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At least 217 records · Page 12Linked to original sources
PubMed2000

Saponins from Fagonia glutinosa.

Twelve triterpenoid saponins, including six new, were isolated and identified from the aerial parts of Fagonia glutinosa. The new saponins were characterised as 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-xylopyranosyl(1-->2)][beta- D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid, 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D- glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl ursolic acid 28-O-beta-D-glucopyranosyl ester and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->3)]-alpha-L - arabinopyranosyl-27-hydroxy ursolic acid 28-O-beta-D-glucopyranosyl ester. The structures of the saponins were established by spectral and chemical evidences. The assignments of the NMR signals were performed by means of HOHAHA, 1H-1H COSY, ROE, HMQC and HMBC experiments.

Egypt↗
PubMed2006

Antioxidant, anti-inflammatory and anticancer activities of methanolic extracts from Ledum groenlandicum Retzius.

Labrador tea (Ledum groenlandicum Retzius) is an ericaceae widely distributed in North America. The leaves and twigs were used in Native American traditional medicine to treat several inflammatory pathologies such as asthma, rheumatisms and burns. Reactive oxygen species as well as reactive nitrogen species such as nitric oxide (NO) contribute significantly to these pathologies. In this study, the antioxidant, anti-inflammatory and anticancer activities of crude methanol extracts of leaves and twigs from Ledum groenlandicum were investigated. Both extracts showed a strong antioxidant activity using the ORAC method and a cell based-assay. Moreover, the twig and leaf extracts showed significant anti-inflammatory activity, inhibiting NO release, respectively, by 28 and 17% at 25 microg/ml in LPS-stimulated RAW 264.7 macrophages. In comparison, N(G)-nitro-L-arginine methyl ester (L-NAME), a nitric oxide synthase inhibitor, reduced NO release by 24% at 25 microg/ml. The twig extract was also found to be active against DLD-1 colon carcinoma and A-549 lung carcinoma cells, with IC(50) values of 43+/-1 and 65+/-8 microg/ml, respectively. The bioguided study of the twig extract resulted in the isolation and identification of ursolic acid, a known triterpene. Ursolic acid was active against DLD-1 (IC(50): 9.3+/-0.3 microM) and A-549 (IC(50): 8.9+/-0.2 microM), suggesting it is, in part, responsible of the anticancer activity of the twig extract.

Animals↗
PubMed2000

Cytotoxic triterpenes from Crataegus pinnatifida.

Bioassay-guided fractionation of Crataegus pinnatifida (Rosaceae) gave two cytotoxic ursane-type triterpenes which were identified as uvaol (1) and ursolic acid (2) by physicochemical and spectroscopic methods. 3-Oxo-ursolic acid (3) was synthesized from ursolic acid (2) by Jones method. The cytotoxic activities of these compounds were tested against murine L1210 and human cancer cell lines (A549, SK-OV-3, SK-MEL-2, XF498, and HCT15) in vitro. Compounds 1 and 2 showed moderate cytotoxicities against L1210, whereas they showed weak activities against human cancer cell lines. However, compound 3 exhibited potent cytotoxic activities both in murine and in human cancer cell lines.

Animals↗
PubMed2004

Pentacyclic triterpenoic acids: new chemoprotective compounds. Minireview.

Ursolic acid and oleanolic acid are pentacyclic triterpenoic acids having a similar chemical structure and are the major components of some oriental and traditional medicine herbs wildly distributed all over the world. There is a growing interest in the elucidation of the biological roles of both these triterpenoid compounds. This review summarizes the biological activities of presented triterpenoid acids (anti-inflammatory, hepatoprotective, gastroprotective, anti-ulcer, anti-HIV, cardiovascular, hypolipidemic, antiatherosclerotic and immunoregulatory effects). Our interest has been focussed especially on their anti-tumor and chemopreventive activity. Both compounds have been shown to act at various stages of tumor development, including inhibition of tumorigenesis, inhibition of tumor promotion, and induction of tumor cell differentiation. They effectively inhibit angiogenesis, invasion of tumor cells and metastasis. However, the mechanisms by which they act are poorly understood. Ursolic acid and oleanolic acid are relatively non-toxic and could be use as chemopreventive/chemoprotective agents in clinical praxis.

Animals↗
PubMed2002

Extract and identify ingredient from Ligustrum Lucidum Ait and study its effect to periodontal pathogen.

OBJECTIVE: To extract the effective ingredient (crystal I) from effective section (saponin) of Ligustrum Lucidum Ait, identify the chemical structure of crystal I, study the effect of crystal I on P. gingivalis, B. forsythus and P. intermedia. METHODS: Isolated crystal I from saponin using the silica gel column chromatograph. Identified crystal I with IR spectra, (1)H-NMR and (13)C-NMR. Measured the minimal inhibitory concentration (MIC) and the minimal bactericidal concentration (MBC) through micro-liquid dilution. Studied the killing curve of ursolic acid on B. forsythus and P. intermedia. RESULTS: The crystal I was identified as ursolic acid; its MIC and MBC to P. gingivalis, B. forsythus and P. intermedia were 0.740 and 0.295 microg/L respectively. The killing curve indicated that 0.800 microg/L ursolic acid could kill P. intermedia and B. forsythus in 3 and 6 hours respectively. CONCLUSION: Ursolic acid has obvious effect to inhibit periodontal pathogen.

Bacteroides↗
PubMed2004

Hepatoprotective activity of Terminalia catappa L. leaves and its two triterpenoids.

The aim of this study was to evaluate the effect of the chloroform extract of Terminalia catappa L. leaves (TCCE) on carbon tetrachloride (CCl(4))-induced acute liver damage and D-galactosamine (D-GalN)-induced hepatocyte injury. Moreover, the effects of ursolic acid and asiatic acid, two isolated components of TCCE, on mitochondria and free radicals were investigated to determine the mechanism underlying the action of TCCE on hepatotoxicity. In the acute hepatic damage test, remarkable rises in the activity of serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) (5.7- and 2.0-fold) induced by CCl(4) were reversed and significant morphological changes were lessened with pre-treatment with 50 and 100 mg kg(-1) TCCE. In the hepatocyte injury experiment, the increases in ALT and AST levels (1.9- and 2.1-fold) in the medium of primary cultured hepatocytes induced by D-GalN were blocked by pre-treatment with 0.05, 0.1, 0.5 g L(-1) TCCE. In addition, Ca(2+)-induced mitochondrial swelling was dose-dependently inhibited by 50-500 microM ursolic acid and asiatic acid. Both ursolic acid and asiatic acid, at concentrations ranging from 50 to 500 microM, showed dose-dependent superoxide anion and hydroxyl radical scavenging activity. It can be concluded that TCCE has hepatoprotective activity and the mechanism is related to protection of liver mitochondria and the scavenging action on free radicals.

Animals↗
PubMed1996

Inhibition by rosemary and carnosol of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation.

Extracts of the spice Rosemary officinalis L. have been reported to inhibit experimental carcinogenesis. Two rosemary components, carnosol and ursolic acid, appear to be partly responsible for the antitumorigenic activity of rosemary. The present studies were conducted in order to evaluate the activity of rosemary extract, carnosol and ursolic acid in inhibiting the in vivo formation of mammary 7,12-dimethylbenz[a]anthracene (DMBA)-DNA adducts and the initiation of DMBA-induced mammary tumorigenesis in female rats. Supplementation of diets for 2 weeks with rosemary extract (0.5% by wt) but not carnosol (1.0%) or ursolic acid (0.5%) resulted in a significant decrease in the in vivo formation of rat mammary DMBA-DNA adducts, compared to controls. When injected intraperitoneally (i.p.) for 5 days at 200 mg/kg body wt, rosemary and carnosol, but not ursolic acid, significantly inhibited mammary adduct formation by 44% and 40%, respectively, compared to controls. Injection of this dose of rosemary and carnosol was associated with a significant 74% and 65% decrease, respectively, in the number of DMBA-induced mammary adenocarcinomas per rat, compared to controls. Ursolic acid injection had no effect on mammary tumorigenesis. Therefore, carnosol is one rosemary constituent that can prevent DMBA-induced DNA damage and tumor formation in the rat mammary gland, and, thus, has potential for use as a breast cancer chemopreventative agent.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed2004

Evaluation of apparent formation constants of pentacyclic triterpene acids complexes with derivatized beta- and gamma-cyclodextrins by reversed phase liquid chromatography.

A reversed phase HPLC method has been investigated in order to resolve three main pentacyclic triterpene acids (oleanolic-, betulinic- and ursolic acid) found in a lot of plants. Some of them (oleanolic and ursolic acids) are position isomers and their resolution is highly improved by the addition of derivatized cyclodextrins in mobile phase. The formation of 1:1 inclusion complexes was assumed. Apparent formation constants of triterpene acids with DM-beta-CD and HP-gamma-CD were determined by HPLC method. Experimental results confirmed the complexation model and explained the modification of elution order according to the type of cyclodextrin added to the mobile phase. The influence of mobile phase organic modifier on apparent formation constants was also investigated. Results proved the competition between cyclodextrins hydrophobic cavity and organic solvent towards triterpene acids affinity.

Chromatography, High Pressure Liquid↗
PubMed2005

Antiviral activities of extracts and selected pure constituents of Ocimum basilicum.

1. Ocimum basilicum (OB), also known as sweet basil, is a well known medicinal herb in traditional Chinese medicine preparations. In the present study, extracts and purified components of OB were used to identify possible antiviral activities against DNA viruses (herpes viruses (HSV), adenoviruses (ADV) and hepatitis B virus) and RNA viruses (coxsackievirus B1 (CVB1) and enterovirus 71 (EV71)). 2. The results show that crude aqueous and ethanolic extracts of OB and selected purified components, namely apigenin, linalool and ursolic acid, exhibit a broad spectrum of antiviral activity. Of these compounds, ursolic acid showed the strongest activity against HSV-1 (EC50 = 6.6 mg/L; selectivity index (SI) = 15.2), ADV-8 (EC50 = 4.2 mg/L; SI = 23.8), CVB1 (EC50 = 0.4 mg/L; SI = 251.3) and EV71 (EC50 = 0.5 mg/L; SI = 201), whereas apigenin showed the highest activity against HSV-2 (EC50 = 9.7 mg/L; SI = 6.2), ADV-3 (EC50 = 11.1 mg/L; SI = 5.4), hepatitis B surface antigen (EC50 = 7.1 mg/L; SI = 2.3) and hepatitis B e antigen (EC50 = 12.8 mg/L; SI = 1.3) and linalool showed strongest activity against AVD-II (EC50 = 16.9 mg/L; SI = 10.5). 3. No activity was noted for carvone, cineole, beta-caryophyllene, farnesol, fenchone, geraniol, beta-myrcene and alpha-thujone. 4. The action of ursolic acid against CVB1 and EV71 was found to occur during the infection process and the replication phase. 5. With SI values greater than 200, the potential use of ursolic acid for treating infection with CVB1 and EV71 merits further investigation.

Acyclic Monoterpenes↗
PubMed2004

Novel ceramides and a new glucoceramide from the roots of Incarvillea arguta.

Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxycosanoyl-hexacosanoylamino]-4-hydroxy-5-[(4Z)-tetradecane-4-ene]-2,3,4,5-tetrahydrofuran (1a-g), and a new glucoceramide, 1-O-beta-D-glucopyranosyl-(2S,3S,4R,8E)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octodecanetriol-8-ene (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: beta-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), beta-sitosterol 6'-O-acyl-beta-D-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [1H NMR, 13C NMR (distortionless enhancement by polarization transfer), 1H-1H COSY, heteronuclear multiple-quantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling constants with those already reported in the literature.

Bignoniaceae↗
PubMed2006

Molecular targets of dietary agents for prevention and therapy of cancer.

While fruits and vegetables are recommended for prevention of cancer and other diseases, their active ingredients (at the molecular level) and their mechanisms of action less well understood. Extensive research during the last half century has identified various molecular targets that can potentially be used not only for the prevention of cancer but also for treatment. However, lack of success with targeted monotherapy resulting from bypass mechanisms has forced researchers to employ either combination therapy or agents that interfere with multiple cell-signaling pathways. In this review, we present evidence that numerous agents identified from fruits and vegetables can interfere with several cell-signaling pathways. The agents include curcumin (turmeric), resveratrol (red grapes, peanuts and berries), genistein (soybean), diallyl sulfide (allium), S-allyl cysteine (allium), allicin (garlic), lycopene (tomato), capsaicin (red chilli), diosgenin (fenugreek), 6-gingerol (ginger), ellagic acid (pomegranate), ursolic acid (apple, pears, prunes), silymarin (milk thistle), anethol (anise, camphor, and fennel), catechins (green tea), eugenol (cloves), indole-3-carbinol (cruciferous vegetables), limonene (citrus fruits), beta carotene (carrots), and dietary fiber. For instance, the cell-signaling pathways inhibited by curcumin alone include NF-kappaB, AP-1, STAT3, Akt, Bcl-2, Bcl-X(L), caspases, PARP, IKK, EGFR, HER2, JNK, MAPK, COX2, and 5-LOX. The active principle identified in fruit and vegetables and the molecular targets modulated may be the basis for how these dietary agents not only prevent but also treat cancer and other diseases. This work reaffirms what Hippocrates said 25 centuries ago, let food be thy medicine and medicine be thy food.

Animals↗
PubMed2005

Cytotoxic triterpenes from the aerial roots of Ficus microcarpa.

Six triterpenes, 3beta-acetoxy-12,19-dioxo-13(18)-oleanene (1), 3beta-acetoxy-19(29)-taraxasten-20alpha-ol (2), 3beta-acetoxy-21alpha,22alpha-epoxytaraxastan-20alpha-ol (3), 3,22-dioxo-20-taraxastene (4), 3beta-acetoxy-11alpha,12alpha-epoxy-16-oxo-14-taraxerene (5), 3beta-acetoxy-25-methoxylanosta-8,23-diene (6) along with nine known triterpenes, 3beta-acetoxy-11alpha,12alpha-epoxy-14-taraxerene (7), 3beta-acetoxy-25-hydroxylanosta-8,23-diene (8), oleanonic acid (9), acetylbetulinic acid (10), betulonic acid (11), acetylursolic acid (12), ursonic acid (13), ursolic acid (14), and 3-oxofriedelan-28-oic acid (15) were isolated from the aerial roots of Ficus microcarpa, and their structures elucidated by spectroscopic methods. The in vitro cytotoxic efficacy of these triterpenes was investigated using three human cancer cell lines, namely, HONE-1 nasopharyngeal carcinoma, KB oral epidermoid carcinoma, and HT29 colorectal carcinoma cells. Compound 8 and pentacyclic triterpenes 9-15 possessing a carboxylic acid functionality at C-28 showed significant cytotoxic activities against the aforementioned cell lines and gave IC50 values in the range 4.0-9.4 microM.

Air↗
PubMed2003

Antiplasmodial triterpenes from twigs of Gardenia saxatilis.

Ten triterpenes (1-10) were isolated and identified from the twigs of Gardenia saxatilis (Rubiaceae) and were subjected to antiplasmodial evaluation against the parasite Plasmodium falciparum. The first six compounds, lupenone (1), lupeol (2), betulinic acid (3), oleanolic acid (4), ursolic acid (5), and winchic acid (27-O-feruloyloxybetulinic acid) (6) were inactive in the assay. The other four compounds, messagenic acid A (7) and messagenic acid B (8), the 27-O-p-(Z)- and 27-O-p-(E)-coumarate esters of betulinic acid, and a mixture of uncarinic acid E (27-O-p-(E)-coumaroyloxyoleanolic acid) (9) and 27-O-p-(E)-coumaroyloxyursolic acid (10) exhibited antiplasmodial activity, with the IC50 values of 1.5, 3.8 and 2.9 microg/ml, respectively. The results indicated that the p-coumarate moieties at the 27-position, both the cis and trans isomers, contributed to antiplasmodial activity. Introduction of a methoxyl group to the 3-position of the p-coumarate moiety to give a ferulate moiety resulted in loss of activity.

Animals↗
PubMed2005

Four new prenylated isoflavonoids in Tadehagi triquetrum.

Investigation on the anthelminthic bioactive compounds of the ethanol extract of Tadehagi triquetrum resulted in the isolation of three new prenylated isoflavones, triquetrumones A (1), B (2), and C (3), and one new prenylated biisoflavanone, (R)-triquetrumone D (4), along with 16 known compounds, cyclokievitone (5), yukovanol (6), aromadendrin (7), kaempferol (8), astragalin (9), 2-O-methyl-l-chiro-inositol (10), galactitol (11), p-hydroxycinnamic acid (12), ursolic acid (13), betulinic acid (14), beta-sitosterol (15), daucosterol (16), stigmasterol (17), stigmasta-5,22-dien-3-O-beta-d-glucopyranoside (18), saccharose (19), and docosanoic acid (20). The structures of 1-4 were elucidated on the basis of spectroscopic and spectrometric methods. Compounds 1-3 displayed mild anthelminthic bioactivity, and compound 3 showed a significant binding ability to the estrogen receptor.

Animals↗
PubMed2006

Quantification of the polyphenols and triterpene acids in chinese hawthorn fruit by high-performance liquid chromatography.

The levels of seven polyphenols (epicatechin, procyanidin B2, procyanidin B5, procyanidin C1, hyperoside, isoquercitrin, and chlorogenic acid) and two triterpene acids (oleanolic acid and ursolic acid) in the matured fruits of Chinese hawthorn (Crataegus pinnatifida Bge. var. major N.E.Br.) were determined by high-performance liquid chromatography methods. The average contents of those constituents in 37 representative cultivars were 1405, 1505, 339, 684, 56, 41, 234, 952, and 147 microg/g fresh weight (FW), respectively. A significant inverse correlation between the procyanidin contents and the latitude of the geographical origin of the cultivars was observed (r = 0.3851, P < 0.02). Correlation analysis of the levels of the nine compounds in the 37 cultivars yielded a strong correlation (P < 0.001) between the individual levels of the four procyanidins and the sum of the procyanidins level (r = 0.7413-0.9898) and between the flavonoids and the chlorogenic acid (r = 0.5383-0.9212). The changes in level of the nine compounds in the hawthorn fruit were evaluated during maturation using the Hebei Dajinxing cultivar. Sixty-one days after blossom, the polyphenol level reached the highest point and the sum of the contents was 1.36 g/100 g FW.

Chlorogenic Acid↗
PubMed2000

Identification of three triterpenoids in almond hulls.

Three triterpenoids, betulinic acid, oleanolic acid, and ursolic acid, were isolated as their methyl esters (treatment with diazomethane) from diethyl ether extracts of almond hulls (Nonpareil variety) using flash chromatography and preparative high-performance liquid chromatography. The triterpenoids, which comprised approximately 1% of the hulls, were characterized using chromatographic and spectroscopic methods. These studies demonstrate that almond hulls are a rich source of these triterpenoids, which have reported anti-inflammatory, anti-HIV, and anti-cancer activities.

Chromatography, Gas↗
PubMed2004

Three new oleanane-type triterpenes from Ludwigia octovalvis with cytotoxic activity against two human cancer cell lines.

Three new oleanane-type triterpenes, (23Z)-coumaroylhederagenin (1), (23E)-coumaroylhederagenin (2), and (3Z)-coumaroylhederagenin (3), together with two known triterpene acids, oleanolic acid and ursolic acid, have been isolated from the whole plant of Ludwigia octovalvis, and their structures have been elucidated by spectroscopic methods. All three new triterpenes showed significant cytotoxicity against two human tumor cell lines, namely, oral epidermoid carcinoma KB and colorectal carcinoma HT29, and gave IC(50) values in the range 1.2-3.6 microM.

Antineoplastic Agents, Phytogenic↗
PubMed2004

Cytotoxic triterpenoids from Acridocarpus vivy from the Madagascar rain forest.

Bioassay-guided fractionation of the cytotoxic MeOH extract obtained from Acridocarpus vivy led to the isolation of five new triterpenoids, acridocarpusic acids A-E (1-5); three known triterpenoids, moronic acid (6), ursolic acid, and oleanolic acid; and two known flavonoids, 4',5-dihydroxy-7-methoxyflavone and 4',5-dihydroxy-3',7-dimethoxyflavone. The structures of the new compounds 1-5 were established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. Compound 3 showed significant cytotoxic activity in the A2780 assay, with an IC50 value of 0.7 microg/mL.

Antineoplastic Agents, Phytogenic↗