7-Epiclusianone, a Benzophenone Extracted from  Garcinia brasiliensis (Clusiaceae), Induces Cell Cycle Arrest in G1/S Transition in A549 Cells

Ionta, Marisa; Ferreira-Silva, Guilherme Álvaro; Niero, Evandro Luís de Oliveira; Costa, Éderson D'Martin; Martens, Adam Arai; Rosa, Welton; Soares, Marisi G.; Machado-Santelli, Gláucia Maria; Lago, João Henrique G.; Santos, Marcelo Henrique dos

doi:10.3390/molecules200712804

Cited by 27 publications

(21 citation statements)

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“…So far, few articles suggested a potential antiproliferative effect of G. brasiliensis after 7- epiclusianone treatment of human cancer cell lines, including melanoma, kidney, ovarian, prostate and lung [ 23 , 24 ].…”

Section: Resultsmentioning

confidence: 99%

“…In A549 lung cells, 7- epiclusianone treatment also induced apoptosis and cell cycle arrest in G1/S transition. Additionally, the cytotoxic activity of 7- epiclusianone in normal fibroblasts (CCD-1059Sk) was also evaluated and IC 50 value was approximately 58 μM, 2.5 and 3.2 times higher than for the cancer cell lines tested herein, U251MG and U138MG [ 24 ].…”

Section: Resultsmentioning

confidence: 99%

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Anticancer activity of 7-epiclusianone, a benzophenone from Garcinia brasiliensis, in glioblastoma

Sales

Pezuk

Borges

et al. 2015

BMC Complement Altern Med

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BackgroundGlioblastoma is the most common tumor of the central nervous system and one of the hardest tumors to treat. Consequently, the search for novel therapeutic options is imperative. 7-epiclusianone, a tetraprenylated benzophenone isolated from the epicarp of the native plant Garcinia brasiliensis, exhibits a range of biological activities but its prospect anticancer activity is underexplored. Thus, the aim of the present study was to evaluate the influence of 7-epiclusianone on proliferation, clonogenic capacity, cell cycle progression and induction of apoptosis in two glioblastoma cell lines (U251MG and U138MG).MethodsCell viability was measured by the MTS assay; for the clonogenic assay, colonies were stained with Giemsa and counted by direct visual inspection; For cell cycle analysis, cells were stained with propidium iodide and analyzed by cytometry; Cyclin A expression was determined by immunoblotting; Apoptotic cell death was determined by annexin V fluorescein isothiocyanate labeling and Caspase-3 activity in living cells.ResultsViability of both cell lines was drastically inhibited; moreover, the colony formation capacity was significantly reduced, demonstrating long-term effects even after removal of the drug. 7-epiclusianone treatment at low concentrations also altered cell cycle progression, decreased the S and G2/M populations and at higher concentrations increased the number of cells at sub-G1, in concordance with the increase of apoptotic cells.ConclusionThe present study demonstrates for the first time the anticancer potential of 7-epiclusianone against glioblastoma cells, thus meriting its further investigation as a potential therapeutic agent.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Anticancer activity of 7-epiclusianone, a benzophenone from Garcinia brasiliensis, in glioblastoma

Sales

Pezuk

Borges

et al. 2015

BMC Complement Altern Med

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“…In this context, natural products have become an important source for the discovery of new therapeutic agents. Plants are especially rich in these types of compounds due to their wide chemical diversity [ 4 ] and represent an important source for new varieties of molecules [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of 7-Epiclusianone and Its Novel Copper Metal Complex on Streptococcus spp. Isolated from Bovine Mastitis and Their Cytotoxicity in MAC-T Cells

Barros

Perciano²,

Santos

et al. 2017

Molecules

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Mastitis is an inflammation of mammary gland parenchyma that adversely affects bovine health and dairy production worldwide despite significant efforts to eradicate it. The aim of this work was to characterize the antimicrobial activity of 7-epiclusianone (7-epi), a compound extracted from the Rheedia brasiliensis fruit, its complex with copper against Streptococcus spp. isolated from bovine mastitis, and to assess their cytotoxicity to bovine mammary alveolar cells (MAC-T). The complex 7-epiclusianone-Cu (7-epi-Cu) was an amorphous green solid with optical activity. Its vibrational spectrum in the infrared region showed absorption bands in the high-frequency region, as well as bands that can be attributed to the unconjugated and conjugated stretching of the free ligand. The complex was anhydrous. One of the tested bacterial strains was not sensitive to the compounds, while the other three had MIC values of 7.8 µg mL−1 and minimum bactericidal concentration (MBC) values between 15.6 and 31.3 µg mL−1. These two compounds are bacteriostatic, did not cause damage to the cell wall and, at sub-inhibitory concentrations, did not induce bacterial adhesion. The compounds were not cytotoxic. Based on these results, 7-epi and 7-epi-Cu exhibited desirable antimicrobial properties and could potentially be used in bovine mastitis treatment.

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“…Isogarcinol (2), a natural compound is a new immunosuppressant and has anti-inflammatory effects [22]. 7-epi-clusianone (3) shows antiproliferative activity against cancer cell lines [23] and has influence on proliferation, clonogenic activity cell cycle progression and induction of apoptosis in two glioblastoma cell lines [24]. Clearly, these compounds have considerable clinical potential but they suffer from a lack of sensitive and reliable way to quantify these molecules in the extracts of the Garcinia species.…”

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A Rapid Determination and Quantification of Three Biologically Active Polyisoprenylated Benzophenones using Liquid Chromatography-Tandem Mass Spectrometry (MRM) Method in Five Garcinia species from Cameroon

Biloa

Marti

et al. 2017

Natural Product Communications

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Following investigation of Garcinia genus, a sensitive, rapid and simple reversed-phase high performance liquid chromatography-electrospray ionization mass spectrometry method has been developed for the identification and quantification of three polyisoprenylated benzophenones, garcinol (1), isogarcinol (2) and 7-epi-clusianone (3), in the extracts of five Garcinia species from Cameroon. The separation of those compounds was achieved on a RP-18 column using a solvent system consisting of a mixture of acetonitrile-water-formic acid as a mobile phase in a gradient elution mode. The identification of the three compounds was determined on a triple quadripole mass spectrometer with ESI interface operating in the negative mode. A multiple reaction monitoring (MRM) method was developed for the quantification of these polyisoprenylated benzophenones in the extracts of the Garcinia species. The method was validated through intra-and inter-day precision, with the relative standard deviation (RSD) less than 6%, limits of detection (LOD) and limits of quantification (LOQ) <1 ng. Overall recoveries ranged from 94% to 104%, with RSDs ranging from 0.8% to 4.5%. The results indicated that the fruits of G. preussii and the roots of G. brevipedicellata are good source of garcinol (1) and isogarcinol (2) respectively.

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7-Epiclusianone, a Benzophenone Extracted from Garcinia brasiliensis (Clusiaceae), Induces Cell Cycle Arrest in G1/S Transition in A549 Cells

Cited by 27 publications

References 27 publications

Anticancer activity of 7-epiclusianone, a benzophenone from Garcinia brasiliensis, in glioblastoma

Anticancer activity of 7-epiclusianone, a benzophenone from Garcinia brasiliensis, in glioblastoma

Antibacterial Activity of 7-Epiclusianone and Its Novel Copper Metal Complex on Streptococcus spp. Isolated from Bovine Mastitis and Their Cytotoxicity in MAC-T Cells

A Rapid Determination and Quantification of Three Biologically Active Polyisoprenylated Benzophenones using Liquid Chromatography-Tandem Mass Spectrometry (MRM) Method in Five Garcinia species from Cameroon

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