Characterisation of genuine and derived cranberry proanthocyanidins by LC-ESI-MS

Food Chemistry

Volumn 128, Issue 3, 2011, Pages 802-810

  Tarascou, Isabelle ^a   Mazauric, Jean Paul ^a   Meudec, Emmanuelle ^a   Souquet, Jean Marc ^a   Cunningham, David ^b   Nojeim, Steve ^b   Cheynier, Véronique ^a   Fulcrand, Hélène ^a  

^a SPO   (France)

^b Ocean Spray Cranberries Inc   (United States)

Author keywords

A type linkage; Cranberry; LC ESI MS; Normal phase; Proanthocyanidins; Thiolysis; UV Vis spectroscopy

Indexed keywords

A-TYPE LINKAGE; CRANBERRY; LC-ESI-MS; NORMAL-PHASE; PROANTHOCYANIDINS; THIOLYSIS; UV-VIS SPECTROSCOPY;

ANTHOCYANINS; DIMERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MONOMERS; ORGANIC ACIDS; POLYMERIZATION; SPECTROMETERS; ULTRAVIOLET SPECTROSCOPY;

PHENOLS;

ANTHOCYANIN; FLAVONOL DERIVATIVE; MYCOPHENOLIC ACID; PROANTHOCYANIDIN DERIVATIVE;

ARTICLE; CRANBERRY; ELECTROSPRAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

VACCINIUM MACROCARPON;

EID: 79955624338     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2011.03.062     Document Type: Article

References (37)

1. Atanasova, V., Fulcrand, H., Cheynier, V., & Moutounet, M. (2002). Effect of oxygenation on polyphenol changes occurring in the course of wine-making. Analytica Chimica Acta, 458(1), 15-27. (Pubitemid 34273815)
2. Baldé, A. M., Pieters, L. A., Wray, V., Kolodziej, H., Vanden Berghe, D. A., Claeys, M., et al. (1991). Dimeric and trimeric proanthocyanidins possessing a doubly linked structure from Pavetta owariensis. Phytochemistry, 30(12), 4129-4135.
3. Butler, L. G., Price, M. L., & Brotherton, J. E. (1982). Vanillin assay for proanthocyanidins (condensed tannins): Modification of the solvent for estimation of the degree of polymerization. Journal of Agricultural and Food Chemistry, 30(6), 1087-1089.
4. Chen, H., Zuo, Y., & Deng, Y. (2001). Separation and determination of flavonoids and other phenolic compounds in cranberry juice by high-performance liquid chromatography. Journal of Chromatography A, 913(1-2), 387-395. (Pubitemid 32261005)
5. Duarte, S., Gregoire, S., Singh, A. P., Vorsa, N., Schaich, K., Bowen, W. H., et al. (2006). Inhibitory effects of cranberry polyphenols on formation and acidogenicity of Streptococcus mutans biofilms. FEMS Microbiology Letters, 257(1), 50-56.
6. Foo, L. Y., Lu, Y., Howell, A. B., & Vorsa, N. (2000). The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro. Phytochemistry, 54(2), 173-181. (Pubitemid 30350852)
7. Francia-Aricha, E. M., Guerra, M. T., Rivas-Gonzalo, J. C., & Santos-Buelga, C. (1997). New anthocyanin pigments formed after condensation with flavanols. Journal of Agricultural and Food Chemistry, 45(6), 2262-2266. (Pubitemid 127485558)
8. Fulcrand, H., Cameira-dos-Santos, P. J., Sarni-Manchado, P., Cheynier, V., & Favre-Bonvin, J. (1996). Structure of new anthocyanin-derived wine pigments. Journal of the Chemical Society, Perkin Transactions 1, 7, 735-739. (Pubitemid 126801231)
9. Gu, L., Kelm, M., Hammerstone, J. F., Beecher, G., Cunningham, D., Vannozzi, S., et al. (2002). Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. Journal of Agricultural and Food Chemistry, 50(17), 4852-4860. (Pubitemid 34856155)
10. Gu, L., Kelm, M. A., Hammerstone, J. F., Beecher, G., Holden, J., Haytowitz, D., et al. (2003). Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation. Journal of Agricultural and Food Chemistry, 51(25), 7513-7521.
11. Hammerstone, J. F., Lazarus, S. A., Mitchell, A. E., Rucker, R., & Schmitz, H. H. (1999). Identification of procyanidins in cocoa (Theobroma cacao) and chocolate using high-performance liquid chromatography mass spectrometry. Journal of Agricultural and Food Chemistry, 47(2), 490-496. (Pubitemid 29185214)
12. He, J., Santos-Buelga, C., Mateus, N., & de Freitas, V. (2006). Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments form red wines by combination of column chromatographic techniques. Journal of Chromatography A, 1134, 215-225. (Pubitemid 44633951)
13. Hong, V., & Wrolstad, R. E. (1990). Use of HPLC separation photodiode array detection for characterization of anthocyanins. Journal of Agricultural and Food Chemistry, 38(3), 708-715.
14. Howell, A. B. (2002). Cranberry proanthocyanidins and the maintenance of urinary tract health. Critical Reviews in Food Science and Nutrition, 42(3), 273-278.
15. Howell, A. B., Reed, J. D., Krueger, C. G., Winterbottom, R., Cunningham, D. G., & Leahy, M. (2005). A-type cranberry proanthocyanidins and uropathogenic bacterial anti-adhesion activity. Phytochemistry, 66(18), 2281-2291. (Pubitemid 41254101)
16. Krueger, C. G., Vestling, M. M., & Reed, J. D. (2004). Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of anthocyanin-polyflavan-3-ol oligomers in cranberry fruit (Vaccinium macrocarpon. Ait.) and spray dried cranberry juice. In A. L. Waterhouse, J. A. Kennedy (Eds.), ACS symposium series (Vol. 886, pp. 232-246). Washington, DC.
17. McMurrough, I., & McDowell, J. (1978). Chromatographic-separation and automated-analysis of flavanols. Analytical Biochemistry, 91(1), 92-100.
18. Neto, C. C. (2007). Cranberry and blueberry: Evidence for protective effects against cancer and vascular diseases. Molecular Nutrition and Food Research, 51(6), 652-664.
19. Neto, C. C., Krueger, C. G., Lamoureaux, T. L., Kondo, M., Vaisberg, A. J., Hurta, R. A. R., et al. (2006). MALDI-TOF MS characterization of proanthocyanidins from cranberry fruit (Vaccinium macrocarpon) that inhibit tumor cell growth and matrix metalloproteinase expression in vitro. Journal of the Science of Food and Agriculture, 86(1), 18-25. (Pubitemid 41820202)
20. Pati, S., Lositio, I., Gambacorta, G., La Notte, E., Palmisano, F., & Zambonin, P. G. (2006). Simultaneous separation and identification of oligomeric procyanidins and anthocyanin-derived pigments in raw red wine by HPLC-UV-ESI-MSn. Journal of Mass Spectrometry, 41(7), 861-871. (Pubitemid 44106047)
21. Peng, Z., Hayasaka, Y., Iland, P. G., Sefton, M., Hoj, P., & Waters, E. J. (2001). Quantitative analysis of polymeric procyanidins (tannins) from grape (Vitis vinifera) seeds by reverse phase high-performance liquid chromatography. Journal of Agricultural and Food Chemistry, 49(1), 26-31. (Pubitemid 32104483)
22. Porter, L. J., Hrstich, L. N., & Chan, B. G. (1986). The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry, 25(1), 223-230.
23. Porter, M. L., Krueger, C. G., Wiebe, D. A., Cunningham, D. G., & Reed, J. D. (2001). Cranberry proanthocyanidins associate with low-density lipoprotein and inhibit in vitro Cu2+-induced oxidation. Journal of the Science of Food and Agriculture, 81(12), 1306-1313. (Pubitemid 33001732)
24. Prieur, C., Rigaud, J., Cheynier, V., & Moutounet, M. (1994). Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry, 36(3), 781-784. (Pubitemid 2098191)
25. Prior, R. L., & Gu, L. (2005). Occurrence and biological significance of proanthocyanidins in the American diet. Phytochemistry, 66(18), 2264-2280. (Pubitemid 41254100)
26. Reed, J. D., Krueger, C. G., & Vestling, M. M. (2005). MALDI-TOF mass spectrometry of oligomeric food polyphenols. Phytochemistry, 66(18), 2248-2263. (Pubitemid 41254099)
27. Rigaud, J., Perez-Ilzarbe, X., Ricardo da Silva, J. M., & Cheynier, V. (1991). Micro method for the identification of proanthocyanidin using thiolysis monitored by high-performance liquid chromatography. Journal of Chromatography, 540, 401-405.
28. Singleton, V. L., Orthofer, R., & Lamuela-Raventós, R. M. (1999). Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods in Enzymology, 299, 152-178.
29. Sun, J., Chu, Y. F., Wu, X., & Liu, R. H. (2002). Antioxidant and antiproliferative activities of common fruits. Journal of Agricultural and Food Chemistry, 50(25), 7449-7454. (Pubitemid 35424917)
30. Sun, J., & Liu, R. H. (2006). Cranberry phytochemical extracts induce cell cycle arrest and apoptosis in human MCF-7 breast cancer cells. Cancer Letters, 241(1), 124-134.
31. Tamura, F., Tanabe, K., Itai, A., & Hasegawa, M. (1999). Characteristics of acetaldehyde accumulation and removal of astringency with ethanol and carbon dioxide treatments in 'Saijo' persimmon fruit. Journal of the Japanese Society for Horticultural Science, 68(6), 1178-1183.
32. Timberlake, C. F., & Bridle, P. (1976). Interactions between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. American Journal of Enology and Viticulture, 27(3), 97-105.
33. Vinson, J. A., Bose, P., Proch, J., Al Kharrat, H., & Samman, N. (2008). Cranberries and cranberry products: Powerful in vitro, ex vivo, and in vivo sources of antioxidants. Journal of Agricultural and Food Chemistry, 56(14), 5884-5891.
34. Vvedenskaya, I. O., Rosen, R. T., Guido, J. E., Russell, D. J., Mills, K. A., & Vorsa, N. (2004). Characterization of flavonols in cranberry (Vaccinium macrocarpon) powder. Journal of Agricultural and Food Chemistry, 52(2), 188-195.
35. Wilson, T., Porcari, J. P., & Harbin, D. (1998). Cranberry extract inhibits low density lipoprotein oxidation. Life Sciences, 62(24), 381-386. (Pubitemid 28248443)
36. Yan, X. J., Murphy, B. T., Hammond, G. B., Vinson, J. A., & Neto, C. C. (2002). Antioxidant activities and antitumor screening of extracts from cranberry fruit (Vaccinium macrocarpon). Journal of Agricultural and Food Chemistry, 50(21), 5844-5849. (Pubitemid 35155303)
37. Zuo, Y., Wang, C., & Zhan, J. (2002). Separation, characterization, and quantitation of benzoic and phenolic antioxidants in American cranberry fruit by GC-MS. Journal of Agricultural and Food Chemistry, 50(13), 3789-3794. (Pubitemid 34640708)