Flavonoid quinone

Arcmatic compounds phenols, phenolic acids, cinnamic acid derivatives, coumarins, flavonoids, quinones, and tannins, all of which are aromatic compounds, comprise the largest group of secondary plant products. They are often referred to as "phenolics" and have been identified as allelopathic agents in more instances than all of the other classes of compounds combined 5). 

Like coumarinolignans, the dioxane bridge of flavonolignans undergoes mass spectrometric RDA cleavage to give rise to a substimted flavonoid-quinone ion (H) and a typical phenylpropanoid ion (I), as shown in Fig. 18. 

Polyterpenes, diterpenes (phorbol esters), lipophilic flavonoids, quinones... 

Awad HM, Boersma MG, Boeren S, van Bladeren PJ, Vervoort J, Rietjens IM. The regioselectivity of glutathione adduct formation with flavonoid quinone/quinone methides is pH-dependent. Chem Res Toxicol 2002 15 343 351. 

The shikimate pathway is the major route in the biosynthesis of ubiquinone, menaquinone, phyloquinone, plastoquinone, and various colored naphthoquinones. The early steps of this process are common with the steps involved in the biosynthesis of phenols, flavonoids, and aromatic amino acids. Shikimic acid is formed in several steps from precursors of carbohydrate metabolism. The key intermediate in quinone biosynthesis via the shikimate pathway is the chorismate. In the case of ubiquinones, the chorismate is converted to para-hydoxybenzoate and then, depending on the organism, the process continues with prenylation, decarboxylation, three hydroxy-lations, and three methylation steps. - ... 

Quercetin is a naturally occurring flavonoid with both antioxidant and prooxidant activities (Scheme 10.12).90 It has been demonstrated in a variety of bacterial and mammalian mutagenicity experiments that quercetin has mutagenic properties that could be related to quinoid formation.91,92 Quercetin is initially oxidized to an o-quinone, which rapidly isomerizes to di-QMs that could also be called extended... 

E) coumarins, (F) quinones, (G) flavonoids, (H) tannins, (I) alkaloids, (J) terpenoids and steroids and (K) miscellaneous and unknowns. Although many of these compounds are secondary products of plant metabolism, several are also degradation products which occur in the presence of microbial enzymes. 

The initial oxidation of the flavanol components of fresh leaf to quinone structures through the mediation of tea polyphenol oxidase is the essential driving force in the production of black tea. While each of the catechins is oxidizable by this route, epigallocatechin and its galloyl ester are preferentially oxidized.68 Subsequent reactions of the flavonoid substances are largely nonenzymic. 

Cytotoxic prooxidant effects of flavonoids can also be a consequence of their enzymatic oxidation. For example, it was found that quercetin was oxidized by lactate peroxide to form semiquinone and quinone [181]. 

Complex phenolics Coumarins, phenolic quinones, lignins, flavonoids, stilbenes, hydrolyzable tannins, condensed (or catechin) tannins, phenolic lipids... 

Laccase (EC 1.10.3.2), arising from fungal contamination by B. cinerea, which is the agent of gray and noble rot, also catalyzes reaction 2 and accepts a wider range of substrates, including, in particular, glycosylated flavonoids such as anthocyanins and also p-diphenols (oxidized to p-quinones). ... 

The electrophilic primary and secondary quinones undergo addition of nucleophiles, including flavonoids. For instance, nucleophilic addition of catechin to its enzymatically generated quinone yielded a catechin dimer in which the catechin moieties are linked through a C6 C8 biphenyl linkage. This B-type dehydrodicatechin further oxidized to yellow pigments. Additional dehydrodicatechins arise from radical coupling of the catechin semi-quinones formed by retro-disproportionation, in which the catechin moieties are linked... 

Awad, H.M., Boersma, M.G., Boeren, S., van Bladeren, P.J., Vervoort, J., and Rietjens, I.M., Structure-activity study on the quinone/quinone methide chemistry of flavonoids, Chem. Res. Toxicol, 14, 398, 2001. 

Parasitic plants often use chemicals released by their host plant to stimulate seed germination, to locate the host, or for haustorial development. Many different compounds are involved, including strigolactones, quinones, coumarins, flavonoids, and other phenolics. Flavonoids contribute to signaling in some species but not others. Haustorial development in Triphysaria versicolor can be induced in vitro by the anthocyanidins petunidin, cyanidin, pelargonidin, delphinidin, as well as their glycosides obtained from the host plant.Anthocyanins are not usually found in root exudates, however, and thus the mechanism by which they affect natural signals for parasitic plants in the soil is not clear. 

Nunez-Alarcon, J. and Quinones, M., Epicuticular flavonoids from Haplopappus baylahuen and the hepatoprotective effect of the isolated 7-methylaromadendrin, Biochem. Syst. Ecol, 23, 453, 1993. 

The flavonoid sideroxylonal B has been synthesised from 3,5-dimethoxyphenol through initial conversion to the 2-(3 -methylbutan-l -ol) derivative. Reaction with EtMgBr simultaneously generates the quinone methide and the 2-isopentenylphenol which react together to produce the flavan (Scheme 12) <99TL1925>. 

The phenolics include anthocyanins, anthraquinones, benzofurans, chromones, chromenes, coumarins, flavonoids, isoflavonoids, lignans, phenolic acids, phenylpropanoids, quinones, stilbenes and xanthones. Some phenolics can be very complex in structure through additional substitution or polymerization of simpler entities. Thus xanthones can be prenylated and flavonoids, lignans and other phenolics can be glycosylated. Condensed tannins involve the polymerization of procyaninidin or prodelphinidin monomers and hydrolysable tannins involve gallic acid residues esterified with monosaccharides. As detailed in this review, representatives of some major classes of plant-derived phenolics are potent protein kinase inhibitors. 

Little information about the mechanism of action of flavonoids is anticipated from in vivo studies. The mechanism of catechin and morin seems to be related to an increase of the activity of detoxifying enzymes like glutathione-S-transferase and NADPH quinone reductase [198, 211]. Similarly, EGCG effect at the colonic level is associated to an increase in tissue superoxide dismutase levels, suggesting that it may act through a potentiation of the antioxidative defense [210]. 

There are diffent pathways by which all phenolic compounds are synthesized [6,7]. The shikimate/arogenate pathway leads, through phenylalanine, to the majority of plant phenolics, and therefore we shall centre the present revision on the detailed description of this pathway. The acetate/malonate pathway leads to some plant quinones but also to various side-chain-elongated phenylpropanoids (e.g. the group of flavonoids). Finally, the acetate/mevalonate pathway leads by dehydrogenation reactions to some aromatic terpenoids. 

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