Compounds Friedelin Research Articles

Chemical Constituents from Stem Bark of Flacourtia rukam Zoll. & Mor. and Their Antioxidant Activities

Exploration of chemical compounds and biological activities of extract stem bark of Flacourtia rukam have been succesfully. We have isolated and characterized three compounds friedelin (1), poliothrysoside (2), and β-sitosteryl-3β-glucopyranoside (3). The structures were identified used UV, IR and NMR spectrum data and comparison of their NMR data with literature. The antioxidant activities of each of them were tested used DPPH (1,1-diphenyl-2-picryl hydrazyl) method. All compounds givn IC50 value >100 μg/mL and were categorized weaker antioxidant. Compounds 2 and 3 have been reported from other species from genus Flacourtia but this is the first report of the isolation from F. rukam.

Effect of the metanolic extract from the leaves of Garcinia humilis Vahl (Clusiaceae) on acute inflammation.

Garcinia humilis is popularly used to treat digestive, intestinal and inflammatory illness. We investigated the in vivo and in vitro effects of the methanol extract of G. humilis leaves (MEGh) on inflammatory cells behavior (migration and chemical mediators release) and hypersensitivity. Anti-inflammatory activity was investigated using carrageenan-induced inflammation in the subcutaneous tissue of male Swiss mice treated orally with MEGh (0.1-30mg/kg). Leucocyte migration, chemical mediators secretion (TNF, IL-1β, IL-6 and CXCL1) and protein exudation were quantified in the exudate. The adhesion molecules expression (CD62L and CD18), chemical mediators and chemotaxis was evaluated using neutrophils or macrophages RAW.264.7 previously treated with the extract (1-100µg/mL) and activated with LPS. The anti-inflammatory activity of the isolated compounds friedelin, canophyllol, amentoflavone and 3-desmethyl-2-geranyl-4-prenylbellidypholine xanthone (10μM) was evaluated in macrophages nitric oxide (NO) and TNF release. MEGh, given orally (30mg/kg), significantly reduced neutrophil migration and decreased TNF, IL-1β and CXCL1 levels, without interfering with protein exudation and IL-6. In vitro, the extract significantly reduced IL-1β and IL-6 levels but did not alter TNF and CXCL1. The MEGh also reduced the expression of CD62L and CD18 and consequently neutrophil chemotaxis. The compounds friedelin, amentoflavone and 3-demethyl-2-geranyl-4-prenylbellidypholine xanthone decreased the secretion of NO and TNF by RAW264.7. The MEGh effects were extended to the pain-like behaviour induced by carrageenan in the mice hindpaw. MEGh presented important anti-inflammatory effects probably due to its activity on neutrophil migration and on important chemical mediator release, scientifically reinforcing its use as medicinal plant.

Pharmacognostical, Phytochemical Evaluation and in silico lead finding of Ficus bengalensis Linn with hepatoprotective potentials

Present communication deals with the study of Pharmacognostical, phytochemical screening and antihepatotoxic activity prediction of compounds isolated from Ficus bengalensis Linn in order to search lead compound. Dried leaves and bark powder material was used for determination of ash value, extractive value, and phytochemical constituents. Twelve compounds from the whole plant of Ficus bengalensis were subjected to molecular properties prediction and drug-likeness by Lipinski rule of five & Molinspiration software.Phytochemical screening proved the presence of chemical constituent like tannins, alkaloids, proteins, starch, flavanoids, and glycoside. 9 compounds of the plant fulfill the requirements of Drug likeness were taken for biological activity calculation with the help of Molinspiration software and compared with standard drug Silibinin. On comparision of compounds with silibinin, Friedelin, ? - sitosterol, 3,5,7-trimethyl ether of delphinidin-3-O-?-L rhamnoside, 3,5 dimethyl ether of leucocynaidin-3-O-?-D-glactosylcellobioside and 20-tetratriacontene-2-one fullfill Lipinski rule of five & showed good bioactivity score than Silibinin.Out of 12 compounds Friedelin, ?-sitosterol and 5 dimethyl ether of leucocynaidin-3-O-?-D-glactosylcellobioside showed good bioactivity score as compared to Silibinin. So these compound can be considered as lead compounds with hepatoprotective activity from Ficus bengalensis.

Antimicrobial activity and cytotoxicity of triterpenes isolated from leaves of Maytenus undata (Celastraceae)

BackgroundPlants of the genus Maytenus belong to the family Celastraceae and are widely used in folk medicine as anti-tumour, anti-asthmatic, analgesic, anti-inflammatory, antimicrobial and anti-ulcer agents, and as a treatment for stomach problems. The aim of this study was to isolate and identify active compounds with antifungal activity from Maytenus undata after a preliminary study highlighted promising activity in crude extracts.MethodsSequential extracts of M. undata leaves prepared using hexane, dichloromethane (DCM), acetone and methanol (MeOH) were tested for activity against Cryptococcus neoformans, a fungal organism implicated in opportunistic infections. Bioassay-guided fractionation of the hexane extract using C. neoformans as test organism was carried out to isolate antifungal compounds. The cytotoxicity of compounds isolated in sufficient quantities was evaluated using a tetrazolium-based colorimetric cellular assay (MTT) and a haemagglutination assay (HA).ResultsThe hexane extract was most active with an MIC of 20 μg/ml against C. neoformans. The triterpene compounds friedelin (1), epifriedelanol (2), taraxerol (3), 3-oxo-11α-methoxyolean-12-ene-30-oic acid (4), 3-oxo-11α-hydroxyolean-12-ene-30-oic acid (5) and 3,11-dihydroxyolean-12-ene-30-oic acid (6) were isolated. Compound 6 was isolated for the first time from a plant species. The antimicrobial activity of compounds 1, 3, 5 and 6 was determined against a range of bacteria and fungi implicated in opportunistic and nosocomial infections. Compounds 5 and 6 were the most active against all the tested microorganisms with MIC values ranging between 24 and 63 μg/ml, except against Staphylococcus aureus which was relatively resistant. Compounds 1 and 3 had a low toxicity with an LC50 > 200 μg/ml towards Vero cells in the MTT assay. Compounds 5 and 6 were toxic with LC50 values of 6.03±0.02 and 2.98±0.01 μg/ml, respectively. Compounds 1 and 3 similarly were not toxic to the red blood cells (RBCs) but compounds 5 and 6 were toxic, showing HA titer values of 1.33 and 0.67 respectively.ConclusionsCompounds 5 and 6 were the most active but were also relatively cytotoxic to monkey kidney cells and red blood cells, while the other isolated compounds were less active and less cytotoxic.

New dipyranocoumarin from the leaves of Calophyllum apetalum Willd

A new dipyranocoumarin, α-hydroxytomentolide A (1) was isolated from the leaves of Calophyllum apetalum together with the known compounds friedelin (2), apetalactone (3), inophyllum C (4) and canophyllol (5). The structure of the new compound was established by spectroscopic studies which include 1H NMR, 13C NMR, NOESY, HetCOSY, COLOC experiments and single crystal X-ray diffraction analysis.

New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations

Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β-olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (1H, 13C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane (4) were evaluated by the Ellman’s method and all these compounds showed acethylcholinesterase inhibitory properties.

3-Oxo-11β-Hydroxyfriedelane from the Roots of Celastrus Monospermus

A new friedelane type triterpene, 3-oxo-11β-hydroxyfriedelane, named as monospermol, was isolated from the roots of Celastrus monospermus Roxb.(Celastraceae) along with seven known compounds friedelin, 3,12-dioxofriedelane, 3-oxo-28-hydroxyfriedelane, 3-oxo-12α-hydroxyfriedelane, β-sitosterol, pristimerin and celastrol. Structural formula and the stereochemistry of the new friedelane type triterpene 1 were established through 1H NMR and 13C NMR spectral data including 2D experiments (HMBC, HSQC, 1H-1H COSY and NOESY) and high resolution mass spectrometry.

Endodesmiadiol, a Friedelane Triterpenoid, and Other Antiplasmodial Compounds from Endodesmia calophylloides

From the ethyl acetate extract of the stem bark of Endodesmia calophylloides (Guttiferae), a novel friedelane triterpenoid named endodesmiadiol (1), as well as the known compounds friedelin (2), canophyllol (3), canophyllal (4), cerin (5), morelloflavone (6), volkensiflavone (7), 8-deoxygartanin (8), 3 beta-acetoxyoleanolic acid (9) and 1,8-dihydroxy-3-isoprenyloxy-6-methylxanthone (10) have been isolated. The structures of these compounds were established by spectroscopic analysis, and the relative configuration of endodesmiadiol (1) was confirmed by X-ray diffraction. The antiplasmodial activity of the isolated compounds was evaluated against the W2 strain of Plasmodium falciparum which is resistant to chloroquine and other antimalarial drugs. All the compounds were found to be active with IC50 values ranging from 7.2 to 23.6 microM. The IC50 of endodesmiadiol was found to be 11.8 microM.

Bioactive compounds from Celaenodendron mexicanum.

Bioactivity-directed fractionation of the CHCl3-MeOH extract of the leaves of Celaenodendron mexicanum by means of the brine shrimp lethality test and chromatographic techniques led to the isolation of three carboxylic acid triterpenes, the new tirucalla-type triterpene, 3 alpha-hydroxytirucalla-7,24Z-dien-26-oic acid, 3-oxotirucalla-7,24Z-dien-26-oic acid, and epi-oleanolic acid, and three biflavonoids amentoflavone, podocarpusflavone A, and podocarpusflavone B. Four non-active compounds friedelin, maytensifolin B, 3 beta-hydroxyfriedelan-16-one, and celaenodendrolide were also obtained. epi-Oleanolic acid was the most active against brine shrimps with LC50 value of 23.3 microM. In addition, all isolates were tested for in vitro antiprotozoal and cytotoxic activities. 3-Oxotirucalla-7,24Z-dien-26-oic acid and epi-oleanolic acid showed the highest activity against Leishmania donovani promastigotes with IC50 values of 13.7 and 18.8 microM, respectively. Only 3-oxotirucalla-7,24Z-dien-26-oic acid showed activity against Trypanosoma brucei brucei bloodstream forms with IC50 value of 16.8 microM.

Friedelane triterpenoids from Maytenus macrocarpa.

A set of friedelane triterpenoids has been isolated from the stem bark exudates of Maytenus macrocarpa. It includes a new friedelan triterpene (1), together with the known compounds friedelin, 3-oxo-29-hydroxyfriedelane, 3-oxofriedelan-25-al, and canophyllol. The structures of these compounds were elucidated by spectroscopic and chemical evidence. Complete 1H and 13C assignments were achieved by 2D NMR spectroscopy. The new compound showed weak activity against aldose reductase. It did not display antitumor activity against P-388 lymphoid neoplasm, A-549 human lung carcinoma, HT-29 human colon carcinoma, or MEL-28 human melanoma cell lines.

Effects of some compounds isolated fromCelaenodendron mexicanum standl (euphorbiaceae) on seeds and phytopathogenic fungi

The known compounds friedelin, maytensifolin B, ginkgetin, bilobetin, and amentoflavone as well as the new triterpene 3β-hydroxyfriedelan-16-one were isolated fromCelaenodendron mexicanum (Euphorbiaceae), an endemic tree of the Pacific Ocean coast of Mexico. The compounds' structures were established on the basis of spectral analysis. The biological effects of aqueous leachates, a CHCl3-MeOH extract and the isolated compounds of leaves and twigs were evaluated on the radicle growth of two plants,Amaranthus leucocarpus andEchinochloa crusgalli, and on the radial growth of three phytopathogenic fungi,Fusarium sp.,Helminthosporium sp., andAlternaria sp. The organic extracts of both leaves and twigs inhibitedAmaranthus and stimulatedEchinochloa radicle growth. On the contrary, friedelin and maytensifolin B stimulatedAmaranthus and inhibitedEchinochloa. The target fungi showed a different response to each treatment, from inhibition to stimulation.

A clerodane diterpene and other constituents of Clerodendron inerme

A new clerodane diterpene clerodermic acid was isolated from Clerodendron inerme and the structure deduced from spectral data. The known compounds friedelin, 5-hydroxy-7,4′-dimethoxyflavone, salvigenin, acacetin and apigenin were also found.

Constituents of Bridelia micrantha

The compounds friedelin, taraxerone, epifriedelinol, taraxerol, gallic acid and ellagic acid have been isolated from Bridelia micrantha. The presence of leucodelphinidin and caffeic acid was also indicated.