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Biosynthesis of Food Constituents: Natural Pigments. Part 2 – a Review

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Biosynthesis of Food Constituents: Natural Pigments. Part 2 – a Review Czech J. Food Sci. Vol. 26, No. 2: 73–98 Biosynthesis of Food Constituents: Natural Pigments. Part 2 – a Review Jan VELÍšEK, Jiří DAVÍDEK and Karel CEJPEK Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Republic Abstract Velíšek J., Davídek J., Cejpek K. (2008): Biosynthesis of food constituents: Natural pigments. Part 2 – a review. Czech J. Food Sci., 26: 73–98. This review article is a part of the survey of the generally accepted biosynthetic pathways that lead to the most impor- tant natural pigments in organisms closely related to foods and feeds. The biosynthetic pathways leading to xanthones, flavonoids, carotenoids, and some minor pigments are described including the enzymes involved and reaction schemes with detailed mechanisms. Keywords: biosynthesis; xanthones; flavonoids; isoflavonoids; neoflavonoids; flavonols; (epi)catechins; flavandiols; leu- coanthocyanidins; flavanones; dihydroflavones; flavanonoles; dihydroflavonols; flavones; flavonols; anthocya- nidins; anthocyanins; chalcones; dihydrochalcones; quinochalcones; aurones; isochromenes; curcuminoids; carotenoids; carotenes; xanthophylls; apocarotenoids; iridoids The biosynthetic pathways leading to the tetrapyr- restricted in occurrence to only a few families of role pigments (hemes and chlorophylls), melanins higher plants and some fungi and lichens. The (eumelanins, pheomelanins, and allomelanins), majority of xanthones has been found in basi- betalains (betacyanins and betaxanthins), and cally four families of higher plants, the Clusiaceae quinones (benzoquinones, naphthoquinones, and (syn. Guttiferae), Gentianaceae, Moraceae, and anthraquinones) were described in the first part of Polygalaceae (Peres et al. 2000). Xanthones can this review (Velíšek & Cejpek 2007b). This part be classified based on their oxygenation, prenyla- deals with the biosynthesis of other prominent tion and glucosylation pattern. The majority of natural food colorants, xanthones, flavonoids, xanthones isolated so far are of the tetraoxygen- curcuminoids, carotenoids, isochromenes, and ated-type. Xanthones posses a number of remark- iridoids. able pharmacological activities (Peres et al. 2000) and have been used as, e.g. cardiovascular pro- 5 XanTHONES tective agents (Jiang et al. 2004) and antitumor promotors (Ito et al. 1998). The root of Yellow Xanthones, represented as the C6-C1-C6 system Gentian (Gentiana lutea, Gentianaceae) contains (Figure 30), are a group of about 70 yellow pigments several yellow xanthones, exemplified by gentisin Partly supported by the Ministry of Education, Youth and Sports of the Czech Republic (Project No. MSM 6046137305). 73 Vol. 26, No. 2: 73–98 Czech J. Food Sci. 10 HO O OH 4 5 HO HO O OH O HO O 3 6 ABC O OCH3 2 9 7 OH OH OH OH O 1 8 OH O O OH O HO OH xanthone gentisin mangiferin mangostin Figure 30 (1,3,7-trihydroxyxanthone), that are also found in benzophenone 3'-hydroxylase and converted to the Common Centaury (Centaurium erythraea, the 2,3',4,6-tetrahydroxyphenone intermediate, Gentianaceae) (Figure 31). The Gentiana root is common to both pathways. The crucial step in this bitter and becomes the principal vegetable bitter biosynthesis is the cyclisation of the benzophenone employed in medicine. Before the introduction to a xanthone, catalysed by xanthone synthases. of hops, Gentian, with many other bitter herbs, While in C. erythraea the xanthone synthase con- was used occasionally in brewing. It is a princi- verts this tetrahydroxybenzophenone intermediate pal ingredient in angostura bitters. 1,3,6,7-Tet- regioselective to 1,3,5-trihydroxyxanthone, the rahydroxyxanthone, the aglycone of C-glucoside xanthone synthase of H. androsaemum converts mangiferin occurs in mango leaves (Mangifera it to the 1,3,7-trihydroxyxanthone. The last step indica, Anacardiaceae) and has been used as a in the biosynthesis of the tetrahydroxyxanthones yellow textile dye. It is also known to exhibit anti- is the introduction of a hydroxyl group to the inflammatory, antioxidant, and antiviral effects. C-ring of the xanthone skeleton. This reaction Mangostin is the major xanthone constituent of is carried out by the plant-specific cytochrome the mangosteen tree (Garcinia mangostana, Clu- P450-dependend monooxygenase xanthone 6-hy- siaceae) (Bennet et al. 1990). droxylase to form 1,3,5,6-tetrahydroxyxanthone in The biosynthesis of xanthones (Figure 31) origi- C. erythraea and 1,3,6,7-tetrahydroxyxanthone in nates mainly from a mixed shikimate-acetate path- H. androsaemum. Another representative of the way; however xanthones entirely derived from Gentianaceae, chirayta (Swertia chirata), hydroxy- acetate have also been reported in lower plants lates 1,3,5-trihydroxyxanthone in the C-8 position (Peres et al. 2000). The main steps in the xanthone of the C-ring resulting in the major xanthone of biosynthesis involve the condensation of shikimate this species 1,3,5,8-tetrahydroxyxanthone (Wang and acetate moieties, which constitute a benzo- et al. 2003a; BIOCYC 2007). phenone intermediate followed by a regioselective, oxidative mediated intramolecular coupling to 6 FLAVONOIDS form the xanthone ring (Peters et al. 1998). The shikimate derivatives used as entry compounds Flavonoids comprise a widespread group of more for the tetrahydroxyxanthone biosynthesis differ than 4000 higher plant secondary metabolites. in the individual plants. Many flavonoids are easily recognised as water- In the Common Centaury, the biosynthesis of soluble flower pigments in most angiosperm fami- tetrahydroxyxanthone is obtained via 3-hydroxy- lies (flowering plants), which themselves provide benzoic acid (that appears to originate directly the major source of food plants (fruits, vegetables, from the shikimate pathway) by the stepwise con- and grains). Molecules of flavonoids posses fif- densation of 3-hydroxybenzoyl-CoA (formed un- teen carbon atoms and contain two benzene rings der catalysis of 3-hydroxybenzoate-CoA ligase, (rings A and C, respectively) connected with a EC 6.2.1.-) with three malonyl-CoA to form an chain built up of three carbon atoms that becomes intermediate 2,3',4,6-tetrahydroxybenzophenone a part of O-heterocyclic (pyrane) cycle (ring B). (benzophenone synthase, EC 2.3.1.151). In Hyperi- The skeleton of flavonoids can be thus represented cum androsaemum (Clusiaceae), the biosynthesis as the C6-C3-C6 system (1,3-diarylpropanoids). of this tetrahydroxyxanthone proceeds via ben- Many flavonoids are hypothetically derived from zoic acid and benzoyl-CoA (benzoate-CoA ligase, flavan (IUPAC 2006) (Figure 32). EC 6.2.1.25). The new intermediate, 2,4,6-tri- Various subgroups of flavonoids are classified hydroxybenzophenone is further hydroxylated by according to their substitution pattern of the ring B. 74 Czech J. Food Sci. Vol. 26, No. 2: 73–98 HOOC OH HOOC 3-hydroxybenzoic acid benzoic acid ATP + HS-CoA EC 6.2.1.25 ATP + HS-CoA AMP + PP EC 6.2.1.- OO 3 AMP + PP CoA OH malonyl-CoA 4 HS-CoA + 3 CO 2 HO OH S S CoA OH CoA EC 2.3.1.151 O O OH O 3-hydroxybenzoyl-CoA benzoyl-CoA 2,4,6-trihydroxybenzophenone OO NADPH + O2 3 CoA OH malonyl-CoA 4 HS-CoA + 3 NADP + H O EC 2.3.1.151 CO 2 2 HO OH OH OH O NADPH + O2 NADPH + O2 2,3´,4,6-tetrahydroxybenzophenone NADP + 2 NADP + 2 H2O H2O OH HO O HO O OH OH O OH O 1,3,5-trihydroxyxanthone NADPH + O2 1,3,7-trihydroxyxanthone NADPH + O2 NADPH + O2 NADP + H2O NADP + H2O NADP + H2O OH OH HO O HO O OH HO O OH OH OH O OH OH O OH O 1,3,5,8-tetrahydroxyxanthone 1,3,5,6-tetrahydroxyxanthone 1,3,6,7-tetrahydroxyxanthone Figure 31 Both the oxidation state of the heterocyclic ring the three rings and oxidation of the C-4 hydroxyl and the position of the ring B substituents are group. Examples of the seven major subgroups of important in the classification. Derivations include the most important structural types are given in oxidation of the 2(3)-carbon-carbon double bond Figure 33. The compounds are listed according in flavan, hydroxylation at various positions of to their oxidation degree that concerns the three 75 Vol. 26, No. 2: 73–98 Czech J. Food Sci. 3´ nylbenzopyrylium or 2-phenylchromenylium), 2´ 4´ 1 anthocyanidins became the most prominent group 8 C O 5´ of water-soluble plant pigments as they are re- 7 1´ A B 2 6´ sponsible for blue, purple, violet, magenta, pink, 6 3 and red coloration.17 5 4 In a few cases, the six-membered heterocyclic flavan ring B occurs in an isomeric open form (chalcones and dihydrochalcones) or is replaced by a five- Figure 32 membered ring (aurones). Chalcones and aurones belong to the prominent flower pigments that are central carbon atoms (ring B). In the rows, the responsible for their golden and yellow colora- oxidation degree increases from the left to the tion. Isoflavonoids or 3-phenylchromen-4-ones right while in the columns the oxidation degree (1,2-diarylpropanes, colourless to light yellow is equal. In the same direction their coloration compounds derived from isoflavan) and neoflavo- increases, too. Catechins and leucoanthocyanidins noids or 4-phenylcoumarins (1,1-diarylpropanes are uncoloured compounds, flavanones are from derived from neoflavan) are less common flavo- uncoloured to light yellow like flavanonoles, fla- noids having the ring C attached to the ring B at vones and flavonols are yellow. Due to the system C-3 and C-4, respectively (Figure 34). Isoflavonoids of conjugated doubleO bonds (flavilium or 2-pheO - and neoflavonoidsO can be regarded as abnormalO OH OH OH OH OH O O flavanols (catechins) flavandiols
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