Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2798-2804.DOI: 10.6023/cjoc201803017 Previous Articles     Next Articles

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红树林真菌Penicillium camemberti OUCMDZ-1492产生的细菌群体感应抑制活性的α-吡喃酮类化合物

樊亚琴, 朱国良, 王乂, 朱晓翠, 宫倩红, 贾茜, 付鹏, 朱伟明   

  1. 中国海洋大学医药学院 海洋药物教育部重点实验室 青岛 266003
  • 收稿日期:2018-03-13 修回日期:2018-04-24 发布日期:2018-05-03
  • 通讯作者: 朱伟明,E-mail:weimingzhu@ouc.edu.cn E-mail:weimingzhu@ouc.edu.cn
  • 基金资助:

    国家自然科学基金-广东联合基金(No.U1501221)、国家自然科学基金(Nos.81561148012,81373298)资助项目.

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

Fan Yaqin, Zhu Guoliang, Wang Yi, Zhu Xiaocui, Gong Qianhong, Jia Qian, Fu Peng, Zhu Weiming   

  1. Key Laboratory of Marine Drugs, Ministry Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003
  • Received:2018-03-13 Revised:2018-04-24 Published:2018-05-03
  • Contact: 10.6023/cjoc201803017 E-mail:weimingzhu@ouc.edu.cn
  • Supported by:

    Project 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 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 35 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.

Key words: mangrove fungi, Penicillium camemberti, α-pyronoid, chromobacterium violaceum CV026, quorum sensing inhibitory activity