Pyrrolizidine alkaloids and beehive products: A review

Brugnerotto, Patrícia; Seraglio, Siluana Katia Tischer; Schulz, Mayara; Gonzaga, Luciano Valdemiro; Fett, Roseane; Costa, Ana Carolina Oliveira

doi:10.1016/j.foodchem.2020.128384

Cited by 42 publications

(18 citation statements)

References 82 publications

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“…Most bee products, such as honey, bee pollen, propolis, and royal jelly, are consumed by humans in a belief in their health benefits, although evidence-based data in support of such beneficial properties are limited [ 26 , 27 ]. Better studied is the potential contamination of bee products with PAs; for example, by bees collecting material from flowering plants that contain PAs [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. However, of theoretical interest only are these abundant reports, because they focus primarily on the amount of PAs in bee products rather than on the issue of whether or not even high amounts of PAs are potentially dangerous to consumers, e.g., causing liver injury in the form of HSOS.…”

Section: Global Presence and Use Of Plants Containing Pasmentioning

confidence: 99%

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Teschke

Noudeng

Quan

et al. 2021

IJMS

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Saturated and unsaturated pyrrolizidine alkaloids (PAs) are present in more than 6000 plant species growing in countries all over the world. They have a typical heterocyclic structure in common, but differ in their potential toxicity, depending on the presence or absence of a double bond between C1 and C2. Fortunately, most plants contain saturated PAs without this double bond and are therefore not toxic for consumption by humans or animals. In a minority of plants, however, PAs with this double bond between C1 and C2 exhibit strong hepatotoxic, genotoxic, cytotoxic, neurotoxic, and tumorigenic potentials. If consumed in error and in large emouns, plants with 1,2-unsaturated PAs induce metabolic breaking-off of the double bonds of the unsaturated PAs, generating PA radicals that may trigger severe liver injury through a process involving microsomal P450 (CYP), with preference of its isoforms CYP 2A6, CYP 3A4, and CYP 3A5. This toxifying CYP-dependent conversion occurs primarily in the endoplasmic reticulum of the hepatocytes equivalent to the microsomal fraction. Toxified PAs injure the protein membranes of hepatocytes, and after passing their plasma membranes, more so the liver sinusoidal endothelial cells (LSECs), leading to life-threatening hepatic sinusoidal obstruction syndrome (HSOS). This injury is easily diagnosed by blood pyrrolizidine protein adducts, which are perfect diagnostic biomarkers, supporting causality evaluation using the updated RUCAM (Roussel Uclaf Causality Assessment Method). HSOS is clinically characterized by weight gain due to fluid accumulation (ascites, pleural effusion, and edema), and may lead to acute liver failure, liver transplantation, or death. In conclusion, plant-derived PAs with a double bond between C1 and C2 are potentially hepatotoxic after metabolic removal of the double bond, and may cause PA-HSOS with a potential lethal outcome, even if PA consumption is stopped.

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Section: Global Presence and Use Of Plants Containing Pasmentioning

confidence: 99%

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Teschke

Noudeng

Quan

et al. 2021

IJMS

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“…In Traditional Chinese Medicine, Senecio plants were applied for thousands of years. In the world, about 3%-5% of all flowering plants contain PAs, which are one of the most toxic constituents in plants and cause hepatotoxicity mainly with the major clinical symptom of veno-occlusive disease (VOD) and other toxicities such as neurotoxicity, genotoxicity, et al [1]. e mechanism of the toxicity of PAs is considered as metabolic activation; first, PAs was metabolized by P450 enzymes to generate dehydropyrrolizidine (DHP), then DHP with strong electrophilicity attacks proteins or DNA molecules to generate adducts, and finally, various signs of toxicity are induced [2].…”

Section: Introductionmentioning

confidence: 99%

Identification of Pyrrolizidine Alkaloids in Senecio Plants by Liquid Chromatography-Mass Spectrometry

Tan

et al. 2021

Journal of Analytical Methods in Chemistry

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Pyrrolizidine alkaloids (PAs) are considered as the major constituents that cause hepatoxicity in Senecio plants. PAs can be found in about 3%–5% of the world’s flowering plants. Nowadays, the identification method of PAs by separation and preparation was too slow and lacked effective power. A rapid method to identify PAs in plants must be developed. Based on the fragmentation regularity, the hepatoxic PAs and nonhepatoxic PAs were characterized by liquid chromatography-mass spectrometry (LC-MS). The detailed structures of PAs in five Senecio plants were identified based on tandem mass spectrometry (MS/MS) spectrum and chemical research information. In the present study, some new fragmentation regularities of PAs have been found, such as product ions at m/z 122, m/z 140 and m/z 124, m/z 142, which have been discovered as the characteristic fragments of lactone and mono-esterase type of saturated PAs, respectively. Moreover, two product ions at m/z 120 and m/z 138 have been reported as the characteristic fragments of unsaturated PAs. Some of them were found in Senecio species for the first time, and some of them may be new nature product or even new compound. Finally, we classified these plants into five categories based on PAs which were identified in the present study; the result corresponded with the classification by morphology. In addition, we have found some constituents that have odd molecular weight number only in Senecio species but not in Ligularia species; the detailed structures of these non-PAs constituents need penetrating study. LC-MS was rapid and sensitive method for detecting and identifying PAs in plants. Pyrrolizidine alkaloids were the toxiferous constituent of Senecio plants. In this study, we found that PAs can be used as the characteristic constituent of Senecio species.

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“…As ações de caracterização e monitoramento de plantas com potencial apícola também poderão auxiliar a comunidade científica e órgãos regulamentadores de alimentos em relação à presença de compostos químicos em produtos apícolas, como os alcaloides pirrolizidínicos (AP). Esses compostos são toxinas naturais produzidas por alguns gêneros de Asteraceae, Fabaceae e Boraginaceae (Bandini, et al, 2020) e são comumente encontrados em produtos apícolas, principalmente no mel e no pólen (Brugnerotto et al, 2021). Portanto, a presença de AP é considerada indesejável, principalmente se a soma desses compostos estiver acima de 71 µg kg -1 (EFSA, et al, 2017) em méis e 500 µg kg -1 em polens (European Commission, 2020).…”

Section: Resultsunclassified

Identificação de plantas com potencial apícola provenientes de sistemas de monitoramento de colmeias no estado de Santa Catarina, Brasil

Brugnerotto

Dortzbach

Blainski

et al. 2021

RSD

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A caracterização de espécies vegetais com potencial apícola presentes em sistemas de produção apícola pode trazer muitas vantagens. Entre os benefícios, destaca-se a definição do local de implantação das colmeias nos agroecossistemas de acordo com a disponibilidade de recursos florais, permitindo aumentar a produtividade e qualidade dos méis e demais produtos provenientes das abelhas. Nesse sentido, o objetivo desse trabalho foi coletar espécies de plantas com flores visitadas por abelhas próximas de sistemas de monitoramento de colmeias em seis zonas agroecológicas do estado de Santa Catarina, Brasil, bem como realizar a identificação taxonômica e geográfica destas espécies. Para cada amostra foi registrada sua localização, para estimar a distância do percurso realizado pelas abelhas, uma vez que a localização da colmeia era fixa. Nas 157 amostras identificadas, 81 espécies e 68 gêneros foram encontrados em 33 famílias, sendo Asteraceae e Fabaceae predominantes. Para Asteraceae, os gêneros mais relatados foram Baccharis, Tithonia, Senecio e Sphagneticola, enquanto para Fabaceae, o gênero mais relatado foi Trifolium. Espécies como Sphagneticola trilobata (Asteraceae), Trifolium repens, T. pratense, Cajanus cajan, Vicia sp. (todas Fabaceae), Verbena litoralis, Lantana undulata (ambas Verbenaceae), Raphanus sativus (Brassicaceae) e Clidemia hirta (Melastomataceae) podem ser consideradas interessantes do ponto de vista apícola, pois permaneceram com flores entre o primeiro e último dia de coleta em algumas regiões (~60 dias). Apesar das distâncias entre as plantas e as colmeias apresentarem elevada variabilidade (8 a 1154 m), geralmente as distâncias não ultrapassavam 750 m.

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Pyrrolizidine alkaloids and beehive products: A review

Cited by 42 publications

References 82 publications

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Metabolic Toxification of 1,2-Unsaturated Pyrrolizidine Alkaloids Causes Human Hepatic Sinusoidal Obstruction Syndrome: The Update

Identification of Pyrrolizidine Alkaloids in Senecio Plants by Liquid Chromatography-Mass Spectrometry

Identificação de plantas com potencial apícola provenientes de sistemas de monitoramento de colmeias no estado de Santa Catarina, Brasil

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