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Open AccessArticle

Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388

by Lu-Ping Chi 1,2,3, Xiao-Ming Li 1,2, Li Li 1,2,3, Xin Li 1,2,* and Bin-Gui Wang 1,2,4,*
1
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
2
Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Wenhai Road 1, Qingdao 266237, China
3
University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, China
4
Center for Ocean Mega-Science, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, China
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2020, 18(3), 160; https://doi.org/10.3390/md18030160
Received: 8 February 2020 / Revised: 9 March 2020 / Accepted: 11 March 2020 / Published: 13 March 2020
(This article belongs to the Special Issue Bioactive Molecules from Marine Microorganisms)
Four 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 (610), 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 13, 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. View Full-Text
Keywords: Epicoccum nigrum; deep-sea-derived fungus; thiodiketopiperazines; diketopiperazine enantiomers; cytotocxic activity Epicoccum nigrum; deep-sea-derived fungus; thiodiketopiperazines; diketopiperazine enantiomers; cytotocxic activity
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MDPI and ACS Style

Chi, L.-P.; Li, X.-M.; Li, L.; Li, X.; Wang, B.-G. Cytotoxic Thiodiketopiperazine Derivatives from the Deep Sea-Derived Fungus Epicoccum nigrum SD-388. Mar. Drugs 2020, 18, 160.

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