Structure of gentiodelphin, an acylated anthocyanin isolated from , that is stable in dilute aqueous solution

Goto, Toshio; Kondo, Tadao; Tamura, Hirotoshi; Imagawa, Hiroyuki; Iino, Aya; Takeda, Kôsaku

doi:10.1016/s0040-4039(00)88660-8

Cited by 120 publications

(53 citation statements)

References 16 publications

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“…Color stabilization mechanisms of anthocyanin have already been proposed such as metal ion complexation (Hayashi et al, 1958), complex foamation of anthocyanins with flavonoid copigments (co-piymentation) (Robinson & Robinson, 1931), self-association (Asen et al, l 977;Hoshino et al, 1982) and intrarnolecular sandwich-type stacking of the anthocyanin nucleus and acyl groups (intramolecular copigmentation) (Saito et al, 1972;Goto et al, 1982;Goto & Kondo, 1988). Tsukui (1988Tsukui ( , 1989 and Tsukui et al (1989) Relationships between anthocyanin stabilities and anthocyanin composition.…”

Section: Discussionmentioning

confidence: 99%

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Stability of Anthocyanins in Various Vegetables and Fruits.

Hayashi¹,

Ohara²,

Tsukui³

1996

FSTI

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Anthocyanins were isolated from 19 kinds of vegetables and fruits. Individual anthocyanins were analyzed by HPLC using a photodiode array detector and were examined for the heating and ultraviolet irradiation stabilities of these anthocyanins. This report deals with the relationship between anthocyanin composition and heating or ultraviolet irradiation stabilities of anthocyanins. Stable anthocyanins showed many anthocyanin peaks and a high ratio of acylated anthocyanin peaks. This result shows that the anthocyanin composition and the rate of acylation affect the stability of anthocyanins.

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Section: Discussionmentioning

confidence: 99%

“…Several theories have been proposed to explain the stabilization mechanism of anthocyanins such as self-assoclation (Asen et al, 1977), copigmentation (Robinson & Robinson,193 l) and intramolecular copigrnentation (Saito et al, 1972; Goto et al, 1982). Anthocyanins are unstable and easily degraded by heat and light, etc.…”

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confidence: 99%

Stability of Anthocyanins in Various Vegetables and Fruits.

Hayashi¹,

Ohara²,

Tsukui³

1996

FSTI

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“…Gentiodelphin is composed of a delphinidin chromophore, three glucoses, and two caffeoyl moieties, and is formally known as Figure 1B (Goto et al 1982). Of the two molecules of caffeic acid, the caffeic moiety at the 3′-position is more important for blue pigmentation (Yoshida et al 2000).…”

Section: The Flavonoid Biosynthetic Pathway In Japanese Gentian Flowersmentioning

confidence: 99%

Transcriptional regulators of flavonoid biosynthesis and their application to flower color modification in Japanese gentians

Nakatsuka

Sasaki

Nishihara

2014

Plant Biotechnology

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Japanese cultivated gentians (Gentiana triflora, G. scabra and their hybrids), some of the most important ornamental flowers in Japan, have vivid blue flowers that accumulate polyacylated anthocyanins such as gentiodelphin. To breed attractive flower colors in Japanese gentians, our research group has been studying the molecular mechanisms that control flower pigmentation. Flavonoids, including anthocyanins, are widely distributed in the plant kingdom and are found in almost all plant organs. Along with longstanding genetic and molecular biological analyses of flavonoid biosynthesis, recent studies have revealed that transcription activators and repressors are involved in sophisticated control of temporal and spatial flavonoid accumulation in various plant organs. In this review, we summarize recent research on the transcriptional regulation of flavonoid biosynthesis in flowers, with a special focus on our findings using Japanese gentians. We also introduce and discuss the potential application of these transcription factor genes as novel tools to engineer flower color intensity and patterns in floricultural plants.

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“…They also exhibit antioxidant activities and therefore may contribute to the prevention of heart disease, cancer, and inflammatory disease (Hou, 2003;Bagchi et al, 2004;Katsube et al, 2003). They are usually localized in the vacuoles of petal epidermal cells (Goto et al, 1982;Tanaka et al, 2004) and are responsible for diverse pigmentation from orange to red, purple and blue in flowers, fruits and vegetables. Often, these compounds also occur in leaves, stems, seeds, and other tissues.…”

Section: Introductionmentioning

confidence: 99%

“…They have also been isolated from Zea mays (Goto et al, 1982), Antirrhinum majus (Martin et al, 1991), Vitis vinifera (Ford et al, 1998), Hordeum vulgare (Wise et al, 1990), Perilla frutescens (Gong et al, 1997) and Fragaria ananassa (Almeida et al, 2007). Many UF3GT genes have been cloned and heterologously expressed, which makes in-depth study of the molecular mechanism controlling anthocyanin biosynthesis possible.…”

Section: Introductionmentioning

confidence: 99%

Molecular cloning and tissue expression analyses of a UF3GT gene from Capsicum annuum L.

Zhou¹,

Deng²,

Wen³

et al. 2013

Afr. J. Agric. Res.

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In the present study, a novel gene designated as UF3GT was isolated from Capsicum annuum L. Sequence and structural analysis determined that the UF3GT protein, which contained 1401 base pairs encodes 447 amino acids and belongs to the Glycosyltransferase-GTB-type superfamily. The isoelectric point and the molecular weight of this gene are 5.97 and 49589, respectively. The deduced amino acid sequence shows highly identity with known anthocyanin synthases in other species. The phylogenetic tree analysis revealed that the C. annuum L. UF3GT has a closer genetic relationship with the UF3GT of petunia (Petunia x hybrida). The RT-PCR gene expression analysis indicated that the UF3GT gene was mostly expressed in pericarp, moderately expressed in stem, leaf, flower, placenta and seed, whereas no expression signal was detected in root. The study established the primary foundation for further research on this C. annuum L. gene.

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Structure of gentiodelphin, an acylated anthocyanin isolated from , that is stable in dilute aqueous solution

Cited by 120 publications

References 16 publications

Stability of Anthocyanins in Various Vegetables and Fruits.

Stability of Anthocyanins in Various Vegetables and Fruits.

Transcriptional regulators of flavonoid biosynthesis and their application to flower color modification in Japanese gentians

Molecular cloning and tissue expression analyses of a UF3GT gene from Capsicum annuum L.

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