Pyrrolizidine alkaloids in two endemic capeverdian Echium species

Carvalho, José Carlos Borges de; Almeida, Henrique dos Santos; Lobo, Jonathas Felipe Revoredo; Ferreira, José Luiz P.; Oliveira, Adriana Passos; Rocha, Leandro

doi:10.1016/j.bse.2013.03.026

Cited by 15 publications

(8 citation statements)

References 19 publications

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“…Most of the detected compounds (peaks 1, 3, 5, 6, 9, 10, 12, 16, 17) were previously found in E. vulgare [12,23,27,28] . Several compounds (peaks 7, 8, 13, 14, 19–21) were detected for the first time in our work E. vulgare , but they have been previously found in other Boraginaceae species [29–32] …”

Section: Resultssupporting

confidence: 50%

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Stefova

Cvetanoska

Bogdanov

et al. 2022

Chemistry & Biodiversity

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Systematic study of extraction efficiency of pyrrolizidine alkaloids (PAs) and corresponding pyrrolizidine alkaloid N‐oxides (PANOs) from plant material for subsequent LC/MS analysis was carried out. The optimal extraction was achieved with methanol and one clean up step using SPE C18 column. With the optimized LC‐ESI‐MS/MS method using ion trap, the distribution and diversity of PAs and PANOs in plant material (leaves, flowers and stems) obtained from wild‐growing E. vulgare, E. italicum, S. officinale L., C. creticum and O. heterophylla species from Macedonia was assessed. These widespread Boraginaceae species contain various PAs and PANOs and 25 of them were identified. Based on these qualitative and quantitative analyses, the profiles of 1,2‐unsaturated PAs for each sample were obtained and their toxic potential was estimated. The toxic potential of O. heterophylla and C. creticum were assumed to be highest (containing up to 4753 mg/kg and 3507 mg/kg), followed by E. vulgare (up to 1340 mg/kg), S. officinale L. (up to 479 mg/kg) and E. italicum (up to 16 mg/kg). This method can be used for monitoring the inclusion of these secondary metabolites in the food chain in order to contribute in their risk management.

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Section: Resultssupporting

confidence: 50%

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Stefova

Cvetanoska

Bogdanov

et al. 2022

Chemistry & Biodiversity

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“…[91] Echimidine, echihumiline, 7-(2-methylbutyryl)-9-echimidinylretronecine, 7-senecioylretronecine, 9-angeloylretronecine, lycopsamine, 7-acetyl-lycopsamine [92] E. italicum…”

Section: ] E Horridummentioning

confidence: 99%

“…stenosiphon Echimidine, 7-(2-methylbutyryl)-9-echimidinylretronecine [92] E. tuberculatum Echimidine,7-angeloyl-9-viridiflorylretronecine, 7-viridiflorylretronecine.…”

Section: ] E Horridummentioning

confidence: 99%

“…PAs of about 15 species from this genus have been investigated which accumulate PAs from retronecine type [11,28,29,60,87,[89][90][91][92][93]96,99]. However, in earlier papers [47,97,98], the structure of major compounds in Echium vulgare were wrongly assigned to heliosupine and 3'-acetylheliosupine by means of paper chromatography and/or mass spectrometry.…”

Section: Genus Echiummentioning

confidence: 99%

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Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

2014

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Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs) are common in Boraginaceae, Asteraceae and some other plant families. Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans. Almost all genera of the family Boraginaceae synthesize and store this type of alkaloids. This review reports the available information on the present status (literature up to early 2014) of the pyrrolizidine alkaloids in the Boraginaceae and summarizes the topics structure, distribution, chemistry, chemotaxonomic significance, and biological properties.

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“…The MS 2 spectra of all analyzed monoesters and their N-oxides are presented in Figure 4. Lycospamine (3) was found in extracts of E. vulgare L. and S. officinale L., and rinderine (1) and echinatine (5) were found in extracts of C. creticum Mill., whereas heliotrine (7) was detected in E. vulgare L. In the literature, lycospamine (3) was also found in E. vulgare L., E. hupertropicum L., E. plantagineum, and S. officinale L., [23][24][25] rinderine (1) was found in C. officinale L., 25 and echinatine (5) was found in C. officinale L. and S. officinale L., 25 whereas heliotrine (7) was not previously detected in the Boraginacae species.…”

Section: Macrocyclic Diester N-oxide 30 20mentioning

confidence: 90%

Establishing mass spectral fragmentation patterns for characterization of 1,2 -unsaturated pyrrolizidine alkaloids and N-oxides in Boraginaceae species from Macedonia using LC-ESI-MS/MS

Станоева

Stefova

Cvetanoska

et al. 2022

Maced. J. Chem. Chem. Eng.

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Pyrrolizidine alkaloids (PAs) are secondary plant metabolites, and their 1,2-unsaturated derivatives, which contain the retronecine, heliotridine, or otonecine type of the necine base, have raised concern due to their ability to form hepatotoxic intermediates and exhibit serious toxic effects. Several hundred individual pyrrolizidine alkaloids and their N-oxides have been identified mostly using liquid chromatography coupled with mass spectrometry, although the number of available reference standards is limited. In this work, characteristic fragment ions and their abundance in the mass spectra of different PAs were used to reveal typical fragmentation patterns for various classes of PAs that can be further employed to distinguish monoesters (retronecine, heliotridine type), open chain diesters and macrocyclic diesters, and corresponding N-oxides. Fragment ions at m/z 120 and 138 were found in all types of PAs with a different relative abundance. Additional observation of fragment ions at m/z 94 and 156 was found to be typical for monoester PAs esterified at position C9 of the necin base, whereas fragment ions at m/z 111 and 172 were characteristic for monoester N-oxides. Fragment ions at m/z 180 and 220 were found to be typical for open chain diesters with esterification at C7 with acetic and angelic acid, respectively, whereas fragment ions at m/z 214 and 254 were characteristic for the respective N-oxides. For the 3ʹ-acetyl PA monoester or open chain diester derivatives, characteristic fragment ions were observed after loss of the acetyl moiety ([M+H]+–60), whereas for macrocyclic diesters and their N-oxides, fragment ions due to the neutral loss of CO were found ([M+H]+–28).

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Pyrrolizidine alkaloids in two endemic capeverdian Echium species

Cited by 15 publications

References 19 publications

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

Establishing mass spectral fragmentation patterns for characterization of 1,2 -unsaturated pyrrolizidine alkaloids and N-oxides in Boraginaceae species from Macedonia using LC-ESI-MS/MS

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