Structural and quantitative analysis of Equisetum alkaloids

Cramer, Luise; Ernst, Ludger; Lubienski, Marcus; Papke, Uli; Schiebel, Hans‐Martin; Jerz, Gerold; Beuerle, Till

doi:10.1016/j.phytochem.2015.03.003

Cited by 26 publications

(48 citation statements)

References 19 publications

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“…These Equisetum specific alkaloids show high structural similarity to Cannabisativines isolated from Cannabis sativa . However, as we were able to show recently, the postulated 18‐deoxypalustrine is in fact palustridiene, the open chain derivative of palustrine (biosynthetically up‐stream of palustrine) . So far we have detected and postulated some other minor Equisetum specific alkaloids which could be further sub‐grouped into the closely related palustrine‐ and palustridiene‐type alkaloids .…”

Section: Introductionsupporting

confidence: 49%

“…Figure summarises the structures of the known and postulated alkaloids recently identified from E. palustre . These alkaloids could be grouped into piperidine type Equisetum alkaloids and nicotine (pyridine‐pyrrolidine type alkaloid).…”

Section: Introductionmentioning

confidence: 99%

“…Structures and classification of alkaloids detected in Equisetum palustre , according to Cramer et al Unknown but analytically covered Equisetum alkaloids are given in short form of their nominal mass, e.g. M 323…”

Section: Introductionmentioning

confidence: 99%

“…No data is available for the class of spermidine derived piperidine alkaloids ( Equisetum alkaloids) palustrine and its recently discovered open chain analogue palustridiene . The occurrence of the Equisetum alkaloids has been recognised since the early twentieth century and is associated with negative health effects on livestock feeding on E. palustre .…”

Section: Introductionmentioning

confidence: 99%

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HILIC HPLC‐ESI‐MS/MS identification and quantification of the alkaloids from the genus Equisetum

Tipke

Bücker

Middelstaedt

et al. 2019

Phytochemical Analysis

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Introduction The plant family Equisetaceae (Equisetopsida, Monilophyta; common name: horsetails) is part of an ancient group of spore producing plants. Today, Equisetum is the only surviving genus comprising 15 species in two subgenera (Equisetum and Hippochaete). Several unique alkaloids are described to occur in this genus, so far there is very little data on the occurrence and the amount of those alkaloids for the different species. Objective To establish an extraction method and an analytical method to detect and quantify the relevant Equisetum‐type alkaloids and to create a quantitative data set on the alkaloid content of all Equisetum species worldwide. Methodology Hydrophilic interaction liquid chromatography high‐performance liquid chromatography tandem mass spectrometry (HILIC HPLC‐MS/MS) in electrospray ionisation (ESI) positive mode was used to analyse and quantify the alkaloid content of 68 Equisetum samples. Results The presence of nicotine in at least one sample of each Equisetum species could be demonstrated. The total nicotine amount rarely exceeded 250 μg/kg and 50 μg/kg for the subgenus Equisetum and Hippochaete, respectively. Besides nicotine, Equisetum‐type alkaloids (mainly palustrine and palustridiene) were only detected in three species, namely E. palustre, E. bogotense and E. giganteum. For E. giganteum, palustridiene was detected at levels around the limit od detection (LoD) (25 μg/kg), whereas in E. palustre and E. bogotense, both alkaloids (palustrine and palustridiene) were detected at much higher levels (20–800 mg/kg). Conclusions All Equisetum species occurring worldwide were successfully subjected to a detailed qualitative and quantitative alkaloid analysis using a newly developed HILIC‐HPLC‐ESIpos‐MS/MS approach. The data set can be used to distinguish different Equisetum‐chemotypes.

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Section: Introductionsupporting

confidence: 49%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

HILIC HPLC‐ESI‐MS/MS identification and quantification of the alkaloids from the genus Equisetum

Tipke

Bücker

Middelstaedt

et al. 2019

Phytochemical Analysis

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“…effects(Cramer et al, 2015;Konishi and Ichijo, 1984;Meyer, 1989;Oliveira et al, 2007). It has been shown that horsetail contains a thiaminase, causing a thiamine deficiency in the case of a long-term use of its extracts or macerates, and also small amounts of piperidine alkaloids linked to the occurrence of the nicotine-like effects(Cramer et al, 2015;Oliveira et al, 2007).These alkaloids are, however, present in higher quantities in other species of genus Equisetum, for instance in E. palustre, which contains piperidine alkaloid palustrine (Figure 2)(Cramer et al, 2015).3.2 The Neurotoxin SwainsonineAstragalus spp.…”

mentioning

confidence: 99%