Skip to main contentSkip to article Phytochemistry Volume 159, March 2019, Pages 108-118 Acylated pelargonidin glycosides from the red-purple flowers of Iberis umbellata L. and the red flowers of Erysimum × cheiri (L.) Crantz (Brassicaceae) Author links open overlay panelFumi Tatsuzawa Show more Share Cite https://doi.org/10.1016/j.phytochem.2018.12.010 Get rights and content Abstract Five previously undescribed acylated pelargonidin 3-sophoroside-5-glucosides (pigments 2–6) were isolated from the red-purple flowers of Iberis umbellata L. ‘Candycane Rose’ and ‘Candycane Red’, in addition to a known one (pigment 1). The structures of five undescribed acylated anthocyanins were determined by chemical and spectroscopic methods to be pelargonidin 3-O-[2-O-(2-O-(“acyl-A”)-β-glucopyranosyl)-6-O-(“acyl-B”)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside], in which the “acyl-A” group was either trans-sinapic (2), trans-ferulic (3), trans-sinapic (4), trans-ferulic (5), or trans-ferulic acid (6), and “acyl-B” was either glucosyl-trans-p-coumaric acid (2), glucosyl-trans-p-coumaric acid (3), trans-feruloyl-glucosyl-trans-p-coumaric acid (4), trans-feruloyl-glucosyl-trans-p-coumaric acid (5), or glucosyl-trans-feruloyl-glucosyl-trans-p-coumaric acid (6). Moreover, three previously undescribed acylated pelargonidin 3-sambubioside-5-glucosides (pigments 7, 8, and 10) and one undescribed acylated pelargonidin 3-(3X-glucosylsambubioside)-5-glucoside (pigment 9) were isolated from the red flowers of Erysimum × cheiri (L.) Crantz ‘Aurora’ as major anthocyanins. The structures of the three undescribed acylated pelargonidin 3-sambubioside-5-glucosides were determined to be pelargonidin 3-O-[2-O-(2-O-(“acyl-C”)-β-xylopyranosyl)-6-O-(“acyl-D”)-β-glucopyranoside]-5-O-(β-glucopyranoside), in which the “acyl-C” group was either non (7), non (8), or trans-p-coumaric acid (10) and “acyl-D” was either trans-p-coumaric (7), trans-ferulic (8), or trans-p-coumaric acid (10). Moreover, a previously undescribed acylated pelargonidin 3-(3X-glucosylsambubioside)-5-glucoside was identified to be pelargonidin 3-O-[2-O-(2-O-(trans-p-coumaroyl)-3-O-(β-glucopyranosyl)-β-xylopyranosyl)-6-O-(trans-p-coumaroyl)-β-glucopyranoside]-5-O-(β-glucopyranoside) (9). In addition, the distribution of anthocyanidins structural elements in 24 Brassicaceous species is compared. Graphical abstract Nine undescribed acylated pelargonidin glycosides together with one known one were isolated from the flowers of Iberis umbellata and Erysimum × cheiri. Download : Download high-res image (494KB) Download : Download full-size image Introduction Iberis umbellata L. (Brassicaceae), the common candytuft, is an annual flowering plant species, native to southern Europe that usually is cultivated as a popular annual garden plant with white, pink, red, purple, or purple-violet flowers. Erysimum × cheiri (L.) Crantz (Brassicaceae), the common wallflower, is a perennial subshrub species, native to southern Europe that usually is cultivated as a popular biennial garden plant with yellow, orange, red, or red-purple flowers. As part of the ongoing work on flower and/or root color variation due to acylated anthocyanins in olericultural and floricultural plants in the Brassicaceae, I and my co-workers previously reported the isolation of 75 acylated anthocyanins from the flowers of plants in the family Brassicaceae, including 11 acylated cyanidin 3-sophoroside-5-glucosides in the purple-violet flowers of I. umbellata cultivars and two acylated cyanidin 3-sambubioside-5-glucosides in the red and orange-red flowers of E. × cheiri cultivars (Honda et al., 2005; Ito et al., 2013; Saito et al., 1995, 1996, 2008, 2011; Tatsuzawa, 2012, 2014a, b, 2016; Tatsuzawa et al., 2006, 2007, 2008a, b, 2010a, 2012a, b, c, 2013, 2014, 2015a, b, 2016, 2018). Sophorose is a disaccharide composed of two glucopyranose residues, with the glucoside attached in β configuration at the 2 position of the reducing glucose. A sophoroside means this sugar attached with a glycosidic bond in β configuration, i.e. 2-O-β-glucopyranosyl-β-glucopyranoside. Sambubiose is a quite similar disaccharide but with the outermost glucoside replaced by a xyloside, i.e. 2-O-β-xylopyranosyl-β-glucopyranoside. In essence, a sambubioside lacks the hydroxymethyl group of C6 in glucose, but is otherwise identical to a sophoroside. Herein, I report the structural elucidation of 9 undescribed acylated pelargonidin glycosides, along with a known one, from the red-purple flowers of I. umbellata ‘Candycane Red’ and ‘Candycane Rose’ and the red flowers of E. × cheiri ‘Aurora’. Section snippets Anthocyanins in the red-purple flowers of I. umbellata By HPLC analysis of an extract from the red-purple flowers of Iberis umbellata, I identified more than 20 anthocyanin peaks. Among these peaks, six major anthocyanin peaks were isolated from the flowers of ‘Candycane Red’ (Fig. 1) and ‘Candycane Rose’ by extraction by 5% HOAc, and purified according to the procedure described previously (Saito et al., 2008). The same six pigments were found in both cultivars, but the profiles differed slightly. Percentages of total anthocyanin contents based on Discussion Anthocyanins in the form of acylated cyanidin glycosides have been isolated previously from the flowers of Iberis and Erysimum cultivars (Saito et al., 2008; Tatsuzawa et al., 2006, 2016). In the present study, six acylated pelargonidin 3-sophoroside-5-glucosides and four acylated pelargonidin 3-sambubioside-5-glucosides (including 3-(3X-glucosylsambubioside)-5-glucoside) were isolated from the red-purple flowers of I. umbellata cultivars and the red flowers of E. × cheiri cultivars. The genera General procedures Thin layer chromatography (TLC) was conducted on cellulose-coated plastic sheets (Merck, Darmstadt, Germany) using five mobile phases: BAW (n-BuOH/HOAc/H2O. 4:1:2, v/v/v), BuHCl (n-BuOH/2N HCl, 1:1, v/v, upper layer), AHW (HOAc/HCl/H2O, 15:3:82, v/v/v), 1% HCl for anthocyanins and organic acid, and BAW and ETN (EtOH/NH4OH/H2O, 16:1:3, v/v/v) for sugars with detection using UV light and the aniline hydrogen phthalate spray reagent (Harborne, 1984). Analytical high performance liquid References (51) S.J. Bloor et al. The structure of the major anthocyanin in Arabidopsis thaliana Phytochemistry (2002) J.B. Harborne Plant polyphenols – XI. The structure of acylated anthocyanins Phytochemistry (1964) T. Honda et al. Acylated anthocyanins from the violet-blue flowers of Orychophragmus violaceus Phytochemistry (2005) G. Hrazdina et al. Anthocyanins composition of Brassica oleracea cv. Red Danish Phytochemistry (1977) S. Ito et al. Acylated cyanidin 3-sambubioside-5-glucosides in the red-purple flowers of Arabis blepharophylla Hook. & Arn. (Brassicaceae) Biochem. Syst. Ecol. (2013) R. Nakabayashi et al. Metabolomics-oriented isolated and structure elucidation of 37 compounds including two anthocyanins from Arabidopsis thaliana Phytochemistry (2009) T. Otsuki et al. Acylated anthocyanins from red radish (Raphanus sativus L.) Phytochemistry (2002) N. Saito et al. Acylated cyanidin 3-sambubioside-5-glucoside in Matthiola incana Phytochemistry (1995) N. Saito et al. Acylated pelargonidin 3-sambubioside-5-glucosides in Matthiola incana Phytochemistry (1996) N. Saito et al. Tetra-acylated cyanidin 3-sophoroside-5-glucosides from the flowers of Iberis umbellata L. (Cruciferae) Phytochemistry (2008) View more references Cited by (3) Anthocyanins and anthocyanidins in the flowers of Aconitum (Ranunculaceae) 2019, Biochemical Systematics and Ecology Citation Excerpt : These two major pigments were extracted from the dried sepals of the combined taxa (IUM 19375, 19380, and 19381) with violet and violet-blue flowers (500 g) using 20% HOAc (5 L). The extract was isolated and purified using Diaion HP-20 (Nippon Rensui Co. Ltd., Tokyo, Japan) and Sephadex™ LH-20 (GE Halthcare UK Ltd., UK) column chromatography, preparative HPLC, and paper chromatography as described previously (Tatsuzawa, 2019) and yielded 26 mg of pigment 1 and 3 mg of pigment 2. Acid hydrolysis of pigment 1 (0.5 mg) and 2 (0.5 mg) produced delphinidin (tR: 20.3 min) and p-hydroxybenzoic acid (tR: 7.6 min). 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