Quantification of ascorbyl adducts of epigallocatechin gallate and gallocatechin gallate in bottled tea beverages

W.-L. Hung, S. Wang, S. Sang, X. Wan, Y. Wang, C.-T. Ho

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Catechins are the major bioactive compounds existing in tea leaves (Camellia sinensis). Dehydroascorbic acid is (DHAA) a reactive dicarbonyl species and previous studies have demonstrated that catechins could effectively trap DHAA to form ascorbyl adducts of catechins, especially epigallocatechin gallate (EGCG). Since catechins in the aqueous solution are unstable due to their structural features, ascorbic acid (AA) is usually added to bottled tea beverages to protect catechins. However, whether ascorbyl adducts of catechins are formed in bottled tea beverages remains unclear. In this study, formation of ascorbyl adducts of EGCG increased along with increased incubation time when EGCG and AA were dissolved in the aqueous solution. Next, 6C-DHAA-EGCG and 8C-DHAA-EGCG were detected in both green tea and oolong tea beverages, and their concentrations ranged from 0.23 to 1.95 µM and 0.28 to 1.97 µM, respectively. Furthermore, an 8C-ascorbyl adduct derived from gallocatechin gallate was also found in some tea beverages. © 2018 Elsevier Ltd
Original languageEnglish
Pages (from-to)246-252
Number of pages7
JournalFood Chemistry
Volume261
DOIs
Publication statusPublished - 2018
Externally publishedYes

Fingerprint

tea (beverage)
Beverages
Catechin
epigallocatechin
Tea
flavanols
Dehydroascorbic Acid
beverages
dehydroascorbic acid
Ascorbic Acid
aqueous solutions
ascorbic acid
Camellia sinensis
green tea
epigallocatechin gallate
gallocatechin gallate
traps
leaves

Keywords

  • Ascorbic acid
  • Ascorbyl adducts
  • Epigallocatechin gallate
  • Gallocatechin gallate
  • Tea beverages
  • Beverages
  • Flavonoids
  • Phenols
  • Solutions
  • Bioactive compounds
  • Camellia sinensis
  • Dehydroascorbic acid
  • Gallate
  • Incubation time
  • Structural feature
  • ascorbic acid
  • catechin
  • epigallocatechin gallate
  • gallocatechin gallate
  • unclassified drug
  • aqueous solution
  • Article
  • drug determination
  • high performance liquid chromatography
  • incubation time
  • tea

Cite this

Quantification of ascorbyl adducts of epigallocatechin gallate and gallocatechin gallate in bottled tea beverages. / Hung, W.-L.; Wang, S.; Sang, S.; Wan, X.; Wang, Y.; Ho, C.-T.

In: Food Chemistry, Vol. 261, 2018, p. 246-252.

Research output: Contribution to journalArticle

Hung, W.-L. ; Wang, S. ; Sang, S. ; Wan, X. ; Wang, Y. ; Ho, C.-T. / Quantification of ascorbyl adducts of epigallocatechin gallate and gallocatechin gallate in bottled tea beverages. In: Food Chemistry. 2018 ; Vol. 261. pp. 246-252.
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abstract = "Catechins are the major bioactive compounds existing in tea leaves (Camellia sinensis). Dehydroascorbic acid is (DHAA) a reactive dicarbonyl species and previous studies have demonstrated that catechins could effectively trap DHAA to form ascorbyl adducts of catechins, especially epigallocatechin gallate (EGCG). Since catechins in the aqueous solution are unstable due to their structural features, ascorbic acid (AA) is usually added to bottled tea beverages to protect catechins. However, whether ascorbyl adducts of catechins are formed in bottled tea beverages remains unclear. In this study, formation of ascorbyl adducts of EGCG increased along with increased incubation time when EGCG and AA were dissolved in the aqueous solution. Next, 6C-DHAA-EGCG and 8C-DHAA-EGCG were detected in both green tea and oolong tea beverages, and their concentrations ranged from 0.23 to 1.95 µM and 0.28 to 1.97 µM, respectively. Furthermore, an 8C-ascorbyl adduct derived from gallocatechin gallate was also found in some tea beverages. {\circledC} 2018 Elsevier Ltd",
keywords = "Ascorbic acid, Ascorbyl adducts, Epigallocatechin gallate, Gallocatechin gallate, Tea beverages, Beverages, Flavonoids, Phenols, Solutions, Bioactive compounds, Camellia sinensis, Dehydroascorbic acid, Gallate, Incubation time, Structural feature, ascorbic acid, catechin, epigallocatechin gallate, gallocatechin gallate, unclassified drug, aqueous solution, Article, drug determination, high performance liquid chromatography, incubation time, tea",
author = "W.-L. Hung and S. Wang and S. Sang and X. Wan and Y. Wang and C.-T. Ho",
note = "Export Date: 19 September 2018 CODEN: FOCHD 通訊地址: Wang, Y.; Department of Food Science, Rutgers University, 65, Dudley Rd., United States; 電子郵件: yu.wang@ufl.edu 化學物質/CAS: ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; catechin, 13392-26-2, 154-23-4; epigallocatechin gallate, 989-51-5 參考文獻: Ananingsih, V.K., Sharma, A., Zhou, W., Green tea catechins during food processing and storage: A review on stability and detection (2013) Food Research International, 50 (2), pp. 469-473; Bianchi, A., Marchetti, N., Scalia, S., Photodegradation of EGCG in topical cream formulations and its photostabilization (2011) Journal of Pharmaceutical and Biomedical Analysis, 56 (4), pp. 692-697; Butt, M.S., Sultan, M.T., Green tea: Nature's defense against malignancies (2009) Critical Reviews in Food Science and Nutrition, 49 (5), pp. 463-473; Chen, Z.Y., Zhu, Q.Y., Tsang, D., Huang, Y., Degradation of green tea catechins in tea drinks (2001) Journal of Agricultural and Food Chemistry, 49 (1), pp. 477-482; Chen, Z.Y., Zhu, Q.Y., Wong, Y.F., Zhang, Z., Chung, H.Y., Stabilizing effect of ascorbic acid on green tea catechins (1998) Journal of Agricultural and Food Chemistry, 46 (7), pp. 2512-2516; Cheng, R., Lin, B., Lee, K.W., Ortwerth, B.J., Similarity of the yellow chromophores isolated from human cataracts with those from ascorbic acid-modified calf lens proteins: Evidence for ascorbic acid glycation during cataract formation (2001) Biochemica et Biophysica Acta – Molecular Basis of Disease, 1537 (1), pp. 14-26; Dube, A., Ng, K., Nicolazzo, J.A., Larson, J., Effective use of reducing agents and nanoparticle encapsulation in stabilizing catechins in alkaline solution (2010) Food Chemistry, 122, pp. 662-667; Graham, H.N., Green tea composition, consumption and polyphenol chemistry (1992) Preventive Medicine, 21 (3), pp. 334-350; Hashimoto, F., Nonaka, G., Nishioka, I., Tannins and related compounds XC. 8-C-ascorbyl epigallocatechin 3-gallate and novel dimeric flavan-3-ols, oolonghomogisflavans A and B, from oolong tea (1989) Chemical & Pharmaceutical Bulletin, 37 (12), pp. 3255-3263; Hayat, K., Iqbal, H., Malik, U., Bilal, U., Mushtaq, S., Tea and its consumptions: Benefits and risks (2015) Critical Reviews in Food Science and Nutrition, 55 (7), pp. 939-994; Ho, C.T., Chen, Q., Shi, H., Zhang, K.Q., Rosen, R.T., Antioxidant effect of polyphenol extract prepared from various Chinese teas (1992) Preventive Medicine, 21 (4), pp. 520-525; Murakami, I., Nakamura, T., Ishibashi, Y., Shibuya, R., Ayano, E., Morita-Murase, Y., Kanazawa, H., Simultaneous determination of catechins and procyanidins in bottled tea drinks by LC/MS (2006) Chromatography, 27 (1), pp. 27-33; Ortwerth, B.J., Feather, M.S., Olesen, P.R., The precipitation of cross-linking of lens crystallins by ascorbic acid (1988) Experimental Eye Research, 47 (1), pp. 155-168; Sang, S., Lambert, J.D., Ho, C.T., Yang, C.S., The chemistry and biotransformation of tea constituents (2011) Pharmacological Research, 64, pp. 87-99; Sang, S., Lee, M.J., Hou, Z., Ho, C.T., Yang, C.S., Stability of tea polyphenol EGCG and formation of dimers and epimers under common experimental conditions (2005) Journal of Agricultural and Food Chemistry, 53 (24), pp. 9478-9484; Schimidt, H.L., Garcia, A., Martins, A., Mello-Carpes, P.B., Carpes, F.P., Green tea supplementation produces better neuroprotective effects than red and black tea in Alzheimer's-like rat model (2017) Food Research International, 100, pp. 442-448; Shpigelman, A., Israeli-Ler, G., Livney, Y.D., Thermally-induced protein-polyphenol co-assemblies; beta-lactoglobulin-based nanocomplexes as protective nanovehicles for EGCG (2010) Food Hydrocolloid, 24, pp. 735-743; Stewart, A.J., Mullen, W., Crozier, A., 0. On-line high-performance liquid chromatography analysis of the antioxidant activity of phenolic compounds in green and black tea (2005) Molecular Nutrition & Food Research, 49 (1), pp. 52-60; Su, Y.L., Leung, L.K., Huang, Y., Chen, Z.Y., Stability of tea theaflavins and catechins (2003) Food Chemistry, 83 (2), pp. 189-195; Wang, R., Zhou, W., Jiang, X., Reaction kinetics of degradation and epimerization of EGCG in aqueous system over a wide temperature range (2008) Journal of Agricultural and Food Chemistry, 56 (8), pp. 2694-2701; Watanabe, T., Nishiyama, R., Yamamoto, A., Nagai, S., Terabe, S., Simultaneous analysis of individual catechins, caffeine, and ascorbic acid in commercial canned green and black teas by micellar electrokinetic chromatography (1998) Analytical Sciences, 14, pp. 435-438; Xu, J.Z., Leung, L.K., Huang, Y., Chen, Z.Y., Epimerization of tea polyphenols in tea drinks (2003) Journal of the Science of Food and Agriculture, 83 (15), pp. 1617-1621; Xu, J.Z., Yeung, S.Y.V., Chang, Q., Huang, Y., Chen, Z.Y., Comparison of antioxidant activity and bioavailability of tea epicatechin with their epimers (2004) British Journal of Nutrition, 91, pp. 873-881; Zhu, Y., Zhao, Y., Wang, P., Ahmedna, M., Ho, C.T., Sang, S., Tea flavanols block advanced glycation of lens crystallins induced by dehydroascorbic acid (2015) Chemical Research in Toxicology, 28 (1), pp. 135-143",
year = "2018",
doi = "10.1016/j.foodchem.2018.04.050",
language = "English",
volume = "261",
pages = "246--252",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier Ltd",

}

TY - JOUR

T1 - Quantification of ascorbyl adducts of epigallocatechin gallate and gallocatechin gallate in bottled tea beverages

AU - Hung, W.-L.

AU - Wang, S.

AU - Sang, S.

AU - Wan, X.

AU - Wang, Y.

AU - Ho, C.-T.

N1 - Export Date: 19 September 2018 CODEN: FOCHD 通訊地址: Wang, Y.; Department of Food Science, Rutgers University, 65, Dudley Rd., United States; 電子郵件: yu.wang@ufl.edu 化學物質/CAS: ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; catechin, 13392-26-2, 154-23-4; epigallocatechin gallate, 989-51-5 參考文獻: Ananingsih, V.K., Sharma, A., Zhou, W., Green tea catechins during food processing and storage: A review on stability and detection (2013) Food Research International, 50 (2), pp. 469-473; Bianchi, A., Marchetti, N., Scalia, S., Photodegradation of EGCG in topical cream formulations and its photostabilization (2011) Journal of Pharmaceutical and Biomedical Analysis, 56 (4), pp. 692-697; Butt, M.S., Sultan, M.T., Green tea: Nature's defense against malignancies (2009) Critical Reviews in Food Science and Nutrition, 49 (5), pp. 463-473; Chen, Z.Y., Zhu, Q.Y., Tsang, D., Huang, Y., Degradation of green tea catechins in tea drinks (2001) Journal of Agricultural and Food Chemistry, 49 (1), pp. 477-482; Chen, Z.Y., Zhu, Q.Y., Wong, Y.F., Zhang, Z., Chung, H.Y., Stabilizing effect of ascorbic acid on green tea catechins (1998) Journal of Agricultural and Food Chemistry, 46 (7), pp. 2512-2516; Cheng, R., Lin, B., Lee, K.W., Ortwerth, B.J., Similarity of the yellow chromophores isolated from human cataracts with those from ascorbic acid-modified calf lens proteins: Evidence for ascorbic acid glycation during cataract formation (2001) Biochemica et Biophysica Acta – Molecular Basis of Disease, 1537 (1), pp. 14-26; Dube, A., Ng, K., Nicolazzo, J.A., Larson, J., Effective use of reducing agents and nanoparticle encapsulation in stabilizing catechins in alkaline solution (2010) Food Chemistry, 122, pp. 662-667; Graham, H.N., Green tea composition, consumption and polyphenol chemistry (1992) Preventive Medicine, 21 (3), pp. 334-350; Hashimoto, F., Nonaka, G., Nishioka, I., Tannins and related compounds XC. 8-C-ascorbyl epigallocatechin 3-gallate and novel dimeric flavan-3-ols, oolonghomogisflavans A and B, from oolong tea (1989) Chemical & Pharmaceutical Bulletin, 37 (12), pp. 3255-3263; Hayat, K., Iqbal, H., Malik, U., Bilal, U., Mushtaq, S., Tea and its consumptions: Benefits and risks (2015) Critical Reviews in Food Science and Nutrition, 55 (7), pp. 939-994; Ho, C.T., Chen, Q., Shi, H., Zhang, K.Q., Rosen, R.T., Antioxidant effect of polyphenol extract prepared from various Chinese teas (1992) Preventive Medicine, 21 (4), pp. 520-525; Murakami, I., Nakamura, T., Ishibashi, Y., Shibuya, R., Ayano, E., Morita-Murase, Y., Kanazawa, H., Simultaneous determination of catechins and procyanidins in bottled tea drinks by LC/MS (2006) Chromatography, 27 (1), pp. 27-33; Ortwerth, B.J., Feather, M.S., Olesen, P.R., The precipitation of cross-linking of lens crystallins by ascorbic acid (1988) Experimental Eye Research, 47 (1), pp. 155-168; Sang, S., Lambert, J.D., Ho, C.T., Yang, C.S., The chemistry and biotransformation of tea constituents (2011) Pharmacological Research, 64, pp. 87-99; Sang, S., Lee, M.J., Hou, Z., Ho, C.T., Yang, C.S., Stability of tea polyphenol EGCG and formation of dimers and epimers under common experimental conditions (2005) Journal of Agricultural and Food Chemistry, 53 (24), pp. 9478-9484; Schimidt, H.L., Garcia, A., Martins, A., Mello-Carpes, P.B., Carpes, F.P., Green tea supplementation produces better neuroprotective effects than red and black tea in Alzheimer's-like rat model (2017) Food Research International, 100, pp. 442-448; Shpigelman, A., Israeli-Ler, G., Livney, Y.D., Thermally-induced protein-polyphenol co-assemblies; beta-lactoglobulin-based nanocomplexes as protective nanovehicles for EGCG (2010) Food Hydrocolloid, 24, pp. 735-743; Stewart, A.J., Mullen, W., Crozier, A., 0. On-line high-performance liquid chromatography analysis of the antioxidant activity of phenolic compounds in green and black tea (2005) Molecular Nutrition & Food Research, 49 (1), pp. 52-60; Su, Y.L., Leung, L.K., Huang, Y., Chen, Z.Y., Stability of tea theaflavins and catechins (2003) Food Chemistry, 83 (2), pp. 189-195; Wang, R., Zhou, W., Jiang, X., Reaction kinetics of degradation and epimerization of EGCG in aqueous system over a wide temperature range (2008) Journal of Agricultural and Food Chemistry, 56 (8), pp. 2694-2701; Watanabe, T., Nishiyama, R., Yamamoto, A., Nagai, S., Terabe, S., Simultaneous analysis of individual catechins, caffeine, and ascorbic acid in commercial canned green and black teas by micellar electrokinetic chromatography (1998) Analytical Sciences, 14, pp. 435-438; Xu, J.Z., Leung, L.K., Huang, Y., Chen, Z.Y., Epimerization of tea polyphenols in tea drinks (2003) Journal of the Science of Food and Agriculture, 83 (15), pp. 1617-1621; Xu, J.Z., Yeung, S.Y.V., Chang, Q., Huang, Y., Chen, Z.Y., Comparison of antioxidant activity and bioavailability of tea epicatechin with their epimers (2004) British Journal of Nutrition, 91, pp. 873-881; Zhu, Y., Zhao, Y., Wang, P., Ahmedna, M., Ho, C.T., Sang, S., Tea flavanols block advanced glycation of lens crystallins induced by dehydroascorbic acid (2015) Chemical Research in Toxicology, 28 (1), pp. 135-143

PY - 2018

Y1 - 2018

N2 - Catechins are the major bioactive compounds existing in tea leaves (Camellia sinensis). Dehydroascorbic acid is (DHAA) a reactive dicarbonyl species and previous studies have demonstrated that catechins could effectively trap DHAA to form ascorbyl adducts of catechins, especially epigallocatechin gallate (EGCG). Since catechins in the aqueous solution are unstable due to their structural features, ascorbic acid (AA) is usually added to bottled tea beverages to protect catechins. However, whether ascorbyl adducts of catechins are formed in bottled tea beverages remains unclear. In this study, formation of ascorbyl adducts of EGCG increased along with increased incubation time when EGCG and AA were dissolved in the aqueous solution. Next, 6C-DHAA-EGCG and 8C-DHAA-EGCG were detected in both green tea and oolong tea beverages, and their concentrations ranged from 0.23 to 1.95 µM and 0.28 to 1.97 µM, respectively. Furthermore, an 8C-ascorbyl adduct derived from gallocatechin gallate was also found in some tea beverages. © 2018 Elsevier Ltd

AB - Catechins are the major bioactive compounds existing in tea leaves (Camellia sinensis). Dehydroascorbic acid is (DHAA) a reactive dicarbonyl species and previous studies have demonstrated that catechins could effectively trap DHAA to form ascorbyl adducts of catechins, especially epigallocatechin gallate (EGCG). Since catechins in the aqueous solution are unstable due to their structural features, ascorbic acid (AA) is usually added to bottled tea beverages to protect catechins. However, whether ascorbyl adducts of catechins are formed in bottled tea beverages remains unclear. In this study, formation of ascorbyl adducts of EGCG increased along with increased incubation time when EGCG and AA were dissolved in the aqueous solution. Next, 6C-DHAA-EGCG and 8C-DHAA-EGCG were detected in both green tea and oolong tea beverages, and their concentrations ranged from 0.23 to 1.95 µM and 0.28 to 1.97 µM, respectively. Furthermore, an 8C-ascorbyl adduct derived from gallocatechin gallate was also found in some tea beverages. © 2018 Elsevier Ltd

KW - Ascorbic acid

KW - Ascorbyl adducts

KW - Epigallocatechin gallate

KW - Gallocatechin gallate

KW - Tea beverages

KW - Beverages

KW - Flavonoids

KW - Phenols

KW - Solutions

KW - Bioactive compounds

KW - Camellia sinensis

KW - Dehydroascorbic acid

KW - Gallate

KW - Incubation time

KW - Structural feature

KW - ascorbic acid

KW - catechin

KW - epigallocatechin gallate

KW - gallocatechin gallate

KW - unclassified drug

KW - aqueous solution

KW - Article

KW - drug determination

KW - high performance liquid chromatography

KW - incubation time

KW - tea

U2 - 10.1016/j.foodchem.2018.04.050

DO - 10.1016/j.foodchem.2018.04.050

M3 - Article

VL - 261

SP - 246

EP - 252

JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

ER -