ABSTRACT Operculina macrocarpa (L.) Urb., Convolvulaceae, is used by the population as a laxative. In this work we described the isolation of the three phenolic acids present in the hydroethanolic extract of the O. macrocarpa roots. The quantification of the caffeic, chlorogenic acids and of the new caffeic dimer in the hydroethanolic and infusion extracts was performed by high-performance liquid chromatography coupled photodiode array detector. These analyses showed the higher content of the chlorogenic, caffeic and the new 3,4'-dehydrodicaffeic acid in hydroethanolic and hydroethanolic extracts without resin in which infusion. The acid found in greater quantity is caffeic acid followed by the 3,4'-dehydrodicaffeic acid. The laxative activity was evaluated by different experimental models of intestinal transit with the hydroethanolic and infusion extracts, and the resin fraction, caffeic, chlorogenic and ferulic acids. The results showed all extracts and compounds tested had significant activity in the experimental model tested. These results obtained are essential for the future development of a pharmaceutical product with safety and efficacy.

Espécies de Byrsonima, família Malpighiaceae, são popularmente conhecidas como "murici". Existem várias propriedades atribuídas às folhas de espécies de Byrsonima incluindo febrífuga, no tratamento de disfunções gastrintestinais e doenças de pele. Neste trabalho avaliamos a atividade antimicrobiana dos extratos das folhas de Byrsonima fagifolia, B. basiloba e B. intermedia usando o método de difusão em disco. Os resultados obtidos mostraram que os extratos metanólicos das folhas apresentaram atividade antimicrobiana contra todos os microrganismos testados.

Byrsonima species, family Malpighiaceae, is popularly known as "murici". There are several properties attributed to the leaves of Byrsonima species including febrifuge, to treat gastrointestinal dysfunctions and skin diseases. In this work, the antimicrobial activity of Byrsonima fagifolia, B. basiloba and B. intermedia extracts obtained from the leaves were evaluated by using the disc-diffusion method. The results obtained showed that the methanol extracts of leaves had presented antimicrobial activity against all the microorganisms tested.

We evaluated the potential antitubercular activity of triterpenes obtained from leaves and bark of Byrsonima crassa. From chloroform extracts of the leaves, by bioassay-guided fractionation, we obtained mixtures of known triterpenes: α-amyrin, β-amyrin and their acetates, lupeol, oleanolic acid, ursolic acid and α-amyrinone. Tested against Mycobacterium tuberculosis, the triterpenes exhibited minimum inhibitory concentrations (MICs) of 31.25 - 312.25 µg/mL. β-amyrin and friedelin, isolated from the chloroform extract of bark, showed MICs of 312.25 and 125 µg/mL respectively. This is the first report of the identification and determination of the activity of B. crassa triterpenes against M. tuberculosis.

A análise dos extratos das raízes de L. montanus A.M.G. Azevedo resultou no isolamento de vinte e três compostos principalmente flavonóides dos quais cinco são descritos pela primeira vez. As estruturas moleculares dos novos compostos (1-5) foram propostas através da análise dos espectros de UV, IV, EM e RMN como sendo: 2'-hidroxi-8-(<FONT FACE=Symbol>a, a</FONT>-dimetilalil)-2", 2"-dimetilpirano-(5", 6":3',4')-dibenzoilmetano (1), 2'-metoxi-8-(<FONT FACE=Symbol>a,a</FONT>-dimetilalil)-2", 2"-dimetilpirano-(5", 6":3',4')-dibenzoilmetano (2), 4'-metoxi-2", 2"-dimetilpirano-(5", 6":8,7)-flavona (3), 2"-(1-hidroxi-1-metiletil)-furano-(4", 5":8,7)-flavona (4) e [2'-metoxi-furano(4", 5":3',4')-fenil]-fenilmetanona (5). Adicionalmente quinze ácidos graxos foram detectados através da análise de CG-EM dos ésteres metílicos correspondentes [(CH3)2CH(CH2)8COOH e CH3(CH2)nCOOH (n = 6, 12-24)]. A análise quantitativa por CLAE mostrou que os flavonóides mais abundantes nos extratos éter de petróleo e diclorometânico foram pongamol (19%) e lanceolatina B (8.0%), respectivamente. Nos ensaios de bioautografia, os extratos, pongamol (9), laceolatina B (10), isolonchocarpina (14), derriobtusona A (17) e medicarpina (18) foram ativos contra Staphilococcus aureus enquanto 9, também contra Bacillus subtilis e Cladosporium cladosporióides. O composto 1, 2", 2"-dimetilpirano-(5", 6":8,7)-flavona (11) e furano-(2", 3":7,8)-4'-metoxiflavona (12) foram ativos contra Fusarium oxysporium, enquanto 11, também contra Rhizopus oryzae. Os extratos assim como os compostos 9, 10, 17 e (E)-7-O-metoxipongamol (23) apresentaram alta toxicidade no ensaio de letalidade com Artemia salina.

The analysis of root extracts from Lonchocarpus montanus A.M.G. Azevedo resulted in the isolation of twenty three compounds chiefly flavonoids of which five (four flavonoids and one benzophenone) are described for the first time. The molecular structures of the new compounds (1-5) were determined through spectral analysis (UV, IR, MS and NMR) as being: 2'-hydroxy-8-(<FONT FACE=Symbol>a,a</FONT>-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane (1), 2'-methoxy-8-(<FONT FACE=Symbol>a, a</FONT>-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3',4')-dibenzoylmethane (2), 4'-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-flavone (3), 2"-(1-hydroxy-1-methylethyl)-furano-(4",5":8,7)-flavone (4) and [2'-methoxy-furano-(4",5":3',4')-phenyl]-phenylmethanone (5). Additionally, fifteen fatty acids were detected through GC-MS analysis of the corresponding methyl esters [(CH3)2CH(CH2)8COOH and CH3(CH2)nCOOH (n = 6, 12-24)]. Quantitative RP-HPLC showed that the most abundant flavonoids in the petroleum ether and dichloromethane extracts were pongamol (19%) and lanceolatine B (8.0%), respectively. In the bioautography assay, the extracts, pongamol (9), lanceolatine B (10), isolonchocarpin (14), derriobtusone A (17) and medicarpine (18) were active against Staphilococus aureus whereas 9 also against Bacillus subtilis and Cladosporium cladosporioides. Compound 1, 2",2"-dimethylpyrano-(5",6":8,7)-flavone (11) and furano-(1200,1300:7,8)- 4'-methoxy flavone (12) were active against Fusarium oxysporium whereas 11 also against Rhizopus orizae. The extracts, compounds 9, 10, 17 and (E)-7-O-methoxypongamol (23) displayed high toxicity in the brine shrimp lethality assay.

Neea theifera Oerst. (Nyctaginaceae) é amplamente utilizada na medicina popular brasileira para tratamento de úlceras gástricas e inflamação. A investigação fitoquímica das folhas de Neea theifera permitiu o isolamento e identificação da nova flavona luteolina-7-O-[2''-O-(5'''-O-feruloil)- beta-D-apiofuranosil]-beta-D-glucopiranosídeo (1) além dos oito compostos conhecidos vitexina, isovitexina, isoorientina, orientina, vicenina-2, crisoeriol, apigenina e luteolina. A identificação química foi realizada por métodos espectroscópicos incluindo RMN-2D, bem como análises no UV e IES-EM.

Neea theifera Oerst. (Nyctaginaceae) is widely used in Brazilian folk medicine for the treatment of gastric ulcers and inflammation. Phytochemical investigation of the leaves of Neea theifera afforded the isolation of the new flavone luteolin-7-O-[2''-O-(5'''-O-feruloyl)- beta-D-apiofuranosyl]-b-D-glucopyranoside (1) besides the eight-known compounds vitexin, isovitexin, isoorientin, orientin, vicenin-2, chrysoeriol, apigenin and luteolin. Their chemical identification was established by NMR spectroscopic methods including 2D-NMR, as well as UV and ESI-MS analyses.

High-speed counter-current chromatography (HSCCC) is a major tool for the fast separation of natural products from plants. It was used for the preparative isolation of the flavonoid monoglucosides present in the aerial parts of the Davilla elliptica St. Hill. (Dilleniaceae). This species is used in Brazilian folk medicine for the treatment of gastric disorders. The optimum solvent system used was composed of a mixture of ethyl acetate-n-propanol-water (140:8:80, v/v/v) and led to a successful separation of quercetin-3-O-alpha-L-rhamnopyranoside and myricetin-3-O-alpha-L-rhamnopyranoside in approximately 3.0 hours with purity higher than 95%. Identification was performed by ¹H NMR, 13C NMR and HPLC-UV-DAD analyses.

Este trabalho apresenta o estudo de substâncias apolares obtidas a partir de plantas pertencentes ao gênero Paepalanthus Mart. (Eriocaulaceae). Hidrocarbonetos alifáticos de cadeias longas lineares foram identificados por CG-DIC e CG-EM. Os resultados indicam que as espécies de Paepalanthus subg. Platycaulon apresentam perfil homogêneo, com cadeias carbônicas de n-alcanos variando de C25 a C31, com a maioria das amostras apresentando freqüências maiores dos homólogos C27 e C29. As espécies do subgênero Paepalocephalus podem ser diferenciadas pela distribuição dos n-alcanos principais. P. macrocephalus, uma espécie da subseção Aphorocaulon, apresenta perfil com alcanos de cadeia ímpar, enquanto P. denudatus e P. polyanthus, espécies da seção Actinocephalus, apresentam perfil bem distinto, com grande número de cadeias mais curtas e alta freqüência de cadeias com número par de carbonos, especialmente P. polyanthus. Os resultados obtidos indicam que a distribuição de nalcanos pode ser útil como caráter taxonômico, assim como as substâncias mais polares, como os flavonóides glicosilados.

This work presents the study of nonpolar compounds from plants belonging to the genus Paepalanthus Mart. (Eriocaulaceae). Long-chain linear aliphatic hydrocarbons were identified by GC-FID and GC-MS. The results indicate that Paepalanthus subg. Platycaulon species present a very homogenous profile, with carbon chains of n-alkanes ranging from C25 to C31, most samples presenting higher frequencies of C27 and C29 homologues. Paepalanthus subg. Paepalocephalus species may be distinguished from one another by the distribution of main n-alkanes. P. macrocephalus, subsect. Aphorocaulon species, presents alkanes with odd-carbon numbers and P. denudatus and P. polyanthus, Actinocephalus species, present alkanes with quite distinctive profiles, with many shorter chains and a high frequency of even-carbon number, especially P. polyanthus. The results obtained indicate that the distribution of alkanes can be a useful taxonomic character, as do polar compounds like flavonoid glycosides.

Folhas e cascas de algumas especies do gênero Byrsonima (Malpighiaceae) são empregadas popularmente contra diarréia. Contudo, não existem dados na literatura à respeito de investigacões químicas ou farmacológicas dos extratos de B. cinera. Neste estudo, nós avaliamos a atividade antidiarreica dos extratos metanólico e hidrometanólico das folhas de B. cinera em ratos Swiss. Os resultados mostraram que ambos os extratos reduziram signitivamente a motilidade intestinal. Investigacão fitoquímica do extrato metanólico levou ao isolamento e identificacão da (+)-catequina e da quercetina-3-O-a-L-arabinopiranosídeo. A atividade observada pode estar correlacaionada com a presença dessas substâncias nos extratos.

Leaves and bark of some Byrsonima species (Malpighiaceae) are popularly employed against diarrhoeal diseases. However, no data were reported in the literature about the chemisty and pharmacology of extracts from B. cinera leaves. In the present study we evaluated the anti-diarrhoeal activity of methanolic and hydromethanolic extracts obtained from the leaves of B. cinera in Swiss mice. Results showed that both extracts reduced significantly the gastrintestinal motility. Phytochemical evaluation of the methanolic extract led to the isolation and identification of (+)-catechin and quercetin-3-O-a-L-arabinopyranoside. The observed activity may be correlated to the presence of these compounds in the extract.

Do extrato etanólico dos capítulos de Paepalanthus microphyllus, isolou-se um derivado do ácido cafeico (1). Sua estrutura foi caracterizada por métodos espectroscópicos (RMN mono e bi-dimensionais) e por espetrometria de massas Electrospray. Foram, também, isolados outros três flavonóides (2-4) de interesse taxonômico, os quais foram identificados por métodos espectroscópicos e comparados com dados da literatura.

From the ethanolic extract of the capitulae of Paepalanthus microphyllus, one caffeic acid derivative (1) was isolated. The structure of the compound was characterized by spectroscopic methods, mainly 1D and 2D NMR experiments, as well as ESMS spectrometry. In addition, three flavonoids of taxonomic relevance were isolated and identified by comparison to literature data.

Nosso interesse quimiotaxonômico sobre Neoraputia nos estimulou a examinar N. paraensis, visando a busca de alcalóides. As frações foram monitoradas via RMN ¹H e ESI-EM/EM e foram analisadas somente aquelas cujos espectros apresentavam características de alcalóides do ácido antranílico e flavonóides não isolados anteriormente. Foram isolados do caule os alcalóides flindersina, skimmianina, 8-metoxiflindersina e dictamnina; das folhas os flavonóides 3',4',7,8-tetrametoxi-5,6-(2",2"-dimetilpirano)-flavona, 3',4',5,7,8-pentametoxiflavona, 5-hidroxi-3',4',6,7-tetrametoxiflavona, 3',4'-metilenodioxi-5,6,7-trimetoxiflavona e 5-hidroxi-3',4'-metilenodioxi-6,7-dimetoxiflavona,. Os alcalóides do ácido antranílico não foram encontrados em dez anos. Vários flavonóides isolados de N. paraensis, N. magnifica, Murraya paniculata, enxerto de Citrus sinensis (Rutaceae) e Lonchocarpus montanus (Leguminosae) foram testados frente a gliceraldeído-3-fosfato desidrogenase de Trypanosoma cruzi, visando verificar seus potenciais em inibir a atividade da enzima. Os flavonóides polimetoxilados e um isoflavonóide foram os mais ativos.

Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by ¹H NMR and ESI-MS/MS and only those which showed features of anthranilate alkaloids and flavonoids absent in the previous investigations were examined. Stems afforded the alkaloids flindersine, skimmianine, 8-methoxyflindersine and dictamnine; leaves yielded 3',4',7,8-tetramethoxy-5,6-(2",2"-dimethylpyrano)-flavone, 3',4',5,7,8-pentamethoxyflavone, 5-hydroxy-3',4',6,7-tetramethoxyflavone, 3',4'-methylenedioxy-5,6,7-trimethoxyflavone and 5-hydroxy-3',4'-methylenedioxy-6,7-dimethoxyflavone. The alkaloids have remained undiscovered for 10 years. A number of flavonoids isolated from N. paraensis, N. magnifica, Murraya paniculata, Citrus sinensis graft (Rutaceae), Lonchocarpus montanus (Leguminosae) were evaluated for their ability to inhibit the enzymatic activity of the protein glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi. Highly oxygenated flavones and isoflavone were the most actives.