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Characterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice.
J Agric Food Chem. 2004 Dec 01; 52(24):7331-8.JA

Abstract

Anthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juices were isolated and purified by means of high-speed countercurrent chromatography and preparative high-performance liquid chromatography. Structures of the pigments were then elucidated by electrospray ionization multiple mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. The major anthocyanins of the juice were characterized as cyanidin 3-glucoside and cyanidin 3-(6"-malonylglucoside). Furthermore, six minor anthocyanins were detected and identified as cyanidin 3,5-diglucoside, delphinidin 3-glucoside, cyanidin 3-sophoroside, delphinidin 3-(6"-malonylglucoside), peonidin 3-(6"-malonylglucoside), and cyanidin 3-(6"-dioxalylglucoside). The occurrence of the latter compound in blood oranges is reported here for the first time, together with full NMR spectroscopic data. Further investigations revealed the presence of four anthocyanin-derived pigments, which are formed through a direct reaction between anthocyanins and hydroxycinnamic acids during prolonged storage of the juice. These novel pyranoanthocyanins were identified as the 4-vinylphenol, 4-vinylcatechol, 4-vinylguaiacol, and 4-vinylsyringol adducts of cyanidin 3-glucoside through comparison of their mass spectrometric and chromatographic properties with those of synthesized reference compounds.

Authors+Show Affiliations

Institute of Food Chemistry, Technical University of Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

15563216

Citation

Hillebrand, Silke, et al. "Characterization of Anthocyanins and Pyranoanthocyanins From Blood Orange [Citrus Sinensis (L.) Osbeck] Juice." Journal of Agricultural and Food Chemistry, vol. 52, no. 24, 2004, pp. 7331-8.
Hillebrand S, Schwarz M, Winterhalter P. Characterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice. J Agric Food Chem. 2004;52(24):7331-8.
Hillebrand, S., Schwarz, M., & Winterhalter, P. (2004). Characterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice. Journal of Agricultural and Food Chemistry, 52(24), 7331-8.
Hillebrand S, Schwarz M, Winterhalter P. Characterization of Anthocyanins and Pyranoanthocyanins From Blood Orange [Citrus Sinensis (L.) Osbeck] Juice. J Agric Food Chem. 2004 Dec 1;52(24):7331-8. PubMed PMID: 15563216.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characterization of anthocyanins and pyranoanthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juice. AU - Hillebrand,Silke, AU - Schwarz,Michael, AU - Winterhalter,Peter, PY - 2004/11/26/pubmed PY - 2004/12/24/medline PY - 2004/11/26/entrez SP - 7331 EP - 8 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 52 IS - 24 N2 - Anthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juices were isolated and purified by means of high-speed countercurrent chromatography and preparative high-performance liquid chromatography. Structures of the pigments were then elucidated by electrospray ionization multiple mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. The major anthocyanins of the juice were characterized as cyanidin 3-glucoside and cyanidin 3-(6"-malonylglucoside). Furthermore, six minor anthocyanins were detected and identified as cyanidin 3,5-diglucoside, delphinidin 3-glucoside, cyanidin 3-sophoroside, delphinidin 3-(6"-malonylglucoside), peonidin 3-(6"-malonylglucoside), and cyanidin 3-(6"-dioxalylglucoside). The occurrence of the latter compound in blood oranges is reported here for the first time, together with full NMR spectroscopic data. Further investigations revealed the presence of four anthocyanin-derived pigments, which are formed through a direct reaction between anthocyanins and hydroxycinnamic acids during prolonged storage of the juice. These novel pyranoanthocyanins were identified as the 4-vinylphenol, 4-vinylcatechol, 4-vinylguaiacol, and 4-vinylsyringol adducts of cyanidin 3-glucoside through comparison of their mass spectrometric and chromatographic properties with those of synthesized reference compounds. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/15563216/Characterization_of_anthocyanins_and_pyranoanthocyanins_from_blood_orange_[Citrus_sinensis__L___Osbeck]_juice_ L2 - https://doi.org/10.1021/jf0487957 DB - PRIME DP - Unbound Medicine ER -