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Nutrient Physiology, Metabolism, and Nutrient-Nutrient Interactions

Of the Major Phenolic Acids Formed during Human Microbial Fermentation of Tea, Citrus, and Soy Flavonoid Supplements, Only 3,4-Dihydroxyphenylacetic Acid Has Antiproliferative Activity^1,2

Kun Gao, Anlong Xu, Cyrille Krul^*, Koen Venema^*, Yong Liu, Yantao Niu, Jinxiu Lu, Liath Bensoussan, Navindra P. Seeram, David Heber and Susanne M. Henning^,3

State Key Laboratory of Biocontrol, Department of Biochemistry and Center for Biopharmaceutical Research, College of Life Sciences, Sun Yatsen (Zhongshan) University, Guangzhou, China; ^* TNO Quality of Life, Business Unit Physiological Sciences, Zeist, NL; Center for Human Nutrition, David Geffen School of Medicine, University of California, Los Angeles, CA

³ To whom correspondence should be addressed. E-mail: shenning{at}mednet.ucla.edu.

ABSTRACT

Dietary flavonoids are poorly absorbed from the gastrointestinal tract. Colonic bacteria convert flavonoids into smaller phenolic acids (PA), which can be absorbed into the circulation and may contribute to the chemopreventive activity of the parent compounds. The purpose of our study was to determine whether flavonoids from green and black tea (GT, BT), citrus fruit with rutin (CF+R) and soy (S) supplements exposed to the same conditions in a dynamic in vitro model of the colon (TIM-2) will form the same phenolic acid products of microbial metabolism. About 600 mg of flavonoids from GT, BT, CF+R and S extracts were infused at t = 0 and 12 h into the TIM-2. Samples from the lumen and dialysate were collected at t = 0,4,8,12,16,24 and 28h. The flavonoid and PA concentrations were measured by HPLC and GC-MS. GT, BT, and CF+R formed 3-methoxy–4-hydroxyphenylacetic acid (3M4HPAA), 4-hydroxyphenyl acetic acid (4HPAA), 3,4-dihydroxyphenylacetic acid (3,4DHPAA), and 3-(3-hydroxyphenyl) propionic acid (3,3HPPA). BT flavonoids were also metabolized to 2,4,6-trihydroxybenzoic acid (2,4,6THBA) and CF+R flavonoids to 3-(4-hydroxy–3-methoxyphenyl) propionic acid (3,4H3MPPA), 3-hydroxyphenyl acetic acid (3HPAA) and a small amount of hippuric acid. After S infusion, we found 3M4HPAA and 4HPAA only. Among these phenolic acids, only 3,4DHPAA exhibited antiproliferative activity in prostate and colon cancer cells. 3,4DHPAA was significantly (P < 0.005) more inhibitory in colon cancer cells (HCT116) compared with an immortalized normal intestinal epithelial cell line (IEC6). In summary, fermentation by intestinal microbes of GT, BT, C+R, and S flavonoids resulted in the conversion to the same major phenolic acids.

KEY WORDS: • flavonoids • colonic fermentation • antiproliferative activity • phenolic acids

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