Effects of (−) mammea A/BB isolated from Calophyllum brasiliense leaves and derivatives on mitochondrial membrane of Leishmania amazonensis

Brenzan, Mislaine Adriana; Santos, Adriana O.; Nakamura, Celso Vataru; Filho, Benedito Prado Dias; Ueda-Nakamura, Tânia; Young, Maria Cláudia Marx; Corrêa, Arlene G.; Júnior, Joel Alvim; Morgado‐Díaz, José Andrés; Cortez, Diógenes Aparı́cio Garcia

doi:10.1016/j.phymed.2011.10.008

Cited by 41 publications

(34 citation statements)

References 40 publications

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“…In addition, an intense exocytic process of cytoplasmic content into the flagellar pocket was noted. Mitochondrion seems to be a common target for several natural products, crude extracts, or isolated compounds, as has been reported by several researchers [10, 22–24]. The mode of action of most natural products that cause mitochondrial damage and parasite death has been attributed mainly to sterol biosynthesis inhibition and mitochondrial membrane potential dysfunction [25–27].…”

Section: Resultsmentioning

confidence: 97%

Arrabidaea chicaHexanic Extract Induces Mitochondrion Damage and Peptidase Inhibition onLeishmaniaspp.

Rodrigues

Azevedo

Chaves

et al. 2014

BioMed Research International

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Currently available leishmaniasis treatments are limited due to severe side effects. Arrabidaea chica is a medicinal plant used in Brazil against several diseases. In this study, we investigated the effects of 5 fractions obtained from the crude hexanic extract of A. chica against Leishmania amazonensis and L. infantum, as well as on the interaction of these parasites with host cells. Promastigotes were treated with several concentrations of the fractions obtained from A. chica for determination of their minimum inhibitory concentration (MIC). In addition, the effect of the most active fraction (B2) on parasite's ultrastructure was analyzed by transmission electron microscopy. To evaluate the inhibitory activity of B2 fraction on Leishmania peptidases, parasites lysates were treated with the inhibitory and subinhibitory concentrations of the B2 fraction. The minimum inhibitory concentration of B2 fraction was 37.2 and 18.6 μg/mL for L. amazonensis and L. infantum, respectively. Important ultrastructural alterations as mitochondrial swelling with loss of matrix content and the presence of vesicles inside this organelle were observed in treated parasites. Moreover, B2 fraction was able to completely inhibit the peptidase activity of promastigotes at pH 5.5. The results presented here further support the use of A. chica as an interesting source of antileishmanial agents.

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Section: Resultsmentioning

confidence: 97%

Arrabidaea chicaHexanic Extract Induces Mitochondrion Damage and Peptidase Inhibition onLeishmaniaspp.

Rodrigues

Azevedo

Chaves

et al. 2014

BioMed Research International

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“…The presence of a dihydrocoumarin segment was based on the multiplets at δ 2.4–2.5 (2H) and δ 3.48 (1H), which were assigned to H-3a/H-3b and H-4, respectively. The multiplets at δ 1.30 (H-14), 1.32 (H-15) and the triplet at δ0.64 ( J = 7.5 Hz, H-16) were assigned to an n -propyl chain linked to C-4 [30]. The doublets at δ 0.97 and 1.28 ( J = 6.4 Hz) were attributed to the methyl groups H-5′ and H-4′, while the multiplets at δ 2.30 and 3.93 were assigned to H-2′ and H-3′ of the isoprene moiety at C-5.…”

Section: Resultsmentioning

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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“…The species occurs in flooded forests and is well adapted to hypoxic conditions (Marques and Joly, 2000) and it is therefore indicated for restoration programs (Nery et al, 2007). The plant has potential for use in the timber industry due to the good quality of its wood (Flores, 2002;Cole et al, 2011) and also presents medicinal properties (Noldin et al, 2006;Souza et al, 2009;Brenzan et al, 2012), including cancer chemopreventive activity (Ito et al, 2002). Moreover, due to wood exploitation and environmental pressure, natural populations of C. brasiliense have been reduced in the recent years (Marques and Joly, 2000) and this species is listed as endangered in some Brazilian states such as São Paulo (São Paulo, 2008).…”

Section: Introductionmentioning

confidence: 99%

Micropropagation of Calophyllum brasiliense (Cambess.) from nodal segments

et al. 2016

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Micropropagation of Calophyllum brasiliense Cambess. (Clusiaceae) is a way to overcome difficulties in achieving large-scale plant production, given the recalcitrant nature of the seeds, irregular fructification and absence of natural vegetative propagation of the species. Cultures were established using nodal segments 2 cm in length, obtained from 1-2 year old seedlings, maintained in a greenhouse. Mercury chloride and Plant Preservative Mixture™ were used in the surface sterilizing stage, better results being achieved with Plant Preservative Mixture™ incorporation in culture medium, at any concentration. Polyvinylpyrrolidone, activated charcoal, cysteine, ascorbic acid or citric acid were added to the culture medium to avoid oxidation. After 30 days of culture, polyvinylpirrolidone and ascorbic acid gave better results, eliminating oxidation in most explants. For shoot multiplication, benzylaminopurine was used in concentrations of 4.4 and 8.8 µM in Woody Plant Medium, resulting in an average of 4.43 and 4.68 shoots per explant, respectively, after 90 days. Indole-3-butyric acid and α-naphthalene acetic acid were used to induce root formation, reaching a maximum rooting rate of 24% with 20µM α-naphthalene acetic acid. For acclimatization. the rooted plants were transferred to Plantmax  substrate and cultured in a greenhouse, reaching 79% of survival after 30 days and 60% after one year.

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Effects of (−) mammea A/BB isolated from Calophyllum brasiliense leaves and derivatives on mitochondrial membrane of Leishmania amazonensis

Cited by 41 publications

References 40 publications

Arrabidaea chicaHexanic Extract Induces Mitochondrion Damage and Peptidase Inhibition onLeishmaniaspp.

Arrabidaea chicaHexanic Extract Induces Mitochondrion Damage and Peptidase Inhibition onLeishmaniaspp.

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

Micropropagation of Calophyllum brasiliense (Cambess.) from nodal segments

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