Theaflavin-3-gallate specifically interacts with phosphatidylcholine, forming a precipitate resistant against the detergent action of bile salt

References

• Subramanian N, Venkatesh P, Ganguli S, et al. Role of polyphenol oxidase and peroxidase in the generation of black tea theaflavins. J Agric Food Chem. 1999;47:2571–2578.
   PubMed Web of Science ®Google Scholar
• Verloop AJW, Vincken JP, Gruppen H. Peroxidase can perform the hydroxylation step in the “oxidative cascade” during oxidation of tea catechins. J Agric Food Chem. 2016;64:8002–8009.
   Web of Science ®Google Scholar
• Tanaka T, Inoue K, Betsumiya Y, et al. Two types of oxidative dimerization of the black tea polyphenol theaflavin. J Agric Food Chem. 2001;49:5785–5789.
   PubMed Web of Science ®Google Scholar
• Tanaka T, Mine C, Inoue K, et al. Synthesis of theaflavin from epicatechin and epigallocatechin by plant homogenates and role of epicatechin quinone in the synthesis and degradation of theaflavin. J Agric Food Chem. 2002;50:2142–2148.
   PubMed Web of Science ®Google Scholar
• Henning SM, Fajardo-Lira C, Lee HW, et al. Catechin content of 18 teas and a green tea extract supplement correlates with the antioxidant capacity. Nutr Cancer. 2003;45:226–235.
   PubMed Web of Science ®Google Scholar
• Leung LK, Su Y, Chen R, et al. Theaflavins in black tea and catechins in green tea are equally effective antioxidants. J Nutr. 2001;131:2248–2251.
   PubMed Web of Science ®Google Scholar
• Yang Z, Tu Y, Xia H, et al. Suppression of free-radicals and protection against H2O2-induced oxidative damage in HPF-1 cell by oxidized phenolic compounds present in black tea. Food Chem. 2007;105:1349–1356.
   Web of Science ®Google Scholar
• Kobalka AJ, Keck RW, Jankun J. Synergistic anticancer activity of biologicals from green and black tea on DU 145 human prostate cancer cells. Cent Eur J Immunol. 2015;40:1–4.
   PubMed Web of Science ®Google Scholar
• GAO Y, RANKIN GO, TU Y, et al. Theaflavin-3, 3′-digallate decreases human ovarian carcinoma OVCAR-3 cell-induced angiogenesis via Akt and Notch-1 pathways, not via MAPK pathways. Int J Oncol. 2016;48:281–292.
   PubMed Web of Science ®Google Scholar
• Matsui T, Tanaka T, Tamura S, et al. α-glucosidase inhibitory profile of catechins and theaflavins. J Agric Food Chem. 2007;55:99–105.
   PubMed Web of Science ®Google Scholar
• Nishikawa K, Iwamoto Y, Kobayashi Y, et al. DNA methyltransferase 3a regulates osteoclast differentiation by coupling to an S-adenosylmethionine–producing metabolic pathway. Nat Med. 2015;21:281–287.
   PubMed Web of Science ®Google Scholar
• Davies MJ, Judd JT, Baer DJ, et al. Black tea consumption reduces total and LDL cholesterol in mildly hypercholesterolemic adults. J Nutr. 2003;133:3298S–3302S.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Asimi S, Wu K, et al. Black tea consumption and serum cholesterol concentration: Systematic review and meta-analysis of randomized controlled trials. Clin Nutr. 2015;34:612–619.
   PubMed Web of Science ®Google Scholar
• Vermeer MA, Mulder TP, Molhuizen HO. Theaflavins from black tea, especially theaflavin-3-gallate, reduce the incorporation of cholesterol into mixed micelles. J Agric Food Chem. 2008;56:12031–12036.
   PubMed Web of Science ®Google Scholar
• Ikeda I, Yamahira T, Kato M, et al. Black-tea polyphenols decrease micellar solubility of cholesterol in vitro and intestinal absorption of cholesterol in rats. J Agric Food Chem. 2010;58:8591–8595.
   PubMed Web of Science ®Google Scholar
• Miyata Y, Tanaka T, Tamaya K, et al. Cholesterol-lowering effect of black tea polyphenols, theaflavins, theasinensin a and thearubigins, in rats fed high fat diet. Food Sci Technol Res. 2011;17:585–588.
   Web of Science ®Google Scholar
• Woollett LA, Wang Y, Buckley DD, et al. Micellar solubilisation of cholesterol is essential for absorption in humans. Gut. 2006;55:197–204.
   PubMed Web of Science ®Google Scholar
• Alvaro D, Cantafora A, Attili AF, et al. Relationships between bile salts hydrophilicity and phospholipid composition in bile of various animal species. Comp Biochem Physiol B. 1986;83:551–554.
   PubMed Web of Science ®Google Scholar
• Kajiya K, Kumazawa S, Nakayama T. Steric effects on interaction of tea catechins with lipid bilayers. Biosci Biotechnol Biochem. 2001;65:2638–2643.
   PubMed Web of Science ®Google Scholar
• Kajiya K, Kumazawa S, Nakayama T. Effects of external factors on the interaction of tea catechins with lipid bilayers. Biosci Biotechnol Biochem. 2002;66:2330–2335.
   PubMed Web of Science ®Google Scholar
• Uekusa Y, Kamihira M, Nakayama T. Dynamic behavior of tea catechins interacting with lipid membranes as determined by NMR spectroscopy. J Agric Food Chem. 2007;55:9986–9992.
   PubMed Web of Science ®Google Scholar
• Ikeda I, Imasato Y, Sasaki E, et al. Tea catechins decrease micellar solubility and intestinal absorption of cholesterol in rats. Biochim Biophys Acta. 1992;1127:141–146.
   PubMed Web of Science ®Google Scholar
• Kim A, Chiu A, Barone MK, et al. Green tea catechins decrease total and low-density lipoprotein cholesterol: a systematic review and meta-analysis. J Am Diet Assoc. 2011;111:1720–1729.
   PubMed Web of Science ®Google Scholar
• Zheng XX, Xu YL, Li SH, et al. Green tea intake lowers fasting serum total and LDL cholesterol in adults: a meta-analysis of 14 randomized controlled trials. Am J Clin Nutr. 2011;94:601–610.
   PubMed Web of Science ®Google Scholar
• Kobayashi M, Nishizawa M, Inoue N, et al. Epigallocatechin gallate decreases the micellar solubility of cholesterol via specific interaction with phosphatidylcholine. J Agric Food Chem. 2014;62:2881–2890.
   PubMed Web of Science ®Google Scholar
• Ogawa K, Hirose S, Nagaoka S, et al. Interaction between tea polyphenols and bile acid inhibits micellar cholesterol solubility. J Agric Food Chem. 2016;64:204–209.
   PubMed Web of Science ®Google Scholar
• Matsuura K, Usui Y, Kan T, et al. Structural specificity of electric potentials in the coulometric-array analysis of catechins and theaflavins. J Clin Biochem Nutr. 2014;55:103–109.
   PubMed Web of Science ®Google Scholar
• Kaur S, Greaves P, Cooke DN, et al. Breast cancer prevention by green tea catechins and black tea theaflavins in the C3(1) SV40 T,t antigen transgenic mouse model is accompanied by increased apoptosis and a decrease in oxidative DNA adducts. J Agric Food Chem. 2007;55:3378–3385.
   PubMed Web of Science ®Google Scholar
• Adhikary A, Mohanty S, Lahiry L, et al. Theaflavins retard human breast cancer cell migration by inhibiting NF-kappaB via p53-ROS cross-talk. FEBS Lett. 2010;584:7–14.
   PubMed Web of Science ®Google Scholar
• Lin CL, Huang HC, Lin JK. Theaflavins attenuate hepatic lipid accumulation through activating AMPK in human HepG2 cells. J Lipid Res. 2007;48:2334–2343.
   PubMed Web of Science ®Google Scholar
• Saito A, Nakazato R, Suhara Y, et al. The impact of theaflavins on systemic-and microcirculation alterations: The murine and randomized feasibility trials. J Nutr Biochem. 2016;32:107–114.
   PubMed Web of Science ®Google Scholar
• Mulder TP, van Platerink CJ, Wijnand Schuyl PJ, et al. Analysis of theaflavins in biological fluids using liquid chromatography-electrospray mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001;760:271–279.
   PubMed Web of Science ®Google Scholar
• Wright LP, Mphangwe NIK, Nyirenda HE, et al. Analysis of the theaflavin composition in black tea (Camellia sinensis) for predicting the quality of tea produced in Central and Southern Africa. J Sci Food Agric. 2002;82:517–525.
   Web of Science ®Google Scholar
• Sakamoto A, Inoue H, Nakagawa M. Content of chemical constituents of 12 kinds of black tea. Nippon Shokuhin Kagaku Kogaku Kaishi. 2012;59:326–330.
   Web of Science ®Google Scholar
• Hara Y, Honda M. The inhibition of α-amylase by tea polyphenols. Agric Biol Chem. 1990;54:1939–1945.
   Web of Science ®Google Scholar
• Yamazaki T, Sagisaka M, Ikeda R, et al. The human bitter taste receptor hTAS2R39 is the primary receptor for the bitterness of theaflavins. Biosci Biotechnol Biochem. 2014;78:1753–1756.
   PubMed Web of Science ®Google Scholar
• Lei S, Xu D, Saeeduddin M, et al. Characterization of molecular structures of theaflavins and the interactions with bovine serum albumin. J Food Sci Technol. 2017;54:3421–3432.
   PubMed Web of Science ®Google Scholar
• Eckhardt ERM, Moschett A, Renooij W, et al. Asymmetric distribution of phosphatidylcholine and sphingomyelin between micellar and vesicular phases: potential implications for canalicular bile formation. J Lipid Res. 1999;40:2022–2033.
   PubMed Web of Science ®Google Scholar
• Njauw CW, Cheng CY, Ivanov VA, et al. Molecular interactions between lecithin and bile salts/acids in oils and their effects on reverse micellization. Langmuir. 2013;29:3879–3888.
   PubMed Web of Science ®Google Scholar