tiliroside and kaempferol

In this paper, the phytochemical analysis on the inflorescences (flowers and bracts) of a sample of

Topics: Classification; Flavonoids; Glucosides; Inflorescence; Italy; Kaempferols; Monosaccharides; Phytochemicals; Plant Extracts; Quercetin; Secondary Metabolism; Tilia

Topics: AMP-Activated Protein Kinases; Animals; Anti-Inflammatory Agents; Cell Line; Cytokines; Flavonoids; Heme Oxygenase-1; Inflammation; Kaempferols; Membrane Proteins; Mice; Microglia; NF-E2-Related Factor 2; Signal Transduction

An acylated flavonol glycoside, helichrysoside, at a dose of 10 mg/kg/day per os for 14 days, improved the glucose tolerance in mice without affecting the food intake, visceral fat weight, liver weight, and other plasma parameters. In this study, using hepatoblastoma-derived HepG2 cells, helichrysoside, trans-tiliroside, and kaempferol 3-O-β-D-glucopyranoside enhanced glucose consumption from the medium, but their aglycones and p-coumaric acid did not show this activity. In addition, several acylated flavonol glycosides were synthesized to clarify the structural requirements for lipid metabolism using HepG2 cells. The results showed that helichrysoside and related analogs significantly inhibited triglyceride (TG) accumulation in these cells. The inhibition by helichrysoside was more potent than that by other acylated flavonol glycosides, related flavonol glycosides, and organic acids. As for the TG metabolism-promoting activity in high glucose-pretreated HepG2 cells, helichrysoside, related analogs, and their aglycones were found to significantly reduce the TG contents in HepG2 cells. However, the desacyl flavonol glycosides and organic acids derived from the acyl groups did not exhibit an inhibitory impact on the TG contents in HepG2 cells. These results suggest that the existence of the acyl moiety at the 6'' position in the D-glucopyranosyl part is essential for glucose and lipid metabolism-promoting activities.

Topics: Acylation; Animals; Catechols; Cell Line, Tumor; Chromones; Flavonoids; Flavonols; Glucose; Glycosides; Hep G2 Cells; Humans; Kaempferols; Lipid Metabolism; Male; Mice; Plant Extracts; Structure-Activity Relationship

To study the chemical constituents from Mitrasacme pygmaea.. The compounds were isolated and purified by column chromatography and their structure were identified by NMR and MS,and comparison spectral data with literature.. Eleven compounds were isolated and identified as tricin-7-O-β-D-glucopyranoside( 1),massonianoid A( 2),kaempferol( 3),cinnamic acid( 4),quercetin( 5),tiliroside( 6),tricin( 7),β-sitosterol( 8),adenosine( 9),α-tocopherolquinone( 10)and β-daucosterol( 11).. All the compounds are isolated from this genus for the first time.

Topics: Flavonoids; Kaempferols; Magnoliaceae; Quercetin; Sitosterols

1. Absorption and metabolism of tiliroside (kaempferol 3-β-D-(6"-p-coumaroyl)-glucopyranoside) and its related compounds kaempferol, kaempferol-3-glucoside and p-coumaric acid were investigated in the small intestinal Caco-2 cell model. Apparent permeation (Papp) was determined as 0.62 × 10(-6) cm/s, 3.1 × 10(-6) cm/s, 0 and 22.8 × 10(-6) cm/s, respectively. 2. Mechanistic study showed that the transportation of tiliroside, kaempferol-3-glucoside and p-coumaric acid in Caco-2 model were transporter(s) involved, while transportation of kaempferol was solely by passive diffusion mechanism. 3. Efflux transporters, multi-drug-resistance-associated protein-2 (MRP2), were shown to play a role in limiting the uptake of tiliroside. Inhibitors of MRP2, (MK571 and rifampicin) and co-incubation with kaempferol (10 μM), increased transfer from the apical to the basolateral side by three to five fold. 4. Metabolites of kaempferol-3-glucoside and p-coumaric acid were not detected in the current Caco-2 model, while tiliroside was metabolised to a limited extent, with two tiliroside mono-glucuronides identified; and kaempferol was metabolised to a higher extent, with three mono-glucuronides and two mono-sulfates identified. 5. In conclusion, tiliroside was metabolised and transported across Caco-2 cell membrane to a limited extent. Transportation could be increased by applying MRP2 inhibitors or co-incubation with kaempferol. It is proposed that tiliroside can be absorbed by human; future pharmacokinetics studies are warranted in order to determine the usefulness of tiliroside as a bioactive agent.

Topics: ATP Binding Cassette Transporter, Subfamily B, Member 1; Biological Availability; Biological Transport; Caco-2 Cells; Coumaric Acids; Flavonoids; Humans; Intestinal Absorption; Intestine, Small; Kaempferols; Membrane Transport Proteins; Multidrug Resistance-Associated Proteins; Propionates; Time Factors

Phytochemical and antimicrobial activity study on the ethanol extract of the leaves and stems of Loropetalum chinense led to the isolation of a new flavan-3-ol compounds, 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]-catechin (loropetaliside A) (1) and a new lignan glucoside, 1-(5-hydroxy-3-methoxyphenyl)-2-(2-β-glucopyranosyl-4-hydroxy-5-(1-(E)propen-3-ol)-phenyl)-propane-3-ol (loropetaliside B) (3) and several known compounds manglieside D (2), quercetin (4), kaempferol-3-O-D-glucopyranoside (5), quercetin-3-O-β-L-rhamnoside (6) and tiliroside (7). Their structures were elucidated on the basis of extensive spectroscopic analysis.

Topics: Anti-Infective Agents; Bacteria; Flavonoids; Glucosides; Hamamelidaceae; Kaempferols; Lignans; Plant Extracts; Plant Leaves; Plant Stems; Quercetin

In an ongoing project to evaluate natural compounds isolated from plants from the Brazilian biodiversity as modulators of antibiotic resistance, kaempferol-3-O-beta-d-(6''-E-p-coumaroyl) glucopyranoside (tiliroside), isolated from Herissantia tiubae (Malvaceae) was investigated using the strain SA-1199B of Staphylococcus aureus, which overexpresses the norA gene encoding the NorA efflux protein which extrudes hydrophilic fluorquinolones and some biocides, such as benzalkonium chloride, cetrimide, acriflavine and ethidium bromide. The minimum inhibitory concentrations (MICs) of the antibiotics and biocides were determined by the microdilution assay in the absence and in the presence of sub-inhibitory concentration of tiliroside. Although tiliroside did not display relevant antibacterial activity (MIC = 256 microg/mL), it modulated the activity of antibiotics, i.e. in combination with antibiotics a reduction in the MIC was observed for norfloxacin (16-fold), ciprofloxacin (16-fold), lomefloxacin (four-fold) and ofloxacin (two-fold), and an impressive reduction in the MICs for the biocides (up to 128-fold). The results presented here represent the first report of a kaempferol glycoside as a putative efflux pump inhibitor in bacteria. The present finding indicates that H. tiubae (and broadly Malvaceae) could serve as a source of plant-derived natural products that modulate bacterial resistance, i.e. a source of potential adjuvants of antibiotics.

Topics: Anti-Bacterial Agents; Bacterial Proteins; Drug Resistance, Microbial; Drug Resistance, Multiple, Bacterial; Flavonoids; Genes, MDR; Glycosides; Kaempferols; Malvaceae; Microbial Sensitivity Tests; Plant Components, Aerial; Plant Extracts; Staphylococcus aureus

The 80% aqueous acetone extracts from the fruit (50 mg/kg/d) and seeds (12.5 and 25 mg/kg/d) of Rosa canina L., but not from the pericarps, were found to show substantial inhibitory effect on the gain of body weight and/or weight of visceral fat without affecting food intake in mice for 2 weeks after administration of the extracts. With regard to the active constituents, the principal constituent, trans-tiliroside (0.1-10 mg/kg/d), potently inhibited the gain of body weight, especially visceral fat weight, and significantly reduced blood glucose levels after glucose loading (1 g/kg, ip) in mice. On the other hand, kaempferol and p-coumaric acid lacked such effect and kaempferol 3-O-beta-D-glucopyranoside tended to reduce the gain of body weight and visceral fat weight, but not significantly, at a dose of 10 mg/kg/d. These results indicate the importance of both kaempferol 3-O-beta-D-glucopyranoside and p-coumaroyl moieties for anti-obese effects. Furthermore, a single oral administration of trans-tiliroside at a dose of 10 mg/kg increased the expression of PPAR-alpha mRNA of liver tissue in mice.

Topics: Acetone; Animals; Anti-Obesity Agents; Benzopyrans; Body Weight; Coumaric Acids; Flavonoids; Intra-Abdominal Fat; Kaempferols; Liver; Mice; Plant Extracts; PPAR alpha; Propionates; RNA, Messenger; Rosa; Structure-Activity Relationship; Water; Weight Gain

Mexican traditional medicine uses a great variety of plants in the treatment of gastrointestinal disorders such as diarrhea. In order to understand the properties of some of their chemical constituents, three flavonoids (kaempferol, tiliroside and (-)-epicatechin) isolated from Geranium mexicanum, Cuphea pinetorum, Helianthemum glomeratum, and Rubus coriifolius, were assayed to demonstrate their in vivo antiprotozoal activity; using an experimental infection of Giardia lamblia in suckling female CD-1 mice. Compounds tested showed antigiardial activity with values of ED(50) (micromol/kg) 0.072 for (-)-epicatechin, 2.057 for kaempferol and 1.429 for tiliroside. The most active flavonoid was the (-)-epicatechin, its activity was higher than metronidazole and emetine, drugs used as positive controls. In the case of kaempferol and tiliroside their potency was close to that of the metronidazole, but far less than emetine.

Topics: Animals; Benzopyrans; Catechin; Diarrhea; Female; Flavonoids; Giardia lamblia; Kaempferols; Medicine, Traditional; Mexico; Mice; Mice, Inbred Strains; Plants, Medicinal

To investigate the chemical constituents of Anaphalis sinica.. Various chromatographic techniques were employed for the isolation and purification of the constituents. The structures were elucidated by chemical and spectral analysis.. Six flavonoid compounds were isolated and identified as kaempferol, tiliroside, quercetin, quercetin -3-O-beta-D-glucosides, scutellarin, 5,7-dihydroxy-8-methoxyflavone and one pyrone were isolated and identified as helipyrone.. All of these compounds was isolated from the plant for the first time.

Topics: Asteraceae; Benzopyrans; Flavonoids; Kaempferols; Plants, Medicinal; Quercetin

Two kaempferol coumaroyl glycosides (i.e. platanoside and tiliroside) isolated from the methanolic extract of Platanus orientalis L. buds, were examined for their in vitro cytotoxic activity against a panel of human leukaemic cell lines. Platanoside (1) exhibited cytotoxic activity against most of the cell lines tested, while tiliroside (2) was active against two of the nine tested cell lines. Compound 1, was examined for its effect on the uptake of [(3)H]thymidine as a marker of DNA synthesis. Kaempferol was used as a control.

Topics: Antineoplastic Agents, Phytogenic; Benzopyrans; Cell Survival; DNA; Flavonoids; Glycosides; Humans; Kaempferols; Phenols; Quercetin; Tumor Cells, Cultured