A malonylated anthocyanin and flavonols in blue Meconopsis flowers

Tanaka, Masayasu; Fujimori, Takahiro; Uchida, Ikuo; Yamaguchi, Shin; Takeda, Kôsaku

doi:10.1016/s0031-9422(00)00357-5

Cited by 41 publications

(19 citation statements)

References 10 publications

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“…Anthocyanins accumulate as simple 3,5-diglucosides that are neither acylated with malonyl-nor with aromatic caffeoyl-or coumaroyl-groups. This disfavours blue colour formation because acylation with especially aromatic groups is a characteristic of many blue flowered plants (Saito et al, 1995;Norbaek and Kondo, 1998;Bloor and Falshaw, 2000;Suzuki et al, 2000;Bloor, 2001;Suzuki et al, 2001;Tanaka et al, 2001;Norbaek et al, 2002b;Williams et al, 2002;Kazuma et al, 2003). Introduction of relevant acyl transferases in K. blossfeldiana would therefore be an interesting approach towards Kalanchoë flowers with bluish colours.…”

Section: Resultsmentioning

confidence: 99%

Flavonoids in flowers of 16 Kalanchoë blossfeldiana varieties

Nielsen¹,

Olsen²,

Møller³

2005

Phytochemistry

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Section: Resultsmentioning

confidence: 99%

Flavonoids in flowers of 16 Kalanchoë blossfeldiana varieties

Nielsen¹,

Olsen²,

Møller³

2005

Phytochemistry

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“…38,39 Detailed chemical structures of the former were determined by X-ray crystallographic analysis as commelinin 28,29 from dayflower and protocyanin from cornflower. 33 In metalloanthocyanins, the metal ions coordinate only to di-OH groups at the B-ring of the anthocyanidin chromophore, not to the copigments.…”

Section: ■ Introductionmentioning

confidence: 99%

Metal Complex Pigment Involved in the Blue Sepal Color Development of Hydrangea

Oyama

Yamada

Ito

et al. 2015

J. Agric. Food Chem.

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Anthocyanins exhibit various vivid colors from red through purple to blue and are potential sources of food colorants. However, their usage is restricted because of their instability, especially as a blue colorant. The blue sepal color of Hydrangea macrophylla is due to a metal complex named "hydrangea-blue complex" composed of delphinidin 3-O-glucoside, 1, 5-O-caffeoylquinic acid, 2, and/or 5-O-p-coumaroylquinic acid, 3, as copigments, and Al(3+) in aqueous solution at approximately pH 4.0. However, the ratio of each component ins not stoichiometric, but is fluctuates within a certain range. The hydrangea-blue complex exists only in aqueous solution, exhibiting a stable blue color, but attempts at crystallization have failed; therefore, the structure remains obscure. To clarify the basis of the character of the hydrangea-blue pigment and to obtain its structural information, we studied the mixing conditions to reconstruct the same blue color as observed in the sepals. In highly concentrated sodium acetate buffer (6 M, pH 4.0) we could measure (1)H NMR of both the hydrangea-blue complex composed of 1 (5 mM), 2 (10 mM), and Al(3+) (10 mM) and a simple 1-Al(3+) complex. We also recorded the spectra of complexes composed with structurally different anthocyanins and copigments. Comparison of those signals indicated that in the hydrangea-blue complex 1 might be under equilibrium between chelating and nonchelating structures having an interaction with 2.

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“…Theoretically, a transition from delphinidin to cyanidin, via inactivation of the F3 ′ 5 ′ H gene, represents a potential mechanism underlying color shift from bluer to redder flowers in the genus Meconopsis . However, this hypothesis is not supported by previous findings, which showed a lack of delphinidin‐based anthocyanins in the blue flowers of M. grandis , in which cyanidin was the only anthocyanin identified (Takeda et al, ; Tanaka et al, ). Therefore, it is likely that transitions from bluer to redder flowers in Meconopsis are not derived from an on/off switching of the ABP branches.…”

Section: Discussionmentioning

confidence: 64%

Mechanisms underlying flower color variation in Asian species ofMeconopsis: A preliminary phylogenetic analysis based on chloroplast DNA and anthocyanin biosynthesis genes

Zhao

Wang

Fang

2014

J of Sytematics Evolution

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The Qinghai-Tibet Plateau (QTP) harbors the highest species diversity of alpine plants in the world, with a spectacular diversity of flower colors. Among these QTP plants, the genus Meconopsis comprises more than 50 species, for which flower color is a key diagnostic character. However, the mechanisms underlying flower color variation have rarely been investigated. In the present study, we used three chloroplast (cp) DNA fragments and two anthocyanin biosynthesis genes (F3H and F3 0 H) for phylogenetic reconstruction of Meconopsis. We revealed the presence of three well-supported clades and/or subclades in the cpDNA and nuclear gene trees; further, flower color transition occurred in each lineage. The results of selection tests and preliminary expression analyses of the anthocyanin biosynthesis genes indicate that the pigment pathway leading to cyanidin is active in blue and red flowers of Meconopsis; further, a blue-red color shift is not attributable to an on/off switching of the anthocyanin biosynthetic pathway (ABP) branches. Together with the results of previous flower pigment analyses, our findings suggest that blue-red flower color transitions in Meconopsis are attributable to modification of cyanidin. Our molecular dating results indicate that the lineage diversification in Meconopsis is closely related to the QTP uplift; thus, it is likely that environmental changes arising from the QTP uplift have played important roles in driving the diversification of flavonoids, through which species of Meconopsis have adapted physiologically to diverse habitats.

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A malonylated anthocyanin and flavonols in blue Meconopsis flowers

Cited by 41 publications

References 10 publications

Flavonoids in flowers of 16 Kalanchoë blossfeldiana varieties

Flavonoids in flowers of 16 Kalanchoë blossfeldiana varieties

Metal Complex Pigment Involved in the Blue Sepal Color Development of Hydrangea

Mechanisms underlying flower color variation in Asian species ofMeconopsis: A preliminary phylogenetic analysis based on chloroplast DNA and anthocyanin biosynthesis genes

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