Sinningia reitzii (Hoehne) L. E. Skog (Gesneriaceae) is a subshrub native to Brazil, where it is distributed in two disjunctive populations around the 26°S and 23°S parallels. In this work, tubers of plants from the wild population growing at the 26°S parallel (Santa Catarina state) yielded two new naphthoquinones, 5,6-dihydroxy-7-methoxy-a-dunnione and 8-hydroxy-6,7-dimethoxy-a-dunnione. Three known compounds were also isolated: 6,8-dihydroxy-7-methoxy-a-dunnione, 5-hydroxy-6,7-dimethoxy-a-dunnione, and 6,8-dihydroxy-7-methoxy-2-O-methyldunniol. The naphthoquinones 6,8-dihydroxy-7-methoxy-2-O-methyldunniol, 6,8-dihydroxy-7-methoxy-a-dunnione, and 5,6-dihydroxy-7-methoxy-a-dunnione displayed antioxidant activity in the ORAC-FL method, with values of relative trolox equivalent in the range of 1.39-4.83 mmol g-1.

Phytochemical study of aerial parts from Sinningia mauroana Chautems (Gesneriaceae) yielded 17 known compounds: sitosterol, stigmasterol, betulinic acid, oleanolic acid, hederagenin, maslinic acid, ursolic acid, pomolic acid, soranjidiol, methyl 4-hydroxyphenylacetate, 6-hydroxy-7-methoxy-α-dunnione, 7-hydroxy-6-methoxy-α-dunnione, jacaranone, calceolarioside A, conandroside, luteolin, and luteolin-7-O-glucoside. Complete NMR data of 6-hydroxy-7-methoxy-α-dunnione and 7-hydroxy-6-methoxy-α-dunnione were obtained in two different solvents. Hexane, ethyl acetate and ethanol extracts were screened for antimicrobial, antioxidant and cytotoxic activities. The antimicrobial activity was assayed against Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, C. parapsilosis, C. dubliniensis, and C. glabrata, using the microdillution method. All extracts were inactive (MIC > 100 µg mL-1). The antioxidant activity was evaluated with the ORAC method; the ethyl acetate and ethanol extracts were active (TE relative > 800 µg g-1). The cytotoxic activity was tested against PC-3 (prostate) and SKMEL-103 (melanoma) human tumor cell lines, and 3T3 fibroblast cell line, using the MTT assay. The hexane extract showed strong activity against PC-3 and SKMEL-103 human tumor cell lines (IC50 < 0.25 and 3.07 µg mL-1, respectively), and a lower activity towards 3T3 fibroblasts (IC50 = 6.84 µg mL-1). The other extracts were inactive (IC50 > 50 µg mL-1).

Phytochemical study of Sinningia reitzii (Gesneriaceae) led to the isolation of three new naphtoquinones, 6,7-dimethoxydunnione, 7-hydroxy-6-methoxydunnione, and 5-hydroxy-6,7-dimethoxydunnione from the tubers, together with four known compounds, 7-hydroxydunnione, 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione, and 8-hydroxydeydrodunnione. Aerial parts furnished five known compounds, 5-hydroxy-6,7-dimethoxydunniol, 6,8-dihydroxy-7-methoxy-2-O-methyldunniol, loureirin B, jacaranone, and methyl 4-hydroxyphenylacetate. Compounds 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione, 8-hydroxydeydrodunnione, 5-hydroxy-6,7-dimethoxydunniol and 6,8-dihydroxy-7-methoxy-2-O-methyldunniol had been previously reported in the tubers of S. reitzii. Density functional theory was used to assign the absolute configuration of compounds 6,7-dimethoxydunnione, 7-hydroxy-6-methoxydunnione 5-hydroxy-6,7-dimethoxydunnione, 7-hydroxydunnione, 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione. Compounds 6,7-dimethoxydunnione, 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione and 8-hydroxydeydrodunnione were evaluated for cytotoxicity against PC3 (prostate), SKMEL 103 (melanoma), and HeLa (cervix) human cancer, and 3T3 fibroblast cell lines, using the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. Compound 6,7-dimethoxydunnione displays cytotoxic activity against all the tumor cell lines tested (half maximal inhibitory concentration, IC50, 4.47-26.2 µmol L-1), and was inactive against 3T3 fibroblasts (IC50 > 100 µmol L-1). Compounds 8-hydroxydunnione, 5-hydroxy-6,7-dimethoxy-α-dunnione and 8-hydroxydeydrodunnione were inactive against all tested cell lines.

Chemical investigation of Sinningia warmingii (Gesneriaceae) tubers lead to the isolation of two new dimeric naphthoquinone derivatives, named warmingiins A and B, besides six known compounds, aggregatin E, aggregatin F, tectoquinone, halleridone, cleroindicin B, and cornoside. All compounds were identified by spectroscopic analysis, mainly nuclear magnetic resonance (NMR) and mass spectrometry (MS), and comparison with the literature. The structure of the warmingiin A, which is an artifact of warmingiin B, was confirmed by X-ray diffraction analysis. Antimicrobial activity of the ethanolic extract and fractions of S. warmingii was evaluated against Staphylococcus aureus, S. epidermidis, Escherichia coli, Pseudomonas aeruginosa, Candida albicans, C. dubliniensis, C. glabrata and C. parapsilosis. All samples were inactive.

ABSTRACT This study aimed to further investigate the cytotoxicity against tumor cell lines and several bacterial strains of Annona squamosa and its mode of action. Methanol extracts of A. squamosa leaves (ASL) and seeds (ASS) were used. ASL showed significant antibacterial activity against S. aureus, K. pneumoniae and E. faecalis with MIC values of 78, 78 and 39 µg/mL respectively. Moreover, ASL exhibited significant biofilm disruption, rapid time dependent kinetics of bacterial killing, increased membrane permeability and significantly reduced the cell numbers and viability. Regarding the cytotoxicity against tumor cell lines, ASS was more active against Jurkat and MCF-7 cells, with CI50 1.1 and 2.1 µg/mL, respectively. ASL showed promising activity against Jurkat and HL60, with CI50 4.2 and 6.4 µg/mL, respectively. Both extracts showed lower activity against VERO cells and reduced the clonogenic survival at higher concentrations (IC90) to MCF-7 and HCT-116 lineages. The alkaloids anonaine, asimilobine, corypalmine, liriodenine nornuciferine and reticuline were identified in extracts by UPLC-ESI-MS/MS analysis. This study reinforced that A. squamosa presents a remarkable phytomedicinal potential and revealed that its antimicrobial mechanism of action is related to bacterial membrane destabilization.

Polycarpol, a recurrent lanostane-type triterpene in Annonaceae family, was confirmed by thin layer chromatography and mass spectrometry analysis in the aerial parts (twigs and trunk barks) of Unonopsis duckei R.E. Fr., U. floribunda Diels, U. rufescens(Baill.) R.E. Fr., U. stipitata Diels, Onychopetalum amazonicum R.E. Fr. and Bocageopsis pleiospermaMaas. Its chemotaxonomic significance was discussed for these three genera, as well for the Annonaceae family. In addition, the antimicrobial activity against several strains of microorganisms was evaluated for the first time for this compound, being observed significant antibacterial activity against Staphylococcus aureus (ATCC 6538), Staphylococcus epidermidis (ATCC 1228) and Escherichia coli (ATCC 10538 and ATCC 10799) with minimal inhibitory concentration values between 25 and 50 μg ml−1.

Phytochemical study of the flowers of Gochnatia polymorpha subsp. floccosa, Asteraceae, yielded eleven known triterpenes identified as lupeol, lupeyl acetate, lupeyl palmitate, taraxasterol, taraxasteryl acetate, pseudotaraxasterol, pseudotaraxasterol acetate, α-amyrin, α-amyryl palmitate, β-amyrin and β-amyryl palmitate, along with sitosterol, stigmasterol, palmitic and stearic acids. These compounds are been reported for the first time in the species. The compounds were identified by analysis of NMR spectra (¹H, 13C and DEPT), GC-MS and comparison with literature data. Previous work have reported the isolation of triterpenes, diterpenes, sesquiterpenes, flavonoids, coumarins and phenolic compounds from aerial parts and roots from G. polymorpha.

Os extratos brutos e oito constituintes isolados de Chresta scapigera foram avaliados para as atividades antibacteriana e antifúngica, utilizando o método de difusão em ágar. Vinte cepas indicadoras, incluindo bactérias (Gram-positivas e Gram-negativas) e leveduras, foram utilizadas no bioensaio. Os melhores resultados foram obtidos para os extratos hexânicos, enquanto os extratos etanólicos não inibiram o crescimento microbiano. Acetato de b-amirina, tilirosídeo e luteolina foram os mais eficazes dentre os constituintes avaliados.

Crude extracts and eight isolated compounds from Chresta scapigera were evaluated for antibacterial and antifungal activities by the agar-well diffusion method. Twenty strains, including Gram-positive and Gram-negative bacteria and yeasts were used in the bioassay. Hexane extracts presented the best results while ethanol extracts did not indicate inhibition of the microbial growth. Amongst the evaluated compounds b-amyrin acetate, tiliroside and luteolin showed the strongest antimicrobial effect.

Neste estudo procedeu-se a avaliação da atividade antimicrobiana e citotóxica de extratos de Gochnatia polymorpha ssp floccosa, espécie empregada na medicina popular contra doenças respiratórias. Folhas, cascas do tronco e ramos foram extraídos com hexano, diclorometano e etanol, sucessivamente, sendo obtidos os respectivos extratos brutos. A atividade antimicrobiana foi determinada pelo método de difusão em ágar utilizando-se bactérias Gram-positivas, Gram-negativas e fungos. A avaliação da citotoxicidade foi realizada empregando-se o ensaio de letalidade contra Artemia salina. Nenhum dos extratos mostrou atividade citotóxica. Os extratos das folhas apresentaram uma fraca atividade antimicrobiana frente a algumas cepas de Staphylococcus aureus e Streptococcus mutans, enquanto o extrato em diclorometano dos ramos e o extrato em etanol das cascas foram ativos contra Micrococcus luteus, Staphylococcus aureus e S. epidermidis. A maior atividade antimicrobiana foi observada para o extrato em diclorometano das cascas, que inibiu o crescimento de Micrococcus luteus, Staphylococcus aureus, S. epidermidis, Streptococcus mutans, Enterococcus faecalis e Candida albicans. Esta atividade parece estar relacionada à presença de diterpenos no extrato. Nenhum dos extratos estudados (a 5,0 mg/mL) mostrou atividade frente a cepas de bactérias Gram-negativas. Esses resultados demonstram o potencial dessa planta como fonte de compostos antibacterianos e justificam, parcialmente, seu uso popular.

The antimicrobial and cytotoxic activities of Gochnatia polymorpha ssp floccosa, a medicinal plant used against respiratory diseases, were evaluated. Successive petroleum ether, dichloromethane and ethanol extracts of dried leaves, trunk bark and stems were used in the brine shrimp lethality bioassay and tested against 22 strains of microorganisms (Gram-positive and Gram-negative bacteria and fungi) by the well-diffusion agar method. None of the extracts showed cytotoxicity on the brine shrimp bioassay. The extracts of leaves showed a mild activity against some strains of Staphylococcus aureus and Streptococcus mutans. The ethanol extracts of trunk bark and dichloromethane extract of stems also showed activity against Micrococcus luteus, Staphylococcus aureus and S. epidermidis. The highest activity was found in the dichloromethane extract of trunk bark, which showed significant antibacterial and antifungal activities against Micrococcus luteus, Staphylococcus aureus, S. epidermidis, Streptococcus mutans, Enterococcus faecalis and Candida albicans. Diterpenes are present in this extract and could be responsible for the activity. All the screened extracts were shown to be inactive (at 5.0 mg/mL) against strains of Gram-negative bacteria tested. These results indicate the potential of G. polymorpha ssp floccosa as a source of antibacterial compounds and partly support the use of this plant in folk medicine.

Neste estudo procedeu-se a avaliação da atividade antibacteriana e antifúngica dos extratos brutos de Alternanthera maritima (Amaranthaceae) planta in natura de duas coletas distintas e obtidos por cultura de células buscando-se averiguar a manutenção da atividade antimicrobiana dos extratos obtidos da planta in vivo e in vitro. A ação antibacteriana e antifúngica foi determinada pelo método de difusão em ágar (técnica do poço) utilizando-se trinta cepas de microrganismos indicadores (bactérias Gram-positivas e Gram-negativas, leveduras e dermatófitos). Todos os extratos obtidos com solventes orgânicos avaliados apresentaram-se bioativos com halos de inibição de 6 a 20 mm. Os extratos da planta in natura das duas coletas (Restinga de Marica (RJ), verão de 1995 e 1998) inibiram o desenvolvimento de diferentes microrganismos (bactérias, leveduras e dermatófitos). Os extratos obtidos da cultura de calos desenvolvidos em duas condições de cultivo diferentes, também se mantiveram bioativos. Assim, os resultados obtidos encorajam a realização de novos estudos com esta espécie vegetal para se determinar quais as substâncias presentes nos extratos e que contribuem para a atividade biológica, como também para entender seu mecanismo de ação e avaliar sua toxicidade, visando uma possível aplicação farmacêutica.

The aim of this study was to evaluate the antibacterial and antifungal activity of callus culture (two different hormonal combination culture medium) and adult plants (two collect) extracts from Alternanthera maritima (Amaranthaceae) investigating the maintenance of antimicrobial activity in vivo and in vitro. The antibacterial and antifungal activity was determined by the agar-well diffusion method against thirty strains of microorganisms including Gram-positive and Gram-negative bacteria, yeasts and dermatophytes. All the organic crude extracts studied were bioactive. Extracts of aerial parts and roots of adult plants collected during the same period of years of 1995 and 1998 (Restinga de Maricá (RJ), collect 1 and 2) inhibited the growth of several microorganisms (bacteria, yeasts and dermatophytes) with inhibition halo between 6 and 20 mm. Plant cell callus culture extracts obtained from two culture conditions were also bioactive. Thus, the positive results suggest that the A. maritima extracts should be further studied to determine the bioactive chemical compounds as well as to understand the possible mechanisms of action and evaluate their toxicity looking toward a pharmaceutical employment.