Isolation and characterization of three pairs of verrucosidin epimers from the marine sediment‑derived fungus Penicillium cyclopium and confguration revision of penicyrone A and related analogues  

作　　者：Yan-He Li Attila Mándi Hong-Lei Li Xiao-Ming Li Xin Li Ling-Hong Meng Sui-Qun Yang Xiao-Shan Shi Tibor Kurtán Bin-Gui Wang 

机构地区：[1]CAS and Shandong Province Key Laboratory of Experimental Marine Biology,Institute of Oceanology,Chinese Academy of Sciences,and Laboratory of Marine Biology and Biotechnology at the Qingdao National Laboratory for Marine Science and Technology,Qingdao 266071,China [2]School of Marine Science,University of Chinese Academy of Sciences,Beijing 100049,China [3]Department of Organic Chemistry,University of Debrecen,Egyetem Tér 1,Debrecen 4032,Hungary [4]Center for Ocean Mega-Science,Chinese Academy of Sciences,Qingdao 266071,China

出　　处：《Marine Life Science & Technology》2023年第2期223-231,共9页海洋生命科学与技术（英文）

基　　金：Financial support by programs from the National Natural Science Foundation of China(U2006203);from the Senior User Project of RV KEXUE(KEXUE2020GZ02)is gratefully acknowledged.B.-G.W.appreciates the support of the RV KEXUE of the National Major Science and Technology Infrastructure from the Chinese Academy of Sciences(for sampling);The research work of the Hungarian authors was supported by the National Research,Development,and Innovation Ofce(K138672,FK134653).The Governmental Information-Technology Development Agency(KIFÜ)is acknowledged for CPU time。

摘　　要：Verrucosidins,a methylatedα-pyrone class of polyketides rarely reported upon,have been implicated in one or more neurological diseases.Despite the signifcance of verrucosidins as neurotoxins,the absolute confgurations of most of the derivatives have not been accurately characterized yet.In this study,three pairs of C-9 epimeric verrucosidin derivatives,including the known compounds penicyrones A and B(1a/1b)and 9-O-methylpenicyrones A and B(2a/2b),the new compounds 9-O-ethylpenicyrones A and B(3a/3b),together with the related known derivative verrucosidin(4),were isolated and identifed from the culture extract of Penicillium cyclopium SD-413,which was obtained from the marine sediment collected from the East China sea.Their structures were established based on an in-depth analysis of nuclear magnetic resonances(NMR)and mass spectroscopic data.Determination of the absolute confgurations of these compounds was accomplished by Mosher’s method and time-dependent density functional theory(TDDFT)calculations of electronic circular dichroism(ECD)and optical rotation(OR).The confgurational assignment of penicyrone A demonstrated that the previously reported C-6 absolute confguration of verrucosidin derivatives needs to be revised from(6S)to(6R).The 9R/9S epimers of compounds 1–3 were found to exhibit growth inhibition against some pathogenic bacteria,indicating that they have potential as lead compounds for the creation of antimicrobial agents.

关 键 词：Marine-derived fungus Penicillium cyclopium Verrucosidin derivatives TDDFT-ECD calculations Mosher’s method Antimicrobial activity 

分 类 号：Q178.53[生物学—水生生物学]