Journal article
Probing antioxidant activity of 2′-hydroxychalcones: Crystal and molecular structures, in vitro antiproliferative studies and in vivo effects on glucose regulation
Biochimie, Vol.95(10), pp.1954-1963
10/2013
Handle:
https://hdl.handle.net/2376/108489
PMID: 23851195
Abstract
In order to better understand the antioxidant behavior of a series of polyphenolic 2′-hydroxychalcones, we describe the results of several chemical and biological studies, in vitro and in vivo. Single crystal X-ray methods elucidated their molecular structures and important intermolecular interactions such as H-bonding and molecular stacking in the crystal structures that contribute to our knowledge in explaining antioxidant activity. The results of experiments using the 1,1-diphenyl-2-dipicrylhydrazyl (DPPH) UV–vis spectroscopic method indicate that a hydroxyl group in position 5′ induces the highest antioxidant activity. Consequently, 2,2′,5′-trihydroxychalcone was selected for further study in vitro towards ROS scavenging in L-6 myoblasts and THP-1 human monocytes, where it shows an excellent antioxidant activity in a concentration range lower than that reported by most studies of related molecules. In addition, this chalcone shows a very selective activity: it inhibits the proliferation of leukemic cells, but it does not affect the normal L-6 myoblasts and human fibroblasts. In studying 2,2′,5′-trihydroxychalcone's effect on weight gain and serum glucose and insulin levels in Zucker fatty (fa−/fa−) rats we found that supplementing the diet with a 10 mg/kg dose of this chalcone (3 times weekly) blunted the increase in glucose that co-occurs with weight gain over the 6-week treatment period. It is concluded that 2,2′,5′-trihydroxychalcone has the potential to serve as a protective agent for some debilitating diseases.
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- Title
- Probing antioxidant activity of 2′-hydroxychalcones: Crystal and molecular structures, in vitro antiproliferative studies and in vivo effects on glucose regulation
- Creators
- Miriam Rossi - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USAFrancesco Caruso - Istituto di Chimica Biomolecolare, Consiglio Nazionale delle Ricerche (CNR), c/o University of Rome “La Sapienza”, Istituto Chimico, Piazzale Aldo Moro 5, 00185 Rome, ItalyErica J Crespi - School of Biological Sciences, Washington State University, Pullman, WA 99164-4236, USAJens Z Pedersen - Department of Biology, University of Rome Tor Vergata, Via della Ricerca Scientifica 1, 00133 Roma, ItalyGail Nakano - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USAMichelle Duong - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USACelia Mckee - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USASharon Lee - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USAManasi Jiwrajka - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USACharles Caldwell - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USAFrancis Baffour - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USADylan Alex Karlin - Bard College, Department of Biology, Annandale-on-Hudson, NY, USAGenevieve Lidoff - Vassar College, Department of Chemistry, Box 484, Poughkeepsie, NY 12604-0484, USAStefano Leone - Department of Sciences, University Roma Tre, Viale G. Marconi, 446, 00146 Rome, ItalyValentina Balducci - Department of Sciences, University Roma Tre, Viale G. Marconi, 446, 00146 Rome, ItalyJaroslav Miler - Department of Biochemical Sciences, Faculty of Pharmacy in Hradec Králové, Charles University of Prague, Czech RepublicSandra Incerpi - Department of Sciences, University Roma Tre, Viale G. Marconi, 446, 00146 Rome, Italy
- Publication Details
- Biochimie, Vol.95(10), pp.1954-1963
- Academic Unit
- Biological Sciences, School of
- Publisher
- Elsevier B.V
- Identifiers
- 99900547475901842
- Language
- English
- Resource Type
- Journal article