Spatial and Temporal Distribution of the Alkaloid Sanguinarine in Sanguinaria canadensis L. (Bloodroot)

Campbell, Selima Makeba; Affolter, James M.; Randle, William M.

doi:10.1663/0013-0001(2007)61[223:satdot]2.0.co;2

Cited by 12 publications

(15 citation statements)

References 16 publications

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“…This was a key consideration as BIA content can vary considerably in different organs. For example, sanguinarine in Sanguinaria canadensis occurs at concentrations ten- and one thousand-fold lower in roots and aerial organs (leaves, flowers), respectively, compared with the accumulation in rhizomes [ 8 ]. Plant-specific circumstances (e.g.…”

Section: Resultsmentioning

confidence: 99%

Metabolome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants

et al. 2015

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BackgroundRecent progress toward the elucidation of benzylisoquinoline alkaloid (BIA) metabolism has focused on a small number of model plant species. Current understanding of BIA metabolism in plants such as opium poppy, which accumulates important pharmacological agents such as codeine and morphine, has relied on a combination of genomics and metabolomics to facilitate gene discovery. Metabolomics studies provide important insight into the primary biochemical networks underpinning specialized metabolism, and serve as a key resource for metabolic engineering, gene discovery, and elucidation of governing regulatory mechanisms. Beyond model plants, few broad-scope metabolomics reports are available for the vast number of plant species known to produce an estimated 2500 structurally diverse BIAs, many of which exhibit promising medicinal properties.ResultsWe applied a multi-platform approach incorporating four different analytical methods to examine 20 non-model, BIA-accumulating plant species. Plants representing four families in the Ranunculales were chosen based on reported BIA content, taxonomic distribution and importance in modern/traditional medicine. One-dimensional 1H NMR-based profiling quantified 91 metabolites and revealed significant species- and tissue-specific variation in sugar, amino acid and organic acid content. Mono- and disaccharide sugars were generally lower in roots and rhizomes compared with stems, and a variety of metabolites distinguished callus tissue from intact plant organs. Direct flow infusion tandem mass spectrometry provided a broad survey of 110 lipid derivatives including phosphatidylcholines and acylcarnitines, and high-performance liquid chromatography coupled with UV detection quantified 15 phenolic compounds including flavonoids, benzoic acid derivatives and hydroxycinnamic acids. Ultra-performance liquid chromatography coupled with high-resolution Fourier transform mass spectrometry generated extensive mass lists for all species, which were mined for metabolites putatively corresponding to BIAs. Different alkaloids profiles, including both ubiquitous and potentially rare compounds, were observed.ConclusionsExtensive metabolite profiling combining multiple analytical platforms enabled a more complete picture of overall metabolism occurring in selected plant species. This study represents the first time a metabolomics approach has been applied to most of these species, despite their importance in modern and traditional medicine. Coupled with genomics data, these metabolomics resources serve as a key resource for the investigation of BIA biosynthesis in non-model plant species.Electronic supplementary materialThe online version of this article (doi:10.1186/s12870-015-0594-2) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Metabolome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants

et al. 2015

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“…The distribution of sanguinarine in different S. canadensis tissues is shown in Figure 2 [ 90 ]. Sanguinarine has its greatest concentration in the plants rhizome, followed by the roots, with minimal concentrations present in the leaves and flowers.…”

Section: Phytochemicals In S Canadensismentioning

confidence: 99%

Sanguinaria canadensis: Traditional Medicine, Phytochemical Composition, Biological Activities and Current Uses

Croaker

King

Pyne

et al. 2016

IJMS

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Sanguinaria canadensis, also known as bloodroot, is a traditional medicine used by Native Americans to treat a diverse range of clinical conditions. The plants rhizome contains several alkaloids that individually target multiple molecular processes. These bioactive compounds, mechanistically correlate with the plant’s history of ethnobotanical use. Despite their identification over 50 years ago, the alkaloids of S. canadensis have not been developed into successful therapeutic agents. Instead, they have been associated with clinical toxicities ranging from mouthwash induced leukoplakia to cancer salve necrosis and treatment failure. This review explores the historical use of S. canadensis, the molecular actions of the benzophenanthridine and protopin alkaloids it contains, and explores natural alkaloid variation as a possible rationale for the inconsistent efficacy and toxicities encountered by S. canadensis therapies. Current veterinary and medicinal uses of the plant are studied with an assessment of obstacles to the pharmaceutical development of S. canadensis alkaloid based therapeutics.

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“…1) is a natural plant alkaloid abundantly distributed in the plants like Sanguinaria canadensis and Chelidonium majus. [1][2][3][4][5] Sanguinarine has been the focus of extensive research for its potential drug value. In recent years considerable research on its antimicrobial, antifungal, antioxidant and anti-inammatory effects, [6][7][8][9][10] and ability for selective/ preferential elimination of cancer cells has been undertaken.…”

Section: Introductionmentioning

confidence: 99%

Physicochemical properties of inclusion complexes of sanguinarine with natural cyclodextrins: spectroscopy, calorimetry and NMR studies

Hazra

Kumar

2015

RSC Adv.

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The supramolecular interactions for the formation of inclusion complexes of sanguinarine with a-, b-, and g-cyclodextrins (CDs) were studied by UV-vis absorbance, fluorescence, circular dichroism and proton nuclear magnetic resonance spectroscopy, and isothermal titration calorimetry. The results revealed that sanguinarine binds with the three natural CDs in 1 : 1 stoichiometry. The binding affinity followed the order b > a > g-CDs; the affinity to b-CD was the highest compared to the other two CDs apparently due to the perfect cavity size for the inclusion of sanguinarine into the b-CD cavity. The association of sanguinarine with a-, and b-CDs is synergistically driven by a greater entropy contribution to the Gibbs energy of the association, whereas it was favoured by both enthalpy and entropy contributions for the g-CD. The NMR study indicated that encapsulation of sanguinarine in a-, and b-CDs, involves partial inclusion and to g-CD it is non-specific and complete inclusion i.e., both ends of sanguinarine, can be included into the CD cavity.

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Spatial and Temporal Distribution of the Alkaloid Sanguinarine in Sanguinaria canadensis L. (Bloodroot)

Cited by 12 publications

References 16 publications

Metabolome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants

Metabolome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants

Sanguinaria canadensis: Traditional Medicine, Phytochemical Composition, Biological Activities and Current Uses

Physicochemical properties of inclusion complexes of sanguinarine with natural cyclodextrins: spectroscopy, calorimetry and NMR studies

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