Characterization and mass spectral analysis of some grayanotoxin derivatives

Jawad, F.H.; Kinghorn, A. Douglas; Doorenbos, Norman J.; Billets, Stephen

doi:10.1002/bms.1200040603

Cited by 8 publications

(3 citation statements)

References 9 publications

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“…Subsequent LC-MS analysis of rumen content confirmed the presence of GTX I at 2.4 µg/g but found no GTX III (Figure 8). While R. maximum has been reported to contain both GTX I and GTX III at >50 µg/g (16), LC-MS analysis of the one sample of R. maximum found 74 µg/g GTX I, 1 µg/g GTX II, and 4 µg/g GTX III. One sample of R. percii contained no GTX I, 4 µg/g GTX II, and 140 µg/g GTX III.…”

Section: Resultsmentioning

confidence: 94%

Determination of Grayanotoxins in Biological Samples by LC-MS/MS

Holstege

Puschner

2001

J. Agric. Food Chem.

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A rapid LC-MS/MS method was developed for the quantitative determination of grayanotoxins I, II, and III in rumen contents, feces, and urine. The grayanotoxins were extracted from solid samples with methanol. The methanol extract was diluted with water and cleaned up using a reversed phase solid phase extraction column. HPLC separation was performed by reversed phase HPLC using a gradient of water and methanol containing 1% acetic acid. Determination was by positive ion electrospray ionization and ion trap tandem mass spectrometry. Grayanotoxin I quantitation was based on fragmentation of the sodium adduct ion at m/z 435 to a product ion at m/z 375. Grayanotoxins II and III were quantitated on the basis of fragmentation of the ion at m/z 335 to the product ion at m/z 299. The method detection limits were 0.2 microg/g in rumen contents and feces and 0.05 microg/g in urine. Fortifications at the detection limits and 10 times the detection limits of bovine rumen contents, caprine feces, and ovine urine were recovered in the range 80-114%. The diagnostic utility of the method was tested by analyzing samples submitted to the veterinary toxicology laboratory.

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Section: Resultsmentioning

confidence: 94%

Determination of Grayanotoxins in Biological Samples by LC-MS/MS

Holstege

Puschner

2001

J. Agric. Food Chem.

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“…There was one hydroxyl group at C‐3 but none at C‐2, which was characteristic of this group. Scheme showed a possible fragmentation pathway in which neutral loss and McLafferty rearrangement played an important role (Jawad et al ., ). As reported in the literature, the fragment ion peak of m/z 257.1547 could be interpreted as follows: grayanotoxin III ( 3 ) lost three molecules of water at first and then the C–C bond between C‐13 and C‐16 was fractured, after which a hydrogen atom was transferred from C‐14 to the carbonyl of C‐16 and McLafferty rearrangement occurred with the removal of a molecule of acetone.…”

Section: Resultsmentioning

confidence: 99%

Tandem Solid-Phase Extraction Followed by HPLC-ESI/QTOF/MS/MS for Rapid Screening and Structural Identification of Trace Diterpenoids in Flowers of Rhododendron molle

Hongyan

Luo

et al. 2014

Phytochem. Anal.

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“…Grayanotoxins have been analyzed in plant material and honey by direct spectrometric methods (Terai, 1983), by gas chromatography (GC) as the trimethylsilane (TMS) derivative (Terai et al, 1994), and by TLC (Terai, 1984;Kinghorn et al, 1978;Sutlupinar et al, 1993;Kerkvliet, 1981). Rhododendron maximum has been reported to contain >50 µg/g of both grayanotoxins I and III (Jawad et al, 1977).…”

Section: Introductionmentioning

confidence: 99%

Multiresidue Screen for Cardiotoxins by Two-Dimensional Thin-Layer Chromatography

Holstege

Francis

Puschner

et al. 1999

J. Agric. Food Chem.

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A two-dimensional thin-layer chromatographic method was developed for the qualitative determination of the cardiotoxins oleandrin, gitoxin, digitoxin, gitoxigenin, and grayanotoxins I, II, and III in gastrointestinal contents (stomach, rumen, colon, and cecum contents), feces, and plant material. The cardiotoxins were extracted with dichloromethane. The extract was cleaned up by charcoal and reverse phase solid-phase extraction columns. Analysis was performed by two-dimensional thin-layer chromatography on silica gel plates and visualized by aluminum chloride followed by chloramine T spray. The method detection limits were 0.05 microg/g for oleandrin, 0.1 microg/g for gitoxin, and 0.2 microg/g for the other toxicants in gastrointestinal contents and feces and were 5 times higher in plant material. Four replicate fortifications of bovine rumen contents, bovine feces, and alfalfa at these levels were all well recovered. The diagnostic utility of the method was tested by analyzing samples submitted to the veterinary toxicology laboratory.

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Characterization and mass spectral analysis of some grayanotoxin derivatives

Cited by 8 publications

References 9 publications

Determination of Grayanotoxins in Biological Samples by LC-MS/MS

Determination of Grayanotoxins in Biological Samples by LC-MS/MS

Tandem Solid-Phase Extraction Followed by HPLC-ESI/QTOF/MS/MS for Rapid Screening and Structural Identification of Trace Diterpenoids in Flowers of Rhododendron molle

Multiresidue Screen for Cardiotoxins by Two-Dimensional Thin-Layer Chromatography

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