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Journal ArticleDOI

Flavonoids, a class of natural products of high pharmacological potency

B. Havsteen1
01 Apr 1983-Biochemical Pharmacology (Biochem Pharmacol)-Vol. 32, Iss: 7, pp 1141-1148
TL;DR: The few existing reports on the careful pharmacodynamic, pharmacokinetic and clinical studies which have been made have been summarized to provide a basis for a full-scale investigation of the therapeutic potential of flavonoids.
About: This article is published in Biochemical Pharmacology.The article was published on 1983-04-01. It has received 1605 citations till now.
Citations
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Journal Article
TL;DR: Western medicine has not yet used flavonoids therapeutically, even though their safety record is exceptional, and suggestions are made where such possibilities may be worth pursuing.
Abstract: 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.

4,663 citations


Additional excerpts

  • ...…antiallergic, hepatoprotective, antithrombotic, antiviral, and anticarcinogenic activities, discussed below separately (Gabor, 1979, 1986; Havsteen, 1984; Cody et al., 1986; Farkas et al., 1986; Selway, 1986; Cody et al., 1988; Welton et al., 1988; Das, 1989; Middleton and Kandaswami,…...

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Journal ArticleDOI
TL;DR: Several high-quality investigations have examined the relationship between flavonoid structure and antibacterial activity and these are in close agreement, and future studies may allow the development of a pharmacologically acceptable antimicrobial agent or class of agents.

3,630 citations


Cites background from "Flavonoids, a class of natural prod..."

  • ...For centuries, preparations that contain flavonoids as the principal physiologically active constituents have been used by physicians and lay healers in attempts to treat human diseases [10] ....

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  • ...The diverse range of cell functions affected by flavonoids in eukaryotic systems is well documented [10, 20] ....

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  • ...In the case of enzyme inhibition, this has been postulated to be due to the interaction of enzymes with different parts of the flavonoid molecule, e.g. carbohydrate, phenyl ring, phenol and benzopyrone ring [10] ....

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  • ...Flavonoids are ubiquitous in photosynthesising cells and therefore occur widely in the plant kingdom [10] ....

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  • ...[17, 18] , isoflavones [10] , chalcones [13, 19] , flavanones [10, 13] , flavones [10] , flavonols [10] , flavanon-3-ols [13] , anthocyanidins [13, 20] , flavan-3-ols [10, 13] , proanthocyanidins (occur as dimers, trimers, tetramers and pentamers; R = 0, 1, 2 or 3 flavan-3-ol structures) [13] , flavans [13] , flavan-3,4-diols [13] and dihydrochalcones [13] ....

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Journal ArticleDOI
TL;DR: Flavonoids are plant pigments that are synthesised from phenylalanine, generally display marvelous colors known from flower petals, mostly emit brilliant fluorescence when they are excited by UV light, and are ubiquitous to green plant cells.

2,424 citations


Cites background from "Flavonoids, a class of natural prod..."

  • ...Some biochemists from scientifically recognized laboratories felt compelled to text some of the seemingly exaggerated claims made by laymen and confirmed the existence of many interesting effects of the flavonoids (e.g., Havsteen, 1983)....

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Journal ArticleDOI
TL;DR: 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, carbonyl groups in carbon positions four, and polyhydroxylation of the A and B aromatic rings.
Abstract: 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.

2,201 citations

Book ChapterDOI
TL;DR: The radical chemistry of flavonoids not only is of interest from a kinetic or mechanistic point of view but also offers considerable insight into structural relationships of highly evolved plant components.
Abstract: Publisher Summary This chapter discusses the radical-scavenging efficiencies of flavonoids as antioxidants To test whether a certain substance acts as radical scavenger, the clearest evidence comes from the determination of reaction rate constants with a set of different specifically produced radicals In the tests discussed in the chapter, hydroxyl, azide, superoxide, linoleic acid peroxyl, tert-butoxyl, and sulfite radicals are used The spectral observation of radical reactions with flavonoids is assisted by the strong absorption characteristics of both the parent compounds and their respective aroxyl radicals Owing to the low solubility of flavonoids, conditions for pseudo-first order reactions with radical species can rarely be achieved for flavonoid aglycones Therefore, kinetic modeling calculations are employed The radical chemistry of flavonoids not only is of interest from a kinetic or mechanistic point of view but also offers considerable insight into structural relationships of highly evolved plant components First, the consistently high rate constants for attack by different types of radicals demonstrate the effective radicals scavenging capabilities of most flavonoids Second, owing to extensive electron delocalization as a prerequisite for radical stabilization, multiple mesomeric structures exist for aroxyl radical species of flavonoids

1,651 citations

References
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Journal ArticleDOI
23 Jun 1971-Nature
TL;DR: Experiments with guinea-pig lung suggest that some of the therapeutic effects of sodium salicylate and aspirin-like drugs are due to inhibition of the synthesis of prostaglandins.
Abstract: Experiments with guinea-pig lung suggest that some of the therapeutic effects of sodium salicylate and aspirin-like drugs are due to inhibition of the synthesis of prostaglandins.

8,204 citations

Book
01 Jan 1982
TL;DR: This book presents a more extensive, up-to-date and thorough guide to techniques used in flavonoid research, and discusses examples of a wide range of spectra, and features diagrams of flavonoids structures, reaction schemes and apparatus.
Abstract: As a follow-up to Dr Markham's highly successful publication, The Systematic Identification of Flavonoids (1970) co-authored with T.J. Mabry and M.B. Thomas, this book presents a more extensive, up-to-date and thorough guide to techniques used in flavonoid research. The techniques are discussed in the approximate order in which they are normally needed by the researcher and extensive cross-referencing is used throughout to guide the reader to the next recommended technique. Techniques covered include: chromatography, recrystallization, UV-visible spectroscopy, hydrolysis and product analysis, derivation degradation, H-NMR, C-NMR, and mass spectroscopy. The book, as a self-contained laboratory manual, contains extensive tabulations of reference data, discusses examples of a wide range of spectra, and features diagrams of flavonoid structures, reaction schemes and apparatus. Of special interest and importance to the beginner are the tables of trivial names, the list of sources of flavonoid standards and a discussion of the means for proving a new flavonoid identical to a known standard.

1,582 citations

Book ChapterDOI
TL;DR: A review of the chemistry, the fate of food flavonoids, and their nutritional effects can be found in this paper, where the authors discuss the antibiotic and/or bacteriostatic effects of foods rich in these compounds.
Abstract: A review of flavonoids discusses their chemistry, the fate of food flavonoids, (in the gastrointestinal tract) and their nutritional effects. These materials are comprised of flavanones, flavones, flavonols, flavandiols, catechins, and flavylium compounds. The antioxidant activity of food flavonoids is described and discussed, as well as their metal-chelating capacity and its effect on the activity of enzyme and membrane function. Vegetable foods rich in flavonoids are marked by an unusual stability of their Vitamin C content. The antibiotic and/or bacteriostatic effects of flavonoids are discussed, as well as their contribution to both the maintenance of body cell integrity and defense against malignant degeneration (via an anti-carcinogenic activity). (wz)

1,432 citations

Journal ArticleDOI
TL;DR: Two classes of common phenolic plant pigments contain many members mutagenic in the Salmonella/mammalian microsome assay, and the genetic toxicity of these agents and their dietary intake and metabolic fate in man is assessed.
Abstract: Two classes of common phenolic plant pigments, the anthraquinones and the flavonols, contain many members mutagenic in the Salmonella/mammalian microsome assay. Several reports on the mutagenicity or other genetic or “carcinogenic” effects of these compounds have appeared in the literature or have been presented at various scientific meetings. The object of this review paper is to assess the present state of knowledge with respect to the genetic toxicity of these agents and their dietary intake and metabolic fate in man. Such information is necessary for formulating an assessment of genetic or carcinogenic risk to man posed by these agents.

568 citations

Journal ArticleDOI
TL;DR: Although lens aldose reductase plays a central role in the etiology of sugar cataracts, the detailed properties of this enzyme have not previously been determined.

549 citations