Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370

doi:10.1016/j.bioorg.2020.104477

IOCAS-IR > 实验海洋生物学重点实验室

	Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370
	Yang, Sui-Qun 1,2; Mandi, Attila 3; Li, Xiao-Ming 1,2; Liu, Hui1 ; Li, Xin1,2 ; Kiraly, Sandor Balazs 3; Kurtan, Tibor 3; Wang, Bin-Gui1,2,4
	2021
发表期刊	BIOORGANIC CHEMISTRY
ISSN	0045-2068
卷号	106 页码:9
通讯作者	Kurtan, Tibor(kurtan.tibor@science.unideb.hu) ; Wang, Bin-Gui(wangbg@ms.qdio.ac.cn)
摘要	Eight phenalenone derivatives, including four new compounds, aceneoherqueinones A and B (1 and 2), (+)-aceatrovenetinone A (3a), and (+)-aceatrovenetinone B (3d), along with four known congeners, (-)-aceatrovenetinone A (3b), (-)-aceatrovenetinone B (3c), (-)-scleroderolide (4a), and (+)-scleroderolide (4b), were characterized from the marine mangrove-derived fungus Penicillium herquei MA-370. Among them, compounds 1 and 2 are rare phenalenone derivatives featuring cyclic ether unit between C-5 and C-2'. All of these compounds were subjected to chiral HPLC analysis, and the unstable stereoisomers 3a-3d, containing configurationally labile chirality centers, were characterized by online HPLC-ECD measurements supported with TDDFT-ECD calculations. The structures of these compounds were elucidated by detailed analysis of their NMR and mass spectroscopic data, and the absolute configuration of compound 1 was confirmed by X-ray diffraction analysis, while those of compounds 2 and 3a-3d were determined by TDDFT-ECD calculations of their ECD spectra. All of the isolated compounds were tested for the inhibitory activity against angiotensin-I-converting enzyme (ACE), and compounds 1 and 2 displayed activity with IC50 values 3.10 and 11.28 mu M, respectively. The intermolecular interaction and potential binding sites of 1 and 2 with ACE were elaborated by molecular docking, showing that compound 1 bound well with ACE via hydrogen interactions with residues Ala261, Gln618, Trp621, and Asn624, while compound 2 interacted with residues Asp358 and Tyr360.
关键词	Marine fungi Penicillium herquei Phenalenone derivatives ACE inhibitory activity Molecular docking
DOI	10.1016/j.bioorg.2020.104477
收录类别	SCI
语种	英语
资助项目	Natural Science Foundation of China[31570356] ; Natural Science Foundation of Shandong Province[ZR2019BD048] ; National Research, Development and Innovation Office (NKFI)[K120181] ; Janos Bolyai Research Scholarship of the Hungarian Academy of Sciences ; Taishan Scholar Project from Shandong Province of China[ts201511060]
WOS研究方向	Biochemistry & Molecular Biology ; Chemistry
WOS类目	Biochemistry & Molecular Biology ; Chemistry, Organic
WOS记录号	WOS:000605009700003
出版者	ACADEMIC PRESS INC ELSEVIER SCIENCE
引用统计	被引频次：13[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/337002/169918
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, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266237, Peoples R China 2.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Wenhai Rd 1, Qingdao 266237, Peoples R China 3.Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary 4.Chinese Acad Sci, Ctr Ocean Megasci, Nanhai Rd 7, 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; 中国科学院海洋大科学研究中心
推荐引用方式 GB/T 7714	Yang, Sui-Qun,Mandi, Attila,Li, Xiao-Ming,et al. Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370[J]. BIOORGANIC CHEMISTRY,2021,106:9.
APA	Yang, Sui-Qun.,Mandi, Attila.,Li, Xiao-Ming.,Liu, Hui.,Li, Xin.,...&Wang, Bin-Gui.(2021).Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370.BIOORGANIC CHEMISTRY,106,9.
MLA	Yang, Sui-Qun,et al."Separation and configurational assignment of stereoisomeric phenalenones from the marine mangrove-derived fungus Penicillium herquei MA-370".BIOORGANIC CHEMISTRY 106(2021):9.

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