Iso-lycopsamine, a pyrrolizidine alkaloid from Heliotropium keralense

Ravi, Subban; Lakshmanan, A. J.; Herz, Werner

doi:10.1016/0031-9422(90)89080-s

Cited by 19 publications

(7 citation statements)

References 8 publications

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“…Lindelofine [27], Supinine [27][28][29][30], Lycopsamine [30][31][32], Intermedin [30][31][32], Amabaline [28,33], Echinatine [28][29][30]32,33], Rinderine [28], Viridiflorine [28], Cynaustraline [28], Tussilagine [34] Heliotropium (Boraginaceae) Trachelanthamine [35,36], Floridine [35], Heliovicine [35], Lycopsamine [37,38], Intermedin [38], Amabiline [37], Curassavine [37,39], Heliospathine [37], Europine [40][41][42][43], Liamin [40], Heliotrine [42][43][44][45], Lasiocarpine [42,45,46], Retronecine [38,[47][48][49], Helibr...…”

Section: Genus Identified Pasmentioning

confidence: 99%

“…Methanol [36,37,39,45,46,132], Ethanol [35,38,43,[133][134][135], Methanol/Water/Formic Acid (25/23/2) [125] Percolation Methanol [40][41][42], Ethanol [39,47,49,136] Refluxing Methanol [137] Lithospermum (Boraginaceae)…”

Section: Macerationmentioning

confidence: 99%

“…Only a few extraction approaches (see Table 3) for PAs inherent in Helitropium species (see Table 2) were conducted. Methanol or either ethanol are used mostly for percolation [39][40][41][42]47,48,136] or maceration [35][36][37][38]43,45,46,[132][133][134][135]. These et al achieved, again, good results by the usage of a mixture of methanol and formic acid for maceration [125].…”

Section: Heliotropiummentioning

confidence: 99%

“…Most research groups were mainly interested in elucidating PA structures by applying 1 H-NMR, 13 C-NMR and MS [33,[35][36][37][38][39][40][41][42][43][44][46][47][48][49][132][133][134]136]. If quantified (see Table 4), the focus was set on determination of PA levels in young and matured leaves [135] or in elucidating different seasonal or environmental patterns [45].…”

Section: Heliotropiummentioning

confidence: 99%

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Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

Kopp

Abdel‐Tawab

Mizaikoff

2020

Toxins

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Pyrrolizidine alkaloids (PAs) are distributed in plant families of Asteraceae, Boraginaceae, and Fabaceae and serve in the chemical defense mechanism against herbivores. However, they became a matter of concern due to their toxicity associated with the high risk of intake within herbal preparations, e.g., phytopharmaceutical formulations, medicinal teas, or other plant-derived drug products. In 1992, the German Federal Ministry of Health established the first limits of PA content for fourteen medicinal plants. Because of the toxic effects of PAs, the Federal Institute of Risk Assessment (BfR) established more stringent limits in 2011, whereby a daily intake <0.007 µg/kg body weight was recommended and valid until 2018. A threefold higher limit was then advised by BfR. To address consumer safety, there is the need for more efficient extraction procedures along with robust, selective, and sensitive analytical methods to address these concerns. With the increased prevalence of, e.g., phytopharmaceutical formulations, this timely review comprehensively focuses on the most relevant extraction and analysis strategies for each of those fourteen plant genera. While a variety of extraction procedures has been reported, differences in PA content of up to 1110 ppm (0.11% (w/w)) were obtained dependent on the nature of the solvent and the applied extraction technique. It is evident that the efficient extraction of PAs requires further improvements or at least standardization of the extraction conditions. Comparing the various analytical techniques applied regarding selectivity and sensitivity, LC-MS methods appear most suited. This review shows that both standardized extraction and sensitive determination of PAs is required for achieving appropriate safety levels concerning public health in future.

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Section: Genus Identified Pasmentioning

confidence: 99%

Section: Macerationmentioning

confidence: 99%

Section: Heliotropiummentioning

confidence: 99%

Section: Heliotropiummentioning

confidence: 99%

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Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

Kopp

Abdel‐Tawab

Mizaikoff

2020

Toxins

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“…[1][2][3] These metabolites have been isolated from a wide variety of plants, especially from genera belonging to the Boraginaceae family. [4][5][6] The genus Heliotropium, a well-known source of such alkaloids [7][8][9] and other minor compounds, such as flavonoids and geranyl aromatic derivatives, is constituted of about 250 species represented by herbs and shrubs, distributed throughout the terrestrial globe. 10 In the course of a search for novel and biologically active compounds from plants the EtOH extract from the roots of Heliotropium indicum L., popularly known as fedegoso, found abundantly in the region of northeast Brazil, was investigated.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolizidine alkaloids from Heliotropium indicum

Souza¹,

Machado²,

Pessoa³

et al. 2005

J. Braz. Chem. Soc.

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Um novo alcalóide denominado Helindicina (1), e o conhecido licopsamina (2) foram isolados das raízes de Heliotropium indicum (Boraginaceae). As estruturas foram estabelecidas tendo como base um amplo estudo de 1D e 2D RMN (COSY, HMBC, HMQC, NOESY) e HREIMS. Este representa o primeiro relato de um alcalóide contendo um anel lacônico no gênero Heliotropium. Estes alcalóides mostraram moderada atividade antioxidante.Helindicine (1), a new pyrrolizidine alkaloid with unusual structural features, together with the known lycopsamine (2), were isolated from the roots of Heliotropium indicum (Boraginaceae). The structures were established by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and NOESY) and HREIMS. This is the first report of a lactone pyrrolizidine alkaloid in the genus Heliotropium. Compounds 1 and 2 were assayed for antioxidant activity and showed moderate activity.

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Heliotropium Species

2020

Secondary Metabolites of Medicinal Plants

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Iso-lycopsamine, a pyrrolizidine alkaloid from Heliotropium keralense

Cited by 19 publications

References 8 publications

Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

Pyrrolizidine alkaloids from Heliotropium indicum

Heliotropium Species

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