Flavonoid Flavanones

Flavones and flavanones were less frequently consumed during the 4-day collection period. Flavones were not consumed at all by 38 participants, while 29 people did not consume any citrus flavonoids — flavanones. The interquartile range of intake of flavones was relatively limited, ranging from 0.0 to 2.0 mg/day. Flavone consumption was not normally distributed and was negatively skewed toward a lack of consumption of foods rich in flavones such as olives and lettuce. Likewise, flavanone intake was also not normally distributed with a mean flavanone intake of 1 mg/day compared to the median intake of 1.2 mg/day. This is accounted for by the fact that the range of flavanone intakes was very wide (0 to 239 mg/day), 36%i of participants not consuming any flavanone-rich foods. The main dietary... 

Coumaric acid Ferulic acid Caffeic acid Flavonoids Flavanones Narirutin C. paradisi, C. aurantium, C. sinensis, ... 

From the biosynthetic relationship among different classes of flavonoids, flavanones derived from the cyclization of chalcones. Although there is a quite number of biflavanones in the literature, no biflavanone has so far been identified from the Dorstenia genus. 

Flavonoids are one of the largest classes of phenylpropanoid-derived plant specialized metabolites, with 10,000 different members. They consist of two main groups, the 2-phenylchromans (flavonoids flavanones, flavones, flavonols, flavan-3-ols, anthocy-anidins) and the 3-phenylchromans (isoflavonoids isoflavones, iso-flavans, pterocarpans). Some flavonoids and their metabolites exhibit positive effects for disease therapy and chemoprevention [218,219],... 

Within the plant secondary metabolites of flavonoids, flavanones define one of the minor subclasses. They may be called dihydroflavones. The basic chemical structure of flavanones involves two benzene rings (A and B), which are linked by a heterocyclic ring (C). The most characteristic point of flavanone structures is that the C-ring is saturated. Flavanones have an asymmetric carbon at C2-position. 

Figure 6. Kumquats are rich in flavonoids (flavanones and dihydrochalcones), carotenoids (beta carotene) and phenolic acids (cinnamic acids). These dietary polyphenols actually exhibit a dual effect through indirect neuroprotection against oxidative stress and indirect protection through suppression of gha-mediated inflammation.

Sesquiterpenes and flavonoids (flavones, flavanones, flavanes) are two elasses of natural substan-ees which occur frequently in plants and whieh have 15 C atoms in their framework. The nine... 

In addition to the bitter acids and essential oils, the flowers of hops offer a rich array of polyphenolic compounds, primarily chalcones and their accompanying flavanones, many of which are prenylated derivatives (Stevens et al., 1997,1999a, b). The most prominent flavonoid in all plants studied was xanthohumol [342] (3 -prenyl-6 -0-methylchalconaringenin chalconaringenin is 2, 4, 6, 4-tetrahydroxychalcone) (see Fig. 4.11 for structures 342-346). Several additional chalcones—variously adorned with 0-methyl and/or C-prenyl functions—were also encountered, along with their respective flavanones. Three new compounds were described in the Stevens et al. 

The chemical formulae for a variety of plant phenols are given in Fig. 16.2, including examples of simpler phenols, such as cinnamic acid derivative, and of tocopherols, flavonoids, flavonoid glycosides and anthocyanidins. The flavonoids include the following subclasses flavanones (taxifolin), flavones (luteolin), flavonols (quercetin) and flavanols (catechin/epicatechin). The... 

Fig. 5 Scheme of the flavonoid pathway leading to synthesis of proanthocyanidins. The enzymes involved in the pathway are shown as follows CHS = chalcone synthase CHI = chalcone isomerase F3H = flavanone-3B-hydroxylase DFR = dihydroflavonol-4-reductase LDOX = leucoanthocynidin dioxygenase LAR = leucoanthocyanidin reductase ANR = anthocyanidin reductase adapted from [27] and [28]... 

Each plant tissue tends to have an obviously distinctive profile of flavonoids. The flavonoid content can reach about 0.5% in pollen, 10% in propolis, and about 6 mg/kg in honey. Havonoid aglycones appear to be present only in propolis and honey, while pollen contains flavanols in herosidic forms. The flavonoids in honey and propolis have been identified as flavanones and flavanones/flavanols (Campos et ah, 1990). The antimi-crobially active flavanone pinocembrine was foimd to be a major flavonoid in honey (Bogdanov, 1989). Amiot et ah (1989) studied two blossom and two honeydew Swiss honey samples and foimd that pinocembrine was the main flavonoid. Pinocembrine concentration varied between 2 and 3 mg/kg (Bogdanov, 1989). Berahia et ah (1993) analyzed sunflower honey samples and detected six flavone/flavols, four flavanone/ flavols, and pinocembrin, of which pinocembrin is the main flavonoid. The flavonoids in sunflower honey and propolis were characterized and assessed for their effects on hepatic drug-metabolizing enzymes and benzo [fl]pyrene-DNA adduct formation (Sabatier et ah, 1992 Siess et ah, 1996). 

Root flavonoids that may act as signals for the initiation and development of endomycorrhizal and ectomycorrhizal symbio.ses have been identified (see Chap. 7). Metabolites of the phenylpropanoid pathways apparently act as signaling molecules in endo- and ectomycorrhizal interactions (14). The role of flavonoids is still controversial, but a variety of flavanones, flavones, and isoflavones... 

Effects of Allelochemlcals on ATP Supply. Allelochemlcals might decrease the ATP content of tissue by either increasing ATP utilization or decreasing ATP production. Some allelochemlcals that inhibit mineral absorption decrease ATP content of plant tissues. Salicylic acid decreased the ATP content of oat roots in a pH dependent manner (Figure 3). This result suggested that mitochondrial production of ATP was decreased in the tissue. On the other hand, Tillberg (38) found that salicylic acid and cinnamic acid increased the ATP content of Scenedesmus. Various flavonoids inhibited ATP production by mitochondria Isolated from cucumber (Cucumls satlvus L.) hypocotyls (54). Flavones such as kaempferol were more inhibitory than the corresponding flavanones. Substituted cinnamic acids such as caffeic acid were not inhibitory. 

Flavanonols Flavanonols can be considered as flavanones with a hydroxyl group on position 3. They are sometimes referred to as dihydroflavonols. Similar to the situation of flavanones, flavanonols are no longer a minor subgroup of flavonoids, and they are a structurally highly diverse and multisubstituted subgroup (Grayer and Veitch 2006). A well-known flavanonol is taxifolin from citrus fruits (Kawaii and others 1999) (see Table 5.1 and Fig. 5.2). 

Flavanones In some cases, flavanones produced by CHI will accumulate to sizeable amounts instead of being diverted away to form flavonols, anthocyanins, and flavanols (see Fig. 5.4). These flavanone products, hesperetin and naringenin being the most common, are frequently encountered in citrus fruits and juices (USDA Flavonoids Database Release 2.1,2007). In most of these cases, essentially no flavonols or anthocyanins are encountered the flavonoid pathway is essentially blocked at the F3H step. 

Grayer RJ and Veitch NC. Flavanones and dihydroflavonols. In Anderson OM, Markham KR. editors. Flavonoids Chemistry, Biochemistry and Applications. Boca Raton, FL CRC Press/Taylor Francis Group, pp. 918—1002. 

Turnbull JJ, Nakajima J, Welford RW, Yamazaki M, Saito K and Schofield CJ. 2004. Mechanistic studies on three 2-oxoglutarate-dependent oxygenases of flavonoid biosynthesis anthocyanidin synthase, flavonol synthase, and flavanone 33-hydroxylase. J Biol Chem 279 1206-1216. 

Flavonoids are a complex group of polyphenolic compounds with a basic C6-C3-C6 structure that can be divided in different groups flavonols, flavones, flavanols (or flavan-3-ols), flavanones, anthocyanidins, and isoflavones. More than 6,000 flavonoids are known the most widespread are flavonols, such as quercetin flavones, such as lu-teolin and flavanols (flavan-3-ols), such as catechin. Anthocyanidins are also bioactive flavonoids they are water-soluble vegetable pigments found especially in berries and other red-blue fruits and vegetables. 

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