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
收稿日期: 2018-03-13
修回日期: 2018-04-24
网络出版日期: 2018-05-03
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
Received date: 2018-03-13
Revised date: 2018-04-24
Online published: 2018-05-03
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：（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].
樊亚琴 , 朱国良 , 王乂 , 朱晓翠 , 宫倩红 , 贾茜 , 付鹏 , 朱伟明 . 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[J]. 有机化学, 2018 , 38(10) : 2798 -2804 . DOI: 10.6023/cjoc201803017
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.
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