Literature DB >> 24280069

Curcumin glucuronides: assessing the proliferative activity against human cell lines.

Ashutosh Pal1, Bokyung Sung1, Basvoju A Bhanu Prasad1, Paul T Schuber1, Sahdeo Prasad1, Bharat B Aggarwal1, William G Bornmann2.   

Abstract

A gram scale synthesis of the glucuronide metabolites of curcumin were completed in four steps. The newly synthesized curcumin glucuronide compounds 2 and 3 along with curcumin 1 were tested and their anti-proliferative effects against KBM-5, Jurkat cell, U266, and A549 cell lines were reported. Biological data revealed that as much as 1 μM curcumin 1 exhibited anticancer activity and almost 100% cell kill was noted at 10 μM on two out of four cell lines; while curcumin mono-glucuronide 2 as well as di-glucuronide 3 displayed no suppression of cell proliferation.
Copyright © 2013. Published by Elsevier Ltd.

Entities:  

Keywords:  Curcumin; Curcumin di-glucuronides; Curcumin mono-glucuronide; ISDDQQPRTHCEGT-XANUIUACSA-N; JCAFLHUESYYNFH-NMQQATKUSA-N; ZIUSSTSXXLLKKK-KOBPDPAPSA-N

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Year:  2013        PMID： 24280069      PMCID： PMC4128398          DOI： 10.1016/j.bmc.2013.11.006

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  24 in total

1.  Synthesis of (+/-)-cassumunins A and B, new curcuminoid antioxidants having protective activity of the living cell against oxidative damage.

Authors:  T Masuda; H Matsumura; Y Oyama; Y Takeda; A Jitoe; A Kida; K Hidaka
Journal:  J Nat Prod       Date:  1998-05       Impact factor: 4.050

2.  Synthesis of guaiacol-alpha-D: -glucoside and curcumin-bis-alpha-D: -glucoside by an amyloglucosidase from Rhizopus.

Authors:  Giriyapura R Vijayakumar; Soundar Divakar
Journal:  Biotechnol Lett       Date:  2005-09       Impact factor: 2.461

3.  Activation of NFkappaB is inhibited by curcumin and related enones.

Authors:  Waylon M Weber; Lucy A Hunsaker; C Nathaniel Roybal; Ekaterina V Bobrovnikova-Marjon; Steve F Abcouwer; Robert E Royer; Lorraine M Deck; David L Vander Jagt
Journal:  Bioorg Med Chem       Date:  2005-12-07       Impact factor: 3.641

4.  Curcumin inhibits the proliferation and cell cycle progression of human umbilical vein endothelial cell.

Authors:  A K Singh; G S Sidhu; T Deepa; R K Maheshwari
Journal:  Cancer Lett       Date:  1996-10-01       Impact factor: 8.679

5.  Design, development and synthesis of mixed bioconjugates of piperic acid-glycine, curcumin-glycine/alanine and curcumin-glycine-piperic acid and their antibacterial and antifungal properties.

Authors:  Satyendra Mishra; Upma Narain; Roli Mishra; Krishna Misra
Journal:  Bioorg Med Chem       Date:  2005-03-01       Impact factor: 3.641

Review 6.  Bioavailability of curcumin: problems and promises.

Authors:  Preetha Anand; Ajaikumar B Kunnumakkara; Robert A Newman; Bharat B Aggarwal
Journal:  Mol Pharm       Date:  2007-11-14       Impact factor: 4.939

7.  Ultrasound-assisted reaction of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide with potassium salt of curcumin under PTC conditions.

Authors:  Kattera S Parvathy; Pullabhatla Srinivas
Journal:  Ultrason Sonochem       Date:  2007-11-05       Impact factor: 7.491

8.  Chemopreventive effect of curcumin, a naturally occurring anti-inflammatory agent, during the promotion/progression stages of colon cancer.

Authors:  T Kawamori; R Lubet; V E Steele; G J Kelloff; R B Kaskey; C V Rao; B S Reddy
Journal:  Cancer Res       Date:  1999-02-01       Impact factor: 12.701

9.  Inhibitory effects of curcumin on tumor initiation by benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene.

Authors:  M T Huang; Z Y Wang; C A Georgiadis; J D Laskin; A H Conney
Journal:  Carcinogenesis       Date:  1992-11       Impact factor: 4.944

10.  Curcumin induces a p53-dependent apoptosis in human basal cell carcinoma cells.

Authors:  S H Jee; S C Shen; C R Tseng; H C Chiu; M L Kuo
Journal:  J Invest Dermatol       Date:  1998-10       Impact factor: 8.551
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  18 in total

1.  Curcumin, but not curcumin-glucuronide, inhibits Smad signaling in TGFβ-dependent bone metastatic breast cancer cells and is enriched in bone compared to other tissues.

Authors:  Andrew G Kunihiro; Julia A Brickey; Jennifer B Frye; Paula B Luis; Claus Schneider; Janet L Funk
Journal:  J Nutr Biochem       Date:  2018-10-11       Impact factor: 6.048

2.  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

Review 3.  Regulation of Gene Expression through Food-Curcumin as a Sirtuin Activity Modulator.

Authors:  Anca Ungurianu; Anca Zanfirescu; Denisa Margină
Journal:  Plants (Basel)       Date:  2022-06-30

4.  Curcumin induces secretion of glucagon-like peptide-1 through an oxidation-dependent mechanism.

Authors:  Abdul-Musawwir Alli-Oluwafuyi; Paula B Luis; Fumie Nakashima; Juan A Giménez-Bastida; Sai Han Presley; Matthew T Duvernay; Ezekiel O Iwalewa; Claus Schneider
Journal:  Biochimie       Date:  2019-08-27       Impact factor: 4.079

5.  Intra-Articular Injections of Curcumin Monoglucuronide TBP1901 Suppresses Articular Cartilage Damage and Regulates Subchondral Bone Alteration in an Osteoarthritis Rat Model.

Authors:  Akihiro Nakahata; Akira Ito; Ryo Nakahara; Atsuhiro Kishimoto; Atsushi Imaizumi; Tadashi Hashimoto; Shogo Mukai; Yasuaki Nakagawa; Hiroshi Kuroki
Journal:  Cartilage       Date:  2021-09-03       Impact factor: 3.117

6.  Chemopreventive efficacy of oral curcumin: a prodrug hypothesis.

Authors:  Garvey Liu; Vidhi Khanna; Ameya Kirtane; Alex Grill; Jayanth Panyam
Journal:  FASEB J       Date:  2019-05-28       Impact factor: 5.834

7.  Synthesis and Evaluation of the Anti-Oxidant Capacity of Curcumin Glucuronides, the Major Curcumin Metabolites.

Authors:  Ambar K Choudhury; Suganya Raja; Sanjata Mahapatra; Kalyanam Nagabhushanam; Muhammed Majeed
Journal:  Antioxidants (Basel)       Date:  2015-12-02

8.  Pharmacokinetics of a Single Dose of Turmeric Curcuminoids Depends on Formulation: Results of a Human Crossover Study.

Authors:  Pascale Fança-Berthon; Mathieu Tenon; Sabrina Le Bouter-Banon; Alexis Manfré; Corinne Maudet; Angelina Dion; Hélène Chevallier; Julie Laval; Richard B van Breemen
Journal:  J Nutr       Date:  2021-07-01       Impact factor: 4.798

Review 9.  Recent developments in delivery, bioavailability, absorption and metabolism of curcumin: the golden pigment from golden spice.

Authors:  Sahdeo Prasad; Amit K Tyagi; Bharat B Aggarwal
Journal:  Cancer Res Treat       Date:  2014-01-15       Impact factor: 4.679

Review 10.  Curcumin-A Viable Agent for Better Bladder Cancer Treatment.

Authors:  Jochen Rutz; Andrea Janicova; Katja Woidacki; Felix K-H Chun; Roman A Blaheta; Borna Relja
Journal:  Int J Mol Sci       Date:  2020-05-26       Impact factor: 5.923
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