Acylated Cyanidin 3,7-Diglucosides in the Red-purple Flowers of Sophronitis wittigiana (Orchidaceae)

Tatsuzawa, Fumi; Saitô, Norio; Yukawa, Tomohisa; Honda, Toshio; Shinoda, Koichi; Kato, Kazuhisa; Miyoshi, K.

doi:10.2503/jjshs1.ch-084

Cited by 11 publications

(3 citation statements)

References 27 publications

(34 reference statements)

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“…Whereas 3,5-diglucosides are widely found in plant materials, 3,7-diglucosides have a more restrictive substitution pattern . As far as we know, 3,7-diglucosides have been identified only in some flowers but not in fruits and berries, and they include the following structures: the nonacylated 3,7-diglucosides of cyanidin, delphinidin, and petunidin, and the (poly)acylated 3,7-diglucosides and 3,7-diglycosides of pelargonidin, cyanidin, delphinidin, petunidin, and malvidin. − Our group recently demonstrated the occurrence of peonidin 3,7-diglucoside as a very minor anthocyanin in Garnacha Tintorera grape and wine samples . Therefore, compound 5 (malvidin 3,7-diglucoside) was never reported in plant materials.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Structural Elucidation of Anthocyanidin 3,7-β-O-Diglucosides and Caffeoyl-glucaric Acids from Calafate Berries

Ruíz

Mardones

Vergara

et al. 2014

J. Agric. Food Chem.

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Calafate (Berberis microphylla G. Forst) is an edible wild berry growing in South Patagonia that is very rich in anthocyanins and hydroxycinnamic acid derivatives. Calafate contains unusual phenolic compounds compared to other berries, such as anthocyanidin dihexosides, different from the common 3,5-diglucosides, and isomeric esters of caffeic acid with hexaric acids. After isolation, their structures have been elucidated by UV-vis, MS/MS, and NMR spectroscopies. The anthocyanidin dihexosides constitute the complete series of 3,7-β-O-diglucosides of the five anthocyanidins usually found in calafate, the structures of which were completely elucidated in the cases of delphinidin, petunidin, and malvidin derivatives and tentatively suggested in the cases of cyanidin and peonidin, and their occurrence seems to be characteristic of calafate among other wild berries from South Patagonia. With regard to caffeoyl-hexaric acids, two of four isomers have been assigned as 3- and 4-trans-caffeoyl-glucaric acids, but the determination of the linkage position for each isomer was not possible. A third isomer was also isolated, but it easily degraded and was suggested to be the 2- or 5-trans-caffeoyl-glucaric acid. The caffeoyl-glucaric acids account for around half of the pool of hydroxycinnamic acid derivatives in calafate.

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Section: Resultsmentioning

confidence: 99%

Isolation and Structural Elucidation of Anthocyanidin 3,7-β-O-Diglucosides and Caffeoyl-glucaric Acids from Calafate Berries

Ruíz

Mardones

Vergara

et al. 2014

J. Agric. Food Chem.

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“…Sophoronitis spp. (Orchidaceae) (red-purple, orange-red and red) Anthocyanins: [15] Sophoronitis coccinea (Orchidaceae) (orange-red) [17] Vanda spp. and cultivars (Orchidaceae) (red-purple, purple-violet, violet and violetblue) Anthocyanins: [45] Verbena hybrida cultivars (Verbenaceae) (scarlet) Anthocyanin: Pelargonidin 3-O-(6´´-malonylglucoside) [21a] Verbena hybrida cultivars (deep pink) Anthocyanins:…”

Section: Warm Flower Colors Such As Pink Scarlet Red Red-purple Amentioning

confidence: 99%

“…and cultivars [13], Bletilla striata [14], Sophoronitis spp. [15,17], Dendrobium cultivars [16a], Cheiranthes cheiri and Lunaria annua [18] in the Brassicaceae are also due to cyanidin glycosides. However, their anthocyanins are complicatedly glycosylated and acylated, and may influence the flower colors by intra-molecular copigmentation.…”

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confidence: 99%

Contribution to Flower Colors of Flavonoids Including Anthocyanins: A Review

Iwashina

2015

Natural Product Communications

114

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Flavonoids are one of the major pigments in higher plants, together with chlorophylls and carotenoids. Though ca. 8,000 kinds of flavonoids have been reported in nature, anthocyanins, chalcones, aurones and some flavonols act as major flower pigments. Flavonoids are present as major components in many flowers. On the other hand, flavones and flavonols, which are colorless or extremely pale yellow, function as copigment substances. Moreover, expression of the flower colors is diversified by inter-molecular and intra-molecular copigmentation, metal chelation, pH change and so on. In this review, I describe the distribution of the flavonoids which act as the pigments, and contribution to flower colors, e.g., yellow, scarlet, red, red-purple, violet, purple, blue and so on, of flavonoids, especially anthocyanins, chalcones, aurones and flavonols.

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Anthocyanins: a comprehensive review on biosynthesis, structural diversity, and industrial applications

Sendri,

Bhandari

2024

Phytochem Rev

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Acylated Cyanidin 3,7-Diglucosides in the Red-purple Flowers of Sophronitis wittigiana (Orchidaceae)

Abstract: Three new acylated cyanidin 3,7-diglucosides (1-3) were isolated from the red-purple flowers of Sophronitis wittigiana as its main floral anthocyanins. These three pigments were based on cyanidin 3,7-diglucoside as the deacylanthocyanin, and their structures were determined to be cyanidin

Cited by 11 publications

References 27 publications

Isolation and Structural Elucidation of Anthocyanidin 3,7-β-O-Diglucosides and Caffeoyl-glucaric Acids from Calafate Berries

Isolation and Structural Elucidation of Anthocyanidin 3,7-β-O-Diglucosides and Caffeoyl-glucaric Acids from Calafate Berries

Contribution to Flower Colors of Flavonoids Including Anthocyanins: A Review

Anthocyanins: a comprehensive review on biosynthesis, structural diversity, and industrial applications

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