Acylated Cyanidin 3-sophoroside-5-glucosides from the Purple Roots of Red Radish (Raphanus sativus L.) ‘Benikanmi’

Tatsuzawa, Fumi; Saitô, Norio; Toki, Kenjiro; Shinoda, Koichi; Shigihara, Atsushi; Honda, Toshio

doi:10.2503/jjshs1.79.103

Cited by 27 publications

(27 citation statements)

References 17 publications

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“…The quantification of anthocyanins including pelargonidin, cyanidin, and delphinidin was investigated by Hanlon and Barnes [4], and many research groups [12,53] also found that the major anthocyanins in radish sprouts are acylated pelargonidins, such as in the Daikon cultivar [54], while other researchers showed that cyanidin-based pigments could be isolated from red radish ( R. sativus L. var. Benikanmi) [55], radish cultivar Sango sprouts [56], and Purple Bordeaux radish [57]. However, other studies have shown that glucoraphasatin purified from radish sprouts has some antioxidant capacity [58], which contributed to the total antioxidant capacity of radish sprout extract [59].…”

Section: Resultsmentioning

confidence: 99%

Metabolic Profiling and Antioxidant Assay of Metabolites from Three Radish Cultivars (Raphanus sativus)

et al. 2016

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A total of 13 anthocyanins and 33 metabolites; including organic acids, phenolic acids, amino acids, organic compounds, sugar acids, sugar alcohols, and sugars, were profiled in three radish cultivars by using high-performance liquid chromatography (HPLC) and gas chromatography time-of-flight mass spectrometry (GC-TOFMS)-based metabolite profiling. Total phenolics and flavonoids and their in vitro antioxidant activities were assessed. Pelargonidins were found to be the major anthocyanin in the cultivars studied. The cultivar Man Tang Hong showed the highest level of anthocyanins (1.89˘0.07 mg/g), phenolics (0.0664˘0.0033 mg/g) and flavonoids (0.0096˘0.0004 mg/g). Here; the variation of secondary metabolites in the radishes is described, as well as their association with primary metabolites. The low-molecular-weight hydrophilic metabolite profiles were subjected to principal component analysis (PCA), hierarchical clustering analysis (HCA), Pearson's correlation analysis. PCA fully distinguished the three radish cultivars tested. The polar metabolites were strongly correlated between metabolites that participate in the TCA cycle. The chemometrics results revealed that TCA cycle intermediates and free phenolic acids as well as anthocyanins were higher in the cultivar Man Tang Hong than in the others. Furthermore; superoxide radical scavenging activities and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging were investigated to elucidate the antioxidant activity of secondary metabolites in the cultivars. Man Tang Hong showed the highest superoxide radical scavenging activity (68.87%) at 1000 µg/mL, and DPPH activity (20.78%), followed by Seo Ho and then Hong Feng No. 1. The results demonstrate that GC-TOFMS-based metabolite profiling, integrated with chemometrics, is an applicable method for distinguishing phenotypic variation and determining biochemical reactions connecting primary and secondary metabolism. Therefore; this study might provide information on the relationship between primary and secondary metabolites and a synergistic antioxidant ability derived from the secondary metabolites in the radish cultivars.

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Section: Resultsmentioning

confidence: 99%

Metabolic Profiling and Antioxidant Assay of Metabolites from Three Radish Cultivars (Raphanus sativus)

et al. 2016

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“…By application of its NOESY experiment, NOEs between H-1 of Glc A and H-4 ( H 8.77) of cyanidin, H-1 of Glc B and H-6 ( H 6.93) of cyanidin, and H-2 ( H 4.12) of Glc A and H-1 of Glc C were observed (Figure 1), supporting glycosylation of the C-3 and C-5 cyanidin hydroxyl groups with Glc A and Glc B, respectively, while also indicating a sophorose structure between Glc A and Glc C. , which is a new anthocyanin in plants [5][6][7][8][9][10][11][12][13][14][15][16][17]. This structure was also confirmed by analysis of its 13 C, 1 H- 13 C HMQC and 1 H-13 C HMBC NMR spectra.…”

Section: Pigmentmentioning

confidence: 86%

Acylated Cyanidin 3-sophoroside-5-glucoside in Purple-violet Flowers of Moricandia arvensis (Brassicaceae)

Tatsuzawa

Kato

Sato

et al. 2015

Natural Product Communications

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A new acylated anthocyanin was isolated as a major pigment, along with a known anthocyanin (Moricandia arvensis anthocyanin 1: MAA-1), from a strain of Moricandia arvensis (Code No. MOR-ARV-3) with purple-violet flowers, and identified as cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(-glucopyranosyl)trans-caffeoyl)--glucopyranosyl)-trans-caffeoyl)--glucopyranosyl)-6-O-(trans-sinapoyl)--glucopyranoside]-5-O-[6-O-(malonyl)--glucopyranoside].

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“…Hanlon and Barnes (2011) showed a quantification of anthocyanins by classes (pelargonidin, cyanidin and (7) 271 (8) 1035 991 (7) 787 (43) 535 (100) 491 (10) 287 (11) 287 (100) (Giusti & Wrolstad, 2003;Park et al, 2013;Wu & Prior, 2005) also found that the major anthocyanins in radish sprouts are acylated pelargonidins, such as Daikon cultivar (De Nicola et al, 2013), while others reported the isolation of cyanidin-based pigments in red radish (R. sativus L. var. Benikanmi) (Tatsuzawa et al, 2010), Purple Bordeaux radish (Lin, Sun, Chen, & Harnly, 2011) and radish cv. Sango sprouts (Matera et al, 2012).…”

Section: Qualitative and Quantitative Analysis Of Anthocyaninsmentioning

confidence: 99%

Radish sprouts—Characterization and elicitation of novel varieties rich in anthocyanins

Baenas

Ferreres

García‐Viguera

et al. 2015

Food Research International

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Acylated Cyanidin 3-sophoroside-5-glucosides from the Purple Roots of Red Radish (Raphanus sativus L.) ‘Benikanmi’

Cited by 27 publications

References 17 publications

Metabolic Profiling and Antioxidant Assay of Metabolites from Three Radish Cultivars (Raphanus sativus)

Metabolic Profiling and Antioxidant Assay of Metabolites from Three Radish Cultivars (Raphanus sativus)

Acylated Cyanidin 3-sophoroside-5-glucoside in Purple-violet Flowers of Moricandia arvensis (Brassicaceae)

Radish sprouts—Characterization and elicitation of novel varieties rich in anthocyanins

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