Phytochemical analysis of hydroethanolic extract of Turnera diffusa Willd and evaluation of its effects on astrocyte cell death / Análise fitoquímica do extrato hidroetanólico de Turnera diffusa Willd e avaliação de seus efeitos na morte de astrócitos

ABSTRACT Objective To evaluate the phytochemical composition of hydroethanolic extracts from powdered aerial parts of Turnera diffusa Willd (Turneraceae; T. diffusa), as well as its toxicity in astrocytes. Methods Chemical analyses of hydroethanolic extract from powdered aerial parts ofT. diffusa were carried out using HPLC-DAD-ESI-MS/MS.In vitro assays using astrocytes culture were performed to evaluate cell death. Results Flavone-C, O-diglycosides, such as, luteolin-8-C-[6-deoxy-2-O-rhamnosyl]-xylo-hexos-3-uloside, apigenin-8-C-[6-deoxy-2-O-rhamnosyl]-xylo-hexos-3-uloside and apigenin-7-O-6”-p-coumaroylglucoside were the main compounds found in this hydroethanolic extract. Concentration time-effect demonstrated the toxicity of this extract at a concentration of 1,000µg/mL in astrocyte culture, after 6 and 24 hours of incubation. Conclusion In phytochemical analyses, important antioxidants (mainly flavonoids) were observed. T. diffusa extracts presented cytotoxic effect in high concentrations, leading to increased cell death in astrocyte culture.

RESUMO Objetivo Avaliar a composição fitoquímica do extrato hidroetanólico das partes aéreas de Turnera diffusa Willd (Turneraceae; T. diffusa) e sua toxicidade em astrócitos. Métodos Análises químicas do extrato hidroetanólico de partes aéreas de T. diffusa foram feitas por HPLC-DAD-ESI-MS/MS. Os ensaiosin vitro utilizaram culturas de astrócitos para avaliar morte celular. Resultados Flavonas-C, O-diglicosídeos, como, luteolina-8-C-[6-deoxi-2-O-raminosil]-xilo-hexos-3-ulosideo, apigenina-8-C-[6-deoxi-2-O-raminosil]-xilo-hexos-3-ulosideo e apigenina-7-O-6”-p-cumaroilglucosídeo foram os principais constituintes encontrados neste extrato hidroetanólico. Uma curva tempo-concentração demonstrou toxicidade desse extrato na concentração de 1.000µg/mL, na cultura de astrócitos após 6 e 24 horas de incubação. Conclusão Nas análises fitoquímicas, importantes antioxidantes, sobretudo flavonoides, foram observados. Extratos de T. diffusa apresentaram efeitos citotóxicos em altas concentrações, ocasionando aumento de morte celular em cultura de astrócitos.

Saponins, tannins and flavonols found in hydroethanolic extract from Periandra dulcis roots

Periandra dulcis Mart. ex Benth. Fabaceae (Syn.: P. mediterranea (Vell.) Taub.) is native to the northern and middle parts of Brazil. In Brazilian ethnomedicine, their roots are used as anti inflammatory, expectorant, diuretic and laxative. An HPLC-ESI-MS/MS system was employed to provide a rapid method to make a tentative characterization of the compounds found in the hydroethanolic extract from P. dulcis roots. The structures of sixteen compounds found in this hydroethanolic extract were suggested mainly by MS data conjugated with the UVDAD spectra, reference compounds and available mass spectra data in literature. Saponin derivatives of hederagenin and soyasapogenol E, such as hederagenin-3-O-rhamnosyl glucosyl glucuronide, soyasapogenol E-3-O-rhamnosyl glucosyl glucuronide and periandrin isomers were found as the main constituents, with a minor content of flavonols quercetin and myricetin glycosides derivatives and hydrolysable tannins, such as dihexahydroxydiphenoyl galloyl glucoside and trisgalloyl hexahydroxydiphenoyl glucose.To the best of our knowledge, with exception of periandrins found in the roots, nothing has been published about the chemical composition of P. dulcis..

Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

The diversified genus Passiflora is well distributed all over Brazil, and many species have been long used as medicinal plants, mainly against anxiety disturbances. This effect has been attributed to its rich flavonoid composition. Flavonoids’ main class, flavonoid glycosides, has presented central action, particularly as sedative-hypnotic, anxiolytic and analgesic. The objective of the present study was to make a phytochemical screening of five little studied Passiflora species, in order to evaluate their phenolic composition. For this aim, HPLC-DAD-ESI-MS/MS was used. After the preparation of the hydroalcoholic extracts, each species was evaluated by direct injection electrospray ionization (ESI) and tandem mass spectrometry. Although belonging to the same genus, the composition of each species presented particularities; this justifies the importance of studies aiming for the phenolic composition of different Passiflora species. Flavones C-glycosides were detected in all extracts, and are found as the main constituents in P. vitifolia, P. coccinea, P. bahiensis and P. sidifolia. In this last one, flavone-6,8-di-C-glycoside, apigenin-6-C-rhamnosyl-8-C-arabinoside are present in high content. Cyclopassiflosides were found in high content together with cyanogenic glycosides in P. quadrangularis, while in P. coccinea, besides flavones-C-glycosides were also found procyanidins.

Chemical composition of hydroethanolic extracts from Siparuna guianensis, medicinal plant used as anxiolytics in Amazon region

Siparuna guianensis Aubl., Siparunaceae, is used as anxiolytic plants in folk medicine by South-American indians, "caboclos" and river-dwellers. This work focused the evaluation of phenolic composition of hydroethanolic extract of S. guianensis through HPLC-DAD-ESI/MS/MS. The constituents exhibited protonated, deprotonated and sodiated molecules and the MS/MS fragmentation of protonated, deprotonated and sodiated molecules provided product ions with rich structural information. Vicenin-2 (apigenin-6,8-di-C-glucoside) was the main constituent found in S. guianensis together quercetin-3,7-di-O-rhamnoside and kaempferol-3,7di-O-rhamnoside. A commercial extract of Passiflora incarnata (Phytomedicine) was used as surrogate standard and also was analyzed through HPLC-DAD-ESI/ MS/MS, showing flavones C-glycosides as constituents, among them, vicenin-2 and vitexin. The main constituent was vitexin. Flavonols triglycosides was also found in low content in S. guianensis and were tentatively characterized as quercetin-3O-rutinoside-7-O-rhamnoside, quercetin-3-O-pentosyl-pentoside-7-O-rhamnoside and kaempferol-3-O-pentosyl-pentoside-7-O-rhamnoside. Apigenin and kaempferol derivatives had been reported as anxiolytic agents. Flavonoids present in this extract were correlated with flavonoids reported as anxiolytics.

Constituents and antiproliferative activity of extracts from leaves of Croton macrobothrys

Croton macrobothrys Baill, Euphorbiaceae, is a tree from the Atlantic Forest in Southern Brazil, used in traditional medicine and popularly known as "dragon's blood" and "pau-sangue". Leaf n-hexane, dichloromethane and methanol extracts were analyzed by GC/MS and evaluated for their in vitro antiproliferative activity on cell lines 786-0 (kidney), HT-29 (colon), K562 (leukemia), NCI-ADR/RES (drug resistant ovary), NCI-H460 (lung), MCF-7 (mammary), PC-3 (prostate), OVCAR-3 (ovary), U251 (glioma) and UACC-62 (melanoma). The dicloromethane extract exhibited activity against all cell lines at the concentration 25 µg/mL, in particular on cell lines NCI-H460 (GI50 0.33 μg/mL) and K5662 (GI50 0.91 μg/mL). Relevant constituents in dichloromethane extract are the alkaloids corydine and salutaridine, as well as the diterpenes geranylgeraniol and crotonin-derived clerodanes.

Plants from Solanaceae family with possible anxiolytic effect reported on 19th century's Brazilian medical journal

In the beginning of the 19th century, the first Brazilian scientific knowledge journal on medicinal plants the Gazetas Médicas was launch reporting Brazilian medicinal plants belonging to several botanical families. The aim of this study was research the Solanaceae species that were described as anxiolytics in the 19th century's Brazilian Medical Gazettes and to make a revision about these species in literature. A taxonomic update, together a careful research about ethnopharmacological, pharmacological and phytochemical, patent process and reports of phytomedicines, was carried out for these Solanaceae species. In this research were found thirteen plants, but the taxonomic update reduced this number to six species. Among them, Physalis angulata L. and Solanum nigrum L. were studied and showed depressor activity on central nervous system (CNS) as described in Gazetas Médicas. This research showed that Solanaceae species reported in this study has potential as anxiolytic drugs and should be investigated more deeply.

Bitter acids from hydroethanolic extracts of Humulus lupulus L., Cannabaceae, used as anxiolytic

Humulus lupulus L., Cannabaceae, é usada como sedativo e ansiolítico na medicina popular. O método de HPLC-DAD-ESI-MSn representa uma ferramenta poderosa para a análise de produtos naturais, desde que ela fornece o espectro de UV e informações estruturais sobre os constituintes da mistura. O objetivo deste trabalho foi o de caracterizar os constituintes encontrados no extrato hidroalcoólico. Os constituintes 1-9 foram tentativamente caracterizados através do UV/DAD e ionização por electrospray (MS/MS) depois da separação usando fase reversa, tempo de retenção e dados da literatura. Os principais compostos fenólicos (baseados na área dos picos) foram caracterizados como ácido hulupínico (9), coulupona (8), dois alfa-ácidos amargos oxidados (principais constituintes), um deles sendo um derivado da coumulinona oxidada (5) e o outro um derivado da humulinona oxidada (7), junto com uma procianidina B (3) e os flavonoides rutina (4) e o canferol-7-O-rutinosídeo (6). Esta planta conhecida devido às suas propriedades ansiolíticas e por ser um componente da cerveja, mostrou derivados oxidados de alfa-ácidos, como principais constituintes do extrato hidroalcoólico.

Humulus lupulus L., Cannabaceae, is commonly used as light sedative and anxiolytics in folk medicine. HPLC-DAD-ESI-MSn represents a powerful tool for the analysis of natural products, since it can simultaneously provide a UV chromatogram and significant structural information about compounds in complex mixture. The aim of this work was characterize the constituents present in hydroethanolic extract. Compounds 1-9 were tentatively characterized on the basis of UV, MS/MS, after reversed phase separation, retention time and literature data. The main phenolic compounds (based on peak area) were characterized as hulupinic acid (9), cohulupone (8), two oxidized hop alfa-bitter acids (principal constituents), one being a oxidized cohumulinone (5) and the other an oxidized humulinone (7) derivatives, together with a procyanidin dimer B (3), flavonoids rutin (4) and kaempferol-7-O-rutinoside (6). This plant known, due to anxiolytic property and beer flavoring, showed oxidized hop bitter acids, as principal constituents, in its hydroethanolic extract.

Variação dos teores de constituintes voláteis de Cymbopogon citratus (DC) Staf, Poaceae, coletados em diferentes regiões do Estado de São Paulo / Variation in the amounts of volatile constituents of Cymbopogon citratus (DC) Staf, Poaceae, collected in different regions of São Paulo State

O óleo essencial extraído de Cymbopogon citratus (DC) Staf, Poaceae, é rico em citral sendo amplamente empregado na indústria química e farmacêutica. Os objetivos desse estudo foram avaliar o conteúdo de citral entre populações de C. citratus coletados em duas regiões diferentes (Ibiúna e Pindamonhangaba, Estado de São Paulo). O óleo essencial extraído de uma população cultivada em Pindamonhangaba-SP apresentou uma concentração alta de citral (aproximadamente 96,0 por cento), enquanto que o óleo extraído da população de Ibiúna-SP apresentou, além de citral, proporções elevadas de outro monoterpeno, o geraniol. Adicionalmente, os óleos essenciais obtidos desta população de C. citratus foram extraídos e analisados ao longo de 24 h (a cada 3 h), sendo que o teor de citral foi maior no período da noite, o que mostra a importância de estudos que avaliam as diferenças químicas associadas às mudanças circadianas. Os componentes dos óleos essenciais foram identificados por RMN de 13C, CG/EM e CG através do índice de Kovats.

The essential oil extracted from Cymbopogon citratus (DC) Staf, Poaceae, is rich in citral and has many applications in chemical and pharmaceutical industry. The aims of this study were evaluate the amount of citral in populations of C. citratus collected in two different regions (Ibiúna and Pindamonhangaba, São Paulo State). The essential oil extracted of a cultivated population in Pidamonhangaba-SP, showed a high content of citral (approximately 96.0 percent), while the essential oil from Ibiuna-SP, showed citral and high amounts of another monoterpene, geraniol. Additionally, the essential oils from this population of C. citratus were extracted and analyzed during 24 h (each 3 h), being the major concentration of citral in the night period, indicating that studies which evaluated the chemical differences associated to circadian changes. The components of essential oils were identified through 13C NMR, GC/MS, GC and Kovat's index.

Essential oils found in the smoke of "tira-capeta", a cigarette used by some quilombolas living in pantanal wetlands of Brazil / Óleos essenciais encontrados na fumaça do "tira-capeta", um cigarro utilizado pelos quilombolas que vivem no pantanal do Brasil

An ethnopharmacological survey developed among quilombolas living in Sesmaria Mata-Cavalos, in the State of Mato Grosso, Brazil; a cigarette known as "tira-capeta" (removing-the-devil), had been cited mainly "to improve memory and cognition", and also showed other therapeutical indications, such as: "against sinusitis", "to avoid cold", "to relieve sleep problems". The purpose of the present study was carried out a screening of essential oils delivered in the heating of plants used to produce the "tira-capeta" cigarette, using a simple, rapid and solvent-free method based on gas chromatography-mass spectrometry and headspace solid-phase microextraction. The principal essential oils found were 1,8 cineole, camphor and α-pinene. In the tentative to correlate these constituents with therapeutical indications reported by the quilombolas, were found some works carried out by many authors that corroborated the therapeutical indications reported by the quilombolas.

Pesquisa etnofarmacológica realizada entre os quilombolas que vivem na Sesmaria Mata-Cavalos, no Estado de Mato Grosso, Brasil, um cigarro conhecido como "tira-capeta", foi citado por melhorar a memória e cognição, além de possuir outras indicações terapêuticas, tais como, "contra a sinusite", "para evitar resfriado", e "para aliviar problemas de insônia". No presente estudo, foi feita a caracterização dos óleos essenciais liberados durante o aquecimento das plantas utilizadas na confecção do cigarro, usando um método simples, rápido e livre de solvente baseado em cromatografia gasosa acoplada a espectrometria de massas usando "headspace" e microextração em fase sólida. Os principais constituintes encontrados foram 1,8-cineol, cânfora e α-pineno. Na tentativa de correlacionar a atividade biológica desses constituintes com as indicações terapêuticas relatadas pelos quilombolas, encontramos vários trabalhos realizados por diversos autores que mostraram que estes óleos possuem atividades similares às indicações terapêuticas relatadas pelos quilombolas.

Diabetes melito: plantas e princípios ativos naturais hipoglicemiantes / Diabetes mellitus: hypoglicemic plants and natural active principles

O diabetes melito é considerada como uma síndrome que é, quanto a etiologia e patogênese, caracterizada por alterar a homeostase do organismo, por distúrbios metabólicos complexos e primários dos carboidratos, que envolvem secundariamente, porém de forma importante, lipídeos e proteínas. Grande número de espécies de plantas tem sido usado experimentalmente para tratar os sintomas do diabetes melito e a distância filogenética entre este grupo de plantas é forte indicação da natureza variada de seus constituintes. Tem sido constatado que muitas substâncias extraídas de plantas reduzem o nível de glicose no sangue. A grande diversidade de classes químicas indica que uma variedade de mecanismos de ação deve estar envolvida na redução do nível de glicose no sangue. Algumas dessas substâncias podem ter potencial terapêutico enquanto outras podem produzir hipoglicemia como um efeito colateral devido à sua toxicidade, especialmente hepatoxidade...