Secondary metabolites phenolic

MeUdwlites Some moss species contain considerable amounts of aiachidonic acid. M. form a surprising diversity of previously unknown secondary metabolites. Phenolic compounds and terpenes dominate although clear differences between the individual classes of M. are apparent. Anthocerotae are characterized by lig-nans, liverworts mainly by terpenes - mostly sesquiterpenes (often enantiomers of those occurring in higher plants) - and bibenzyl or bisbibenzyl derivatives, Musci by the occurrence of biflavonoids, sphagnorubins (peat mosses) and coumarin derivatives (Polytrichaceae). Alkaloids are very rare. Recently sterile cultures (in vitro culmres ) have been introduced to obtain the secondary metabolites from M. The production of substances corresponds qualitatively to that of M. in natural locations. 

The biosynthetic pathways are universal in plants and are responsible for the occurrence of both primary metabolites (carbohydrates, proteins, etc.) and secondary metabolites (phenols, alkaloids, etc.). Secondary compounds were once regarded as simple waste products of a plant s metabolism. However, this argument is weakened by the existence of specialist enzymes, strict genetic controls and the high metabolic requirements of these componnds (Waterman and Mole 1994). Today most scientists accept that many of these componnds serve primarily to repel grazing animals or destrnctive pathogens (Cronquist 1988). 

Neither the mechanism by which benzene damages bone marrow nor its role in the leukemia process are well understood. It is generally beheved that the toxic factor(s) is a metaboHte of benzene (107). Benzene is oxidized in the fiver to phenol [108-95-2] as the primary metabolite with hydroquinone [123-31-9] catechol [120-80-9] muconic acid [505-70-4] and 1,2,4-trihydroxybenzene [533-73-3] as significant secondary metabolites (108). Although the identity of the actual toxic metabolite or combination of metabolites responsible for the hematological abnormalities is not known, evidence suggests that benzene oxide, hydroquinone, benzoquinone, or muconic acid derivatives are possibly the ultimate carcinogenic species (96,103,107—112). 

Polyphenols are the most abundant antioxidants in human diets. They are secondary metabolites of plants. These compounds are designed with an aromatic ring carrying one or more hydroxyl moieties. Several classes can be considered according to the number of phenol rings and to the structural elements that bind these rings. 

Plant metabolism can be separated into primary pathways that are found in all cells and deal with manipulating a uniform group of basic compounds, and secondary pathways that occur in specialized cells and produce a wide variety of unique compounds. The primary pathways deal with the metabolism of carbohydrates, lipids, proteins, and nucleic acids and act through the many-step reactions of glycolysis, the tricarboxylic acid cycle, the pentose phosphate shunt, and lipid, protein, and nucleic acid biosynthesis. In contrast, the secondary metabolites (e.g., terpenes, alkaloids, phenylpropanoids, lignin, flavonoids, coumarins, and related compounds) are produced by the shikimic, malonic, and mevalonic acid pathways, and the methylerythritol phosphate pathway (Fig. 3.1). This chapter concentrates on the synthesis and metabolism of phenolic compounds and on how the activities of these pathways and the compounds produced affect product quality. 

Flavonoids are secondary metabolites generally occurring in various plants as glycosides. The chemical structure of flavonoids shows high variety. The basic structure of flavons and flavonols is the 2-phenylbenzo-gamma-pyrone. Flavonoids generally contain two phenol rings linked with a linear three-carbon chain (chalcones) or with three carbon... 

Plant parts often differ in their levels of secondary metabolites (Table 11.4), some containing extremely high levels. For example, the creosote bush, Larrea tridentata, of the western United States has phenolic resins concentrated in leaves, amounting to as much as 18% of dry weight. In experiments, desert woodrats, Neotoma lepida, selected plant parts of creosote bush with low levels of resins (Meyer and Karazov 1989). 

The nutritional value of the diet influences the ability of herbivores to detoxify plant secondary metabolites (Schwass and Finley, 1985). For instance, voles in winter have to consume the bark of birch Betula sp.). This causes stress and leads to poor growth and high mortality among young animals. Birch bark contains phenolics and terpenoids. Both are metabolized by cytochrome P450 monooxidases in phase I and conjugated with glucuronic acid in phase II. 

Volatile compounds formed by anabolic or catabolic pathways include fatty acid derivatives, terpenes and phenolics. In contrast, volatile compounds formed during tissue damage are typically formed through enzymatic degradation and/ or autoxidation reactions of primary and/or secondary metabolites and includes lipids, amino acids, glucosinolates, terpenoids and phenolics. 

There is a huge variety of plant defensive secondary metabolites that has been the subject of major phytochemical [1-6] or pharmacological and toxicological [7-12] compilations. This structural complexity is very briefly reviewed below before considering those plant bioactives with signal transduction targets. The major groups are the phenolics, the terpenoids and the alkaloids as well as bioactives structurally related to... 

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