The gene coding for the DOPA dioxygenase involved in betalain biosynthesis in Amanita muscaria and its regulation

Hinz, Ursula; Fivaz, Jan; Girod, Pierre‐Alain; Zyrd, J.-P.

doi:10.1007/s004380050539

Cited by 54 publications

(51 citation statements)

References 19 publications

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“…2). The formation of betalamic acid from DOPA requires the extradiol cleavage of the 4,5 bond carried out by a DOPA dioxygenase, first identified in the basidiomycete fly agaric (Amanita muscaria) (Hinz et al 1997). The plant enzyme was subsequently cloned by a subtractive cDNA approach using Portulaca grandiflora isogenic lines with different color phenotypes (Christinet et al 2004).…”

Section: Biosynthesismentioning

confidence: 99%

Betalains in the era of global agri-food science, technology and nutritional health

et al. 2008

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Natural pigments from plants are of growing interest as substitutes for synthetic dyes in the food and pharmaceutical industry and they increase their added value if they possess positive effects on health. These pigments can be added as such if they are in the legal authorized lists of additives or can be added as phytochemical-enriched plant extract achieving the original product, which has received it, the new nomenclature of functional food. In this way, we comprise on this review a wide point of view of a group of natural pigments known as betalains. From a chemical point of view, betalains are ammonium conjugates of betalamic acid with cyclo-DOPA (betacyanins, violet) and aminoacids or amines (betaxanthins, orange or yellow), which are compounds present in our diet. Besides and taking into account that one type of betalain, betanin is approved as food colorant (E-162) by the European Union and that enlarges the specific weight of these compounds in the diet, we have evolved an overview from the biosynthesis, technology and promoting production, industrial uses as pigments up to physiological and nutritional biovailability or biological and health-promoting properties of betalains for accessible information to industrials, researchers and consumers.

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Section: Biosynthesismentioning

confidence: 99%

Betalains in the era of global agri-food science, technology and nutritional health

et al. 2008

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“…A tyrosinase (Mueller et al, 1996;Steiner et al, 1999) is needed to convert the amino acid Tyr to DOPA, and a ring-opening extradiol DOPA-4,5-dioxygenase is crucial for the synthesis of the chromophore betalamic acid (see Fig. 1; Girod and Zrÿ d, 1991a;Hinz et al, 1997;Schliemann et al, 1998). The formation of cyclo-DOPA is needed for the building of violet betanidin and betacyanins .…”

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confidence: 99%

“…In the mean time, a DOPA-dioxygenase was purified from Amanita muscaria (Girod and Zrÿ d, 1991a), and an Amanita sp. DODA gene was isolated and characterized (Hinz et al, 1997;Mueller et al, 1997b). The fungal enzyme possesses a unique double 2,3-and 4,5-aromatic ring-cleaving activity, allowing the simultaneous biosynthesis of betalain and muscaflavin.…”

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Characterization and Functional Identification of a Novel Plant 4,5-Extradiol Dioxygenase Involved in Betalain Pigment Biosynthesis in Portulaca grandiflora

et al. 2004

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Betalains are pigments that replace anthocyanins in the majority of families of the plant order Caryophyllales. Betalamic acid is the common chromophore of betalains. The key enzyme of the betalain biosynthetic pathway is an extradiol dioxygenase that opens the cyclic ring of dihydroxy-phenylalanine (DOPA) between carbons 4 and 5, thus producing an unstable seco-DOPA that rearranges nonenzymatically to betalamic acid. A gene for a 4,5-DOPA-dioxygenase has already been isolated from the fungus Amanita muscaria, but no homolog was ever found in plants. To identify the plant gene, we constructed subtractive libraries between different colored phenotypes of isogenic lines of Portulaca grandiflora (Portulacaceae) and between different stages of flower bud formation. Using in silico analysis of differentially expressed cDNAs, we identified a candidate showing strong homology at the level of translated protein with the LigB domain present in several bacterial extradiol 4,5-dioxygenases. The gene was expressed only in colored flower petals. The function of this gene in the betalain biosynthetic pathway was confirmed by biolistic genetic complementation in white petals of P. grandiflora genotypes lacking the gene for color formation. This gene named DODA is the first characterized member of a novel family of plant dioxygenases phylogenetically distinct from Amanita sp. DOPA-dioxygenase. Homologs of DODA are present not only in betalain-producing plants but also, albeit with some changes near the catalytic site, in other angiosperms and in the bryophyte Physcomitrella patens. These homologs are part of a novel conserved plant gene family probably involved in aromatic compound metabolism.Betalains are vacuolar pigments that entirely replace anthocyanins in most plants of the order Caryophyllales, with the exception of Caryophyllaceae and Molluginaceae (for review, see Strack et al., 2003). Betalains are also present in some basidiomycete fungi belonging to the Amanita and Hygrocybe genera. Betalains provide a key taxonomic criterion in our understanding of Caryophyllales evolution (Cuenoud et al., 2002); the origin of the alternative pigment biosynthetic pathway is still unknown (Clement and Mabry, 1996), and the purpose of our work is to provide, through the characterization of a key biosynthetic enzyme, one element of the answer to this problem.Information on the biochemistry and genetics of the plant betalain pathway is scarce. Genetic analysis of the betalain biosynthetic pathway in the ornamental plant Portulaca grandiflora (Pg) indicates that four structural genes would be sufficient to account for the different color phenotypes observed in petals (Trezzini and Zrÿ d, 1990). A tyrosinase (Mueller et al., 1996;Steiner et al., 1999) is needed to convert the amino acid Tyr to DOPA, and a ring-opening extradiol DOPA-4,5-dioxygenase is crucial for the synthesis of the chromophore betalamic acid (see Fig. 1; Girod and Zrÿ d, 1991a;Hinz et al., 1997;Schliemann et al., 1998). The formation of cyclo-DOPA is needed for the bui...

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“…The first betalain ring structure biosynthetic gene to be cloned was DODA from the mushroom, A. muscaria [32]. To clone this gene, Zrÿd and coworkers purified the protein from mushroom caps, raised antibodies against it, and used the anti-DODA antibodies to screen an Amanita cDNA expression library in Escherichia coli.…”

Section: Cloning the Betalamic Acid Biosynthetic Gene 45-dopa-dioxymentioning

confidence: 99%

The Betalain Secondary Metabolic Network

Hatlestad

Lloyd

2015

Pigments in Fruits and Vegetables

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The gene coding for the DOPA dioxygenase involved in betalain biosynthesis in Amanita muscaria and its regulation

Cited by 54 publications

References 19 publications

Betalains in the era of global agri-food science, technology and nutritional health

Betalains in the era of global agri-food science, technology and nutritional health

Characterization and Functional Identification of a Novel Plant 4,5-Extradiol Dioxygenase Involved in Betalain Pigment Biosynthesis in Portulaca grandiflora

The Betalain Secondary Metabolic Network

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