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  

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

作　　者：樊亚琴[1] 朱国良 王乂[1] 朱晓翠 宫倩红[1] 贾茜 付鹏[1] 朱伟明[1] Fan Yaqin;Zhu Guoliang;Wang Yi;Zhu Xiaocui;Gong Qianhong;Jia Qian;Fu Peng;Zhu Weiming(Key Laboratory of Marine Drugs,Ministry Education of China,School of Medicine and Pharmacy,Ocean University of China,Qingdao 26600)

机构地区：[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

出　　处：《有机化学》2018年第10期2798-2804,共7页Chinese Journal of Organic Chemistry

基　　金：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~~

摘　　要：正红树根泥来源的沙门柏干酪青霉(Penicilliumcamemberti)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:(R,E)-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3～5的绝对构型为首次确定.化合物2和3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].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-2 H-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（5 H）-one（C-30）, a positive control, was 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 

分 类 号：R915[医药卫生—微生物与生化药学]