Structure-Activity Relationship of Curcumin: Role of the Methoxy Group in Anti-inflammatory and Anticolitis Effects of Curcumin

Journal of Agricultural and Food Chemistry
Haixia YangGuodong Zhang

Abstract

Curcumin, a dietary compound from turmeric, has beneficial effects on inflammatory diseases such as inflammatory bowel disease. Most previous studies have focused on the structure-activity relationship of the thiol-reactive α,β-unsaturated carbonyl groups of curcumin, so little is known about the roles of methoxy groups in biological activities of curcumin. Here we synthesized a series of curcumin analogues with different substitution groups (R = H-, Br-, Cl-, F-, NO2-, CH3-, and OH-) to replace the methoxy group and evaluated their biological effects in vitro and in vivo. Curcumin, Cur-OH, and Cur-Br (25 μM) suppressed 74.91 ± 0.88, 77.75 ± 0.89, and 71.75 ± 0.90% of LPS-induced NO production, respectively (P < 0.05). Similarly, these compounds also decreased iNOS expression, COX-2 expression, and NF-κB signaling in RAW 264.7 macrophage cells (P < 0.05). However, other analogues, especially Cur-NO2, were inactive (P > 0.05). In the dextran sulfate sodium (DSS)-induced colitis mouse model, the Cur-Br analogue also showed a beneficial effect the same as curcumin (P < 0.05), whereas the Cur-NO2 analogue had no effect in the animal model (P > 0.05). Together, the analogues have dramatically different effects on inflammation, suppo...Continue Reading

References

Feb 17, 1998·Chemico-biological Interactions·M L van IerselP J van Bladeren
Nov 15, 2006·Clinical Gastroenterology and Hepatology : the Official Clinical Practice Journal of the American Gastroenterological Association·Hiroyuki HanaiYukio Koide
Feb 6, 2007·International Immunopharmacology·Laura Camacho-BarqueroCatalina Alarcón de la Lastra
Apr 13, 2007·Digestive Diseases and Sciences·Yasuyuki DeguchiYoshihide Fujiyama
Nov 15, 2007·Molecular Pharmaceutics·Preetha AnandBharat B Aggarwal
Mar 3, 2009·Bioorganic & Medicinal Chemistry Letters·James R FuchsPui-Kai Li
Mar 17, 2009·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Hossam M M ArafaFarid M A Hamada
Jan 22, 2010·Journal of Agricultural and Food Chemistry·Guodong ZhangKirk L Parkin
Jun 1, 2013·Journal of Cancer Prevention·Joon-Yeop YangYoung-Joon Surh
May 13, 2015·Genetics and Molecular Research : GMR·C-P LiL Shi
Sep 2, 2015·Nature Reviews. Gastroenterology & Hepatology·Gilaad G Kaplan
Nov 27, 2015·Molecular Nutrition & Food Research·Yoshiki NimiyaGuodong Zhang
Mar 30, 2016·Colloids and Surfaces. B, Biointerfaces·Ana BeloquiVéronique Préat

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Citations

Feb 1, 2019·Pest Management Science·Ja Yeong JangJin-Cheol Kim
Nov 28, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fang-Pin ChangYueh-Hsiung Kuo
Apr 30, 2020·Mini Reviews in Medicinal Chemistry·Ayushi SethiyaShikha Agarwal
Nov 11, 2020·Fundamental & Clinical Pharmacology·Larissa Córdova TuronesElson Alves Costa
Sep 4, 2019·European Journal of Medicinal Chemistry·Sawsan A NoureddinKhalid O Al-Footy
Jan 27, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luis David Arango-De la PavaGabriela Trejo-Tapia
Sep 23, 2019·Journal of Colloid and Interface Science·Mahesh Kharat, David Julian McClements
Jun 23, 2019·European Journal of Pharmacology·Kanyasiri RakariyathamHang Xiao
Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Paola Borrego-MuñozDiego Quiroga

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