Plant polyphenol flavanols

Based on chemical, thermodynamic, and kinetic data, this chapter will discuss the mechanisms proposed for polyphenol biological actions, especially antioxidant reactions. Although most of the points addressed in this chapter are valid for an important number of plant polyphenols, we will focus the analysis on flavonoids and, in particular, on flavanols. 

Polyphenoloxidase (PPO, EC 1.14.18.1) is one of the most studied oxidative enzymes because it is involved in the biosynthesis of melanins in animals and in the browning of plants. The enzyme seems to be almost universally distributed in animals, plants, fungi, and bacteria (Sanchez-Ferrer and others 1995) and catalyzes two different reactions in which molecular oxygen is involved the o-hydroxylation of monophenols to o-diphenols (monophenolase activity) and the subsequent oxidation of 0-diphenols to o-quinones (diphenolase activity). Several studies have reported that this enzyme is involved in the degradation of natural phenols with complex structures, such as anthocyanins in strawberries and flavanols present in tea leaves. Several polyphenols... 

Plant-derived products Polyphenols (derivatives of hydroxycinnamic acid, hydroxybenzoic acid, flavonols,3 flavones,3 anthocyanidins,3 flavanols,3 isoflavones,3 flavanones,3 stilbenes, lignans), glucosynolates, carotenoids (am /3-, y-, 8-carotene, lycopene, luthein, xeaxantin, canthaxantin), phytic acid, allicin... 

The polyphenols are a series of phytochemicals synthesized by plants. They include the bioflavonoids anthocyanins, coumestanes, flavonoids, isoflavonoids, and stil-benes (Figure 4.1). Each bioflavanoid class is subdivided into other groups, e.g., flavones, flavans, flavanols, flavonols, and flavanones (Figure 4.2). Another class of polyphenol is the oligomeric polyphenols, such as the proanthocyanidins, found in the grape and various berries (black currant, blueberry, etc.). 

Although flavanols, also called catechins, seem to be widely distributed in plants, they are rich only in tea leaves, where catechins may contribute up to 30% of dry leaf weight. The antioxidative and antitumor properties of green and black teas and their tea polyphenols are extensively studied. It seems that tea polyphenols are important not only for plants but also for humans. Therefore, this brief review will discuss the current data with a particular emphasis on the effects of tea polyphenols on the cellular oxidative stress and cancer chemopreventive properties. The action mechanisms of several phytopolyphenols on cancer chemoprevention will be elaborated. 

Anthocyanins, flavanols and phenolic acids are the main polyphenols of grapes and grape-derived foods, responsible for their major organoleptic properties. Anthocyanins are directly involved in the color of most red fruits including grapes (7) while flavanols are thought to make an important contribution to the astringency and bitterness of plant derived foods (2,3). 

Havanols are a wide group of polyphenols that include flavan-3-ols (e.g., catechin and proanthocyanidins), flavan-4-ols, and flavan-3,4-diols. They arise from plant secondary metabolism through condensation of phenylalanine derived from the shikimate pathway with malonyl-CoA obtained from citrate that is produced by the tricarboxylic acid cycle, leading to the formation of the key precursor in the flavonoids biosynthesis the naringenin chalcone. The exact nature of the molecular species that undergo polymerization and the mechanism of assembly in proanthocyanidins are still unknown. From a structural point of view, flavanols... 

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