Isolation and structural characterization of unusual pyranoanthocyanins and related anthocyanins from Staghorn sumac (Rhus typhina L.) via UPLC-ESI-MS, (1)H, (13)C, and 2D NMR spectroscopy

The six major anthocyanins found in the burgundy coloured fruits of Staghorn sumac (Rhus typhina L.) were isolated and the structures of four compounds were determined by NMR spectroscopic methods as being: 7-O-methyl-delphinidin-3-O-(2″galloyl)-β-d-galactopyranoside; 7-O-methyl-cyanidin-3-O-(2″gall...

Full description

Saved in:
Bibliographic Details
Published inPhytochemistry (Oxford) Vol. 94; pp. 284 - 293
Main Authors Kirby, Christopher W, Wu, Tao, Tsao, Rong, McCallum, Jason L
Format Journal Article
LanguageEnglish
Published England 01.10.2013
Subjects
Anthocyanins - analysis
Anthocyanins - chemistry
Anthocyanins - isolation & purification
Chromatography, High Pressure Liquid - methods
Fruit - chemistry
Magnetic Resonance Spectroscopy - methods
Molecular Structure
Pyrans - chemistry
Rhus - chemistry
Spectrometry, Mass, Electrospray Ionization - methods
Anthocyanin
Vinyl-catechol
Staghorn sumac
Sumadin
Pyranoanthocyanin
Anacardiaceae
Rhus typhina
Online AccessGet full text

Cover

More Information
Summary:The six major anthocyanins found in the burgundy coloured fruits of Staghorn sumac (Rhus typhina L.) were isolated and the structures of four compounds were determined by NMR spectroscopic methods as being: 7-O-methyl-delphinidin-3-O-(2″galloyl)-β-d-galactopyranoside; 7-O-methyl-cyanidin-3-O-(2″galloyl)-β-d-galactopyranoside; 7-O-methyl-delphinidin-3-O-(2″'galloyl)-β-d-galactopyranoside-4-vinyl-catechol-3″-O-β-d-glucopyranoside; and 7-O-methyl-cyanidin-3-O-(2″'galloyl)-β-d-galactopyranoside-4-vinyl-catechol-3″-O-β-d-glucopyranoside, respectively. Additionally, two related anthocyanin compounds, cyanidin-3-O-(2″galloyl)-β-d-galactopyranoside and 7-O-methyl-cyanidin-3-O-β-d-galactopyranoside were also recovered, with NMR spectroscopic values closely matching previous reports from other plant species. The prevalence of 7-O-methyl anthocyanins and their galloylated derivatives in sumac is highly unusual, and warrants special attention. Additionally, the in planta occurrence of two 7-O-methyl-pyranoanothocyanin-vinyl-catechol aglycones, Sumadin A and Sumadin B, and their derivatives is noted. To our knowledge, E-ring glycosylated vinyl-catechol pyranoanthocyanins were previously unknown.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1873-3700
DOI:10.1016/j.phytochem.2013.06.017