Identification of Procyanidins in Cocoa (Theobroma cacao) and Chocolate Using High-Performance Liquid Chromatography/Mass Spectrometry
Abstract
Monomeric and oligomeric procyanidins present in cocoa and chocolate were separated and identified using a modified normal-phase high-performance liquid chromatography (HPLC) method coupled with on-line mass spectrometry (MS) analysis using an atmospheric pressure ionization electrospray chamber. The chromatographic separation was achieved using a silica stationary phase in combination with a gradient ascending in polarity. This qualitative report confirms the presence of a complex series of procyanidins in raw cocoa and certain chocolates using HPLC/MS techniques. Although both cocoa and chocolate contained monomeric and oligomeric procyanidin units 2-10, only use of negative mode provided MS data for the higher oligomers (i.e., >pentamer). Application of this method for qualitative analysis of proanthocyanidins in other food products and confirmation of this method as a reliable quantitative tool for determining levels of procyanidins in cocoa, chocolate, and other food products are currently being investigated.
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Cites
Flavonoids in Health and Disease
Rucker, R. B. (2004) · American Journal of Clinical Nutrition · doi:10.1093/ajcn/79.5.891a · Cited by 555 · see citing works
Self-citationThompson, R., Jacques, D., Haslam, E., et al. (1972) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/p19720001387 · Cited by 464 · see citing works
(1990) · Methods in plant biochemistry · doi:10.1016/b978-0-12-461012-5.50001-x · Cited by 423 · see citing works
Phenolic Compounds in Food and Their Effects on Health II
Huang1, M.-T., Ho, C., & Lee, C. Y. (1992) · ACS symposium series · doi:10.1021/bk-1992-0507 · Cited by 359 · see citing works
Chromatographic Science Series
(2010) · Chromatographic science/Chromatographic science series · doi:10.1201/crcchromasci · Cited by 251 · see citing works
Antioxidative Polyphenols Isolated from Theobroma cacao
Sanbongi, C., Osakabe, N., Natsume, M., Takizawa, T., Gomi, S., & Osawa, T. (1998) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf970575o · Cited by 222 · see citing works
Porter, L. J. (1988) · Springer eBooks · doi:10.1007/978-1-4899-2913-6_2 · Cited by 200 · see citing works
New Methods of Analyzing Tannins
Okuda, T., Yoshida, T., & Hatano, T. (1989) · Journal of Natural Products · doi:10.1021/np50061a001 · Cited by 171 · see citing works
Guyot, S., Doco, T., Souquet, J., Moutounet, M., & Drilleau, J. (1997) · Phytochemistry · doi:10.1016/s0031-9422(96)00480-3 · Cited by 165 · see citing works
Rigaud, J., Escribano-Bailón, M. T., Prieur, C., Souquet, J., & Cheynier, V. (1993) · Journal of Chromatography A · doi:10.1016/0021-9673(93)83368-3 · Cited by 159 · see citing works
Cacao procyanidins: major flavanoids and identification of some minor metabolites
Porter, L. J., Ma, Z., & Chan, B. G. (1991) · Phytochemistry · doi:10.1016/0031-9422(91)84228-k · Cited by 158 · see citing works
Ohnishi‐Kameyama, M., Yanagida, A., Kanda, T., et al. (1997) · Rapid Communications in Mass Spectrometry · doi:10.1002/(sici)1097-0231(19970115)11:1 · Cited by 158 · see citing works
HPLC/MS Application to Anthocyanins of Vitis vinifera L.
Baldi, A., Romani, A., Mulinacci, N., et al. (1995) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00056a027 · Cited by 149 · see citing works
Molluscicides from the cashew Anacardium occidentale and their large-scale isolation
Kubo, I., Komatsu, S., & Ochi, M. (1986) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00072a010 · Cited by 130 · see citing works
The phenolics of ciders: Oligomeric and polymeric procyanidins
Lea, A. G. H. (1978) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2740290511 · Cited by 106 · see citing works
Morimoto, S., Nonaka, G., & Nishioka, I. (1986) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.34.633 · Cited by 102 · see citing works
Karchesy, J. J., & Hemingway, R. W. (1986) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf00072a009 · Cited by 98 · see citing works
Fast atom bombardment mass spectrometry of polyphenols (syn. vegetable tannins)
Self, R., Eagles, J., Galletti, G. C., et al. (1986) · Journal of Mass Spectrometry · doi:10.1002/bms.1200130902 · Cited by 81 · see citing works
Peterson, J. J., & Dwyer, J. T. (1998) · Journal of the American Dietetic Association · doi:10.1016/s0002-8223(98)00153-9 · Cited by 77 · see citing works
McMurrough, I., & Baert, T. (1994) · Journal of the Institute of Brewing · doi:10.1002/j.2050-0416.1994.tb00839.x · Cited by 70 · see citing works
Proanthocyanidins with ( + )-epicatechin units from Byrsonima crassifolia bark
Geiss, F., Heinrich, M., Hunkler, D., et al. (1995) · Phytochemistry · doi:10.1016/0031-9422(94)00934-l · Cited by 59 · see citing works
Use of Binary Solvent Systems in the MALDI-TOF Analysis of Poly(methyl methacrylate)
Chen, H., & Guo, B. (1997) · Analytical Chemistry · doi:10.1021/ac970409f · Cited by 55 · see citing works
Polyphenols of mature plant, seedling and tissue cultures of Theobroma cacao
Jalal, M. A. F., & Collin, H. A. (1977) · Phytochemistry · doi:10.1016/s0031-9422(00)88786-5 · Cited by 49 · see citing works
Catechins of green tea: antioxidant activity
Lunder, T. L. (1992) · ACS Symposium series. American Chemical Society · Cited by 37 · see citing works
The Precursors of Chocolate Aroma: Production of Reducing Sugars during Fermentation of Cocoa Beans
Rohan, T. A., & STEWART, T. (1967) · Journal of Food Science · doi:10.1111/j.1365-2621.1967.tb09694.x · Cited by 33 · see citing works
Fractionation and properties of the polymeric leucocyanidin of the seeds of Theobroma cacao
Quesnel, V. C. (1968) · Phytochemistry · doi:10.1016/s0031-9422(00)88610-0 · Cited by 32 · see citing works
Chiàvari, G., Vitali, P., & Galletti, G. C. (1987) · Journal of Chromatography A · doi:10.1016/s0021-9673(01)94287-6 · Cited by 23 · see citing works
Cárdenas, M. S., van der Heeft, E., & de Jong, A. P. J. M. (1997) · Rapid Communications in Mass Spectrometry · doi:10.1002/(sici)1097-0231(199708)11:12 · Cited by 21 · see citing works
Polymere Procyanidine, die pr�genden Bestandteile der Mandel-Samenschale
Brieskorn, C. H., & Betz, R. (1988) · European Food Research and Technology · doi:10.1007/bf01454426 · Cited by 17 · see citing works
Rohan, T. A. (1967) · Journal of Food Science · doi:10.1111/j.1365-2621.1967.tb09695.x · Cited by 11 · see citing works
Erratum. New Methods of Analyzing Tannins
Okuda, T., Yoshida, T., & Hatano, T. (1989) · Journal of Natural Products · doi:10.1021/np50063a037 · Cited by 6 · see citing works
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Calder, P. C., Ahluwalia, N., Brouns, F., Buetler, T., Clement, K., Cunningham, K., Esposito, K., Jönsson, L. S., Kolb, H., Lansink, M., et al. (2011) · British Journal of Nutrition · doi:10.1017/s0007114511005460 · Cited by 1,098 · see citing works
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Awika, J. M., & Rooney, L. W. (2004) · Phytochemistry · doi:10.1016/j.phytochem.2004.04.001 · Cited by 966 · see citing works
Taubert, D., Roesen, R., Lehmann, C., Jung, N., & Schömig, E. (2007) · JAMA · doi:10.1001/jama.298.1.49 · Cited by 476 · see citing works
Adamson, G. E., Lazarus, S. A., Mitchell, A. E., Prior, R. L., Cao, G., Jacobs, P. H., Kremers, B. G., Hammerstone, J. F., Rucker, R. B., Ritter, K. A., et al. (1999) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf990317m · Cited by 404 · see citing works
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Hammerstone, J. F., Lazarus, S. A., & Schmitz, H. H. (2000) · The Journal of Nutrition · doi:10.1093/jn/130.8.2086s · Cited by 356 · see citing works
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Lazarus, S. A., Adamson, G. E., Hammerstone, J. F., & Schmitz, H. H. (1999) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf9813642 · Cited by 263 · see citing works
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Ito, M., Kudo, N., Miyake, Y., Imai, T., Unno, T., Yamashita, Y., Hirota, Y., Ashida, H., & Osakabe, N. (2017) · Experimental Gerontology · doi:10.1016/j.exger.2017.07.010 · Cited by 10 · see citing works
- Authors
- Hammerstone, J. F., Lazarus, S. A., Mitchell, A. E., Rucker, R., & Schmitz, H. H.
- Affiliations
- University of California, Davis (US)
- Corresponding author
- Hammerstone, John F.
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-01-14
- Volume
- 47
- Issue
- 2
- Pages
- 490-496
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W1997922496
- Cited by
- 455
- References
- 31
- Citations by year
- 2026: 1 · 2025: 4 · 2024: 2 · 2023: 7 · 2022: 6 · 2021: 7 · 2020: 15 · 2019: 15 · 2018: 18 · 2017: 15 · 2016: 19 · 2015: 24 · 2014: 30 · 2013: 25 · 2012: 33
- FWCI
- 46.99
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Agricultural and Food Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Agricultural and Biological Sciences › Food Science › Food Chemistry and Fat Analysis
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Keywords
- procyanidins, Theobroma cacao, chocolate, proanthocyanidins, oligomeric procyanidins, normal-phase HPLC, negative ion mode, cocoa flavonoids
- MeSH terms
- Cacao, Catechin, Chromatography, High Pressure Liquid, Mass Spectrometry, Proanthocyanidins, Biflavonoids
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