金钗石斛 A-C，三种二聚硝基苯反式环氧酰胺，由深海来源真菌 Penicillium chrysogenum SCSIO41001 产生。
Chrysamides A-C, Three Dimeric Nitrophenyl trans-Epoxyamides Produced by the Deep-Sea-Derived Fungus Penicillium chrysogenum SCSIO41001.
机构信息
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Matria Medica/RNAM Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences , Guangzhou 510301, China.
Department of Chemistry, Jinan University , Guangzhou 510632, China.
出版信息
Org Lett. 2016 Aug 5;18(15):3650-3. doi: 10.1021/acs.orglett.6b01699. Epub 2016 Jul 21.
Three dimeric nitrophenyl trans-epoxyamides, chrysamides A-C (1-3), were obtained from the deep-sea-derived fungus Penicillium chrysogenum SCSIO41001. Their structures were characterized by spectroscopic analysis, electronic circular dichroism computations, and X-ray single-crystal diffraction analysis. Notably, compound 1 possesses a novel centrosymmetric dimer skeleton featuring an unprecedented 7-oxa-2,5-diazabicyclo[2.2.1]heptane ring system, which represents the first example of dimeric nitrophenyl trans-epoxyamide in nature. Compound 3 suppresses the production of proinflammatory cytokine interleukin-17. A possible biosynthetic pathway of 1-3 was proposed.
从深海来源的真菌青霉属（Penicillium）SCSIO41001 中分离得到三种二聚型硝基苯反式环氧酰胺，即 chrysamides A-C（1-3）。通过光谱分析、电子圆二色性计算和 X 射线单晶衍射分析对其结构进行了表征。值得注意的是，化合物 1 具有新颖的中心对称二聚骨架，其中包含一个前所未有的 7-氧杂-2,5-二氮杂双环[2.2.1]庚烷环系统，这是自然界中二聚型硝基苯反式环氧酰胺的首例。化合物 3 抑制前炎性细胞因子白细胞介素-17 的产生。提出了 1-3 的可能生物合成途径。
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