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Isolation and identification of novel pyranoanthocyanins from black carrot (Daucus carota L.) juice.
J Agric Food Chem. 2004 Aug 11; 52(16):5095-101.JA

Abstract

Six novel pyranoanthocyanins were identified by HPLC-ESI-MSn in black carrot (Daucus carota L. ssp. sativus var. atrorubens Alef.) juice. The two major compounds, namely, the vinylcatechol adducts of cyanidin 3-O-(6-O-feruloyl-beta-D-glucopyranosyl)-(1-->6)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside and cyanidin 3-O-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside, respectively, were isolated by a combination of high-speed countercurrent chromatography with semipreparative HPLC. Their structures were fully elucidated by means of one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry. The four remaining pigments were characterized as the vinylphenol and vinylguaiacol adducts of cyanidin 3-O-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside, the vinylguaiacol adduct of cyanidin 3-O-(6-O-feruloyl-beta-D-glucopyranosyl)-(1-->6)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside, and the vinylcatechol adduct of cyanidin 3-O-(6-O-sinapoyl-beta-d-glucopyranosyl)-(1-->6)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside. These compounds are formed during storage of the juice through the direct reaction of either caffeic, ferulic, or coumaric acid with the respective genuine anthocyanins.

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Authors+Show Affiliations

Schwarz M
Institute of Food Chemistry, Technical University of Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany.
Wray V
No affiliation info available
Winterhalter P
No affiliation info available

MeSH

AnthocyaninsBeveragesCaffeic AcidsChromatography, High Pressure LiquidCoumaric AcidsDaucus carotaHydrogen-Ion ConcentrationMagnetic Resonance SpectroscopySpectrometry, Mass, Electrospray Ionization

Pub Type(s)

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

Language

eng

PubMed ID

15291481

Citation

Schwarz, Michael, et al. "Isolation and Identification of Novel Pyranoanthocyanins From Black Carrot (Daucus Carota L.) Juice." Journal of Agricultural and Food Chemistry, vol. 52, no. 16, 2004, pp. 5095-101.
Schwarz M, Wray V, Winterhalter P. Isolation and identification of novel pyranoanthocyanins from black carrot (Daucus carota L.) juice. J Agric Food Chem. 2004;52(16):5095-101.
Schwarz, M., Wray, V., & Winterhalter, P. (2004). Isolation and identification of novel pyranoanthocyanins from black carrot (Daucus carota L.) juice. Journal of Agricultural and Food Chemistry, 52(16), 5095-101.
Schwarz M, Wray V, Winterhalter P. Isolation and Identification of Novel Pyranoanthocyanins From Black Carrot (Daucus Carota L.) Juice. J Agric Food Chem. 2004 Aug 11;52(16):5095-101. PubMed PMID: 15291481.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isolation and identification of novel pyranoanthocyanins from black carrot (Daucus carota L.) juice. AU - Schwarz,Michael, AU - Wray,Victor, AU - Winterhalter,Peter, PY - 2004/8/5/pubmed PY - 2004/9/14/medline PY - 2004/8/5/entrez SP - 5095 EP - 101 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 52 IS - 16 N2 - Six novel pyranoanthocyanins were identified by HPLC-ESI-MSn in black carrot (Daucus carota L. ssp. sativus var. atrorubens Alef.) juice. The two major compounds, namely, the vinylcatechol adducts of cyanidin 3-O-(6-O-feruloyl-beta-D-glucopyranosyl)-(1-->6)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside and cyanidin 3-O-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside, respectively, were isolated by a combination of high-speed countercurrent chromatography with semipreparative HPLC. Their structures were fully elucidated by means of one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry. The four remaining pigments were characterized as the vinylphenol and vinylguaiacol adducts of cyanidin 3-O-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside, the vinylguaiacol adduct of cyanidin 3-O-(6-O-feruloyl-beta-D-glucopyranosyl)-(1-->6)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside, and the vinylcatechol adduct of cyanidin 3-O-(6-O-sinapoyl-beta-d-glucopyranosyl)-(1-->6)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-galactopyranoside. These compounds are formed during storage of the juice through the direct reaction of either caffeic, ferulic, or coumaric acid with the respective genuine anthocyanins. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/15291481/Isolation_and_identification_of_novel_pyranoanthocyanins_from_black_carrot__Daucus_carota_L___juice_ L2 - https://doi.org/10.1021/jf0495791 DB - PRIME DP - Unbound Medicine ER -