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 confguration...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.展开更多
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。
文摘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.
