Zoosporicidal metabolites from an endophytic fungus Cryptosporiopsis sp. of Zanthoxylum leprieurii

Talontsi, Ferdinand Mouafo; Facey, Petrea; Tatong, Michel D. Kongue; Islam, Tofazzal; Frauendorf, Holm; Draeger, Siegfried; Tiedemann, Andreas von; Laatsch, Hartmut

doi:10.1016/j.phytochem.2012.06.006

Cited by 46 publications

(29 citation statements)

References 23 publications

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“…The molecular formula was determined as C 19 H 21 ClO 6 by HRESIMS. The NMR (Tables 1 and 2), HRMS, and specific rotation data were similar to those for a recently reported RAL analogue, cryptosporiopsin A, described by Talontsi et al 20 in 2012 from a culture of Cryptosporiopsis sp., an endophytic fungus from leaves and branches of Zanthoxylum leprieurii (Rutaceae). Although the planar structure between 1 and cryptosporiopsin A was identical, a new trivial name for 1 has been proposed for two reasons.…”

Section: Resultssupporting

confidence: 80%

“…First, and as explained in more detail below, we have strong evidence that the absolute configuration for 1 at position 2 is S . In contrast, cryptosporiopsin A was drawn as 2 R ; however, those authors did not discuss their reasoning for this conclusion, although it could be due to similarities to ponchonin D. 20,21 Moreover, the trivial name proposed by those authors 20 was utilized in 1969 for a structurally unrelated compound. 22,23 As such, compound 1 was ascribed the new trivial name, greensporone A.…”

Section: Resultsmentioning

confidence: 95%

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Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.

et al. 2014

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Fourteen new resorcylic acid lactones (1–14) were isolated from an organic extract of a culture of a freshwater aquatic fungus Halenospora sp. originating from a stream in North Carolina. The structures were elucidated using a set of spectroscopic and spectrometric techniques. The absolute configuration of one representative member of the compounds (7) was assigned using X-ray crystallography of an analogue that incorporated a heavy atom, whereas for compounds 8–11, a modified Mosher’s ester method was utilized. The relative configurations of compounds 12–14 were determined on the basis of NOE data. Compounds 12–14 were proposed as artifacts produced by intramolecular cycloetherification of the ε-hydroxy-α,β-unsaturated ketone moieties of the parent compounds during the purification processes. The isolated compounds, except for 8 and 12, were tested against the MDA-MB-435 (melanoma) and HT-29 (colon) cancer cell lines. Compound 5 was the most potent, with IC50 values of 2.9 and 7.5 μM, respectively. The compounds were evaluated as TAK1–TAB1 inhibitors but were found to be inactive.

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Section: Resultssupporting

confidence: 80%

Section: Resultsmentioning

confidence: 95%

Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.

et al. 2014

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“…The bioassay was performed according to previously described procedures. 18 Fungal conidia were washed out from media with 0.1% solution of Tween-80, adjusted to an appropriate concentration and a suspension (900 μl) was added to the wells of a 24-well plates. Typically the compound 1 (1 mg) was dissolved in EtOH (50 μl) and then water (950 μl) was added.…”

Section: Biological Activitiesmentioning

confidence: 99%

Biological evaluation and determination of the absolute configuration of chloromonilicin, a strong antimicrobial metabolite isolated from Alternaria sonchi

et al. 2015

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Chloromonilicin was isolated for the first time from Alternaria sonchi, a mycoherbicide proposed for the control of the noxious weed Sonchus arvensis. The already known alternethanoxins A and B and the three recently isolated phytotoxic polycyclic ethanones named alternethanoxins C-E were also isolated from the same source. Chloromonilicin was identified by spectroscopic data (essentially one-dimensional NMR, 2-dimensional NMR and high-resolution ESI-MS) and its structure was confirmed by single X-ray analysis, which also allowed the assignment of the absolute configuration. This latter was independently confirmed by electronic CD calculations. When chloromonilicin was tested for its antimicrobial activity, it was active at concentrations 0.5-1 μg per disc against four bacterial species and a yeast fungus. The compound inhibited conidial germination of four plant pathogens at concentration of 1-10 μg ml(-1). No phytotoxic activity of this antibiotic by leaf-disc puncture bioassay was detected.

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“…The released zoospores remain motile in sterilized water for 12–16 h. These in vitro methods allow screening secondary metabolites from antagonistic environmental microorganisms using convenient bioassay protocols (Islam et al, 2011). In this way, we recently isolated several new secondary metabolites from plants and microorganisms that suppress zoosporogenesis, inhibit motility and/or cause lysis of P. viticola zoospores (Abdalla et al, 2011; Islam et al, 2011; Zinad et al, 2011; Talontsi et al, 2012a,b; Dame et al, 2016). Furthermore, using a natural product, staurosporine and some further kinase inhibitors, we recently demonstrated that protein kinase C is involved in both flagellar motility and zoosporogenesis of the Peronosporomyces (Islam et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Inhibitory Effects of Macrotetrolides from Streptomyces spp. On Zoosporogenesis and Motility of Peronosporomycete Zoospores Are Likely Linked with Enhanced ATPase Activity in Mitochondria

2016

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The release of zoospores from sporangia and motility of the released zoospores are critical in the disease cycle of the Peronosporomycetes that cause devastating diseases in plants, fishes, animals and humans. Disruption of any of these asexual life stages eliminates the possibility of pathogenesis. In the course of screening novel bioactive secondary metabolites, we found that extracts of some strains of marine Streptomyces spp. rapidly impaired motility and caused subsequent lysis of zoospores of the grapevine downy mildew pathogen Plasmopara viticola at 10 μg/ml. We tested a number of secondary metabolites previously isolated from these strains and found that macrotetrolide antibiotics such as nonactin, monactin, dinactin and trinactin, and nactic acids such as (+)-nonactic acid, (+)-homonactic acid, nonactic acid methyl ester, homonactic acid methyl ester, bonactin and feigrisolide C impaired motility and caused subsequent lysis of P. viticola zoospores in a dose- and time-dependent manners with dinactin being the most active compound (MIC 0.3 μg/ml). A cation channel-forming compound, gramicidin, and a carrier of monovalent cations, nigericin also showed similar biological activities. Among all 12 compounds tested, gramicidin most potently arrested the motility of zoospores at concentrations starting from 0.1 μg/ml. All macrotetrolide antibiotics also displayed similar motility impairing activities against P. viticola, Phytophthora capsici, and Aphanomyces cochlioides zoospores indicating non-specific biological effects of these compounds toward peronosporomyctes. Furthermore, macrotetrolide antibiotics and gramicidin also markedly suppressed the release of zoospores from sporangia of P. viticola in a dose-dependent manner. As macrotetrolide antibiotics and gramicidin are known as enhancers of mitochondrial ATPase activity, inhibition of zoosporogenesis and motility of zoospores by these compounds are likely linked with hydrolysis of ATP through enhanced ATPase activity in mitochondria. This is the first report on motility inhibitory and lytic activities of macrotetrolide antibiotics and nactic acids against the zoospores of peronosporomycete phytopathogens.

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Zoosporicidal metabolites from an endophytic fungus Cryptosporiopsis sp. of Zanthoxylum leprieurii

Cited by 46 publications

References 23 publications

Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.

Greensporones: Resorcylic Acid Lactones from an Aquatic Halenospora sp.

Biological evaluation and determination of the absolute configuration of chloromonilicin, a strong antimicrobial metabolite isolated from Alternaria sonchi

Inhibitory Effects of Macrotetrolides from Streptomyces spp. On Zoosporogenesis and Motility of Peronosporomycete Zoospores Are Likely Linked with Enhanced ATPase Activity in Mitochondria

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