New Bioactive Coumarins from Kielmeyera albopunctata

Scio, Elita; Ribeiro, Antônia; Alves, Tânia Maria de Almeida; Romanha, Álvaro J.; Shin, Young Geun; Cordell, Geoffrey A.; Zani, Carlos L.

doi:10.1021/np020597r

Cited by 28 publications

(21 citation statements)

References 20 publications

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“…Trypanocidal activity of a coumarin from Kielmeyera albopunctata, a plant species from the Brazilian Cerrado, produced an 80% mortality rate of T. cruzi blood trypomastigotes at 125 μg/mL in a 24 hour period (Scio et al, 2003b). In the present study, coumarin 8 obtained from P. sabulosa showed in vitro activity against both cultured epimastigotes and blood trypomastigotes (IC 50 10.5 and 88.2 μg/mL, respectively).…”

Section: Resultssupporting

confidence: 52%

Trypanocidal activity of coumarins and styryl-2-pyrones from Polygala sabulosa A.W. Bennett (Polygalaceae)

Pizzolatti¹,

Mendes²,

Cunha³

et al. 2008

Rev. bras. farmacogn.

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Section: Resultssupporting

confidence: 52%

Trypanocidal activity of coumarins and styryl-2-pyrones from Polygala sabulosa A.W. Bennett (Polygalaceae)

Pizzolatti¹,

Mendes²,

Cunha³

et al. 2008

Rev. bras. farmacogn.

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“…brucei bloodstream trypomastigotes, with IC 50 values of 11 µM, while being non-toxic to KB cells (IC 50 values >170 µM) [42]. The coumarin 4-(1-methylpropyl)-5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)chromen-2-one (30) isolated from the stem bark of Kielmeyera albopunctata (Clusiaceae) was active in vitro against the trypomastigote form of T. cruzi in the infected murine blood assay, causing 80% inhibition at 125 µg/mL after 24 h contact at 4 ºC [60].…”

Section: Lignansmentioning

confidence: 99%

Natural Products from Plants as Drug Candidates and Lead Compounds Against Leishmaniasis and Trypanosomiasis

Salem

Werbovetz²

2006

CMC

133

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Millions of people in the developing world are affected by diseases caused by the kinetoplastid parasites: the leishmaniases, African trypanosomiasis, and Chagas disease. In many cases the drugs employed for treatment are toxic, marginally effective, given by injection, and/or compromised by the development of resistance. Since safe, effective, and affordable chemotherapeutic agents for leishmaniasis and trypanosomiasis are clearly needed, the identification of new antikinetoplastid drug candidates should be an urgent priority. Numerous plant-derived natural products from different structural classes have been investigated as antileishmanial and antitrypanosomal candidates, including various alkaloids, terpenoids, flavonoids, and quinonoids. This review outlines the antikinetoplastid activities of plant-derived natural products reported in the literature and also provides an overview of mechanistic studies that have been conducted with these compounds. Given the activities of these agents and their diverse range of effects on parasite biology, natural products are a potentially rich source of drug candidates and leads against leishmaniasis and trypanosomiasis.

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“…The coumarins mammea A/BA, A/BB, A/AA, A/BD and B/BA, isolated from C. brasiliense and Mamea americana , showed activity towards epimastigotes and trypomastigotes of T. cruzi for concentrations between 15 and 90 µg/mL [3]. Other coumarins isolated from the stem bark of Kielmeyera albopunctata showed in vitro activity against the trypomastigotes of T. cruzi , killing 80% of the parasites after 24 hours at 125 µg/mL [19].…”

Section: Introductionmentioning

confidence: 99%

Soulamarin Isolated from Calophyllum brasiliense (Clusiaceae) Induces Plasma Membrane Permeabilization of Trypanosoma cruzi and Mytochondrial Dysfunction

et al. 2013

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Chagas disease is caused by the parasitic protozoan Trypanosoma cruzi. It has high mortality as well as morbidity rates and usually affects the poorer sections of the population. The development of new, less harmful and more effective drugs is a promising research target, since current standard treatments are highly toxic and administered for long periods. Fractioning of methanol (MeOH) extract of the stem bark of Calophyllum brasiliense (Clusiaceae) resulted in the isolation of the coumarin soulamarin, which was characterized by one- and two-dimensional 1H- and 13C NMR spectroscopy as well as ESI mass spectrometry. All data obtained were consistent with a structure of 6-hydroxy-4-propyl-5-(3-hydroxy-2-methyl-1-oxobutyl)-6″,6″-dimethylpyrane-[2″,3″:8,7]-benzopyran-2-one for soulamarin. Colorimetric MTT assays showed that soulamarin induces trypanocidal effects, and is also active against trypomastigotes. Hemolytic activity tests showed that soulamarin is unable to induce any observable damage to erythrocytes (cmax. = 1,300 µM). The lethal action of soulamarin against T. cruzi was investigated by using amino(4-(6-(amino(iminio)methyl)-1H-indol-2-yl)phenyl)methaniminium chloride (SYTOX Green and 1H,5H,11H,15H-Xantheno[2,3,4-ij:5,6,7-i′j′]diquinolizin-18-ium, 9-[4-(chloromethyl)phenyl]-2,3,6,7,12,13,16,17-octahydro-chloride (MitoTracker Red) as fluorimetric probes. With the former, soulamarin showed dose-dependent permeability of the plasma membrane, relative to fully permeable Triton X-100-treated parasites. Spectrofluorimetric and fluorescence microscopy with the latter revealed that soulamarin also induced a strong depolarization (ca. 97%) of the mitochondrial membrane potential. These data demonstrate that the lethal action of soulamarin towards T. cruzi involves damages to the plasma membrane of the parasite and mitochondrial dysfunction without the additional generation of reactive oxygen species, which may have also contributed to the death of the parasites. Considering the unique mitochondrion of T. cruzi, secondary metabolites of plants affecting the bioenergetic system as soulamarin may contribute as scaffolds for the design of novel and selective drug candidates for neglected diseases, mainly Chagas disease.

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New Bioactive Coumarins from Kielmeyera albopunctata

Cited by 28 publications

References 20 publications

Trypanocidal activity of coumarins and styryl-2-pyrones from Polygala sabulosa A.W. Bennett (Polygalaceae)

Trypanocidal activity of coumarins and styryl-2-pyrones from Polygala sabulosa A.W. Bennett (Polygalaceae)

Natural Products from Plants as Drug Candidates and Lead Compounds Against Leishmaniasis and Trypanosomiasis

Soulamarin Isolated from Calophyllum brasiliense (Clusiaceae) Induces Plasma Membrane Permeabilization of Trypanosoma cruzi and Mytochondrial Dysfunction

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