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Isolation and characterization of three pairs of verrucosidin epimers from the marine sediment-derived fungus Penicillium cyclopium and configuration revision of penicyrone A and related analogues
Li, Yan-He1,2,3; Mandi, Attila4; Li, Hong-Lei1,2,5; Li, Xiao-Ming1,2,5; Li, Xin1,2,5; Meng, Ling-Hong1,2,5; Yang, Sui-Qun1,2,5; Shi, Xiao-Shan1,2,5; Kurtan, Tibor4; Wang, Bin-Gui1,2,3,5
2023-05-28
Source PublicationMARINE LIFE SCIENCE & TECHNOLOGY
ISSN2096-6490
Pages9
Corresponding AuthorKurtan, Tibor(kurtan.tibor@science.unideb.hu) ; Wang, Bin-Gui(wangbg@ms.qdio.ac.cn)
AbstractVerrucosidins, a methylated alpha-pyrone class of polyketides rarely reported upon, have been implicated in one or more neurological diseases. Despite the significance of verrucosidins as neurotoxins, the absolute configurations 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 identified 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 configurations 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 configurational assignment of penicyrone A demonstrated that the previously reported C-6 absolute configuration 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.
KeywordMarine-derived fungus Penicillium cyclopium Verrucosidin derivatives TDDFT-ECD calculations Mosher's method Antimicrobial activity
DOI10.1007/s42995-023-00173-2
Indexed BySCI
Language英语
Funding ProjectNational Natural Science Foundation of China[U2006203] ; National Major Science and Technology Infrastructure from the Chinese Academy of Sciences ; National Research, Development, and Innovation Office[FK134653] ; National Research, Development, and Innovation Office[KEXUE2020GZ02] ; Governmental Information-Technology Development Agency (KIFUE) ; Senior User Project of RV KEXUE ; [K138672]
WOS Research AreaMarine & Freshwater Biology
WOS SubjectMarine & Freshwater Biology
WOS IDWOS:000995924400001
PublisherSPRINGERNATURE
WOS KeywordDERIVATIVES ; ECD
Citation statistics
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/183169
Collection实验海洋生物学重点实验室
Corresponding AuthorKurtan, Tibor; Wang, Bin-Gui
Affiliation1.Chinese Acad Sci, Inst Oceanol, CAS & Shandong Prov Key Lab Expt Marine Biol, Qingdao 266071, Peoples R China
2.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Qingdao 266071, Peoples R China
3.Univ Chinese Acad Sci, Sch Marine Sci, Beijing 100049, Peoples R China
4.Univ Debrecen, Dept Organ Chem, Egyet Ter 1, H-4032 Debrecen, Hungary
5.Chinese Acad Sci, Ctr Ocean Mega Sci, Qingdao 266071, Peoples R China
First Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Corresponding Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Recommended Citation
GB/T 7714
Li, Yan-He,Mandi, Attila,Li, Hong-Lei,et al. Isolation and characterization of three pairs of verrucosidin epimers from the marine sediment-derived fungus Penicillium cyclopium and configuration revision of penicyrone A and related analogues[J]. MARINE LIFE SCIENCE & TECHNOLOGY,2023:9.
APA Li, Yan-He.,Mandi, Attila.,Li, Hong-Lei.,Li, Xiao-Ming.,Li, Xin.,...&Wang, Bin-Gui.(2023).Isolation and characterization of three pairs of verrucosidin epimers from the marine sediment-derived fungus Penicillium cyclopium and configuration revision of penicyrone A and related analogues.MARINE LIFE SCIENCE & TECHNOLOGY,9.
MLA Li, Yan-He,et al."Isolation and characterization of three pairs of verrucosidin epimers from the marine sediment-derived fungus Penicillium cyclopium and configuration revision of penicyrone A and related analogues".MARINE LIFE SCIENCE & TECHNOLOGY (2023):9.
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