Distinguishing between toxic and non-toxic pyrrolizidine alkaloids and quantification by liquid chromatography–mass spectrometry

Rösemann, Gertruida M.; Botha, Charl P.; Eloff, Jacobus Nicolaas

doi:10.1016/j.phytol.2014.03.002

Cited by 10 publications

(9 citation statements)

References 6 publications

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“…Further work will be required to determine whether this hypothesis is correct. Additionally, not all PAs are toxic (Rösemann et al, 2014) or present in the every Senecio plant and this would require further investigation using chromatographic techniques.…”

Section: Discussionmentioning

confidence: 99%

Enhanced cutaneous wound healing by Senecio serratuloides ( Asteraceae/Compositae ) in a pig model

Gould

Penny

Patel

et al. 2015

South African Journal of Botany

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a b s t r a c tSenecio serratuloides (Asteraceae/Compositae) is a traditional herbal remedy used to treat skin wounds in South Africa. The plant contains hepatotoxic alkaloids and is responsible for the death of farm animals which have eaten the plant. Wound healing efficacy was determined by applying prepared plant material to deep partialthickness wounds on a pig model and healing was compared to controls over 16 days. Regrowth of the skin was monitored by measuring the increasing ratio of the epidermal thickness, relative to that of normal skin. The neo-epidermis of plant-treated wounds was significantly thicker on days 5 and 7 and was maximal on day 7, compared with day 9 for the controls. The pH of the treated wound surface was significantly lower than the controls on day 2. The presence of alkaloids was confirmed with Dragendorff's reagent on thin layer chromatography, but liver function enzymes were no different to that of the controls and no signs of liver toxicity were apparent on histology when the plant was applied topically to wounds. S serratuloides treatment accelerated the healing of deep partial thickness wounds and the epidermal thickness ratio was found to be a useful marker in monitoring the wound healing process. The significance of the lower wound surface pH remains to be fully determined.

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Section: Discussionmentioning

confidence: 99%

Enhanced cutaneous wound healing by Senecio serratuloides ( Asteraceae/Compositae ) in a pig model

Gould

Penny

Patel

et al. 2015

South African Journal of Botany

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“…Pyrrolizidine alkaloids (PA) comprise several hundred compounds based on the heterocyclic two-ring structure necine 16 , 35 , 36 (Fig. 1 ).…”

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confidence: 99%

The invasive butterbur contaminates stream and seepage water in groundwater wells with toxic pyrrolizidine alkaloids

Kisielius

Hama

Skrbic

et al. 2020

Sci Rep

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Pyrrolizidine alkaloids (PAs) are persistent mutagenic and carcinogenic compounds produced by many common plant species. Health authorities recommend minimising human exposure via food and medicinal products to ensure consumer health and safety. However, there is little awareness that PAs can contaminate water resources. Therefore, no regulations exist to limit PAs in drinking water. This study measured a PA base concentration of ~ 70 ng/L in stream water adjacent to an invasive PA-producing plant Petasites hybridus (Asteraceae). After intense rain the PA concentration increased tenfold. In addition, PAs measured up to 230 ng/L in seepage water from groundwater wells. The dominant PAs in both water types corresponded to the most abundant PAs in the plants (senkirkine, senecionine, senecionine N-oxide). The study presents the first discovery of persistent plant toxins in well water and their associated risks. In addition, it for the first time reports monocrotaline and monocrotaline N-oxide in Petasites sp.

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“…Previous reports regarding the amount of monocrotaline in C. spectabilis seeds found 2.9% (29.0 mg/g) by GC technique, 10 and 3.2% (32.0 mg/g) by classic isolation and purification procedures, 23 which are in accordance with the results obtained in the present study (17.39 mg/g), being this the first quantification report of monocrotaline from C. spectabilis seeds and leaves obtained by HPLC‐MS/MS analysis, specifically coupled to an ion trap spectrometer. PAs have also been quantified by mass spectrometry in other Crotalaria species, such as leaves from C. dura (590 μg/g), 24 C. laburnifolia (20 μg/g) 24 and C. sessiflora (30 μg/g) 19 …”

Section: Resultsmentioning

confidence: 99%

Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC‐MS/MS dereplication and monocrotaline quantification of seed and leaf extracts

Scupinari

Mannochio-Russo

Ferrari

et al. 2020

Phytochemical Analysis

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Introduction: Crotalaria spectabilis is an important species used as a pre-plant cover for soybean crops to control the proliferation of endoparasitic nematodes. Species from the Crotalaria genus are known for presenting pyrrolizidine alkaloids (PAs) in their composition, however, C. spectabilis is still considered chemically underexplored. Objective: The goal of this manuscript is the development and validation of a method for PAs and flavonoids identification and quantification of C. spectabilis seeds and leaves, a toxic plant used for nematode proliferation control in soil, especially in soybean crops. Materials and methods: Seeds and leaves extracts were analysed by highperformance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS) for the identification of the compounds. Results: PAs and phenolic compounds could be identified in both samples based on the MS/MS fragmentation pattern. Molecular formulas of the annotated compounds were confirmed by ultra-high-performace liquid chromatography-quadrupole time-of-flight (UHPLC-QToF), and monocrotaline could also be confirmed by standard comparison. The quantification of monocrotaline was performed by HPLC-MS/MS, resulting in 123 times higher monocrotaline content in seeds than in the leaves, which could explain its efficiency in combating nematode proliferation in soil. Conclusion: This was the first report of phenolic compounds in C. spectabilis. The current study highlights the importance of C. spectabilis for nematode control due to the presence of toxic PAs, and the employment of analytical techniques for identification and quantification of compounds present in the extracts.

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Distinguishing between toxic and non-toxic pyrrolizidine alkaloids and quantification by liquid chromatography–mass spectrometry

Cited by 10 publications

References 6 publications

Enhanced cutaneous wound healing by Senecio serratuloides ( Asteraceae/Compositae ) in a pig model

Enhanced cutaneous wound healing by Senecio serratuloides ( Asteraceae/Compositae ) in a pig model

The invasive butterbur contaminates stream and seepage water in groundwater wells with toxic pyrrolizidine alkaloids

Crotalaria spectabilis as a source of pyrrolizidine alkaloids and phenolic compounds: HPLC‐MS/MS dereplication and monocrotaline quantification of seed and leaf extracts

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