Cyclooxygenase inhibitory and antioxidant compounds from the mycelia of the edible mushroom Grifola frondosa

The bioassay-guided isolation and purification of the hexane extract of the cultured mycelia of Grifola frondosa led to the characterization of a fatty acid fraction and three compounds, ergosterol (1), ergostra-4,6,8(14),22-tetraen-3-one (2), and 1-oleoyl-2-linoleoyl-3-palmitoylglycerol (3). The composition of fatty acid fraction was confirmed as palmitic, oleic, and linoleic acids by GC-MS and by comparison with the retention values of authentic samples. The structures of compounds 1-3 were established by spectroscopic methods. The fatty acid fraction and compounds 1-3 showed cyclooxygenase (COX) enzyme inhibitory and antioxidant activities. The inhibition of COX-1 enzyme by the fatty acid fraction and compounds 1-3 at 250 microg/mL were 98, 37, 55, and 67%, respectively. Similarly, COX-2 enzyme activity was reduced by fatty acid fraction and compounds 1-3 at 250 microg/mL by 99, 37, 70, and 4%, respectively. The inhibitions of liposome peroxidation by the fatty acid fraction and compounds 1 and 2 at 100 microg/mL were 79, 48, and 42%, respectively. This is the first report of compounds 2 and 3 from the cultured mycelia of G. frondosa. The COX inhibitory activities of compounds 1-3 are reported here for the first time.     

Characterization and antioxidant potential of Brazilian fruits from the Myrtaceae family

The objective of this study is to evaluating the Brazilian biodiversity through physicochemical characterization and determination of antioxidant potential of three species from the Myrtaceae family, namely yellow guava (Psidium cattleyanum Sabine), guabiroba (Campomanesia xanthocarpa O. Berg), and uvaia ( Eugenia pyriformis Cambess). Guabiroba had the greater quantity of phenolic compounds (9033 mg chlorogenic acid/100 g) and vitamin C (30.58 mg/g) and showed the best TSS/TTA (total soluble solid/total titratable acid) ratio (45.12). For the ABTS (2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic) method, the guabiroba (507.49 μM Trolox/g) presented the highest antioxidant potential; however, in the DPPH (2,2-diphenyl-1-picrylhydrazyl) method, uvaia (170.26 g/g DPPH) and guabiroba (161.29 g/g DPPH) were not statistically different. The uvaia outranked the other fruits with respect to its high carotenoid (909.33 μg/g) and vitamin A (37.83 μg/g) contents, and the yellow guava, although showing a lower bioactive compound content and antioxidant activity, nevertheless presented much higher values than many traditionally consumed fruits.     

Cellular antioxidant activity of common fruits

Measurement of antioxidant activity using biologically relevant assays is important in the screening of fruits for potential health benefits. The cellular antioxidant activity (CAA) assay quantifies antioxidant activity in cell culture and was developed to meet the need for a more biologically representative method than the popular chemistry antioxidant capacity measures. The objective of the study was to determine the cellular antioxidant activity, total phenolic contents, and oxygen radical absorbance capacity (ORAC) values of 25 fruits commonly consumed in the United States. Pomegranate and berries (wild blueberry, blackberry, raspberry, and blueberry) had the highest CAA values, whereas banana and melons had the lowest. Apples were found to be the largest contributors of fruit phenolics to the American diet, and apple and strawberries were the biggest suppliers of cellular antioxidant activity. Increasing fruit consumption is a logical strategy to increase antioxidant intake and decrease oxidative stress and may lead to reduced risk of cancer.     

Phenolic constituents and antioxidant capacity of four underutilized fruits from the Amazon region

The Amazon region comprises a plethora of fruit-bearing species of which a large number are still agriculturally unimportant. Because fruit consumption has been attributed to an enhanced physical well-being, interest in the knowledge of the chemical composition of underexplored exotic fruits has increased during recent years. This paper provides a comprehensive identification of the polyphenolic constituents of four underutilized fruits from the Amazon region by HPLC/DAD-ESI-MS(n). Arac?a? ( Psidium guineense ), jambola?o ( Syzygium cumini ), muruci ( Byrsonima crassifolia ), and cutite ( Pouteria macrophylla ) turned out to be primarily good sources of hydrolyzable tannins and/or flavonols. Additionally, different flavanonols and proanthocyanidins were identified in some fruits. The antioxidant capacity was determined by using the total oxidant scavenging capacity (TOSC) assay. Cutite showed the highest antioxidant capacity followed by jambola?o, arac?a?, and muruci.     

Spectroscopic identification and antioxidant activity of glucosylated carotenoid metabolites from Cydonia vulgaris fruits

Carotenoid metabolites are common plant constituents with significant importance for the flavor and aroma of fruits. Three new carotenoid derivatives, (2E,4E)-8-hydroxy-2,7-dimethyl-2,4-decadiene-1,10-dioic acid 1-O-beta-D-glucopyranosyl ester (1), (2Z,4E)-8-beta-D-glucopyranosyloxy-2,7-dimethyl-2,4-decadiene-1,10-dioic acid (3), and 3,9-dihydroxymegastigmast-5-ene-3-O-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (5), as well as three known compounds, have been isolated from the ethanolic extract of peels of Cydonia vulgaris, the fruit of a shrub belonging to the same family as the apple. All the compounds were identified by spectroscopic techniques, especially 1D and 2D NMR. Antioxidant activities of all the isolated metabolites were assessed by measuring their ability to scavenge DPPH radical and superoxide radical (O2*-) and to induce the reduction of Mo(VI).     

Lipoperoxidation and cyclooxygenases 1 and 2 inhibitory compounds from Iryanthera juruensis

Plants from Iryanthera genus have been traditionally used as food supplements by South American Indians. The MeOH extract of leaves of Iryanthera juruensis, one of the plants endemic to the Amazon region and consumed in Brazil, and the hexane extract from its seeds inhibited lipid peroxidation (LPO) and cyclooxygenase (COX-1 and -2)) enzymes in in vitro assays. Further analyses of these extracts yielded 5-deoxyflavones (1-5) from the leaf extract and sargachromenol (6), sargaquinoic acid (7), a novel juruenolic acid (8), omega-arylalkanoic acids (9a-c), and the lignan guaiacin (10) from the seed extract. Compounds 3-5 inhibited LPO by 86%, 77%, and 88% at 10 ppm, respectively, and compounds 6 and 9a-c showed inhibition at 76% and 78% at 100 ppm, respectively. However, compounds 7 and 8 were inactive and lignan 10 exhibited LPO inhibitory activity by 99% at 100 ppm compared to commercial antioxidants butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and vitamin E. The flavones 1-5 also inhibited COX-1 and -2 enzymes by 50-65% at 100 ppm. Compound 6 showed high but nonselective inhibition of COX-1 and COX-2 enzymes, when compared to aspirin and Celebrex, a nonsteroidal anti-inflammatory drug (NSAID). Compounds 7 and 10 inhibited COX-1 by 60% and 65% and COX-2 by 37% and 18%, respectively, whereas compounds 8 and 9a-c showed little or no activity against these enzymes.     

Free-radical-scavenging and antioxidant activities of secondary metabolites from reddened cv. Annurca apple fruits

Forty-three secondary metabolites were isolated and characterized from cv. Annurca apple fruit, an apple variety cultivated in the south of Italy. This apple cultivar undergoes a typical reddening treatment after collection. All of the compounds were characterized on the basis of their spectroscopic data. The compounds were tested for their radical-scavenging and antioxidant activities by measuring their capacity to scavenge DPPH* (2,2'-diphenyl-1-picrylhydrazyl radical), H2O2, and NO (nitric oxide) and to inhibit the formation of methyl linoleate conjugated diene hydroperoxides or TBARS (thiobarbituric acid reactive species).     

Subcritical water extraction of antioxidant compounds from rosemary plants

Subcritical water extraction at several temperatures ranging from 25 to 200 degrees C has been studied to selectively extract antioxidant compounds from rosemary leaves. An exhaustive characterization of the fractions obtained using subcritical water at different temperatures has been carried out by LC-MS, and the antioxidant activities of the extracts have been measured by a free radical method (DPPH). Results indicate high selectivity of the subcritical water toward the most active compounds of rosemary such as carnosol, rosmanol, carnosic acid, methyl carnosate, and some flavonoids such as cirsimaritin and genkwanin. The antioxidant activity of the fractions obtained by extraction at different water temperatures was very high, with values around 11.3 microg/mL, comparable to those achieved by SFE of rosemary leaves. A study of the effect of the temperature on the extraction efficiency of the most typical rosemary antioxidant compounds has been performed.     

Characterization of phenolic compounds in strawberry (Fragaria x ananassa) fruits by different HPLC detectors and contribution of individual compounds to total antioxidant capacity

Phenolic compounds in strawberry (Fragaria x ananassa) fruits were identified and characterized by using the complementary information from different high-performance liquid chromatography detectors: diode array, mass spectrometer in positive and negative mode, and coulometric array. Electrochemical profiles obtained from the coulometric array detector contributed to the structural elucidation suggested from the UV-vis and mass spectra. About 40 phenolic compounds including glycosides of quercetin, kaempferol, cyanidin, pelargonidin, and ellagic acid, together with flavanols, derivatives of p-coumaric acid, and ellagitannins, were described, providing a more complete identification of phenolic compounds in strawberry fruits. Quercetin-3-malonylhexoside and a deoxyhexoside of ellagic acid were reported for the first time. Antioxidative properties of individual components in strawberries were estimated by their electrochemical responses. Ascorbic acid was the single most important contributor to electrochemical response in strawberries (24%), whereas the ellagitannins and the anthocyanins were the groups of polyphenols with the highest contributions, 19 and 13% at 400 mV, respectively.     

Isolation and characterization of antioxidant compounds from Aspergillus candidus broth filtrate

The objectives of this study were to isolate the antioxidative components in the broth filtrate of Aspergillus candidus (CCRC 31543), to characterize their antioxidative properties, and to evaluate their safety. Three major compounds were isolated and identified as 3,3' '-dihydroxyterphenyllin, 3-hydroxyterphenyllin, and candidusin B. In the linoleic acid peroxidation system, the inhibition of peroxidation in these three compounds was greater than 95% and was significantly higher than that of alpha-tocopherol but equal to that of BHA at 12.5-200 microg/mL. As measured using the Rancimat method in lard, 3,3' '-di-OH-terphenyllin exhibited a protection factor value of 7.82, which was substantially higher than those of BHA (5.58) and alpha-tocopherol (4.29) at 200 microg/mL. 3,3' '-di-OH-terphenyllin and 3-OH-terphenyllin also exhibited marked scavenging effects on the alpha,alpha-diphenyl-beta-picrylhydrazyl radicals (94.7 and 96.0%, respectively), which were similar to those of BHA and alpha-tocopherol. Safety studies showed that these three compounds were neither cyto- nor geno-toxic toward human intestine 407 (INT 407) cells, nor mutagenic toward Salmonella typhimurium TA98 and TA100.     

Anti-inflammatory effects of phenolic compounds isolated from the fruits of Artocarpus heterophyllus

Artocarpus heterophyllus Lam is a large evergreen tree cultivated throughout Southeast Asia for its fruits. Its leaves and roots have been used for medicinal purposes. The aim of this work was to study the in vitro anti-inflammatory effects of phenolic compounds isolated from the ethyl acetate extracts of the fruits of Artocarpus heterophyllus. Three phenolic compounds were characterized as artocarpesin [5,7,2',4'-tetrahydroxy-6-(3-methylbut-3-enyl) flavone] ( 1), norartocarpetin (5,7,2',4'-tetrahydroxyflavone) ( 2), and oxyresveratrol [ trans-2,4,3',5'-tetrahydroxystilbene] ( 3) by spectroscopic methods and through comparison with data reported in the literatures. The anti-inflammatory effects of the isolated compounds ( 1- 3) were evaluated by determining their inhibitory effects on the production of proinflammatory mediators in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. These three compounds exhibited potent anti-inflammatory activity. The results indicated that artocarpesin ( 1) suppressed the LPS-induced production of nitric oxide (NO) and prostaglandin E 2 (PGE 2) through the down-regulation of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) protein expressions. Thus, artocarpesin ( 1) may provide a potential therapeutic approach for inflammation-associated disorders.     

Isolation of furocoumarins from bergamot fruits as HL-60 differentiation-inducing compounds.

The HL-60 differentiation-inducing compounds in bergamot fruits were isolated with column chromatography and identified as bergamottin, bergapten, and citropten by (1)H and (13)C NMR. Their HL-60 differentiation-inducing activity was measured by examining nitro blue tetrazolium (NBT) reducing, nonspecific acid esterase (NSE), specific esterase (SE), and phagocytic activities, and bergamottin showed the strongest activity among the coumarins isolated from bergamot fruits. The structure-activity relationship obtained from HL-60 differentiation assay suggests that hydrophobicity of furocoumarins is correlated with their activity.     

Phenol antioxidant quantity and quality in foods: fruits.

The free and bound phenols have been measured in 20 fruits commonly consumed in the American diet. Phenols were measured colorimetrically using the Folin-Ciocalteu reagent with catechin as the standard after correction for ascorbic acid contribution. On a fresh weight basis, cranberry had the highest total phenols, and was distantly followed by red grape. Free and total phenol quality in the fruits was analyzed by using the inhibition of lower density lipoprotein oxidation promoted by cupric ion. Ascorbate had only a minor contribution to the antioxidants in fruits with the exception of melon, nectarine, orange, white grape, and strawberry. The fruit extracts' antioxidant quality was better than the vitamin antioxidants and most pure phenols, suggesting synergism among the antioxidants in the mixture. Using our assay, fruits had significantly better quantity and quality of phenol antioxidants than vegetables. Fruits, specifically apples and cranberries, have phenol antioxidants that can enrich lower density lipoproteins and protect them from oxidation. The average per capita consumption of fruit phenols in the U.S. is estimated to be 255 mg/day of catechin equivalents.     

Nonenzymatic antioxidant activity of four organosulfur compounds derived from garlic

The nonenzymatic antioxidant activity of diallyl sulfide (DAS), diallyl disulfide (DADS), S-ethyl cysteine (SEC), and N-acetyl cysteine (NAC) in the liposome system was examined. The antioxidant protection from these organosulfur agents was concentration dependent (p < 0.05). SEC and NAC showed significantly lower lipophilicity and greater reducing power than DAS and DADS (p < 0.05). Greater antioxidant protection was presented in the combinations of alpha-tocopherol with four organosulfur agents than alpha-tocopherol treatment alone (p < 0.05), and SEC and NAC showed greater sparing effects on alpha-tocopherol (p < 0.05). Four organosulfur agents lost antioxidant activity when the temperature was 65 degrees C (p < 0.05). At pH 2.5 and 10, DAS and DADS still showed antioxidant activity (p < 0.05). On the basis of the observed nonenzymatic antioxidant protection, these organosulfur compounds are potent agents for enhancing lipid stability.     

Novel antioxidant compounds from the aqueous extract of the roots of Decalepis hamiltonii (Wight and Arn.) and their inhibitory effect on low-density lipoprotein oxidation

Roots of Decalepis hamiltonii are consumed as pickles and as a health drink in southern India for their health benefits. The antioxidant properties of the root extracts have been shown previously; this paper reports the isolation of antioxidant compounds from the aqueous extract of the roots of D. hamiltonii. Five novel antioxidant compounds were isolated and characterized by NMR and MS. The compounds exhibited free radical scavenging activity in vitro and inhibited low-density lipoprotein oxidation. This study demonstrates that the root extract of D. hamiltonii is a cocktail of several antioxidant compounds with health implications.     

Evolution of antioxidant capacity during storage of selected fruits and vegetables

Interest in the consumption of fresh fruits and vegetables is, to a large extent, due to its content of bioactive nutrients and their importance as dietary antioxidants. Among all of the selected fruits and vegetables, strawberries and black grapes have relatively high antioxidant capacities associated with high contents of total phenolic compounds, ascorbic acid, and flavonols. More interesting, the results of this study indicated that in most fruits and vegetables storage did not affect negatively the antioxidant capacity. Better, in some cases, an increase of the antioxidant capacity was observed in the days following their purchase, accompanied by an increase in phenolic compounds. In general, fruits and vegetables visually spoil before any significant antioxidant capacity loss occurs except in banana and broccoli. When ascorbic acid or flavonoids (aglycons of flavonols and anthocyanins) were concerned, the conclusions were similar. Their content was generally stable during storage.     

Controlled-atmosphere effects on postharvest quality and antioxidant activity of cranberry fruits

The effects of controlled-atmosphere (CA) storage on the firmness, respiration rate, quality, weight loss, total phenolics and flavonoids contents, and total antioxidant activities of the Pilgrim and Stevens cultivars of cranberries (Vaccinium macrocarpon Aiton) have been studied during storage in atmospheres of 2, 21, and 70% O(2) with 0, 15, and 30% CO(2) (balance N(2)); and 100% N(2) at 3 degrees C. Elevated CO(2) concentrations decreased bruising, physiological breakdown, and decay of berries, thereby reducing fruit losses. Respiration and weight loss of fruits decreased, but fruit softening increased, at higher CO(2) concentrations. Accumulations of acetaldehyde, ethanol, and ethyl acetate varied by cultivar and storage atmosphere but were generally highest in the 2 and 70% O(2) and 100% N(2) atmospheres and increased in response to elevated CO(2) concentrations. Overall, the 30% CO(2) plus 21% O(2) atmosphere appeared optimal for the storage of cranberries. Sensory analysis is required, however, to confirm that accumulations of fermentation products at this atmosphere are acceptable for consumers. Stevens fruits had a higher phenolics content and total antioxidant activity than Pilgrim fruits. The storage atmosphere did not affect the content of total phenolics or flavonoids. However, the total antioxidant activity of the fruits increased overall by about 45% in fruits stored in air. This increase was prevented by storage in 30% CO(2) plus 21% O(2).     

Bioactivity-guided fractionation for the butyrylcholinesterase inhibitory activity of furanocoumarins from Angelica archangelica L. roots and fruits

Isolation and identification of the inhibitors of butyrylcholinesterase (BChE), obtained from the extracts of roots and fruits of Angelica archangelica L., are reported. Our results confirmed the weak inhibitory effect of Angelica roots on acetylcholinesterase activity. BChE inhibition was much more pronounced at a concentration of 100 μg/mL for hexane extracts and attained a higher rate than 50%. The TLC bioautography guided fractionation and spectroscopic analysis led to the isolation and identification of imperatorin from the fruit's hexane extract and of heraclenol-2'-O-angelate from the root's hexane extract. Both compounds showed significant BChE inhibition activity with IC(50) = 14.4 ± 3.2 μM and IC(50) = 7.5 ± 1.8 μM, respectively. Only C8-substituted and C5-unsubstituted furanocoumarins were active, which could supply information about the initial structures of specific BChE inhibitors.     

Formation of Amadori compounds in dehydrated fruits.

The presence of Amadori compounds in commercial dehydrated fruits has been shown through HPLC analysis of the corresponding 2-furoylmethyl-amino acids obtained by acid hydrolysis. Furosine (2-furoylmethyl-lysine) was the main 2-furoylmethyl derivative observed in dried figs and apricot samples, whereas in prunes and dates similar amounts of furosine and 2-furoylmethyl-gamma-aminobutyric acid were detected. A considerable variation of 2-furoylmethyl-amino acid contents among commercial raisin samples was observed. 2-Furoylmethyl-gamma-aminobutyric acid and 2-furoylmethyl-arginine, the most abundant 2-furoylmethyl-amino acids, ranged between 9.9 and 75.8 mg/100 g sample and 10.0 and 62.5 mg/100 g sample, respectively. Most of the Amadori compounds present in raisins seem to have originated during the commercial shelf life period rather than during processing. Determination of 2-furoylmethyl-amino acids could be used as a method of controlling commercial dehydrated fruit and selecting storage conditions.