Literature DB >> 12057639

Cysteinyl-flavan-3-ol conjugates from grape procyanidins. Antioxidant and antiproliferative properties.

J L Torres1, C Lozano, L Julià, F J Sánchez-Baeza, J M Anglada, J J Centelles, M Cascante.   

Abstract

New bio-based antioxidant compounds have been obtained by depolymerisation of grape polymeric flavanols in the presence of cysteine. Their preparation and purification, as well as their antiradical/antioxidant and antiproliferative properties are reported. 4beta-(S-cysteinyl)epicatechin 5, 4beta-(S-cysteinyl)catechin 6 and 4beta-(S-cysteinyl)epicatechin 3-O-gallate 7 were efficiently purified from the crude depolymerised mixture by cation-exchange chromatography and preparative reversed-phase chromatography. The new compounds were more efficient than the underivatised (-)-epicatechin 1 as scavengers of the 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH) and weak growth inhibitors of human colon carcinoma HT29 cells. The order of antiradical and antiproliferative efficiency was 7 >5 approximately 6 >1, the same for both assays.

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Year:  2002        PMID: 12057639     DOI: 10.1016/s0968-0896(02)00127-x

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


  10 in total

1.  A novel approach to enhancing cellular glutathione levels.

Authors:  Pamela Maher; Jan Lewerenz; Carles Lozano; Josep Lluís Torres
Journal:  J Neurochem       Date:  2008-08-12       Impact factor: 5.372

2.  Targeting Trimeric and Tetrameric Proanthocyanidins of Cinnamomum verum Bark as Bioactives for Dental Therapies.

Authors:  Joo-Won Nam; Rasika S Phansalkar; David C Lankin; James B McAlpine; Ariene A Leme-Kraus; Ana K Bedran-Russo; Shao-Nong Chen; Guido F Pauli
Journal:  J Nat Prod       Date:  2020-11-05       Impact factor: 4.050

3.  Subtle Chemical Shifts Explain the NMR Fingerprints of Oligomeric Proanthocyanidins with High Dentin Biomodification Potency.

Authors:  Joo-Won Nam; Rasika S Phansalkar; David C Lankin; Jonathan Bisson; James B McAlpine; Ariene A Leme; Cristina M P Vidal; Benjamin Ramirez; Matthias Niemitz; Ana Bedran-Russo; Shao-Nong Chen; Guido F Pauli
Journal:  J Org Chem       Date:  2015-07-27       Impact factor: 4.354

4.  General aspects of colorectal cancer.

Authors:  Josep J Centelles
Journal:  ISRN Oncol       Date:  2012-11-14

Review 5.  Red Fruits: Extraction of Antioxidants, Phenolic Content, and Radical Scavenging Determination: A Review.

Authors:  Gádor-Indra Hidalgo; María Pilar Almajano
Journal:  Antioxidants (Basel)       Date:  2017-01-19

6.  Integrating Targeted and Untargeted Metabolomics to Investigate the Processing Chemistry of Polygoni Multiflori Radix.

Authors:  Li Liang; Jun Xu; Wen-Wen Zhou; Eric Brand; Hu-Biao Chen; Zhong-Zhen Zhao
Journal:  Front Pharmacol       Date:  2018-08-28       Impact factor: 5.810

7.  Enantioselctive syntheses of sulfur analogues of flavan-3-Ols.

Authors:  Pradeep K Sharma; Min He; Jurjus Jurayj; Da-Ming Gou; Richard Lombardy; Leo J Romanczyk; Hagen Schroeter
Journal:  Molecules       Date:  2010-08-13       Impact factor: 4.411

8.  Metabolite annotations based on the integration of mass spectral information.

Authors:  Yoko Iijima; Yukiko Nakamura; Yoshiyuki Ogata; Ken'ichi Tanaka; Nozomu Sakurai; Kunihiro Suda; Tatsuya Suzuki; Hideyuki Suzuki; Koei Okazaki; Masahiko Kitayama; Shigehiko Kanaya; Koh Aoki; Daisuke Shibata
Journal:  Plant J       Date:  2008-02-07       Impact factor: 6.417

9.  Antioxidant activity and proanthocyanidin profile of Selliguea feei rhizomes.

Authors:  Caili Fu; Hongyu Wang; Wei Ling Ng; Lixia Song; Dejian Huang
Journal:  Molecules       Date:  2013-04-11       Impact factor: 4.411

Review 10.  Role of Sulphur and Heavier Chalcogens on the Antioxidant Power and Bioactivity of Natural Phenolic Compounds.

Authors:  Maria Laura Alfieri; Lucia Panzella; Riccardo Amorati; Alice Cariola; Luca Valgimigli; Alessandra Napolitano
Journal:  Biomolecules       Date:  2022-01-06
  10 in total

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