None named naringenin. The oxidation with the latter compound by flavanone 3-hydroxylase (F3H) yields the

November 21, 2023

None named naringenin. The oxidation with the latter compound by flavanone 3-hydroxylase (F3H) yields the dihydrokaempferol (colourless dihydroflavonol) that subsequently is often hydroxylated on the 3′ or 5′ position of the B-ring, by flavonoid 3′-hydroxylase (F3’H) or flavonoid 3′,5′-hydroxylase (F3’5’H), producing, respectively, dihydroquercetin or dihydromyricetin. Naringenin may also be directly hydroxylated by F3’H or F3’5’H to provide, respectively, eriodictyol and pentahydroxy-flavanone, that are again hydroxylated to dihydroquercetin and dihydromyricetin. The 3 dihydroflavonols thus synthesized are then converted to anthocyanidins (coloured but unstable pigments) by two reactions catalysed by dihydroflavonol reductase (DFR) and LDOX. The DFR converts dihydroquercetin, dihydrokaempferol and dihydromyricetin to leucocyanidin, leucopelargonidin and leucodelphinidin (colourless flavan-3,4-cis-diols), respectively. Subsequently, LDOX catalyses the oxidation of leucocyanidin, leucopelargonidin and leucodelphinidin to cyanidin (red-magenta anthocyanidin), pelargonidin (orange anthocyanidin) and delphinidin (RET Purity & Documentation purple-mauve anthocyanidin), respectively. All of the colours above described refer to a specific environmental condition, i.e., when the anthocyanidins are in an acidic compartment. The last popular step for the production of coloured and stable compounds (anthocyanins) requires the glycosylation of cyanidin, pelargonidin and delphinidin by the enzyme UDP-glucose:flavonoid 3-O-glucosyl transferase (UFGT). Ultimately, only cyanidin-3-glucoside and delphinidin-3-glucoside might be further methylated by methyltransferases (MTs), to become converted to peonidin-3-glucoside and petunidin- or malvidin-3-glucoside, respectively. The synthesis of PAs branches off the anthocyanin pathway after the reduction of leucocyanidin (or cyanidin) to catechin (or epicatechin) by the enzymatic activity of a leucoanthocyanidin reductase (LAR), or anthocyanidin reductase (ANR) [30]. The subsequent measures take place within the vacuolar compartments, exactly where the formation of PA polymers occurs by the addition of leucocyanidin molecules for the terminal unit of catechin or epicatechin, possibly catalysed by laccase-like polyphenol oxidases. However, the localization of these enzymes and their actual substrates are nonetheless controversial [31,32].Int. J. Mol. Sci. 2013,Figure 1. (A) Scheme of the flavonoid biosynthetic pathway in plant cells. Anthocyanins are synthesized by a multienzyme complicated loosely associated towards the endoplasmic reticulum (CHS, chalcone synthase; CHI, chalcone isomerase; F3H, flavanone 3-hydroxylase; F3’H, flavonoid 3′-hydroxylase; F3’5’H, flavonoid 3′,5′-hydroxylase; DFR, dihydroflavonol reductase; LDOX, leucoanthocyanidin oxidase; UFGT, UDP-glucose flavonoid 3-O-glucosyl transferase; MT, methyltransferase). Hexokinase Formulation Proanthocyanidins (PAs) synthesis branches off the anthocyanin pathway (LAR, leucoanthocyanidin reductase; ANR, anthocyanidin reductase; STS, stilbene synthase); the black arrows refer to biosynthetic measures missing in grapevine. Numbers next towards the flavonoid groups are connected to the chemical structures shown in (B). (B) Chemical structures in the main flavonoid groups.(A)(B)Int. J. Mol. Sci. 2013, 14 three. Mechanisms of Flavonoid Transport in Plant CellsIn the following section, recent advances around the models of flavonoid transport into vacuole/cell wall of diverse plant species, ascribed to a common membrane transporter-mediated transport (MTT), will b.