cardamonin and alpinetin

Acrolein (ACR) is frequently produced by the thermal degradation of carbohydrates and amino acids and lipid peroxidation in the thermal processing of food. Long-term exposure to ACR can cause various chronic diseases. Here, we screened two high-temperature-resistant ACR inhibitors, cardamonin (CAR) and alpinetin (ALP), which can interconvert without any loss at 100 °C, and were obtained from

Topics: Acrolein; Alpinia; Chalcones; Flavanones; Meat; Spices

In the present study, we investigated the effects of Alpinia katsumadai H(AYATA) (Zingiberaceae) seed ethanolic extract (AKEE) and its three components on the production of inflammatory mediators and some potential underlying mechanisms in lipopolysaccharide (LPS)-induced inflammation RAW264.7 cells. The whole formula, AKEE, and three major component compounds were then evaluated for their effects on inflammation-related parameters using LPS-induced RAW264.7 cells. Production of namely nitric oxide (NO) and cytokine levels were measured by the Griess reagent and ELISA, respectively. To investigate the underlying mechanisms of anti-inflammatory activities of AKEE, protein expression of nitric oxide synthase (inducible nitric oxide synthase, iNOS), heme oxygenase-1 (HO-1), and nuclear factor-kappa B (NF-κB) were evaluated by western blot analysis. AKEE and the major group of compounds in AKEE (alpinetin, cardamonin, and pinocembrin) complement exert anti-inflammatory effects for NO and PGE(2) production. In addition, AKEE treatment significantly inhibited the LPS-induced production of interleukin-6 and tumor necrosis factor (TNF)-α, as well as the expression of iNOS. AKEE also induced HO-1 expression in RAW264.7 cells and inhibited the nuclear translocation of NF-κB by preventing degradation of the inhibitor kappa B-alpha. We also demonstrated that the effects of AKEE on TNF-α production were partially reversed by the HO-1 inhibitor tin protoporphyrin. These results indicate that AKEE and its major component may have anti-inflammatory activity via induction of HO-1 expression was partly responsible for the anti-inflammatory effects.

Topics: Alpinia; Animals; Anti-Inflammatory Agents, Non-Steroidal; Cell Line; Chalcones; Enzyme Induction; Flavanones; Heme Oxygenase-1; I-kappa B Proteins; Inflammation; Inflammation Mediators; Interleukin-6; Lipopolysaccharides; Macrophages; Metalloporphyrins; Mice; NF-kappa B; NF-KappaB Inhibitor alpha; Nitric Oxide; Nitric Oxide Synthase Type II; Plant Extracts; Prostaglandins; Protoporphyrins; Seeds; Tumor Necrosis Factor-alpha

This study aimed to find cytotoxic chemical constituents from Carya cathayensis leaves (LCC) by using various chromatographic procedures. Identification of the chemical constituents was carried out by various spectroscopic techniques and classical chemical methods. The cytotoxic activity of the constituents was assayed on HeLa and HepG2 cell lines by staining with 3-(4,5-dimethylthiahiazol-2-y1)-2,5-di-phenytetrazolium bromide (MTT). Six flavanoids, namely (1) pinostrobin, (2) pinostrobin chalcone, (3) wogonin, (4) cardamonin, (5) alpinetin and (6) tectochrysin were identified from this species. Compounds 2-6 were isolated from this kind of plant for the first time. MTT results showed that wogonin has a moderate cytotoxic activity with IC(50) values of 17.03 ± 2.41 and 44.23 ± 3.87 µM against HeLa and HepG2 cell lines, respectively. According to the correlation of primary the structure and activity, 8-methoxy substituent in these flavones may be a major factor of the antitumor activity.

Topics: Antineoplastic Agents, Phytogenic; Carya; Cell Proliferation; Chalcones; Flavanones; Flavonoids; HeLa Cells; Hep G2 Cells; Humans; Plant Leaves

To study the chemical constituents from the ethanolic extract of Alpinia katsumadai Hayata.. The compounds were separated with the column chromatographic, and their structures were identified by chemical and spectroscopic methods.. Eight compounds were isolated from the ethanol extract. On the basis of their physical and chemical properties and spectroscopic analysis, the structures of seven compounds were identified. They were 1,7-Diphenyl-5-hydroxy-4, 6-heptadien-3-one(I), 1,7-Diphenyl4, 6-heptadien-3-one(II), Pinocembrin (III), Cardamomin (IV), Alpinetin (V), 7,4'-Dihydroxy-5-methoxy flavanones(VI) and beta-Sitosterol(VIII), respectively.. Compounds I , II and VII are separated from this plant for the first time. Compounds I and II are also obtained from this genus of Alpinetin for the first time.

Topics: Chalcones; Flavanones; Plants, Medicinal; Seeds; Sitosterols; Spectrophotometry, Ultraviolet; Zingiberaceae

A novel electokinetic capillary chromatography method, reverse sodium dodecyl sulfate (SDS) micelles as pseudo-stationary phase, was developed for separation and detection of alpinetin and cardamonin. In this work, reverse micelles (RMs) have been firstly introduced into background electrolyte for electrophoresis separation. The optimum reverse SDS micelle system was formed with n-butyl chloride as continuous phase, SDS (20.9%, w/v) as the surfactant, W(0) (13.0, water-surfactant molar ratio), 18.0% (v/v) 1-butanol as the co-surfactant, 8.0% (v/v) acetonitrile (ACN), 1.5% (v/v) heptane, and a 60 mol L(-1) tris-(hydroxymethyl)aminomethane (Tris) buffer, as dispersed phase. Linear relationships (correlation coefficients: 0.9961 for cardamonin and 0.9991 for alpinetin) between the peak areas and concentration of the two compounds were obtained (5.0-350.0 microg mL(-1) for cardamonin and 1.25-350.0 microg mL(-1) for alpinetin). The detection limits (S/N=3) for cardamonin and alpinetin were 0.19 and 0.14 microg mL(-1), respectively. The method was successfully applied for the quantification of alpinetin and cardamonin in Alpinia katsumadai Hayata and kuaiwei tablet with satisfactory recoveries in the range of 95.9-100.2%.

Topics: Chalcones; Chromatography, Micellar Electrokinetic Capillary; Flavanones; Molecular Structure; Tablets; Time Factors

Studies on the binding affinity of protein to the active components of herbs are novel in biochemistry and are valuable for the information about speciation of drugs and exchange in biological systems. Alpinetin and cardamonin, two of the main constituents from the seeds of Alpinia katsumadai Hayata, have been used in traditional herbs as antibacterial, anti-inflammatory, and other important therapeutic activities of significant potency and low systemic toxicity. The interactions between two flavonoids analogs and lysozyme have been studied for the first time by spectroscopic method including Fourier transform infrared (FT-IR) spectroscopy, circular dichroism (CD) and UV-absorption spectroscopy in combination with Fluorescence quenching study. Both molecules showed high affinities to lysozyme under the experimental condition with drug concentrations from 3.33 x 10(-6) to 2.67 x 10(-5)molL(-1) for alpinetin and 1.67 x 10(-6) to 13.33 x 10(-6)molL(-1) for cardamonin. The alterations of protein secondary structure in the presence of drugs in aqueous solution were quantitatively estimated by the evidences from CD and FT-IR spectroscopy. The thermodynamic parameters obtained and the results of spectroscopic measurements suggest that hydrophobic and electrostatic interactions are the predominant intermolecular forces stabilizing two coordination compounds. The quenching mechanism and the number of binding site (n approximately 1) were obtained by fluorescence titration data. The efficiency of energy transfer provided the binding distances of 4.04 and 5.90 nm for alpinetin-LYSO and cardamonin-LYSO systems, respectively.

Topics: Alpinia; Binding Sites; Chalcones; Circular Dichroism; Flavanones; In Vitro Techniques; Kinetics; Muramidase; Protein Binding; Spectrometry, Fluorescence; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared; Thermodynamics

The vascular effects of cardamonin and alpinetin from Alpinia henryi K. Schum. were examined in the rat isolated mesenteric arteries. 1H and 13C nuclear magnetic resonance spectra showed that cardamonin is present in trans-form, and single-crystal radiographic structure revealed that alpinetin is present in S configuration. Both cardamonin and alpinetin produced a rightward shift in the concentration-response curve for phenylephrine in a noncompetitive manner, and they induced relaxation of phenylephrine-preconstricted arteries with respective mean inhibitory concentrations (IC50) of 9.3+/-0.6 microM and 27.5+/-2.8 microM. Both compounds also relaxed arteries preconstricted by endothelin I or U46619. Their relaxant effects were decreased in endothelium-removed rings. Pretreatment with N(G)-nitro-L-arginine methyl ester or methylene blue inhibited relaxation induced by both agents, and pretreatment with L-arginine reversed the effect of N(G)-nitro-L-arginine methyl ester on cardamonin-induced endothelium-dependent relaxation. The relaxant effects of cardamonin and alpinetin were unaffected by indomethacin (3 microM). Cardamonin and alpinetin inhibited 60 mM K+-induced contraction with respective IC50 of 11.5+/-0.3 microM and 37.9+/-3.6 microM. In addition, both agents inhibited the transient contraction induced by 3 microM phenylephrine or by 10 mM caffeine in Ca2+-free Krebs solution. Finally, these two agents also concentration dependently relax the arteries preconstricted by 1 microM phorbol 12,13-diacetate in Ca2+-free Krebs solution. These results indicate that purified cardamonin and alpinetin from A. henryi K. Schum. relaxed rat mesenteric arteries through multiple mechanisms. They induced both endothelium-dependent and -independent relaxation; the former is likely mediated by nitric oxide whereas the latter is probably mediated through nonselective inhibition of Ca2+ influx and intracellular Ca2+ release and inhibition of the protein kinase C-dependent contractile mechanism.

Topics: Animals; Chalcones; Dose-Response Relationship, Drug; Endothelium, Vascular; Flavanones; Flavonoids; Male; Mesenteric Arteries; Nitric Oxide; Phenylephrine; Plants, Medicinal; Rats; Rats, Sprague-Dawley; Seeds; Vasoconstriction; Vasoconstrictor Agents; Vasodilation; Vasodilator Agents