Structure-antioxidant activity relationships of flavonoids and phenolic acids

The use of and search for drugs and dietary supplements derived from plants have accelerated in recent years. Ethnopharmacologists, botanists, microbiologists, and natural-products chemists are combing the Earth for phytochemicals and “leads” which could be developed for treatment of infectious diseases. While 25 to 50% of current pharmaceuticals are derived from plants, none are used as antimicrobials. Traditional healers have long used plants to prevent or cure infectious conditions; Western medicine is trying to duplicate their successes. Plants are rich in a wide variety of secondary metabolites, such as tannins, terpenoids, alkaloids, and flavonoids, which have been found in vitro to have antimicrobial properties. This review attempts to summarize the current status of botanical screening efforts, as well as in vivo studies of their effectiveness and toxicity. The structure and antimicrobial properties of phytochemicals are also addressed. Since many of these compounds are currently available as unregulated botanical preparations and their use by the public is increasing rapidly, clinicians need to consider the consequences of patients self-medicating with these preparations.

Plant Products as Antimicrobial Agents

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

Physiological and ecological constraints play key roles in the evolution of plant growth patterns, especially in relation to defenses against herbivores. Phenotypic and life history theories are unified within the growth-differentiation balance (GDB) framework, forming an integrated system of theories explaining and predicting patterns of plant defense and competitive interactions in ecological and evolutionary time. Plant activity at the cellular level can be classified as growth (cell division and enlargement) of differentiation (chemical and morphological changes leading to cell maturation and specialization). The GDB hypothesis of plant defense is premised upon a physiological trade-off between growth and differentiation processes. The trade-off between growth and defense exists because secondary metabolism and structural reinforcement are physiologically constrained in dividing and enlarging cells, and because they divert resources from the production of new leaf area. Hence the dilemma of plants: Th...

https://www.jstor.org/stable/pdfplus/2830650.pdf

The dilemma of plants: To grow or defend.

Antimicrobial activity of flavonoids

The formation, structure and nomenclature of phenolic compounds Distribution of phenolic compounds: phylogenetic constraints Why are phenolic compounds so important? Extraction and chemical quantitation of phenolics Biochemical techniques for tannins Bioassays and xenobiotic metabolism Separation of phenolic compounds Structure elucidation of unidentified phenolics Importance of phenolics in ecological studies - past and future

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Analysis of Phenolic Plant Metabolites

Plant Flavonoids in Biology and Medicine, Biochemical, Pharmacological and Structure-Activity Relationships

To explore sources of variation in tropical forest primate biomass, and, in particular, to test the hypothesis that soil conditions are a major ultimate determinant of the biomass of colobine monkeys and other primates, we compared data on the soils, vegetation, and primate community at a site in West Africa (Tiwai Island, Sierra Leone) with information from other sites, especially two other African sites (Douala-Edea in Cameroon, and Kibale Forest in Uganda). The biomass of eight anthropoid primate species in old secondary high forest on Tiwai was estimated from data on population densities assessed by transect samples combined with data on social group densities and individual body masses. Samples of soil and tree foliage were collected at the same site, and subjected to a variety of chemical and mechanical analyses. Our estimate of anthropoid biomass at Tiwai is 1229-1529 kg/kM2, including 682-889 kg/km2 of colobines. This is one of the highest primate biomasses recorded anywhere. The soils at Tiwai were found to be relatively high in sand content and low in pH, and to have low levels of mineral nutrients. Levels of condensed tannins in the mature foliage of the trees comprising a major part of the forest canopy were higher than at other sites, but the ratio of protein to fiber in this foliage was also higher than at any other site except Kibale. It is argued that a wide range of environmental factors affect primate population densities, and that nutrient-poor soils and high tannin levels in tree foliage do not necessarily produce a low primate (or colobine) biomass, as some earlier studies had suggested. Fur-

Determinants of Variation in Tropical Forest Primate Biomass: New Evidence from West Africa

Black colobus monkeys (Golobus salanas) in the Douala-Edea Reserve, a rain-forest on the coast of Cameroon, have been shown to avoid young and mature leaves of most of the common plants in their habitat and to feed disproportionately heavily on leaves of rare plants. The proportion of leaves in the diet was low compared to most colobines studied, and the monkeys spent over half their feeding time eating seeds. Patterns of food selection were analysed in relation to distribution of nutrients, digestion–inhibitors and toxins in the vegetation. Colobw satanas select food items that are rich in mineral nutrients and nitrogen and low in content of the general digestion-inhibitors, lignin and tannin. They achieve this in the following ways: (i) by feeding preferentially on young leaves, which have higher nutrient content and lower contents of digestion-inhibitors than mature leaves; (ii) by eating those mature leaves with highest nument content relative to content of digestion-inhibitors; and (iii) by eating seeds, which are sources of readily available energy and which, as an item class, are less rich in digestion-inhibitors. Seeds at Douala-Edea appear to contain Ins nitrogen than leaves and C. satanas selects those seeds with highest nitrogen content. It is suggested that seed-feeding may be facilitated by the ability of the forestomach flora of these ruminant-like monkeys to detoxify some of the secondary compounds contained in seeds. Avoidance of most unused young and mature leaf items is correlated with a low nutrienudigestion-inhibitor ratio; avoidance of most unused seeds could be accounted for by their low nitrogen contents. Most items whose avoidance could not be explained in terms of these major constraints on food selection possess secondary compounds likely to be toxic. It is proposed that relative importance of digestion-inhibitors, low nutrient content and toxins as constraints on food selection by generalist herbivores will vary greatly among forests with different nutrient and secondary chemistry profiles.

Food selection by black colobus monkeys (Colobus satanas) in relation to plant chemistry

Summary. A series of seventeen taxonomically diverse plant extracts rich in phenolic materials, including condensed and hydrolysable tannins, have been subjected to a series of biochemical analyses in an attempt to gather ecologically significant information about their interaction with proteins and amino acids. Methods employed were (i) protein-precipitation, using bovine serum albumin as substrate, followed by computation of specific activities of the tannins present in the extracts, and (ii) the inhibition of cellulase activity by tannin extracts bound to the cellulose substrate and free in solution. Both techniques revealed that all extracts contained tannin material. However, attempts to relate the results of the two procedures and in turn to relate them to information reported previously on the chemical properties of these extracts revealed that there was little correlation between any of the chemical or biochemical properties examined. From this analysis it would seem that whilst the analytical procedures available for studying tannins may generate ecologically useful information it is at present impossible, at least where plant material that is taxonomically diverse is being examined, to extrapolate from one type of measure to anticipate what would be observed from another type of measure. In addition to the above three other observations arose from this study. First, it appears to be generally true that there is not an absolute positive correlation between the level of protein precipitation and the incorporation of tannin in the tannin-protein precipitate. As relative protein concentration increases the proportion of tannin bound in the precipitate decreases, leading to less stable precipitates. Second, it is confirmed that some basic amino acids will precipitate with tannins, a phenomenon that could potentially influence amino acid balance in the diet. Third, complexation between tannin and protein absorbed on a cellulose substrate is able to interfere with the digestion of that cellulose by cellulase enzymes. Cellulose masking of this type may potentially effect the efficiency of cellulolytic activity in the rumen and if so suggests another subtle variation in the potential antifeedant properties of tannins.

Peter G. Waterman

Papers

Analysis of Phenolic Plant Metabolites

Plant Flavonoids in Biology and Medicine, Biochemical, Pharmacological and Structure-Activity Relationships

Determinants of Variation in Tropical Forest Primate Biomass: New Evidence from West Africa

Food selection by black colobus monkeys (Colobus satanas) in relation to plant chemistry

A critical analysis of techniques for measuring tannins in ecological studies : II. Techniques for biochemically defining tannins.