Total Synthesis and Anti-Inflammatory Bioactivity of (−)-Majusculoic Acid and Its Derivatives

Marine Drugs

卷:19

Zheng-Biao Zou¹  Bing Cai¹  Zhi-Hui He¹  Qing-Xiang Yan¹  Ting-Ting Chen¹  Qing-Qing Le¹  Xian-Wen Yang¹  Hong-Xiu Xiao²  Su-Lan Luo² 

[1] Key Laboratory of Marine Biogenetic Resources, Third Institute of Oceanography, Ministry of Natural Resources, 184 Daxue Road, Xiamen 361005, China;

[2] Key Laboratory of Tropical Biological Resources of Ministry of Education, Hainan University, Haikou 570228, China;

关键词: marine natural products;    (−)-majusculoic acid;    anti-inflammation;    LPS;    CCK-8;   

DOI  :  10.3390/md19060288

来源: DOAJ

【 摘 要 】

The first total synthesis of marine natural product, (−)-majusculoic acid (1) and its seven analogs (9–15), was accomplished in three to ten steps with a yield of 3% to 28%. The strategy featured the application of the conformational controlled establishment of the trans-cyclopropane and stereochemical controlled bromo-olefination or olefination by Horner–Wadsworth–Emmons (HWE) reaction. The potential anti-inflammatory activity of the eight compounds (1 and 9–15) was evaluated by determining the nitric oxide (NO) production in the lipopolysaccharide (LPS)-induced mouse macrophages RAW264.7. (−)-Majusculoic acid (1), methyl majusculoate (9), and (1R,2R)-2-((3E,5Z)-6-bromonona-3,5-dien-1-yl)cyclopropane-1-carboxylic acid (12) showed significant effect with inhibition rates of 33.68%, 35.75%, and 43.01%, respectively. Moreover, they did not show cytotoxicity against RAW264.7 cells, indicating that they might be potential anti-inflammatory agents.

【 授权许可】

Unknown