Structure–activity relationship of (−) mammea A/BB derivatives against Leishmania amazonensis

Brenzan, Mislaine Adriana; Nakamura, Celso Vataru; Filho, Benedito Prado Dias; Young, Maria Cláudia M.; Corrêa, Arlene G.; Júnior, Joel Alvim; Santos, Adriana O.; Cortez, Diógenes Aparı́cio Garcia

doi:10.1016/j.biopha.2008.08.024

Cited by 42 publications

(28 citation statements)

References 14 publications

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“…The aqueous extract was lyophilised (121.3 g). The dark-green residue from the extract, which had adhered to the glass bottles, was dissolved with dichloromethane and the solvent was completely evaporated at RT to yield a dichloromethane extract (25.0 g) (Brenzan et al 2007, 2008a, b). …”

Section: Methodsmentioning

confidence: 99%

“…Next, the hexane fraction (4.0 g) was further chromatographed on a vacuum silica-gel column and eluted with hexane, hexane/dichloromethane (98:2, 95:5, 90:10, 80:20 and 50:50), dichloromethane, dichloromethane/ethyl acetate (98:2, 95:5, 90:10, 80:20 and 50:50), ethyl acetate and methanol. The hexane fraction was evaporated to a residue, which was crystallised using dichloromethane (9:1), yielding compound (1) (52.0 mg), as described in previous studies (Gasparotto-Júnior et al 2005, Brenzan et al 2007, 2008a, b). Fractions 6-8 (667.0 mg), which were eluted in hexane, were chromatographed using thin layer chromatography and combined and then rechromatographed on a silica-gel column chromatograph (40 × 2.0 cm) eluted with hexane, hexane/dichloromethane (98:2-50:50), dichloromethane, dichloromethane/ ethyl acetate (95:5-50:50), ethyl acetate and finally methanol.…”

Section: Methodsmentioning

confidence: 99%

“…Fractions 6-8 (667.0 mg), which were eluted in hexane, were chromatographed using thin layer chromatography and combined and then rechromatographed on a silica-gel column chromatograph (40 × 2.0 cm) eluted with hexane, hexane/dichloromethane (98:2-50:50), dichloromethane, dichloromethane/ ethyl acetate (95:5-50:50), ethyl acetate and finally methanol. Next, fractions 1-12, which were eluted in hexane, were combined and evaporated to dryness, obtaining (2) (10.5 mg), as described in a previous study (Brenzan et al 2008b). The ethyl acetate fraction (1.83 g) of the dichloromethane extract was rechromatographed through a Sephadex LH-20 column and eluted with chloroform/methanol (1:1).…”

Section: Methodsmentioning

confidence: 99%

“…No activity was observed against Gram-negative bacteria (Enterobacter cloacae, Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa and Salmonella typhimurium) and yeasts (Candida albicans and Candida tropicalis) (Pretto et al 2004). Other studies have shown that the extracts, especially the coumarin (-) (1) isolated from C. brasiliense leaves, possess potent antileishmanial activity (Brenzan et al 2007, 2008a, b, 2012, Honda et al 2010, Tiuman et al 2012). …”

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confidence: 99%

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Anti-Mycobacterium tuberculosis activity and cytotoxicity of Calophyllum brasiliense Cambess (Clusiaceae)

Pires¹,

Brenzan²,

Scodro³

et al. 2014

Mem. Inst. Oswaldo Cruz

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We evaluated the in vitro anti-Mycobacterium tuberculosis activity and the cytotoxicity of dichloromethane extract and pure compounds from the leaves of Calophyllum brasiliense. Purification of the dichloromethane extract yielded the pure compounds (-) mammea A/BB (1), (-) mammea B/BB (2) and amentoflavone (3). The compound structures were elucidated on the basis of spectroscopic and spectrometric data. The contents of bioactive compounds in the extracts were quantified using high performance liquid chromatography coupled to an ultraviolet detector. The anti-M. tuberculosis activity of the extracts and the pure compounds was evaluated using a resazurin microtitre assay plate. The cytotoxicity assay was performed in J774G.8 macrophages using the 3-(4,5-dimethyl thiazol-2-yl)-2,5-diphenyl tetrazolium bromide colourimetric method. The quantification of the dichloromethane extract showed (1) and (2) at concentrations of 31.86 ± 2.6 and 8.24 ± 1.1 µg/mg of extract, respectively. The dichloromethane and aqueous extracts showed anti-M. tuberculosis H37Rv activity of 62.5 and 125 µg/mL, respectively. Coumarins (1) and (2) showed minimal inhibitory concentration ranges of 31.2 and 62.5 µg/mL against M. tuberculosis H37Rv and clinical isolates. Compound (3) showed no activity against M. tuberculosis H37Rv. The selectivity index ranged from 0.59-1.06. We report the activity of the extracts and coumarins from the leaves of C. brasiliense against M. tuberculosis.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Anti-Mycobacterium tuberculosis activity and cytotoxicity of Calophyllum brasiliense Cambess (Clusiaceae)

Pires¹,

Brenzan²,

Scodro³

et al. 2014

Mem. Inst. Oswaldo Cruz

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“…Compound 20 was found to be most effective in killing intracellular amastigote forms of Leishmania amazonensis. 38 Nishiyama et al showed that 6,7-dihydroxy-4,4-dimethyldihydrocoumarin 21 can serve as an effective antioxidant for preventing the oxidation of oils and fats. Also, substituted dihydrocoumarins having the basic structural motif of 21, behave as better chain-breaking antioxidants for the autooxidation of tetralin and linoleic acid than structurally comparable α-tocopherol.…”

Section: Biological Activitymentioning

confidence: 99%

Syntheses and Biological Activities of Chroman-2-ones. A Review

Kamat

Tilve

Kamat

et al. 2015

Organic Preparations and Procedures International

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Synthesis, In Silico Studies, Antiprotozoal and Cytotoxic Activities of Quinoline‐Biphenyl Hybrids

et al. 2020

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The synthesis, in silico studies, antiprotozoal and cytotoxic activities of eleven quinoline‐biphenyl hybrids are described herein. The structure of the synthesized products was elucidated by a combination of spectrometric analyses. The synthesized compounds were evaluated against Plasmodium falciparum, and amastigotes forms both Leishmania (V) panamensis and Trypanosoma cruzi. Cytotoxicity was evaluated against human U‐937 macrophages. 8‐phenylquinoline (4 a) showed similar activity than meglumine antimoniate and 4‐(quinolin‐8‐yl)phenol (4 b) exhibited an activity similar to that of benznidazole. 8‐(3,4‐dimethoxyphenyl) quinoline (4 k) showed the best activity against P. falciparum. Although these compounds were toxic for mammalian U‐937 cells, however they may still have potential to be considered as candidates for drug development because of their antiparasite activity. Molecular docking was used to determine the in silico inhibition of some of the designed compounds against PfLDH and cruzipain, two important pharmacological targets involved in antiparasitic diseases. All hybrids were docked to the three‐dimensional structures of PfLDH and T. cruzi cruzipain as enzymes using AutoDock Vina. Notably, the docking results showed that the most active compounds 4‐(quinolin‐8‐yl)phenol (4 b, CE50: 11.33 μg/mL for T. cruzi) and 8‐(3,4‐dimethoxyphenyl) quinoline (4 k, CE50: 8.84 μg/mL for P. falciparum) exhibited the highest scoring pose (−7.5 and −7.7 kcal/mol, respectively). This result shows a good correlation between the predicted scores with the experimental data profile, suggesting that these ligands could act as competitive inhibitors of PfLDH or T. cruzi cruzipain enzymes, respectively. Finally, in silico ADME studies of the quinoline hybrids showed that these novel compounds have suitable drug‐like properties, making them potentially promising agents for antiprotozoal therapy.

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Structure–activity relationship of (−) mammea A/BB derivatives against Leishmania amazonensis

Cited by 42 publications

References 14 publications

Anti-Mycobacterium tuberculosis activity and cytotoxicity of Calophyllum brasiliense Cambess (Clusiaceae)

Anti-Mycobacterium tuberculosis activity and cytotoxicity of Calophyllum brasiliense Cambess (Clusiaceae)

Syntheses and Biological Activities of Chroman-2-ones. A Review

Synthesis, In Silico Studies, Antiprotozoal and Cytotoxic Activities of Quinoline‐Biphenyl Hybrids

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