Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry - PubMed (original) (raw)

. 2002 Mar 27;50(7):2110-6.

doi: 10.1021/jf0111561.

Affiliations

• PMID: 11902964
• DOI: 10.1021/jf0111561

Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry

Nuno Mateus et al. J Agric Food Chem. 2002.

Abstract

Three newly formed Port wine pigments were isolated by Toyopearl HW-40(s) gel chromatography and semipreparative HPLC. Furthermore, the pigments were identified by mass spectrometry (LC/MS) and NMR techniques (1D and 2D). These anthocyanin-derived pigments showed UV-visible spectra different from those of the original grape anthocyanins. These pigments correspond to malvidin 3-glucoside linked through a vinyl bond to either (+)-catechin, (-)-epicatechin, or procyanidin dimer B3 [(+)-catechin-(+)-catechin]. NMR data of these pigments are reported for the first time.

PubMed Disclaimer

Similar articles

• A new class of blue anthocyanin-derived pigments isolated from red wines.
  Mateus N, Silva AM, Rivas-Gonzalo JC, Santos-Buelga C, de Freitas V. Mateus N, et al. J Agric Food Chem. 2003 Mar 26;51(7):1919-23. doi: 10.1021/jf020943a. J Agric Food Chem. 2003. PMID: 12643652
• Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines.
  Mateus N, Carvalho E, Carvalho AR, Melo A, González-Paramás AM, Santos-Buelga C, Silva AM, De Freitas V. Mateus N, et al. J Agric Food Chem. 2003 Jan 1;51(1):277-82. doi: 10.1021/jf020695i. J Agric Food Chem. 2003. PMID: 12502421
• Occurrence of anthocyanin-derived pigments in red wines.
  Mateus N, Silva AM, Vercauteren J, de Freitas V. Mateus N, et al. J Agric Food Chem. 2001 Oct;49(10):4836-40. doi: 10.1021/jf001505b. J Agric Food Chem. 2001. PMID: 11600031
• A quarter century of wine pigment discovery.
  Waterhouse AL, Zhu J. Waterhouse AL, et al. J Sci Food Agric. 2020 Nov;100(14):5093-5101. doi: 10.1002/jsfa.9840. Epub 2019 Jul 10. J Sci Food Agric. 2020. PMID: 31157405 Review.
• Anthocyanins and their variation in red wines. II. Anthocyanin derived pigments and their color evolution.
  He F, Liang NN, Mu L, Pan QH, Wang J, Reeves MJ, Duan CQ. He F, et al. Molecules. 2012 Feb 7;17(2):1483-519. doi: 10.3390/molecules17021483. Molecules. 2012. PMID: 23442981 Free PMC article. Review.

Cited by

• Identification of the flavonoid hydroxylases from grapevine and their regulation during fruit development.
  Bogs J, Ebadi A, McDavid D, Robinson SP. Bogs J, et al. Plant Physiol. 2006 Jan;140(1):279-91. doi: 10.1104/pp.105.073262. Epub 2005 Dec 23. Plant Physiol. 2006. PMID: 16377741 Free PMC article.
• Anthocyanins and Anthocyanin-Derived Products in Yeast-Fermented Beverages.
  Ruta LL, Farcasanu IC. Ruta LL, et al. Antioxidants (Basel). 2019 Jun 18;8(6):182. doi: 10.3390/antiox8060182. Antioxidants (Basel). 2019. PMID: 31216780 Free PMC article. Review.
• NMR in the Service of Wine Differentiation.
  Viskić M, Bandić LM, Korenika AJ, Jeromel A. Viskić M, et al. Foods. 2021 Jan 8;10(1):120. doi: 10.3390/foods10010120. Foods. 2021. PMID: 33429968 Free PMC article. Review.
• New Family of Bluish Pyranoanthocyanins.
  Mateus N, Oliveira J, Haettich-Motta M, de Freitas V. Mateus N, et al. J Biomed Biotechnol. 2004;2004(5):299-305. doi: 10.1155/S1110724304404033. J Biomed Biotechnol. 2004. PMID: 15577193 Free PMC article.
• Study of the Interaction of Anthocyanins with Phenolic Aldehydes in a Model Wine Solution.
  Escott C, Morata A, Zamora F, Loira I, Del Fresno JM, Suárez-Lepe JA. Escott C, et al. ACS Omega. 2018 Nov 15;3(11):15575-15581. doi: 10.1021/acsomega.8b01828. eCollection 2018 Nov 30. ACS Omega. 2018. PMID: 31458213 Free PMC article.

Publication types

MeSH terms

Substances

LinkOut - more resources

• Full Text Sources

  • American Chemical Society