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Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease.

Seven structurally related flavonoids including luteolin, nobiletin, wogonin, baicalein, apigenin, myricetin and fisetin were used to study their biological activities on the human leukemia cell line, HL-60. On MTT assay, wogonin, baicalein, apigenin, myricetin and fisetin showed obvious cytotoxic effects on HL-60 cells, with wogonin and fisetin being the most-potent apoptotic inducers among them. The cytotoxic effects of wogonin and fisetin were accompanied by the dose- and time-dependent appearance of characteristics of apoptosis including DNA fragmentation, apoptotic bodies and the sub-G1 ratio. Treatment with an apoptosis-inducing concentration of wogonin or fisetin causes rapid and transient induction of caspase 3/CPP32 activity, but not caspase 1 activity. Further, cleavage of poly(ADP-ribose) polymerase (PARP) and decrease of pro-caspase 3 protein were detected in wogonin- and fisetin-treated HL-60 cells. An increase in the pro-apoptotic protein, bax, and a decrease in the anti-apoptotic protein, Mcl-1, were detected in fisetin- and wogonin-treated HL-60 cells. However, Bcl-2, Bcl-XL, and Bad all remained unchanged in wogonin- and fisetin-treated HL-60 cells. In vitro chromatin digestion revealed that endonuclease activity was profoundly enhanced in wogonin- and fisetin-treated HL-60 cells, and the addition of ethylenediaminetetraacetic acid (EDTA) or ethyleneglycoltetraacetic acid (EGTA) into the reaction blocked endonuclease activation and at an optimum pH of 7.5. The caspase 3 inhibitor, Ac-DEVD-CHO, but not the caspase 1 inhibitor, Ac-YVAD-CHO, attenuated wogonin- and fisetin-induced DNA ladders, PARP cleavage, and endonuclease activation. Pretreatment of HL-60 cells with N-acetyl-cysteine or catalase efficiently inhibited H(2)O(2) (200 microM)-induced apoptosis, but showed no inhibitory effect on wogonin- and fisetin-induced DNA ladders, caspase 3 activation, or bax protein induction. Decrease in endogenous ROS production was detected in wogonin- and fisetin-treated HL-60 cells by DCHF-DA assay. In conclusion, our experiments indicate that a decrease in intracellular peroxide level was involved in wogonin- and fisetin-induced apoptosis; activation of caspase 3 and endonuclease, induction of bax protein and suppression of Mcl-1 protein were detected in the process.

Acetylcysteine↗

Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structure-activity relationships.

Flavonoids affect the inflammatory process of the mammalian system and possess anti-inflammatory as well as immunomodulatory activities in vitro and in vivo. Since nitric oxide (NO) produced by inducible nitric oxide synthase (iNOS) is one of the inflammatory mediators, the effects of various naturally occurring flavonoids on NO production in LPS-activated RAW 264.7 cells were evaluated in vitro. Flavonoids such as apigenin, wogonin, luteolin, tectorigenin, and quercetin inhibited NO production, as measured by nitrite formation at 10-100 microM. The most active among 26 flavonoid derivatives tested were apigenin, wogonin, and luteolin, having IC50 values of 23, 17, and 27 microM, respectively, while AMT, a synthetic selective iNOS inhibitor, had an IC50 value of 0.09 microM. In contrast, flavanones, such as naringenin, and flavonoid glycosides, such as apiin, did not demonstrate significant inhibition up to 100 microM. These results clearly indicated that a C-2,3 double bond might be important, and that the potency of inhibition depended upon the substitution patterns of the flavonoid molecules. The inhibitory activity of flavonoids was not due to direct inhibition of iNOS enzyme activity because they did not reasonably inhibit iNOS activity, as measured by [3H]citrulline formation from [3H]arginine, up to 100 microM. In contrast, wogonin and luteolin concentration-dependently reduced iNOS enzyme expression, when measured by western blotting, at 10-100 microM. All these results clearly demonstrated that certain flavonoids inhibit NO production in lipopolysaccharide-activated RAW 264.7 cells, and their inhibitory activity might be due to reduction of iNOS enzyme expression.

Animals↗

Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley.

Flavone synthases (FNSs) catalyze the oxidation of flavanones to flavones, i.e. the formation of apigenin from (2S)-naringenin. While many plants express a microsomal-type FNS II, the soluble FNS I appears to be confined to a few species of the Apiaceae and was cloned recently from parsley plants. FNS I belongs to the Fe(II)/2-oxoglutarate-dependent dioxygenases characterized by short conserved sequence elements for cofactor binding, and its evolutionary context and mode of action are under investigation. Using a homology-based reverse transcription polymerase chain reaction approach, two additional flavonoid-specific dioxygenases were cloned from immature parsley leaflets, which were identified as flavanone 3beta-hydroxylase (FHT) and flavonol synthase (FLS) after expression in yeast cells. Sequence alignments revealed marginal differences among the parsley FNS I and FHT polypeptides of only 6%, while much less identity (about 29%) was observed with the parsley FLS. Analogous to FNS I, FLS oxidizes the flavonoid gamma-pyrone by introducing a C2, C3 double bond, and (2R,3S)-dihydrokaempferol (cis-dihydrokaempferol) was proposed recently as the most likely intermediate in both FNS I and FLS catalysis. Incubation of either FNS I or FLS with cis-dihydrokaempferol exclusively produced kaempferol and confirmed the assumption that flavonol formation occurs via hydroxylation at C3 followed by dehydratation. However, the lack of apigenin in these incubations ruled out cis-dihydrokaempferol as a free intermediate in FNS I catalysis. Furthermore, neither (+)-trans-dihydrokaempferol nor unnatural (-)-trans-dihydrokaempferol and 2-hydroxynaringenin served as a substrate for FNS I. Overall, the data suggest that FNS I has evolved uniquely in some Apiaceae as a paraphyletic gene from FHT, irrespective of the fact that FNS I and FLS catalyze equivalent desaturation reactions.

Amino Acid Sequence↗

Identification and determination of glucuronides and their aglycones in Erigeron breviscapus by liquid chromatography-tandem mass spectrometry.

A novel, speedy and reliable LC-MS-MS method for the search, identification and quantitation of O-glycosides and their aglycones from plant resources was established by analyzing the extract of Erigeron breviscapus. The extract was directly infused to a triple-quadrupole MS-MS and major glucuronides in the extract were screened out with high confidence by a neutral loss scan for the loss of a gluconic acid. The identity of these glucuronides and their aglycones was further confirmed with LC-MS-MS. In addition to scutellarin, apigenin 7-O-glucuronide, quercetin-3-O-glucuronide and their aglycones that were previously reported by others, we also confirmed by LC-MS-MS that remarkable amount of baicalin, an isomer of apigenin 7-O-glucuronide, presented in the extract of this plant, which had not been reported before. A satisfying quantitation of three glucuronides was also made by LC-MS-MS.

Asteraceae↗

Investigation of natural dyes occurring in historical Coptic textiles by high-performance liquid chromatography with UV-Vis and mass spectrometric detection.

Liquid chromatography (LC) combined with ultraviolet-visible (UV-Vis) and mass spectrometric (MS) detection was utilized to study the chemical components present in extracts of natural dyes originating from fiber samples obtained from Coptic textiles from Early Christian Art Collection of National Museum in Warsaw. Chromatographic retention, ionization, UV-Vis and mass spectra of twenty selected dye compounds of flavanoid-, anthraquinone- and indigo-types were studied. Most of the investigated compounds could be ionized by positive and negative ion electrospray ionization. Difficulties with the ionization by electrospray were experienced for indigotin and brominated indigotins, but these were ionized by atmospheric pressure chemical ionization. Mass spectrometric detection, utilizing different scanning modes of a triple quadrupole mass spectrometer, combined with the UV-Vis detection was demonstrated to be a powerful approach to detection and identification of dyes in the extracts of archeological textiles. Using this approach the following compounds were identified in the extracts of Coptic textiles: luteolin, apigenin, rhamnetin, kaempferol, alizarin, purpurin, xanthopurpurin, monochloroalizarin, indirubin, and so the type of dye that was utilized to dye the textiles could be identified. Detection capabilities for several dye-type analytes were compared for the UV-Vis and mass spectrometric detection. The signal-to-noise ratios obtained for luteolin, apigenin, and rhamnetin were higher for the MS detection for most of the examined sample extracts. Purpurin, alizarin, and indirubin showed similar signal-to-noise ratios for UV-Vis and mass spectrometric detection.

Art↗

Terpenoids from Salvia sclarea.

From an acetone extract of the whole plant Salvia sclarea, seven known diterpenes, sclareol, manool, salvipisone, ferruginol, microstegiol, candidissiol and 7-oxoroyleanone, and two new ones, 2,3-dehydrosalvipisone and 7-oxoferruginol-18-al, as well as two sesquiterpenes, caryophyllene oxide and spathulenol, alpha-amyrin, beta-sitosterol and the flavonoids apigenin, luteolin, 4'-methylapigenin, 6-hydroxyluteolin-6, 7,3',4'-tetramethyl ether, 6-hydroxy apigenin-7,4'-dimethyl ether were obtained. The diterpenoids and the sesquiterpenoids were tested for antimicrobial activity against standard bacterial strains and a yeast. 2,3-Dehydrosalvipisone, sclareol, manool, 7-oxoroyleanone, spathulenol and caryophyllene oxide were found to be active against Staphylococcus aureus, the first and third compound against Candida albicans and the last compound against Proteus mirabilis.

Anti-Infective Agents↗

Effects of seven pure flavonoids from mosses on germination and growth of Tortula muralis HEDW (Bryophyta) and Raphanus sativus L (Magnoliophyta).

Dried mosses (five moss species) were progressively extracted and subjected to a four-step Craig distribution. Seven pure flavonoids were isolated and identified. The flavonoids were the flavones apigenin, apigenin-7-O-triglycoside, lucenin-2, luteolin-7-O-neohesperidoside, saponarine and vitexin; and the biflavonoid bartramiaflavone and they were submitted to biological tests. The tests were performed in vitro on spore germination and protonemal growth of the moss Tortula muralis and on seed germination and root growth of Raphanus sativus. Flavonoids caused a decrease in the percentage of spore germination, protonemal development and root growth. In addition they caused morphological alterations, such as forked tips, swollen apices, rounded cells and early formation of brood cells in the protonemata. Data were discussed in relation to the presence of allelochemicals in mosses.

Brassica↗

Flavone C-glycosides from Lupinus hartwegii.

From the aerial parts of Lupinus hartwegii, two new flavone C-glycosides apigenin-7-O-beta-apiofuranosyl-6, 8-di-C-beta-glucopyranoside (1) and apigenin-7-O-beta-apiofuranosyl-6-C-beta-glucopyranosyl-8-C-(6z.qprime;-O-E-feruloyl)- beta-glucopyranoside (2) have been isolated together with two known isoflavonoid glucosides genistein-7-O-beta-glucopyranoside (3) and genistein-7, 4'-di-O-beta-glucopyranoside (4) as well as two known compounds ferulic acid 4-O-beta-glucopyranoside (5) and sparteine (6). The structures of the isolated compounds were verified by means of MS and NMR spectral analyses.

Carbohydrate Conformation↗

The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties.

The lipophilic flavonoids in leaf and flower of Tanacetum parthenium and T. vulgaris have been compared. While those of T. parthenium are methyl ethers of the flavonols 6-hydroxykaempferol and quercetagetin, the surface flavonoids of T. vulgare are methyl ethers of the flavones scutellarein and 6-hydroxyluteolin. Apigenin and two flavone glucuronides are surprisingly present in glandular trichomes on the lower epidermis of the ray florets of T. parthenium. The opportunity has been taken to revise the structures of the four 6-hydroxyflavonol methyl ethers of T. parthenium based on NMR measurements. These are now shown to be uniformly 6- rather than 7-O-methylated. Tanetin, previously thought to be a new structure, is now formulated as the known 6-hydroxykaempferol 3,6,4'-trimethyl ether. The vacuolar flavonoids of both plants are dominated by the presence of apigenin and luteolin 7-glucuronides; nine other glycosides were present, including the uncommon 6-hydroxyluteolin 7-glucoside in T. vulgare. When the major flavonol and flavone methyl ethers of the two plants were tested pharmacologically, they variously inhibited the major pathways of arachidonate metabolism in leukocytes. There were significant differences in potency, with the tansy 6-hydroxyflavones less active than the feverfew 6-hydroxyflavonols as inhibitors of cyclo-oxygenase and 5-lipoxygenase.

Animals↗

Antibacterial activity of pure flavonoids isolated from mosses.

Seven pure flavonoids were isolated and identified from five moss species. The flavonoids were the flavones apigenin, apigenin-7-O-triglycoside, lucenin-2, luteolin-7-O-neohesperidoside, saponarine and vitexin; and the biflavonoid bartramiaflavone. Some of these flavonoids were shown to have pronounced antibacterial effects against Enterobacter cloaceae, E. aerogenes and Pseudomonas aeruginosa (minimal bacteriostatic concentration MIC in the range of 4-2048 micrograms/ml). Because of their antibacterial spectrum mainly active against Gram negative bacterial strains, responsible for severe opportunistic infections and resistant to common antibacterial therapy, these flavonoids may be important tools in antibacterial strategies.

Anti-Bacterial Agents↗

Phytochemical and pharmacological studies on Sideritis taurica Stephan ex Wild.

Fatty acids (FA), hydrocarbons, alpha-amyrin, stigmasterol and beta-sitosterol were identified in the n-hexane extract of the aerial parts of Sideritis taurica Stephan ex Wild. Xanthotoxin, as well as 2-acetyl-3-hydroxy-5,6,8-trimethoxy-1,4-naphthoquinone were isolated from the methylene chloride extract of the plant. In addition to apigenin 7-O-beta-D-glucopyranoside and apigenin, previously reported from the plant, hypolaetin 7-O-beta-D-allopyranosyl-O-beta-D-glucopyranoside was isolated from the ethyl acetate extract. From the methanol extract, isoscutellarein 7-O-beta-D-allopyranosyl-O-beta-D-glucopyranoside was also isolated. Toxicity study of petroleum ether extract (f(1)), ethanolic extract (f(2)), dichloromethane fraction of f(2) (f(3)) and n-butanolic fraction of f(2) (f(4)) of the plant proved that it is relatively nontoxic. The tested extracts and fractions exhibited significant analgesic, anti-inflammatory, anti-ulcerogenic and antihyperglycaemic activities, but no anticonvulsant and antipyretic effects, as compared with control groups and reference drugs.

Animals↗

Analytical and preparative supercritical fluid extraction of chamomile flowers and its comparison with conventional methods.

Supercritical fluid extraction (SFE) was compared with Soxhlet extraction, steam distillation and maceration for the isolation of the active components present in chamomile flowerheads. The obtained fractions were analysed by GC-MS and reversed-phase HPLC. The yield of essential oil achieved by a 30-min extraction with pure CO2 at 90 atm and 40 degrees C was 4.4 times higher than that produced by steam distillation performed for 4 h. The recovery of the flavonoid apigenin obtained by supercritical CO2 after a 30-min extraction at 200 atm and 40 degrees C was 71.4% compared to Soxhlet extraction performed for 6 h and 124.6% compared to maceration performed for 3 days. However, the highly polar flavonoid apigenin-7-glucoside was not extracted by 100% CO2 (recovery values < 1.1%). Its extraction efficiency was markedly improved by the addition of the polar modifier methanol (5%, v/v) to the CO2 fluid, yet the obtained recoveries were unsatisfactory (14.6-19.5%). The SFE method was scaled-up for preparative applications using a pilot plant with three separation stages operating in series. Large-scale SFE was technically feasible with pure CO2 as the extracting fluid. However, the use of CO2 modified with organic solvents was not effective at the pilot-plant scale.

Chamomile↗

Anti- and pro-oxidative effects of flavonoids on metal-induced lipid hydroperoxide-dependent lipid peroxidation in cultured hepatocytes loaded with alpha-linolenic acid.

Lipid hydroperoxide (LOOH)-dependent lipid peroxidation was induced in alpha-linolenic acid (LNA)-loaded hepatocytes by adding Fe, Cu, V, or Cd ions at concentrations from 20 to 500 microM. The effects of structurally related flavonoids at concentrations from 10 to 500 microM on the lipid peroxidation were examined. The results with regard to each flavonoid subclass are as follows: (i) Flavonols such as myricetin, quercetin, fisetin, and kaempferol, but not morin, showed dose-dependent antioxidative activity against metal-induced lipid peroxidation at all metal concentrations. Myricetin, quercetin, and fisetin were the most effective antioxidants, although their efficacies depended on the metal ion. Kaempferol and morin had antioxidative activity equal to the other flavonols in the presence of Cu ions, but were much less effective for the other three metal ions. (ii) Flavones, luteolin, apigenin, and chrysin were antioxidative at low Fe concentrations, but were pro-oxidative at high Fe concentrations. Luteolin exhibited antioxidative activity similar to that of catechol-containing flavonols in the presence of the other three metal ions. Apigenin and chrysin also acted as pro-oxidants with V or with all metal ions, respectively. (iii) Taxifolin, a flavanone, also showed both anti- and prooxidative activity, depending on Fe concentrations, but with other metal showed only antioxidative activity ions. (iv) Epigallocatechin, a flavanol, was antioxidative with all metal ions, and its activity was similar to that of catechol-containing flavonols. The various effects of flavonoids on metal-induced lipid peroxidation in LNA-loaded hepatocytes is discussed with regard to the change in redox potential of flavonoid-metal complexes.

Animals↗

Effects of naturally-occurring flavonoids and biflavonoids on epidermal cyclooxygenase and lipoxygenase from guinea-pigs.

Although there have been numerous topical applications of plant extracts having flavonoids known as anti-inflammatory compounds, only a few studies were reported concerning effects of flavonoids on epidermal cyclooxygenase/lipoxygenase. In this investigation, effects of naturally occurring flavonoids on epidermal cyclooxygenase/lipoxygenase were studied using five selected derivatives: flavanone, apigenin (flavone), quercetin (flavonol), amentoflavone and ginkgetin (biflavone) because eicosanoids generated in the epidermis are believed to be involved in various biological activities of the skin. Microsomal and cytosolic fractions were obtained from guinea-pig epidermal homogenate by centrifugation and used as a source for cyclooxygenase and lipoxygenase. It was found that quercetin inhibited both cyclooxygenase and lipoxygenase, being more potent against lipoxygenase, while flavanone and apigenin did not show any inhibition. Amentoflavone, one of the biflavones tested, showed potent and selective inhibitory activity on cyclooxygenase (IC50 = 3 microM) which was comparable to indomethacin (IC50 = 1 microM). In contrast, structurally similar ginkgetin possessed weak inhibitory activity on cyclooxygenase. The in vivo effects of these flavonoids on the normal and diseased skin remain to be studied.

Animals↗

Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones.

Many plant compounds are able to modulate growth and reproduction of herbivores by directly interacting with steroid hormone systems. In insects, several classes of phytochemicals, including the phytoestrogens, interfere with molting and reproduction. We investigated whether the anti-ecdysone activity may be due to interaction with the ecdysone receptor (EcR) using a reporter-gene assay and a cell differentiation assay of an ecdysone-responsive cell line, Cl.8+. We tested rutin (delays molt in insects); four flavones: luteolin and quercetin (metabolites of rutin), and apigenin and chrysin; and three non-flavones, coumestrol and genistein (both estrogenic) and tomatine (alters molt in insects). None of the phytochemicals tested were ecdysone agonists in the reporter-gene assay, but the flavones were able to significantly inhibit EcR-dependent gene transcription. In the Cl.8+ cells, quercetin and coumestrol were mixed agonists/antagonists, while genistein, tomatine and apigenin showed a synergistic effect with ecdysteroid in the reduction of cell growth. We suggest that the rutin effects on molting in insects are most likely due to the metabolites, luteolin or quercetin, while tomatine acts via a non-EcR pathway. Flavones not only interact with EcR and estrogen receptor (ER), but also signal nitrogen-fixing bacteria to form root nodules. The NodD protein which regulates this symbiosis has two ligand-binding domains similar to human ERalpha. The evolutionary significance of these findings are discussed.

Animals↗

Antioxidant effect of phenolic compounds, alpha-tocopherol, and other minor components in virgin olive oil.

The effect of acidity, squalene, hydroxytyrosol, aldehydic form of oleuropein aglycon, hydroxytyrosyl acetate, tyrosol, homovanillic acid, luteolin, apigenin, alpha-tocopherol, and the mixtures hydroxytyrosol/hydroxytyrosyl acetate, hydroxytyrosol/tyrosol, and hydroxytyrosol/alpha-tocopherol on the oxidative stability of an olive oil matrix was evaluated. A purified olive oil was spiked with several concentrations of these compounds and, then, subjected to an accelerated oxidation in a Rancimat apparatus at 100 degrees C. Acidity, squalene, homovanillic acid, and apigenin showed negligible effect. At the same millimolar concentrations, the different o-diphenolic compounds yielded similar and significant increases of the induction time, alpha-tocopherol a lesser increase, and tyrosol a scarce one. At low concentrations of o-diphenols and alpha-tocopherol, a linear relationship between induction time and concentration was found, but at high concentrations the induction time tended toward constant values. To explain this behavior, a kinetic model was applied. The effect of the mixtures hydroxytyrosol/hydroxytyrosyl acetate was similar to that of a single o-diphenol at millimolar concentration equal to the sum of millimolar concentrations of both compounds. Concentrations of tyrosol >0.3 mmol/kg increase the induction time by 3 h. The mixtures hydroxytyrosol/alpha-tocopherol showed opposite effects depending on the relative concentrations of both antioxidants; so, at hydroxytyrosol concentrations <0.2 mmol/kg, the addition of alpha-tocopherol increased the induction time, whereas at higher hydroxytyrosol concentrations, the alpha-tocopherol diminished the stability.

Antioxidants↗

Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities.

A preliminary antimicrobial disk assay of chloroform, ethyl acetate, and n-butanol extracts of artichoke (Cynara scolymus L.) leaf extracts showed that the n-butanol fraction exhibited the most significant antimicrobial activities against seven bacteria species, four yeasts, and four molds. Eight phenolic compounds were isolated from the n-butanol soluble fraction of artichoke leaf extracts. On the basis of high-performance liquid chromatography/electrospray ionization mass spectrometry, tandem mass spectrometry, and nuclear magnetic resonance techniques, the structures of the isolated compounds were determined as the four caffeoylquinic acid derivatives, chlorogenic acid (1), cynarin (2), 3,5-di-O-caffeoylquinic acid (3), and 4,5-di-O-caffeoylquinic acid (4), and the four flavonoids, luteolin-7-rutinoside (5), cynaroside (6), apigenin-7-rutinoside (7), and apigenin-7-O-beta-D-glucopyranoside (8), respectively. The isolated compounds were examined for their antimicrobial activities on the above microorganisms, indicating that all eight phenolic compounds showed activity against most of the tested organisms. Among them, chlorogenic acid, cynarin, luteolin-7-rutinoside, and cynaroside exhibited a relatively higher activity than other compounds; in addition, they were more effective against fungi than bacteria. The minimum inhibitory concentrations of these compounds were between 50 and 200 microg/mL.

Anti-Bacterial Agents↗

Inhibition of malonaldehyde formation in oxidized calf thymus DNA with synthetic and natural antioxidants.

Calf thymus DNA was oxidized by Fenton's reagent with or without synthetic antioxidants (Trolox and DMPO) and natural antioxidants-quercetin, apigenin, 2''-O-glycosylisovitexin (2''-O-GIV), (+)-catechin, cyanidin, pelargonidin, keracyanin, and callistephin. Malonaldehyde (MA) formed in oxidized DNA was analyzed using gas chromatography. MA formed from oxidized DNA without antioxidants was 4.0 +/- 0.53 nmol/mg of DNA in buffer solution, 3.7 +/- 0.34 nmol/mg of DNA in NaOH solution, and 4.6 +/- 0.19 nmol/mg of DNA in HCl solution. MA formed from DNA with antioxidants (at the level of 0.1 micromol/mL) ranged from 1.90 +/- 0.18 (catechin) to 4.10 +/- 0.18 nmol/mg of DNA (cyanidin). Trolox and DMPO inhibited MA formation from DNA by 41.2% and 18.6%, respectively, at the level of 0.1 micromol/mL. Trolox (water-soluble vitamin E) exhibited dose-dependent inhibition. The decreasing order of inhibitory effect by flavonoids at the level of 0.1 micromol/mL was catechin (48.5%) > quercetin (47.1%) > 2''-O-GIV (40.5%) > apigenin (29.9%) and by the anthocyanins at the level of 0.1 micromol/mL was callistephin (45%) > keracyanin (33.2%) > pelargonidin (25.1%) > cyanidin (10.2%).

Animals↗