Literature DB >> 25817068

Degradation of Curcumin: From Mechanism to Biological Implications.

Claus Schneider1, Odaine N Gordon1, Rebecca L Edwards1, Paula B Luis1.   

Abstract

Curcumin is the main bioactive ingredient in turmeric extract and widely consumed as part of the spice mix curry or as a dietary supplement. Turmeric has a long history of therapeutic application in traditional Asian medicine. Biomedical studies conducted in the past two decades have identified a large number of cellular targets and effects of curcumin. In vitro curcumin rapidly degrades in an autoxidative transformation to diverse chemical species, the formation of which has only recently been appreciated. This paper discusses how the degradation and metabolism of curcumin, through products and their mechanism of formation, provide a basis for the interpretation of preclinical data and clinical studies. It is suggested that the previously unrecognized diversity of its degradation products could be an important factor in explaining the polypharmacology of curcumin.

Entities:  

Keywords:  Michael reaction; bioactivity; curcuminoids; metabolism; polyphenol; protein adduction; quinone methide; turmeric

Mesh:

Substances:

Year:  2015        PMID: 25817068      PMCID: PMC4752206          DOI: 10.1021/acs.jafc.5b00244

Source DB:  PubMed          Journal:  J Agric Food Chem        ISSN: 0021-8561            Impact factor:   5.279


  62 in total

1.  Autoxidative and cyclooxygenase-2 catalyzed transformation of the dietary chemopreventive agent curcumin.

Authors:  Markus Griesser; Valentina Pistis; Takashi Suzuki; Noemi Tejera; Derek A Pratt; Claus Schneider
Journal:  J Biol Chem       Date:  2010-11-11       Impact factor: 5.157

2.  Binding and stabilization of transthyretin by curcumin.

Authors:  Raghu Pullakhandam; P N B S Srinivas; Madhavan K Nair; G Bhanuprakash Reddy
Journal:  Arch Biochem Biophys       Date:  2009-03-05       Impact factor: 4.013

3.  Chemical studies on antioxidant mechanism of curcumin: analysis of oxidative coupling products from curcumin and linoleate.

Authors:  T Masuda; T Maekawa; K Hidaka; H Bando; Y Takeda; H Yamaguchi
Journal:  J Agric Food Chem       Date:  2001-05       Impact factor: 5.279

4.  Curcumin inhibits growth of Saccharomyces cerevisiae through iron chelation.

Authors:  Steven Minear; Allyson F O'Donnell; Anna Ballew; Guri Giaever; Corey Nislow; Tim Stearns; Martha S Cyert
Journal:  Eukaryot Cell       Date:  2011-09-09

5.  Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism.

Authors:  Azam Hassaninasab; Yoshiteru Hashimoto; Kaori Tomita-Yokotani; Michihiko Kobayashi
Journal:  Proc Natl Acad Sci U S A       Date:  2011-04-05       Impact factor: 11.205

6.  Curcumin, a cancer chemopreventive and chemotherapeutic agent, is a biologically active iron chelator.

Authors:  Yan Jiao; John Wilkinson; Xiumin Di; Wei Wang; Heather Hatcher; Nancy D Kock; Ralph D'Agostino; Mary Ann Knovich; Frank M Torti; Suzy V Torti
Journal:  Blood       Date:  2008-09-24       Impact factor: 22.113

7.  Curcumin attenuates cytochrome P450 induction in response to 2,3,7,8-tetrachlorodibenzo-p-dioxin by ROS-dependently degrading AhR and ARNT.

Authors:  Hyunsung Choi; Yang-Sook Chun; Yong Jae Shin; Sang Kyu Ye; Myung-Suk Kim; Jong-Wan Park
Journal:  Cancer Sci       Date:  2008-11-17       Impact factor: 6.716

8.  Synthesis and evaluation of electron-rich curcumin analogues.

Authors:  Michael W Amolins; Laura B Peterson; Brian S J Blagg
Journal:  Bioorg Med Chem       Date:  2008-10-29       Impact factor: 3.641

Review 9.  Biological activities of curcumin and its analogues (Congeners) made by man and Mother Nature.

Authors:  Preetha Anand; Sherin G Thomas; Ajaikumar B Kunnumakkara; Chitra Sundaram; Kuzhuvelil B Harikumar; Bokyung Sung; Sheeja T Tharakan; Krishna Misra; Indira K Priyadarsini; Kallikat N Rajasekharan; Bharat B Aggarwal
Journal:  Biochem Pharmacol       Date:  2008-08-19       Impact factor: 5.858

Review 10.  Curcumin--from molecule to biological function.

Authors:  Tuba Esatbeyoglu; Patricia Huebbe; Insa M A Ernst; Dawn Chin; Anika E Wagner; Gerald Rimbach
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-04       Impact factor: 15.336

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  59 in total

1.  The Ecstasy and Agony of Assay Interference Compounds.

Authors:  Courtney Aldrich; Carolyn Bertozzi; Gunda I Georg; Laura Kiessling; Craig Lindsley; Dennis Liotta; Kenneth M Merz; Alanna Schepartz; Shaomeng Wang
Journal:  ACS Med Chem Lett       Date:  2017-02-28       Impact factor: 4.345

2.  A Curcumin Degradation Product, 7-Norcyclopentadione, Formed by Aryl Migration and Loss of a Carbon from the Heptadienedione Chain.

Authors:  Akil I Joseph; Paula B Luis; Claus Schneider
Journal:  J Nat Prod       Date:  2018-12-18       Impact factor: 4.050

Review 3.  Discovering proteasomal deubiquitinating enzyme inhibitors for cancer therapy: lessons from rational design, nature and old drug reposition.

Authors:  Kush Patel; Zainab So Ahmed; Xuemei Huang; Qianqian Yang; Elmira Ekinci; Christine M Neslund-Dudas; Bharati Mitra; Fawzy Aem Elnady; Young-Hoon Ahn; Huanjie Yang; Jinbao Liu; Qing Ping Dou
Journal:  Future Med Chem       Date:  2018-08-01       Impact factor: 3.808

4.  Stability studies of pure and mixture form of curcuminoids by reverse phase-HPLC method under various experimental stress conditions.

Authors:  Malleswara R Peram; Sunil S Jalalpure; Mahesh B Palkar; Prakash V Diwan
Journal:  Food Sci Biotechnol       Date:  2017-06-19       Impact factor: 2.391

Review 5.  Culinary Spice Plants in Dietary Supplement Products and Tested in Clinical Trials.

Authors:  Leila G Saldanha; Johanna T Dwyer; Joseph M Betz
Journal:  Adv Nutr       Date:  2016-03-15       Impact factor: 8.701

6.  Oxidative metabolism of curcumin-glucuronide by peroxidases and isolated human leukocytes.

Authors:  Paula B Luis; Odaine N Gordon; Fumie Nakashima; Akil I Joseph; Takahiro Shibata; Koji Uchida; Claus Schneider
Journal:  Biochem Pharmacol       Date:  2017-03-06       Impact factor: 5.858

7.  Selective Depletion and Enrichment of Constituents in "Curcumin" and Other Curcuma longa Preparations.

Authors:  J Brent Friesen; Yang Liu; Shao-Nong Chen; James B McAlpine; Guido F Pauli
Journal:  J Nat Prod       Date:  2019-03-08       Impact factor: 4.050

8.  The anti-inflammatory activity of curcumin is mediated by its oxidative metabolites.

Authors:  Rebecca L Edwards; Paula B Luis; Paolo V Varuzza; Akil I Joseph; Sai Han Presley; Rupesh Chaturvedi; Claus Schneider
Journal:  J Biol Chem       Date:  2017-11-02       Impact factor: 5.157

9.  Stability and anti-inflammatory activity of the reduction-resistant curcumin analog, 2,6-dimethyl-curcumin.

Authors:  Akil I Joseph; Rebecca L Edwards; Paula B Luis; Sai Han Presley; Ned A Porter; Claus Schneider
Journal:  Org Biomol Chem       Date:  2018-05-02       Impact factor: 3.876

Review 10.  Molecular targets of curcumin for cancer therapy: an updated review.

Authors:  Pandima Devi Kasi; Rajavel Tamilselvam; Krystyna Skalicka-Woźniak; Seyed Fazel Nabavi; Maria Daglia; Anupam Bishayee; Hamidreza Pazoki-Toroudi; Seyed Mohammad Nabavi
Journal:  Tumour Biol       Date:  2016-07-28
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