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PubMed1998

Corosolic acid isolated from the fruit of Crataegus pinnatifida var. psilosa is a protein kinase C inhibitor as well as a cytotoxic agent.

Corosolic acid isolated from the fruit of Cratoegus pinnatifida var. psilosa was tested for anticancer activity. Corosolic acid displayed about the same potent cytotoxic activity as ursolic acid against several human cancer cell lines. In addition, the compound displayed antagonistic activity against the phorbol ester-induced morphological modification of K-562 leukemic cells, indicating the suppression of protein kinase C (PKC) activity by the cytotoxic compound. The compound showed PKC inhibition with dose-dependent pattern in an in vitro PKC assay.

Antineoplastic Agents, Phytogenic↗
PubMed2005

HPLC quantification of two isomeric triterpenic acids isolated from Mitracarpus scaber and antimicrobial activity on Dermatophilus congolensis.

Oleanolic (OA) and ursolic acids (UA) were isolated for the first time from the alcoholic extract of Mitracarpus scaber possessing antimicrobial effects on Dermatophilus congolensis. These two triterpenic acids were also active (MIC 15 microg/ml) on this causative agent of dermatophilosis in African animals. To quantify OA and UA in M. scaber, a new, simple and rapid high-performance liquid chromatography (HPLC) method compatible with MS detection was developed and validated. The mobile phase acetonitrile:H2O (85:15, v/v) was pumped through a C18 octadecylsilyl silica column at a flow rate of 0.6 ml/min and the eluate was monitored at 215 nm. The calibration curves constructed between 0.5 and 10 microg/ml showed linear relationships with good R2 values. The developed method was precise and reproducible with relative standard deviations (RSD) for these two active constituents between 0.22-2.06% (intraday) and 1.61-3.72% (interday) for concentrations from 0.5 to 6 microg/ml. Limits of detection and quantification were, respectively, 0.2 and 0.5 microg/ml.

Anti-Bacterial Agents↗
PubMed2005

Determination of glycyrrhetic acid in human plasma by LC-ESI-MS.

A sensitive liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) method for determination of glycyrrhetic acid, the active metabolite of glycyrrhizin, in human plasma using ursolic acid as the internal standard (IS) was established. Plasma was extracted with ethyl acetate and separated on a C18 column with a mobile phase of 10 mmol/l ammonium acetate-acetonitrile (10:90). Glycyrrhetic acid was determined using electrospray ionization in a single quadrupole mass spectrometer. HPLC-ESI-MS was performed in the selected ion monitoring (SIM) mode using target ions at m/z 469.5 for glycyrrhetic acid and m/z 455.5 for IS. Calibration curve was linear over the range of 0.1-400 ng/ml. The limit of quantitation for glycyrrhetic acid in plasma was 0.1 ng/ml. The mean plasma extraction recovery of glycyrrhetic acid was 94.51 +/- 3.82%. The method has been successfully applied to study the pharmacokinetics of glycyrrhetic acid in healthy male Chinese volunteers. The assay was proved to be sensitive, accurate and convenient.

Adult↗
PubMedDate not supplied

Chemosensitization and radiosensitization of tumors by plant polyphenols.

The treatment of cancer with chemotherapeutic agents and radiation has two major problems: time-dependent development of tumor resistance to therapy (chemoresistance and radioresistance) and nonspecific toxicity toward normal cells. Many plant-derived polyphenols have been studied intently for their potential chemopreventive properties and are pharmacologically safe. These compounds include genistein, curcumin, resveratrol, silymarin, caffeic acid phenethyl ester, flavopiridol, emodin, green tea polyphenols, piperine, oleandrin, ursolic acid, and betulinic acid. Recent research has suggested that these plant polyphenols might be used to sensitize tumor cells to chemotherapeutic agents and radiation therapy by inhibiting pathways that lead to treatment resistance. These agents have also been found to be protective from therapy-associated toxicities. How these polyphenols protect normal cells and sensitize tumor cells to treatment is discussed in this review.

Animals↗
PubMed2005

[Studies on the chemical constituents in herb of Mentha haplocalyx].

OBJECTIVE: To study the chemical constituents of Mentha haplocalyx. METHOD: The chemical constituents were isolated and purified with column chromatography and the structures were elucidated by spectral analysis. RESULT: Nine compounds were obtained and identified as emodin (I), chrysophanol (II), physcione (II), benzoic acid (IV), trans-cinnamic acid (V), beta-sitosterol (VI), aloe-emodin (VII), ursolic acid (VIII) and daucosterol (IX). CONCLUSION: Compounds I, II, III, V, VII were first isolated from M. haplocalyx.

Anthraquinones↗
PubMed2004

A new pentacyclic triterpenoid glucoside from Prunus serrulata var. spontanea.

A new triterpenoid, 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (4) along with four known triterpenoids, ursolic acid (1), 2alpha-hydroxyursolic acid (2), 2alpha,3alpha,24-trihydroxyurs-12-en-28-oic acid (3), and 2alpha,3alpha,19alpha,24-tetrahydroxyurs-12-en-28-oic acid-28-O-beta-D-glucopyranosyl ester (5), were isolated from the leaves of Prunus serrulata var. spontanea (Rosaceae). Compounds 3-5 showed ONOO(-) scavenging activity, whereas compounds 1 and 2 were virtually inactive.

Free Radical Scavengers↗
PubMed2004

In vitro anti-inflammatory activity of 23-hydroxyursolic acid isolated from Cussonia bancoensis in murine macrophage RAW 264.7 cells.

In the present study, the effects of various triterpenoids isolated from the stem bark of Cussonia bancoensis, namely, ursolic acid ( 1), 23-hydroxyursolic acid ( 2), 3-O-alpha- L-arabinopyranosyl-23-hydroxyursolic acid (3), and 3-O-beta-D-glucopyranosyl-23-hydroxyursolic acid ( 4) were evaluated on lipopolysaccharide (LPS)-induced nitric oxide (NO) and prostaglandin E (2) (PGE (2)) release by the macrophage cell line RAW 264.7. Of the tested triterpenoids, 23-hydroxyursolic acid ( 2) was found to be the most potent inhibitor of NO production, and also significantly reduced PGE (2) release. Consistent with these observations, the protein and mRNA expression levels of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2 enzymes were inhibited by 23-hydroxyursolic acid ( 2) in a concentration-dependent manner. Furthermore, 23-hydroxyursolic acid ( 2) inhibited the LPS-induced DNA binding activity of nuclear factor- kappaB (NF- kappaB), which was associated with a decrease of p65 protein levels in the nucleus. These results suggest that the 23-hydroxyursolic acid-mediated inhibition of iNOS and COX-2 expression, via blocking NF- kappaB activation, may mechanistically responsible for the anti-inflammatory effects of Cussonia bancoensis stem bark in vitro.

Animals↗
PubMed1999

Antioxidant flavonoids and chlorogenic acid from the leaves of Eriobotrya japonica.

The antioxidant activity of Eriobotrya japonica was determined by measuring the radical scavenging effect on DPPH (1,1-diphenyl-2-picrylhydrazyl) radical and lipid peroxidation produced when mouse liver homogenate was exposed to the air at 37 degrees C, using 2-thiobarbituric acid (TBA). The methanol extract and its fractions of Eriobotrya japonica leaves showed strong antioxidant activity. The antioxidant activity of EtOAc and n-BuOH soluble fractions were stronger than the others, and were further purified by repeated silica gel, MCl gel CHP-20P, and Sephadex LH-20 column chromatography. Antioxidant chlorogenic acid, quercetin-3-sambubioside from n-BuOH fraction, and methyl chlorogenate, kaempferol- and quercetin-3-rhamnosides, together with the inactive ursolic acid and 2 alpha-hydroxyursolic acid from EtOAc fraction were isolated. Antioxidant flavonoids and chlorogenic acid also showed prominent inhibitory activity against free radical generation in dichlorofluorescein (DCF) method.

Animals↗
PubMed2004

Triterpenoids from Acanthopanax koreanum root and their inhibitory activities on NFAT transcription.

Two triterpenoids (1,4) and two triterpenoid glycosides (2,3) were isolated from the root of Acanthopanax koreanum (Araliaceae). Their structures were identified as impressic acid (1), acankoreoside A (2), 3-epi-betulinic acid 28-O-[alpha-L-rhamnopyranosyl(1 --> 4)-beta-D-glucopyranosyl(1 --> 6)]-beta-D-glucopyranosyl] ester (3), and ursolic acid (4) by physicochemical and spectroscopic methods. Of these compounds, impressic acid (1) exhibited a potent inhibitory activity against NFAT transcription factor (IC50: 12.65 microM).

DNA-Binding Proteins↗
PubMed1998

Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.

Oleanolic acid (1) was identified as an anti-HIV principle from several plants, including Rosa woodsii (leaves), Prosopis glandulosa (leaves and twigs), Phoradendron juniperinum (whole plant), Syzygium claviflorum (leaves), Hyptis capitata (whole plant), and Ternstromia gymnanthera (aerial part). It inhibited HIV-1 replication in acutely infected H9 cells with an EC50 value of 1.7 microg/mL, and inhibited H9 cell growth with an IC50 value of 21.8 microg/mL [therapeutic index (T. I.) 12.8]. Pomolic acid, isolated from R. woodsii and H. capitata, was also identified as an anti-HIV agent (EC50 1.4 microg/mL, T. I. 16.6). Although ursolic acid did show anti-HIV activity (EC50 2.0 microg/mL), it was slightly toxic (IC50 6.5 microg/mL, T. I. 3.3). A new triterpene (11) was also isolated from the CHCl3-soluble fraction of R. woodsii, though it showed no anti-HIV activity. The structure of 11 was determined to be 1beta-hydroxy-2-oxopomolic acid by spectral examination. Based on these results, we examined the anti-HIV activity of oleanolic acid- or pomolic acid-related triterpenes isolated from several plants. In addition, we previously demonstrated that derivatives of betulinic acid, isolated from the leaves of S. claviflorum as an anti-HIV principle, exhibited extremely potent anti-HIV activity. Accordingly, we prepared derivatives of oleanolic acid and evaluated their anti-HIV activity. Among the oleanolic acid derivatives, 18 demonstrated most potent anti-HIV activity, with an EC50 value of 0. 0005 microg/mL and a T. I. value of 22 400.

Anti-HIV Agents↗
PubMed1995

Mechanism of 5-lipoxygenase inhibition by acetyl-11-keto-beta-boswellic acid.

The formation of 5-lipoxygenase (EC 1.13.11.34) products from endogenous substrate by intact rat neutrophilic granulocytes and from exogenous arachidonic acid by rat granulocyte 105,000 x g supernatants and affinity chromatography-purified human leukocyte 5-lipoxygenase was inhibited by acetyl-11-keto-beta-boswellic acid (IC50 values of 1.5 microM, 8 microM, and 16 microM, respectively). With other pentacyclic triterpenes lacking the 11-keto function and/or the carboxyl function on ring A (e.g., amyrin and ursolic acid), no 5-lipoxygenase inhibition was observed. The presence of the noninhibitory pentacyclic triterpenes both in intact cells and in the cell-free system caused a concentration-dependent reversal of the 5-lipoxygenase inhibition by acetyl-11-keto-beta-boswellic acid, whereas the inhibitory actions of 5-lipoxygenase inhibitors from different chemical classes (MK-886, L-739,010, ZM-230,487, and nordihydroguaiaretic acid) were not modified. The inhibition by acetyl-11-keto-beta-boswellic acid and the antagonism by noninhibitory pentacyclic triterpenes were not due to nonspecific lipophilic interactions, because lipophilic four-ring compounds (cholesterol, cortisone, and testosterone) neither inhibited the activity of the 5-lipoxygenase nor antagonized the inhibitory action of acetyl-11-keto-beta-boswellic acid. Therefore, we conclude that acetyl-11-keto-beta-boswellic acid acts directly on the 5-lipoxygenase enzyme at a selective site for pentacyclic triterpenes that is different from the arachidonate substrate binding site.

Animals↗
PubMed2006

New cytotoxic 6-oxygenated 8,9-dihydrofurocoumarins, hedyotiscone A - C, from Hedyotis biflora.

Using the bioactivity-guided fractionation method, three new 6-oxygenated 8,9-dihydrofurocoumarin-type compounds, hedyotiscones A, B, and C were isolated from the methanol extract of Hedyotis biflora together with seven known compounds. The structures of all isolated compounds were determined on the basis of mass and spectroscopic evidence. Compounds, oleanolic acid, and 6'-(beta-sitosteryl-3- O-beta- D-glucopyranosidyl) pentadecanoate showed marginal cytotoxicity against Hep G2 cells (human liver cancer cells) with IC50 values of 14.4, 17.4, 4.9, 8.0, and 9.2 microg/mL, respectively. Ursolic acid showed significant cytotoxicity against MDA-MB-231 cells (human breast carcinoma cells) with an IC50 value of 1.49 microg/mL.

Antineoplastic Agents, Phytogenic↗
PubMed2005

A new triterpene from Luculia pinciana Hook.

A new triterpene named luculiaoic acid A (1), showing inhibitory activity of a leukaemia cell line, along with eleven known compounds, has been isolated from the ethyl acetate extract of the stems of Luculia pinciana Hook. All the structures were elucidated on the basis of NMR, MS, and IR methods. The activity to inhibit Staphylococcus aureus and Candida albicans of all compounds showed that ursolic acid inhibits the growth of Staphylococcus aureus with an MIC of 0.5 mg ml(-1) and an MBC of 10 mg ml(-1), and scopletin inhibits Candida albicans with an MIC of 1 mg ml(-1) and an MBC of 5 mg ml(-1).

Anti-Infective Agents↗
PubMed2002

Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740.

The sesquiterpenes cadina-4,10(15)-dien-3-one (1) and aromadendr-1(10)-en-9-one (squamulosone) (14) along with the triterpenoid methyl ursolate (21) were incubated with the fungus Mucor plumbeus ATCC 4740. Substrates 1, 14 and ursolic acid (20) were isolated from the plant Hyptis verticillata in large quantities. M. plumbeus hydroxylated 1 at C-12 and C-14. When the iron content of the medium was reduced, however, hydroxylation at these positions was also accompanied by epoxidation of the exocyclic double bond. In total nine new oxygenated cadinanes have been obtained. Sesquiterpene 14 was converted to the novel 2alpha,13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3beta,7beta,21beta-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3beta,28-dihydroxyurs-12-ene (uvaol) (23) and 3beta,28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however.

Lamiaceae↗
PubMedDate not supplied

Modulation of in vitro biomarkers of the carcinogenic process by chemopreventive agents.

A structurally diverse group of chemopreventive agents was evaluated using in vitro biomarkers of the carcinogenesis process. With cultured human bronchial epithelial (BEAS-2B) cells, sulfur-containing compounds such as 1.2-dithiole-3-thione and sulforaphane, and phenolic compounds such as caffeic acid phenethyl ester and genistein, showed potent inhibition of benzo(a)pyrene [B(a)P] metabolite-DNA binding. Phenolic compounds also demonstrated strong antioxidant activity. Most of the test compounds did not inhibit 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase (ODC) activity with cultured mouse epidermal ME 308 cells, with the exception of sulfur-containing compounds, 1,2-dithiole-3-thione and sulforaphane, and a selenium compound, 1,4-phenylenebis (methylene)selenocyanate. With cultured Hepa 1c1c7 cells, sulforaphane and 1,2-dithiole-3-thione mediated strong induction of quinone reductase, and genistein and ursolic acid were moderate inducers. Chalcone, 1,4-phenylenebis (methylene)selenocyanate and caffeic acid phenethyl ester induced HL-60 cell differentiation. Interestingly, sulforaphane and caffeic acid phenethyl ester inhibited the total metabolism of benzo(a)pyrene with cultured BEAS-2B cells, and the distribution pattern of water-soluble metabolites was altered in comparison with the control groups. These data are suggestive of pleiotropic mechanisms that should prove beneficial when considering the chemopreventive activity of these substances. As a result, of the group of 25 agents tested, four were judged as superior cancer chemopreventive agents: caffeic acid phenethyl ester, 1,2-dithiole-3-thione, genistein, and sulforaphane.

Animals↗
PubMed1999

Modulatory effects of ixora coccinea flower on cyclophosphamide-induced toxicity in mice.

The active fraction of Ixora coccinea flowers showed chemoprotective effects on cyclophosphamide - induced toxicity by increasing the life span of treated mice, preventing body weight loss and maintaining near normal leucocyte and haemoglobin levels compared with cyclophosphamide treated controls. Decreased serum glutamate pyruvate transaminase (SGPT) and serum alkaline phosphatase (SAKP) levels in the Ixora coccinea treated groups indicated protection against hepatic toxicity. The active fraction was identified by phytochemical methods as the triterpenoid, ursolic acid.

Alanine Transaminase↗
PubMed2000

Antimalarial activity of four plants used in traditional medicine in Mali.

Mitragyna inermis (De Willd.) O. Kuntze Rubiaceae, Nauclea latifolia (Sm.) Rubiaceae, Glinus oppositofolius (Linn) Molluginaceae and Trichilia roka (Forsk.) Chiv. Meliaceae were investigated for their in vitro antimalarial activity. Leaves, roots and stem barks were submitted to aqueous, hydromethano and chloroform extractions and antimalarial activity was evaluated by microscopic and flow cytometric analysis. The results present evidence that the alkaloids contained in chloroform extracts and ursolic acid, purified from the hydromethanol extract of M. inermis induced a significant decrease of parasite proliferation. However, aqueous extracts, traditionally used for medication did not show high antimalarial activity. Statistical comparison between microscopic and cytometric analysis demonstrated the validity of this new technique for the screening of active antimalarial compounds isolated from plants.

Animals↗
PubMed2000

Aspects of the male reproductive toxicity/male antifertility property of andrographolide in albino rats: effect on the testis and the cauda epididymidal spermatozoa.

Previous work has shown that Andrographis paniculata leaf, when fed to male albino rats, causes the arrest of spermatogenesis. The present study was undertaken to investigate whether andrographolide, one of the major constituents of this plant, is responsible for such an effect. The compound was administered to 3-month-old male Wistar albino rats at two dose levels, for 48 days. Fertility tests, analysis of the counts, motility and abnormalities of the cauda epididymidal spermatozoa, and histopathological-evaluation of the testis were carried out. The results showed that sperm counts decreased, the spermatozoa were not motile, and several of them possessed abnormalities. The seminiferous epithelium was-thoroughly disrupted and in the seminiferous tubules, fully differentiated spermatozoa were far too limited; cells in the divisional stages were prevalent; multinucleate giant cells were abundant and Leydig cells appeared intact. It is inferred that andrographolide could affect spermatogenesis by preventing cytokinesis of the dividing spermatogenic cell lines. The multinucleate giant cells are comparable to the symplasts generated by cytochalasin-D and ursolic acid due to action at stages V-VII of the spermatogenic cycle. Sertoli cell damage and spermatotoxic effects are also apparent. Thus, the study points to a male reproductive toxic effect of this compound when used as a therapeutic; the study also confirms the possible prospective use of andrographolide in male contraception.

Animals↗