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-(3-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-(3-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.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.phytochem.2018.12.010 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Acetylated pelargonidin-3--glucoside alleviates hepatocyte lipid deposition through activating the AMPK-mediated lysosome-autophagy pathway and redox state.
Food Funct
July 2024
Department of Traditional Chinese Medicine, Sir Run Run Shaw Hospital, School of Medicine, Zhejiang University, Hangzhou, 310016, China.
Nonalcoholic fatty liver disease (NAFLD) is a worldwide public health issue, but a widely accepted therapy is still lacking until now. Anthocyanins are natural flavonoid compounds that possess various bioactivities, but their applications are limited due to their low bioavailability and stability. Acylated anthocyanins are reported to show higher stability, whereas their effects on NAFLD are still unclear.
View Article and Find Full Text PDFFast and green universal method to analyze and quantify anthocyanins in natural products by UPLC-PDA.
Food Chem
December 2023
Multidisciplinary Laboratory of Food and Health (LabMAS), School of Applied Sciences (FCA), University of Campinas, Rua Pedro Zaccaria 1300, Limeira, São Paulo 13484-350, Brazil. Electronic address:
This work developed a universal UPLC-PDA method based on safe reagents to analyze anthocyanins from different foods. Nine foods were studied by the developed chromatographic method, which was constructed using a solid core C18 column and a binary mobile phase composed of (A) water (0.25 mol.
View Article and Find Full Text PDFAssessing the diversity of anthocyanin composition in various tissues of purple corn (Zea mays L.).
Phytochemistry
September 2022
Department of Crop Sciences, University of Illinois at Urbana-Champaign, 1201 W. Gregory Drive, Urbana, IL, 61801, United States. Electronic address:
Anthocyanins are natural pigments used in various foods, beverages, textiles, and nutraceuticals. Anthocyanins in the grain of purple corn (Zea mays L., Poaceae) have been a focus of many studies, but not much is known about anthocyanins in other maize tissues.
View Article and Find Full Text PDFImprovement of stability and lipophilicity of pelargonidin-3-glucoside by enzymatic acylation with aliphatic dicarboxylic acid.
Food Chem
September 2022
Department of Traditional Chinese Medicine, Sir Run Run Shaw Hospital, School of Medicine, Zhejiang University, Hangzhou 310016, China; Department of Food Science and Nutrition, Zhejiang-Egypt Joint Laboratory for Comprehensive Utilization of Agricultural Biological Resources and Development of Functional Foods, Zhejiang University, Hangzhou 310058, China; Ningbo Research Institute, Zhejiang University, Ningbo 315100, China. Electronic address:
Dicarboxylic acids derived acylated-anthocyanins are common in nature, which can also be obtained by enzymatic acylation of anthocyanins. However, little research have focused on the properties of anthocyanins with dicarboxylic acid derivatives due to the complexity of isolation, detection, and identification. In this work, pelargonidin-3-glucoside (Pg3G) was acylated with various dicarboxylic acids.
View Article and Find Full Text PDFAcetylated pelargonidin-3--glucoside exhibits promising thermostability, lipophilicity, and protectivity against oxidative damage by activating the Nrf2/ARE pathway.
Food Funct
March 2022
Department of Food Science and Nutrition, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou 310058, China.
Anthocyanins are natural products that display diverse bioactivities but are limited in their applications by low stability and bioavailability. Acylated anthocyanins are found to possess higher stability, while their bioactivities are still obscure. In this study, acetylation of pelargonidin-3--glucoside (Pg3G) was catalyzed by lipase B (CALB) for the first time, with a conversion rate up to 88.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!