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At least 343 records · Page 19Linked to original sources
PubMed2004

Novel delta2-isoxazolines as group II phospholipase A2 inhibitors.

The synthesized imidazolyl substituted delta2-isoxazolines were subjected to Phospholipase A(2) (PLA(2)) enzyme inhibitory activity against snake venom source and their structure-activity relationship with respect to different groups attached to this moiety is reported for the first time. The crystal structure of the compound 2-butyl-5-chloro-3H-imidazolyl-4-carbaldehyde oxime 2, an intermediate for the construction of isoxazolines is reported. These compounds exerted a significant PLA(2) enzyme inhibitory activity against group II PLA(2). The in vivo activity on mice of selected compounds 3bI and 3bIV shows the comparable anti-inflammatory activity with the known standard ursolic acid.

Aldehydes↗
PubMed2006

[Studies on involatile constituents of Mentha haplocalyx].

OBJECTIVE: To promote its comprehensive utilization, the involatile constituents of Mentha haplocalyx were studied systematically. METHOD: The chemical components were isolated and purified by silca gel column chromatography and recrystallization. The chemical structures were elucidated on the basis of physico-chemical properties and spectral data. RESULT: Eight compounds were isolated and identified as: acacetin (I), tilianine (II), linarin (III), n-butyl-beta-D-fructopyranoside (IV), ursolic acid (V), oleanolic acid (VI), beta-sitosterol (VII), daucosterol (VIII). CONCLUSION: Compounds I approximately V were obtained from this plant for the first time.

Flavones↗
PubMed2005

[Study on chemical constituents from stem of Mallotus apelta].

Eight compounds were isolated from the ethyl-acetate extract of the stem of Mallotus apelta Muell. -Arg. The structures of eight compounds were identified by means of spectroscopic analysis as 12-ursen-3-one (I), 3-hydroxy-12-ursen (II), mussaenoside (III), 6-methoxy-2H-1-benzopyron4-one (IV), ursolic acid (V), acetyl aleuritolic acid (VI), beta-sitosterol-3-O-beta-D-glucopyranoside (daucosterol VII), beta-sitosterol (VII). Compound I to approximately V were obtained from this plant for the first time.

Chromatography, Thin Layer↗
PubMed2003

Biomass segregation in sage cell suspension culture.

The biomass of sage (Salvia officinalis L.) cell suspension culture was composed of single cells and cell aggregates. The development of aggregated cell culture from a single-cell suspension was monitored by particle size distribution for four particle size classes. Particle size distribution was compared between the biomass grown in bioreactor and shake flasks. The size of the particles had a strong influence on content of secondary metabolite, ursolic acid (UA). The single cell biomass fraction accumulated up to 7.7 mg UA g(-1) DW which was up to 50 times higher compared to aggregated biomass fractions.

Biomass↗
PubMed2001

[Studies on chemical constituents of Gaultheria leucocarpa var. Yunnanensis (Franch.) T. Z. Hsu & R. C. Fang].

OBJECTIVE: To separate and identify the chemical constituents of the aerial part of Gaultheria leucocarpa var. yunnanensis. METHOD: The compounds were extracted with solvents, isolated by column chromatography and identified by spectral analysis. RESULT: Four compounds were identified as n-dotriacontane and its homologous compound(1), ursolic acid(2), vanillic acid(3), and quercitrin(4). CONCLUSION: The compounds 1, 4 were obtained from the plant for the first time, and 2 and 3 were from above-ground part of the plant for the first time.

Alkanes↗
PubMed1999

Inhibitory effect of triterpenes from Crataegus pinatifida on HIV-I protease.

The methanol extracts of the leaves of Crataegus pinnatifida showed potent inhibitory activities against HIV-1 protease at a concentration of 100 micrograms/ml. The subsequent fractionation and isolation of the extract gave two active compounds. Their structures were identified as uvaol (1) and ursolic acid (2) by spectral data. These active compounds inhibit HIV-1 protease with IC50 values of 5.5 and 8.0 microM, respectively.

Anti-HIV Agents↗
PubMed2002

Antiviral and antioxidant activity of flavonoids and proanthocyanidins from Crataegus sinaica.

The antiviral and antioxidant activity of some fractions and of a series of flavonoids and proanthocyanidins obtained from Crataegus sinaica (Rosaceae) was evaluated. The O-glycosidic flavonoids and the oligomeric proanthocyanidins exhibited significant inhibitory activity against herpes simplex virus type 1 (HSV-1), which was shown to be due to an extracellular mechanism for procyanidin C-1. Procyanidin C-1 also had the highest antioxidant activity in both the microsomal lipid peroxidation and the hydroxyl radical scavenging assay. In addition to the previously reported phenolic compounds, the pentacyclic triterpenoid ursolic acid (1) and a tetrameric (2) and pentameric procyanidin (3) are reported for the first time.

Animals↗
PubMed2006

[Studies on the chemical constituents from stem of Chirita longgangensis var. Hongyao].

OBJECTIVE: To isolate and elucidate the constituents from stem of Chirita longgangensis var. hongyao. METHOD: The constituents were extracted with methanol and isolated by chromatography on silica gel, Sephadex LH-20 and ODS. The structures were determined by NMR and MS spectral analysis. RESULT: Seven compounds were identified as 2-hydroxy-7-methyl-9, 10-anthraquinone (1), 2-methyl-9, 10-anthraquinone (tectoquinone) (2), ursolic acid (3), vanillic acid (4), beta-sitosteryl-D-glucoside-6'-palmitate (5), beta-sitosterol (6), daucosterol (7), respectively. CONCLUSION: Compounds 1, 2, 3 and 5 were isolated for the first time from the family Gesneriaceae, compounds 4 and 6 were isolated for the first time from the genus Chirita, and compound 7 was isolated for the frist time from Chirita longgangensis var.

Anthraquinones↗
PubMedDate not supplied

Terpenoids and sterols from Nepeta cataria L. var. citriodora (Lamiaceae).

Isolation and GC/MS quantitative determination of ursolic acid in the herb of Nepeta cataria var. citriodora have been performed. The content of this compound was in the range 0.95-1.30%. Daucosterol (beta-sitosterol 3-O-beta-D-glucoside) was also isolated from the plant, in addition to small amounts of beta-sitosterol, campesterol, alpha-amyrin and beta-amyrin. The content and composition of essential oil in samples of the Nepeta cataria var. citriodora herb have been analysed as well.

Gas Chromatography-Mass Spectrometry↗
PubMed2003

Epicuticular waxes from caatinga and cerrado species and their efficiency against water loss.

The effects of the contents and chemical composition of the foliar epicuticular waxes of species from the caatinga (Aspidosperma pyrifolium, Capparis yco, Maytenus rigida and Ziziphus joazeiro) and cerrado (Aristolochia esperanzae, Didymopanax vinosum, Strychnos pseudoquina and Tocoyena formosa) were evaluated as to the resistance to water loss by means of an experimental device constructed for this purpose. In general, the waxes of the caatinga species investigated were more efficient against water loss than cerrado species. Increase of the thickness of the waxy deposits from 40 to 90 microg.cm-2 had no significant effect on the resistance to water loss. The chemistry of the wax constituents was shown to be an important factor to determine the degree of resistance to evaporation. n-Alkanes and alcoholic triterpenes were the most efficient barriers, while hentriacontan-16-one (a ketone) and ursolic acid (an acid triterpene) revealed low efficiency. The higher efficiency of the waxes of the leaves from caatinga species (mainly those of C. yco and Z. joazeiro) is probably accounted for the predominance of n-alkanes in their composition. The lower efficiency of the waxes of A. pyrifolium (caatinga), T. formosa and A. esperanzae (both species from the cerrado) is probably a consequence of the predominance of triterpenoids in the waxes of the two former species and hentriacontan-16-one in the latter.

Brazil↗
PubMed2004

A new 3,4-seco-lupane derivative from Lasianthus gardneri.

A new seco-ring A lupane triterpene derivative (1), along with lupenone, lupeol, beta-sitosterol, ursolic acid, and stigmasterol 3-O-beta-d-glucoside, were isolated from a methanol extract of mature stems of Lasianthus gardneri, a shrub from the family Rubiaceae growing in Sri Lanka. The structure and stereochemistry of the new compound were determined using a combination of (13)C and (1)H homo- and heteronuclear 2D NMR experiments and from mass spectral data. The structure of 1 was confirmed by partial synthesis from lupeol.

Glucosides↗
PubMed2000

Retention of cytoplasmic droplet by rat cauda epididymal spermatozoa after treatment with cytotoxic and xenobiotic agents.

Spermatozoa leaving the testis contain a cytoplasmic droplet which they release during transit through the epididymis before reaching the cauda epididymidis. The cytoplasmic droplet shows P450 aromatase activity, which plays a role in synthesis of oestrogen from androgen. In the present study, 3-month-old Wistar strain male albino rats were administered with the organophosphate insecticides malathion or dichlorvos, or the phytotherapeutics andrographolide or ursolic acid. Segments of the epididymis were subjected to histopathological and ultrastructural analyses and it was found that 60-95% of the spermatozoa residing in the lumen of the cauda epididymidis retained the cytoplasmic droplet. The motility of the spermatozoa released from the cauda epididymidis was inhibited. One of the mechanisms of action of these toxicants on male reproductive function may be attributed to the retention of the cytoplasmic droplet and the resultant impairment of sperm motility.

Animals↗
PubMedDate not supplied

Influence of the parasite Viscum cruciatum Sieber on the chemical constituents of Crataegus monogyna Jacq.

A phytochemical study of two plant species, Viscum cruciatum Sieber and Crataegus monogyna Jacq., was completed to investigate the influence of the parasite Viscum cruciatum on the host Crataegus monogyna. The study was carried out with two samples and consisted of hexane extracts of the Viscum cruciatum parasitizing on Crataegus monogyna and C monogyna. In these samples ursolic acid, beta-sitosterol and a triterpene fraction were found that contained mainly butyrospermol (3beta-lanost 8, 24-dien, 3-ol), 24-methylene-24-dihydrolanosterol (24-methylene-5alpha-lanost-8-en-3beta-ol), cycloartenol (9beta, 19-cyclo-5alpha, 9beta-lanost-24-en-3beta-ol), beta-amyrin (olean-12-en-3beta-ol) and several aliphatic alcohols identified as the C18 to C30 members of the 1-alkanol homologous series. beta-Amyrin acetate was only isolated from Viscum cruciatum and was not found in Crataegus monogyna.

Alcohols↗
PubMed2003

The role of hydrogen peroxide produced by polychlorinated biphenyls in PMR1-deficient yeast cells.

Polychlorinated biphenyls (PCBs) are well-known recalcitrant environmental pollutants. Although the metabolism of the PCBs has been intensively studied, very little is known about their mechanism of toxicity in living organisms or how they are degraded. We have examined the effects of PCBs on two different yeast strains to determine their mechanism of action. One yeast strain (K601, wild type) is resistant to the growth-inhibitory effect of PCBs, whereas the other strain (AA542, PMR1 mutant) is susceptible. PCBs increased the level of intracellular hydrogen peroxide in AA542 cells but not in K601 cells. In the presence of alpha-tocopherol or ursolic acid the growth of AA542 cells was not inhibited by treatment with PCBs. These results suggest that PCBs block cell growth through production of hydrogen peroxide in the PMR1 mutant strain, AA542. We compared superoxide dismutase (SOD), glutathione peroxidase (GPx), and catalase activities in both strains. The catalase activity in K601 cells was 10 times higher than that in AA542 cells. In contrast, there was no difference in activities of SOD and GPx between the two strains. Collectively, these observations indicate that oxidative stress causes the inhibition of cell growth observed in catalase-deficient yeast cells exposed to PCBs.

Benzene Derivatives↗
PubMed2005

Novel and simple nonaqueous capillary electrophoresis separation and determination bioactive triterpenes in Chinese herbs.

Three bioactive triterpenes ursolic acid, oleanolic acid and 2alpha,3beta,24-trihydroxy-urs-12-en-28-oic acid were simultaneously separated by nonaqueous capillary electrophoresis (NACE) with methanol:acetonitrile (65:35 v/v) mixture containing 90 mm trishydroxymethylaminomethane (Tris) at an applied voltage of +25 kV and a hydrodynamic injection of 5s. The effect of solvent composition, electrolyte nature and concentration on the electrophoretic behavior of the analytes were systematically studied. Separations were carried out in a fused-silica capillary tube with UV detection at 214 nm. Good separation and correlation coefficients were obtained. Meanwhile, the method was applied to separation and determination the three components in six Chinese herbs extraction. It is concluded that this method could be used for speedy and accurate qualitative and quantitative analysis of bioactive triterpenes in Chinese herbs.

Acetonitriles↗
PubMed2007

Insulin-mimetic and insulin-sensitizing activities of a pentacyclic triterpenoid insulin receptor activator.

Five pentacyclic triterpenoids isolated from Campsis grandiflora were tested for insulin-mimetic and insulin-sensitizing activity. The compounds enhanced the activity of insulin on tyrosine phosphorylation of the IR (insulin receptor) beta-subunit in CHO/IR (Chinese-hamster ovary cells expressing human IR). Among the compounds tested, CG7 (ursolic acid) showed the greatest enhancement and CG11 (myrianthic acid) the least. We characterized the effect of CG7 further, and showed that it acted as an effective insulin-mimetic agent at doses above 50 mug/ml and as an insulin-sensitizer at doses as low as 1 mug/ml. Additional experiments showed that CG7 increased the number of IRs that were activated by insulin. This indicates that a major mechanism by which CG7 enhances total IR auto-phosphorylation is by promoting the tyrosine phosphorylation of additional IRs. CG7 not only potentiated insulin-mediated signalling (tyrosine phosphorylation of the IR beta-subunit, phosphorylation of Akt and glycogen synthase kinase-3beta), but also enhanced the effect of insulin on translocation of glucose transporter 4 in a classical insulin-sensitive cell line, 3T3-L1 adipocytes. The results of the present study demonstrate that a specific pentacyclic triterpenoid, CG7, exerts an insulin-sensitizing effect as an IR activator in CHO/IR cells and adipocytes. The enhancement of insulin activity by CG7 may be useful for developing a new class of specific IR activators for treatment of Type 1 and Type 2 diabetes.

Adipocytes↗
PubMed2005

Simultaneous determination of seven triterpenoids and triterpenoid saponins in Folium llicis Purpureae by high performance liquid chromatography coupled with evaporative light scattering detection.

A new HPLC coupled with evaporative light scattering detection method was established for the simultaneous determination of seven triterpenoids and triterpenoid saponins in Folium Ilicis Purpureae traditional Chinese medicinal herb derived from the leaf of Ilex purpurea, namely, 3-omicron-beta-D-glucopyranosyl (1-->2)-beta-D-[6-omicron-methyl-glucuronopyranosyl]-28-omicron-beta-D-glucopyranosyl oleanolic acid (SQ-1), pedunculoside (SQ-2), 23-hydroxytormentic acid 28-omicron-beta-D-glucopyranoside (SQ-3), 23-hydroxytormentic acid (SQ-4), rutundic acid (SQ-5), ilexoside B (SQ-6), and ursolic acid (SQ-7). The optimal chromatographic conditions were achieved on a C18 column with a linear gradient elution of mobile phase A: deionized water-isopropyl alcohol-THF-acetic acid (90:10:6:1, v/v) and B: methanol-isopropyl alcohol-THF-acetic acid (90:10:6:1, v/v) at the flow rate of 1.0 mL/min; temperature for drift tube was set at 98degreesC and nitrogen flow rate was 2.8 L/min. All calibration curves of the seven compounds showed good linear regression (r2 > 0.995) within test ranges. The developed method has good repeatability for quantitation of all analytes interested with overall intraday and interday variation of less than 4.1%. The LOD (S/N = 3) and LOQ (S/N = 10) were less than 0.13 and 0.26 microg/mL, respectively, for all analytes. The established method was successfully used to evaluate the quality of Folium Ilicis Purpureae samples of different collections.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

Constituents of Quinchamalium majus with potential antitubercular activity.

Antitubercular bioassay-guided fractionation of the dichloromethane extracts of the above-ground biomass and roots of Quinchamalium majus led to the identification of six known constituents, betulinic acid (1), daucosterol (2), 5,7-dihydroxyflavone (3), oleanolic acid (4), (-)-2S-pinocembrin (5), and ursolic acid (6), for the first time in this species. Their chemical structures were determined on the basis of spectroscopic evidence and chemical transformation methods. All of these compounds along with additional 11 analogues were evaluated for their antitubercular potential against Mycobacterium tuberculosis in a microplate alamar blue assay, and the primary structure-activity relationships (SARs) for 4 and 6 were discussed. In addition, all the isolates were tested for cytotoxicity against African green monkey Vero cells in order to evaluate for their selectivity potential.

Animals↗