Pharmacological importance of Manilkara zapota and its bioactive constituents / Importancia farmacologica de Manilkara zapota y sus constituyentes bioactivos

Manilkara zapota (Sapotaceae), commonly known as Sapodilla, is widely known for its delicious fruit. Various parts of this plant are also used in folk medicine to treat a number of conditions including fever, pain, diarrhoea, dysentery, haemorrhage and ulcers. Scientific studies have demonstrated analgesic, anti-inflammatory, antioxidant, cytotoxic, antimicrobial, antidiarrheal, anti-hypercholesteremic, antihyperglycemic and hepatoprotective activities in several parts of the plant. Phytochemical studies have revealed the presence of phenolic compounds including protocatechuic acid quercitrin, myricitrin, catechin, gallic acid, vanillic acid, caffeic acid, syringic acid, coumaric acid, ferulic acid, etc. as main constituents of the plant. Several fatty acids, carotenoids, triterpenes, sterols, hydrocarbons and phenylethanoid compounds have also been isolated from M. zapota. The present review is a comprehensive description focused on pharmacological activities and phytochemical constituents of M. zapota.

Manilkara zapota (Sapotaceae), comúnmente conocida como Sapodilla, es ampliamente conocida por su delicioso fruto. Variadas partes de esta planta se usan en medicina popular para tratar una serie de afecciones, como fiebre, dolor, diarrea, disentería, hemorragia y úlceras. Estudios científicos han demostrado actividad analgésica, antiinflamatoria, antioxidante, citotóxica, antimicrobiana, antidiarreica, antihipercolesterolémica, antihiperglucémica y hepatoprotectora en diferentes partes de la planta. Los estudios fitoquímicos han revelado la presencia de compuestos fenólicos que incluyen ácido protocatechúico, quercitrina, miricitrina, catequina, ácido galico, ácido vanílico, ácido cafeico, ácido sirínico, ácido cumárico, ácido fúnico y ácido ferúlico como componentes principales de la planta. Varios ácidos grasos, carotenoides, triterpenos, esteroles, hidrocarburos y compuestos feniletanoides también han sido aislados de M. zapota. La presente revisión es una descripción exhaustiva centrada en las actividades farmacológicas y los constituyentes fitoquímicos de M. zapota.

Antinociceptive and anti-inflammatory activities of a triterpene-rich fraction from Himatanthus drasticus

Himatanthus drasticus (Mart.) Plumel belongs to the Apocynaceae family and the latex from its trunk bark (Hd) is known as "janaguba milk". This latex is widely used in Northeast Brazil, mainly in the Cariri region, for its gastroprotective, anti-inflammatory, and antitumor properties. The objective of this study was to investigate a triterpene-rich fraction (FJNB) from H. drasticus latex on acute models of nociception and inflammation and to clarify its mechanisms of action. Wistar rats or Swiss mice were subjected to the carrageenan-induced paw edema test or the formalin test, respectively, after the acute oral treatment with FJNB. The inflamed paws from the carrageenan-induced paw edema and formalin tests were processed for histological and immunohistochemical assays, respectively. The results were analyzed by ANOVA and considered significant at P<0.05. FJNB (10 mg/kg) decreased the paw edema by 25% at the 3rd h after the carrageenan injection. Indomethacin, used as reference, inhibited the paw edema by 59% at the same time-point. In the formalin test, FJNB inhibited the 1st phase by 27, 49, and 52% and the 2nd phase by 37, 50, and 67%, at the doses of 1, 5, and 10 mg/kg, respectively. In addition, FJNB significantly inhibited the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and the inflammatory cytokine tumor necrosis factor (TNF)-alpha. The histone deacetylase (HDAC) expression and the transcription factor nuclear factor kappa (NF-kB) were also inhibited at the same doses. In conclusion, the FJNB inhibitory actions on iNOS, COX-2, TNF-α, HDAC, and NF-kB could be involved with the drug anti-inflammatory activity.

Terpene Esters from Natural Products: Synthesis and Evaluation of Cytotoxic Activity

ABSTRACT Natural steroids and triterpenes such as b-sitosterol, stigmasterol, lupeol, ursolic and betulinic acids were transformed into its hexanoic and oleic esters, to evaluate the influence of chemical modification towards the cytotoxic activities against tumor cells. The derivatives were evaluated against five tumor cell lines [OVCAR-8 (ovarian carcinoma); SF-295 (glioblastoma); HCT-116 (colon adenocarcinoma); HL-60 (leukemia); and PC-3 (prostate carcinoma)] and the results showed only betulinic acid hexyl ester exhibits cytotoxic potential activity.

Triterpenes and Beta-agarofurane sesquiterpenes from tissue culture ofMaytenus boaria / Triterpenos y Beta-agarofuranos sesquiterpenos desde cultivo de tejidos de Maytenus boaria

Leaf explants of Maytenus boaria were induced towards callus tissue culture with different mixture of cytokinins and auxins. MeOH extract of callus was partitioned with AcOEt and water, and through repeated chromatography procedures were isolated and identified, four triterpenes and three beta-agarofuran sesquiterpenes.

Explantes de hojas de Maytenus boaria fueron inducidos a formar callos mediante diferentes mezclas de citoquininas y auxinas. Un extracto metanólico de los callos fue fraccionado con AcOEt y agua, y mediante repetidas cromatografías fueron aislados e identificados siete compuestos, cuatro triterpenos y 3 sesquiterpenos del tipo agarofurano.

Phytochemical and biological investigations of methanol extract of leaves of ziziphus mauritiana lam / Investigaciones fitoquímicas y biológicas de extractos metanólicos de hojas de ziziphus mauritiana lam

Seven compounds were isolated from the methanol extract of leaves of Ziziphus mauritiana. The structures of the isolated compounds were elucidated as y-fagarine (1), beta-sitosterol (2), stigmasterol (3), alfa-amyrin (4), lupeol (5), beta-amyrin (6) and betulin (7) by extensive spectroscopic studies and by co-TLC with authentic samples. This is the first report of isolation of compounds 1-7 from this plant species. The extractives from leaves were investigated for thrombolytic, membrane stabilizing, antimicrobial, antidiarrheal and analgesic potentials along with sleep inducing property on animal model. The thrombolytic and membrane stabilizing activities were assessed by using human erythrocyte comparing with standard streptokinase and acetylsalicylic acid, respectively. The methanolic extract reduced frequency of diarrheal faeces when compared to the standard loperamide. In castor oil induced diarrhea in mice a dose dependent decrease of gastrointestinal transits were observed. In radiant heat tail-flick method the methanol extract showed moderate antinociceptive activity, compared to standard morphine.

Siete compuestos fueron aislados del extracto metanólico de hojas de Ziziphus mauritiana. Las estructuras de los compuestos aislados fueron identificadas como y-fagarina (1), beta-sitosterol (2), estigmasterol (3), alfa-amirina (4), lupeol (5), beta-amirina (6) y betulina (7 ) por medio de extensivos estudios espectroscópicos y por co-TLC con muestras auténticas. Este es el primer informe de aislamiento de los compuestos 1-7 a partir de esta especie vegetal. Los extractos de las hojas fueron investigados por efectos trombolíticos, estabilizadores de membrana, antimicrobianos, antidiarreicos y potenciales analgésicos junto a la propiedad de inducir sueño en el modelo animal. Las actividades trombolíticos y la estabilización de la membrana se evaluaron mediante el uso de eritrocitos humanos comparando con estreptoquinasa estándar y el ácido acetilsalicílico, respectivamente. El extracto metanólico redujo la frecuencia de las heces diarreicas en comparación con el estándar de loperamida. En la inducción por aceite de ricino de diarrea en ratones, se observó una disminución dosis dependiente de los tránsitos gastrointestinales. En el método del coletazo producido por calor radiante, el extracto metabólico mostró una actividad antinociceptiva moderada, en comparación con la morfina estándar.

An HPLC-UV and HPLC-ESI-MS based method for identification of anti-inflammatory triterpenoids from the extracts of Ugni molinae / Método CLAE-UV y CLAE-IES-MS para la identificación de triterpenoides anti-inflamatorios de los extractos de Ugni molinae

The aim of this study was to establish an analytical method to detect the presence of the responsible triterpenoids of the anti-inflammatory activity of the leaves of Ugni molinae (murtilla). Successive leaves extracts of EtOAc (EAE) and ethanol (TEE) were prepared, obtaining for the first time from TEE a triterpenoid-rich sub-fraction (TF). The topical anti-inflammatory activity of TF was assessed (43.3 percent at 1 mg/ear) by means of the TPA-induced mouse ear oedema model, which was compared to EAE (83.1 +/- 3.2 percent) and TEE (78.3 +/- 11.8 percent) activities, both previously evaluated by us. These extracts were characterized in their triterpenoids by HPLC-UV and HPLC-ESI-MS. We demonstrated that TF has triterpenoids responsible in part of the anti-inflammatory activity, among them, madecassic and maslinic acids. These two compounds have been reported for the first time for this species. ED50 for madecassic and alphitolic acids are also here reported.

El objetivo de este trabajo fue establecer un método analítico para determinar la presencia de los triterpenoides responsables de la actividad anti-inflamatoria de las hojas de Ugni molinae (murtilla). Fueron preparados los extractos seriados de EtOAc (EAE) y etanólico (TEE) desde sus hojas, obteniendo desde el TEE por primera vez una sub-fracción rica en triterpenoides (TF). Se demostró la actividad anti-inflamatoria tópica del TF por el modelo de edema de oreja de ratón inducida por TPA (43,3 por ciento a 1 mg/oreja), la cual fue comparada con las de los EAE (83,1 +/- 3,2 por ciento) y TEE (78,3 +/- 11,8 por ciento) determinadas en nuestros estudios previos. Dichos extractos fueron caracterizados en sus triterpenoides por CLAE-UV y CLAE-IES-MS. Demostramos que el TF contiene triterpenoides responsables en parte de la actividad anti-inflamatoria, entre ellos, los ácidos madecásico y maslínico, reportados por primera vez para esta especie. Se informan además las DE50 para los ácidos madecásico y alfitólico.

Evaluation of antimicrobial activity of extracts of Tibouchina candolleana (melastomataceae), isolated compounds and semi-synthetic derivatives against endodontic bacteria

This work describes the phytochemical study of the extracts from aerial parts of Tibouchina candolleana as well as the evaluation of the antimicrobial activity of extracts, isolated compounds, and semi-synthetic derivatives of ursolic acid against endodontic bacteria. HRGC analysis of the n-hexane extract of T. candolleana allowed identification of b-amyrin, a-amyrin, and b-sitosterol as major constituents. The triterpenes ursolic acid and oleanolic acid were isolated from the methylene chloride extract and identified. In addition, the flavonoids luteolin and genistein were isolated from the ethanol extract and identified. The antimicrobial activity was investigated via determination of the minimum inhibitory concentration (MIC) using the broth microdilution method. Amongst the isolated compounds, ursolic acid was the most effective against the selected endodontic bacteria. As for the semi-synthetic ursolic acid derivatives, only the methyl ester derivative potentiated the activity against Bacteroides fragilis.

Caracterización del triterpeno cicloartanol aislado del extracto de dicloromentano de Pedilanthus tithymaloides / Characterization of cycloartanol triterpene isolated from dichloromethane extract of Pedilanthus tithymaloides

Introduction: Pedilanthus tithymaloides is known as ítamo real and it has been previously reported as an alternative to treatment of oral cavity virus infections. Objective: to explain procedures to characterize one of the major compounds isolated from dichloromethane extracts of Pedilanthus tithymaloides (L.) Poit (leaves). Methods: it was obtained cycloartanol from dichloromethane extract modifying polarity of the solvents with methanol and by increasing polarity to extract, they were used chromatography technique and spectroscopic of nuclear magnetic resonance H+ and 13C to characterize this compounds. Results: phytochemical studies showed quality parameters that were similar to average limits in the use of majority of medicinal plants except total ashes assay (13 percent), qualitative determination assay suggest presence of reducers compounds, quinone, phenols and/or tannins, triterpene and/or steroids. And they were compared spectrum carbon 13 (13C) of the substance obtained from extract of this plant with other reported in literature to cycloartanol and found coincidence in majority of carbons compared. Conclusions: cycloartanol triterpene was one of main compounds of dichloromethane extract of Pedilanthus tithymaloides (L) Poit leaves

Introducción: Pedilanthus tithymaloides es conocido como ítamo real y se han publicado algunas de sus propiedades, entre ellas, el uso en estomatología para el tratamiento de infecciones bucales. Objetivo: explicar los procedimientos empleados para caracterizar uno de los compuestos mayoritarios aislado del extracto de diclorometano a partir de las hojas de Pedilanthus tithymaloides (L.) Poit. Métodos: el cicloartanol se obtuvo mediante la modificación de la polaridad del disolvente orgánico, con el empleo de metanol e incrementándose la polaridad y como consecuencia la aparición de un precipitado. Se utilizó la técnica de cromatografía de placa delgada, la cromatografía de columna, así como espectroscopia de resonancia magnética nuclear protónica y de carbono 13. Resultados: el estudio fitoquímico mostró parámetros de calidad acorde a lo que se sugiere para el uso de plantas medicinales, excepto las cenizas totales que presentaron 13 por ciento; se comparó el espectro de carbono13 practicado al compuesto obtenido con otros reportes en la literatura y se encontró coincidencia con lo que se describe para el triterpeno cicloartanol. Conclusiones: cicloartanol es uno de los compuestos mayoritario presente en el extracto de dicloromentano obtenido a partir de hojas de Pedilanthus tithymaloides

Antitumor properties of ganoderma lucidum polysaccharidesand terpenoids: [review]

Ganoderma lucidum is an edible medicinal mushroom withimmunomodulatory and antitumor properties, which are mainly attributed to polysaccharides and triterpenesthat can be isolated from mycelia, fruiting bodies and spores. G. lucidum has been used in a powdered form, asa medicinal beverage and a nutraceutical food (usually dried). In the present review we report some historicalfacts and the experimental evidence that polysaccharides and triterpenes obtained from this mushroom presentpotential antitumor activity. Direct effects on tumor cells include induction of apoptosis and interference in thecell cycle, whereas indirect effects are based on the modulation of immune response, usually impaired bycancer cells. Data indicate that G. lucidum can be used as a complementary tool for treatment of cancerpatients.

Trypanocidal constituents in plants: 7. Mammea-type coumarins

Calophyllum brasiliense and Mammea americana (Clusiaceae) are two trees from the tropical rain forests of the American continent. A previous screening showed high trypanocidal activity in the extracts of these species. Several mammea-type coumarins, triterpenoids and biflavonoids were isolated from the leaves of C. brasiliense. Mammea A/AA was obtained from the fruit peels of M. americana. These compounds were tested in vitro against epimastigotes and trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas disease. The most potent compounds were mammea A/BA, A/BB, A/AA, A/BD and B/BA, with MC100 values in the range of 15 to 90 g/ml. Coumarins with a cyclized ,-dimethylallyl substituent on C-6, such as mammea B/BA, cyclo F + B/BB cyclo F, and isomammeigin, showed MC100 values > 200 g/ml. Several active coumarins were also tested against normal human lymphocytes in vitro, which showed that mammea A/AA and A/BA were not toxic. Other compounds from C. brasiliense, such as the triterpenoids, friedelin, canophyllol, the biflavonoid amentoflavone, and protocatechuic and shikimic acids, were inactive against the epimastigotes. The isopropylidenedioxy derivative of shikimic acid was inactive, and its structure was confirmed by X-ray diffraction. Our results suggest that mammea-type coumarins could be a valuable source of trypanocidal compounds.

Evaluation of hepatoprotective activity of Clerodendrum serratum L.

The ethanol extract of C. serratum roots and ursolic acid isolated from it were evaluated for hepatoprotective activity against carbon tetrachloride induced toxicity in male Wistar strain rats. The parameters studied were estimation of liver function serum markers such as serum total bilirubin, total protein, alanine transaminase, aspartate transaminase and alkaline phosphatase activities. The ursolic acid showed more significant hepatoprotective activity than crude extract. The histological profile of the liver tissue of the root extract and ursolic acid treated animal showed the presence of normal hepatic cords, absence of necrosis and fatty infiltration as similar to the controls. The results when compared with the standard drug silymarin, revealed that the hepatoprotective activity of the constituent ursolic acid is significant as similar to the standard drug.

Effect of extracts and isolated compounds from Chresta scapigera on viability of Leishmania amazonensis and Trypanosoma cruzi

Fractionation of bioactive crude extracts of Chresta scapigera led to the isolation of four triterpenes and five flavonoids, among them beta-amyrin acetate (1), 11alpha,12alpha-oxidetaraxeryl acetate (2) and lupeol (3), as well as the flavonoids apigenin (6), kaempferol (7), crysoeriol (8) and luteolin (9) were active against Leishmania amazonensis amastigotes-like stages, while only the flavonoids (6), (7) and (9) showed toxicity towards bloods trypomastigote forms of Trypanosoma cruzi.

O fracionamento dos extratos bioativos de Chresta scapigera proporcionou o isolamento de triterpenos e flavonóides, dentre os quais acetato de beta-amirina (1), acetate de 11alfa,12-oxidotaraxeril (2) e lupeol (3), assim como os flavonóides apigenina (6), caenferol (7), crisoeriol (8) e luteolina (9) mostraram-se ativos contra formas amastigotas de Leishmania amazonensis, enquanto, apenas os flavonóides (6), (7) e (9) apresentaram toxicidade contra as formas tripomastigotas de Trypanosoma cruzi.

new triterpenoid from glycyrrhiza glabra L. and antimicrobial activity

A new pentacyclic triterpenoid was isolated from the minor constituents of local liquorice roots. The structure was determined by means of [1]H-H COSY, [13]C APT, HMQC, HMBC experiments and MS spectroscopy. Another triterpenoid was isolated in a very small amount and its structure was assumed from [1]H-NMR and MS only. The antimicrobial activity of the pentacyclic triterpenoids against Staphylococcus aureus; Escherichia coli, and Candida albicans were investigated. Compound 1 had the highest antibacterial activity against Escherichia coli: and Staphylococcus aureus, while compound 2 had the highest antifungal activity against Candida albicans

Effect of lupeol isolated from Crataeva nurvala Buch.-Ham. stem bark extract against free radical induced nephrotoxicity in rats.

Lupeol, isolated from Crataeva nurvala stem bark in doses 40 and 80 mg/kg body weight, po, for 10 days, decreased the concentration of blood urea nitrogen, creatinine and lipid peroxidation and increased glutathione and catalase activities in cisplatin (5 mg/kg body weight, ip) induced nephrotoxicity in rats. The increased glutathione and catalase activities are indicative of antioxidant properties of lupeol.

Anticonvulsant and behavioral actions of triterpene isolated from Rubia cordifolia Linn.

Effect of a triterpene isolated from the acetone soluble part of petroleum ether extract of R. cordifolia was studied on convulsions induced by maximum electro shock (MES), electrical kindling and various chemoconvulsants in rats and mice. The effect of triterpene was also investigated on behavior and gamma-aminobutyric acid (GABA) and serotonin (5-HT) content in mouse brain. Triterpene inhibited seizures induced by MES, electrical kindling, pentylenetetrazol (PTZ), and lithium-pilocarpine. However, seizures induced by strychnine were not inhibited. Triterpene reduced locomotion as well as rearing. Pentobarbitone induced sleep was potentiated and amphetamine induced stereotypy was inhibited. The triterpene was found to possess anxiogenic activity. Brain GABA and 5-HT contents were raised by the compound. The study suggests that the triterpene isolated from R. cordifolia bear a potential for further study.

Constituintes de Sorocea bomplandii Baillon / Constituents from Sorocea bomplandii Baillon

O estudo químico dos extratos das folhas de Sorocea bomplandii Baillon (Moraceae) levou à identificaçäo de triterpenos pentacíclicos, éster de ácido graxo e isoprenóides. Comparaçäo cromatográfica entre os chás de S. bomplandii com o de Maytenus aquifolium - uma Celastracea com comprovada atividade antiúlcera gástrica - mostrou que os dois possuem composiçöes químicas diferentes: o primeiro é baseado em açúcares e o último, em flavonóides glicosilados.

Constituintes químicos de Cambessedesia espora DC - Melastomataceae / Chemical contituents from Cambessedesia espora DC - Melastomataceae

O fracionamento cromatográfico do extrato hexânico das partes aéreas de Cambessedesia espora DC - Melastomataceae levou ao isolamento dos ácidos palmítico, mirístico e esteárico, ß-Silosterol e do triterpeno fern-9(11)-en-3ß-ol. As substâncias foram identificadas por métodos espectroscópicos usuais (RMN, IV, CG/EM).

Quinone-method triterpenes from tissue cultures of catha edulis

Tingenone and 22 beta hydroxytingenone were isolated from the callus of catha edulis. They were identified by physical and spectral means [optical rotation, IR, UV, CIMS, 1H-, 13C-NMR and two-dimensional NMR] in comparison with the reported data. The isolated quinone-methide triterpenes could not be detected in the mother plant grown in the greenhouse or outdoors. The cytotoxicity of 22 beta hydroxytingenone in several cell-line systems is also reported

Evaluation of the purified fraction of Wilbrandia (c. f. ) verticillata for antitumour activity

Cucurbatacins are known to produce cytotoxic and anticancer activities. Two novel norcucurbitacin glucosides (Wvl and Wv2) have recently been isolated from a purified fraction obtained from the rhizome of Wilbrandia verticillata. The present study evaluates the cytotoxic and anti-tumour activities of the norcucurbitacins. We have found a regular cytotoxicity in KB cells (Cy50 = 12µg/ml) as well as a significant inhibition in the Walker 256 carcinosarcoma growth (approximately 75%).