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Molecules 2012, 17(1), 728-739; doi:10.3390/molecules17010728
Article

Reaction Characteristics of Andrographolide and its Analogue AL-1 with GSH, as a Simple Chemical Simulation of NF-κB Inhibition

1,2, 1,3,* , 2,3, 2,3, 2,3 and 2,3
Received: 10 October 2011; in revised form: 4 January 2012 / Accepted: 12 January 2012 / Published: 12 January 2012
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Abstract: 14-α-Lipoic acid-3,19-dihydroxyandrographolide (AL-1, 2) is an analogue of andrographolide (Andro, 1) coupled to α-lipoic acid (LA, 4). AL-1 was at least 10-fold more potent than the natural parent compound Andro in inhibiting nuclear factor (NF)-κB activation in RIN-m cells. In the present study, glutathione (GSH, 3) was used as a simple chemical model molecule of NF-κB with cysteine 62. The characteristics of the reaction between AL-1 or Andro and GSH were investigated to trace some possible elucidation for the inhibitive mechanism and stronger inhibition of AL-1 to NF-κB activation. The results showed that the main reaction products of AL-1 and Andro were identical, sulfhydryl adduct and amino adduct. AL-1 reacted much faster than Andro with GSH. The product yield of AL-1 was much higher than that of Andro. It was speculated that AL-1 might inhibit NF-κB by the same mechanism as Andro. And the faster reaction rate and higher yield may account for the stronger NF-κB inhibition of AL-1 when compared with Andro.
Keywords: andrographolide; andrographolide analogues; glutathione; NF-κB; medicinal chemistry andrographolide; andrographolide analogues; glutathione; NF-κB; medicinal chemistry
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yao, H.; Li, S.; Yu, P.; Tang, X.; Jiang, J.; Wang, Y. Reaction Characteristics of Andrographolide and its Analogue AL-1 with GSH, as a Simple Chemical Simulation of NF-κB Inhibition. Molecules 2012, 17, 728-739.

AMA Style

Yao H, Li S, Yu P, Tang X, Jiang J, Wang Y. Reaction Characteristics of Andrographolide and its Analogue AL-1 with GSH, as a Simple Chemical Simulation of NF-κB Inhibition. Molecules. 2012; 17(1):728-739.

Chicago/Turabian Style

Yao, Hui; Li, Sha; Yu, Pei; Tang, Xiaodan; Jiang, Jie; Wang, Yuqiang. 2012. "Reaction Characteristics of Andrographolide and its Analogue AL-1 with GSH, as a Simple Chemical Simulation of NF-κB Inhibition." Molecules 17, no. 1: 728-739.


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