Biologically active carbazole alkaloids from Murraya koenigii

The bioassay guided fractionation of the acetone extract of the fresh leaves of Murraya koenigii resulted in the isolation of three bioactive carbazole alkaloids, mahanimbine (1), murrayanol (2), and mahanine (3), as confirmed from their (1)H and (13)C NMR spectral data. Compound 2 showed an IC(50) of 109 microg/mL against hPGHS-1 and an IC(50) of 218 microg/mL against hPGHS-2 in antiinflammatory assays, while compound 1 displayed antioxidant activity at 33.1 microg/mL. All three compounds were mosquitocidal and antimicrobial and exhibited topoisomerase I and II inhibition activities.     

Antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl

The antioxidant activity of phenolic compounds isolated from Mesona procumbens Hemsl. (Hsian-tsao) was investigated. Hsian-tsao was extracted with various solvents, and the results showed that the fraction treated with acidic ethyl acetate (pH 2) possessed large amounts of phenolic compounds and a strong antioxidant activity on peroxidation of linoleic acid. The antioxidant activity (inhibition of peroxidation, IP%) of the acidic ethyl acetate of Hsian-tsao extract at 50 microg/mL (98.9%) was stronger than those of 50 microg/mL alpha-tocopherol (78%) and BHA at 10 microg/mL (90%). When fractionated with Amberlite XAD-7 gel chromatography, the acidic ethyl acetate fraction of Hsian-tsao extract was separated into four subfractions (A-D). Subfraction B, with high yield and strong antioxidant activity, was further isolated and purified and then identified as containing protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, and syringic acid by means of UV, EI-MS, and (1)H and (13)C NMR. The antioxidant capability of isolated compounds was also determined using the thiocyanate system and the erythrocyte ghost system. The results indicate that the phenolic acids could be important antioxidant components in Hsian-tsao, among which caffeic acid with the highest antioxidant activity and the greatest content is most important.     

Effects of grape cell culture extracts on human topoisomerase II catalytic activity and characterization of active fractions

Grape and its cell culture extracts are rich in flavonoids and stilbenes that are biologically active. The objective of this study was to evaluate possible inhibitory effects of grape (a Vitis hybrid Bailey Alicant A) cell culture extract and subfractions on human DNA topoisomerase II catalytic activity and to characterize constituents in the most potent fractions. At 5 microg/mL, grape cell crude extract and Toyopearl (TP) fractions 2-6 provided significantly greater inhibition of topoisomerase II catalytic activity than quercetin, a chemopreventive agent previously known as a topoisomerase catalytic inhibitor. The most potent topoisomerase II catalytic inhibitors from grape cell culture extracts in descending order of potency were TP fractions 4 and 6 (IC(50) = 0.28-0.29 microg/mL), TP-3 (IC(50) = 0.74 microg/mL), and crude extract (IC(50) = 1.02 microg/mL); each was significantly more potent than resveratrol (IC(50) = 18.0 microg/mL), another well-known chemopreventive topoisomerase II catalytic inhibitor. Using both high-performance liquid chromatography and liquid chromatography electrospray ionization mass spectrometry, constituents in TP-4 and TP-6 were characterized. These constituents included cyanidin-3,5-diglucoside, malvidin-3-acetylglucoside, peonidin-3-coumaryl-5-diglucoside, procyanidin B(1), procyanidin B(2), procyanidin B(5), procyanidin dimer digallate, procyanidin C(1), myricetin, and rutin, none of which have been previously characterized from grape cell cultures. The significant potency especially of TP-4 and TP-6 from grape cell cultures suggests that these fractions may have potential as chemopreventive agents.     

Continuous hot pressurized solvent extraction of 1,1-diphenyl-2-picrylhydrazyl free radical scavenging compounds from Taiwan yams (Dioscorea alata)

This study investigates a semicontinuous hot pressurized fluid extraction process and the scavenging activity on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical of the extract from Taiwan yams (Dioscorea alata). Liquid-liquid extractions were preliminarily employed to generate six fractions, initially extracted by ethanol. Then, the aqueous solution of dried crude ethanol extract was sequentially fractionated by hexane, chloroform, ethyl acetate, and n-butanol. The EC50 value was defined as the UV absorption of DPPH concentrations sufficiently decreased to 50% of the original value. It was found that all peel portions have a better effect on scavenging of the DPPH free radical than meat portions, especially for the ethyl acetate partition of the peel portion of Tainung #2 yam. Its EC50 value (14.5 microg mL(-1)) was even lower than that of ascorbic acid (21.4 microg mL(-1)). Furthermore, semicontinuous hot pressurized ethanol was superior to hot pressurized water in extracting the compound scavenging the DPPH radical from the Purpurea-Roxb peel. The recovery of four unknown compounds corresponded to the scavenging ratio of DPPH free radical in the hot pressurized ethanol extract. Finally, three-level and four-factor experimental design revealed that ethanol ratio and temperature were the most effective factors in order. Conditions of 80% of aqueous ethanol, 20.0 kg/kg solid ratio, 180 psig (1.342 MPa), and 100 degrees C were preferred to extract those antioxidants from the yam peel.     

Evaluation of antioxidant activity and preventing DNA damage effect of pomegranate extracts by chemiluminescence method

The antioxidant activities of three parts (peel, juice, and seed) and extracts of three pomegranate varieties in China were investigated by using a chemiluminescence (CL) method in vitro. The scavenging ability of pomegranate extracts (PEs) on superoxide anion, hydroxide radical, and hydrogen peroxide was determined by the pyrogallol-luminol system, the CuSO4-Phen-Vc-H2O2 system, and the luminol-H2O2 system, respectively. DNA damage preventing the effect of PE was determined by the CuSO4-Phen-Vc-H2O2-DNA CL system. The results showed that the peel extract of red pomegranate had the best effect on the scavenging ability of superoxide anion because its IC50 value (4.01 +/- 0.09 microg/mL) was the lowest in all PEs. The seed extract of white pomegranate could scavenge hydroxide radical most effectively of the nine extracts (the IC50 value was 1.69 +/- 0.03 microg/mL). The peel extract of white pomegranate had the best scavenging ability on hydrogen peroxide, which had the lowest IC50 value (0.032 +/- 0.003 microg/mL) in the nine extracts. The seed extract of white pomegranate (the IC50 value was 3.67 +/- 0.03 microg/mL) was the most powerful on the DNA damage-preventing effect in all of the PEs. Also, the statistical analysis indicated that there were significant differences (at P < 0.05) among the extracts of the different varieties and parts in each system.     

Antioxidant capacity and cytotoxicity of essential oil and methanol extract of Aniba canelilla (H.B.K.) Mez

The leaves and fine stems, bark, and trunk wood oils of Aniba canelilla showed yields ranging from 0.2 to 1.3%. The main volatile constituent identified in the oils was 1-nitro -2-phenylethane (70.2-92.1%), as expected. The mean of DPPH radical scavenging activity (EC 50) of the oils (198.17 +/- 1.95 microg mL(-1)) was low in comparison with that of wood methanol extracts (4.41 +/- 0.12 microg mL(-1)), the value of which was equivalent to that of Trolox (4.67 +/- 0.35 microg mL(-1)), used as antioxidant standard. The mean amount of total phenolics (TP) (710.53 +/- 23.16 mg of GAE/g) and this value calculated as Trolox equivalent antioxidant capacity (TEAC) (899.50 +/- 6.50 mg of TE/g) of the wood methanol extracts confirmed the high antioxidant activity of the species. On the other hand, in the brine shrimp bioassay the values of lethal concentration (LC50) for the oils (21.61 +/- 1.21 microg mL(-1)) and 1-nitro-2-phenylethane (20.37 +/- 0.99 microg mL(-1)) were lower than that of the wood methanol extracts (91.38 +/- 7.20 microg mL(-1)), showing significant biological activities.     

Phenylpropanoid glycosides from Tynanthus panurensis: characterization and LC-MS quantitative analysis

A phytochemical analysis of the methanol extract of Tynanthus panurensis bark led to the isolation of one new phenylpropanoid glycoside, eugenol-O-[beta-D-xylopyranosyl-(1-->5)-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside], the known verbascoside, isoverbascoside, and leucosceptoside, along with the known flavonoid apigenin 8-C-[beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside], namely, katchimoside. Their structures were established by NMR and ESIMS experiments. Additionally, a quantitative study of the phenylpropanoid glycosides fraction of T. panurensis bark and of the hydroalcoholic extract prepared according to the traditional recipe was performed by combining high-performance liquid chromatography diode array detection with positive electrospray ionization tandem mass spectrometry. The new eugenol derivate was found to be the most abundant phenylpropanoid glycoside in both dried bark (19.5 mg/g) and hydroalcoholic extract (0.24 mg/mL). The antioxidant activity of all the isolated compounds and of the methanol and hydroalcoholic extract of the bark was determined by measuring the free radical scavenging effects using the Trolox equivalent antioxidant capacity method. The traditional hydroalcoholic extract showed a moderate activity.     

Antioxidative and antiplatelet effects of aqueous inflorescence Piper betle extract

Piper betle, belonging to the Piperaceae family, is a tropical plant, and its leaf and inflorescence are popularly consumed by betel quid (BQ) chewers in Taiwan and many other South and Southeast Asian countries. However, little is known about the biochemical properties of inflorescence Piper betle (IPB) toward reactive oxygen species (ROS) and platelet functions. In the present work, aqueous IPB extract was shown to be a scavenger of H(2)O(2), superoxide radical, and hydroxyl radical with a 50% inhibitory concentration (IC(50)) of about 80, 28, and 73 microg/mL, respectively. IPB extract also prevented the hydroxyl radical induced PUC18 plasmid DNA breaks at concentrations higher than 40 microg/mL. Since ROS are crucial for platelet aggregation, we further found that IPB extract also inhibited the arachidonic acid (AA) induced and collagen-induced platelet aggregation, with an IC(50) of 207 and 335 microg/mL, respectively. IPB extract also inhibited the AA-, collagen- (>100 microg/mL of IPB), and thrombin (>250 microg/mL of IPB)-induced thromboxane B(2) (TXB(2)) production by more than 90%. However, IPB extract showed little effect on thrombin-induced aggregation. These results indicated that aqueous components of IPB are potential ROS scavengers and may prevent the platelet aggregation possibly via scavenging ROS or inhibition of TXB(2) production.     

HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity

A hydroalcoholic extract of lime ( Citrus aurantifolia) leaves has been developed in Cuba to be used as a nutritional supplement and phytomedicine in the form of tincture (TLL). A HPLC-PDA-ESI/MS/MS method has been used for the comprehensive analysis of C-glycosyl flavones in TLL. Six C-glycosyl flavones were characterized and, to confirm the proposed structures and to elucidate the nature of the sugar units, a preparative procedure was applied, and isolated compounds were characterized by NMR. Apigenin-6,8-di-C-beta-D-glucopyranoside (vicenin II) (1), diosmetin-6,8-di- C-beta- d-glucopyranoside (2), apigenin-8-C-beta-D-glucopyranoside (vitexin) (3), apigenin-8-C-[alpha-L-arabinopyranosyl-(1-->6)]-O-beta-D-glucopyranoside (4), apigenin-6-C-[alpha-l-arabinopyranosyl-(1-->6)]-O-beta-D-glucopyranoside (5). and apigenin-6-C-beta-D-glucopyranoside (isovitexin) (6) were identified in TLL and quantified by HPLC-PDA. Compounds 4 and 5 were two new arabinosyl derivatives of vitexin and isovitexin. Inhibitor effect of TLL on platelet aggregation induced by physiological agonists of platelets was evaluated in human plasma. TLL inhibited significantly ADP and epinephrine-induced platelet aggregation in a concentration-dependent manner (IC 50=0.40 and 0.32 mg/mL, respectively).     

Assessment of the production of antioxidants from winemaking waste solids

Winemaking waste solids (WS, resulting from red grapes after fermentation and distillation to recover spirits) were subjected to various processing schemes for isolating fractions with antioxidant activity. The liquors entrapped in WS as received were separated by pressing and freeze-dried to yield a fraction with antioxidant activity (measured as DPPH radical scavenging capacity) comparable to those of synthetic antioxidants. A second approach based on the direct processing of raw WS in sulfuric acid medium under fixed operational conditions and further extraction of hydrolysis liquors with ethyl acetate enabled the isolation of a fraction with higher antioxidant ability at an improved yield. The most favorable approach started with a washing stage leading to liquors (which were directly freeze-dried to yield 1.20 g of extract/100 g of oven-dry WS and presented an EC50 of 0.41 g of extract/L) and washed solids, which were dried and subjected to hydrolytic processing (i) with water as a reactive in an autocatalyzed reaction (autohydrolysis) or (ii) with sulfuric acid solutions to give an ethyl acetate-soluble fraction with improved antioxidant properties (EC50 in the range of 0.18-0.40 g/L). Samples from washing liquors and processing of washed solids in aqueous medium were subjected to chromatographic fractionation and analysis to give isolates with remarkable antioxidant activity (with EC50 as low as 0.07 g/L) and to identify their major components.     

Isolation and identification of sea buckthorn (Hippophae rhamnoides) phenolics with antioxidant activity and α-glucosidase inhibitory effect

This study was performed to evaluate the antioxidant and α-glucosidase inhibitory effects from the extract, fractions, and isolated compounds of sea buckthorn leaves. Six compounds, kaempferol-3-O-β-D-(6'-O-coumaryl) glycoside, 1-feruloyl-β-D-glucopyranoside, isorhamnetin-3-O-glucoside, quercetin 3-O-β-D-glucopyranoside, quercetin 3-O-β-D-glucopyranosyl-7-O-α-L-rhamnopyranoside, and isorhamnetin-3-O-rutinoside, were isolated from sea buckthorn leaf extracts. The butanol fraction (EC(50) = 1.81 μg/mL) along with quercetin 3-O-β-D-glucopyranoside (EC(50) = 1.86 μg/mL) had a higher DPPH radical-scavenging activity and showed stronger reducing power (OD(700) = 1.83 and 1.78, respectively). The butanol fraction (477 mg GAE/g) contained the highest amount of phenolic compounds and also the most powerful α-glucosidase inhibitory effect (86%) at 5 μg/mL. The results indicate that sea buckthorn leaf extracts could potentially be used for food additives and the development of useful natural compounds.     

Antioxidant activity of a flavonoid-rich extract of Hypericum perforatum L. in vitro

A flavonoid-rich extract of Hypericum perforatum L. (FEHP) was prepared by adsorption on macroporous resin and desorption by ethanol. Total flavonoid content of FEHP was determined by a colorimetric method. The major constituents of FEHP, including rutin, hyperoside, isoquercitrin, avicularin, quercitrin, and quercetin, were determined by HPLC analysis and confirmed by LC-MS. Different antioxidant assays were utilized to evaluate free radical scavenging activity and antioxidant activity of FEHP. FEHP was an effective scavenger in quenching DPPH and superoxide radical with IC50 of 10.63 microg/mL and 54.3 microg/mL, respectively. A linear correlation between concentration of FEHP and reducing power was observed with a coefficient of r2 = 0.9991. Addition of 150 microg of FEHP obviously decreased the peroxidation of linoleic acid during 84 h incubation, but the amount of FEHP over 150 microg did not show statistically significant inhibitory effect of peroxidation of linoliec acid (p > 0.05). FEHP exhibited inhibitory effect of peroxidation of liposome induced both by hydroxyl radical generated with iron-ascorbic acid system and peroxyl radical and showed prominent inhibitory effect of deoxyribose degradation in a concentration-dependent manner in site-specific assay but poor effect in non-site-specific assay, which suggested that chelation of metal ion was the main antioxidant action. According to the results obtained in the present study, the antioxidant mechanism of FEHP might be attributed to its free radical scavenging activity, metal-chelation activity, and reactive oxygen quenching activity.     

Potential food additives from Carex distachya roots: identification and in vitro antioxidant properties

In the present study, the chemical composition and antioxidant properties of root methanol extract of Carex distachya Desf. (Cyperaceae) were assessed to use this plant as sources of food additives and nutraceuticals. The IC50 of the extract (4.2 microg/mL), derived from the DPPH radical scavenging capacity assay, was similar to those of ascorbic acid, alpha-tocopherol, and BHT. These results revealed a strong antioxidant activity because of the presence of an extraordinary quantity of bioactive phytochemicals. The phytochemical study of the root extract led to the isolation and identification of new and known polyphenols, most of them common constituents of plant foods. A total of 16 polyphenols, identified on the basis of spectroscopic data as 7 lignans, 4 phenylethanoids, 3 resveratrol derivatives, a monolignol, and a secoiridoid glucoside, were isolated. The tentative structural elucidation of the new metabolites 5'-O-beta-D-glucopyranosyloxy-3,3'-dimethoxy-7,9'-epoxylignan-4,8',9-triol and 3,5-bis-O-beta-D-glucopyranosyloxy-3'-methoxy-trans-stilben-4'-ol have been performed by a combined approach using ESI/TQ/MS techniques and 1D and 2D NMR experiments. All of the compounds have been tested for their antioxidant activity using six different antioxidant and radical scavenging tests. Interestingly, the extract contained high quantities of polyphenols, most of them reported as constituents of edible plants, such as grape and olive, suggesting that the methanol root extract of this plant could be used as a source of natural antioxidants useful as potential food additives.     

Chemical composition of volatile extract and biological activities of volatile and less-volatile extracts of juniper berry (Juniperus drupacea L.) fruit

Volatile chemicals in a dichloromethane extract from a steam distillate of juniper berry fruit (Juniperus drupacea L.) and its two column chromatographic fractions (eluted with hexane and ethyl ether) were analyzed by gas chromatography/mass spectrometry. The major compounds in the dichloromethane extract were alpha-pinene (23.73%), thymol methyl ether (17.32%), and camphor (10.12%). A fraction eluted with hexane contained alpha-pinene (44.24%) as the major constituent. A fraction eluted with ethyl ether had thymol methyl ether (22.27%) and camphor (19.65%) as the main components. Three samples prepared from the distillate and two additional samples prepared by petroleum ether and ethanol extraction directly from juniper berry fruits exhibited clear antioxidant activities with dose response in both 1,2-diphenyl picrylhydrazyl and beta-carotene assays. All samples except the hexane fraction showed comparable activities to that of the synthetic antioxidant t-butyl hydroquinone at a level of 200 microg/mL in the two testing systems. The extracts of dichloromethane, petroleum ether, and ethanol exhibited appreciable antimicrobial activities against six microorganisms with minimum inhibitory concentrations ranging from 0.5 mg/mL (volatile extract against Candida albicans ) to 1.2 mg/mL (ethanol extract against Aspergillus niger ). The results of the present study suggest that this fruit could be a natural antioxidant supplement for foods and beverages.     

Polyphenolic antioxidants from the fruits of Chrysophyllum cainito L. (Star Apple)

Chrysophyllum cainito L. (Sapotaceae), known commonly as star apple or caimito, is a tropical tree that bears edible fruits. The fruits are grown commercially in certain tropical and subtropical areas, such as southern Florida. In this study, the fresh fruits were extracted with methanol and partitioned with hexane and ethyl acetate sequentially. The ethyl acetate soluble fraction displayed high antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay (IC50 = 22 microg/mL). Activity-guided fractionation of the ethyl acetate soluble fraction was performed to identify the antioxidant constituents. Nine known polyphenolic antioxidants, (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3), (-)-epigallocatechin (4), quercetin (5), quercitrin (6), isoquercitrin (7), myricitrin (8), and gallic acid, have been identified from the fruits. Of these nine antioxidants, 2 is present in the highest concentration in star apple fruits (7.3 mg/kg fresh weight), and 5 showed the highest antioxidant activity (IC50 = 40 microM) in the DPPH assay.     

Topoisomerase I and II enzyme inhibitory aqueous extract of Ardisia compressa and ardisin protect against benomyl oxidation of hepatocytes

Tea preparations of Ardisia compressa (AC) have been used in folk medicine against liver disorders. The objective of this study was to evaluate the in vitro topoisomerase I and II enzyme inhibition and the antioxidant effect of an aqueous extract from dry leaves of AC and a pure component (ardisin) purified from AC on benomyl (Be)-induced cytotoxicity in primary culture rat hepatocytes. Lipid peroxidation (malondialdehyde), antioxidant enzyme activities of glutathione reductase, glutathione peroxidase, and superoxide dismutase, and glutathione levels were studied. Topoisomerase I and II enzyme inhibition was used to guide purification of ardisin, which was purified using TLC, MPLC, and preparative and analytical HPLC methods. Benomyl increased malondialdehyde (58% change in comparison to the control) and glutathione peroxidase (10%), producing a significant consumption of endogenous antioxidant glutathione (65%, P < 0.05). A 94% hepatocyte protection was observed when cells were first exposed to ardisin (0.27 microg/mL), followed by Be (35 microg/mL). Cell protection by the tea extract of AC (AE) was greater than that by (-)-epigallocatechin 3-gallate (EGCG). Ardisin showed a clear inhibition of topoisomerases I and II catalytic activity in Saccharomyces cerevisiae mutant cells JN 394, JN394t(-)(1), and JN394t-(2)(-)(5). The potency of ardisin was superior to that of AE and EGCG as an antioxidant, protecting rat hepatocytes when exposed to Be. On the basis of the effective concentrations of equivalents to [+]catechin found in the present study, it can be estimated that, in order to gain antioxidative protection, a person would need to ingest approximately 1 L of AC tea per day, with a total content of 10.8 g of plant material.     

Procyanidins as antioxidants and tumor cell growth modulators

Five procyanidin fractions with different structural complexities were obtained after fractionation of a grape seed extract. The procyanidin fraction's abilities to inhibit lipid peroxidation induced by 2,2'-azobis-2-methyl-propanimidamide dihydrochloride in a liposomal membrane system were examined. The antioxidant capacities of all fractions were evaluated through monitoring oxygen consumption and by measuring the formation of conjugated dienes. All tested fractions provided protection of membranes against peroxyl radicals by increasing the induction time of oxidation. This effect increased up to fraction II but decreased with the increase of the structural complexity of further procyanidin fractions, possibly due to steric hindrance effects exhibited by the more complex fractions. In addition, the antiradical properties and the reducing power of these fractions were determined by using 2,2-diphenyl-1-picrylhydrazyl and ferric reducing/antioxidant power methods, respectively. Moreover, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium-bromide reduction and DNA synthesis were measured in Michigan Cancer Foundation 7 (MCF-7), a human breast cancer cell line, treated with catechin or procyanidin fractions in order to evaluate the effect of these compounds on cell viability and proliferation. The results obtained showed that at 30 microg/mL, fractions I and II decreased cell viability and proliferation, which was not observed with 60 microg/mL of the same fractions. Catechin was also able to decrease cell viability and proliferation at 30 and 60 microg/mL. It is interesting to notice that the procyanidin fractions that exhibited higher antioxidant activity were the same to affect cell viability and proliferation.     

Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC)

Volatiles were isolated from the dried inner bark of Tabebuia impetiginosa using steam distillation under reduced pressure followed by continuous liquid-liquid extraction. The extract was analyzed by gas chromatography and gas chromatography-mass spectrometry. The major volatile constituents of T. impetiginosa were 4-methoxybenzaldehyde (52.84 microg/g), 4-methoxyphenol (38.91 microg/g), 5-allyl-1,2,3-trimethoxybenzene (elemicin; 34.15 microg/g), 1-methoxy-4-(1E)-1-propenylbenzene (trans-anethole; 33.75 microg/g), and 4-methoxybenzyl alcohol (30.29 microg/g). The antioxidant activity of the volatiles was evaluated using two different assays. The extract exhibited a potent inhibitory effect on the formation of conjugated diene hydroperoxides (from methyl linoleate) at a concentration of 1000 microg/mL. The extract also inhibited the oxidation of hexanal for 40 days at a level of 5 microg/mL. The antioxidative activity of T. impetiginosa volatiles was comparable with that of the well-known antioxidants, alpha-tocopherol, and butylated hydroxytoluene.     

Effects of some benzoxazinoids on in vitro growth of Cephalosporium gramineum and other fungi pathogenic to cereals and on Cephalosporium stripe of winter wheat

The benzoxazolinones benzoxazolin-2(3H)-one (BOA) and 6-methoxybenzoxazolin-2(3H)-one (MBOA) and selected degradation products of these compounds were examined for their in vitro antifungal activity against Cephalosporium gramineum, Gaeumannomyces graminis var. graminis, and Fusarium culmorum. BOA was also applied to the soil-incorporated inoculum of C. gramineum to test its capability of reducing Cephalosporium stripe disease in winter wheat. MBOA reduced the mycelial growth of G. graminis var. tritici, C. gramineum, and F. culmorum by 50% (EC50) at the concentrations of 77, 134, and 271 microg/mL of corn meal agar, respectively, and the corresponding BOA EC50 values for the fungi were 11, 189, and 456 microg/mL. BOA degradation products 2-amino-3H-phenoxazin-3-one (APO), 2-acetylamino-3H-phenoxazin-3-one (AAPO), and o-aminophenol (o-AP) were much more inhibitory to the growth of C. gramineum and G. graminis var. tritici than the parent compounds. APO, AAPO, and o-AP EC50 values were found to be as low as 0.58, 4.57, and 1.4 microg/mL, respectively, for C. gramineum and 0.78, 2.18, and 0.80 microg/mL for G. graminis var. tritici. These compounds applied at the corresponding concentrations did not significantly affect the mycelial growth of F. culmorum. The treatment of C. gramineum inoculum with a 1% water solution of BOA resulted in a significant reduction infection of winter wheat with C. gramineum as compared to the control with the untreated inoculum,but this treatment was not as effective as the application of a commercial fungicide.