It was synthesized nine polyoxygenated chalcones with a potential and safe use as antioxidant, antimicrobial and anti-inflammatory therapies. Chalcones obtained by Claisen-Schmidt condensation were studied as antioxidant, inhibitors of human 5-lipoxygenase, antifungal, antibacterial and antibiotic resistance modifiers. Two chalcones with catecholic moieties were able to strongly decrease the minimum inhibitory concentration (MIC) of methicillin against methicillin-resistant Staphylococcus aureus, increase the antiradical activity and significantly inhibit the human 5-lipoxygenase. Only one of these chalcones was active synergistically with methicillin. Chalcones with methoxyl substituents at different positions displayed the best activities against Cryptococcus neoformans. Only one chalcone showed good activity against the plant pathogenic bacteria Pseudomonas syringae whose half maximal inhibitory concentration (IC50) value (2.5 µg mL-1) was similar to that observed with the antibiotic streptomycin (2.9 µg mL-1). These simple chalcones have safe potential uses in antioxidant, antimicrobial and anti-inflammatory therapies.

Dos series de 4-aril-3-metil-1,2,3,4-tetrahidroquinolinas fueron sintetizadas de acuerdo con una metodología sintética de dos pasos y evaluadas como potenciales agentes antifúngicos. El paso clave involucró la formación de las correspondientes N-bencil tetrahidroquinolinas 5 vía una cicloadición imino Diels-Alder catiónica. El segundo paso consistió en obtener las tetrahidroquinolinas N-desprotegidas 6 vía una desbencilación catalítica. Los productos fueron aislados y purificados usando cromatografía en columna (CC). Las sustancias fueron identificadas usando resonancia magnética nuclear (RMN), espectrometría de masas (EM) y espectroscopia infrarroja (IR). Los compuestos fueron evaluados in vitro frente a cepas estandarizadas de hongos clínicamente relevantes, incluyendo levaduras, hialohifomicetes y dermatofitos. Estos estudios mostraron que, de las tetrahidroquinolinas ensayadas, los compuestos 6f y 6g mostraron actividad antifúngica, específicamente frente a dermatofitos. El compuesto 6-metoxi-4-(4-hidroxi-3-metoxifenil)-3-metil-1,2,3,4-tetrahidroquinolina 6g exhibió la mejor actividad (MIC 32-65 μg/mL). Los resultados indican que remover el grupo bencilo e introducir un grupo hidroxilo en el sustituyente arilo de las N-bencil tetrahidroquinolinas produce un mejoramiento de la actividad antifúngica. Predicciones in silico complementaron los resultados: la mayoría de las tetrahidroquinolinas ensayadas mostraron alta biodisponibilidad, altos "drug scores" y bajo riesgo potencial.

Two series of 4-aryl-3-methyl-1,2,3,4-tetrahydroquinoline derivatives were efficiently synthesized according to a two-step synthesis and evaluated as potential antifungal agents. The key step was the formation of the corresponding N-benzyltetrahydroquinolines 5 via a three-component cationic imino Diels-Alder cycloaddition. The second step was a catalytic debenzylation to obtain the N-unprotected tetrahydroquinolines 6. The products were isolated and purified by column chromatography. Substances were characterized using nuclear magnetic resonance (NMR) mass spectrometry (MS) and infrared spectroscopy (IR). All compounds were tested in vitro against standardized, clinically important fungi, including yeasts, hialohyphomycetes, and dermatophytes. These studies showed that between the tetrahydroquinoline series tested, compounds 6f and 6g showed antifungal activity, specifically against dermatophytes. The compound 6-methoxy-4-(4-hydroxi-3-methoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline 6g exhibited the best in vitro activity (MIC 32-65 μg/mL). The results indicated that the elimination of benzyl group from the N-benzyltetrahydroquinolines derivatives, as well as the introduction of a hydroxyl group in the 4-aryl substituent caused a significant improvement in the antifungal activity. These results were supplemented by the in silico prediction; most of the tetrahydroquinolines evaluated showed high bioavailability, high drugs score and low potential risk.

Duas séries de 4-aril-3-metil-1,2,3,4-tetrahidroquinolina foram sintetizadas de acordo com um método de síntese em duas etapas e avaliadas como potenciais agentes antifúngicos. O passo chave envolveu a formação dos correspondentes N-bencil tetrahidroquinolinas 5 via uma cicloadição de imino Diels-Alder catiónica. O segundo passo foi obter as N-tetrahidroquinolinas 6 através de uma desbenzilação catalítica. Os produtos foram purificados utilizando cromatografia em coluna. As substancias foram identificadas por ressonancia magnética nuclear (RMN), espectrometria de massa (EM) e espectroscopia de infravermelho (IR). Todos o compostos foram testados in vitro contra as estirpes padrao e os fungos clinicamente importantes, incluindo as leveduras, hialohifomicetes e dermatófitos. Estes estudos mostraram que entre a série de tetrahidroquinolinas (THQ) os compostos 6f e 6g mostraram atividade antifúngica, particularmente contra dermatófitos. O composto 6-metoxi-4-(4-hidroxi-3-metoxifenil)-3-metil-1,2,3,4-tetrahidroquinila 6g mostrou melhor atividade (MIC 32-65 μg/mL). Os resultados indicam que a remoção do grupo benzilo e a introdujo de um grupo hidroxilo no substituinte arilo do N-benzil-tetrahidroquinolina, resultou num aumento significativo da atividade antifúngica. Os resultados foram suplementados por previsöes in silico, que mostraram alta biodisponibilidade e pouco risco potencial da maioria dos tetrahidroquinolinas avaliados.

Os extratos, frações e ácido elágico, isolados da entrecasca de Lafoensia pacari A. St.-Hil., Lythraceae, foram testados in vitro para atividade antifúngica, frente a um painel de leveduras, hialo-hifomicetos e dermatófitos, utilizando o método de microdiluição. O extrato EtOH, frações e ácido elágico exibiram atividade contra Candida spp. e Saccharomyces cerevisiae com valores de CIM entre 250-1000 µg/mL, porιm não mostraram ação contra fungos filamentosos e dermatófitos (CIM>1000 µg/mL). Os extratos ativos foram avaliados nos ensaios de inibição do crescimento das hifas de Neurospora crassa, no teste do sorbitol, e pelo estudo do efeito do ergosterol na CIM do ácido elágico. Os extratos ativos, frações e ácido elágico mostraram zonas manchadas ao redor dos discos de papel e induziram malformações nas hifas. Além disso, a CIM do ácido elágico contra Saccharomyces cerevisiae passou de 62 para 250 µg/mL na presença do sorbitol 0,8 M, sugerindo que o ácido elágico provavelmente poderia exercer ação na parede celular fúngica. Esses resultados indicam que o ácido elágico pode ser o principal composto antifúngico de Lafoensia pacari, sugerindo que o modo de ação antifúngico desses extratos e ácido elágico poderia estar associado à inibição da parede celular fúngica.

Stem-bark extracts, fractions and the isolated constituent, ellagic acid of Lafoensia pacari St. Hil. (Lythraceae) were in vitro assayed for antifungal activity against a panel of yeasts, hialohyphomycetes as well as dermatophytes with the microbroth dilution method. The EtOH extract and its fractions and ellagic acid exhibited activity against Candida spp and Saccharomyces cerevisiae with MIC values between 250-1000 µg/mL, but they showed no action against filamentous fungi and dermatophytes (MIC>1000 µg/mL). Active extracts were evaluated in Neurospora crassa hyphal growth inhibition and sorbitol assays and then the effect of ergosterol on the MIC of ellagic acid was studied. The active extracts and its fractions and ellagic acid showed a blotchy zone around the paper disk and induced malformations of the hypha. Besides, MIC of the ellagic acid against the Saccharomyces cerevisiae was raised from 62 to 250 µg/mL in the presence of sorbitol 0.8 M, suggesting that the ellagic acid would probably exert its action on fungal cell wall. These results indicate that ellagic acid might be the main active antifungal compound of Lafoensia pacari and further suggest that the mode of antifungal action of these extracts and ellagic acid could be associated with the inhibition of fungal cell wall.

A síntese, a caracterização espectroscópica e os resultados biológicos de novas séries de 2-(4-piridil)-1,2,3,4-tetrahidroquinolinas e seus precursores, -N-aril-N-[1-(4-piridil)but-3-enil]aminas, são descritos. Foi encontrado que ambos, precursores substituídos γ-piridil e os produtos finais, as tetrahidroquinolinas, demonstraram excelentes atividades antifúngicas contra Aspergillus fumigatus, Aspergillus flavus, Aspergillus niger, Microsporum gypseun, Trichophyton rubrum e Trichophyton mentagrophytes.

Synthesis, spectral characterization and biological results of new series of 2-(4-pyridyl)-1,2,3,4-tetrahydroquinolines and their closer precursors, -N-aryl-N-[1-(4-pyridyl)but-3-enyl]amines are reported. It was found that both γ-pyridyl substituted precursors and final products, tetrahydroquinolines, showed very good antifungal activities against Aspergillus fumigatus, Aspergillus flavus, Aspergillus niger, Microsporum gypseun, Trichophyton rubrum and Trichophyton mentagrophytes.

As partes aéreas de seis plantas argentinas - conhecidas geralmente como "botões d'ouro" - são usadas indistintamente na medicina popular ou para obter remédios ervais e fitoterápicos. No entanto, estas entidades pertencem a três gêneros da tribo Helenieae (Asteraceae): Gaillardia, Helenium e Hymenoxys, sendo as espécies mais utilizadas Gaillardia megapotamica var. megapotamica (Spreng.) Bak.; G. megapotamica var. scabiosoides (Arn.) Bak.; G. megapotamica var. radiata (Griseb.) Bak.; Helenium donianum (Hook. & Arn.) Seckt; H. argentinum Ariza e Hymenoxys anthemoides (Juss.) Cass. Neste trabalho, foram estudadas as relações entre os táxons mencionados a partir do ponto de vista morfológico, a sua coexistência em populações naturais e suas ações farmacológicas reputadas. As suas características histológicas são descritas e ilustradas, a fim de obter uma exata identificação botânica dos produtos encontrados no mercado, de forma a garantir a sua qualidade, especialmente porque as amostras são freqüentemente já pulverizadas ou em pó.

The aerial parts of six Argentinean plants - commonly known as "botones de oro"- are indistinctly used either in folk medicine or to obtain herbal remedies and phytotherapics. However, these entities belong to three different genera of the Tribe Helenieae (Asteraceae): Gaillardia, Helenium and Hymenoxys, being the most used species Gaillardia megapotamica var. megapotamica (Spreng.) Bak.; G. megapotamica var. scabiosoides (Arn.) Bak.; G. megapotamica var. radiata (Griseb.) Bak.; Helenium donianum (Hook. & Arn.) Seckt; H. argentinum Ariza and Hymenoxys anthemoides (Juss.) Cass. In this work, we studied the relationships between the mentioned taxa from the morphological point of view, their coexistence in natural populations and their reputed pharmacological actions. Their histological features are described and illustrated, in order to obtain an accurate botanical identification of the products found in the market so as to guarantee their quality, especially because the samples are often already powdered or grounded.

Os extratos em hexano, diclorometano, acetato de etila e etanol das entrecascas de Bowdichia virgilioides, Calophyllum brasiliense, Cariniana rubra, Lafoensia pacari e Stryphnodendron obovatum, do rizoma de Simaba ferruginea e do látex de Croton urucurana foram triados contra um painel de bactérias e fungos usando o método de microdiluição em caldo. O látex de Croton urucurana foi o material derivado de planta com maior atividade antimicrobiana. Os extratos em acetato de etila e hexano da entrecasca de Calophyllum brasiliense destacaram-se por suas seletivas atividades antibacterianas. Os extratos polares da entrecasca de Lafoensia pacari notabilizaram-se por suas potentes e seletivas atividades contra leveduras e os extratos polares e não-polares de Bowdichia virgilioides por suas atividades antifúngicas contra hialo-hifomicetos e dermatófitos. Este é o primeiro relato mostrando atividades antifúngicas para os extratos de Cariniana rubra e Simaba ferruginea. Esse trabalho demonstrou a atividade antimicrobiana de plantas medicinais do Cerrado de Mato Grosso em ensaios in vitro e indica que elas podem ser potenciais candidatas para o desenvolvimento de novas estratégias no tratamento de infecções bacterianas e fúngicas.

Hexane, dichloromethane, ethyl acetate and ethanol extracts from stem barks of Bowdichia virgilioides, Calophyllum brasiliense, Cariniana rubra, Lafoensia pacari, and Stryphnodendron obovatum and rhizome of Simaba ferruginea and Dragon's blood red sap from Croton urucurana were screened against a panel of bacteria and fungi using the micro-broth dilution method. Dragon's blood from Croton urucurana was the most effective antimicrobial plant material. Ethyl acetate and hexane extracts of Calophyllum brasiliense stem bark deserved distinction by their selective antibacterial activity. Lafoensia pacari stem bark polar extracts distinguished by their potent and selective anti-yeast activity and Bowdichia virgilioides polar and non-polar extracts by their antifungal activity towards hyalohypho-mycetes and dermatophytes. This is the first report showing antifungal activity for polar extracts of Cariniana rubra and Simaba ferruginea. This study has demonstrated antimicrobial activity of Mato Grosso Cerrado ethnomedicinal plants in in vitro assays and has indicated that they can be effective potential candidates for the development of new strategies to treat fungal and bacterial infections.

Extracts from the Argentinean herb Tagetes mendocina Phil. (Asteraceae) were tested for antimicrobial activity against fungi, bacteria and protozoa. The different extracts (PE, DCM, MeOH and EtOAc) and the essential oil displayed activity mainly against dermatophytes, a group of fungi that produces skin infections. The bioassay-guided fractionation of PE, DCM and EtOAc extracts led to the isolation of eight compounds including two thiophenes, two acetophenone derivatives, dihydrorosefuran and three flavonoids. ITie thiophenes 5-(4-hydroxy- l-butynyl)-2,2'-bithienyl (BBTOH) (1) and its acetate (BBTOAc) (2) proved to be highly active against the dermatophytes Microsporum gypseum, Trichophyton rubrum and T. mentagrophytes with MIC values of 3.12, 3.12 and 6.25 µg/mL for compound 1 and 25, 3.12 and 6.25 µg/mLfor compound 2, respectively. In turn, the essential oil displayed a weak to modérate antifungal effect against M. gypseum with MIC = 250 µg/mL. ITie essential oil was examined by GC and GC-MS and 21 constituents (97.3%) were identified. (E) p-ocimene, (Z)-tagetone, (ii)-tagetone, (Z)-ocimenone, á-pinene and (E)-ocimenone were the major components. In addition, thiophenes 1 and 2 and 2-hydroxyacetophenone 3 showed antiprotozoal activity against Leishmania amazonensis, L. brasiliensis andi. infantum promastigotes with 100% lysis at 100 µg/mL.

A planta Plinia glomerata (Myrtaceae), popularmente conhecida como cabeludinha ou " jabuticaba-amarela" , ocorre amplamente no sul do Brasil e é cultivada como ornamental e frutífera comestível. O presente trabalho avaliou as propriedades antimicrobianas dos extratos, frações e substâncias puras isoladas da planta contra bactérias e fungos patogênicos. As concentrações inibitórias mínimas (CIM) foram determinadas através do método de diluição em ágar. As frações acetato de etila (AE) e fração aquosa (AQ) demonstraram a melhor atividade contra Staphylococcus aureus. A fração AQ também foi efetiva contra Escherichia coli. As substâncias puras, ácido 3,4,3’-trimetóxi-flavelágico-4’-O-glicosídeo e ácido 3,4,3’-trimetóxi-flavelágico foram inativas até a concentração de 500 µg/mL contra os microrganismos testados. Em relação aos resultados antifúngicos, os extratos metanólico (EM) e acetônico (EA) e a fração aquosa (AQ) mostraram boa atividade somente contra dermatófitos. Os resultados obtidos permitem concluir que a Plinia glomerata possui princípios ativos com ação antimicrobiana, sugerindo que outras substâncias da planta estão agindo contra os microrganismos indicados ou a existência de efeitos sinérgicos.

Plinia glomerata, commonly known as " yellow jaboticaba" or " cabelluda" occurs widely in south of Brazil. This work evaluated the antimicrobial properties of the extracts, fractions and isolated compounds of this plant against pathogenic microorganisms, bacteria and fungi. The minimal inhibitory concentration (MIC) was determined through the method of dilution in agar. The ethyl acetate (EtOAc) and aqueous fractions demonstrated the best activity against Staphylococcus aureus. The aqueous fraction also exhibited good activity against Escherichia coli. The pure substances 3,4,3’-trimethoxy-flavellagic-4’-O-glucose acid and 3,4,3’-trimethoxy-flavellagic acid were inactive up to 500 µg/mL. Regarding results against fungi, EA and EM extracts as well as AQ fraction showed good activity only against dermatophytes. The results suggest that P. glomerata produces active principles with antimicrobial activity, suggesting that other substances from the plant are acting against the microorganisms or the existence of synergic effects.

The essential oil of the aerial parts of Baccharis grisebachii was examined by GC and GC-MS and evaluated for its antimicrobial properties. Forty three essential oil constituents were identified representing 94.3% of the total. Thymol, thymol methyl ether, thymyl acetate, alpha pinene, alpha humulene, and globulol were found to be the major components. The oil showed MIC values < 250 μg/mL against Cryptococcus neoformans (125 μg/mL), Aspergillus spp. (125 μg/mL), and particulary against Trichophyton mentagrophytes and T. rubrum (62.5 μg/mL)

Alguns parâmetros são apresentados para o controle de qualidade de raízes de Pfaffia glomerata e Pfaffia paniculata, utilizando suas características botânicas e químicas. Realizou-se, também, um screening farmacológico de P. glomerata direcionado às atividades relacionadas com seu uso como "tônico". O extrato etanólico das raízes de P. glomerata não apresentou atividade antiviral, antiproliferativa, antifúngica ou atividade inibitória de monoaminoxidases. A avaliação da citotoxicidade determinou que a CI50 é > 2.000 µg/mL. As principais características morfológicas e micrográficas das raízes de P. glomerata e P. paniculata descritas permitem auxiliar na sua identificação segura.

Some parameters for the quality control of P. glomerata and P. paniculata roots using their botanical and chemical characteristics are presented. It was also carried out an in vitro pharmacological screening to evaluate some biological properties of P. glomerata that could be related to its popular use as "tonic". Relating to biological assays, ethanolic extract from P. glomerata roots did not present antiviral, antiproliferative, antifungal or MAO inhibitory activities. The cytotoxicity evaluation of P. glomerata determined that IC50 is >2,000 µg/mL. The main morphological and micrographic characteristics of P. glomerata and P. paniculata roots are described in this paper in order to aid in their unequivocal identification.