Showing papers on "Acacetin published in 2009"

Correlation between antiangiogenic activity and antioxidant activity of various components from propolis.

Abstract: Propolis possesses various physiological activities. In this study, we examined the antiangiogenic and antioxidant activities of various components from propolis: acacetin, apigenin, artepillin C, caffeic acid phenethyl ester, chrysin, p-coumaric acid, galangin, kaempferol, pinocembrin, and quercetin. The effects of these components were tested on in vitro models of angiogenesis, tube formation and growth of human umbilical vein endothelial cells (HUVECs). Furthermore, these components were evaluated for their antioxidant activities by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical-scavenging and ferric reducing/antioxidant power (FRAP) assays. Two propolis components, caffeic acid phenethyl ester, and quercetin, possessed strong inhibitory effects on tube formation and on endothelial cell proliferation and, coincidentally, showed strong antioxidant activity. Artepillin C, galangin, and kaempferol also possessed strong antiangiogenic and antioxidant activities to a slightly less degree. In contrast, acacetin, apigenin, and pinocembrin possessed a considerable degree of antiangiogenic activities, although they showed very low antioxidant activities. From these results, we propose that components from propolis such as artepillin C, caffeic acid phenethyl ester, galangin, kaempferol, and quercetin might represent a new class of dietary-derived antioxidative compounds with antiangiogenic activities. These propolis components may have the potential to be developed into pharmaceutical drugs for the treatment of angiogenesis-dependent human diseases such as tumors.

Flavonoid-induced morphological modifications of endothelial cells through microtubule stabilization

Abstract: Flavonoids are common components of the human diet and appear to be of interest in cancer prevention or therapy, but their structure-activity relationships (SAR) remain poorly defined. In this study, were compared 24 flavonoids for their cytotoxicity on cancer cells (B16 and Lewis lung) and their morphological effect on endothelial cells (EC) that could predict antiangiogenic activity. Ten flavonoids presented inhibitory concentrations for 50% of cancer cells (IC50, 48 h) below 50 microM: rhamnetin, 3',4'-dihydroxyflavone, luteolin, 3-hydroxyflavone, acacetin, apigenin, quercetin, baicalein, fisetin, and galangin. Important SAR for cytotoxicity included the C2-C3 double bond and 3',4'-dihydroxylation. Concerning the morphological effects on EC, only fisetin, quercetin, kaempferol, apigenin, and morin could induce the formation of cell extensions and filopodias at noncytotoxic concentrations. The SAR for morphologic activity differed from cytotoxicity and involved hydroxylation at C-7 and C-4'. Fisetin, the most active agent, presented cell morphology that was distinct compared to colchicine, combretastatin A-4, docetaxel, and cytochalasin D. Resistance to cold depolymerization and a 2.4-fold increase in acetylated alpha-tubulin demonstrated that fisetin was a microtubule stabilizer. In conclusion, this study disclosed several SAR that could guide the choice or the rational synthesis of improved flavonoids for cancer prevention or therapy.

Identification of Major Flavonoids in Petals of Edible Chrysanthemum Flowers and Their Suppressive Effect on Carbon Tetrachloride-Induced Liver Injury in Mice

Abstract: Major flavonoids contained in petals of edible chrysanthemum flowers (Chrysanthemum×morifolium Ramat. forma esculentum Makino, c.v Kotobuki) were identified, and their chemical compounds in relation to their radical scavenging activities and preventive effects against liver injury were compared. Based on retention times and UV spectra, three peaks on the HPLC chromatogram of the polyphenol fraction of edible chrysanthemum flowers confirmed the presence of luteolin 7-O-glucoside, apigenin 7-O-glucoside, and luteolin. Spectroscopic analysis determined the chemical structure of the three newly isolated compounds to be luteolin 7-O-(6''-O-malonyl)-glucoside, apigenin 7-O-(6''-O-malonyl)-glucoside, and acacetin 7-O-(6''-O-malonyl)-glucoside. Increases in plasma aspartate aminotransferase and alanine aminotransferase activities in mice (induced with liver injury by injection of carbon tetrachloride) were strongly suppressed by oral administration of luteolin and luteolin 7-O-(6''-O-malonyl)-glucoside, which have stronger radical scavenging activity than other compounds. Thus, it is suggested that compounds with chemical structures such as luteolin and luteoin 7-O-glucoside, which have maolonic acid on its glucosyl moiety, appear to readily available for mitigation of liver injury.

The methoxylated flavones eupatorin and cirsiliol induce CYP1 enzyme expression in MCF7 cells.

Abstract: Flavonoids have often been associated with cancer prevention and activity of the human cytochrome P450 enzymes CYP1A1 and CYP1B1 with the occurrence of cancer. The flavones eupatorin (1) and cirsiliol (2) enhanced CYP1 enzyme activity in a concentration-dependent manner in MCF7 human breast adenocarcinoma cells. In the range of 0−2.5 μM, 2 caused a dose-dependent increase in CYP1B1 mRNA levels and an increase in CYP1A1 mRNA. Compound 1 caused an increase in CYP1A1 and CYP1B1 mRNA at higher doses (∼5 μM). Both CYP1B1 and CYP1A1 catalyzed the conversion of 2 into an as yet unidentified compound. Application of the CYP1 family inhibitor, acacetin, significantly increased the IC50 value of 2 in MCF7 cells, but did not significantly affect the action of 1. The data suggest that 2 induces CYP1 enzyme expression in cancer cells and is subsequently converted by CYP1B1 or CYP1A1 into an antiproliferative agent.

Antifeedant activities of secondary metabolites from Ajuga nipponensis against adult of striped flea beetles, Phyllotreta striolata

Abstract: Antifeedant activities of the isolated chemical compounds from Ajuga nipponensis, were studied against adult of striped leaf beetles. The methanol, petroleum ether, ethyl acetate and n-butanol extracts at 1.0 mg/ml, were used in this study. All four extracts exhibited more than 65 antifeedant index at 24 h and ethyl acetate extract showed significant activity against striped leaf beetles with 83.12 antifeedant index. Six compounds and one fraction were isolated by chromatography and their structures were identified by NMR, MS and FTIR spectra. At 2.0 mg/ml for 24 h the three compounds 20-hydroxyecdysone, acacetin and apigenin showed considerable activities with antifeedant indexes 59.29, 51.22 and 61.55, respectively. In contrast to this the antifeedant indexes of acacetin and apigenin, were sharply reduced as the time extended and that of 20-hydroxyecdysone remained unchanged. In addition, the synergistic effects of two mixtures of secondary metabolites, were studied and no sharp difference was observed.

Perturbation of the lipid phase of a membrane is not involved in the modulation of MRP1 transport activity by flavonoids

Abstract: The expression of transmembrane transporter multidrug resistance-associated protein 1 (MRP1) confers the multidrug-resistant phenotype (MDR) on cancer cells. Since the activity of the other MDR transporter, P-glycoprotein, is sensitive to membrane perturbation, we aimed to check whether the changes in lipid bilayer properties induced by flavones (apigenin, acacetin) and flavonols (morin, myricetin) were related to their MRP1 inhibitory activity. All the flavonoids inhibited the efflux of MRP1 fluorescent substrate from human erythrocytes and breast cancer cells. Morin was also found to stimulate the ATPase activity of erythrocyte ghosts. All flavonoids intercalated into phosphatidylcholine bilayers as judged by differential scanning calorimetry and fluorescence spectroscopy with the use of two carbocyanine dyes. The model of an intramembrane localization for flavones and flavonols was proposed. No clear relationship was found between the membrane-perturbing activity of flavonoids and their potency to inhibit MRP1. We concluded that mechanisms other than perturbation of the lipid phase of membranes were responsible for inhibition of MRP1 by the flavonoids.

Flavonoid Constituents and Antimicrobial Activity of Date (Phoenix dactylifera L.) Seeds Growing in Egypt

Abstract: The methanolic extract of date palm (Phoenix dactylifera L.) seeds cultivated in El-Dakhla Oases, Egypt, was investigated for their phenolics and antimicrobial activity. Seven flavonoids were isolated and identified as isoquercetrin (1), luteolin 7-O--D-neohesperopyranoside 3-O-methylether (2), luteolin 7-O--D-neohesperopyranoside (3), acacetin 7-O--D-neohesperopyranoside (4), apigenin 7-O�-D-apiofuranoside (5), apigenin 7- O-�-D-apiofuranosyl-(1 2)-O--D-glucopyranoside (6) and genistein 8-C--D-glucopyranoside (7). The structures were determined mainly by spectroscopic methods (UV, 1 H-, 13 C-NMR, 2D-NMR). Results of an antimicrobial test showed that the methanolic extract of the P. dactylifera seeds moderately inhibited the growth of Gram-positive and Gram-negative bacteria.

Chemical Constituents of Pedicularis cephalantha Franch and P. siphonantha Don

Abstract: Thirteen compounds were isolated from the whole plants of Pedicularis cephalantha,which were identified as(±)-pinoresinol(1),acacetin(2),luteolin(3),7-deoxygardoside(4),yuheinoside(5),euphroside(6),mussaenosidic acid(7),mussaenoside(8),aucubin(9),martynoside(10),isomartynoside(11),clerodenoside A(12)and kidjolanin(13).Four compounds were isolated from the whole plants of P.siphonantha,which were identified as(+)-dehydrovomifoliol(14),vomifoliol(15),ω-hydroxypropioguaiacone(16)and 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(17).

Chemical constituents from herb of Solanum lyratum

Abstract: Objective To study the chemical constituents of Solanum lyratum, And to explore the anti-tumor effect of some steroidal compounds from it. Method The chemical constituents were isolated and purified via silica gel and Sephadex LH-20 column chromatography as well as recrystallization. Their structures were determined on the basis of spectral analysis and physicochemical properties. 3 of the steroidal compounds were tested for their in vitro inhibitory activities in Hep G2 cells. Result Tweleve compounds were isolated and identified as diosgenin (1), tigogenin (2), tigogenone (3), diosgenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucuroniduronic acid methyl ester (4), 4-methyl-cholesta-7-ene-3beta-ol (5), acacetin 7-O-rutinoside (6), 1,5-dihydroxy-3-methoxy-7-methy-anthraquinone (7), 1,3,5-trihydroxy-7-methyl-anthracenedione (8), physcion-8-O-beta-D-glucopyranoside (9), soya-cerebroside I (10), isovanillin (11), docosylferulate (12). Compounds 2-4 had no significant inhibition on Hep G2 cells low concentration. With the increased of the concentration, the growth inhibiting effect against the cells increased, too. Conclusion Compounds 2, 3, 5-12 were isolated from the plant for the first time. Compounds 2-4 had growth inhibiting effect against the Hep G2 cells.

Chemical constituents of Chrysanthemum indicum L.

Abstract: ObjectiveTo investigate the chemical constituents of Chrysanthemum indicum LMethods: Isolated by column chromatography on silica gel and Sephadax LH-20,and purified by recrystallization Their structures were determined on the basis of the physicochemical properties and spectral dataResults:Thirteen compounds were isolated and identified as acacetin(1),tuteolin(2),apigenin (3),eupatilin(4),tricin(5),5,7,3',4'-Tetrahydroxy-6,5 '-dimethoxyflavone(6),apigenin7-O-β-D-glucopyranoside (7),luteolin-7-O-β-D-glucopyranoside(8),linarin(9),cumambrin-A (10),yejuhua lactone(11),7-(2-hydroxy-2-propyl)-10-methyl-4-methyleneperhydronaphthalene-3, 5,6-triol(12),β-daucosterol(13)Conclusion:Compound 4～7 were obtained from this plant for the first time,and compound 5,6 were obtained from genus chrysanthemum for the first time

Interaction of 5,7-dihydroxy-4'-methoxyflavone with a multisubunit protein, carmin: thermodynamics and kinetics of interaction.

Abstract: Acacetin (5,7-dihydroxy-4'-methoxy flavone) is a flavone intrinsically present in the seeds of Carthamus tinctorius. Carmin is a multimeric, high molecular weight protein from the seeds of Carthamus tinctorius. The association constant of interaction of acacetin and carmin is maximum at 37.2 degrees C with a value of (3.96 +/- 0.61) x 10(4) M-1 as measured by fluorescence quenching. Acacetin has at least two binding sites on carmin. The interaction follows pseudo-first-order kinetics with a reaction rate constant of 3.4 +/- 0.4 s-1. The titration calorimetric data suggest that binding sites for acacetin and its structural analogue, biochanin A, are conserved. The interaction does not affect the association-dissociation equilibrium of the protein. Also, the binding does not induce any significant conformational changes in the protein as monitored by circular dichroic spectra. Biochanin A (5, 7-dihydroxy-4'-methoxyisoflavone), a structural analogue, interacts with carmin with an association constant of (9.33 +/- 1.44) x 10(4) M-1 at 36.9 degrees C. This indicates that the stereochemistry of the ligand plays an important role in the binding process of flavone to protein. Interaction studies of chemically modified lysyl and tryptophanyl groups separately, and lysyl and tryptophanyl groups sequentially, in the protein carmin with the ligands reveal the involvement of tryptophanyl residues in the binding process and show that it is predominantly an entropically driven hydrophobic interaction.

Chemical constituents and bioactivities of Malabaila suaveolens

Abstract: Volatile oil components, fatty acids, β-amyrin, and sterols were identified in the n -hexane extract of Malabaila suaveolens Coss. fruits. Angelicin, 4,7,9-trimethyl psoralen, isopimpinellin and umbelliferone were isolated from the dichloromethane extract of the plant. 5-Hydroxy 7, 3`, 4`-trimethoxyflavone, apigenin and its 7-O0-β-D-glucopyranoside were isolated from the ethyl acetate extract. From the methanol extract, a new flavonoid, apigenin 7-O-(6``-O-p-hydroxybenzoyl)-β-D-glucopyranoside (1), along with vicenin 2, acacetin 7-O-rutinoside, and 6-hydroxyapigenin 7-O-β-D-glucopyranoside were isolated. Toxicity study of n-hexane, dichloromethane, ethyl acetate extract and methanolic extracts of the plant proved that it is relatively nontoxic. The tested extracts showed significant analgesic and anti-inflammatory effects as compared with control groups and reference drugs. Also, the tested extracts showed significant antioxidant activity as compared with reference.

Chemical constituents in the flowers of Chrysanthemum morifolium Ramat.

Abstract: Aim To study the chemical constituents in the flowers of Chrysanthemum morifolium Ramat'huaiju' cvnovMethods The compounds were separated and purified by column chromatography and their structures were established by spectroscopic methodsResults Ten flavonoids were isolated and identified as luteolin(1),apigenin(2),acacetin(3),diosmetin(4),diosmetin 7-O-β-D-glucoside(5),luteolin 7-O-β-D-glucoside(6),acacetin 7-O-β-D-glucoside(7),acacetin 7-O-(6″-O-acety1)-β-D-glucoside(8),linarin(9),apigenin 7-O-β-D-glucoside(10)Conclusion Compounds 1-10 were isolated for the first time from Chrysanthemum morifolium Ramat'huaiju' cvnov

Exudate flavonoids of some Juglandaceae.

Abstract: Six species of Juglandaceae have been checked for the occurrence of flavonoid aglycones on their leaf and fruit surfaces. Except for one, they exhibit flavonols, mostly methyl ethers of kaempferol and quercetin, including 6-O-substituted derivatives. Apigenin and acacetin are the only flavones found so far. Flavonoids accumulated on leaves are different from those excreted on green fruits. It has become evident that in future studies greater attention must be paid to the localization of flavonoid aglycones in different plant organs.

Studies on chemical constituents of Dendranthema indicum var. aromaticum

Abstract: Objective To study chemical constituents of Dendranthema indicum var. aromaticum. Methods The constituents were separated and purified by column chromatography with silica gel and Semi-preparative HPLC. Their structures were identified on the basis of physical-chemical properties and spectral data. Results Seven compounds were isolated and identified as acacetin, apignein, acacetin-7-O-beta-D-glucopy ranoside, apignein-7-O-beta-D-glucopy ranosids, luteolin, beta-sitosterol and daucosterol. Conclusion Apigenin, acacetin-7-O-beta-D-glucopy ranoside and apignein-7-O-beta-D-glucopy ranoside are obtained from the plant for the first time.

Composition for preventing and treating breast cancer comprising acacetin

Abstract: A composition for preventing and treating the breast cancer, which contains an acacetin as an active ingredient is provided to reduce Bcl-2 expression, increase Bax and Bcl-2 and induce the apoptosis of MCF-7 cell which is a breast cancer cell. A composition for preventing and treating breast cancer cell comprises 25-200 muM of acecatin (5,7-dihydroxy-4'-methoxylflavon). The acecatin induces the activation of caspase, loss of mitochondria membrane potential, oxygen free radical generation, and the activation of stress-activated protein kinase/c-Jun NH-4 terminal kinase 1/2(SAPK/JNK1/2). The composition is administered through oral, mucous membrane (nasal cavity, sublingual, vagina, or rectum), perenteral (hypodermic and vein), topical (eye), transdermal or transcutaneous. The composition is used in a form of tablet, caplet, capsule, cachets, lozenges, powder, suppository, aerosol, gel, suspension, or elixir.

Isolation and Identification of Fungicidal Components in Flower of Chrysanthemum indicum L.

Abstract: Fungicidal components in flower of C.indicum were isolated and identified using Valsa mali,Coniothyrium diplodiella and Pythium aphanidermatum as tracking pathogens.A fungicidal compound was obtained from ethyl acetate extract of ethanol concrete of C.indicum flower by column chromatography and thin layer chromatography.The active compound was identified as acacetin 7-rutinoside by mass spectrometry and nuclear magnetic resonance spectroscopy.EC50 of acacetin 7-rutinoside against V.mali was 0.069 mg/mL.

Flavonoid Distribution in Asplenioid Ferns

Abstract: In a survey of 15 r~esentatives of the Asplenioid ferns for the pinnae flavonoids, kaempferol was found in 80 %, quercetin 53% and proanthocyanidin 13% of the species studied. Kaempferol3 O-methyl ether was found in A. marinum only. Acacetin and genkwanin have been previously found in the fern, Notholaena bryopoda (Polypodiaceae), butfor the first time in A. normale. This is the second report ofthe occurrence ofthis type offlavone inferns. Hispidulin and pectolinangenin were detected inA. glaucophyllum in trace amounts due to the small sample and at a relatively low concentration. Scutellarein was detected inA. belangeri. To ourknowledge, this is thefirst report of the existence ofhispidulin, pectolinangenin and scutellrein in ferns.