Antifungal quinazolinones from marine-derived Bacillus cereus and their preparation |
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Authors: | Xu Zhihong Zhang Yapeng Fu Haichao Zhong Huimin Hong Kui Zhu Weiming |
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Institution: | a Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People’s Republic of China b College of Pharmacy, Wuhan University, Wuhan 430071, People’s Republic of China c College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People’s Republic of China |
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Abstract: | Two new quinazolinones alkaloids, R(+)-2-(heptan-3-yl)quinazolin-4(3H)-one (1) and (2R,3′R)+(2S,3′R)-2-(heptan-3-yl)-2,3-dihydroquinazolin-4(1H)-one (2) (a pair of epimers), as well as seven known analogues, 2-methylquinazolin-4(3H)-one (3), 2-benzylquinazolin-4(3H)-one (4), cyclo-(Pro-Ile), cyclo-(Pro-Leu), cyclo-(Pro-Val), cyclo-(Pro-Phe), and cyclo-(Tyr-Pro) were isolated from the n-butyl alcohol extract of the marine-derived bacterium Bacillus cereus 041381. The new compounds were identified by spectroscopic analysis and chemical synthesis. Four optical isomers 5−8 were also synthesized. Compounds 1−8 all showed moderate antifungal activity against Candida albicans with MIC values of 1.3−15.6 μM. Compound 5 exhibits the most powerful antifungal activity, which may reveal that S-configuration and 2,3-double bond were necessary for antifungal activity, and the racemization at C-2 and C-3′ reduced the antifungal activity. |
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Keywords: | New quinazolinones alkaloids Antifungal activity Microbial metabolites Bacillus cereus Chemical synthesis |
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