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Mechanism of the Superoxide Scavenging Activity of Neoandrographolide − A Natural Product from Andrographis paniculata Nees

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Department of Food Science, Rutgers University, 65 Dudley Road, New Brunswick, New Jersey, 08901-8520
Cite this: J. Agric. Food Chem. 2002, 50, 16, 4662–4665
Publication Date (Web):June 26, 2002
https://doi.org/10.1021/jf025556f
Copyright © 2002 American Chemical Society
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    Abstract

    It was hypothesized that neoandrographolide might scavenge free radicals by donating the allylic hydrogen of the unsaturated lactone ring. It was found that the stoichiometry of the reaction between neoandrographolide and superoxide radical generated from KO2 in DMSO was 2 to 1. One major reaction product was isolated and determined to be a diacid formed by the opening of the lactone ring. It was concluded that the antiradical activity of neoandrographolide proceeded by hydrogen abstraction from carbon C-15. A reaction mechanism was proposed.

    Keywords: Andrographis paniculata; neoandrographolide; superoxide radical; antiradical activity; diterpene lactone

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     Corresponding author. Tel:  732-932-9611 ext. 235. Fax:  732-932-6776. E-mail:  [email protected].

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    27. Yixiong Wang, Lixia Chen, Feng Zhao, Zhihui Liu, Jianqiang Li, Feng Qiu. Microbial transformation of neoandrographolide by Mucor spinosus (AS 3.2450). Journal of Molecular Catalysis B: Enzymatic 2011, 68 (1) , 83-88. https://doi.org/10.1016/j.molcatb.2010.09.016
    28. Karami. Effects of Dietary Herbal Antioxidants Supplemented on Feedlot Growth Performance and Carcass Composition of Male Goats. American Journal of Animal and Veterinary Sciences 2010, 5 (1) , 33-39. https://doi.org/10.3844/ajavsp.2010.33.39
    29. Subhasis Das, Sreeparna Neogy, N. Gautam, Somenath Roy. In vitro nicotine induced superoxide mediated DNA fragmentation in lymphocytes: Protective role of Andrographis paniculata Nees. Toxicology in Vitro 2009, 23 (1) , 90-98. https://doi.org/10.1016/j.tiv.2008.10.012
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    31. Zhiqiang Zhang, Gallant Kar-Lun Chan, Jieliang Li, Wang-Fun Fong, Hon-Yeung Cheung. Molecular Interaction between Andrographolide and Glutathione Follows Second Order Kinetics. Chemical and Pharmaceutical Bulletin 2008, 56 (9) , 1229-1233. https://doi.org/10.1248/cpb.56.1229
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