ABSTRACT
Objective: To evaluate the photoprotective, antioxidant, antiglycation, and antiacne activities of crude extract (CESs) and triterpene saponin fraction (TSSs) of Sapindus saponaria. Methods: HPLC-MS purification was performed on a Symmetry TM C18 column. The saponins were identified by a UV detector. Antioxidant activity was evaluated by DPPH and O 2 - radicals scavenging, and FRAP and TBARS assays. Glycation activity was assessed by relative electrophoretic mobility and inhibition of advanced glycation end products (AGEs) formation. Additionally, antiacne activity was determined by inhibition of Cutibacterium acnes, and photoprotective effect was evaluated by Mansur's method. Results: Most of the triterpene saponins detected in the fraction by HPLC-MS analysis were hederagenin as the aglycon. CESs and TSSs presented varying antioxidant activity in DPPH (CESs: 75.69% and TSSs: 83.65%), FRAP (CESs: 425.39 μM TE/g DW and TSSs: 649.36 μM TE/g DW), TBARS (CESs: 42.96% and TSSs: 52.16%) and O 2 - radicals scavenging (CESs: 61.33% and TSSs: 86.69%) tests. CESs and TSSs also exhibited antiglycation activity comparable to bovine serum albumin treated with aminoguanidine. In addition, CESs and TSSs showed inhibition of AGE formation (34.48% and 61.85%, respectively). Antiacne activity against Cutibacterium acnes was observed with a minimum inhibitory concentration equal to minimum bactericidal concentration (CESs: 36.11 μg/mL and TSSs: 18.34 μg/mL). In photoprotective assays, CESs and TSSs showed maximum absorbance of 1.42 to 0.20 and 2.80 to 1.30, respectively, in the wavelength range of 260 to 400 nm. Furthermore, CESs and TSSs showed sun protection factors of 8.89 and 14.89, respectively. Conclusions: Sapindus saponaria fruit extracts show strong antioxidant potential and antiglycation activity against bovine serum albumin glycation and AGE formation. Besides, they presented antibacterial activity against Cutibacterium acnes and photoprotective effect against UV-A and UV-B.
ABSTRACT
The chemical composition of the oil extracted from the seeds of Sapindus saponaria L., (Sapindaceae), was investigated. Cyanolipids constituted 5 percent hexane extract of the seeds, whereas triacylglycerols (TAG) accounted for 90 percent. The oil contains type III cyanolipids (CL) 1-cyano-2-hydroxymethylprop-1-en-3-ol-diesters. Structural investigation of the oil components was accomplished by chemical, chromatographic (TLC, CC, GC-MS), and spectroscopic (IR, NMR) means. GC-MS analysis showed that fatty acids were dominant in the CL components of the oil from S. saponaria L., with cis-11-eicosenoic acid, cis-11-octadecenoic acid and eicosanoic acid as the only esterified fatty acyl chains respectively. This being the first report of this kind of natural products (CL), located in the seeds of this plant.
La composición química del aceite de las semillas de Sapindus saponaria L., (Sapindaceae), fue investigada. Cianolípidos (CL) constituyen el 5 por ciento del extracto hexanico de las semillas, mientras que los triacilgliceroles (TAG) representaron el 90 por ciento. La fracción cianolipídica estaba compuesta por el CL tipo III, el diester de 1-ciano-2-hidroximetilprop-3-en-1-ol. La investigación estructural de los componentes del aceite se logró mediante técnicas cromatografícas, (CCF, CC, GC-MS), y espectroscópicas (IR, RMN). El análisis por GC-MS mostró que los ácidos grasos tales como: ácidos cis-11-eicosenoico, cis-11-octadecanoico y eicosanoico fueron los únicos ácidos grasos esterificados ubicados en el extracto rico en CL tipo III. Siendo este el primer reporte de esta clase de productos naturales (CL) ubicados en las semilla de esta planta.
Subject(s)
Fatty Acids/analysis , Oils , Sapindus/chemistry , Seeds/chemistry , Chromatography, Gas , Lipids/analysis , Seeds , Spectrum Analysis , Sapindaceae/chemistryABSTRACT
INTRODUCCIÓN: la especie Sapindus saponaria L. se encuentra ampliamente distribuida en el continente americano. La abundante presencia de saponinas que la caracteriza, le confiere un elevado valor farmacológico, por lo que determinar la concentración de este metabolito y la presencia de otros en las diferentes partes de la planta, permitirá desarrollar futuras evaluaciones biológicas. OBJETIVOS: determinar cualitativa y cuantitativamente saponinas en los extractos acuosos de las semillas, tallo y frutos de Sapindus saponaria L., así como identificar la presencia de otros metabolitos secundarios de la planta. MÉTODOS: los extractos (infusión y decocción) se prepararon con los frutos, semillas y tallos de la planta. Se utilizó el método de extracción mediante solventes, y se aplicó las técnicas de infusión y decocción. Para identificar la presencia de metabolitos secundarios se realizó el tamizaje fitoquímico a todos los extractos acuosos. Se realizó el ensayo de hemólisis de eritrocitos para determinar las concentraciones de saponinas en los extractos. Los carbohidratos y las proteínas detectadas se cuantificaron por los métodos de Orcinol Sulfúrico y Lowry, al respecto. RESULTADOS: el tamizaje fitoquímico sugirió la presencia de saponinas, taninos, azúcares reductores y flavonoides en los tres extractos. La mayor concentración de saponinas se encontró en el extracto del pericarpio del fruto, seguido por el de las semillas y el del tallo. La concentración de carbohidratos y proteínas fue mayor en el extracto del fruto que en el resto de los extractos evaluados. CONCLUSIONES: los extractos acuosos obtenidos contienen metabolitos secundarios de elevado interés farmacológico. Las saponinas se encuentran a elevadas concentraciones en el fruto, mientras que, carbohidratos y proteínas están presentes a bajas concentraciones en los tres extractos. of secondary metabolites.
INTRODUCTION: the species Sapindus saponaria L. is widely distributed in America. The abundant presence of saponins is characteristic of this specie and it offers a high pharmacological value. Determine the concentration of these metabolites in various plant parts; allow the development of biological assessments. OBJECTIVES: to determine qualitatively and quantitatively the presence of saponins in aqueous extracts of seeds, stems and fruit of Sapindus saponaria L. and identify other metabolites that may be present in the plant. METHODS: the extracts of the plant, with the fruits, seeds and stem was prepare. The extraction by solvent method and the infusion and decoction techniques was used. To identify the presence of secondary metabolites a phytochemical screening was performed on all extracts. Erythrocyte hemolysis assay was used to determine the concentration of saponins in the extracts. The carbohydrates and proteins were quantitatively determinate by Orcinol Sulphuric method and Lowry method respectively. RESULTS: the phytochemical analysis suggested the presence of saponins, tannins, reducing sugars and flavonoids in the three extracts. The extract of the pericarp had higher concentration of saponins, followed by the seeds and stem. The concentration of carbohydrates and protein was higher in fruit extract than in the rest. CONCLUSIONS: the aqueous extracts obtained by conventional methods, contain secondary metabolites of high pharmacological value. The saponins are found in high concentrations in fruit; however, the carbohydrates and proteins are present at low concentrations in the three evaluated extracts.
Subject(s)
Humans , Plants, Medicinal/drug effects , SapindusABSTRACT
Leishmaniasis and trypanosomiasis are parasitic diseases with a high infection rate, being a serious public health issue in the new world. Unfortunately, there are few available commercial drugs, poorly efficient and with increasing parasite resistance. Under these condi- tions, there is a need for new molecules to develop new and better drugs. One approach to carry out this search is using traditional medicine as information source to obtain new molecules or extracts to control these parasite diseases. Sapindus saponaria (Sapindaceae) fruit resin is used in Colombia to treat ulcers caused by Leishmaniasis. In a bioguided study, we have analyzed the in vitro effect of fruit resin, chroma- tographical fractions from fruit resin and also pure compounds against Leishmania species (L. panamensis, L. braziliensis, L. amazonensis and L. donovani) and Trypanosoma cruzi. The in vivo antileishmanial effect was established under the hamster model for cutaneous leish- maniasis by L. panamensis; refined extract of S. saponaria and pure saponins displayed high in vitro and in vivo activity as leishmanicides. In addition, extracts caused low viability on T. cruzi amastigotes. The use of the crude extract can be a good alternative against cutaneous leishmaniasis, due to its activity, reduced hemolytic effect, and easy production procedures.
La Leishmaniasis y la tripanosomiasis son enfermedades parasitarias con una alta incidencia, siendo un serio asunto de salud pública en el nuevo mundo. Desafortunadamente, hay pocas drogas comerciales disponibles, con pobre eficiencia y con una creciente resis- tencia parasitaria. Bajo esas condiciones, se necesitan nuevas moléculas para desarrollar nuevas y mejores drogas. Una aproximación para llevar a cabo esa búsqueda es usar la medicina tradicional como fuente de información para obtener nuevas moléculas o extractos para con- trolar esas enfermedades parasitarias. La resina de Sapindus saponaria (Sapindaceae) se usa en Colombia para tratar úlceras causadas por la Leishmaniasis. En un estudio bioguiado, se analizó el efecto in vitro de varios extractos de la resina, sus fracciones cromatográficas y algu- nos compuestos puros, contra varias especies de Leishmania (L. panamensis, L. braziliensis, L. amazonensis y L. donovani) panamensis y Trypanosoma cruzi. El efecto lesihmanicida in vivo fue establecido usando el modelo en hamster de leishmaniasis cutánea producida por L. panamensis; los extractos refinados de S. saponaria y las saponinas puras mostraron alta actividad in vitro e in vivo como leishmanicidas. Además, los extractos causaron una baja viabilidad en amastigotes de T. cruzi. El uso de extractos refinados en vez de saponinas puras podría ser una buena alternativa contra leishmaniasis cutánea debido a su actividad, poco efecto hemolítico y procedimientos de producción mucho más fáciles.
Subject(s)
Plant Extracts/pharmacology , Leishmania , Sapindus/chemistry , Trypanocidal Agents/pharmacology , Trypanosoma cruzi , ResinsABSTRACT
Introduction: there are natural products from different fruits and plants that are effective as spermicides, but it is important that they should have little or no cytotoxic effect on epithelial cells. Currently available spermicides with nonoxynol-9 cause vaginal irritation and damage to the vaginal mucosa, the uterine epithelium, and the microbial flora of the vagina. Objective: to elucidate the effect on cell viability, cytotoxicity and apoptosis of spermicidal extracts of Ananas comosus (L.) Merr. and Sapindus saponaria L. over HeLa cell line. Methods: both extracts were evaluated on HeLa cell line using the novel ApoTox-Glo™ Triplex Assay to determine whether cell viability, cytotoxicity and apoptosis were affected. Results: it was determined that treatment with Sapindus saponaria and Ananas comosus extracts initially affected cell viability, but the latter tended to be restored. There was a sign of cell apoptosis that also tended to decrease over time. Conclusions: extracts of Sapindus saponaria and Ananas comosus may affect the survival of cells at the beginning, but these can continue replicating over time. There was a sign of cell apoptosis that also tended to decrease over time. Something similar happened to cell cytotoxicity, indicating that although the extracts may affect the survival of cells at the beginning (6 hours of treatment), these can continue dividing over time.
Introducción: diversos compuestos de procedencia natural como frutos y plantas son altamente efectivos como espermicidas, pero es necesario que estos no tengan efecto citotóxico sobre las células epiteliales. Los espermicidas disponibles actualmente sobre la base de nonoxinol-9, causan irritación y daño en la mucosa, el epitelio uterino y la flora microbiana de la vagina. Objetivo: determinar el efecto sobre la viabilidad, citotoxicidad y apoptosis celular de extractos con actividad espermicida de Ananas comosus (L.) Merr. y Sapindus saponaria L. sobre la línea celular HeLa. Métodos: ambos extractos se evaluaron sobre la línea celular HeLa para determinar el efecto en la viabilidad, la citotoxicidad y la apoptosis celular, utilizando el novedoso ensayo triple ApoTox-Glo™. Resultados: inicialmente el tratamiento con los extractos de Sapindus saponaria y Ananas comosus afectaron la viabilidad celular; sin embargo, esta tendió a restablecerse y mantenerse en el tiempo. Asimismo, la señal de apoptosis celular tendió a disminuir a través de los tiempos de tratamiento. Conclusiones: los extractos de Sapindus saponaria y Ananas comosus podrían afectar la viabilidad celular inicialmente; sin embargo, estas continúan incrementándose con el paso del tiempo. Al mismo tiempo la señal de apoptosis celular disminuyó a través del tiempo y algo similar sucedió con la citotoxicidad celular, indicando que con el paso de las horas los extractos pueden afectar la proliferación celular al inicio (6 h de tratamiento), pero continúan proliferando.
ABSTRACT
Introducción: los espermicidas están entre los métodos anticonceptivos que pueden inmovilizar o matar los espermatozoides. Objetivo: evaluar la actividad espermicida y citotóxica de los extractos de Sapindus saponaria L., conocida como jaboncillo, sobre espermatozoides humanos y la línea celular HeLa, respectivamente. Métodos: las muestras de semen donadas por individuos sanos se incubaron con los extractos de Sapindus saponaria L. y sus respectivas fracciones. La movilidad y la viabilidad espermática se evaluó antes y después de cada tratamiento. Adicionalmente, el efecto citotóxico del extracto se valoró sobre la línea celular HeLa mediante el ensayo 3-(4,5 dimetiltiazol-2-il)-5-(3-carboximetoxifenil)-2-(4-sulfofenil)-2H-tetrazolio (MTS). Resultados: el máximo efecto espermicida se observó cuando las muestras de semen se incubaron con la fracción polar del extracto de hojas de Sapindus saponaria L., luego de 5 min de tratamiento (p< 0,05). No se encontró efecto citotóxico en la línea celular HeLa luego de 6 y 12 h de tratamiento con la fracción polar del extracto de hojas. Conclusión: el extracto de Sapindus saponaria L. puede ser una nueva opción como espermicida con menos efectos adversos.
Introduction: spermicides are contraceptive methods aimed at either immobilizing or killing spermatozoa. Objective: evaluate the spermicidal and cytotoxic activity of extracts of Sapindus saponaria L. (jaboncillo) on human spermatozoa and the HeLa cell line, respectively. Methods: semen samples from healthy individuals were incubated with extracts of Sapindus saponaria L. and their fractions. Sperm motility and viability were measured before and after each treatment. Additionally, the cytotoxic effect of the extract on the HeLa cell line was assessed by the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxy methoxy phenyl)-2-(4-sulfophenyl)-2H-tetrazolium MTS assay. Results: maximum spermicidal effect was observed when semen samples were incubated with the polar fraction of Sapindus saponaria L. leaf extract after 5 minutes of treatment (p< 0.05). No cytotoxic effect on the HeLa cell line was found after 6 and 12 hours of treatment with the polar fraction of the leaf extract. Conclusion: the extract of Sapindus saponaria L. may be a new spermicidal option with fewer adverse effects.
ABSTRACT
The effect of aqueous extracts of Talisia esculenta (T.E.) and Sapindus saponaria (S.S.), were evaluated on the development and mortality of 8-14th day-life Spodoptera frugiperda, an important pest of maize. Corn leaves were dipped in the aqueous extracts (1 percent w/v) and offered as food to the caterpillars. The treated corn leaves with the extracts caused larval mortality (26.71 percent/T.E.; 63.3 percent/S.S.) and also showed effect on the larval weight (237.50 mg/T.E.; 86.65 mg/S.S.) when compared with the control (11.3 percent and 293.45 mg), mortality and larval weight, respectively. The electrophoresis with gelatin (0.1 percent) showed two very clear white areas (trypsin activity) in the caterpillars midgut of all the treatments. Only the caterpillar treated with S. saponaria presented significant differences, showing trypsin activity (10.59 percent). Sapindus saponaria appeared better than Talisia esculenta and showed good potential to be used as control agent for S. frugiperda.
Este estudo procurou avaliar o potencial inseticida dos extratos aquosos de sementes de Talisia esculenta (St. Hil.) Radlk (Pitombal) e Sapindus saponaria L. (Saboneteira), ambas da família Sapindaceae, sobre Spodoptera frugiperda (J.E. Smith) (Lepidoptera: Noctuidae), importante praga da lavoura de milho. As folhas de milho foram imersas nos tratamentos com extratos aquosos (1 por cento p/v) e oferecidas como alimento para as lagartas. Os resultados do período larval tais como mortalidade e peso médio foram respectivamente: para S. saponaria 63,15 por cento, 86,65 mg; para T. esculenta 26,71 por cento, 237,50 mg e para o controle 11,3 por cento, 293,45 mg. A eletroforese com gelatina 0,1 por cento mostrou duas regiões brancas muito nítidas (atividade tríptica) no intestino médio das lagartas de todos os tratamentos. Somente as lagartas do tratamento S. saponaria, apresentaram diferenças significativas, com uma atividade tríptica 10,59 por cento menor.
ABSTRACT
Extracts from the dried pericarp of Sapindus saponaria L. (Sapindaceae) fruits were investigated for their antifungal activity against clinical isolates of yeasts Candida albicans and C. non-albicans from vaginal secretions of women with Vulvovaginal Candidiasis. Four clinical isolates of C. albicans, a single clinical isolated of each of the species C. parapsilosis, C. glabrata, C. tropicalis, and the strain of C. albicans ATCC 90028 were used. The hydroalcoholic extract was bioactivity-directed against a clinical isolate of C. parapsilosis, and showed strong activity. The n-BuOH extract and one fraction showed strong activity against all isolates tested. Further column-chromatography on silica gel separation of this fraction afforded two pure triterpene acetylated saponins: 3-O-(4-acetyl-beta-D-xylopyranosyl)-(1->3)-alpha-Lrhamnopyranosyl-(1->2)-alpha-L-arabinopyranosyl-hederagenin (1) and 3-O-(3,4-di-acetyl-beta-D-xylopyranosyl)-(1->3)-alpha-L-rhamnopyranosyl-(1->2)-alpha-L-arabynopyranosyl-hederagenin (2). The structures of the compounds were based on spectral data (¹H and 13C NMR, HSQC, HMBC and MS), and on with literature. The saponins isolated showed strong activity against C. parapsilosis.
Extratos do pericarpo de frutos de Sapindus saponaria L. (Sapindaceae) foram testados para a atividade antifúngica sobre isolados clínicos de leveduras de Candida albicans e C. não-albicans obtidos de secreção vaginal de mulheres com Candidíase Vulvovaginal. Foram avaliados quatro isolados clínicos de C. albicans, um de cada uma das espécies C. glabrata, C. parapsilosis, C. tropicalis e uma cepa referência de C. albicans ATCC 90028. O extrato hidroalcoólico foi biomonitorado contra um isolado clínico de C. parapsilosis, apresentando forte atividade. O extrato butanólico e uma fração apresentaram forte atividade contra todos os isolados testados. Posterior análise desta fração via cromatografia em sílica gel (CHCl3:CH3OH, 1:1, v/v) resultou no isolamento de duas saponinas triterpênicas puras mono e diacetiladas, 3-O-(4-O-acetil-O-beta-D-xilopiranosil)-(1 -> 3)-alfa-L-ramnopiranosil-(1 -> 2)-alfa-L-arabinopiranosil-hederagenina (1) e 3-O-(3,4-di-O-acetil-beta-D-xilopiranosil)-(1 -> 3)-alfa-L-ramnopiranosil-(1 -> 2)-alfa-L-rabinopiranosil-hederagenina (2) respectivamente. A elucidação estrutural das substâncias foi baseada em dados espectrais (RMN de ¹H e de 13C, HSQC, HMBC, ESI/MS) e comparados com dados da literatura. As saponinas triterpênicas isoladas (1) e (2) apresentaram forte atividade contra C. parapsilosis.