Heliscabine, a pyrrolizidine ester alkaloid from Heliotropium scabrum

Lakshmanan, A. J.; Shanmugasundaram, Singaram

doi:10.1016/0031-9422(94)00937-o

Cited by 12 publications

(5 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%

“…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%

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Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

Kopp

Abdel‐Tawab

Mizaikoff

2020

Toxins

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“…Saponification of both esters led to a new necine base, helibracteatinecine ( 16c ), a diastereoisomer of 15b . The same year, the authors also reported the isolation of heliscabine ( 15a ) (9‐angelyl helibractenecine) from Heliotropium scabrum , an herb distributed in the foothills of peninsular India and also in Sri Lanka …”

Section: Natural Occurrence Of C‐branched Imino Sugarsmentioning

confidence: 93%

C‐Branched Imino Sugars: Synthesis and Biological Relevance

Dehoux

Génisson

2019

Eur J Org Chem

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Only few naturally occurring pyrrolizidine imino sugars possess a geminal‐hydroxyhydroxymethyl group. In search for more potent and selective inhibitors of carbohydrate processing enzymes, organic chemists took inspiration from this uncommon feature. The presence of such a group formally results from either i) a shift of the hydroxymethyl group of the imino sugar toward an adjacent hydroxylated position or ii) the addition of a second hydroxymethyl group on a tertiary alcohol. Five‐, six‐, seven‐membered ring imino sugars and bicyclic imino sugars embedding this structural feature were thus prepared by innovative synthetic strategies. Some of these derivatives are very potent and selective inhibitors of glycosidases. Moreover, several C‐branched imino sugars proved recently to act as corrector of F508del‐CTFR and open the way for the development of derivatives relevant in the context of cystic fibrosis.

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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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Heliscabine, a pyrrolizidine ester alkaloid from Heliotropium scabrum

Cited by 12 publications

References 8 publications

Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

Extracting and Analyzing Pyrrolizidine Alkaloids in Medicinal Plants: A Review

C‐Branched Imino Sugars: Synthesis and Biological Relevance

Pyrrolizidine alkaloids from Heliotropium indicum

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