Xanthophyll biosynthesis in chromoplasts: isolation and molecular cloning of an enzyme catalyzing the conversion of 5,6‐epoxycarotenoid into ketocarotenoid

Bouvier, Florence; Hugueney, Philippe; d’Harlingue, Alain; Kuntz, Marcel; Camara, Bilal

doi:10.1046/j.1365-313x.1994.6010045.x

Cited by 186 publications

(134 citation statements)

References 40 publications

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“…29 Capsanthin (1), capsorubin (2), and cryptocapsin (3) are formed by this transformation from antheraxanthin, violaxanthin, and -cryptoxanthin-5,6-epoxide, respectively. …”

Section: Biosynthesismentioning

confidence: 99%

Cryptocapsinepoxide-Type Carotenoids from Red Mamey, Pouteria sapota

et al. 2013

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New carotenoids, cryptocapsin-5,6-epoxide, 3′-deoxycapsanthin-5,6-epoxide, and cryptocapsin-5,8-epoxides, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Cryptocapsin-5,6-epoxide was prepared by partial synthesis via epoxidation of cryptocapsin, and the (5R,6S)- and (5S,6R)-stereoisomers were identified by HPLC-ECD analysis. Spectroscopic data of the natural (anti) and semisynthetic (syn) derivatives obtained by acid-catalyzed rearrangement of cryptocapsin-5,8-epoxide stereoisomers were compared for structural elucidation. Chiral HPLC separation of natural and semisynthetic samples of cryptocapsin-5,8-epoxides was performed, and HPLC-ECD analysis allowed configurational assignment of the separated stereoisomers.

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“…29 Capsanthin (1), capsorubin (2), and cryptocapsin (3) are formed by this transformation from antheraxanthin, violaxanthin, and -cryptoxanthin-5,6-epoxide, respectively. …”

Section: Biosynthesismentioning

confidence: 99%

Cryptocapsinepoxide-Type Carotenoids from Red Mamey, Pouteria sapota

et al. 2013

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“…Unfortunately, the last reaction step resulted in a compound with heterocyclic rings, instead of cycloviolaxanthin. At the same time, cycloviolaxanthin (38) and cucurbitaxanthin B (36) could be isolated in our laboratory from red paprika in very small amounts. …”

Section: -23mentioning

confidence: 77%

“…37 The capsanthin-capsorubin synthase (CCS) enzyme that catalyses the conversion of 5,6-epoxy-end groups into κ-end groups was isolated and characterized in 1994. 38 Certain similarities of CCS were observed with the C. annuum lycopene cyclase, the enzyme catalyzing the cyclization of lycopene. The fact that CCS also exhibits lycopene cyclase activity, is likely to be related to similarities in the chemical mechanisms leading to the formation of β-rings in β-carotene (Scheme 4a) and κ-rings in capsanthin and capsorubin (Scheme 4b).…”

Section: Formation Of the κ-End-groupmentioning

confidence: 96%

Caroteniod 5,6-, 5,8- and 3,6-epoxides

Deli¹,

Ősz²

2004

Arkivoc

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The isolation, semisynthesis and structure elucidation of carotenoid 5,6-, 5,8-and 3,6-epoxides as well as their derivatives are discussed in detail. This review gives a brief summary of the plausible biosynthetic transformations of the 5,6-epoxy-β-ring. A wide variety of carotenoid end-groups can be obtained from 5,6-epoxy carotenoids. In order to get information on the enzyme activities and regulation of the biosynthetic pathway of carotenoids some of the intermediate steps of these transformations were investigated (e.g. formation of allenic, κ-and γ-end-groups as well as ring opening reactions). The ring opening of the 3-hydroxy-5,6-epoxy end group, resulting in the formation of 3,5,6-trihydroxy compounds, was studied in detail in order to obtain evidence for the proposed reaction mechanisms of the two different biosynthetic routes (acid or enzyme catalysis) which also explain the configurations at the C(5) and C(6) atoms.

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“…The change of G to C at position 235 leads to a replacement (denoted as G79R) of glycine G79 with arginine (R) in the protein sequence. This difference is established in the Bulgarian cultivars when compared to the sequence published in PubMed by Bouvier et al [ 9 ].…”

mentioning

confidence: 69%

Molecular Characterization of Advanced Mutants for Early Detection of High β-carotene Concetration in Pepper Breeding Programms

Petrov¹,

Denev²,

Draganov³

et al. 2013

Proceeding BAS

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The Bulgarian orange-fruited mutant cultivar Oranzheva kapiya is characterized with a high content of the antioxidant β-carotene. To identify the mutation leading to the accumulation of β-carotene and develop a suitable molecular marker for this trait, the genes for geranyl-geranyl pyrophosphate synthase, capsanthin-capsorubin synthase and β-carotene hydroxylase were studied both in the mutant and in the parental cultivar -Pazardzhishka kapiya. Our results suggest that the gene for β-carotene hydroxylase in the cv. Oranzheva kapiya is affected by a mutation, as well as the polymorphism between initial and mutant plants in this locus could be used as a molecular marker in the breeding programmes towards high β-carotene content.

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Xanthophyll biosynthesis in chromoplasts: isolation and molecular cloning of an enzyme catalyzing the conversion of 5,6‐epoxycarotenoid into ketocarotenoid

Cited by 186 publications

References 40 publications

Cryptocapsinepoxide-Type Carotenoids from Red Mamey, Pouteria sapota

Cryptocapsinepoxide-Type Carotenoids from Red Mamey, Pouteria sapota

Caroteniod 5,6-, 5,8- and 3,6-epoxides

Molecular Characterization of Advanced Mutants for Early Detection of High β-carotene Concetration in Pepper Breeding Programms

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