26, 28.73, and 85.24% at respectively concentration of 1.00 Â 10 À5 , 1.00 Â 10 À4 , and 4.93 Â 10 À4 M (see Supporting Information Table S2).…”

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confidence: 99%

Chaetoconvosins A and B, Alkaloids with New Skeleton from Fungus Chaetomium convolutum

Yang

et al. 2012

Org. Lett.

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Chaetoconvosins A and B (1 and 2), two novel cytochalasan alkaloids with a new 6/6/5/5/7 pentacyclic ring system, were isolated from the solidstate fermented medium of the wheat rhizospheric fungus Chaetomium convolutum cib-100. Their structures were elucidated on the basis of spectroscopic data. The structure of chaetoconvosin A (1) was confirmed by X-ray crystallographic analysis. Chaetoconvosin B (2), the major metabolite, showed remarkable inhibitory ability on root elongation and moderate cytotoxicity against several cancer cell lines.The fungi of the genus Chaetomium are widely distributed in air, soil, plant debris, and endophytic habitats. In the course to study the secondary metabolites of Chaetomium convolutum, two novel cytochalasins, chaetoconvosins A and B (1 and 2), with a new 6/6/5/5/7 penta ring system were isolated, which featured a piperidine-2,6-dione (ring A), a cyclopentanone (ring C), and a 9-oxabicyclo

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Cytochalasins Z1, Z2 and Z3, three 24-oxa[14]cytochalasans produced by Pyrenophora semeniperda

Cited by 62 publications

References 10 publications

A Survey of Phytotoxic Microbial and Plant Metabolites as Potential Natural Products for Pest Management

A Survey of Phytotoxic Microbial and Plant Metabolites as Potential Natural Products for Pest Management

Mycotoxins: Producing Fungi and Mechanisms of Phytotoxicity

Chaetoconvosins A and B, Alkaloids with New Skeleton from Fungus Chaetomium convolutum

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