Optimized One-Step Preparation of a Bioactive Natural Product,Guaiazulene-2,9-dione  

作　　者：CHENG Canling LI Pinglin WANG Wei SHI Xuefeng ZHANG Gang ZHU Hongyan WU Rongcui TANG Xuli LI Guoqiang 

机构地区：[1]Key Laboratory of Marine Drugs of Chinese Ministry of Education,School of Medicine and Pharmacy,Ocean University of China [2]TCM and Ethnomedicine Innovation & Development Laboratory,School of Pharmacy,Hunan University of Chinese Medicine [3]College of Chemistry and Chemical Engineering,Ocean University of China

出　　处：《Journal of Ocean University of China》2014年第6期1000-1004,共5页中国海洋大学学报（英文版）

基　　金：supported by National Natural Science Foundation of China (No. 21102136);Changjiang Scholars and Innovative Research Team in University (PCSIRT,No. IRT0944)

摘　　要：We previously isolated a natural product, namely guaiazulene-2,9-dione showing strong antibacterial activity against Vibrio anguillarum, from a gorgonian Muriceides collaris collected in South China Sea. In this experiment, guaiazulene-2,9-dione was quantitatively synthesized with an optimized one-step bromine oxidation method using guaiazulene as the raw material. The key reaction condition including reaction time and temperature, drop rate of bromine, concentration of aqueous THF solution, respective molar ratio of guaiazulene to bromine and acetic acid, and concentration of guaiazulene in aqueous THF solution, were investigated individually at five levels each for optimization. Combined with the verification test to show the absolute yield of each optimization step, the final optimal condition was determined as: when a solution of 0.025 mmol m L-1 guaiazulene in 80% aqueous THF was treated with four volumes of bromine at a drop rate of 0.1 m L min-1 and four volumes of acetic acid at-5℃ for three hours, the yield of guaiazulene-2,9-dione was 23.72%. This was the first report concerning optimized one-step synthesis to provide a convenient method for the large preparation of guaiazulene-2,9-dione.We previously isolated a natural product, namely guaiazulene-2,9-dione showing strong antibacterial activity against Vibrio anguillarum, from a gorgonian Muriceides collaris collected in South China Sea. In this experiment, guaiazulene-2,9-dione was quantitatively synthesized with an optimized one-step bromine oxidation method using guaiazulene as the raw material. The key reaction condition including reaction time and temperature, drop rate of bromine, concentration of aqueous THF solution, respective molar ratio of guaiazulene to bromine and acetic acid, and concentration of guaiazulene in aqueous THF solution, were investigated individually at five levels each for optimization. Combined with the verification test to show the absolute yield of each optimization step, the final optimal condition was determined as： when a solution of 0.025mmol mL-1 guaiazulene in 80% aqueous THF was treated with four volumes of bromine at a drop rate of 0.1 mL min 1 and four volumes of acetic acid at -5℃ for three hours, the yield of guaiazulene-2,9-dione was 23.72%. This was the first report concerning optimized one-step synthesis to provide a convenient method for the large preparation of guaiazulene-2,9-dione.

关 键 词：azulene derivative  guaiazulene-2 9-dione  optimization  preparation 

分 类 号：Q936[生物学—微生物学]