Natural anthraquinones probed as Type I and Type II photosensitizers: singlet oxygen and superoxide anion production

Montoya, Susana C. Núñez; Comini, Laura R.; Sarmiento, Martín; Becerra, Cecilia; Albesa, Inés; Argüello, Gustavo A.; Cabrera, José Luis

doi:10.1016/j.jphotobiol.2004.09.009

Cited by 87 publications

(71 citation statements)

References 12 publications

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“…On the other hand, photosensitization caused by medicinal plants used in folk medicine, has been involved with a number of clinical skin syndromes, like dermatitis (Freitas et al, 2000;Montoya et al, 2005). The disturbances in the regulation of free radical and reactive oxygen species (ROS) processes in the organism is among the factors leading to several pathologies such as diabetes, Alzheimer, atherosclerosis, inflammatory disorders, myocardial infarction, cancer, and many others diseases (Amaral et al, 2009;Belinha et al, 2008;Parejo et al, 2003;Prior 2004).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of antimicrobial, antioxidant and phototoxic activities of extracts and isolated compounds from Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae

Souza¹,

Silva²,

Machado³

et al. 2010

Rev. bras. farmacogn.

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RESUMO: "Avalição da atividade antimicrobiana, antioxidante e fototóxica dos extratos e compostos isolados de Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae". Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae, é uma planta utilizada na medicina popular brasileira contra úlceras e lesões de pele. Internamente é usada contra inflamações, febre, doenças renais e aterosclerose. Essa planta foi estudada com o objetivo de identificar os compostos bioativos majoritários que possam justificar seu uso terapêutico contra lesões de pele e arteriosclerose. A atividade antioxidante do extrato bruto etanólico, partições e os compostos majoritários isolados das raízes de S. cayennesis foi avaliada através de testes in vivo e in vitro. In vitro a atividade antioxidante foi avaliada pelo teste fotocolorimétrico do radical 2,2-difenil-1-picrilidrazil (DPPH•). In vivo, Saccharomyces cerevisiae, um modelo de célula eucariótica, foi utilizado tanto para avaliar a fototoxicidade quanto a capacidade antioxidante contra as espécies reativas de oxigênio (EROS) menadiona e peróxido de hidrogênio. O extrato, partições e os dois compostos majoritários isolados, verbascosídeo e ácido betulínico foram capazes de aumentar a sobrevivência e diminuir a peroxidação lipídica de S. cerevisiae contra EROS. Verbascosídeo apresentou atividade antimicrobiana moderada contra Streptococcus pyogenes, S.epidermidis e Staphylococcus aureus. O extrato etanólico e as partições testadas não apresentaram fototoxicidade, indicando que S. cayennensis é uma planta segura para o tratamento de lesões de pele e como possível ingrediente em cosméticos.Unitermos: Stachytarpheta cayennensis, antioxidante, antimicrobial, fototoxicidade, arilpropanoide glicosilado, ácido betulínico.ABSTRACT: Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae, plant extract, is a Brazilian medicinal plant externally used in folk medicine for purulent ulcers, skin lesions and internally for inflammations, fever, renal disorders and atherosclerosis. S. cayennesis was studied to identify potential bioactive compounds that may justify their therapeutic use against skin lesions and atherosclerosis. The antioxidant, antimicrobial and phototoxicity capacities of the crude ethanolic extract, fractions and isolated compounds from roots of S. cayennesis were evaluated through in vivo and in vitro tests. Strains of Saccharomyces cerevisiae, an eukaryotic cell model, were used to assess both the phototoxicity and the capacity to protect against the lethal oxidative stress caused by menadione and hydrogen peroxide. The extract, fractions and the two major isolated compounds, verbascoside and betulinic acid, of S. cayennensis were able to increase the tolerance and decrease the lipid peroxidation of S. cerevisiae to reactive oxygen species (ROS). The antioxidant activity was also evaluated by scavenging of 2,2-diphenyl-1-picrylhydrazyl (DPPH•). Verbascoside exhibited a moderate antimicrobial activity against Streptococcus pyogenes, S.epidermidis and Staphylococcus aureus. Neither the ethanol...

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Section: Introductionmentioning

confidence: 99%

Evaluation of antimicrobial, antioxidant and phototoxic activities of extracts and isolated compounds from Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae

Souza¹,

Silva²,

Machado³

et al. 2010

Rev. bras. farmacogn.

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“…The chemical investigation of bioactive extracts revealed the predominance of 9,10-anthraquinone aglycones (AQs) (Figure 1) (Nuñez Montoya et al 2003, 2006Konigheim et al 2012) with demonstrated photosensitizing properties, which act by Type I (superoxide anion radical production, O 2 •À ) and/or Type II (singlet oxygen generation, 1 O 2 ) mechanisms (Nuñez Montoya et al 2005;Comini et al 2007). …”

Section: Introductionmentioning

confidence: 99%

Reduction ofCandida tropicalisbiofilm by photoactivation of aHeterophyllaea pustulataextract

Marioni

Arce

Cabrera

et al. 2016

Pharmaceutical Biology

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Context: Biofilm formation is an important problem, since this growth mode confers resistance to drugs usually used in therapeutics. Objective: In vitro antifungal activity of extracts obtained from Heterophyllaea pustulata Hook f. (Rubiaceae) were studied against Candida tropicalis biofilms, evaluating the effect of irradiation and the oxidative and nitrosative stresses as possible mechanisms of action. Materials and methods: Hexane, benzene, ethyl acetate and ethanol extracts were evaluated at three concentrations (0.2, 0.1 and 0.05 mg/mL) over mature biofilm, under darkness and irradiation. After 48 h of incubation, biofilm quantitation was performed by the O'Toole and Kolter method. Reactive oxygen species (ROS) was measured by nitro-blue tetrazolium (NBT) reaction and reactive nitrogen intermediates (RNI) by the Griess reagent. Superoxide dismutase activation (SOD, NBT assay) and total antioxidant system (FRAP test) were studied. Results: Only the benzene extract at 0.2 mg/mL reduced the biofilms formation. The slight decrease achieved in darkness (17.06 ± 2.80% reduction) was increased by light action (39.31 ± 3.50% reduction), clearly observing a photostimulation. This great reduction was confirmed by confocal microscopy. In darkness, biofilm reduction was mediated by an increase in RNI, whereas under irradiation, the ROS action was most important. Although no SOD activation was observed, a strong stimulation of the total antioxidant system was detected. HPLC analysis established a high content of several anthraquinones in this extract. Discussion and conclusion: Biofilm reduction by benzene extract was mainly mediated by oxidative stress triggered under light action, confirming a photodynamic sensitization, which could be attributed to its high content of photosensitizing anthraquinones. ARTICLE HISTORY

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“…They are also known as a family of photosensitizers, which photo-generate reactive oxygen species, such as 1 O 2 and O 2 - [5][6][7][8]. Thus, anthraquinones have been studied by using quantumchemical methods, mainly TD-DFT (Time-Dependant Density Functional Theory), in order to discuss their electronic spectra [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…2 10.0 ν C13C15 (13), ν C10C11 (13), ν O5C9 (9), ν C12C13 (6), ν C8C19 (6), 3 β 3/R6 (5) 76 1615.0 82.5 6.3 ρ N3H23 (19), ν C6C19 (8), ν C8C19 (7), ν C16C18 (7), ν C10C11 (7), ν C7C18 (7), ν C13C15 (7), 1 β 2/R6 (5) 77 1627.4 34.0 15.0 ν C14C15 (14), ν C11C12 (11), ν O5C9 (8), 3 β 2/R6 (7), ν C12C13 (7), ν C6C7 (5) 78 1631.2 279.7 4.8 ν C6C7 (16), ν C8C19 (6), 1 β 3/R6 (6), ν C14C15 (6), ν O4C17 (6) (8), ω N3H23 (6) 7 162.7 0.4 0.3 4 bfl RR (14), τ N3C18 (10), 2 bfl RR (10), 1 (13), 4 bfl RR (10) 11 221.4 5.2 0.4 τ S1C20 (21), δ 2/C20H31H32 (12), 2 bfl RR (8), β C18N3C2 (7), 4 bfl RR (7) (14), ν C11C17 (10), δ 2/C20H31H32 (7), ν C9C16 (6) 17 425.5 10.2 0.3 3 τ 3/R6 (40), ρ C9O5 (12), 4 bfl RR (10), 3 (15), ν S1C20 (8), ρ C18N3 (6) 27 652.2 1.9 0.9 ν S1C20 (58), 3 (8), ω C15H29 …”

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confidence: 99%

“…1.6 ρ C20H31H32 (25), β C20S1H33 (14), 1 β 3/R6 (8), 1 β trig/R6 (5) 35 785.9 5.5 0.3 3 τ 1/R6 (18), 2 τ 1/R6 (13), ω C7H25 (12), ω C9O5 (10), ω C19H30 (10), ω C17O4 (9), ω C6H24 (9) 36 796.0 0.1 0.7 1 β trig/R6 (13), ρ C20H31H32 (12), β C20S1H33 (12), 3 β 2/R6 (10), 1 β 3/R6 (9), 3 β trig/R6 (7) 37 808.4 0.5 0.1 ω C9O5 (25), ω C13H27 (13) (12), ν C8C19 (10), ν C11C17 (7), ρ C6H24 (6), ρ C14H28 (6) 58 1221.4 39.6 0.5 τ C20H31H32 (51), τ C2H22H21 (10) 59 1256. (7) 61 1293.8 528.9 10.6 (5) 62 1317.6 120.0 1.…”

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confidence: 99%

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Relationship between structure and entropy contributions in an anthraquinone mercapto derivative

2010

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The structural and thermodynamic properties of an anthraquinone derivative were studied by means of quantum-chemical calculations. As a result of the conformational analysis fourteen lowenergetic conformers were found by using ab initio and DFT methods. In order to discuss similarities and differences in entropy of the conformers, the rotational and vibrational contributions to entropy were correlated with changes in the conformer structure. The moment of inertia perpendicular to the molecular plane gives significant input to the ΔSrot, whereas the largest contributions to the ΔSvib have the vibrations associated with the τS1C20 coordinate.Response to Reviewers: Dear Prof. Andrzej Sokalski Editor in Chief of Journal of Molecular Modeling, I would like to thank the Referees for a careful reading of our manuscript and giving us the valuable comments that with no doubts will improve this paper (Mns.# JMMO1081). Please find below my answers to the Referees' suggestions and comments.Reviewer #1:Major Revisions 1. Some anthraquinones are proved to have anti-cancer and antifungal properties, as stated by the authors in the introduction. There, the anthraquinones are not in gas phase, but solved in the liquid phase or are interacting with the target in the liquid phase. In contrast, the calculations of the authors are performed in the gas phase. Thus, the authors should discuss, if their results have significance in drug research and for interaction between ligand and target. The molecular structure defined in the gas phase is a commonly accepted starting point in studies concerning biological activities of molecules. Indeed, we agree with the referee that the future research dealing strictly with biological activity of anthraquinones would require introduction of the solvent and simulation of a biological environment in computational models that is, by the way, a nontrivial problem. However, our studies on antraquinones brought us to finding of the entropic effect in the structures of the MEAA conformers and we decided to analyze this effect in detail. Therefore, our work, although mentioning biological functions of MEAA conformers, was in fact aimed to study the correlation of the rotational and vibrational contributions to entropy with changes in the conformer structure and to do this, the simplest possible model (the gas phase) occurred to us as the most preferable. In order to clarify our point of view we suggest adding two more sentences to Introduction (after : The highest emphasis was made on detailed analysis of the entropy effect in order to understand the relation between the structure and entropy contributions (translational, electronic, rotational and vibrational). The computations were done in the gas phase to simplify the computations. Nevertheless, it is hoped that this study can be a starting point in the future research concerning modeling of the biological activity of the MEAA in more complicated systems, mimicking the biological environment.2. How was the analysis of the potential energy p...

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Natural anthraquinones probed as Type I and Type II photosensitizers: singlet oxygen and superoxide anion production

Cited by 87 publications

References 12 publications

Evaluation of antimicrobial, antioxidant and phototoxic activities of extracts and isolated compounds from Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae

Evaluation of antimicrobial, antioxidant and phototoxic activities of extracts and isolated compounds from Stachytarpheta cayennensis (Rich.) Vahl, Verbenaceae

Reduction ofCandida tropicalisbiofilm by photoactivation of aHeterophyllaea pustulataextract

Relationship between structure and entropy contributions in an anthraquinone mercapto derivative

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