Citation: Fan Yaqin, Zhu Guoliang, Wang Yi, Zhu Xiaocui, Gong Qianhong, Jia Qian, Fu Peng, Zhu Weiming. α-Pyronoids with Quorum Sensing Inhibitory Activity from the Mangrove Fungus Penicillium camemberti OUCMDZ-1492[J]. Chinese Journal of Organic Chemistry, ;2018, 38(10): 2798-2804. doi: 10.6023/cjoc201803017 shu

α-Pyronoids with Quorum Sensing Inhibitory Activity from the Mangrove Fungus Penicillium camemberti OUCMDZ-1492

Key Laboratory of Marine Drugs, Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003

Corresponding author: Zhu Weiming, weimingzhu@ouc.edu.cn
Received Date: 13 March 2018
Revised Date: 24 April 2018
Available Online: 3 October 2018
Fund Project: the National Natural Science Foundation of China 81373298Project supported by the National Natural Science Foundation of China-Guangdong Fund Joint Project (No. U1501221) and the National Natural Science Foundation of China (Nos. 81561148012, 81373298)the National Natural Science Foundation of China-Guangdong Fund Joint Project U1501221the National Natural Science Foundation of China 81561148012

Figures(4)

The mangrove fungus Penicillium camemberti OUCMDZ-1492 produced a new class of compounds under the oligotrophic condition, which were different from those under the eutrophic condition. Bioassay-guided isolation and chiral resolution for the racemic mixture resulted in the harvest of five α-pyronoids. Their structures were ideinfied as (R, E)-5-(3-hydroxybut-1-en-1-yl)-4-methoxy-6-methyl-2H-pyran-2-one (1), pyrenocine A (2), (R)-pyrenocine B (3), (R)-(－)-pyrenocine E (4) and (S)-(+)-pyrenocine E (5). Their structures, including absolute configurations, were elucidated on the basis of spectral analysis, electronic circular dichroism (ECD) spectra, quantum chemical calculation, and chiral separation. New compound 1 was named as pyrenocine P, and the absolute configurations of compounds 3~5 were determined for the first time. Compounds 2 and 3 showed potent quorum sensing inhibitory activity in Chromobacterium violaceum CV026 with the minimal inhibitory concentrations of 0.16 and 1.0 mg·mL^-1, respectively. The minimum inhibitory concentration (MIC) value of (Z)-4-bromo-5-(bromomethylene)-furan-2 (5H)-one (C-30), a positive control, was 0.08 mg·mL^-1.
- mangrove fungi,
- Penicillium camemberti,
- α-pyronoid,
- chromobacterium violaceum CV026,
- quorum sensing inhibitory activity
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