Pyrrolizidine Alkaloids from <i>Onosma erecta</i>

Damianakos, H; Sotiroudis, Georgios; Chinou, İoanna

doi:10.1021/np300785g

Cited by 21 publications

(13 citation statements)

References 31 publications

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“…On the other hand, literature reported that aerial parts contain pyrrolizidine alkaloids (El-Shazly et al, 2003[10]; Damianakos et al, 2013[7]) and phenolic compounds (Mellidis et al, 1993[15]).…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem

Vukić

Vuković

Đelić

et al. 2017

EXCLI Journal; 16:Doc73; ISSN 1611-2156

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Section: Introductionmentioning

confidence: 99%

Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem

Vukić

Vuković

Đelić

et al. 2017

EXCLI Journal; 16:Doc73; ISSN 1611-2156

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“…Two 2,3-dihydroxy-2- iso -propylbutanoic acids units were identified for each alkaloid, similar to viridinatine ( 9 ) isomers isolated from Cynoglossum furcatum (Ravi et al, 2008) and Onosma erecta (Damianakos et al, 2013). However, instead of the C7 and C9 hydroxyls of the necine base each being esterified with a single butanoic acid unit, the two butanoic acid units were linked “head-to-tail” and esterified the C9 hydroxyl of the necine base.…”

Section: Resultsmentioning

confidence: 77%

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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“…This implies that onosmoleptine and leptanthine were thermally converted in the column to some of the identified PAs. From the free PAs extracted in the CH 2 Cl 2 layer ( Figure 5), only heliosupine was identified ( Figure 6) has been recently shown to contain the N-oxides of four PAs, namely 7-O-acetylechinatine, 7-epiechimiplatine, onosmerectine, and a stereoisomer of viridinatine (27). It is also reported that the latter two PAs undergo thermal decomposition in the column, and these alkaloids account for the 97.7% of unidentified PAs in the PA N-oxide extract of O. erecta ( Table 1).…”

Section: Gc/ms Analysismentioning

confidence: 99%

“…& Sm. have already been studied in our laboratory, leading to the isolation of their major PAs: leptantine N-oxide, onosmoleptine N-oxide, echihumiline N-oxide, 7-O-acetylechinatine N-oxide, onosmerectine N-oxide, 7-epiechimiplatine N-oxide, and one stereoisomer of viridinatine N-oxide (26,27). Reported here is additional investigation of the minor alkaloidal N-oxide or free PA (usually present in trace amounts) content of these species, along with the profiling of two additional, so far unstudied, endemic Greek Boraginaceae plants (Cynoglossum columnae L. and Onosma kaheirei Teppner).…”

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confidence: 99%

The Chemical Profile of Pyrrolizidine Alkaloids from Selected Greek Endemic Boraginaceae Plants Determined by Gas Chromatography/Mass Spectrometry

Damianakos

Jeziorek

Pietrosiuk

et al. 2014

Journal of AOAC INTERNATIONAL

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Four Greek endemic Boraginaceae plants, Onosma erecta Sibth. & Sm., Onosma kaheirei Teppner, Onosma leptantha Heldr., and Cynoglossum columnae L. (aerial parts), were screened for their content of pyrrolizidine alkaloids (PAs). TLC with the Mattocks-Molyneux visualization reagent was used as a preliminary qualitative test for PA or PA N-oxide detection. The extracts of the species found to contain PAs and their N-oxides were further analyzed by GC/MS, so as to identify their structures by means of the mass spectra and retention index values of known PAs already published in the literature. Twenty-three PAs were identified. For additional peaks, recognized as possible PAs by their MS pattern, no exact structures were tentatively suggested, as a result of lack of matching literature data. Furthermore, a quantitative PA profile of the species was obtained.

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Pyrrolizidine Alkaloids from Onosma erecta

Cited by 21 publications

References 31 publications

Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem

Antibacterial and cytotoxic activities of naphthoquinone pigments from Onosma visianii Clem

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

The Chemical Profile of Pyrrolizidine Alkaloids from Selected Greek Endemic Boraginaceae Plants Determined by Gas Chromatography/Mass Spectrometry

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