著者

Haruka Seto Serina Sasaki Yuko Mitobe Toru Ota Fumi Tatsuzawa

出版者

The Japanese Society for Horticultural Science

雑誌

The Horticulture Journal (ISSN:21890102)

巻号頁・発行日

pp.QH-032, (Released:2023-05-26)

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The flower colors and flavonoids of 16 cultivars of Verbena hybrida Groenl. & Rumpler (Verbenaceae) were examined to evaluate the relationship between flower color and flavonoid components. Fifteen anthocyanins {3-O-glucoside, 3,5-di-O-glucoside, 3-O-[6-O-(acetyl)-glucoside], 3-O-[6-O-(malonyl)-glucoside], and 3,5-di-O-[6-O-(acetyl)-glucoside] of delphinidins, cyanidins, and pelargonidins}, seven flavones {7-O-(glucuronide) of apigenin, luteolin, tricetin, and 4'-O-methyl-luteolin, 7-O-[2-O-(glucuronosyl)-glucuronide]-4'-O-(glucuronide) of apigenin, and 7-O-[2-O-(glucuronosyl)-glucuronide] of apigenin and luteolin}, two flavonols {3-O-glucoside and 3-O-[6-O-(acetyl)-glucoside] of kaempferols}, and chlorogenic acid were isolated from the flowers of these cultivars. Their structures were identified using co-HPLC, nuclear magnetic resonance, and mass spectrometry. For the Red to Purple-Violet cultivars, the corresponding color chart names were responsible for the major anthocyanidin types, and the hue values (b*/a*) of these flower colors reflected the anthocyanins concentration. Based on the relationship between the distribution of flavones, flavonols, and chlorogenic acid among cultivars and flower color, we conclude that flavonoids other than anthocyanins and chlorogenic acid make little contribution to flower color. The yellowish red color is thought to be affected by carotenoids.

著者

Takayuki Mizuno Haruka Seto Takahisa Nakane Yoshinori Murai Fumi Tatsuzawa Tsukasa Iwashina

出版者

National Museum of Nature and Sciece (National Science Museum, Tokyo)

雑誌

国立科学博物館研究報告B類(植物学) (ISSN:18819060)

巻号頁・発行日

vol.49, no.2, pp.57-64, 2023-05-22 (Released:2023-05-22)

参考文献数

25

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One anthocyanin and three flavones were isolated from the flowers of Tripora divaricata (Lamiaceae). They were identified as delphinidin 3-O-[(6″′-E-p-coumaroylglucosyl)-(1→2)-(6″-E-p-coumaroylglucoside)]-5-O-(6″′-malonylglucoside), apigenin 7-O-glucuronide, scutellarein 4′-methyl ether 7-O-glucuronide, and acacetin 7-O-glucuronide. In addition, we measured absorption spectra of intact petal and the buffer solutions (pH 5.6) containing isolated compounds for elucidation of the blue violet color development in T. divaricata. The absorption spectral curve of the buffer solution containing isolated anthocyanin showed the blue violet. Its color was identical to that of the intact flowers. These results indicate that the intramolecular copigmentation of anthocyanin mainly occurred in the blue violet flowers of T. divaricata.

著者

Sho Ohno Mizuki Yokota Haruka Yamada Fumi Tatsuzawa Motoaki Doi

出版者

The Japanese Society for Horticultural Science

雑誌

The Horticulture Journal (ISSN:21890102)

巻号頁・発行日

pp.UTD-305, (Released:2021-08-04)

被引用文献数

7

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Yellow color in dahlia flowers is conferred from chalcones, butein and isoliquiritigenin. The color intensity of yellow dahlia cultivars is diverse, but a detailed study on this has not yet been performed. In this study, we first identified structures of flavonoids by nuclear magnetic resonance imaging in ray florets of the red-white bicolor ‘Shukuhai’, which contains chalcones, flavones and anthocyanins. Four anthocyanins, four flavone derivatives, five isoliquiritigenin derivatives and five butein derivatives were identified. Among the identified compounds, butein 4'-malonylsophoroside is considered to be the final product for butein derivatives and the presence of chalcone 4'-glucosyltransferase, chalcone 4'-glucoside glucosyltransferase, and chalcone 4'-glucoside malonyltransferase for isoliquiritigenin and butein modification was predicted. Also, the biosynthetic pathway of butein and isoliquiritigenin derivatives in dahlia with butein 4'-malonylsophoroside as the final product was predicted from the identified compounds. Next, we used nine yellow cultivars and lines with different color intensities and analyzed the correlation between the b* value, an indicator of yellow color, and level of chalcones. There was no difference in the presence or absence of major peaks among the cultivars and lines. Peak area per fresh weight measured by HPLC was high in butein 4'-malonylglucoside, butein 4'-sophoroside and isoliquiritigenin 4'-malonylglucoside, suggesting these three compounds were accumulated abundantly. Among the identified chalcones, the highest correlation coefficient was detected between the b* value and butein 4'-malonylglucoside (r = 0.86), butein 4'-sophoroside (r = 0.82) or isoliquiritigenin 4'-malonylglucoside (r = 0.76). These results suggest that these three chalcones confer yellow color in dahlia ray florets. The findings in this study will contribute not only to efforts at breeding new yellow dahlia cultivars, but also to molecular breeding of yellow flowers in other species by introducing the butein biosynthetic pathway.

著者

Sho Ohno Wakako Hori Munetaka Hosokawa Fumi Tatsuzawa Motoaki Doi

出版者

一般社団法人 園芸学会

雑誌

The Horticulture Journal (ISSN:21890102)

巻号頁・発行日

pp.OKD-099, (Released:2017-08-04)

被引用文献数

7

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Bicolor flowering dahlias are a group of cultivars that produce inflorescences with bicolored petals characterized by a colored basal part and a white tip. However, they frequently produce single-colored petals, even if they are vegetatively propagated. In a previous study, strong relationships between inflorescence color and leaf phenotype were observed in a red–white bicolor flowering dahlia ‘Yuino’; red petal-producing individuals accumulate flavonoids in leaves, whereas only bicolor petal-producing individuals tend not to accumulate them in leaves. Flavonoids in leaves are assumed to be chalcones. In this study, we investigated flavonoids in the leaves of ‘Yuino’ by nuclear magnetic resonance analysis and identified six caffeoyl esters, four flavonol derivatives, and three novel butein derivatives in the flavonoid-rich leaves of ‘Yuino’. The three novel compounds were butein 4',4-O-di-[2-O-(β-glucopyranosyl)-β-glucopyranoside], butein 4'-O-[2-O-(β-glucopyranosyl)-β-glucopyranoside]-4-O-β-glucopyranoside, and butein 4'-[6-O-(3-hydroxy-3-methylglutaryl)-β-glucopyranoside]-4-O-β-glucopyranoside. On the other hand, only caffeoyl esters were detected in flavonoid-poor leaves. These data demonstrated that flavonoid-rich leaves accumulated the flavonoids of butein and flavonol derivatives. The common enzyme for the biosynthesis of butein and flavonol derivatives is chalcone synthase; thus, the importance of chalcone synthase for phenotypic lability in ‘Yuino’ was confirmed.

著者

Ayumi Deguchi Fumi Tatsuzawa Munetaka Hosokawa Motoaki Doi Sho Ohno

出版者

一般社団法人 園芸学会

雑誌

The Horticulture Journal (ISSN:21890102)

巻号頁・発行日

pp.MI-121, (Released:2016-02-04)

被引用文献数

14

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The black flower color of dahlias (Dahlia variabilis) has been suggested to be attributed to a high accumulation of cyanidin (Cy)-based anthocyanins. A possible explanation for this effect is that Cy-based anthocyanins in dahlias contribute more to the black flower color than pelargonidin (Pg)-based anthocyanins by lowering petal lightness (L*) and chroma (C*), but no obvious evidence has been reported. In this study, four major anthocyanins accumulated in dahlia petals, 3,5-diglucoside (3,5diG) and 3-(6''-malonylglucoside)-5-glucoside (3MG5G) of Pg and Cy, were purified and their colors were evaluated in vitro at various pHs (3.0, 4.0, 4.5, 5.0, 5.5, 6.0, or 7.0) and various concentrations (0.25, 0.5, 1.0, 2.0, or 3.0 mg·mL−1 at pH 5.0 or pH 3.0). The color of solution of purified anthocyanins varied depending on pH. At pH 5.0, which is approximately the same as pH of dahlia petals, and at pH 3.0, at which anthocyanins are relatively stable, the L* and C* of Cy 3,5diG were similar to or higher than those of Pg 3,5diG, suggesting that Cy 3,5diG did not contribute more to the black flower coloring than Pg 3,5diG. On the other hand, the L* and C* of Cy 3MG5G were significantly lower than those of Pg 3MG5G, particularly above 2.0 mg·mL−1, suggesting that Cy 3MG5G contributed more than Pg 3MG5G. A similar tendency was observed in the color measurement of mixed anthocyanins in various proportion of Pg and Cy. The L* and C* of Pg 3MG5G were much higher than those of the other three anthocyanins; therefore, its color was considered to be the farthest from black among the four anthocyanins. The accumulated amount of 3MG5G-type anthocyanins was much higher than that of 3,5diG-type anthocyanins in all nine cultivars, although the proportion of Pg- and Cy-based anthocyanins varied among the cultivars. Considering these results, it was suggested that because 3MG5G-type anthocyanins predominantly accumulate in petals, and Cy 3MG5G has a significantly higher contribution to lowering L* and C* than Pg 3MG5G, the high accumulation of Cy-based anthocyanins is critical for the black flower coloring of dahlias. The contribution of each anthocyanin is considered to depend on the structure; therefore, identifying the anthocyanin with the highest contribution to lowering L* and C* may enable the production of black flowers in various species through the high accumulation of the anthocyanin in petals.

著者

Fumi Tatsuzawa Kenjiro Toki Yuko Ohtani Kazuhisa Kato Norio Saito Toshio Honda Masahiro Mii

出版者

園芸学会

雑誌

Journal of the Japanese Society for Horticultural Science (ISSN:18823351)

巻号頁・発行日

pp.CH-100, (Released:2014-04-26)

被引用文献数

2 7

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Two anthocyanins (pigments 1 and 2) were detected from the blue flowers of Nemophila menziesii ‘Insignis blue’ and the purple flowers of its variants as the main floral anthocyanins. These two anthocyanins were isolated from the blue flowers and elucidated to be petunidin 3-O-[6-O-(cis-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] (1) and petunidin 3-O-[6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside] (2), respectively, by chemical and spectroscopic means, and pigment 1 was confirmed as a new anthocyanin in plants. Two flavonol glycosides (pigments 3 and 5) and two flavone glycosides (pigments 4 and 6) were also isolated from the blue flowers, and were identified to be kaempferol 3-(6-rhamnosyl)-glucoside-7-glucoside (3), apigenin 7,4′-di-glucoside (4), kaempferol 3-(2,6-di-rhamnosyl)-glucoside (5), and apigenin 7-glucoside-4′-(6-malonyl)-glucoside (6) as major flavonoids. Among these four flavonoids, however, pigments 4 and 6 (flavones) were not detected in the purple flowers. These results might be attributed to color production in blue and purple flowers.

著者

Natsu Tanikawa Hiroyuki Sano Fumi Tatsuzawa

出版者

The Japanese Society for Horticultural Science

雑誌

The Horticulture Journal (ISSN:21890102)

巻号頁・発行日

pp.QH-067, (Released:2023-06-14)

被引用文献数

1

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We investigated bluish-purple Platycodon grandiflorus flowers for yet unidentified flavonoid-related compounds and their flower coloration mechanisms. We identified a new polyacylated anthocyanin, delphinidin 3-O-[6-O-(α-rhamnopyranosyl)-β-glucopyranoside]-7-O-[6-O-(4-O-(6-O-(4-O-(6-O-(4-O-(β-glucopyranosyl)-trans-caffeoyl)-β-glucopyranosyl)-trans-caffeoyl)-β-glucopyranosyl)-trans-caffeoyl)-β-glucopyranoside] (3) as the minor anthocyanin component along with four known anthocyanins, four known flavones, and chlorogenic acid. The major anthocyanin of the bluish-purple P. grandiflorus flowers is platyconin. While platyconin has two caffeic acids linked in series via glucose molecules at the 7-position of delphinidin, anthocyanin 3 has three caffeic acids linked in series via glucose molecules at the 7-position of delphinidin. To investigate the effects of the number of aromatic acyl groups in polyacylated anthocyanin on bluing and stability, the color and stability of anthocyanin 3 in diluted aqueous solution (5 × 10−5 M) at a weak acidic condition (pH 5.7, the same pH as the petal sap) were compared with those of platyconin. Results showed that even if the three caffeic acids were bound in series at the 7-position of delphinidin, there was no further bluing or stabilizing effects of anthocyanin 3 compared to platyconin, but a tendency toward weakening color intensity was observed. Investigation of the change in anthocyanin content at the flower developmental stages showed that delphinidin 3-rutinoside-7-glucoside, which is the deacylated form of platyconin, first accumulated up to sufficient amounts at the bud stage, followed by an increase in platyconin content. At the bud stage, the petals were not purple or violet, except for veins, despite the presence of a good amount of delphinidin 3-rutinoside-7-glucoside, indicating the delphinidin 3-rutinoside-7-glucoside was present in some colorless state.

著者

Takanori Masukawa Masayuki Kadowaki Toshikazu Matsumoto Akira Nakatsuka Kyeong-Seong Cheon Kazuhisa Kato Fumi Tatsuzawa Nobuo Kobayashi

出版者

The Japanese Society for Horticultural Science

雑誌

The Horticulture Journal (ISSN:21890102)

巻号頁・発行日

pp.OKD-132, (Released:2018-01-06)

被引用文献数

2

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Purple and red colored root characteristics were introduced to a local pungent radish “Izumo orochi daikon” ‘Susanoo’, and several characteristics including food functional components were evaluated. The root and leaf phenotype, the pigment composition, the isothiocyanate and soluble solids contents, and the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity in the root were investigated. These characteristics were compared between the mass selection breeding lines of purple, red roots and their parent cultivars. Although one-third of individuals in the M6 and M7 were non colored, the colored root characteristics was introduced into ‘Susanoo’. The main anthocyanins in the deep reddish purple colored purple root lines were acylated cyanidin 3-sophoroside-5-glucosides, and those in the vivid purplish red colored red root lines were acylated pelargonidin 3-sophoroside-5-glucosides, which corresponded to the main anthocyanins in their respective colored root parental cultivars. The isothiocyanate contents in the purple and red root lines were almost the same as that in ‘Susanoo’. The DPPH radical scavenging activity of the purple and red root lines was almost two times higher than that of ‘Susanoo’. These results showed that the food functionality was enhanced by introduction of a colored root characteristic in ‘Susanoo’.