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

by 1,2, Sha Li 1,3,*, 2,3, 2,3, 2,3 and 2,3
1
Department of Pharmaceutics, Jinan University College of Pharmacy, Guangzhou 510632, China
2
Institute of New Drug Research, Jinan University College of Pharmacy, Guangzhou 510632, China
3
Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM, Jinan University College of Pharmacy, Guangzhou 510632, China
*
Author to whom correspondence should be addressed.
Molecules 2012, 17(1), 728-739; https://doi.org/10.3390/molecules17010728
Received: 10 October 2011 / Revised: 4 January 2012 / Accepted: 12 January 2012 / Published: 12 January 2012
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. View Full-Text
Keywords: andrographolide; andrographolide analogues; glutathione; NF-κB; medicinal chemistry andrographolide; andrographolide analogues; glutathione; NF-κB; medicinal chemistry
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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.

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