Analgesic and anti-inflammatory activities of a fraction rich in oncocalyxone A isolated from Auxemma oncocalyx

Ferreira, Mariana; Nunes, Osmar D.R.H.; Fontenele, Juvenia Bezerra; Pessoa, Otília Deusdênia Loiola; Lemos, Telma L. G.; Viana, G. S. B.

doi:10.1078/0944711041495227

Cited by 43 publications

(32 citation statements)

References 43 publications

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“…Moreover, only DXR and A. oncocalyx exhibited an increase in oocytes with abnormal chromatin configuration, showing less harmful effect of onco A. This result may be due to the impurity of the fraction of A. oncocalyx that contains 80% of onco A (FERREIRA et al, 2004), and 20% of other substances that may be more toxic than onco A alone. In addition, Pessoa et al (PESSOA et al, 2003)increasing the risk for the development of a second cancer, particularly acute leukemia.…”

Section: Resultsmentioning

confidence: 76%

“…Notably, the fraction of A. oncocalyx contained 80% of onco A (FERREIRA et al, 2004), therefore the concentration of A. oncocalyx was in equal proportion of onco A. A. oncocalyx and onco A were diluted with dimethyl sulfoxide (DMSO) as a vehicle.…”

Section: Source Of Ovariesmentioning

confidence: 99%

“…It has been widely used in folk medicine as an adjunctive treatment for injuries (BRAGA, 1976;FERREIRA et al, 2003). Some studies have attributed biological activities such as analgesic, anti-oxidant, anti-tumor, and antiinflammatory effects to this plant (PESSOA et al, 1992;LINO et al, 1996;FERREIRA et al, 2003FERREIRA et al, , 2004. Oncocalyxone A (onco A) isolated from the stem heartwood of the plant has demonstrated high antioxidant activity (FERREIRA et al, 2003) and an antiproliferative effects on tumor cell cultures (COSTA-LOTUFO et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

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Toxicity effect of Auxemma oncocalyx fraction and its active principle oncocalyxone A on in vitro culture of caprine secondary follicles and in vitro oocyte maturation

Leiva-Revilla

Vieira

Campello

et al. 2017

SCA

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The extract of Auxemma oncocalyx (A. oncocalyx) and its main component, oncocalyxone A (onco A), possess anti-tumoral activity that may affect fertility. There is limited literature on the action of these substances regarding caprine folliculogenesis. In this study, we evaluated the effect of A. oncocaly and onco A on the in vitro culture of isolated secondary follicles (Experiment 1) and on the in vitro maturation (IVM) of oocytes from caprine antral follicles grown in vivo (Experiment 2). Isolated secondary follicles were distributed in six groups: the non-cultured control was immediately fixed in 4% paraformaldehyde. The remaining follicles were cultured for 7 days in α-minimal essential medium (α-MEM + ) alone (control) or with dimethyl sulfoxide (DMSO), doxorubicin (DXR), A. oncocalyx, or onco A. After culture, the follicles were evaluated for antrum formation, growth rate, apoptosis (TUNEL), cellular proliferation (PCNA), as well as the expression of BCL2 and BAX. In addition, cumulus oocyte complexes (COCs) were aspirated and allocated into five treatments for IVM: control, cultured only in maturation base medium (TCM 199 + ); or supplemented with DMSO; DXR; A. oncocalyx or onco A. After IVM, oocyte chromatin configuration and viability were assessed. After 7 days of culture, a reduction was noted in the percent of morphologically intact follicles, antrum formation, growth rate, and numbers of PCNApositive granulosa cells (P < 0.05). After culture, the DXR treatment showed a higher percent of TUNELpositive follicles and relative BAX:BCL2 mRNA ratio's (P < 0.05). After IVM of the COCs, DXR, A. oncocalyx, and onco A treatments showed a greater percent (P < 0.05) of abnormal oocytes and a lower percent of viable oocytes as compared with the control group (P < 0.05). However, only DXR and onco A treatments increased the percent of alive oocytes with abnormal chromatin configuration (P < 0.05). There were no differences in the maturation rates among the control group and DXR, A. oncocalyx, and onco A treatments. In conclusion, under our culture conditions, A. oncocalyx and onco A did not exhibit toxic effect on isolated secondary follicles and on maturation rates of COCs recovered from antral follicles. However, these substances negatively affected the oocyte viability. Thus, culture methods including in vitro secondary follicle culture and in vitro oocyte maturation toxicity test are appropriate methods to evaluate the possible effects of drugs on folliculogenesis. ResumoO extrato da Auxemma oncocalyx (A. oncocalyx) e seu componente, Oncocalyxona A (onco A), possui atividade antitumoral, podendo afetar a fertilidade. Entretanto, estudos sobre a ação dessas substâncias em relação à foliculogênese caprina são desconhecidos. O objetivo desse estudo foi avaliar o efeito da A. oncocalyx e onco A no cultivo in vitro de folículos secundários isolados (Experimento 1) e na maturação in vitro (MIV) de oócitos de folículos antrais caprinos crescidos in vivo (Experimento 2). Folículos secundários isolados foram ...

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Section: Resultsmentioning

confidence: 76%

Section: Source Of Ovariesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Toxicity effect of Auxemma oncocalyx fraction and its active principle oncocalyxone A on in vitro culture of caprine secondary follicles and in vitro oocyte maturation

Leiva-Revilla

Vieira

Campello

et al. 2017

SCA

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“…7,[10][11][12] Oncocalyxone A (1) also showed differential antitumor activity against the murine tumors Ehrlich carcinoma, sarcoma 180 and L1210 leukemia. Other pharmacological activities were also ascribed to the quinone fraction obtained from A. oncocalyx extract.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical determination of oncocalyxone A using an iron-phthalocyanine/iron-porphyrin modified glassy carbon electrode

Costa¹,

Souza²,

Luz³

et al. 2008

J. Braz. Chem. Soc.

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Descreve-se, no presente trabalho, o desenvolvimento de um sensor voltamétrico altamente sensível para a oncocalixona A, utilizando-se eletrodo de carbono vítreo modificado com uma bicamada de ftalocianina tetrassulfonada de ferro(II) (FeTSPc) e tetra-(N-metil-4-piridil)-porfirina de ferro(III) (FeT 4 MPyP). O eletrodo modificado apresentou alta atividade catalítica e estabilidade em relação à redução da oncocalixona, proporcionando deslocamento anódico de ca. de 30 mV e amplificação da corrente de pico, em relação a iguais parâmetros obtidos em eletrodo de carbono vítreo não modificado. Um ampla faixa linear de resposta entre 0.005-1.2 µmol L -1 , com sensibilidade de 8.11 µA L µmol -1 e limites de detecção (LOD) e quantificação (LOQ) de 1.5 e 5 nmol L -1 foram obtidos, com o uso desse sensor.The development of a highly sensitive voltammetric sensor for oncocalyxone A using a glassy carbon electrode modified with a bilayer iron(II) tetrasulfonated phthalocyanine (FeTSPc) and iron(III) tetra-(N-methyl-4-pyridyl)-porphyrin (FeT 4 MPyP) is described. The modified electrode showed high catalytic activity and stability for the oncocalyxone A reduction, provoking the anodic shift of the reduction peak potentials of ca. 30 mV and presenting much higher peak currents than those obtained on the bare GC electrode. A wide linear response range between 0.005-1.2 µmol L -1 , with a sensitivity of 8.11 µA L µmol -1 and limits of detection (LOD) and quantification (LOQ) of 1.5 and 5 nmol L -1 were obtained with this sensor.Keywords: voltammetric sensor, oncocalyxone, quinone, chemically modified electrodes, catalysis IntroductionPlants are repositories for bioactive organic molecules. Several classes of natural compounds are pharmacologically active ingredients and serve as drugs and/or leads for drug developments. Among them, quinones, ubiquitous secondary metabolites, play essential roles, mainly in the biochemistry of energy production, serving as vital links in the electron transport. 1 They form an important class of toxic metabolites and paradoxically, can be either, potentially carcinogenic or effective anticancer agents. The cytotoxic activity of quinones can often be correlated to their chemical behavior. The striking feature of quinone chemistry is the ease reduction and therefore their ability to act as oxidizing or dehydrogenating agents, the driving force being the formation of a fully aromatic system. [2][3][4][5] Auxemma oncocalyx Taub. is a native Brazilian tree, characteristic of the xerophytic vegetation present in the northeastern region. It is commonly called "pau branco." The chemical investigation of A. oncocalyx heartwood extracts resulted in the isolation and characterization of several unusual terpenoid quinones and hydroquinones of C 16 framework. 6-9 These secondary metabolites seem to be typical of the genus and, interestingly, were isolated in a homolog series differing in their degree of oxidation, oxygenation (ether or alcohol), rearrangement and intramolecular cyclization of the terpenoid side ...

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“…6, 2012 of platelet activation. 3,4,[5][6][7][8] Oncocalyxone A also shows differential antitumor activity against the murine tumors Ehrlich carcinoma, sarcoma 180 and L1210 leukemia. 8 In general, two major mechanisms of quinone cytotoxicity have been proposed: stimulation of oxidative stress and alkylation of cellular nucleophiles, which encompass large range of biomolecules, 9 such as DNA and some enzymes, e.g., topoisomerase and protein tyrosine phosphatases, mainly those with thiol groups.…”

Section: Introductionmentioning

confidence: 99%

Oncocalyxone A: electrochemical, spectroscopic investigation and studies of its interaction with DNA, nucleobases and N-acetylcysteine

Costa¹,

Costa²,

Ferreira³

et al. 2012

J. Braz. Chem. Soc.

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A formação de espécies paramagnéticas a partir da oncocalixona A em meio aprótico foi confirmada pela realização de experimentos eletroquímicos in situ em conjunto com ressonância de spin eletrônico (E-ESR). A alta deslocalização do radical gerado no primeiro potencial de redução está claramente evidenciada pelo acoplamento hiperfino do H-9 com a maior constante de acoplamento, além dos acoplamentos nas posições H-3 (próximo à quinona) e H-7 (distante do núcleo quinônico). Em meio prótico, além dos experimentos de dependência com o pH, oncocalixona A mostrou-se DNA-reativa por meio de experimentos eletroquímicos com sensores de DNA. Sua reação com N-acetilcisteína, com caracterização estrutural dos produtos de adição, evidencia sua habilidade como aceptor de Michael. Ambos os aspectos são importantes em termos de atividades biológicas/farmacológicas e indicam os presentes modelos como ferramentas importantes na avaliação de compostos biologicamente ativos.The formation of paramagnetic species from oncocalyxone A in aprotic medium was confirmed by performing in situ electrochemical-electron spin resonance (E-ESR) experiments. The high delocalization of the radical generated at the first reduction potential is clearly evidenced by the hyperfine coupling of H-9 with the larger coupling constant, besides the couplings at the H-3 (close to quinone) and H-7 (far from the quinone nucleus) positions. In protic medium, together with pH dependence experiments, oncocalyxone A showed to be DNA-reactive through experiments with DNA sensors. Its reaction with N-acetylcysteine, with structural characterization of the addition products, proved its ability as Michael acceptor. Both aspects are important in terms of biological/ pharmacological activities and indicate the present models as important tools in the screening of biologically active compounds.Keywords: oncocalyxone A, spectroelectrochemical-electron spin resonance, DNA interaction, N-acetylcysteine, Michael acceptor IntroductionOncocalyxone A (rel-8α-hydroxy-5-hydroxymethyl-2 -m e t h o x y -8 a , β -m e t h y l -7 , 8 , 8 a , 9 -t e t r a h y d r o -1,4-anthracenedione) ( Figure 1a) is a natural parabenzoquinone isolated from Auxemma oncocalyx TAUB, popularly known as "pau branco", that belongs to the Boraginaceae family. 1,2 Oncocalyxone A exhibits a series of biological properties, 2 such as cytotoxic, analgesic and anti-inflammatory, it causes DNA damage and inhibition Costa et al. 1175 Vol. 23, No. 6, 2012 of platelet activation. 3,4,[5][6][7][8] Oncocalyxone A also shows differential antitumor activity against the murine tumors Ehrlich carcinoma, sarcoma 180 and L1210 leukemia. 8 In general, two major mechanisms of quinone cytotoxicity have been proposed: stimulation of oxidative stress and alkylation of cellular nucleophiles, which encompass large range of biomolecules, 9 such as DNA and some enzymes, e.g., topoisomerase and protein tyrosine phosphatases, mainly those with thiol groups. 10 Oncocalyxone A, a para-benzoquinone with an extended conjugated dienon...

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Analgesic and anti-inflammatory activities of a fraction rich in oncocalyxone A isolated from Auxemma oncocalyx

Cited by 43 publications

References 43 publications

Toxicity effect of Auxemma oncocalyx fraction and its active principle oncocalyxone A on in vitro culture of caprine secondary follicles and in vitro oocyte maturation

Toxicity effect of Auxemma oncocalyx fraction and its active principle oncocalyxone A on in vitro culture of caprine secondary follicles and in vitro oocyte maturation

Electrochemical determination of oncocalyxone A using an iron-phthalocyanine/iron-porphyrin modified glassy carbon electrode

Oncocalyxone A: electrochemical, spectroscopic investigation and studies of its interaction with DNA, nucleobases and N-acetylcysteine

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