Antiplasmodial benzophenone derivatives from the root barks of Symphonia globulifera (Clusiaceae)

Marti, Guillaume; Éparvier, Véronique; Moretti, Christian; Prado, Soizic; Grellier, Philippe; Hue, Nathalie; Thoison, Odile; Delpech, Bernard; Guéritte, Françoise; Litaudon, Marc

doi:10.1016/j.phytochem.2010.03.008

Cited by 49 publications

(49 citation statements)

References 24 publications

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“…Considering the increased resistance of the parasites to the conventional antimalarial drugs (Dondorp et al, 2009;Marti et al, 2010), these findings are timely as they (Cho, 2001) and showed an inhibitory effect on the growth of human colon carcinoma cells and induced apoptosis (Lee et al, 2004). However, this compound exhibited no cytotoxicity against KB and Vero cells in our study at the highest concentration tested.…”

Section: Resultsmentioning

confidence: 49%

“…As an individual plant, it is indicated for treating coughs and colds, fever and infections in the liver, lung and blood which show correlations to the symptoms of cancer, microbial infections and malaria (Wangchuk et al, 2008(Wangchuk et al, , 2011. Malaria causes 2-3 million deaths each year (Marti et al, 2010). In Bhutan, there were 436 microscopy-confirmed indigenous cases with 140 (32%)…”

Section: Simplicifolia Is Locally Known As Ud-pel-sngon-po and Gromentioning

confidence: 99%

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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

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: Resultsmentioning

confidence: 49%

Section: Simplicifolia Is Locally Known As Ud-pel-sngon-po and Gromentioning

confidence: 99%

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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“…This compound was putatively identified as one of the guttiferone B (Gustafson et al, 1992) isomers (D 4.5 ppm), ie. guttiferone C, guttiferone D or symphonone B (Marti et al, 2010). Further observations of Fig.…”

Section: Resultsmentioning

confidence: 58%

“…During the last few years, an increasing number of phytochemical studies have been undertaken on the tropical tree Symphonia globulifera, illustrating the growing interest of the scientific community for this species (Lenta et al, 2007;Marti et al, 2010;Ngouela et al, 2006). S. globulifera L. f. (Clusiaceae) is usually found within humid mixed species forests and freshwater swamp forests of America and Africa (Budde et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

“…Locksley reported the isolation of xanthones from the heartwood (Locksley et al, 1966a,b), and although PPAPs are present in all of the different tissues, they were first isolated from the roots bark (Gustafson et al, 1992;Marti et al, 2010;Nkengfack et al, 2002). The seeds have also been studied unravelling the presence of guttiferone A (1) together with gaboxanthone (2), globuliferin (3) and symphonin (4) (Ngouela et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

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Comparative LC–MS-based metabolite profiling of the ancient tropical rainforest tree Symphonia globulifera

Cottet¹,

Genta‐Jouve²,

Fromentin³

et al. 2014

Phytochemistry

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Total Synthesis and Absolute Configuration Assignment of MRSA Active Garcinol and Isogarcinol

Socolsky

Plietker

2014

Chemistry A European J

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A short total synthesis of (±)-garcinol and (±)-isogarcinol, two endo-type B PPAPs with reported activity against methiciline resistant Staphylococcus aureus (MRSA), is presented. The separation of framework-constructing from framework-decorating steps and the application of two highly regio- and stereoselective Pd-catalysed allylations, that is, the Pd-catalysed decarboxylative Tsuji-Trost allylation and the diastereoselective Pd-catalysed allyl-allyl cross-coupling, are key elements that allowed the total synthesis to be accomplished within 13 steps starting from acetylacetone. After separation of the enantiomers the absolute configurations of the four natural products (i.e., (-)-garcinol, (+)-guttiferone E (i.e., ent-garcinol), (-)-isogarcinol, and (+)-isoxanthochymol (i.e., ent-isogarcinol)) were assigned based on ECD spectroscopy.

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Antiplasmodial benzophenone derivatives from the root barks of Symphonia globulifera (Clusiaceae)

Cited by 49 publications

References 24 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

Comparative LC–MS-based metabolite profiling of the ancient tropical rainforest tree Symphonia globulifera

Total Synthesis and Absolute Configuration Assignment of MRSA Active Garcinol and Isogarcinol

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