Advances in metabolism pathways of theaflavins: digestion, absorption, distribution and degradation

References

• Abbas, S., E. Karangwa, M. Bashari, K. Hayat, X. Hong, H. R. Sharif, and X. Zhang. 2015. Fabrication of polymeric nanocapsules from curcumin-loaded nanoemulsion templates by self-assembly. Ultrasonics Sonochemistry 23 :81–92. doi: 10.1016/j.ultsonch.2014.10.006.
   PubMed Web of Science ®Google Scholar
• Alotaibi, A., P. Bhatnagar, M. Najafzadeh, K. C. Gupta, and D. Anderson. 2013. Tea phenols in bulk and nanoparticle form modify DNA damage in human lymphocytes from colon cancer patients and healthy individuals treated in vitro with platinum-based chemotherapeutic drugs. Nanomedicine 8 (3):389–401. doi: 10.2217/nnm.12.126.
   PubMed Web of Science ®Google Scholar
• Bandyopadhyay, P., A. K. Ghosh, and C. Ghosh. 2012. Recent developments on polyphenol–protein interactions: Effects on tea and coffee taste, antioxidant properties and the digestive system. Food & Function 3 (6):592–605. doi: 10.1039/c2fo00006g.
   PubMed Web of Science ®Google Scholar
• Brodkorb, A., L. Egger, M. Alminger, P. Alvito, R. Assunção, S. Ballance, T. Bohn, C. Bourlieu-Lacanal, R. Boutrou, F. Carrière, et al. 2019. INFOGEST static in vitro simulation of gastrointestinal food digestion. Nature Protocols 14 (4):991–1014. doi: 10.1038/s41596-018-0119-1.
   PubMed Web of Science ®Google Scholar
• Chen, B. 2018a. Study on the absorption, metabolism and excretion of tea polyphenols and theaflavins in obeserats induced by high-fat diet. PhD diss., Anhui Agricultural University.
   Google Scholar
• Chen, J. 2018b. Evaluation of the control effect of 6.5% teaxanthin suspension on small green leafhoppers in tea plantations. Anhui Agricultural Science Bulletin 24 (02):49–51. doi: 10.16377/j.cnki.issn1007-7731.2018.02.019.
   Google Scholar
• Chen, H., and S. Sang. 2014. Biotransformation of tea polyphenols by gut microbiota. Journal of Functional Foods 7 :26–42. doi: 10.1016/j.jff.2014.01.013.
   Web of Science ®Google Scholar
• Chen, H., S. Hayek, J. R. Guzman, N. D. Gillitt, S. A. Ibrahim, C. Jobin, and S. Sang. 2012. The microbiota is essential for the generation of black tea theaflavins-derived metabolites. PLOS One 7 (12):e51001. doi: 10.1371/journal.pone.0051001.
   PubMed Web of Science ®Google Scholar
• Chen, H., T. A. Parks, X. Chen, N. D. Gillitt, C. Jobin, and S. Sang. 2011. Structural identification of mouse fecal metabolites of theaflavin 3,3′-digallate using liquid chromatography tandem mass spectrometry. Journal of Chromatography A 1218 (41):7297–306. doi: 10.1016/j.chroma.2011.08.056.
   PubMed Web of Science ®Google Scholar
• Chen, J., M. Ran, M. Wang, X. Liu, S. Liu, Z. Ruan, and N. Jin. 2022. Evaluation of antityrosinase activity and mechanism, antioxidation, and UV filter properties of theaflavin. Biotechnology and Applied Biochemistry 69 (3):951–62. doi: 10.1002/bab.2166.
   PubMed Web of Science ®Google Scholar
• Chen, J., Y. Zheng, S. Gong, Z. Zheng, J. Hu, L. Ma, X. Li, and H. Yu. 2023. Mechanisms of theaflavins against gout and strategies for improving the bioavailability. Phytomedicine 114 :154782. doi: 10.1016/j.phymed.2023.154782.
   PubMed Web of Science ®Google Scholar
• Ding, Y., L. Zou, C. Lu, H. Tong, and B. Chen. 2018. In Situ enzymatic synthesis and purification of theaflavin‐3,3′‐digallate monomer and incorporation into nanoliposome. International Journal of Food Science & Technology 53 (11):2552–9. doi: 10.1111/ijfs.13849.
   Web of Science ®Google Scholar
• Esperón-Rojas, A. A., R. Baeza-Jiménez, D. Santos-Luna, L. D. C. Velasco-Rodríguez, L. R. Ochoa-Rodríguez, and H. S. García. 2020. Bioavailability of curcumin in nanoemulsions stabilized with mono and diacylglycerols structured with conjugated linoleic acid and n-3 fatty acids. Biocatalysis and Agricultural Biotechnology 26 :101638. doi: 10.1016/j.bcab.2020.101638.
   Web of Science ®Google Scholar
• Fang, M., J. Wang, S. Fang, and X. Zuo. 2023. Fabrication of carboxymethyl chitosan films for cheese packaging containing gliadin-carboxymethyl chitosan nanoparticles co-encapsulating natamycin and theaflavins. International Journal of Biological Macromolecules 246 :125685. doi: 10.1016/j.ijbiomac.2023.125685.
   PubMed Web of Science ®Google Scholar
• Fatima, M., R. K. Kesharwani, K. Misra, and S. I. Rizvi. 2013. Protective effect of theaflavin on erythrocytes subjected to in vitro oxidative stress. Biochemistry Research International 2013:649759–7. doi: 10.1155/2013/649759.
   PubMedGoogle Scholar
• Flowers, S. A., S. Bhat, and J. C. Lee. 2020. Potential implications of gut microbiota in drug pharmacokinetics and bioavailability. Pharmacotherapy 40 (7):704–12. doi: 10.1002/phar.2428.
   PubMed Web of Science ®Google Scholar
• Ganguly, S., T. K. G, S. Mantha, and K. Panda. 2016. Simultaneous determination of black tea-derived catechins and theaflavins in tissues of tea consuming animals using ultra-performance liquid-chromatography tandem mass spectrometry. PLOS One 11 (10):e0163498. doi: 10.1371/journal.pone.0163498.
   PubMed Web of Science ®Google Scholar
• Gómez-Mejía, E., N. Rosales-Conrado, M. E. León-González, A. Valverde, and Y. Madrid. 2022. A combined analytical-chemometric approach for the in vitro determination of polyphenol bioaccessibility by simulated gastrointestinal digestion. Analytical and Bioanalytical Chemistry 414 (8):2739–55. doi: 10.1007/s00216-022-03922-x.
   PubMed Web of Science ®Google Scholar
• Gu, L., C. Pan, Y. Su, R. Zhang, H. Xiao, D. J. McClements, and Y. Yang. 2018. In vitro bioavailability, cellular antioxidant activity, and cytotoxicity of β-carotene-loaded emulsions stabilized by catechin–egg white protein conjugates. Journal of Agricultural and Food Chemistry 66 (7):1649–57. doi: 10.1021/acs.jafc.7b05909.
   PubMed Web of Science ®Google Scholar
• He, H. 2017. Research progress on theaflavins: Efficacy, formation, and preparation. Food & Nutrition Research 61 (1):1344521. doi: 10.1080/16546628.2017.1344521.
   PubMedGoogle Scholar
• Henning, S. M., P. Wang, J. W. Said, M. Huang, T. Grogan, D. Elashoff, C. L. Carpenter, D. Heber, and W. J. Aronson. 2015. Randomized clinical trial of brewed green and black tea in men with prostate cancer prior to prostatectomy. The Prostate 75 (5):550–9. doi: 10.1002/pros.22943.
   PubMed Web of Science ®Google Scholar
• Henning, S. M., W. Aronson, Y. Niu, F. Conde, N. H. Lee, N. P. Seeram, R. P. Lee, J. Lu, D. M. Harris, A. Moro, et al. 2006. Tea polyphenols and theaflavins are present in prostate tissue of humans and mice after green and black tea consumption. The Journal of Nutrition 136 (7):1839–43. doi: 10.1093/jn/136.7.1839.
   PubMed Web of Science ®Google Scholar
• Imam, S. S., and S. Agarwal. 2021. A pragmatic approach to treat lung cancer through loading theaflavin -3,3′-digallate and epigallocatechin gallate in spanlastic. Asian Journal of Pharmaceutical and Clinical Research 14 (11): 1–8. doi: 10.22159/ajpcr.2021.v14i11.42757.
   Google Scholar
• Jhoo, J. W., C. Y. Lo, S. Li, S. Sang, C. Y. Ang, T. M. Heinze, and C. T. Ho. 2005. Stability of Black Tea Polyphenol, Theaflavin, and Identification of Theanaphthoquinone as Its Major Radical Reaction Product. Journal of Agricultural and Food Chemistry 53 (15):6146–50. doi: 10.1021/jf050662d.
   PubMed Web of Science ®Google Scholar
• Jiang, Y., T. Zheng, W. Jin, Y. Shi, and Q. Huang. 2022. Enhancing Intestinal Permeability of Theaflavin-3,3′-Digallate by Chitosan–Caseinophosphopeptides Nanocomplexes. Journal of agricultural and food chemistry 70 (6):2029–41. doi: 10.1021/acs.jafc.1c07382.
   PubMed Web of Science ®Google Scholar
• Kadowaki, M., N. Sugihara, T. Tagashira, K. Terao, and K. Furuno. 2010. Presence or absence of a gallate moiety on catechins affects their cellular transport. The Journal of Pharmacy and Pharmacology 60 (9):1189–95. doi: 10.1211/jpp.60.9.0011.
   Web of Science ®Google Scholar
• Li, Y., Q. Gan, L. Li, D. Tian, J. Xie, Z. Luo,Y. Lu, and P. Wu. 2022. Preparation of theaflavin-3,3′-digallate-chitosan nanoemulsion and its characteristics. China Food Additives 33 (09):151–8. doi: 10.19804/j.issn1006-2513.2022.09.021.
   Google Scholar
• Li, H., J. P. Limenitakis, T. Fuhrer, M. B. Geuking, M. A. Lawson, M. Wyss, S. Brugiroux, I. Keller, J. A. Macpherson, S. Rupp, et al. 2015. The outer mucus layer hosts a distinct intestinal microbial niche. Nature Communications 6 (1):8292. doi: 10.1038/ncomms9292.
   PubMedGoogle Scholar
• Li, L. 2019. Analysis of patent for the application of theaflavin in the field of medicine. Modern Agriculture Research 11:101–2. doi: 10.19704/j.cnki.xdnyyj.2019.11.042.
   Google Scholar
• Liang, H., X. Yang, S. Zhang, R. Tan, Y. Tu, J. Kong, X. Chen, and Y. Gao. 2022. Optimization of a tannase-assisted process for obtaining teas rich in theaflavins from Camellia sinensis leaves. Food Chemistry: X 13 :100203. doi: 10.1016/j.fochx.2022.100203.
   PubMedGoogle Scholar
• Liu, Z., W. J. de Bruijn, M. E. Bruins, and J. P. Vincken. 2021. Microbial metabolism of theaflavin-3,3′-digallate and its gut microbiota composition modulatory effects. Journal of Agricultural and Food Chemistry 69 (1):232–45. doi: 10.1021/acs.jafc.0c06622.
   PubMed Web of Science ®Google Scholar
• Su, Ya Lun, L. K. Leung, Y. Huang, and Z.-Y. Chen. 2003. Stability of Tea Theaflavins and Catechins. Food Chemistry 83 (2):189–95. doi: 10.1016/S0308-8146(03)00062-1.
   Web of Science ®Google Scholar
• Ma, H., Y. Hu, B. Zhang, Z. Shao, E. Roura, and S. Wang. 2022. Tea polyphenol – gut microbiota interactions: Hints on improving the metabolic syndrome in a multi-element and multi-target manner. Food Science and Human Wellness 11 (1):11–21. doi: 10.1016/j.fshw.2021.07.002.
   Google Scholar
• Mao, J., J. J. Fu, X. Qi, Y. W. Chen, and B. Zhang. 2023. Effect of theaflavins on the quality of large yellow croaker (Larimichthys Crocea) during refrigerated storage. Journal of the Science of Food and Agriculture 103 (12):6033–43. doi: 10.1002/jsfa.12671.
   PubMed Web of Science ®Google Scholar
• McClements, D. J. 2020. Advances in nanoparticle and microparticle delivery systems for increasing the dispersibility, stability, and bioactivity of phytochemicals. Biotechnology Advances 38:107287. doi: 10.1016/j.biotechadv.2018.08.004.
   PubMed Web of Science ®Google Scholar
• McClements, D. J. 2021. Advances in edible nanoemulsions: Digestion, bioavailability, and potential toxicity. Progress in Lipid Research 81 :101081. doi: 10.1016/j.plipres.2020.101081.
   PubMed Web of Science ®Google Scholar
• McClements, D. J., F. Li, and H. Xiao. 2015. The nutraceutical bioavailability classification scheme: Classifying nutraceuticals according to factors limiting their oral bioavailability. Annual Review of Food Science and Technology 6 (1):299–327. doi: 10.1146/annurev-food-032814-014043.
   PubMedGoogle Scholar
• Mhatre, S., T. Srivastava, S. Naik, and V. Patravale. 2021. Antiviral activity of green tea and black tea polyphenols in prophylaxis and treatment of COVID-19: A review. Phytomedicine 85 :153286. doi: 10.1016/j.phymed.2020.153286.
   PubMed Web of Science ®Google Scholar
• Miao, M., H. Jiang, B. Jiang, Y. Li, S. W. Cui, and Z. Jin. 2013. Elucidation of structural difference in theaflavins for modulation of starch digestion. Journal of Functional Foods 5 (4):2024–9. doi: 10.1016/j.jff.2013.09.021.
   Web of Science ®Google Scholar
• Minekus, M., M. Alminger, P. Alvito, S. Ballance, T. Bohn, C. Bourlieu, F. Carrière, R. Boutrou, M. Corredig, D. Dupont, et al. 2014. A standardised static in vitro digestion method suitable for food – an international consensus. Food & Function 5 (6):1113–24. doi: 10.1039/C3FO60702J.
   PubMed Web of Science ®Google Scholar
• Mulder, T. P., C. J. van Platerink, P. W. Schuyl, and J. M. van Amelsvoort. 2001. Analysis of theaflavins in biological fluids using liquid chromatography–electrospray mass spectrometry. Journal of Chromatography. B, Biomedical Sciences and Applications 760 (2):271–9. doi: 10.1016/S0378-4347(01)00285-7.
   PubMedGoogle Scholar
• Nakamura, N., H. C. Lin, C. S. McSweeney, R. I. Mackie, and H. R. Gaskins. 2010. Mechanisms of microbial hydrogen disposal in the human colon and implications for health and disease. Annual Review of Food Science and Technology 1 (1):363–95. doi: 10.1146/annurev.food.102308.124101.
   PubMedGoogle Scholar
• Parthasarathi, S., S. P. Muthukumar, and C. Anandharamakrishnan. 2016. The influence of droplet size on the stability, in vivo digestion, and oral bioavailability of vitamin E emulsions. Food & Function 7 (5):2294–302. doi: 10.1039/C5FO01517K.
   PubMed Web of Science ®Google Scholar
• Pereira-Caro, G., J. M. Moreno-Rojas, N. Brindani, D. Del Rio, M. E. Lean, Y. Hara, and A. Crozier. 2017. Bioavailability of black tea theaflavins: Absorption, metabolism, and colonic catabolism. Journal of Agricultural and Food Chemistry 65 (26):5365–74. doi: 10.1021/acs.jafc.7b01707.
   PubMed Web of Science ®Google Scholar
• Qu, F., Z. Ai, S. Liu, H. Zhang, Y. Chen, Y. Wang, and D. Ni. 2021. Study on mechanism of low bioavailability of black tea theaflavins by using Caco-2 cell monolayer. Drug delivery 28 (1):1737–47. doi: 10.1080/10717544.2021.1949074.
   PubMed Web of Science ®Google Scholar
• Shi, M., Y. Lu, J. Wu, Z. Zheng, C. Lv, J. Ye, S. Qin, and C. Zeng. 2022. Beneficial effects of theaflavins on metabolic syndrome: From molecular evidence to gut microbiome. International Journal of Molecular Sciences 23 (14):7595. doi: 10.3390/ijms23147595.
   PubMed Web of Science ®Google Scholar
• Shori, A., P. Muniandy, and A. S. Baba. 2021. Changes in phenolic compounds profiles in tea extracts and the composition of these phenolic compounds in yogurt. Recent Patents on Food, Nutrition & Agriculture 12 (1):36–44. doi: 10.2174/2212798411999201123205022.
   PubMedGoogle Scholar
• Sun, L., Y. Su, K. Hu, D. Li, H. Guo, and Z. Xie. 2023. Microbial-transferred metabolites of black tea theaflavins by human gut microbiota and their impact on antioxidant capacity. Molecules 28 (15):5871. doi: 10.3390/molecules28155871.
   PubMed Web of Science ®Google Scholar
• Tanaka, T., Y. M. Kirita, S. Miyata, Y. Abe, M. Tagashira, T. Kanda, and M. Maeda-Yamamoto. 2013. O-methylated theaflavins suppress the intracellular accumulation of triglycerides from terminally differentiated human visceral adipocytes. Journal of Agricultural and Food Chemistry 61 (51):12634–9. doi: 10.1021/jf404446h.
   PubMed Web of Science ®Google Scholar
• Tabanelli, R., S. Brogi, and V. Calderone. 2021. Improving curcumin bioavailability: Current strategies and future perspectives. Pharmaceutics 13 (10):1715. doi: 10.3390/pharmaceutics13101715.
   PubMed Web of Science ®Google Scholar
• Takino, Y., H. Imagawa, H. Horikawa, and A. Tanaka. 1964. Studies on the mechanism of the oxidation of tea leaf catechins: Part III. Formation of a reddish orange pigment and its spectral relationship to some benzotropolone derivatives. Agricultural and Biological Chemistry 28 (1):64–71. doi: 10.1080/00021369.1964.10858200.
   Web of Science ®Google Scholar
• Tan, R., X. Yang, S. Zhang, J. Kong, Y. Tu, and H. Liang. 2013. A theaflavin health food or medicine and its preparation method.
   Google Scholar
• Tomas, M., Y. Wen, W. Liao, L. Zhang, C. Zhao, D. J. McClements, N. Elifsu, B. Mustafa, A. Resat, and E. Capanoglu. 2024. Recent progress in promoting the bioavailability of polyphenols in plant-based foods. Critical Reviews in Food Science and Nutrition. doi: 10.1080/10408398.2024.2336051.
   Web of Science ®Google Scholar
• Tran, V. N., J. Viktorová, and T. Ruml. 2020. Mycotoxins: Biotransformation and bioavailability assessment using Caco-2 cell monolayer. Toxins 12 (10):628. doi: 10.3390/toxins12100628.
   PubMed Web of Science ®Google Scholar
• Wang, B., Y. P. Timilsena, E. Blanch, B. Wang, and B. Adhikari. 2019. Lactoferrin: Structure, function, denaturation and digestion. Critical Reviews in Food Science and Nutrition 59 (4):580–96. doi: 10.1080/10408398.2017.1381583.
   PubMed Web of Science ®Google Scholar
• Wang, J., Y. Qin, J. Jiang, H. Shan, C. Zhao, and S. Li. 2023. The effect of theaflavins on the gut microbiome and metabolites in diabetic mice. Foods 12 (20):3865. doi: 10.3390/foods12203865.
   PubMed Web of Science ®Google Scholar
• Wang, M., J. Xu, T. Han, and L. Tang. 2021. Effects of theaflavins on the structure and function of bovine lactoferrin. Food Chemistry 338 :128048. doi: 10.1016/j.foodchem.2020.128048.
   PubMed Web of Science ®Google Scholar
• Wu, G. 2020. Enzymatic synthesis, in vitro simulated digestion, anti-inflammation and antioxidation of theaflavins digallate. PhD diss., Nanjing Agricultural University.
   Google Scholar
• Wu, Y.-H., R. Kuraji, Y. Taya, H. Ito, and Y. Numabe. 2018. Effects of theaflavins on tissue inflammation and bone resorption on experimental periodontitis in rats. Journal of Periodontal Research 53 (6):1009–19. doi: 10.1111/jre.12600.
   PubMed Web of Science ®Google Scholar
• Xia, G. 2016. Separation and analysis of representative catechins and theaflavins and their attenuation effects of metabolic syndrome in female db/db mice. PhD diss., Zhejiang University.
   Google Scholar
• Ye, Q., T. Li, J. Li, L. Liu, X. Dou, and X. Zhang. 2020. Development and evaluation of tea polyphenols loaded water in oil emulsion with Zein as stabilizer. Journal of Drug Delivery Science and Technology 56 :101528. doi: 10.1016/j.jddst.2020.101528.
   Web of Science ®Google Scholar
• Yu, S. 2012. Pharmacokinetics of theaflavin-3-3′-digallate in rats. PhD diss., Southwest University.
   Google Scholar
• Zhang, S., C. Ohland, C. Jobin, and S. Sang. 2021. Black tea theaflavin detoxifies metabolic toxins in the intestinal tract of mice. Molecular Nutrition & Food Research 65 (4):e2000887. doi: 10.1002/mnfr.202000887.
   PubMed Web of Science ®Google Scholar
• Zhang, S., C. Ohland, C. Jobin, and S. Sang. 2022. Degradation of black tea theaflavin through C-ring cleavage by gut microbiota. Food Science and Human Wellness 11 (3):598–605. doi: 10.1016/j.fshw.2021.12.016.
   Google Scholar
• Zhu, Y. 2022. Isolation and purification of theaflavins and their antioxidative and α-glucosidase inhibition activities. PhD diss., Anhui Polytechnic University.
   Google Scholar