Determination of swainsonine in the endophytic Undifilum fungi by high-performance liquid chromatography with evaporative light-scattering detector

Yang, Guodong; Gao, Rui; Yan, Wang; Li, Jincheng; Hu, Yanchun; Kang, Dan-Ju; Li, Yanhong; Li, Haili; Geng, Guoxia; Wang, Jianhua

doi:10.1016/j.toxicon.2012.03.020

Cited by 13 publications

(14 citation statements)

References 25 publications

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“…The synthesis of toxic alkaloids by non-systemic endophytic fungi has been discovered in some plant species in recent years (Cook et al, 2009;Yang et al, 2012). In these cases, a particular fungus with an endophytic lifestyle is able to produce in planta and in vitro a toxic alkaloid.…”

Section: Discussionmentioning

confidence: 99%

“…Till date, few studies have addressed in particular the role of nonsystemic endophytes in plant defensive mechanisms. The endophytic fungus Undifilum oxytropis, which infects several Astragalus and Oxytropis species, has been shown to produce the toxic alkaloid swainsonine (Cook et al, 2009;Yang et al, 2012) and some symbiotic epiphytic fungi living on plant surfaces have also been linked to plant toxicity caused by ergoline alkaloids in Ipomea species (Markert et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Non-systemic fungal endophytes in Carex brevicollis may influence the toxicity of the sedge to livestock

Canals

Emeterio

Sánchez-Márquez

et al. 2014

Span. j. agric. res.

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The sedge Carex brevicollis is a common component of semi-natural grasslands and forests in temperate mountains of Central and Southern Europe. The consumption of this species causes a severe toxicity to livestock, associated to high plant concentrations of the β-carbolic alkaloid brevicolline. This research was started to ascertain the origin of this toxicity. An exploratory survey of alkaloid content in plants growing in contrasting habitats (grasslands/forests) did not contribute to find a pattern of the variable contents of brevicolline in plants, and led us to address other possibilities, such as a potential role of fungal endophytism. Systemic, vertically-transmitted endophytes producers of herbivore-deterrent alkaloids are known to infect many known forage grasses. We did not detect systemic endophytes in C. brevicollis, but the sedge harboured a rich community of non-systemic fungi. To test experimentally whether non-systemic endophytes influenced the synthesis of the alkaloid, 24 plants were submitted to a fungicide treatment to remove the fungal assemblage, and the offspring ramets were analysed for alkaloid content. Brevicolline was the major β-carbolic alkaloid detected, and the contents were at least five times lower in the new ramets that developed from fungicide-treated plants than in the untreated plants. This result, although not conclusive about the primary source of the alkaloid (a plant or a fungal product) indicates that fungal endophytes may affect the contents of the toxic brevicolline in this sedge.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Non-systemic fungal endophytes in Carex brevicollis may influence the toxicity of the sedge to livestock

Canals

Emeterio

Sánchez-Márquez

et al. 2014

Span. j. agric. res.

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“…The three different mobile phases and a gradient HPLC program was optimized for the best resolution of swainsonine peak in chromatograms. A number of chromatographic techniques including LC, gas chromatography (GC), and ion exchange chromatography (IEC) have been reported for the analysis of swainsonine. However, these methods with appreciable sensitivity are either expensive (LCMS), requires the complex derivatization steps (GC) or destructive (GC and IEC).…”

Section: Discussionmentioning

confidence: 99%

“…The extraction of polyhydroxy alkaloids with polar solvents (ethanol, methanol, or water) results in coextraction of broth components like glucose, amino acids, and other such hydrophilic metabolites . There are numerous other methods reported for analysis of swainsonine including enzymatic, liquid‐chromatographic using evaporative light scattering, pulsed amperometric, and mass‐based detectors . However, the above discussed methods are very expensive and generally inaccessible.…”

Section: Introductionmentioning

confidence: 99%

Production, HPLC analysis, and in situ apoptotic activities of swainsonine toward lepidopteran, Sf‐21 cell line

Singh

Kaur

2014

Biotechnology Progress

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Swainsonine, a secondary metabolite from Metarhizium anisopliae has been extensively studied in the complementary areas of therapeutics and toxicology. This work aims to develop a simple UV-HPLC method of analyses for swainsonine in Metarhizium fermentation broth and to explore its in situ entomotoxic activities. The partially purified broth was quantitatively analyzed using middle UV (205 nm)-reverse phase HPLC method with different mobile phases and gradient programmes. Swainsonine was eluted as single peak at (te ) 6.0-6.9 min with average concentration of 4.04 ± 0.52 μg/mL using optimal mobile phase (0.1% trifluoroacetic acid in water and acetonitrile). The mass spectrometry analysis further indicated the characteristic MS1 species for swainsonine, [M+H](+) 174.30 in corresponding HPLC peaks. The antiproliferative effects of swainsonine on lepidopteran, Sf-21 cells were determined through 3-(4, 5-dimethylthia-zol-2-yl)-2, 5-diphenyl tetrazolium bromide (IC50 standard = 3.90 μM and IC50 purified = 5.27 μM) and trypan blue dye exclusion (IC50 standard = 6.91 μM and IC50 purified = 8.67 μM) assays. The fluorescence activated cell sorting evaluation of Sf-21 cells showed nearly 35% and 42% of population in various apoptotic stages at 36 h, when treated with standard and purified swainsonine, respectively. The morphodimensional field emission scanning electron and atomic force microscopic analyses further confirmed the characteristic apoptotic features like membrane blebbings, ruptures and volume shrinkage in the lepidopteran cells after 24-36 h of post-treatment incubation. The study describes the potential entomotoxic activities of swainsonine and its role in the virulence of Metarhizium spp.

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“…However, the use of polar solvents such as ethanol or water also imposes another problem of co-extraction of broth components such as glucose, amino acids and other such hydrophilic metabolites. Several methods have been reported for the analysis and quantification of swainsonine including capillary gas chromatography, thin-layer chromatography, HPLC, LC-MS/MS and HPLC with evaporative light-scattering detector (Yang et al, 2012). Conventional HPLC methods have rarely been applied to swainsonine analysis on account of reasons such as (1) the lack of suitable chromophore groups rendering its UV-visible detection almost impossible and (2) the extreme hydrophilicity of swainsonine ensues the co-elution of small polar molecules such as sugar or amino acids (Molyneux et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

Preparative-cum-quantitative mass-directed analysis of swainsonine and itsin situactivity againstSf-21 cell line

Singh

Kaur

2013

FEMS Microbiol Lett

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Swainsonine is a polyhydroxy indolizidine alkaloid with various research and potential therapeutic applications. In this work, swainsonine was partially purified (2.5-folds) with acetone-methanol solvent system from Metarhizium anisopliae fermentation broth. The partially purified broth was further subjected to mass-directed preparative-cum-quantitative analysis. Swainsonine was eluted as MS1 fraction [M + H](+) 174.36 ± 0.21 at 4.91 ± 0.04 min with calculated yield of 7.85 ± 1.59 μg mL(-1) corresponding to 3.74 × 10(5) counts. In situ antiproliferative activity of standard and purified swainsonine fractions was tested against Spodoptera frugiperda, Sf-21 cell line with IC50 values of 2.96 μM and 3.28 μM, respectively, at 36 h. This analytical procedure for purification and quantitative analysis of swainsonine may ensure its suitability for routine laboratory studies and research.

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Determination of swainsonine in the endophytic Undifilum fungi by high-performance liquid chromatography with evaporative light-scattering detector

Cited by 13 publications

References 25 publications

Non-systemic fungal endophytes in Carex brevicollis may influence the toxicity of the sedge to livestock

Non-systemic fungal endophytes in Carex brevicollis may influence the toxicity of the sedge to livestock

Production, HPLC analysis, and in situ apoptotic activities of swainsonine toward lepidopteran, Sf‐21 cell line

Preparative-cum-quantitative mass-directed analysis of swainsonine and itsin situactivity againstSf-21 cell line

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