Comparative effects of salicylic acid, phenylbutazone, probenecid and other anions on the metabolism, distribution and excretion of indomethacin by rats.
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Acetates↗
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Antiviral activities of purified compounds from Youngia japonica (L.) DC (Asteraceae, Compositae).
The ethanol extract of a biannual medicinal herb, Youngia japonica (commonly known as Oriental hawk's beard) was reported previously to have potent antiviral activity against respiratory syncytial virus (RSV) cultured in HEp-2 cells. Three anti-microbial agents, namely 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and luteolin-7-O-glucoside were subsequently purified and chemically characterized from the ethanol extract of Youngia japonica. The two dicaffeoylquinic acids exhibited prominent anti-RSV with 50% inhibitory concentration (IC50) of 0.5 microg/ml in vitro. Luteolin-7-O-glucoside together with the two dicaffeoylquinic acids were also manifested to have some antibacterial activity towards the causal agents of food-borne disease, namely Vibrio cholerae and Vibrio parahaemolyticus at the concentration of 2mg/ml. Bacillus cereus was sensitive to 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid only, but not to luteolin-7-O-glucoside.
Antiviral Agents↗
Irreversible inhibition of human immunodeficiency virus type 1 integrase by dicaffeoylquinic acids.
Human immunodeficiency virus type 1 (HIV-1) and other retroviruses require integration of a double-stranded DNA copy of the RNA genome into the host cell chromosome for productive infection. The viral enzyme, integrase, catalyzes the integration of retroviral DNA and represents an attractive target for developing antiretroviral agents. We identified several derivatives of dicaffeoylquinic acids (DCQAs) that inhibit HIV-1 replication in tissue culture and catalytic activities of HIV-1 integrase in vitro. The specific step at which DCQAs inhibit the integration in vitro and the mechanism of inhibition were examined in the present study. Titration experiments with different concentrations of HIV-1 integrase or DNA substrate found that the effect of DCQAs was exerted on the enzyme and not the DNA. In addition to HIV-1, DCQAs also inhibited the in vitro activities of MLV integrase and truncated variants of feline immunodeficiency virus integrase, suggesting that these compounds interacted with the central core domain of integrase. The inhibition on retroviral integrases was relatively specific, and DCQAs had no effect on several other DNA-modifying enzymes and phosphoryltransferases. Kinetic analysis and dialysis experiments showed that the inhibition of integrase by DCQAs was irreversible. The inhibition did not require the presence of a divalent cation and was unaffected by preassembling integrase onto viral DNA. The results suggest that the irreversible inhibition by DCQAs on integrase is directed toward conserved amino acid residues in the central core domain during catalysis.
Animals↗
[Relationship between anatomical structure and metabolism of plant tissues. I. Differences between the qualitative and quantitative composition of phenolic substances of apple explants and that of callus and cells produced by the culture].
Relationship between anatomical structure and metabolism of plant tissues. I. Differences between the qualitative and quantitative composition of phenolic substances of apple-fruit explants and that of calli and cells cultured from these explants. Phenolic compounds of intact apple-fruits (CV. Golden delicious), fruit fragments cultured on agar medium, newly formed calli and cell suspensions prepared from these calli, were studied quantitatively and qualitatively. The phenol content of the tissues decreased during the first days of culture, then recovered practically the initial level just before the initiating calli became visible. This content is very low in the calli and in the cultured cells. But the most remarkable result is that the qualitative compositions of the phenols extracted from the fruit tissues, the calli and the cells were different : p-coumaryglucose, which is abundant in the fruit, disappeared almost completely in the calli, in which three compounds were formed de novo, X1 which was tentatively identified as ferulylquinic acid, X2, a glycoside of p-coumaric acid different from p-coumarylglucose, and X3 not yet identified; the cells synthesized also X1 and X3 but not X2, and contained no p-coumaryglucose while feruylquinic acid was abundant. The study on the processes of induction or regulation of the enzymes implied in these metabolic modifications is under way.
Agar↗
[Quinic acid esters from herba of Siphonostegia chinensis].
OBJECTIVE: To study the bioactive constituents, quinic acid esters, from Siphonostegia chinensis. METHOD: The compounds were extracted with solvents, isolated by various column chromatography and identified by spectroscopic methods. RESULT: Three quinic acid esters were isolated and identified as 3,4-di-O-caffeoylquinic acid(I), macranthoin F(II), and methyl ester of 3, 4,5-tri-O-caffeoylquinic acid (III). CONCLUSION: All compounds were isolated from Siphonostegia for the first time.
Chlorogenic Acid↗
A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase.
The phytochemical study of the aerial parts of Aster scaber Thunb. (Asteraceae) yielded a new caffeoyl quinic acid, (-) 3,5-dicaffeoyl-muco-quinic acid (2) and three known compounds, (-) 3,5-dicaffeoyl quinic acid (1), (-) 4,5-dicaffeoyl quinic acid (3), (-) 5-caffeoyl quinic acid (4). The structures were established by high resolution spectroscopic methods. The antiviral effects against HIV-1 integrase of the compounds was evaluated. (-) 3,5-Dicaffeoyl-muco-quinic acid (2) exhibited potent antiviral activity with an IC50 value of 7.0 +/- 1.3 microg/ml.
Asteraceae↗
Formation of novel flavonoids in apple (Malusxdomestica) treated with the 2-oxoglutarate-dependent dioxygenase inhibitor prohexadione-Ca.
Novel flavonoids were formed in young leaves of apple (Malusxdomestica) after treatment with the dioxygenase inhibitor prohexadione-Ca, which is known to reduce the incidence and severity of fire blight caused by Erwinia amylovora and other plant diseases. The compounds were isolated and identified as luteoliflavan, luteoliflavan 5-glucoside, eriodictyol 7-glucoside and 6"-O-trans-p-coumaroyleriodictyol 3'-glucoside. These flavonoids represent a novel biosynthetic pathway in apple leading to the formation of 3-deoxyflavans. Concomitantly, the content of regularly occurring phenylpropanoids is also influenced by prohexadione-Ca with increasing amounts of hydroxycinnamic acids and decreasing flavan-3-ols and flavonols. The altered flavonoid metabolism may be related to the lowered pathogen incidence though the isolated novel flavonoids do not exhibit antibacterial activity.
Chlorogenic Acid↗
[Advances in caffeoylquinic acid research].
This paper reviewed updated research progresses of caffeoylquinic acids both in phytochemical and pharmacological aspects. The resources, distribution as well as the chemical structures of monocaffeoylquinic acids, dicaffeoylquinic acids, tricaffeoylquinic acids and multicaffeoylquinic acids are conclusively analyzed. The reviewed pharmacological investigations indicated that the caffeoylquinic acids exhibited significant activities such as anti-oxidation, anti-inflammation, enzyme inhibition, hypatoprotective and anti-PAF effects. The broad distribution and the remarkably pharmacological activities of these natural phenolic acids indicated their potential in the discovery and development of new natural drugs.
Animals↗
Effects of coffee consumption on oxidative susceptibility of low-density lipoproteins and serum lipid levels in humans.
Since little is known about how coffee intake affects low-density lipoprotein (LDL) oxidative susceptibility and serum lipid levels, we conducted an in vivo study in 11 healthy male students of Wakayama Medical University aged between 20 and 31 years fed an average Japanese diet. On days 1-7 of the study, the subjects drank mineral water. On day 7, the subjects began drinking coffee, 24 g total per day, for one week. This was followed by a one week "washout period" during which mineral water was consumed. Fasting peripheral venous blood samples were taken at the end of each one-week period. LDL oxidation lag time was approximately 8% greater (p < 0.01) after the coffee drinking period than the other periods. Serum levels of total cholesterol and LDL-cholesterol (LDL-C) and malondialdehyde (MDA) as thiobarbituric acid reactive substances (TBARS) were significantly decreased after the coffee drinking period. Finally, regular coffee ingestion may favorably affect cardiovascular risk status by modestly reducing LDL oxidation susceptibility and decreasing LDL-cholesterol and MDA levels.
Adult↗
New chlorogenin hexasaccharide isolated from Agave fourcroydes with cytotoxic and cell cycle inhibitory activities.
A new chlorogenin hexasaccharide (1) was isolated from leaves of Agave fourcroydes (Agavaceae). The structure of the new saponin was elucidated as chlorogenin 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside] (1) by spectroscopic analysis and the result of acidic hydrolysis. The new saponin (1) as well as known hexasaccharides (3 and 5) isolated here showed cytotoxicity against HeLa cells, and 1 exhibited a cell cycle inhibitory effect at the G2/M stage at the concentration of 7.5 and 10 microg/mL.
Agave↗
Sexual dimorphism in urinary metabolite profiles of Han Wistar rats revealed by nuclear-magnetic-resonance-based metabonomics.
Gender-dependent metabolic variation in Han Wistar rats (n=25 male and n=25 female) was investigated using (1)H nuclear magnetic resonance (NMR) spectroscopy of urine coupled with chemometric methods. Statistically discriminatory regions of the spectra for male and female rats were identified and biomarker characterization was achieved by the further application of solid-phase extraction chromatography with NMR detection and high-performance liquid chromatography mass spectrometry. A novel discriminating molecule was identified as the sulfate conjugate of m-hydroxyphenylpropionic acid, which was excreted in higher concentrations by male rats. Other gender-related metabolite differences in the urine profiles included higher levels of trimethylamine-N-oxide, N,N'-dimethylglycine, m-hydroxyphenylpropionic acid, N-acetylglycoprotein, and cholate in samples from female animals. These studies emphasize the utility of multicomponent metabolic profiling for investigating physiological and genetic variation in experimental animals that may be of relevance to their use as models of toxicity and disease.
Animals↗
Naturally occurring proteasome inhibitors from mate tea (Ilex paraguayensis) serve as models for topical proteasome inhibitors.
Proteasome inhibitors have emerged as a clinically important therapy for neoplastic disease, with velcade, an organoboron compound used extensively in multiple myeloma. Recently, (-)-epigallocatechin gallate has been found to be a potent inhibitor of the proteasomal chymotrypsin-like activity. Other compounds that inhibit angiogenesis and are active as chemopreventive agents, such as curcumin, also inhibit proteasome activity. We have screened natural product extracts using ras-transformed endothelial cells (SVR cells) as a bioassay, and found that extracts of mate tea (Ilex paraguayensis) inhibit the growth of these endothelial cells. The extract was fractionated and found to have novel cinnamate esters that inhibit proteasome activity. Based upon the structures of the compounds isolated from mate tea, we examined synthetic analogs of these compounds for proteasome activity. Cinnamic acid amides had no inhibitory activity against proteasomes, whereas cinnamate esters displayed the activity. Based upon these findings, preclinical and clinical trials of topical cinnamate esters as proteasome inhibitors are warranted for psoriasis and other inflammatory disorders.
Cell Division↗
[Effects of the treatment of coffee pulp, fresh or ensilaged, with calcium hydroxide, on its nutritive value].
This study was carried out to determine the effects of the addition of calcium hydroxide on the chemical composition and nutritive value of fresh or ensilaged coffee pulp. Fresh or ensilaged pulp were mixed with 1, 2 and 3% of calcium hydroxide. The process was carried out during 0 and 16 hr, after which time the treated pulp was sun-dried for 36 hr until moisture content reached 12%. These samples were then analyzed for their proximate chemical composition and for some minerals (Ca, P, Na, K), as well as for caffeine, tannins and chlorogenic and caffeic acids content. Diets were then prepared from these materials, containing 15% protein and 15 or 30% fresh or ensilaged coffee pulp, and offered to weanling rats during six weeks. Information required on weight gain, food conversion, apparent digestibility and toxicity of the diets was recorded. Results of the chemical analysis revealed that the main changes found in both types of pulp as a result of the calcium hydroxide treatment were the following: a decrease in ether extract (from 4.0 to 2.5 g/100 g), crude fiber (from 18.3 to 11.9 g/100 g) and protein content (from 12.3 to 8.6 g/100 g) in an inverse relation to the amount of calcium hydroxide used. The amount of ash increased, fluctuated between 5.5 and 15.4%, depending on the amount of calcium hydroxide used. The latter affected the Ca:P ratio in the diets, where an average ratio of 7.2:1 was found in the control pulp (0% calcium hydroxide) and 59.0:1 in those treated with the highest amount of calcium hydroxide (3%). Regarding the caffeine, tannins and chlorogenic and caffeic acids contents, calcium hydroxide was effective in decreasing only tannins, more so in the fresh than in the ensilaged pulp; the decrease was in direct proportion to the amount of calcium hydroxide added and to the length of the Ca(OH)2 treatment. The results of the biological assays showed that the addition of Ca(OH)2 in either of the two time periods used and at either of the concentrations studied, did not improve the nutritive value of coffee pulp. There was always a better performance in the animals that consumed ensilaged pulp than in those fed fresh pulp. The animals fed 15% coffee pulp either fresh or ensilaged performed better than those consuming 30% coffee pulp.(ABSTRACT TRUNCATED AT 400 WORDS)
Animals↗
Effects of apple phenolics on the human metabolome: modulation of key metabolic pathways.
Apples are widely recognized for their potential health benefits, partly attributed to their phenolic compounds. However, their impact on human metabolism remains incompletely understood. This study investigated metabolic effects of apple-derived phenolic compounds using untargeted metabolomics approach across multiple biofluids. In a crossover intervention study, 30 healthy men consumed a phenolic-rich apple juice or a placebo for two weeks. Blood, urine and saliva samples were collected before and after each intervention and analyzed by direct infusion ultra-high resolution mass spectrometry. Consumption of apple phenolic compounds resulted in significant alterations of the human metabolome, including increased levels of phenolic-derived degradation products and microbial-associated metabolites across all biofluids. Pathway enrichment analysis revealed pronounced effects on phenylalanine and tyrosine metabolism, as well as linoleic and arachidonic acid metabolism, Overall, these findings demonstrate that apple phenolic compounds induce measurable, microbiota-associated and systemic metabolic changes, providing new insights into their metabolic fate and biological relevance.
Humans↗
In vivo antihepatotoxic effects of Ligularia fischeri var. spiciformis and the identification of the active component, 3,4-dicaffeoylquinic acid.
Pretreatment with a methanolic extract of Ligularia fischeri var. spiciformis (Compositae) herb inhibited hepatotoxicities caused by CCl4, D-galactosamine (GalN), alpha-naphthylisothiocyanate (ANIT), and DL-ethionine in rats. An ethyl acetate (EtOAc) extract fractionated from the methanolic extract showed a strong inhibitory effect. A major component, 3,4-dicaffeoylquinic acid (DCQA), isolated from the methanolic extract was examined for antihepatotoxicity. Pretreatment with DCQA (5 and 10 mg/kg, p.o.) significantly reduced serum aminotransferases (alanine and aspartate), sorbitol dehydrogenase, gamma-glutamyltransferase, alkaline phosphatase, and lactate dehydrogenase activities during CCl4- or GalN-induced hepatotoxicity, suggesting that DCQA is a major principle for the antihepatotoxic activity of L. fischeri var. spiciformis. DCQA also partially restored bile flow and reduced total bilirubin and cholic acid concentrations in rats with ANIT-induced cholestasis. Treatment with DCQA inhibited the increase in triglyceride, cholesterol, and total lipids in DL-ethionine-induced fatty liver. These results support the traditionally held belief that this plant can be used for the treatment of jaundice and hepatic failure.
1-Naphthylisothiocyanate↗
[Estimation of measurement uncertainty of analytical results for the determination of three active components from Gardenia jasminoides Ellis. by HPLC].
OBJECTIVE: To estimate the uncertainty for quantitative analysis results of geniposide, chloregenic acid and crocinl I in Gardenia jasminoides Ellis. METHODS: HPLC method was employed to determine the amounts of geniposide, choloregenic acid and crocinl I in Gardenia jasminoides Ellis. Analyzing the uncertainty sources arising from the procedure of analysis, the standard uncertainty and combined uncertainty and expanded uncertainty were calculated according to the data of HPLC. RESULTS: This method met the requirements of modern pharmaceutical analysis, and the expand uncertainties for the HPLC method of the three components are 0.1024, 0.2254, 0.1264, respectively. CONCLUSION: Applying measurement uncertainty to the evaluation of quantitative analysis results of active components in Gardenia jasminoides Ellis. is an improvement to the actual error evaluation system.
Algorithms↗
In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds.
The aim of this study was to search for new natural anti-HCV agents from Chinese herbal medicine. Bioactivity-guided extraction and isolation methods were used. Active part and pure compounds were obtained from ethanolic extract of Saxifraga melanocentra Franch. and their in vitro inhibitory activities (IC50) against HCV NS3 serine protease were tested by enzyme-linked immunosorbent assay. Results showed that the polyphenolic ethyl acetate part of the herbal extract was the most active, and from this 18 polyphenols representing active compounds were isolated and identified. IC50 values of these compounds and five related ones were obtained. A broad-degree of anti-HCV activity was observed among them in the following order: gallated esters of D-glucose and rutin (0.68-4.86 microM)> flavonoids (33.11-370.37 microM)> gallic acid and its methyl and ethyl esters, Bergenin and others (over 1000 microM). The most active compound was 1,2,3,4,6-penta-O-galloyl-beta-D-glucoside (0.68 microM). In conclusion, polyphenols were responsible for the anti-HCV constitution of S. melanocentra, and multigallated esters of D-glucose possessed the strongest inhibition against HCV NS3 serine protease and little cytotoxic effect, suggesting the potential use of these compounds for designing and developing drugs for treatment of the viral infection.
Animals↗
(-)-3,5-Dicaffeoyl-muco-quinic acid isolated from Aster scaber contributes to the differentiation of PC12 cells: through tyrosine kinase cascade signaling.
Aster scaber T. (Asteraceae) has been used in traditional Korean and Chinese medicine to treat bruises, snakebites, headaches, and dizziness. (-)-3,5-Dicaffeoyl-muco-quinic acid (DQ) isolated from A. scaber induced neurite outgrowth in PC12 cells. It has been reported that the activation of the extracellular signal regulated kinase 1/2 (Erk 1/2) and phosphoinositide 3 (PI3) kinase plays a crucial role in the NGF-induced differentiation of PC12 cells. This study showed that the effect of DQ on neurite outgrowth is mediated via the Erk 1/2 and PI3 kinase-dependent pathways like NGF. Furthermore, DQ stimulated the phosphorylation of Trk A. Overall, DQ elicited the differentiation of PC12 cells through Trk A phosphorylation followed by Erk 1/2 and PI3 kinase activation.
Animals↗