有机化学 ›› 2018, Vol. 38 ›› Issue (10): 2798-2804.DOI: 10.6023/cjoc201803017 上一篇    下一篇

研究简报

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).

正红树根泥来源的沙门柏干酪青霉(Penicillium camemberti) OUCMDZ-1492在寡营养条件下能够产生一类不同于富营养条件下的代谢产物,具有细菌群体感应抑制活性.采用活性跟踪的分离方法并对其中的外消旋体进行手性拆分,得到了5个α-吡喃酮类化合物;通过波谱分析、电子圆二色谱(ECD)的测量与化学模拟计算,其结构分别被鉴定为:(RE)-6-甲基-5-(3-羟基-1-丁烯基)-4-甲氧基-2-吡喃酮(1,命名为pyrenocine P)、pyrenocine A(2)、(R)-pyrenocine B(3)、(R)-(—)-pyrenocine E(4)和(S)-(+)-pyrenocine E(5),其中化合物1为新化合物、化合物35的绝对构型为首次确定.化合物23对紫色杆菌(Chromobacterium violaceum) CV026显示出较强的群体感应抑制活性,最小抑制浓度MIC分别为0.16和1.0 mg·mL-1[阳性药(Z)-4-溴-5-溴亚甲基-2-呋喃酮(C-30)的MIC为0.08 mg·mL-1].

关键词: 红树林真菌, 沙门柏干酪青霉, α-吡喃酮类化合物, 紫色杆菌CV026, 群体感应抑制活性

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