1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae)

Seger, Christoph; Sturm, Sonja; Strasser, Eva-Maria; Ellmerer, Ernst P.; Stuppner, Hermann

doi:10.1002/mrc.1417

Cited by 46 publications

(31 citation statements)

References 27 publications

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“…The long range gHMBC correlation established the C→H and H→C cross-correlations among the H and C-atoms ( The other five known alkaloids were identified as protopine (2), norsanguinarine (3), dihydrosanguinarine (4), 6-methoxydihydrosanguinarine (5) and oxysanguinarine (6) ( C-NMR spectroscopic data agreed with those reported (Takahashi et al, 1985;Seger et al, 2004;Wangchuk et al, 2010). It was the major component of the plant.…”

Section: Separation/isolation Of Alkaloidssupporting

confidence: 83%

A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain

Wangchuk

Keller

Pyne

et al. 2013

Journal of Ethnopharmacology

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A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain AbstractEthnopharmacological relevance The aerial components of Meconopsis simplicifolia (D. Don) Walpers are indicated in Bhutanese traditional medicine for treating malaria, coughs and colds, and the infections of the liver, lung and blood. This study is to validate the ethnopharmacological uses of this plant and also identify potent antimalarial drug leads through bioassays of its crude extracts and phytochemical constituents.Materials and methods Meconopsis simplicifolia (D. Don) Walpers was collected from Bhutan and its crude MeOH extract was subjected to acid-base fractionation. Through repeated extractions, separations and spectroscopic analysis, the alkaloids obtained were identified and tested for their antimalarial and cytotoxicity activities.Results Phytochemical studies resulted in the isolation of one new protoberberine type alkaloid which we named as simplicifolianine and five known alkaloids: protopine, norsanguinarine, dihydrosanguinarine, 6-methoxydihydrosanguinarine and oxysanguinarine. Among the five of the alkaloids tested, simplicifolianine showed the most potent antiplasmodial activities against the Plasmodium falciparum strains, TM4/8.2 (chloroquine-antifolate sensitive strain) and K1CB1 (multidrug resistant strain) with IC50 values of 0.78 μg/ mL and 1.29 μg/mL, respectively. The compounds tested did not show any significant cytotoxicity activities against human oral carcinoma KB cells and normal Vero cells of African kidney epithelial cells.Conclusions This study validated the traditional uses of the plant for the treatment of malaria and identified a new alkaloid, simplicifolianine as a potential antimalarial drug lead.

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Section: Separation/isolation Of Alkaloidssupporting

confidence: 83%

A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain

Wangchuk

Keller

Pyne

et al. 2013

Journal of Ethnopharmacology

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“…C-NMR, and LC-IT TOF MS data with the literature values to be menisdaurin (1) (Seigler et al 2005), menisdaurilide (2) (Audran and Mori 1998), trans-N-p-coumaroyltyramine (3) (Kim et al 2014), trans-N-p-feruloyltyramine (4) (Choi et al 2016), 4-Oferuloylquinicacid (5) (Ge et al 2007), chlorogenic acid (6) (Han et al 2006), 3-O-feruloylquinicacid (7) (Ge et al 2007), ferulic acid (8) (Han et al 2006), protopine (9) (Seger et al 2004), Kaempferol 3,7-di-O-β-D-glucopyranoside (10) (Lee et al 2009 , α-rhamnoisorobin (12) (Cha and Lee 2007), astragalin (13) (Seo et al 2016), and nicotiflorin (14) (Tran et al 2014). Compound 1, 3-8, and 10-14 were reported for the first time from this plant.…”

supporting

confidence: 52%

Chemical constituents of Dicentra spectabilis and their anti-inflammation effect

Kim

Jang

Woo

et al. 2018

JABC

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Column chromatographic separation of the MeOH extract from the roots of Dicentra spectabilis yielded fourteen compounds, menisdaurin (1), menisdaurilide (2), trans-N-p- and nicotiflorin (14). Their structures were determined on the basis of NMR spectroscopic data. Among them, compound 1, 3-8, and 10-14 isolated from this plant were reported for the first time. The isolated compounds (1-14) were tested for nitric oxide (NO) inhibitory activity on lipopolysaccharide-stimulated RAW 264.7 cells. Compound 3, 4 and 12 significantly inhibited NO production. Moreover, Compound 3 suppressed pro-inflammatory cytokines (TNF-α, IL-1β and IL-6) in a dose-dependent manner. These data suggest that compound 3 possess anti-inflammatory activity and might be useful natural materials for development of anti-inflammatory agent.

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“…The available data indicate that G. parviflora contains fumaric acid (Mostafa, Abd El-Aziz, Hafez, & El-Shazly, 2013), essential oil (Mostafa et al, 2013;Pino et al, 2010), phytosterols (Mostafa et al, 2013;Tariq et al, 2008), mineral salts (Odhav, Beekrum, Akula, & Baijnath, 2007) and vitamins (Grubben & Denton, 2004), whereas F. officinalis fumaric and malic acids (Bradley, 1992;Ivanov et al, 2014;Soušek et al, 1999), isoquinoline alkaloids (Seger, Sturm, Strasser, Ellmerer, & Stuppner, 2004;Soušek et al, 1999;Sturm et al, 2006;Suau, Cabezudo, Rico, Nájera, & López-Romero, 2002) and indenobenzazepines (Bradley, 1992;Newall, Anderson, & Phillipson, 1996), as well as mucilage, resin, and bitter principles (Newall et al, 1996) have been identified.…”

Section: 3mentioning

confidence: 94%

Effects of plant extract antioxidative phenolic compounds on energetic status and viability of Saccharomyces cerevisiae cells undergoing oxidative stress

Chanaj-Kaczmarek

Wysocki

Karachitos

et al. 2015

Journal of Functional Foods

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¹H and ¹³C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae)

Cited by 46 publications

References 27 publications

A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain

A new protoberberine alkaloid from Meconopsis simplicifolia (D. Don) Walpers with potent antimalarial activity against a multidrug resistant Plasmodium falciparum strain

Chemical constituents of Dicentra spectabilis and their anti-inflammation effect

Effects of plant extract antioxidative phenolic compounds on energetic status and viability of Saccharomyces cerevisiae cells undergoing oxidative stress

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