Flavonoids are nearly ubiquitous in plants and are recognized as the pigments responsible for the colors of leaves, especially in autumn. They are rich in seeds, citrus fruits, olive oil, tea, and red wine. They are low molecular weight compounds composed of a three-ring structure with various substitutions. This basic structure is shared by tocopherols (vitamin E). Flavonoids can be subdivided according to the presence of an oxy group at position 4, a double bond between carbon atoms 2 and 3, or a hydroxyl group in position 3 of the C (middle) ring. These characteristics appear to also be required for best activity, especially antioxidant and antiproliferative, in the systems studied. The particular hydroxylation pattern of the B ring of the flavonoles increases their activities, especially in inhibition of mast cell secretion. Certain plants and spices containing flavonoids have been used for thousands of years in traditional Eastern medicine. In spite of the voluminous literature available, however, Western medicine has not yet used flavonoids therapeutically, even though their safety record is exceptional. Suggestions are made where such possibilities may be worth pursuing.

The Effects of Plant Flavonoids on Mammalian Cells:Implications for Inflammation, Heart Disease, and Cancer

Polyphenols constitute one of the most numerous and ubiquitous groups of plant metabolites and are an integral part of both human and animal diets. Ranging from simple phenolic molecules to highly polymerized compounds with molecular weights of greater than 30,000 Da, the occurrence of this complex group of substances in plant foods is extremely variable. Polyphenols traditionally have been considered antinutrients by animal nutritionists, because of the adverse effect of tannins, one type of polyphenol, on protein digestibility. However, recent interest in food phenolics has increased greatly, owing to their antioxidant capacity (free radical scavenging and metal chelating activities) and their possible beneficial implications in human health, such as in the treatment and prevention of cancer, cardiovascular disease, and other pathologies. Much of the literature refers to a single group of plant phenolics, the flavonoids. This review offers an overview of the nutritional effects of the main groups of polyphenolic compounds, including their metabolism, effects on nutrient bioavailability, and antioxidant activity, as well as a brief description of the chemistry of polyphenols and their occurrence in plant foods.

Polyphenols: Chemistry, Dietary Sources, Metabolism, and Nutritional Significance

The antioxidant activities and total phenolics of 28 plant products, including sunflower seeds, flaxseeds, wheat germ, buckwheat, and several fruits, vegetables, and medicinal plants were determined. The total phenolic content, determined according to the Folin−Ciocalteu method, varied from 169 to 10548 mg/100 g of dry product. Antioxidant activity of methanolic extract evaluated according to the β-carotene bleaching method expressed as AOX (Δ log A470/min), AA (percent inhibition relative to control), ORR (oxidation rate ratio), and AAC (antioxidant activity coefficient) ranged from 0.05, 53.7, 0.009, and 51.7 to 0.26, 99.1, 0.46, and 969.3, respectively. The correlation coefficient between total phenolics and antioxidative activities was statistically significant. Keywords: Antioxidant activity; phenolics; medicinal plants; oilseeds; buckwheat; vegetables; fruits; wheat products

Antioxidant Activity and Total Phenolics in Selected Fruits, Vegetables, and Grain Products

Flavonoids are a class of secondary plant phenolics with significant antioxidant and chelating properties. In the human diet, they are most concentrated in fruits, vegetables, wines, teas and cocoa. Their cardioprotective effects stem from the ability to inhibit lipid peroxidation, chelate redox-active metals, and attenuate other processes involving reactive oxygen species. Flavonoids occur in foods primarily as glycosides and polymers that are degraded to variable extents in the digestive tract. Although metabolism of these compounds remains elusive, enteric absorption occurs sufficiently to reduce plasma indices of oxidant status. The propensity of a flavonoid to inhibit free-radical mediated events is governed by its chemical structure. Since these compounds are based on the flavan nucleus, the number, positions, and types of substitutions influence radical scavenging and chelating activity. The diversity and multiple mechanisms of flavonoid action, together with the numerous methods of initiation, detection and measurement of oxidative processes in vitro and in vivo offer plausible explanations for existing discrepancies in structure-activity relationships. Despite some inconsistent lines of evidence, several structure-activity relationships are well established in vitro. Multiple hydroxyl groups confer upon the molecule substantial antioxidant, chelating and prooxidant activity. Methoxy groups introduce unfavorable steric effects and increase lipophilicity and membrane partitioning. A double bond and carbonyl function in the heterocycle or polymerization of the nuclear structure increases activity by affording a more stable flavonoid radical through conjugation and electron delocalization. Further investigation of the metabolism of these phytochemicals is justified to extend structure-activity relationships (SAR) to preventive and therapeutic nutritional strategies.

Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships.

There has been increasing interest in the research on flavonoids from plant sources because of their versatile health benefits reported in various epidemiological studies. Since flavonoids are directly associated with human dietary ingredients and health, there is need to evaluate structure and function relationship. The bioavailability, metabolism, and biological activity of flavonoids depend upon the configuration, total number of hydroxyl groups, and substitution of functional groups about their nuclear structure. Fruits and vegetables are the main dietary sources of flavonoids for humans, along with tea and wine. Most recent researches have focused on the health aspects of flavonoids for humans. Many flavonoids are shown to have antioxidative activity, free radical scavenging capacity, coronary heart disease prevention, hepatoprotective, anti-inflammatory, and anticancer activities, while some flavonoids exhibit potential antiviral activities. In plant systems, flavonoids help in combating oxidative stress and act as growth regulators. For pharmaceutical purposes cost-effective bulk production of different types of flavonoids has been made possible with the help of microbial biotechnology. This review highlights the structural features of flavonoids, their beneficial roles in human health, and significance in plants as well as their microbial production.

/pdf/chemistry-and-biological-activities-of-flavonoids-an-483pb5vgo0.pdf

Chemistry and Biological Activities of Flavonoids: An Overview

Flavonoids are a group of polyphenolic compounds, diverse in chemical structure and characteristics, found ubiquitously in plants. Therefore, flavonoids are part of the human diet. Over 4,000 different flavonoids have been identified within the major flavonoid classes which include flavonols, flavones, flavanones, catechins, anthocyanidins, isoflavones, dihydroflavonols, and chalcones. Flavonoids are absorbed from the gastrointestinal tracts of humans and animals and are excreted either unchanged or as flavonoid metabolites in the urine and feces. Flavonoids are potent antioxidants, free radical scavengers, and metal chelators and inhibit lipid peroxidation. The structural requirements for the antioxidant and free radical scavenging functions of flavonoids include a hydroxyl group in carbon position three, a double bond between carbon positions two and three, a carbonyl group in carbon position four, and polyhydroxylation of the A and B aromatic rings. Epidemiological studies show an inverse correlation between dietary flavonoid intake and mortality from coronary heart disease (CHD) which is explained in part by the inhibition of low density lipoprotein oxidation and reduced platelet aggregability. Dietary intake of flavonoids range between 23 mg/day estimated in The Netherlands and 170 mg/day estimated in the USA. Major dietary sources of flavonoids determined from studies and analyses conducted in The Netherlands include tea, onions, apples, and red wine. More research is needed for further elucidation of the mechanisms of flavonoid absorption, metabolism, biochemical action, and association with CHD.

Flavonoids—Chemistry, metabolism, cardioprotective effects, and dietary sources

Flavonoids and coronary heart disease: dietary perspectives

Flavonoids are potent inhibitors of the oxidative modification of low-density lipoprotein (LDL), and foods containing these compounds have been shown to be negatively associated with coronary heart disease (CHD). Flavonoids reduce the formation of free radicals and protect or regenerate other antioxidants; or alternatively, they chelate divalent metal ions. Isoflavones may act in a manner similar to estrogen in that they lower LDL and in this way confer protection against CHD. Less is known about other minor dietary constituents, such as boron, which is widespread in fruits and vegetables. Boron may have an impact on CHD by inducing small increases in the concentration of plasma estrogen.

N.C. Cook

Papers

Flavonoids—Chemistry, metabolism, cardioprotective effects, and dietary sources

Flavonoids and coronary heart disease: dietary perspectives

Minor Dietary Factors in Relation to Coronary Heart Disease Flavonoids, Isoflavones and Boron