Phytochemical investigation of plant from Rutaceae and Meliaceae families aiming for the isolation of target substances to the developing of new antichagastic and antileishmaniasis drugs.

This work involved the bioassay-guided study of Almeidea coerulea, A. rubra, Conchocarpus heterophyllus, Galipea carinata (Rutaceae), and Trichilia ramalhoi (Meliaceae). The bioassays were carried out with T. cruzi GAPDH and L. tarentolae APRT enzymes, and trypomastigote forms of T. cruzi as model assays. The results obtained with extracts and fractions showed that selected plants are promising source for the search of antiprotozoal compounds. Chemical investigation of active fractions (or extracts) allowed the isolation of 30 substances. Among them, 6 are described for the first time: an eudesmane sesquiterpene, pyranoflavones, a tetrahydrofuroquinoline alkaloid, an indolopyridoquinazoline alkaloid, an anthranilic acid derivative, and 1,5-diphenyl-1-pentanone; and 24 substances have already been described in the literature: β-sitosterol and stigmasterol, sitostenone, β-sitosteryl benzoate, lupeol, lupenone, flavone, 7-methoxyflavone, 5-hydroxyflavone, dictamine, kokusagine, skimmianine, δ-fagarine, isokokusagine, isoskimmianine, isodutaduprine, haplotusine, 1-methyl-2-phenyl-4-quinolone, arborinine, scoparone, scopoletin, marmesine, paprazine, N-transferuloyltyramine, and siringic acid. Among these substances, furoquinolone alkaloids isokokusagine and isoskimmianine were actives on the inhibition of APRT enzyme; marmesine was active on GAPDH enzyme; and haplotusine and the 1-methyl-2-phenyl-4-quinolone alkaloid showed significant trypanocidal activities. The biological results showed that a systematic investigation of active chemical classes is needed for determination of structure-activity relationship and obtaining more active substances, that could be used as targets for the development of new antichagasic and antileishmaniasis drugs.Universidade Federal de Minas GeraisEsse trabalho envolveu o estudo fitoquímico de Almeidea coerulea, A. rubra, Conchocarpus heterophyllus, Galipea carinata (Rutaceae) e Trichilia ramalhoi (Meliaceae), biomonitorado através de três modelos biológicos: enzimas GAPDH de T. cruzi e APRT de L. tarentolae; e ensaios in vitro nas formas tripomastigotas de T. cruzi. Os testes biológicos de extratos e frações mostraram que as plantas selecionadas são promissoras na procura de compostos antiparasitários. O estudo químico das frações (ou extratos) ativas permitiu o isolamento de 30 substâncias, sendo 6 inéditas: sesquiterpeno eudesmano, piranoflavonas, alcalóide tetraidrofuroquinolínico, alcalóide indolopiridoquinazolínico, derivado do ácido antranílico e 1,5-difenil-1-pentanona; e 24 já descritas na literatura: β- sitosterol e estigmasterol, sitostenona, benzoato de β-sitosterila, lupeol, lupenona, flavona, 7-etoxiflavona, 5-hidroxiflavona, dictamina, kokusagina, esquimianina, δ-fagarina, isokokusagina, isoesquimianina, isodutaduprina, haplotusina, alcalóide 2-fenil-1-metil-4-quinolona, arborinina, escoparona, escopoletina, marmesina, paprazina, N-trans-feruloitiramina e ácido siríngico. Dentre essas substâncias, os alcalóides furoquinolônicos isokokusagina e isoesquimianina mostraram ser inibidores potentes da enzima APRT; a cumarina marmesina ocasionou uma inibição considerável da atividade da enzima GAPDH; e os alcalóides haplotusina e 2-fenil-1-metil-4-quinolona, e o triterpeno lupeol apresentaram atividades tripanocidas significativas. Os resultados biológicos indicaram a necessidade de um estudo sistemático posterior das classes dos compostos ativos, para a determinação da relação estrutura-atividade e, desta forma, de substâncias mais ativas, que possam ser utilizadas como protótipos no desenvolvimento de novos quimioprofiláticos e/ou quimioterápicos para a doença de Chagas e leishmanioses

Corrosão metálica associada ao uso de combustíveis minerais e biocombustíveis

Fuels and biofuels have a major importance in the transportation sector of any country, contributing to their economic development. The utilization of these fuels implies their closer contact to metallic materials, which comprise vehicle, storage, and transportation systems. Thus, metallic corrosion could be related to fuels and biofuels utilization. Specially, the corrosion associated to gasoline, ethanol, diesel, biodiesel, and their mixtures is discussed in this article. Briefly, the ethanol is the most corrosive and gasoline the least. Few investigations about the effect of biodiesel indicate that the corrosion is associated to their unsaturation degree and the corrosion of diesel is related to its acidity

A new approach for identifying antagonism among fungi species and antifungal activity

New antifungals are increasingly needed due to the emergence of resistant fungal strains. Traditional antifungal assays are laborious and require significant amounts of samples. The present work presents a new proposal to evaluate antifungal activity and antagonism among fungal species, based on experiments of fungal culture and co-culture, 1H NMR profile of fungal culture extracts and chemometrics. In order to develop the work, six axenic cultures of fungi that infested fruits (Fusarium guttiforme, Pestalotiopsis diospyri, Phoma caricae-papayae, Colletotrichum horii, Phytophthora palmivora, and C. gloeosporioides), and co-cultures of all possible combination among them were performed (totalizing 63 experiments). All fungal extracts were evaluated by 1H NMR followed by Principal Component Analyses (PCA) in order to determine spectral dissimilarity among the extracts. Results showed that 1H NMR data evaluated by PCA were capable to predict both antagonism and antifungal activity. Traditional antifungal in vitro assays of active and inactive extracts were also performed in order to prove the prediction made by PCA. The obtained data showed that the approach is an outstanding tool to simultaneously obtain and evaluate bioactive compounds because: it was able to predict the activity of five different extracts in a collection of sixty-three, which would be much more difficult and time consuming if applied randomly; most important antifungal extracts are indicated by PCA; hundreds of traditional in vitro assays are avoid; and, the method is very time and money saving

Trypanocidal activity of Meliaceae and Rutaceae plant extracts

The in vitro trypanocidal activity of 22 extracts and 43 fractions of plants belonging to the families Meliaceae and Rutaceae was evaluated. The extracts from leaves of Conchocarphus heterophyllus and branches of Trichilia ramalhoi were the most active. The trypanocidal activity seems to be increased by fractionation of the extracts. Fractions from C. heterophyllus and Galipea carinata were the most active and a 100% lysis of the parasites was observed for five fractions. From one of them were isolated two flavonoids: flavone and 7-methoxyflavone, which showed weak trypanocidal activity. The results obtained from the extracts and fractions revealed that the order Rutales is a promising source for the search of new drugs for Chagas disease. Phytochemical studies with the other active fractions are underway in order to isolate compounds, which could be associated with observed activities

New pyranoflavones and trypanocidal activity of compounds isolated from Conchocarpus heterophyllus

The phytochemical investigation of trypanocidal extracts from leaves and stems of Conchocarpus heterophyllus (A. St.-Hil.) Kallunki & Pirani (Rutaceae) afforded new pyranoflavones along with the known compounds flavone, 7-methoxyflavone, 5-hydroxyflavone, haplotusine, 1-methyl-2-phenyl-4-quinolone alkaloid, beta-sitosterol, stigmasterol, and beta-sitosteryl benzoate. Their structures were established based on their spectral data. NMR data for the alkaloid haplotusine and the new pyranoflavones are described for the first time herein. These compounds were assayed on the tripomastigote forms of Trypanosoma cruzi. Among them, haplotusine and 1-methyl-2-phenyl-4-quinolone showed moderate values of IC50 136.9 and 144.9 mM, respectively

Trypanocidal Activity of Limonoids and Triterpenes from Cedrela fissilis

Chagas` disease is an illness that affects millions of people in Central and South America, The search for both a prophylactic drug to be added to human blood as well as a safe and reliable therapeutic drug are greatly needed to control such disease. Herein, we report the trypanocidal activity of 15 crude extracts and 14 Compounds (limonoids and triterpenes) as well as the isolation of 25 known compounds (6 limonoids, 12 triterpenes, 1 sesquiterpene, 5 steroids, and 1 flavonoid) from Cedrela fissilis. The present study shows that this plant is a Promising Source of active compounds for the control of Chagas` disease. The inhibitory activity found for odoratol indicates that it is potentially useful as an alternative for the chemoprophylactic gentian violet.Fundacao de Amparo A Pesquisa do Estado de Sao Paulo (FAPESP)Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)Coordenacao de Aperfeicoamento de Pessoal de Ensino Superior (CAPES)Financiadora de Estudos e Projetos (FINEP

Liquid Fungal Cocultivation as a Strategy to Access Bioactive Metabolites

Fungi are a rich source of bioactive compounds. Fungal cocultivation is a method of potentiating chemical interactions and, consequently, increasing bioactive molecule production. In this study, we evaluated the bactericidal, antiprotozoal, and cathepsin V inhibition activities of extracts from axenic cultures of 6 fungi (Fusarium guttiforme, Pestalotiopsis diospyri, Phoma caricae-papayae, Colletotrichum horii, Phytophthora palmivora, and C. gloeosporioides) that infest tropical fruits and 57 extracts obtained by their cocultivation. Our results reveal that fungal cocultivation enhances the biological activity of the samples, since all extracts that were active on Gram-positive bacteria, Gram-negative bacteria, Trypanosoma cruzi, and Leishmania infantum were obtained from cocultivation. Bacterial growth is either totally or partially inhibited by 46% of the extracts. Two extracts containing mainly fusaric and 9,10-dehydrofusaric acids were particularly active. The presence of the fungus F. guttiforme in co-cultures that give rise to extracts with the highest activities against L. infantum. An axenic culture gave rise to the most active extract for the inhibition of cathepsin V; however, other coculture extracts also exhibited activity toward this biological target. Therefore, the results of the biological activities indicate that fungal cocultivation increased the biological potential of samples, likely due to the hostile and competitive environment that pushes microorganisms to produce substances important for defense and allows access to metabolic routes then silenced in milder cultivation conditions