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Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388
Chi, Lu-Ping1,2,3; Li, Xiao-Ming1,2; Li, Li1,2,3; Li, Xin1,2; Wang, Bin-Gui1,2,4
2020-03-01
Source PublicationMARINE DRUGS
Volume18Issue:3Pages:12
Corresponding AuthorLi, Xin(lixin@qdio.ac.cn) ; Wang, Bin-Gui(wangbg@ms.qdio.ac.cn)
AbstractFour new thiodiketopiperazine alkaloids, namely, 5'-hydroxy-6'-ene-epicoccin G (1), 7-methoxy-7'-hydroxyepicoccin G (2), 8'-acetoxyepicoccin D (3), and 7'-demethoxyrostratin C (4), as well as a pair of new enantiomeric diketopiperazines, (+/-)-5-hydroxydiphenylalazine A (5), along with five known analogues (6-10), were isolated and identified from the culture extract of Epicoccum nigrum SD-388, a fungus obtained from deep-sea sediments (-4500 m). Their structures were established on the basis of detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis confirmed the structures and established the absolute configurations of compounds 1-3, while the absolute configurations for compounds 4 and 5 were determined by ECD calculations. Compounds 4 and 10 showed potent activity against Huh7.5 liver tumor cells, which were comparable to that of the positive control, sorafenib, and the disulfide bridge at C-2/C-2' is likely essential for the activity.
KeywordEpicoccum nigrum deep-sea-derived fungus thiodiketopiperazines diketopiperazine enantiomers cytotocxic activity
DOI10.3390/md18030160
Indexed BySCI
Language英语
Funding ProjectStrategic Priority Research Program of the Chinese Academy of Sciences[XDA22050401] ; Aoshan Scientific and Technological Innovation Project of Qingdao National Laboratory for Marine Science and Technology[2016ASKJ14] ; China Postdoctoral Science Foundation[2017M612360] ; Research Vessel KEXUE of the National Major Science and Technology Infrastructure from the Chinese Academy of Sciences[KEXUE2018G28] ; Taishan Scholar Project from Shandong Province
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000524256300040
PublisherMDPI
Citation statistics
Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.qdio.ac.cn/handle/337002/167152
Collection实验海洋生物学重点实验室
Corresponding AuthorLi, Xin; Wang, Bin-Gui
Affiliation1.Chinese Acad Sci, Inst Oceanol, Key Lab Expt Marine Biol, Nanhai Rd 7, Qingdao 266071, Peoples R China
2.Qingdao Natl Lab Marine Sci & Technol, Lab Marine Biol & Biotechnol, Wenhai Rd 1, Qingdao 266237, Peoples R China
3.Univ Chinese Acad Sci, Yuquan Rd 19A, Beijing 100049, Peoples R China
4.Chinese Acad Sci, Ctr Ocean Megasci, Nanhai Rd 7, Qingdao 266071, Peoples R China
First Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences
Corresponding Author AffilicationInstitute of Oceanology, Chinese Academy of Sciences;  Center for Ocean Mega-Science, Chinese Academy of Sciences
Recommended Citation
GB/T 7714
Chi, Lu-Ping,Li, Xiao-Ming,Li, Li,et al. Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388[J]. MARINE DRUGS,2020,18(3):12.
APA Chi, Lu-Ping,Li, Xiao-Ming,Li, Li,Li, Xin,&Wang, Bin-Gui.(2020).Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388.MARINE DRUGS,18(3),12.
MLA Chi, Lu-Ping,et al."Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388".MARINE DRUGS 18.3(2020):12.
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