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

doi:10.1007/s42995-023-00173-2

IOCAS-IR > 实验海洋生物学重点实验室

	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, Attila 4; Li, Hong-Lei1,2,5 ; Li, Xiao-Ming 1,2,5; Li, Xin1,2,5 ; Meng, Ling-Hong1,2,5 ; Yang, Sui-Qun 1,2,5; Shi, Xiao-Shan1,2,5 ; Kurtan, Tibor 4; Wang, Bin-Gui1,2,3,5
	2023-05-28
发表期刊	MARINE LIFE SCIENCE & TECHNOLOGY
ISSN	2096-6490
页码	9
通讯作者	Kurtan, Tibor([email protected]) ; Wang, Bin-Gui([email protected])
摘要	Verrucosidins, 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.
关键词	Marine-derived fungus Penicillium cyclopium Verrucosidin derivatives TDDFT-ECD calculations Mosher's method Antimicrobial activity
DOI	10.1007/s42995-023-00173-2
收录类别	SCI
语种	英语
资助项目	National 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研究方向	Marine & Freshwater Biology
WOS类目	Marine & Freshwater Biology
WOS记录号	WOS:000995924400001
出版者	SPRINGERNATURE
WOS关键词	DERIVATIVES ; ECD
引用统计	被引频次：4[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/183169
专题	实验海洋生物学重点实验室
通讯作者	Kurtan, Tibor; Wang, Bin-Gui
作者单位	1.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
第一作者单位	中国科学院海洋研究所
通讯作者单位	中国科学院海洋研究所
推荐引用方式 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.