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Concept: Flavonoid

174

Studies have suggested the chemopreventive effects of flavonoids on carcinogenesis. Yet numbers of epidemiologic studies assessing dietary flavonoids and breast cancer risk have yielded inconsistent results. The association between flavonoids, flavonoid subclasses (flavonols, flavan-3-ols, etc.) and the risk of breast cancer lacks systematic analysis.

Concepts: Epidemiology, Cancer, Breast cancer, Metastasis, Nutrition, Chemotherapy, Flavonoid, Flavan-3-ol

169

BACKGROUND: The aim of this study was to screen various solvent extracts of whole plant of Torilis leptophylla to display potent antioxidant activity in vitro and in vivo, total phenolic and flavonoid contents in order to find possible sources for future novel antioxidants in food and pharmaceutical formulations. MATERIAL AND METHODS: A detailed study was performed on the antioxidant activity of the methanol extract of whole plant of Torilis leptophylla (TLM) and its derived fractions {n-hexane (TLH), chloroform (TLC) ethyl acetate (TLE) n-butanol (TLB) and residual aqueous fraction (TLA)} by in vitro chemical analyses and carbon tetrachloride (CCl4) induced hepatic injuries (lipid peroxidation and glutathione contents) in male Sprague-Dawley rat. The total yield, total phenolic (TPC) and total flavonoid contents (TFC) of all the fractions were also determined. TLM was also subjected to preliminary phytochemical screening test for various constituents. RESULTS: The total phenolic contents (TPC) (121.9+/-3.1 mg GAE/g extract) of TLM while total flavonoid contents (TFC) of TLE (60.9 +/-2.2 mg RTE/g extract) were found significantly higher as compared to other solvent fractions. Phytochemical screening of TLM revealed the presence of alkaloids, anthraquinones, cardiac glycosides, coumarins, flavonoids, saponins, phlobatannins, tannins and terpenoids. The EC50 values based on the DPPH (41.0+/-1 mug/ml), ABTS (10.0+/-0.9 mug/ml) and phosphomolybdate (10.7+/-2 mug/ml) for TLB, hydroxyl radicals (8.0+/-1 mug/ml) for TLC, superoxide radicals (57.0+/-0.3 mug/ml) for TLM and hydrogen peroxide radicals (68.0+/-2 mug/ml) for TLE were generally lower showing potential antioxidant properties. A significant but marginal positive correlation was found between TPC and EC50 values for DPPH, hydroxyl, phosphomolybdate and ABTS, whereas another weak and positive correlation was determined between TFC and EC50 values for superoxide anion and hydroxyl radicals. Results of in vivo experiment revealed that administration of CCl4 caused a significant increase in lipid peroxidation (TBARS) while decrease in GSH contents of liver. In contrast, TLM (200 mg/kg bw) and silymarin (50 mg/kg bw) co-treatment effectively prevented these alterations and maintained the antioxidant status. CONCLUSION: Data from present results revealed that Torilis leptophylla act as an antioxidant agent due to its free radical scavenging and cytoprotective activity.

Concepts: Oxygen, Antioxidant, Reactive oxygen species, Flavonoid, Chloroform, Methane, Hydroxyl radical, Lipid peroxidation

168

Electrical penetration graphs (DC EPG) were used to monitor the feeding behavior of the pea aphid, Acyrthosiphon pisum Harris (Hemiptera: Aphididae) exposed to the flavonoids luteolin and genistein in artificial diets. The EPG patterns generated by aphids feeding on plants were used to interpret the patterns generated on the artificial diets. Addition of flavonoids to the diets generally prolonged the period of stylet probing (as indicated by EPG pattern d-C), reduced salivation (as indicated by pattern d-E1) and passive ingestion (as indicated by pattern d-E2), and also delayed the onset of salivation and passive ingestion. At higher concentrations (≥100 μg cm(-3) for luteolin, ≥1,000 μg cm(-3) for genistein), the flavonoids completely stopped salivation and passive ingestion. In most events associated with active ingestion (EPG pattern d-G), however, differences in feeding behavior did not statistically differ between the control diet and those with flavonoids; luteolin, and genistein only at 10 μg cm(-3) prolonged the time until the first d-G pattern was observed. The current findings demonstrate detrimental effects of the isoflavone genistein and the flavone luteolin on the feeding behavior of the pea aphid, A. pisum. This can be employed to create plants which are resistant to aphids and other herbivores.

Concepts: Insect, Isoflavones, Flavonoid, Hemiptera, Flavones, Aphid, Sternorrhyncha, Aphididae

168

Lipophilic flavonoids found in the Lamiaceae exhibit unusual 6- and 8-hydroxylations whose enzymatic basis is unknown. We show that crude protein extracts from peltate trichomes of sweet basil (Ocimum basilicum L.) cultivars readily hydroxylate position 6 of 7-O-methylated apigenin, but not apigenin itself. The responsible protein was identified as a P450 monooxygenase from the CYP82 family, a family not previously reported to be involved in flavonoid metabolism. This enzyme prefers flavones but also accepts flavanones in vitro, and requires a 5-hydroxyl in addition to a 7-methoxyl residue on the substrate. A peppermint (Mentha x piperita) homolog displayed identical substrate requirements, suggesting that early 7-O-methylation of flavones might be common in the Lamiaceae. This hypothesis is further substantiated by the pioneering discovery of 2-oxoglutarate-dependent flavone demethylase activity in basil, which explains the accumulation of 7-O-demethylated flavone nevadensin.

Concepts: Protein, Metabolism, Enzyme, Flavonoid, Lamiaceae, Basil, Ocimum basilicum, Flavones

167

Flavonoids have known anti-inflammatory and antioxidative actions, and they have been described as neuroprotective and able to reduce damage in CNS diseases. We evaluated the action of the flavonoid rutin in an animal model of focal cortical ischemia induced by unilateral thermocoagulation of superficial blood vessels of motor (M1) and somatosensory (S1) primary cortices. Ischemic rats were submitted to daily injections (i.p.) for five days, starting immediately after induction of ischemia. We tested two doses: 50mg/kg or 100mg/kg of body weight. Sensorimotor tests were used to evaluate functional recovery. Bioavailability in plasma was done by chromatographic analysis. The effect of treatment in lesion volume and neurodegeneration was evaluated 48h and 72h after ischemia, respectively. We observed significant sensorimotor recovery induced by rutin, and the dose of 50mg/kg had more pronounced effect. Thus, this dose was used in further analyses. Plasma availability of rutin was detected from 2h to at least 8h after ischemia. The treatment did not result in reduction of lesion volume but reduced the number of degenerated neurons at the periphery of the lesion. The results suggest rutin as an efficient drug to treat brain ischemia since it was able to promote significant recovery of sensorimotor loss, which was correlated to the reduction of neurodegeneration in the periphery of cortical injury. Increasing studies with rutin and other flavonoids might give support for further clinical trials with these drugs.

Concepts: Blood vessel, Stroke, Traumatic brain injury, Cerebral cortex, Ischemia, Flavonoid, Brain ischemia, Rutin

166

Phytoestrogens constitute an attractive research topic due to their estrogenic profile and their biological involvement in woman’s health. Therefore, numerous studies are currently performed in natural products chemistry area aiming at the discovery of novel phytoestrogens. The main classes of phytoestrogens are flavonoids (flavonols, flavanones), isoflavonoids (isoflavones, coumestans), lignans, stilbenoids as well as miscellaneous chemical groups abundant in several edible and/or medicinal plants, belonging mostly to the Leguminosae family. As for other bioactives, the detection of new structures and more potent plant-derived phytoestrogens typically follows the general approaches currently available in the natural product discovery process. Plant-based approaches selected from traditional medicine knowledge and bioguided concepts are routinely employed. However, these approaches are associated with serious disadvantages such as time-consuming, repeated, and labor intensive processes as well as lack of specificity and reproducibility. In recent years, the natural products chemistry became more technology-driven, and several different strategies have been developed. Structure-oriented procedures and miniaturized approaches employing advanced hyphenated analytical platforms have recently emerged. They facilitate significantly not only the discovery of novel phytoestrogens but also the dereplication procedure leading to the anticipation of major drawbacks in natural products discovery. In this review, apart from the traditional concepts followed in phytochemistry for the discovery of novel biologically active compounds, recent applications in the field of extraction, analysis, fractionation, and identification of phytoestrogens will be discussed. Moreover, specific methodologies combining identification of actives and biological evaluation in parallel, such as liquid chromatography-biochemical detection, frontal affinity chromatography-mass spectrometry and pulsed ultrafiltration-MS will also be presented. Finally, miniaturized methods (microchip and biosensor) will be also discussed.With the current review, we attempt to give a wide and holistic overview of the different approaches which could be employed in the discovery of new phytoestrogens. On the other hand, we anticipate to attract more scientists to the area of phytoestrogens and to indicate the need of multidisciplinary concepts.

Concepts: Natural selection, Biology, Chemistry, Fabaceae, Flavonoid, Natural product, Natural products, Attractive

163

Flavonoids are a significant group of secondary metabolites in plants. Many of these compounds are potent antioxidants, being an important part in food products derived from the plants. The current status of research on flavonoid compounds in the fruit of Saskatoon berries (Amelanchier alnifolia Nutt.) and their health promoting effects, including recommended utilization, are reviewed. The major classes of flavonoids in the fruit are flavonols (quercetin and rutin), flavanes (proanthocyanidin compounds ranging from dimers through to heptamers and even higher polymers) and finally anthocyanins. The flavonoids represented the group of polyphenols that mostly contributed to the antioxidant activity of Saskatoon berries. High content of the flavoinoids antioxidants in the fruit is responsible for the observed anti-inflammatory, antidiadiabetic and chemo-protective effects.

Concepts: Nutrition, Antioxidant, Flavonoid, Resveratrol, Polyphenol, Flavonols, Rutin, Amelanchier alnifolia

86

Demand for organic foods is partially driven by consumers' perceptions that they are more nutritious. However, scientific opinion is divided on whether there are significant nutritional differences between organic and non-organic foods, and two recent reviews have concluded that there are no differences. In the present study, we carried out meta-analyses based on 343 peer-reviewed publications that indicate statistically significant and meaningful differences in composition between organic and non-organic crops/crop-based foods. Most importantly, the concentrations of a range of antioxidants such as polyphenolics were found to be substantially higher in organic crops/crop-based foods, with those of phenolic acids, flavanones, stilbenes, flavones, flavonols and anthocyanins being an estimated 19 (95 % CI 5, 33) %, 69 (95 % CI 13, 125) %, 28 (95 % CI 12, 44) %, 26 (95 % CI 3, 48) %, 50 (95 % CI 28, 72) % and 51 (95 % CI 17, 86) % higher, respectively. Many of these compounds have previously been linked to a reduced risk of chronic diseases, including CVD and neurodegenerative diseases and certain cancers, in dietary intervention and epidemiological studies. Additionally, the frequency of occurrence of pesticide residues was found to be four times higher in conventional crops, which also contained significantly higher concentrations of the toxic metal Cd. Significant differences were also detected for some other (e.g. minerals and vitamins) compounds. There is evidence that higher antioxidant concentrations and lower Cd concentrations are linked to specific agronomic practices (e.g. non-use of mineral N and P fertilisers, respectively) prescribed in organic farming systems. In conclusion, organic crops, on average, have higher concentrations of antioxidants, lower concentrations of Cd and a lower incidence of pesticide residues than the non-organic comparators across regions and production seasons.

Concepts: Epidemiology, Agriculture, Nutrition, Pesticide, Flavonoid, Organic farming, Organic food, Sustainable agriculture

38

The impact of different dietary flavonoid subclasses on risk of epithelial ovarian cancer is unclear, with limited previous studies that have focused on only a few compounds.

Concepts: Vitamin D, Metastasis, Nutrition, Hereditary nonpolyposis colorectal cancer, BRCA2, Ovarian cancer, Flavonoid

30

The 2015-2020 Dietary Guidelines for Americans advocate for increasing vegetable intake and replacing energy-dense foods with those that are nutrient-dense. Most Americans do not eat enough vegetables, and particularly legumes, each day, despite their well-established benefits for health. Traditional hummus is a nutrient-dense dip or spread made from cooked, mashed chickpeas, blended with tahini, olive oil, lemon juice, and spices. Consumers of chickpeas and/or hummus have been shown to have higher nutrient intakes of dietary fiber, polyunsaturated fatty acids, vitamin A, vitamin E, vitamin C, folate, magnesium, potassium, and iron as compared to non-consumers. Hummus consumers have also been shown to have higher Healthy Eating Index 2005 (HEI-2005) scores. This may be, in part, due to hummus' higher Naturally Nutrient Rich (NNR) score as compared to other dips and spreads. Emerging research suggests that chickpeas and hummus may play a beneficial role in weight management and glucose and insulin regulation, as well as have a positive impact on some markers of cardiovascular disease (CVD). Raw or cooked chickpeas and hummus also contain dietary bioactives such as phytic acid, sterols, tannins, carotenoids, and other polyphenols such as isoflavones, whose benefits may extend beyond basic nutrition requirements of humans. With chickpeas as its primary ingredient, hummus-and especially when paired with vegetables and/or whole grains-is a nutritious way for Americans to obtain their recommended servings of legumes. This manuscript reviews the nutritional value and health benefits of chickpeas and hummus and explores how these foods may help improve the nutrient profiles of meals.

Concepts: Health, Nutrition, Antioxidant, Fat, Vitamin, Flavonoid, Vegetable, Hummus