Chinese Journal of Organic Chemistry >
Design, Synthesis and Bioactivity Evaluation of Guaiazulene Derivatives with Antioxidant and Anti-inflammatory Activities
Received date: 2022-04-11
Revised date: 2022-05-19
Online published: 2022-06-09
Supported by
National Natural Science Foundation of China(22075310); Science and Technology Commission of Shanghai Municipality(19XD1424700); Science and Technology Commission of Shanghai Municipality(20DZ2255200)
Animal and plant-derived guaiazulene (GA) has the characteristics of antimicrobial, antioxidant, anti-inflammatory, anti-allergic and low toxicity. Sodium guaiazulene sulfonate (GAS-Na), a water-soluble derivative of GA, also has the effects of anti-inflammatory, promoting epithelial cell growth and wound healing. However, the commercial active molecules GA and GAS-Na have poor stability to light and heat. Therefore, in order to explore the guaiazulene biomedical functional molecules with higher activity and stability, 2,2'-biguaiazulene (BGA) and (2,2'-biguaiazulene)-1,1'-disulfonic acid sodium (BGAS-Na) were synthesized. Compared with GA and GAS-Na, the antioxidant activities of BGA and BGAS-Na were evaluated, and their biological effects on NO release and cell viability of LPS-induced RAW 264.7 macrophages were studied. The results showed that BGA and BGAS-Na had better antioxidant capacity and improved stability compared with GA and GAS-Na; BGAS-Na had the best NO inhibition rate in the anti-inflammatory activity test (the IC50 value was 5.64 μg/ mL), which was better than that of the commercial molecule GAS-Na, and the inhibitory effect was dose-dependent. In addition, the four compounds did not affect the growth of macrophages and had low cytotoxicity. Therefore, BGAS-Na is expected to become a potential anti-inflammatory drug.
Lei Li , Congcong Zhu , Quangang Zhu , Zhongjian Chen , Xike Gao . Design, Synthesis and Bioactivity Evaluation of Guaiazulene Derivatives with Antioxidant and Anti-inflammatory Activities[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2906 -2913 . DOI: 10.6023/cjoc202204025
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