The flavonoid 5-glucosides, quercetin 5,4'-di-O-beta-D-glucopyranoside and quercetin 5,7,4'-tri-O-beta-D-glucopyranoside, together with the known quercetin 5-O-beta-D-glucopyranoside, were isolated from the cocoon shell of the silkworm, Bombyx mori. The structures were identified by spectroscopic analysis. These flavonoid glucosides were not present in mulberry leaves, the silkworm's only food, and they are considered to be metabolites produced by the silkworm.
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Acylated pelargonidin glycosides from the red-purple flowers of Iberis umbellata L. and the red flowers of Erysimum × cheiri (L.) Crantz (Brassicaceae).
Phytochemistry
March 2019
Faculty of Agriculture, Iwate University, Morioka 020-8550, Japan. Electronic address:
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).
View Article and Find Full Text PDFTriacylated peonidin 3-sophoroside-5-glucosides from the purple flowers of Moricandia ramburii Webb.
Phytochemistry
April 2012
Faculty of Agriculture, Iwate University, Morioka, Iwate, Japan.
Triacylated peonidin 3-sophoroside-5-glucosides were isolated from the purple flowers of Moricandia ramburii Webb. (Family: Brassicaceae), and determined to be peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (1), peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(cis-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (2) and peonidin 3-O-[2-O-(2-O-(trans-sinapoyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (3), respectively, by chemical and spectroscopic methods. In addition, one known acylated cyanidin glycoside, cyanidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(trans-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] (4), was also identified in the flowers.
View Article and Find Full Text PDFUHPLC-PDA-ESI/HRMS/MS(n) analysis of anthocyanins, flavonol glycosides, and hydroxycinnamic acid derivatives in red mustard greens (Brassica juncea Coss variety).
J Agric Food Chem
November 2011
Food Composition and Methods Development Laboratory, Beltsville Human Nutrition Research Center, Agricultural Research Service, US Department of Agriculture, Building-161, BARC-East, 10300 Baltimore Avenue, Beltsville, Maryland 20705, United States.
An UHPLC-PDA-ESI/HRMS/MS(n) profiling method was used for a comprehensive study of the phenolic components of red mustard greens ( Brassica juncea Coss variety) and identified 67 anthocyanins, 102 flavonol glycosides, and 40 hydroxycinnamic acid derivatives. The glycosylation patterns of the flavonoids were assigned on the basis of direct comparison of the parent flavonoid glycosides with reference compounds. The putative identifications were obtained from tandem mass data analysis and confirmed by the retention time, elution order, and UV-vis and high-resolution mass spectra.
View Article and Find Full Text PDFThe blue anthocyanin pigments from the blue flowers of Heliophila coronopifolia L. (Brassicaceae).
Phytochemistry
December 2011
Faculty of Pharmaceutical Sciences, Hoshi University, Shinagawa, Tokyo 142-8501, Japan.
Six acylated delphinidin glycosides (pigments 1-6) and one acylated kaempferol glycoside (pigment 9) were isolated from the blue flowers of cape stock (Heliophila coronopifolia) in Brassicaceae along with two known acylated cyanidin glycosides (pigments 7 and 8). Pigments 1-8, based on 3-sambubioside-5-glucosides of delphinidin and cyanidin, were acylated with hydroxycinnamic acids at 3-glycosyl residues of anthocyanidins. Using spectroscopic and chemical methods, the structures of pigments 1, 2, 5, and 6 were determined to be: delphinidin 3-O-[2-O-(β-xylopyranosyl)-6-O-(acyl)-β-glucopyranoside]-5-O-[6-O-(malonyl)-β-glucopyranoside], in which acyl moieties were, respectively, cis-p-coumaric acid for pigment 1, trans-caffeic acid for pigment 2, trans-p-coumaric acid for pigment 5 (a main pigment) and trans-ferulic acid for pigment 6, respectively.
View Article and Find Full Text PDFAdvanced liquid chromatography/mass spectrometry profiling of anthocyanins in relation to set of red wine varieties certified in Czech Republic.
J Chromatogr A
October 2011
Regional Centre of Advanced Technologies and Materials, Department of Analytical Chemistry, Faculty of Science, Palacky University, 17. listopadu 12, 771 46 Olomouc, Czech Republic.
Hyphenation of micro-liquid and ultra-performance liquid chromatography with a hybrid (QqTOF) tandem mass spectrometry was studied from the viewpoint of their applicability for monitoring of anthocyanin dyes in various cultivars and different vintages of red wine. After appropriate optimization both techniques proved to be suitable for this task. UHPLC system provided lower LOD and LOQ values as well as higher productivity and precision of retention parameters and peak areas with respect to micro-LC method.
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