Considering the relevance of natural products to the development of new drugs, this study focuses on the species Sida rhombifolia (L.), Malvaceae, widely used as a traditional remedy in several countries. The species is used to treat several diseases such as fevers, skin diseases, stomach pain, diarrhea, gum infection, conjunctivitis, urinary infections and inflammation. Many researchers around the word have investigated its pharmacological potential, and many uses have been confirmed. In spite of that, the phytochemical composition of its extracts is still poorly investigated. This research aims to make advances on the understanding of the constituents of S. rhombifolia identifying its alkaloidal compounds using ultra-high performance liquid chromatography coupled to mass spectrometry (UPLC-QTOF-MS/MS). By analyzing its alkaloidal fraction, it was possible to identify: 11-cryptolepine carboxylic acid (1), cryptolepine (2), quindoline (3), 11 methoxyquidoline (4), quindolinone (5), cryptolepinone (6), and 11-quindoline methyl ester (7). The alkaloids 1 and 7 are being reported for the first time from Sida genus. Based on the antimicrobial potential of cryptolepinone-type alkaloids, we prepared by semi-synthesis two cryptolepinone derivatives: 10-methylcryptolepinone (8) and the unreported compound 10-ethylcryptolepinone (9). Both derivatives were tested against fungal and bacterial strains and 10-methylcryptolepinone (8) showed strong activity against Cryptococcus neoformans, Candida albicans, Candida tropicalis, Aspergillus fumigatus and Aspergillus flavus.

Resumo A tribo Bignonieae, com aproximadamente 393 espécies, representa a maior tribo. A maioria dos membros de Bignonieae é de lianas com gavinhas, embora alguns arbustos também estejam incluídos. O Pico do Jabre está localizado a 1.197 m de altitude, representando o ponto com maior altitude no estado da Paraíba (Brasil) e uma área de extrema importância biológica. Neste estudo realizamos um inventário da tribo Bignonieae no Pico do Jabre em diferentes altitudes (700–1.200 m). Documentamos oito gêneros e 13 espécies, a maioria lianas, exceto Tanaecium parviflorum que é um arbusto. Os gêneros mais diversos na área são: Tanaecium (3 spp.), Amphilophium (2 spp.), Bignonia (2 spp.) e Xylophragma (2 spp.). Os gêneros Anemopaegma, Cuspidaria, Dolichandra e Pyrostegia estão representados por uma espécie cada. Seis espécies são novos registros para o Pico do Jabre (i.e., B. ramentacea, B. sciuripabulum, T. cyrtanthum, T. dichotomum, Xylophragma harleyi e X. heterocalyx). Tanaecium cyrtanthum, X. harleyi e X. heterocalyx constituem novos registros para o estado da Paraíba. Antes deste estudo, Xylophragma heterocalyx era apenas conhecida apenas do espécime tipo, coletado em Minas Gerais, representando um novo registro para o domínio fitogeográfico da Caatinga. O alto número de novos registros encontrados neste estudo indica a importância de estudos florísticos regionais para a documentação de novas ocorrências.

Abstract The tribe Bignonieae with approximately 393 species, represents the largest tribe of Bignoniaceae. Most members of Bignonieae are tendrillate lianas, although some shrubs are also found within this clade. The Pico do Jabre, located at 1,197 m of altitude, represents the highest mountain in the state of Paraíba (Brazil) and an area of extreme biological importance. We conducted an inventory of the Bignonieae from the Pico do Jabre. We documented eight genera and 13 species, only Tanaecium parviflorum is a shrub. The most diverse genera recorded are: Tanaecium (3 spp.), Amphilophium (2 spp.), Bignonia (2 spp.) and Xylophragma (2 spp.). Anemopaegma, Cuspidaria, Dolichandra and Pyrostegia are represented by a single species each. Six species are new records for the region (i.e., Bignonia ramentacea, B. sciuripabulum, Tanaecium cyrtanthum, T. dichotomum, Xylophragma harleyi and X. heterocalyx). Tanaecium cyrtanthum, X. harleyi and X. heterocalyx are new records for the state of Paraíba. Prior to this study, Xylophragma heterocalyx was only known from the type specimen, from Minas Gerais, representing a new record for the Caatinga. The high number of new records found in this study highlights the importance of regional floristic inventories for the documentation of new species occurrences.

A chemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith, a member of Annonaceae family, was carried out. The ethanolic extract from the roots of this plant led, by chromatography tecniches, to isolation of the new azaphenanthrene alkaloids dolichocarpine (1) and 9-methoxyeupolauramine (2), besides the known alkaloids eupolauramine (3), 3-methoxyeupolauridine (4), eupolauramine (5) and 4-methylsampangine (6). The structures of isolated compounds were established by 1D and 2D NMR, HRESIMS, tandem MSn and IR data. The cytotoxicity of compounds 1 - 5 was evaluated against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) cell lines.

Abstract The species Waltheria viscosissima A.St.–Hil, Malvaceae, which is known as ‘malva-branca', is traditionally used in the Brazilian northeast for the treatment of coughs. This research looks towards reporting the isolation of phytoconstituents of W. viscosissima, as well as the quantification of its phenolics, total flavonoid content, and free radical scavenging potential, along with an evaluation of its larvicidal activity against Aedes aegypti larvae. Chromatographic techniques were used to isolate the compounds and a structural elucidation was performed by 1D and 2D NMR. The quantification of total phenolics and flavonoids and the DPPH˙ radical scavenging activity was determined through spectrophotometric methods. Consequently, the phytochemical investigation led to the identification of fourteen compounds from the aerial parts of the W. viscosissima: steroids, triterpenes, alkaloids, and eight flavonoids previously reported in the literature. The quantification of compounds showed that the aerial parts extract possessed high concentration of flavonoids, while the roots extract were rich in other phenolic compounds. At the DPPH˙ free radical scavenging assay, the roots extract presented EC50 = 77.32 ± 4.37 µg/ml and the aerial parts extracts showed EC50 = 118.10 ± 1.21 µg/ml. W. viscosissima roots extract showed the most potent larvicidal activity against Ae. aegypti (LC50 = 4.78 mg/ml), with the potential of being used in effective and economically viable preparations that can be catered for domestic use towards controlling the vector insect of severe diseases, such as dengue and Zika.

Abstract Bauhinia L. and Schnella (Raddi.) Wund. are popularly known in Brazil as "mororó". The leaves and stem bark are used in folk medicine for various purposes, especially against diabetes. Morphoanatomical studies of the leaves of Bauhinia cheilantha (Bong.) Steud., B. pentandra (Bong.) Steud., B. ungulata L. and Schnella outimouta (Aublet) Wund., tribe Cercidae, subtribe Bauhiniinae (Benth.) Walp., were carried out as subsidies to the quality control of their etnodrugs and their derivatives, as well as an additional support to their taxonomy. The morphological and anatomical studies employed traditional techniques of stereo- and light microscopy. All species showed bifoliate leaves, a dorsiventral mesophyll, epidermis with a papillose abaxial surface, anomocytic stomata at the level of the epidermis, and tector trichomes. Schnella outimouta showed leaf characters distinctive from the three species of Bauhinia: indument puberulous on the abaxial surface, leaves hypostomatic, midrib with two collateral bundles, and a cylindrical petiole. The species of Bauhinia have a sericeous-pubescent indument, amphistomatic leaves with boat-shaped glands, midrib with a single bundle, and a canaliculate petiole with lateral projections. Our results provide leaf morphological and anatomical parameters, useful to distinguish the four species studied, which support the quality control of its ethnodrugs.

ABSTRACT Cissampelos pareira L., belonging to Menispermaceae family, has worldwide distribution, occurring in tropical and subtropical regions of the Americas, Africa and Asia. It is the most popular species of Cissampelos, known for its medicinal uses of leaves and roots. The study aims to find distinctive leaf anatomical characters, and also demonstrate the importance of spectral data to identify C. pareira samples, in order to contribute to its taxonomy and quality control of its drugs. Anatomical leaf analyses were performed by optical and scanning electron microscopy. The spectral profile was obtained from methanolic extracts of C. pareira samples from Brazil and Africa, with application of UV–vis spectrophotometry data, which were analyzed by principal component analysis (PCA). Some anatomical characters such as leaf epidermal cells walls, stomata, trichomes, mesophyll, features of midrib and petiole, and the spectral profile within the wavelength ranging between 770 and 240 nm (eight bands) differs between Brazilian and African samples. The results represent an additional support to the taxonomy of C. pareira, and the quality control of their leaf drugs, mainly in relation to misidentified samples.

resumo Sidastrum micranthum (A. St.-Hil.) Fryxell, pertencente à família Malvaceae, é conhecida no Brasil como "malva preta". A espécie é popularmente usada contra bronquite, tosse e asma, mostrando a relevância de conhecer melhor sua composição química. O estudo fitoquímico do extrato hexânico da espécie, utilizando técnicas cromatográficas, conduziu ao isolamento de seis compostos: o triterpeno isoarborinol, mistura de sitosterol e estigmasterol, sitosterol-3-O-β-D-glicopiranosídeo, feofitina a e de 132-hidroxi-(132-S)-feofitina a. A identificação estrutural destes compostos foi realizada com base em métodos espectroscópicos, tais como IV, RMN 1D e 2D (HOMOCOSY, HMQC, HMBC e NOESY). As substâncias isoladas de Sidastrum micranthum foram avaliadas quanto às suas atividades antimicrobianas in vitro, contra vinte cepas fúngicas e bacterianas. A feofitina a mostrou ação antimicrobiana contra todos os microrganismos testados.

abstract Sidastrum micranthum (A. St.-Hil.) Fryxell, a member of the Malvaceae family, is called malva preta in Brazil. As this species is commonly used to treat bronchitis, cough, and asthma, better knowledge of its chemical compounds is important. The phytochemical study of its hexane extract, using chromatographic techniques, led to isolation of six compounds: the triterpene isoarborinol, a mixture of sitosterol and stigmasterol, sitosterol-3-O-β-D-glucopyranoside, pheophytin a, and 132-hydroxy-(132-S)-pheophytin a. Structural identification of these compounds was carried out using spectroscopic methods such as IR and 1D and 2D NMR (HOMOCOSY, HMQC, HMBC, and NOESY). Compounds isolated from S. micranthum were screened for their in vitro antifungal and antibacterial activity against twenty fungal and bacterial standard strains. Pheophytin a exhibited antimicrobial action against all microorganisms tested.

AbstractSidastrum paniculatum (L.) Fryxell, Malvaceae, is popularly known in Brazil as “malva-roxa” or “malvavisco”. The species is found mainly in Northeast region where it is used by locals to treat spider bites and bee stings. Aiming to identify the chemical compounds from S. paniculatum secondary metabolism and to contribute to the chemotaxonomic knowledge of Malvaceae family, a phytochemical study of S. paniculatum was carried out. Besides that, the isolated compounds were evaluated for antileishmanial activity against promastigotes of Leishmania braziliensis. By using chromatographic techniques the study resulted the isolation of eight compounds: 3-oxo-21β-H-hop-22(29)-ene; sebiferic acid; sitosterol 3-O-β-d-glucopyranoside/stigmasterol 3-O-β-d-glucopyranoside; phaeophytin a; 132(S)-hydroxyphaeophytin a; 132(S)-hydroxy-(173)-ethoxyphaeophorbide a and 7,4′-di-O-methylisoescutellarein. The structure of all isolated compounds was elucidated by spectroscopic analysis, including two-dimensional NMR techniques. In addition, the isolated compounds phaeophytin a; 132(S)-hydroxyphaeophytin a; 132(S)-hydroxy-(173)-ethoxyphaeophorbide a and 7,4′-di-O-methylisoescutellarein exhibited antileishmanial activity against promastigotes of L. braziliensis.

The phytochemical investigation of Erythroxylum pulchrum St. Hil. (Erythroxylaceae) led to the isolation of three known flavonoid glycosides quercetin-3-O-α-L-rhaminoside, ombuin-3-ruthinoside and ombuin-3-ruthinoside-5-glucoside. These flavonoids are being described for the first time in this E. pulchrum. The structures of the compounds were determined by analysis of IR, MS and NMR data, as well as by comparison with literature data. The methanolic extract of leaves from E. pulchrum inhibited the growth of the Bacillus subtilis CCT 0516, Escherichia coli ATCC 2536, Pseudomonas aeruginosa ATCC 8027, P. aeruginosa ATCC 25619, Staphylococcus aureus ATCC 6538, S. aureus ATCC 25925, Streptococcus sanguinis ATCC 15300, S. salivarius ATCC 7073, S. mutans ATCC 25175 and Streptococcus ATCC. S. aureus ATCC 25925 was the most sensitive among the other S. sanguinis while S. salivarius proved the most resistant.

Turnera subulata Sm., known as "Chanana" or "flor-do-Guarujá" in Brazilian folklore, is a plant species belonging to the subfamily Turneroideae of family Passifloraceae, which is used for various medicinal purposes in Brazil. The phytochemical study conducted here led to the isolation and identification of ten compounds present in T. subulata: two mixtures of steroids, sitosterol and stigmasterol (nonglycosylated and glycosylated); a mixture of flavonoids, 5,7,4′-trihidroxiflavona-8-C-α-glucopyranoside and 5,7,3′,4′-tetrahidroxiflavona-8-C-α-glucopyranosidel; and four phaeophytins, phaeophytin purpurin-18-phytyl ester, a rare natural product, phaeophytin a , 13²-hydroxy-(13²-S)-phaeophytin a , and phaeophytin b Phaeophytin b exhibited electrochemical activity similar to that of phthalocyanines.

A phytochemical study on the aerial parts of Wissadula periplocifolia using chromatographic techniques has led to the isolation of sitosterol (1a), stigmasterol (1b), sitosterol 3-O-β-D-glucopyranoside (2a), stigmasterol 3-O-β-D-glucopyranoside (2b), phaeophytin A (3), 13²-hydroxy-(13²-S)-phaeophytin A (4), phaeophytin B (5), 17³-ethoxyphaeophorbide (6), 3,4-seco-urs-4(23),20(30)-dien-3-oic acid (7), 3-oxo-21β-H-hop-22(29)-ene (8), dammaradienone (9a), and taraxastenone (9b). The isolated compounds were characterised by spectroscopic analysis. A preliminary assay to evaluate the antibacterial activity of W. periplocifolia extracts and fractions showed that the dichloromethane, ethyl acetate, and n-butanol fractions were active against Enterococcus faecalis.

O estudo fitoquímico das folhas de Maytenus distichophylla Mart. ex Reissek levou ao isolamento de um novo triterpeno 3,16,21-trioxo-6β,12α-dihidroxi-1-en-friedelano, nomeado maytensifolona, juntamente com os triterpenos conhecidos, 3-oxofriedelano, 3,12-dioxofriedelano, 3β-hidroxifriedelano, 3-oxo-29-hidroxifriedelano, 3-oxo-12α-hidroxifriedelano e 3-oxo-30-hidroxifriedelano. A identificação estrutural foi baseada em métodos espectroscópicos e comparação com dados da literatura

Phytochemical study of the leaves of Maytenus distichophylla Mart. ex Reissek led to the isolation of the new triterpene 3,16,21-trioxo-6β,12α-dihydroxy-1-en-friedelane, named maytensifolone, along with the known triterpenes 3-oxofriedelane, 3,12-dioxofriedelane, 3β-hydroxyfriedelane, 3-oxo-29-hydroxyfriedelane, 3-oxo-12α-hydroxyfriedelane and 3-oxo-30-hydroxyfriedelane. Their structural identification was based on spectroscopic methods and comparison with literature data.

Several species of Solanum are used in folk medicine to treat diarrhea. Therefore, the aim of this study was to investigate and compare possible antidiarrheal activity of methanol extracts from roots (Sast-MeOH R) and leaves (Sast-MeOH L) of Solanum asterophorum Mart., Solanaceae, in mice. Sast-MeOH R was shown to significantly and dose-relatedly inhibit the frequency of both solid (ED50 309.6±28.5 mg/kg) and liquid (ED50 152.1±32.5 mg/kg) stools. Conversely, Sast-MeOH L significantly inhibited solid stool frequency only when dosed at 500 and 750 mg/kg (48.7±7.4 and 42.3±9.8%, respectively), but also significantly and dose-relatedly inhibited liquid stools (ED50 268.4±35.2 mg/kg). Thus, Sast-MeOH R was twice as potent as Sast-MeOH L in diarrhea inhibition. Neither extracts (when dosed up to 500 mg/kg) inhibited intestinal transit. However, both extracts significantly and dose-relatedly inhibited intestinal fluids, and Sast-MeOH R (ED50 38.3±10.4 mg/kg) was again twice as potent as Sast-MeOH L (ED50 78.6±6.4 mg/kg). Results suggest that antidiarrheal effects of Sast-MeOH R and Sast-MeOH L involve changes on intestinal secretion. In addition, active metabolites with antidiarrheal activity may be more concentrated in the roots of this species. However further studies are needed to elucidate the action mechanism involved in this activity.

In this work, a morpho-anatomical study of the leaves, stems and roots of Solanum torvum Sw. was performed with the objective of providing a macroscopical and microscopical morphodiagnosis for its characterization. The species is popularly called "jurubeba-branca" in the Northeastern Brazil and is used in folk medicine to treat liver diseases, tuberculosis, and as antianemic. Anatomical studies were done by paradermic sections of the leaf blade (adaxial and abaxial surfaces), and cross sections of leaves (blade and petiole), stems and roots. The sections were clarified and stained with safranin and/ or astrablue, observed and photographed on light microscope. Histochemical tests were carried out in cross sections of leaves, stems and roots and assayed for specific reagents. The leaves are chartaceous, ovate to elliptic, with lobed margins, oblique at the base. The leaf is amphistomatic with anisocytic and anomocytic stomata simultaneously, and the epidermal cells, in face view, have anticlinal walls sinuate on the upper surface and wavy on the lower surface. The mesophyll is dorsiventral; the midrib has a central bicollateral vascular bundle; and the petiole has three or fourone. The stem shows external phloem, xylem, internal phloem and a parenchymatic pith. The root is axial and striate longitudinally and the secondary xylem is a massive cylinder. The macroscopical and microscopical vegetative characters constitute a set of diagnostic parameters to the studied species.

From the aerial parts of Sidastrum micranthum (A. St.-Hil.) Fryxell (Malvaceae) were isolated m-methoxy-p-hydroxy-benzaldehyde, o-hydroxy-benzoic acid, acacetin, quercetin, 7,4′-Di-O-methylisoscutellarein, genkwanin and tiliroside. These compounds were identified by data analyses of spectroscopic methods. Although acacetin and 7,4′-Di-O-methylisoscutellarein did not display relevant antibacterial activity (MIC = 256 µg/mL), they modulated the activity of antibiotics, i.e. in combination with antibiotics at 64 µg/mL (¼ MIC), a two-fold reduction in the MIC was observed for norfloxacin and ethidium bromide; regarding tetracycline and erythromycin a two-fold reduction in the MIC was observed only with 7,4′-Di-O-methylisoscutellarein.