Flavonoids cyanidin

FIGURE 13.1 Typical structures for main pigment classes zeaxanthin (carotenoid), chlorophyll a (chlorophyll), quercetin (flavonoid), cyanidin (anthocyanidin), betanin (betalain), and alizarin (anthraquinone). 

Phytochemistry Fruits contain vitamin C, sugars, tannins, flavonoids (cyanidin-3-O-glucoside, phloridzin, isoquercitrin and glycosides of kaempferol, quercetin, taxifolin, and eriodictyol), conjugates of methyl gallate, pigments (carotene, lycopene, xanthophyll, etc.), pectins, pentosan and vitamins Kj, B, P and E. The seeds contain fatty oils and the flowers contain essential oil (Tohnachev 1976 Khalmatov et al. 1984 Hvattum 2002). 

Cyanidin is the most common anthocyanin in foods. In addition, anthocyanins are stabilized by the formation of complexes with other flavonoids (co-pigmentation). In the United States, the daily anthocyanin consumption is estimated at about 200 mg. Several promising studies have reported that consumption of anthocyanin-rich foods is associated with reductions of the risks of cancers - and atherosclerosis and with preventive effects against age-related neuronal and behavioral declines. These beneficial effects of anthocyanins might be related to their reported biological actions such as modulators of immune response and as antioxidants. Knowledge of anthocyanin bioavailability and metabolism is thus essential to better understand their positive health effects. 

Catechol-O-methyltransferase (COMT EC 2.1.1.6) is located in many tissues and catalyzes the methylation of polyphenols. The methylation is a well-established pathway in the metabolism of flavonoids such as those that undergo 3, 4 -dihydrox-ylation of ring B excreted as 3 -0-methyl ether metabohtes in rat bile. " Recently, the apparent methylation of both cyanidin-3-glucoside and cyanidin-3-sambubioside (cyanidin is an anthocyanin with a 3, 4 -dihydroxylation of ring B) to peonidin-3-glucoside and peonidin-3-sambubioside was reported in humans. In rats, this transformation occurred mainly in the liver and was catalyzed by COMT."°... 

Bahomn T, Luximon-Ramma A, Crozier A and Aruoma OI. 2004. Total phenol, flavonoid, proantho-cyanidin and vitamin C levels and antioxidant activities of Mauritian vegetables. J Sci Food Agric 84(12) 1553-1561. 

The riocus encodes the enzyme flavonoid 3 -hydroxylase (F3 H) [17, 18], and is an important controller of flux in the anthocyanin pathway in soybean seed coats (Fig. 4.1). F3 H diverts metabolic flux away from biosynthesis of orange (pelargoni-din) and blue (delphinidin) anthocyanins toward the red cyanidin-3-(9-glucoside, which is the main anthocyanin in the seed coats of black soybean [7, 8]. T increases the accumulation of delphidin-3-O-glucoside in black seed coats, even though it is not required for its biosynthesis [19]. Possible mechanisms for this include positive feedback, or the stabilization of the putative anthocyanin biosynthetic metabolon [20] by F3 Fl-derived membrane anchoring (Fig. 4.1). 

The W1 locus encodes flavonoid 3 5 -hydroxylase F3 5 H) [21]. F3 5 H diverts metabolic flux into the blue delphinidin branch of anthocyanin biosynthesis (Fig. 4.1). In the absence of F3 H activity (f), Wi and recessive wl give imperfect black and buff seed colors, respectively [10]. However, in black seeds, F3 H (T) phenotypically masks Wl. In contrast to its role in seeds, Wl has a prominent role in flower colors, as delphinidin-based anthocyanins are the major pigments in purple soybean flowers [22, 23]. Interestingly, F3 5 H is expressed at very low levels in flowers and seeds [21]. This suggests that, out of the two branch-point genes (i.e., F3 H and F3 5 H), it is the strong expression of F3 H in seed coats and weak expression in the flowers that determines preferential accumulation of cyanidin-based and delphinidin-based anthocyanins in these respective tissues [21]. 

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. 

Tian L, Pang Y, Dixon RA. 2007. Biosynthesis and genetic engineering of proantho-cyanidins and (iso)flavonoids. Phytochem Rev 7 445-465. 

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