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Curcuminoid Demethylation as an Alternative Metabolism by Human Intestinal Microbiota

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Metalloenzyme Research Group and Department of Integrative Plant Science, Chung-Ang University, Anseong 17546, Korea
*(J.H.) Phone: +82 31 670 4830. Fax: +82 31 675 1381. E-mail: [email protected]
Cite this: J. Agric. Food Chem. 2017, 65, 16, 3305–3310
Publication Date (Web):April 12, 2017
https://doi.org/10.1021/acs.jafc.7b00943
Copyright © 2017 American Chemical Society
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    Curcumin and other curcuminoids from Curcuma longa are important bioactive compounds exhibiting various pharmacological activities. In addition to the known reductive metabolism of curcuminoids, an alternative biotransformation of curcuminoids by human gut microbiota is reported herein. A curcuminoid mixture, composed of curcumin (1), demethoxycurcumin (2), and bisdemethoxycurcumin (3), was metabolized by the human intestinal bacterium Blautia sp. MRG-PMF1. 1 and 2 were converted to new metabolites by the methyl aryl ether cleavage reaction. Two metabolites, demethylcurcumin (4) and bisdemethylcurcumin (5), were sequentially produced from 1, and demethyldemethoxycurcumin (6) was produced from 2. Until now, sequential reduction of the heptadienone backbone of curcuminoids was the only known metabolism to occur in the human intestine. In this study, a new intestinal metabolism of curcuminoids was discovered. Demethylation of curcuminoids produced three new colonic metabolites that were already known as promising synthetic curcumin analogues. The results could explain the observed beneficial effects of turmeric.

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    • Curcuminoid biotransformation by the three different mixed cell cultures (Figure S1), bisdemethoxycurcumin (3) biotransformation by Blautia sp. MRG-PMF1 (Figure S2), and ESI-MS spectra of curcuminoids and the metabolites (Figure S3) (PDF)

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    4. Akil I. Joseph, Paula B. Luis, Claus Schneider. A Curcumin Degradation Product, 7-Norcyclopentadione, Formed by Aryl Migration and Loss of a Carbon from the Heptadienedione Chain. Journal of Natural Products 2018, 81 (12) , 2756-2762. https://doi.org/10.1021/acs.jnatprod.8b00822
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    6. Sanjay Basak, Kota Sri Naga Hridayanka, Asim K. Duttaroy. Bioactives and their roles in bone metabolism of osteoarthritis: evidence and mechanisms on gut-bone axis. Frontiers in Immunology 2024, 14 https://doi.org/10.3389/fimmu.2023.1323233
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    8. Huynh Thi Ngoc Mi, Santipap Chaiyasarn, Heji Kim, Jaehong Han. C -Glycoside-Metabolizing Human Gut Bacterium, Dorea sp. MRG-IFC3. Journal of Microbiology and Biotechnology 2023, 33 (12) , 1606-1614. https://doi.org/10.4014/jmb.2308.08021
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    11. Nageswaran Sivalingam, Thennavan Ulaganathan, Ganshyam Jayakumar, Siddarth Venkatt, Aadhavan Balakumar, Sruthi Sritharan. Unraveling the Chemistry of Curcumin for Colon Cancer Prevention and Treatment. 2023, 61-115. https://doi.org/10.4018/978-1-6684-9463-9.ch003
    12. Benchi Cai, Lifan Zhong, Qitong Wang, Wendi Xu, Xi Li, Tao Chen. Curcumin alleviates 1-methyl- 4-phenyl- 1,2,3,6-tetrahydropyridine- induced Parkinson’s disease in mice via modulating gut microbiota and short-chain fatty acids. Frontiers in Pharmacology 2023, 14 https://doi.org/10.3389/fphar.2023.1198335
    13. Linjiang Zhu, Yuting Xue, Jiacheng Feng, Yuxin Wang, Yuele Lu, Xiaolong Chen. Tetrahydrocurcumin as a stable and highly active curcumin derivative: A review of synthesis, bioconversion, detection and application. Food Bioscience 2023, 53 , 102591. https://doi.org/10.1016/j.fbio.2023.102591
    14. Biying Luo, Yuxi Wen, Fangting Ye, Yanglin Wu, Na Li, Muhammad Salman Farid, Zhengxin Chen, Hesham R. El-Seedi, Chao Zhao. Bioactive phytochemicals and their potential roles in modulating gut microbiota. Journal of Agriculture and Food Research 2023, 12 , 100583. https://doi.org/10.1016/j.jafr.2023.100583
    15. Rossana Cuciniello, Francesco Di Meo, Stefania Filosa, Stefania Crispi, Paolo Bergamo. The Antioxidant Effect of Dietary Bioactives Arises from the Interplay between the Physiology of the Host and the Gut Microbiota: Involvement of Short-Chain Fatty Acids. Antioxidants 2023, 12 (5) , 1073. https://doi.org/10.3390/antiox12051073
    16. Andrea Ticinesi, Antonio Nouvenne, Nicoletta Cerundolo, Alberto Parise, Tiziana Meschi. Accounting Gut Microbiota as the Mediator of Beneficial Effects of Dietary (Poly)phenols on Skeletal Muscle in Aging. Nutrients 2023, 15 (10) , 2367. https://doi.org/10.3390/nu15102367
    17. Wei Shen, Yanlin Tao, Fang Zheng, Houyuan Zhou, Hui Wu, Hailian Shi, Fei Huang, Xiaojun Wu. The alteration of gut microbiota in venlafaxine-ameliorated chronic unpredictable mild stress-induced depression in mice. Behavioural Brain Research 2023, 446 , 114399. https://doi.org/10.1016/j.bbr.2023.114399
    18. Tingting Qin, Xiuying Chen, Jiahui Meng, Qianqian Guo, Shan Xu, Shanshan Hou, Ziqiao Yuan, Wenzhou Zhang. The role of curcumin in the liver-gut system diseases: from mechanisms to clinical therapeutic perspective. Critical Reviews in Food Science and Nutrition 2023, 21 , 1-30. https://doi.org/10.1080/10408398.2023.2204349
    19. Helen-Lissette Alvarado, David Limón, Ana-Cristina Calpena-Campmany, Mireia Mallandrich, Laura Rodríguez-Cid, Núria Aliaga-Alcalde, Arántzazu González-Campo, Lluïsa Pérez-García. Intrinsic Permeation and Anti-Inflammatory Evaluation of Curcumin, Bisdemethoxycurcumin and Bisdemethylcurcumin by a Validated HPLC-UV Method. International Journal of Molecular Sciences 2023, 24 (7) , 6640. https://doi.org/10.3390/ijms24076640
    20. Nurul Iman Aminudin, Nurul Aqilah Amran, Zaima Azira Zainal Abidin, Deny Susanti. Biotransformation of curcumin and structure–activity relationship (SAR) of its analogues: A systematic review. Biocatalysis and Biotransformation 2023, 41 (1) , 1-14. https://doi.org/10.1080/10242422.2022.2073227
    21. Hao-Yu Yang, Lin Han, Yi-Qun Lin, Tao Li, Yu Wei, Lin-Hua Zhao, Xiao-Lin Tong. Probiotic Fermentation of Herbal Medicine: Progress, Challenges, and Opportunities. The American Journal of Chinese Medicine 2023, 51 (05) , 1105-1126. https://doi.org/10.1142/S0192415X23500519
    22. 雯 吴. Exploring the Correlation between Tobacco Exposure and Human Intestinal Flora. Advances in Microbiology 2023, 12 (02) , 71-82. https://doi.org/10.12677/AMB.2023.122009
    23. Luciano da Silva Lopes, Suyanne Kássia Soares Pereira, Layana Karine Farias Lima. Pharmacokinetics and Pharmacodynamics of Curcumin. 2023, 3-19. https://doi.org/10.1007/978-981-99-7731-4_1
    24. K. Nanavati, K. Rutherfurd-Markwick, S. J. Lee, N. C. Bishop, A. Ali. Effect of curcumin supplementation on exercise-induced muscle damage: a narrative review. European Journal of Nutrition 2022, 61 (8) , 3835-3855. https://doi.org/10.1007/s00394-022-02943-7
    25. Aleksandra Pituch-Zdanowska, Łukasz Dembiński, Aleksandra Banaszkiewicz. Old but Fancy: Curcumin in Ulcerative Colitis—Current Overview. Nutrients 2022, 14 (24) , 5249. https://doi.org/10.3390/nu14245249
    26. Natalija Atanasova-Panchevska, Radoslav Stojchevski, Nikola Hadzi-Petrushev, Vadim Mitrokhin, Dimiter Avtanski, Mitko Mladenov. Antibacterial and Antiviral Properties of Tetrahydrocurcumin-Based Formulations: An Overview of Their Metabolism in Different Microbiotic Compartments. Life 2022, 12 (11) , 1708. https://doi.org/10.3390/life12111708
    27. Huynh Thi Ngoc Mi, Santipap Chaiyasarn, Bekir Engin Eser, Steven R. Susanto Tan, Supawadee Burapan, Jaehong Han, . Allyl Aryl Ether Cleavage by Blautia sp. MRG-PMF1 Cocorrinoid O -Demethylase. Microbiology Spectrum 2022, 10 (5) https://doi.org/10.1128/spectrum.03305-22
    28. Umang kumar Shah, Deep Patel, Drashti Dalsania, Mehul Patel, Meghana Patel, Ashish Patel, Nilay Solanki, Swayamprakash Patel, Samir Patel. Review on Analytical Methodologies, Chemical and Therapeutic Perspectives of Curcumin: A Ubiquitous Natural Molecule. Current Pharmaceutical Analysis 2022, 18 (8) , 777-794. https://doi.org/10.2174/1573412918666220620154659
    29. Dong-Woo Lim, Jing-Hua Wang. Gut Microbiome: The Interplay of an “Invisible Organ” with Herbal Medicine and Its Derived Compounds in Chronic Metabolic Disorders. International Journal of Environmental Research and Public Health 2022, 19 (20) , 13076. https://doi.org/10.3390/ijerph192013076
    30. Yucui Zhao, Xinqin Zhong, Junyuan Yan, Congying Sun, Xin Zhao, Xiaoying Wang. Potential roles of gut microbes in biotransformation of natural products: An overview. Frontiers in Microbiology 2022, 13 https://doi.org/10.3389/fmicb.2022.956378
    31. Juntao Kan, Feng Wu, Feijie Wang, Jianheng Zheng, Junrui Cheng, Yuan Li, Yuexin Yang, Jun Du. Phytonutrients: Sources, bioavailability, interaction with gut microbiota, and their impacts on human health. Frontiers in Nutrition 2022, 9 https://doi.org/10.3389/fnut.2022.960309
    32. G. V. Anjana, M. K. Kathiravan. Antimicrobial Activity of Curcumin and Deuterated Curcumin. Journal of Natural Remedies 2022, , 424-431. https://doi.org/10.18311/jnr/2022/29686
    33. Wuwen Feng, Juan Liu, Hao Cheng, Dandan Zhang, Yuzhu Tan, Cheng Peng. Dietary compounds in modulation of gut microbiota-derived metabolites. Frontiers in Nutrition 2022, 9 https://doi.org/10.3389/fnut.2022.939571
    34. Sophie Verstraeten, Valentin Sencio, Audrey Raise, Eugénie Huillet, Séverine Layec, Lucie Deruyter, Séverine Heumel, Sandrine Auger, Véronique Robert, Philippe Langella, Laurent Beney, François Trottein, Muriel Thomas. Description of a Newly Isolated Blautia faecis Strain and Its Benefit in Mouse Models of Post-Influenza Secondary Enteric and Pulmonary Infections. Nutrients 2022, 14 (7) , 1478. https://doi.org/10.3390/nu14071478
    35. Mohamed Samir Darwish, Longxin Qiu, Mohamed A. Taher, Ahmed A. Zaki, Noha A. Abou-Zeid, Dawood H. Dawood, Ola M. A. K. Shalabi, Ebtihal Khojah, Asmaa A. Elawady. Health Benefits of Postbiotics Produced by E. coli Nissle 1917 in Functional Yogurt Enriched with Cape Gooseberry (Physalis peruviana L.). Fermentation 2022, 8 (3) , 128. https://doi.org/10.3390/fermentation8030128
    36. Lu Yan, Min-Song Guo, Yue Zhang, Lu Yu, Jian-Ming Wu, Yong Tang, Wei Ai, Feng-Dan Zhu, Betty Yuen-Kwan Law, Qi Chen, Chong-Lin Yu, Vincent Kam-Wai Wong, Hua Li, Mao Li, Xiao-Gang Zhou, Da-Lian Qin, An-Guo Wu, . Dietary Plant Polyphenols as the Potential Drugs in Neurodegenerative Diseases: Current Evidence, Advances, and Opportunities. Oxidative Medicine and Cellular Longevity 2022, 2022 , 1-40. https://doi.org/10.1155/2022/5288698
    37. Tugba Ozdal, Senem Kamiloglu. Polyphenols, Bioavailability and Potency. 2022, 3-19. https://doi.org/10.1016/B978-0-12-819265-8.00061-9
    38. R. García-Villalba, A. González-Sarrías, J.A. Giménez-Bastida, M.V. Selma, J.C. Espín, F.A. Tomás-Barberán. Metabolism of Dietary (Poly)phenols by the Gut Microbiota. 2022, 149-175. https://doi.org/10.1016/B978-0-12-819265-8.00091-7
    39. Annaelle Hip Kam, Vidushi S. Neergheen. Nutraceutical and phytopharmaceuticals in immune health. 2022, 445-475. https://doi.org/10.1016/B978-0-12-821232-5.00024-0
    40. Soudeh Ghafouri-Fard, Hamed Shoorei, Zahra Bahroudi, Bashdar Mahmud Hussen, Seyedeh Fahimeh Talebi, Mohammad Taheri, Seyed Abdulmajid Ayatollahi. Nrf2-Related Therapeutic Effects of Curcumin in Different Disorders. Biomolecules 2022, 12 (1) , 82. https://doi.org/10.3390/biom12010082
    41. Lina Wang, Mengxue Gao, Guangbo Kang, He Huang. The Potential Role of Phytonutrients Flavonoids Influencing Gut Microbiota in the Prophylaxis and Treatment of Inflammatory Bowel Disease. Frontiers in Nutrition 2021, 8 https://doi.org/10.3389/fnut.2021.798038
    42. Kabelo Mokgalaboni, Yonela Ntamo, Khanyisani Ziqubu, Tawanda M. Nyambuya, Bongani B. Nkambule, Sithandiwe E. Mazibuko-Mbeje, Kwazikwakhe B. Gabuza, Nireshni Chellan, Luca Tiano, Phiwayinkosi V. Dludla. Curcumin supplementation improves biomarkers of oxidative stress and inflammation in conditions of obesity, type 2 diabetes and NAFLD: updating the status of clinical evidence. Food & Function 2021, 12 (24) , 12235-12249. https://doi.org/10.1039/D1FO02696H
    43. Gerwyn Morris, Elizabeth Gamage, Nikolaj Travica, Michael Berk, Felice N. Jacka, Adrienne O'Neil, Basant K. Puri, Andre F. Carvalho, Chiara C. Bortolasci, Ken Walder, Wolfgang Marx. Polyphenols as adjunctive treatments in psychiatric and neurodegenerative disorders: Efficacy, mechanisms of action, and factors influencing inter-individual response. Free Radical Biology and Medicine 2021, 172 , 101-122. https://doi.org/10.1016/j.freeradbiomed.2021.05.036
    44. Farah J. Hashim, Sukanda Vichitphan, Jaehong Han, Kanit Vichitphan. Alternative Approach for Specific Tyrosinase Inhibitor Screening: Uncompetitive Inhibition of Tyrosinase by Moringa oleifera. Molecules 2021, 26 (15) , 4576. https://doi.org/10.3390/molecules26154576
    45. Marzena Jabczyk, Justyna Nowak, Bartosz Hudzik, Barbara Zubelewicz-Szkodzińska. Curcumin and Its Potential Impact on Microbiota. Nutrients 2021, 13 (6) , 2004. https://doi.org/10.3390/nu13062004
    46. Alessandra Berry, Barbara Collacchi, Roberta Masella, Rosaria Varì, Francesca Cirulli. Curcuma Longa, the “Golden Spice” to Counteract Neuroinflammaging and Cognitive Decline—What Have We Learned and What Needs to Be Done. Nutrients 2021, 13 (5) , 1519. https://doi.org/10.3390/nu13051519
    47. Liangyu Xu, Xiaojiao Tang, Guozhe Zhang, Li Yang, Dan Yuan. Metabolic profile of curcumin self‐emulsifying drug delivery system in rats determined by ultra‐high performance liquid chromatography/quadrupole time‐of‐flight mass spectrometry. Biomedical Chromatography 2021, 35 (2) https://doi.org/10.1002/bmc.4988
    48. Małgorzata Makarewicz, Iwona Drożdż, Tomasz Tarko, Aleksandra Duda-Chodak. The Interactions between Polyphenols and Microorganisms, Especially Gut Microbiota. Antioxidants 2021, 10 (2) , 188. https://doi.org/10.3390/antiox10020188
    49. Adriana Trifan, Ana Clara Aprotosoaie, Anca Miron. Curcumin in Food. 2021, 1325-1368. https://doi.org/10.1007/978-981-15-4148-3_28
    50. Xuemei Liu, Bingyong Mao, Jiayu Gu, Jiaying Wu, Shumao Cui, Gang Wang, Jianxin Zhao, Hao Zhang, Wei Chen. Blautia —a new functional genus with potential probiotic properties?. Gut Microbes 2021, 13 (1) https://doi.org/10.1080/19490976.2021.1875796
    51. Tahiana Ramaholimihaso, Fayçal Bouazzaoui, Arthur Kaladjian. Curcumin in Depression: Potential Mechanisms of Action and Current Evidence—A Narrative Review. Frontiers in Psychiatry 2020, 11 https://doi.org/10.3389/fpsyt.2020.572533
    52. Gabriela L. Borosky, Kenneth K. Laali. Recent Advances in the Development of “Curcumin Inspired” Compounds as New Therapeutic Agents. Mini-Reviews in Medicinal Chemistry 2020, 20 (15) , 1543-1558. https://doi.org/10.2174/1389557520666200508083302
    53. Supawadee Burapan, Mihyang Kim, Yingyong Paisooksantivatana, Bekir Engin Eser, Jaehong Han. Thai Curcuma Species: Antioxidant and Bioactive Compounds. Foods 2020, 9 (9) , 1219. https://doi.org/10.3390/foods9091219
    54. Beatrice Scazzocchio, Luisa Minghetti, Massimo D’Archivio. Interaction between Gut Microbiota and Curcumin: A New Key of Understanding for the Health Effects of Curcumin. Nutrients 2020, 12 (9) , 2499. https://doi.org/10.3390/nu12092499
    55. Yujiao Zheng, Xiaowen Gou, Lili Zhang, Hanjia Gao, Yu Wei, Xiaotong Yu, Bing Pang, Jiaxing Tian, Xiaolin Tong, Min Li. Interactions Between Gut Microbiota, Host, and Herbal Medicines: A Review of New Insights Into the Pathogenesis and Treatment of Type 2 Diabetes. Frontiers in Cellular and Infection Microbiology 2020, 10 https://doi.org/10.3389/fcimb.2020.00360
    56. Feng Zhang, Fang He, Li Li, Lichun Guo, Bin Zhang, Shuhuai Yu, Wei Zhao. Bioavailability Based on the Gut Microbiota: a New Perspective. Microbiology and Molecular Biology Reviews 2020, 84 (2) https://doi.org/10.1128/MMBR.00072-19
    57. Wawaimuli Arozal, Melva Louisa, Vivian Soetikno. Selected Indonesian Medicinal Plants for the Management of Metabolic Syndrome: Molecular Basis and Recent Studies. Frontiers in Cardiovascular Medicine 2020, 7 https://doi.org/10.3389/fcvm.2020.00082
    58. Zhen-Zhen Sun, Xin-Yu Li, Sai Wang, Liang Shen, Hong-Fang Ji. Bidirectional interactions between curcumin and gut microbiota in transgenic mice with Alzheimer’s disease. Applied Microbiology and Biotechnology 2020, 104 (8) , 3507-3515. https://doi.org/10.1007/s00253-020-10461-x
    59. Yuh-Hwa Liu, Chia-Jung Lee, Liang-Chieh Chen, Tai-Lin Lee, Ying-Ying Hsieh, Chuan-Hsiao Han, Chang-Hang Yang, Wei-Jan Huang, Wen-Chi Hou. Acetylcholinesterase inhibitory activity and neuroprotection in vitro , molecular docking, and improved learning and memory functions of demethylcurcumin in scopolamine-induced amnesia ICR mice. Food & Function 2020, 11 (3) , 2328-2338. https://doi.org/10.1039/C9FO02339A
    60. Simon Vlad Luca, Irina Macovei, Alexandra Bujor, Anca Miron, Krystyna Skalicka-Woźniak, Ana Clara Aprotosoaie, Adriana Trifan. Bioactivity of dietary polyphenols: The role of metabolites. Critical Reviews in Food Science and Nutrition 2020, 60 (4) , 626-659. https://doi.org/10.1080/10408398.2018.1546669
    61. Ryszard Pluta, Sławomir Januszewski, Marzena Ułamek-Kozioł. Mutual Two-Way Interactions of Curcumin and Gut Microbiota. International Journal of Molecular Sciences 2020, 21 (3) , 1055. https://doi.org/10.3390/ijms21031055
    62. Letizia Bresciani, Claudia Favari, Luca Calani, Veronica Francinelli, Antonella Riva, Giovanna Petrangolini, Pietro Allegrini, Pedro Mena, Daniele Del Rio. The Effect of Formulation of Curcuminoids on Their Metabolism by Human Colonic Microbiota. Molecules 2020, 25 (4) , 940. https://doi.org/10.3390/molecules25040940
    63. Manoj K. Gupta, Ramakrishna Vadde, Vemula Sarojamma. Curcumin - A Novel Therapeutic Agent in the Prevention of Colorectal Cancer. Current Drug Metabolism 2020, 20 (12) , 977-987. https://doi.org/10.2174/1389200220666191007153238
    64. Clara Bik-San Lau, Grace Gar-Lee Yue. Adjuvant Value of Turmeric Extract (Containing Curcumin) in Colorectal Cancer Management. 2020, 209-239. https://doi.org/10.1007/978-3-030-39855-2_7
    65. Adriana Trifan, Ana Clara Aprotosoaie, Anca Miron. Curcumin in Food. 2020, 1-44. https://doi.org/10.1007/978-981-13-1745-3_28-1
    66. Erika Cione, Chiara La Torre, Roberto Cannataro, Maria Cristina Caroleo, Pierluigi Plastina, Luca Gallelli. Quercetin, Epigallocatechin Gallate, Curcumin, and Resveratrol: From Dietary Sources to Human MicroRNA Modulation. Molecules 2020, 25 (1) , 63. https://doi.org/10.3390/molecules25010063
    67. Timo A. Thumann, Eva-Maria Pferschy-Wenzig, Christine Moissl-Eichinger, Rudolf Bauer. The role of gut microbiota for the activity of medicinal plants traditionally used in the European Union for gastrointestinal disorders. Journal of Ethnopharmacology 2019, 245 , 112153. https://doi.org/10.1016/j.jep.2019.112153
    68. Yuh-Hwa Liu, Tai-Lin Lee, Chuan-Hsiao Han, Yi-Shan Lee, Wen-Chi Hou. Anti-glycation, anti-hemolysis, and ORAC activities of demethylcurcumin and tetrahydroxycurcumin in vitro and reductions of oxidative stress in d-galactose-induced BALB/c mice in vivo. Botanical Studies 2019, 60 (1) https://doi.org/10.1186/s40529-019-0258-x
    69. Liang Shen, Hong-Fang Ji. Bidirectional interactions between dietary curcumin and gut microbiota. Critical Reviews in Food Science and Nutrition 2019, 59 (18) , 2896-2902. https://doi.org/10.1080/10408398.2018.1478388
    70. Zonglin Liu, Xiaowen Sun, Xun Sun, Shuhui Wang, Ying Xu. Fucoxanthin Isolated from Undaria pinnatifida Can Interact with Escherichia coli and lactobacilli in the Intestine and Inhibit the Growth of Pathogenic Bacteria. Journal of Ocean University of China 2019, 18 (4) , 926-932. https://doi.org/10.1007/s11802-019-4019-y
    71. Toshio Niwa, Shin-ichiro Yokoyama, Mika Mochizuki, Toshihiko Osawa. Curcumin metabolism by human intestinal bacteria in vitro. Journal of Functional Foods 2019, 61 , 103463. https://doi.org/10.1016/j.jff.2019.103463
    72. Di Meo, Margarucci, Galderisi, Crispi, Peluso. Curcumin, Gut Microbiota, and Neuroprotection. Nutrients 2019, 11 (10) , 2426. https://doi.org/10.3390/nu11102426
    73. Michele Dei Cas, Riccardo Ghidoni. Dietary Curcumin: Correlation between Bioavailability and Health Potential. Nutrients 2019, 11 (9) , 2147. https://doi.org/10.3390/nu11092147
    74. Kenneth K. Laali, Angela T. Zwarycz, Scott D. Bunge, Gabriela L. Borosky, Manabu Nukaya, Gregory D. Kennedy. Deuterated Curcuminoids: Synthesis, Structures, Computational/Docking and Comparative Cell Viability Assays against Colorectal Cancer. ChemMedChem 2019, 14 (12) , 1173-1184. https://doi.org/10.1002/cmdc.201900179
    75. Shishan Fu, Said Ajlouni, Luz Sanguansri, Ken Ng, Mary Ann Augustin. In vitro degradation of curcuminoids by faecal bacteria: Influence of method of addition of curcuminoids into buttermilk yoghurt. Food Chemistry 2019, 283 , 414-421. https://doi.org/10.1016/j.foodchem.2018.12.124
    76. Beibei Zhang, Jing Yang, Zifei Qin, Shishi Li, Jinjin Xu, Zhihong Yao, Xiaojian Zhang, Frank J. Gonzalez, Xinsheng Yao, . Mechanism of the efflux transport of demethoxycurcumin-O-glucuronides in HeLa cells stably transfected with UDP-glucuronosyltransferase 1A1. PLOS ONE 2019, 14 (5) , e0217695. https://doi.org/10.1371/journal.pone.0217695
    77. Kathryn Burge, Aarthi Gunasekaran, Jeffrey Eckert, Hala Chaaban. Curcumin and Intestinal Inflammatory Diseases: Molecular Mechanisms of Protection. International Journal of Molecular Sciences 2019, 20 (8) , 1912. https://doi.org/10.3390/ijms20081912
    78. Jose Jaimes, Veronika Jarosova, Ondrej Vesely, Chahrazed Mekadim, Jakub Mrazek, Petr Marsik, Jiri Killer, Karel Smejkal, Pavel Kloucek, Jaroslav Havlik. Effect of Selected Stilbenoids on Human Fecal Microbiota. Molecules 2019, 24 (4) , 744. https://doi.org/10.3390/molecules24040744
    79. Wissam Zam. Gut Microbiota as a Prospective Therapeutic Target for Curcumin: A Review of Mutual Influence. Journal of Nutrition and Metabolism 2018, 2018 , 1-11. https://doi.org/10.1155/2018/1367984
    80. Yoona Kim, Peter Clifton. Curcumin, Cardiometabolic Health and Dementia. International Journal of Environmental Research and Public Health 2018, 15 (10) , 2093. https://doi.org/10.3390/ijerph15102093
    81. Xiao-Yu Xu, Xiao Meng, Sha Li, Ren-You Gan, Ya Li, Hua-Bin Li. Bioactivity, Health Benefits, and Related Molecular Mechanisms of Curcumin: Current Progress, Challenges, and Perspectives. Nutrients 2018, 10 (10) , 1553. https://doi.org/10.3390/nu10101553
    82. Siddhartha S. Ghosh, Hongliang He, Jing Wang, Todd W. Gehr, Shobha Ghosh. Curcumin-mediated regulation of intestinal barrier function: The mechanism underlying its beneficial effects. Tissue Barriers 2018, 6 (1) , e1425085. https://doi.org/10.1080/21688370.2018.1425085
    83. Ágnes Alberti, Eszter Riethmüller, Szabolcs Béni. Characterization of diarylheptanoids: An emerging class of bioactive natural products. Journal of Pharmaceutical and Biomedical Analysis 2018, 147 , 13-34. https://doi.org/10.1016/j.jpba.2017.08.051
    84. Lucrecia Carrera-Quintanar, Rocío I. López Roa, Saray Quintero-Fabián, Marina A. Sánchez-Sánchez, Barbara Vizmanos, Daniel Ortuño-Sahagún. Phytochemicals That Influence Gut Microbiota as Prophylactics and for the Treatment of Obesity and Inflammatory Diseases. Mediators of Inflammation 2018, 2018 , 1-18. https://doi.org/10.1155/2018/9734845
    85. Christine T. Peterson, Alexandra R. Vaughn, Vandana Sharma, Deepak Chopra, Paul J. Mills, Scott N. Peterson, Raja K. Sivamani. Effects of Turmeric and Curcumin Dietary Supplementation on Human Gut Microbiota: A Double-Blind, Randomized, Placebo-Controlled Pilot Study. Journal of Evidence-Based Integrative Medicine 2018, 23 , 2515690X1879072. https://doi.org/10.1177/2515690X18790725
    86. Zhaofeng Liang, Rui Wu, Wei Xie, Chunfeng Xie, Jieshu Wu, Shanshan Geng, Xiaoting Li, Mingming Zhu, Weiwei Zhu, Jianyun Zhu, Cong Huang, Xiao Ma, Wenrong Xu, Caiyun Zhong, Hongyu Han. Effects of Curcumin on Tobacco Smoke-induced Hepatic MAPK Pathway Activation and Epithelial-Mesenchymal Transition In Vivo. Phytotherapy Research 2017, 31 (8) , 1230-1239. https://doi.org/10.1002/ptr.5844
    87. Chun-Yan An, Zhen-Zhen Sun, Liang Shen, Hong-Fang Ji. Biotransformation of food spice curcumin by gut bacterium Bacillus megaterium DCMB-002 and its pharmacological implications. Food & Nutrition Research 2017, 61 (1) , 1412814. https://doi.org/10.1080/16546628.2017.1412814
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