Showing papers on "Acacetin published in 2011"

Acacetin inhibits the invasion and migration of human non-small cell lung cancer A549 cells by suppressing the p38α MAPK signaling pathway

Abstract: Lung cancer is one of the most common malignancies in the world and its metastasis is the major cause of death in cancer patients. Acacetin (5,7-dihydroxy-4′-methoxyflavone), a flavonoid compound, has anti-peroxidative and anti-inflammatory effects. The effect of acacetin on invasion and migration in human NSCLC A549 cells was investigated. First, the result demonstrated acacetin could exhibit an inhibitory effect on the abilities of the adhesion, morphology/actin cytoskeleton arrangement, invasion, and migration by cell–matrix adhesion assay, immunofluorescence assay, Boyden chamber assay, and wound-healing assay. Molecular data showed that the effect of acacetin in A549 cells might be mediated via sustained inactivation of the phosphorylation of mixed-lineage protein kinase 3 (MLK3), mitogen-activated protein kinase kinases 3/6 (MKK3/6), and p38α MAPK signal involved in the downregulation of the expressions of matrix metalloproteinase-2 (MMP-2), matrix metalloproteinase-9 (MMP-9), and urokinase-type plasminogen activator (u-PA). Next, acacetin significantly decreased in the phosphorylation and degradation of inhibitor of kappaBα (IκBα), and the nuclear levels of nuclear factor kappa B (NF-κB), c-Fos, and c-Jun. Also, the treatment with acacetin to A549 cells also leads to a concentration-dependent inhibition on the binding abilities of NF-κB and activator protein-1 (AP-1). Furthermore, the treatment of specific inhibitor for p38 MAPK (SB203580) to A549 cells could cause reduced activities of MMP-2/9 and u-PA. In addition, acacetin significantly decreased the levels of phospho-p38α MAPK, MMP-2/9, and u-PA in p38α-cDNA-transfected cells concomitantly with a marked reduction on cell invasion and migration. Our results revealed the anti-migration and anti-invasion effects of acacetin, which may act as a promising therapeutic agent for the treatment of lung cancer.

Phenolic compounds from Sidastrum micranthum (A. St.-Hil.) fryxell and evaluation of acacetin and 7,4'-Di-O-methylisoscutellarein as motulator of bacterial drug resistence

Abstract: From the aerial parts of Sidastrum micranthum (A. St.-Hil.) Fryxell (Malvaceae) were isolated m-methoxy-p-hydroxy-benzaldehyde, o-hydroxy-benzoic acid, acacetin, quercetin, 7,4′-Di-O-methylisoscutellarein, genkwanin and tiliroside. These compounds were identified by data analyses of spectroscopic methods. Although acacetin and 7,4′-Di-O-methylisoscutellarein did not display relevant antibacterial activity (MIC = 256 µg/mL), they modulated the activity of antibiotics, i.e. in combination with antibiotics at 64 µg/mL (¼ MIC), a two-fold reduction in the MIC was observed for norfloxacin and ethidium bromide; regarding tetracycline and erythromycin a two-fold reduction in the MIC was observed only with 7,4′-Di-O-methylisoscutellarein.

Acacetin induces apoptosis in human T cell leukemia Jurkat cells via activation of a caspase cascade.

Abstract: Flavonoids are naturally occurring antioxidants, with several flavonoids shown to have chemopreventive effects on cancer. We investigated the effects of the flavonoid acacetin on human T cell leukemia Jurkat cells. Acacetin inhibited the proliferation of Jurkat cells by inducing apoptosis in a concentration- and time-dependent manner. Acacetin-induced cell death was characterized by changes in nuclear and cell morphology. Treatment of Jurkat cells with acacetin also induced caspase-3, -8 and -9 activities in a time-dependent manner. Acacetin-induced apoptosis was blocked by a broad-spectrum caspase inhibitor, a caspase-3 inhibitor and a caspase-8 inhibitor, but not by a caspase-9 inhibitor. In addition, acacetin promoted the expression of FAF1, phosphor-FADD, Apaf-1 and cytochrome c. Acacetin-induced apoptosis was also accompanied by upregulation of Bax, and downregulation of Bcl-2. Taken together, these results suggest that acacetin may induce apoptosis in T cell leukemia cells, possibly by activating the Fas-mediated pathway. These findings may help in designing cancer therapeutic and chemopreventive agents.

Isolation and characterization of antimicrobial, anti-inflammatory and chemopreventive flavones from premna odorata blanco

Abstract: Premna odorata Blanco (Verbenaceae) is a native tree of the Philippines where its leaves are used traditionally for vaginal irrigation and tuberculosis. It is one of the seven components of a commercialized Philippine herbal preparation called “Pito-Pito”. Its medicinal uses, however, have not been scientifically validated. This tree is not commonly cultivated and thrive in the less accessible limestone forests of the Philippines. Solvent partitioning and fractionation of the ethanolic crude extract of the leaves isolated two yellow amorphous powders. The identities of these compounds were determined by LC/MS/MS and NMR spectroscopic analyses, and their spectra were compared with literature data. The isolates were flavone aglycones which were the widespread acacetin and the non-widespread diosmetin. These flavones were isolated from the P. odorata for the first time ever. They had been reported by earlier studies to exhibit medicinal properties as antimicrobial, anti-inflammatory and chemopreventive. Thus, the current study has provided a scientific evidence of the medicinal properties of the leaves of P. odorata that could become the popular basis for the plant’s sustainable use, conservation and cultivation. Key words: Premna odorata Blanco (Verbenaceae), “pito-pito”, “alagau”, antimicrobial, anti-inflammatory, chemopreventive, flavones, diosmetin, acacetin.

A new hepatoprotective flavone glycoside from the flowers of Onopordum alexandrinum growing in Egypt.

Abstract: A bioactivity-guided fractionation of the ethyl acetate fraction of the flowers of Onopordum alexandrinum L. (Asteraceae) yielded a new flavonoidal glycoside designated as acacetin-7-O-galacturonide (9), alongside with nine known flavonoids; 6-methoxy-apigenin (hispidulin) (1), acacetin (2), apigenin (3), luteolin (4), kaempferol (5), eriodictyol (6), apigenin- 7-O-glucoside (7), luteolin-7-O-glucoside (8), and kaempferol-3-O-rutinoside (10). The compounds were assayed for their hepatoprotective activity against CCl₄-induced hepatic cell damage in rats and free radical scavenging activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 4, 6, 9, and 10 have not been previously reported from flowers of O. alexandrinum L., and this is the first report of acacetin-7-O-galacturonide (9) in nature which has also shown significant hepatoprotective and free radical scavenging effects. The isolated compounds were identified using different spectroscopic methods (UV, ¹H NMR, ¹³C NMR, HMQC, HMBC, and COSY).

Phytochemical and biological investigations of atriplex semibacata r .br. growing in egypt

Abstract: The lipid content of Atriplex semibacata growing in Egypt was studied. The unsaponifiable fraction was identified by GLC. A series of hydrocarbons ranging from C 14 -C 28 in addition to cholesterol, stigmasterol and the triterpenoids α and β - amyrin were identified. GLC analysis of fatty alcohols fraction revealed the presence of six fatty alcohols in which dotriacontanol (C 32 H 66 O) was the major (14.68%). Six compounds (five coumarins and one phenolic acid) were isolated for the first time from A. semibacata. The coumarin constituents isolated from the chloroform and the ethyl acetate fractions of the aqueous alcoholic extract of A. semibacata were identified as scopoletin, umbelliferorne, coumarin, scopolin, 7-methoxy coumarin in addition to a phenolic acid P-coumaric acid. Also, the flavonoidal compounds isolated from the n -butanol fraction of the plant revealed the presence of kaempferol 3-O glucoside and acacetin. Their identity was proved by m.p., TLC, PC, UV and MS analysis. The alcohol extract showed significant antimicrobial activity against G-ve bacteria, moderate activity against G+ve bacteria. On the other hand, the pet. Ether extract showed marked activity against G+ve bacteria and fungi, also the G-ve bacteria was greatly inhibited by the chloroform extract. The different extracts of the plant exhibited no cytotoxic activity against Erlich-ascites carcinoma cells line at the tested concentrations, also showed a strong antioxidant activity using DPPH. Key words: Atriplex semibacata , unsaponifiable fraction, fatty alcohols, coumarins, flavonoids, antimicrobial, antifungal, antioxidant, antitumor. doi: 10.4314/ajtcam.v8i4.15

Phytochemical study on the constituents from Cirsium arvense

Abstract: Phytochemical investigation on the chloroform soluble fraction of Cirsium arvense resulted in the isolation of five compounds namely Ciryneol C, Scopoletin, Pectolinarigenin-7-O-glucopyranoside, Acacetin and 6, 7-Dimethoxycoumarin. Their structures have been elucidated by EIMS, HREIMS, 1H and 13C NMR spectroscopic methods. These compounds have been isolated for the first time from this plant. All the isolated compounds were tested for their antibacterial and antifungal activities

Flavonoids from Tanacetum vulgare flowers

Abstract: Flowers of tansy (Tanacetum vulgare L.) are used in various medicinal forms as antihelminthic and cholegogic agents [1–5]. The pharmacological properties of tansy flower preparations are due mainly to the essential oil (thujone and other terpenoids) and flavonoids. According to various literature sources [3–5], apigenin, acacetin, luteolin, cinaroside, eupatilin, jaceidin, and jaceoside are the main flavonoids in tansy flowers. However, reports in the domestic and foreign literature are somewhat contradictory. The goal of the present work was to study the flavonoid composition of tansy flowers growing in Samara Oblast (Russia). We studied tansy flowers collected near Nizhnee Sancheleevo village, Samara Oblast (July, 2008). Flowers (150 g) were extracted exhaustively with EtOH (70%) by combining maceration (24 h) with subsequent thermal extraction at 85–90°C. The aqueous alcohol extracts were evaporated in vacuo to a thick residue (~50 mL). The condensed extract was dried over L 40/100 silica gel. The resulting powder (extract + silica gel) was placed on a layer of silica gel that was formed in CHCl3 and eluted by CHCl3 and CHCl3:EtOH in various ratios (97:3, 95:5, 93:7, 90:10, 88:12, 85:15, 80:20, 70:30). The separation of the compounds was monitored by TLC on Silufol UV 254 and Sorbfil PTSKh-AF-A-UV plates using CHCl3:EtOH (4:1) and CHCl3:MeOH:H2O (26:14:3). Fractions containing the dominant compound 1 were combined. The precipitate that formed in these was separated and recrystallized from EtOH to afford 1 in 0.2% yield of the air-dried raw material mass. Fractions containing compounds 2–4 (each separately) were transferred to a chromatographic column (sorbent height 4.0 cm; diameter, 5 cm). The respective chromatographic column was eluted by H2O and aqueous EtOH (20%, 40, 70, and 96). Purification over polyamide columns afforded 2 (96% EtOH eluent), 3 (40% EtOH eluent), and 4 (70% EtOH eluent). The compounds were purified additionally by recrystallization from aqueous EtOH. The chemical structures of flavonoids 1–4 were elucidated using PMR and UV spectroscopy and mass spectrometry in addition to chemical transformations. Flavonoids 1 and 3 were cleaved by acid hydrolysis (10% HCl, 100°C, 2 h) and -glucosidase (Fluka, Hungary) into glucose and the aglycons, which were identified by TLC as acacetin (5,7-dihydroxy-4 methoxyflavone) (2) and apigenin (5,7,4 -trihydroxyflavone) (4), respectively. Flavonoids 2 and 4 were also isolated from tansy raw material in the free state. The PMR spectrum of 1 showed two 2H doublets at 8.07 and 7.14 ppm with SSCC (J) 9 Hz that were assigned to H-2 ,6 and H-3 ,5 , respectively; two 1H doublets at 6.84 and 6.45 ppm with J = 2.5 Hz that were characteristic of ring A protons (H-8 and H-6), and a singlet for H-3 at 6.95 (flavone compound). A 3H singlet at 3.87 for the C-4 OCH3 group and a singlet for the 5-OH of the flavonoid were observed in the PMR spectrum. The carbohydrate was placed on the 7-OH group on the basis of these results and those from enzymatic hydrolysis, and UV spectroscopy (lack of a bathochromic shift of the short-wavelength absorption band in the presence of NaOAc) [6]. The glucose was bonded as -D-glucopyranosyl (characteristic doublet for the anomeric proton at 5.35 ppm with J = 7.2 Hz). The chemical studies and spectra data suggested that 1 had the structure 5,7-dihydroxy-4 -methoxyflavone 7-O-Dglucopyranoside (tilianin) [7]. The chemical structure of 3 was studied analogously. Based on UV, NMR, and mass spectral data in addition to results from chemical transformations it was identified as 5,7,4 -trihydroxyflavone 7-O-D-glucopyranoside (cosmosiin).

Flavonoids and nor-sesquiterpenes of Pedicularis densispica

Abstract: OBJECTIVE To study the chemical constituents of the whole plants of Pedicularis densispica. METHOD The chemical constituents were isolated by various chromatographic methods and their structures were determined by chemical evidences and spectral data. RESULT Ten compounds were isolated and identified as acacetin (1), apigenin-7-0-beta-glucopyranoside (2), kaempferol-3,7-O-alpha-dirhamnopyranoside (3), scutellarein-7-0-beta-glucopyranoside (4), chrysoeriol-7-O-beta-glucopyranoside (5), pedicutricone A (6), dearabinosyl pneumonanthoside (7), salidroside (8), darendoside B (9), and maltol-beta-D-glucopyranoside (10). CONCLUSION These compounds were isolated from the titled plant for the first time. Except compounds 6 and 8, the others were obtained for the first time from the genus Pedicularis.

사자발쑥과 고려엉겅퀴 추출물의 항산화 및 간암세포 활성 효과

Abstract: In the present study, we investigated the compositions, antioxidant activities and anti-tumor effects of Artemisia princeps Pampanini (APD) as well as blanched leaves (CNBD) and dried leaves (CND) from Cirsium setidens Nakai on HepG2 cells. Water and ash contents were increased in CND. Protein and lipid contents were increased in CNBD. K, Ca, Mg, Fe and Cu contents of CND were higher than those of CNDB and APD. P contents was significantly decreased in CND. Yields of CND was reached high levels, but TPC, TFC, acacetin, apigenin, cynarin contents, and antioxidant activity were higher in APD. Viability of HepG2 liver cells was significantly decreased in APD. Therefore, extracts of APD are more effective preventing the liver cancer than extracts of CND and CNBD.

Flavonoids from Hemistepta lyrata

Abstract: Objective:To investigate the chemical constituents from the chloroform and ethyl acetate fractions of ethanol extract from Hemistepta lyrata.Method: The compounds were isolated by silica gel chromatography,ODS chromatography,Sephadex LH-20 chromatography,and preparative HPLC,and their structures were elucidated on the basis of chemical and spectroscopic methods,including MS,1D and 2D NMR spectral techniques.Result:Eight flavonoids were isolated from the chloroform and ethyl acetate fractions of ethanol extract from H.lyrata,and were identified as acacetin(1),cirsimaritin(2),apigenin(3),kaempferol(4),kaempferol-3-O-β-D-glucopyranoside(5),kaempferol-3-O-β-D-glucopyranoside(6),kaempferol-3-O-α-L-rhamnopyranosyl-(1 →6)-β-D-glucopyranoside(7),and acacetin-7-O-α-L-rhamnopyranosyl-(1 →6)-β-D-glucopyranoside(8).Conclusion: This is the first report of the isolation of 5 from Hemistepta genus.

Study on the flavanone constitutes of Buddleja davidii

Abstract: Objective To study the chemical constitutes of Buddleja davidii. Methods The constitutes were isolated and purified by silica gel column chromatography, polyamide column chromatography and macroporous absorption resin and their structures were elucidated by spectroscopic analysis. Results Seven compounds including Apigenin (1), Apigenin-7-O-beta-D-glucoside (2), Acacetin (3), Acacetin-7-O-beta-D-glucoside(4), Acacetin-7-O-alpha-L-rhamnopyranosyl-(1-6)-beta-D-glucopyranoside (5), Luteolin (6), Luteolin-7-O-beta-D-glueoside (7). Conclusion All these compounds are obtained from this plant for the first time.