Pyrrolizidine alkaloids in medicinal tea of Ageratum conyzoides

Bosi, Cristiane F.; Rosa, Daniela W.; Grougnet, Raphaë͏l; Lemonakis, Nikolaos; Halabalaki, Maria; Skaltsounis, Alexios Léandros; Biavatti, Maique W.

doi:10.1590/s0102-695x2013005000028

Cited by 55 publications

(27 citation statements)

References 17 publications

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“…Alkaloids were not detected by the method used. Others genera of Asteraceae are known by the presence of alkaloids, such as Ageratum and Senecio (Paiva et al 2004, Bosi et al 2013. Reducing sugars were also described in Asteraceae (Ribeiro et al 2010).…”

Section: Discussionmentioning

confidence: 99%

Anatomical, phytochemical and histochemical study of Solidago chilensis Meyen

Souza

Sá

Araújo³

et al. 2018

An. Acad. Bras. Ciênc.

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Solidago chilensis Meyen, belonging to the family Asteraceae, is a plant native to South America and the only representative of the genus in Brazil. This species is popularly known as "arnica" and is used to treat bruises, muscle pain and inflammation. The objective of this work was to contribute to the pharmacognostic standardization of S. chilensis. Cross-sections were obtained, by freehand, for microscopic analysis of root, stem and leaf; for these parts of the plant maceration was also performed according to the method of Jeffrey. For the leaf were still made paradermal sections, scanning electron microscopy analysis, phytochemical and histochemical tests. Thus, it was determined anatomical features useful for diagnosis of the species which, together with identification of the chemical compounds and its histolocalization, provides support to their quality control.

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Section: Discussionmentioning

confidence: 99%

Anatomical, phytochemical and histochemical study of Solidago chilensis Meyen

Souza

Sá

Araújo³

et al. 2018

An. Acad. Bras. Ciênc.

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“…Ageratum conyzoides for example has been reported to contain lycopsamine (3) and echinatine [41,42] or lycopsamine (3) and 3 -O-acetyllycopsamine [43]. A targeted screen by Avula reported lycopsamine (3) and its N-oxide (6) as the two major PAs, together with minor amounts of dihydrolycopsamine, dihydrolycopsamine N-oxide and echinatine [1,44]. The closely related Ageratum houstonianum is locally abundant in Queensland, and our analysis of Zn reduced plant extract revealed the predominance of retrohoustine, heliohoustine and tentatively echinatine (ratio 2.7:1.7:1 respectively), with much lower amounts of lycopsamine (3) and intermedine (1) (data not shown).…”

Section: Plant Sources Of Lycopsamine (3) In Honeymentioning

confidence: 99%

Analysis of Pyrrolizidine Alkaloids in Queensland Honey: Using Low Temperature Chromatography to Resolve Stereoisomers and Identify Botanical Sources by UHPLC-MS/MS

Hungerford

Carter

Anuj

et al. 2019

Toxins

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Pyrrolizidine alkaloids (PAs) are a diverse group of plant secondary metabolites with known varied toxicity. Consumption of 1,2-unsaturated PAs has been linked to acute and chronic liver damage, carcinogenicity and death, in livestock and humans, making their presence in food of concern to food regulators in Australia and internationally. In this survey, honey samples sourced from markets and shops in Queensland (Australia), were analysed by high-resolution Orbitrap UHPLC-MS/MS for 30 common PAs. Relationships between the occurrence of pyrrolizidine alkaloids and the botanical origin of the honey are essential as pyrrolizidine alkaloid contamination at up to 3300 ng/g were detected. In this study, the predominant alkaloids detected were isomeric PAs, lycopsamine, indicine and intermedine, exhibiting identical MS/MS spectra, along with lesser amounts of each of their N-oxides. Crucially, chromatographic UHPLC conditions were optimised by operation at low temperature (5 • C) to resolve these key isomeric PAs. Such separation of these isomers by UHPLC, enabled the relative proportions of these PAs present in honey to be compared to alkaloid levels in suspect source plants. Overall plant pyrrolizidine alkaloid profiles were compared to those found in honey samples to help identify the most important plants responsible for honey contamination. The native Australian vines of Parsonsia spp. are proposed as a likely contributor to high levels of lycopsamine in many of the honeys surveyed. Botanical origin information such as this, gained via low temperature chromatographic resolution of isomeric PAs, will be very valuable in identifying region of origin for honey samples. Key Contribution:This study demonstrated the occurrence of indicine and the isomeric lycopsamine as predominant pyrrolizidine alkaloids in Australian honey; and established a HRAM LC-MS/MS method that chromatographically separated these stereoisomers; enabling the investigation of botanical origin of honey contamination by the respective alkaloids.

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“…Therefore, the positive identification and source of all plants that are currently sold for the preparation of asmachilca were outside the scope of this current work. As demonstrated by others (BfR, 2013; Bosi et al, 2013; Bodi et al, 2014), the potential for adverse health consequences due to the presence of dehydroPAs in herbal teas, at concentrations that violate regulatory limits for these compounds in materials intended for human consumption, justifies this approach. Several available records (e.g., IICT, 2015) state that asmachilca is made of Eupatorium gayanum Wedd.…”

Section: Resultsmentioning

confidence: 94%

Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine “asmachilca”

Colegate

Boppré

Monzon

et al. 2015

Journal of Ethnopharmacology

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Ethnopharmacological relevance Asmachilca is a Peruvian medicinal herb preparation ostensibly derived from Eupatorium gayanum Wedd. = Aristeguietia gayana (Wedd.) R.M. King & H. Rob. (Asteraceae: Eupatorieae). Decoctions of the plant have a reported bronchodilation effect that is purported to be useful in the treatment of respiratory allergies, common cold and bronchial asthma. However, its attractiveness to pyrrolizidine alkaloid-pharmacophagous insects indicated a potential for toxicity for human consumers. Aim of the study To determine if commercial asmachilca samples, including fully processed herbal teas, contain potentially toxic 1,2-dehydropyrrolizidine alkaloids. Materials and methods Two brands of “Asmachilca” herbal tea bags and four other commercial samples of botanical materials for preparing asmachilca medicine were extracted and analyzed using HPLC-esi(+)MS and MS/MS for the characteristic retention times and mass spectra of known dehydropyrrolizidine alkaloids. Other suspected dehydropyrrolizidine alkaloids were tentatively identified based on MS/MS profiles and high resolution molecular weight determinations. Further structure elucidation of isolated alkaloids was based on 1D and 2D NMR spectroscopy. Results Asmachilca attracted many species of moths which are known to pharmacophagously gather dehydropyrrolizidine alkaloids. Analysis of 5 of the asmachilca samples revealed the major presence of the dehydropyrrolizidine alkaloid monoesters rinderine and supinine, and their N-oxides. The 6th sample was very similar but did not contain supinine or its N-oxide. Small quantities of other dehydropyrrolizidine alkaloid monoesters, including echinatine and intermedine, were also detected. In addition, two major metabolites, previously undescribed, were isolated and identified as dehydropyrrolizidine alkaloid monoesters with two “head-to-tail” linked viridifloric and/or trachelanthic acids. Estimates of total pyrrolizidine alkaloid and N-oxide content in the botanical components of asmachilca varied from 0.4 – 0.9% (w/dw, dry weight) based on equivalents of lycopsamine. The mean pyrrolizidine alkaloid content of a hot water infusion of a commercial asmachilca herbal tea bag was 2.2 ± 0.5 mg lycopsamine equivalents. Morphological and chemical evidence showed that asmachilca is prepared from different plant species. Conclusions All asmachilca samples and the herbal tea infusions contained toxicologically-relevant concentrations of pro-toxic 1,2-dehydropyrrolizidine alkaloid esters and, therefore, present a risk to the health of humans. This raises questions concerning the ongoing unrestricted availability of such products on the Peruvian and international market. In addition to medical surveys of consumers of asmachilca, in the context of chronic disease potentially associated with ingestion of the dehydropyrrolizidine alkaloids, the botanical origins of asmachilca preparations require detailed elucidation.

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Pyrrolizidine alkaloids in medicinal tea of Ageratum conyzoides

Cited by 55 publications

References 17 publications

Anatomical, phytochemical and histochemical study of Solidago chilensis Meyen

Anatomical, phytochemical and histochemical study of Solidago chilensis Meyen

Analysis of Pyrrolizidine Alkaloids in Queensland Honey: Using Low Temperature Chromatography to Resolve Stereoisomers and Identify Botanical Sources by UHPLC-MS/MS

Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine “asmachilca”

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