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Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328
Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China
* Authors to whom correspondence should be addressed.
Received: 16 January 2013; in revised form: 6 March 2013 / Accepted: 6 March 2013 / Published: 28 March 2013
Abstract: Five new diketopiperazine derivatives, (3Z,6E)-1-N-methyl-3-benzy lidene-6-(2S-methyl-3-hydroxypropylidene)piperazine-2,5-dione (1), (3Z,6E)-1-N-methyl-3-benzylidene-6-(2R-methyl-3-hydroxypropylidene)piperazine-2,5-dione (2), (3Z,6Z)-3- (4-hydroxybenzylidene)-6-isobutylidenepiperazine-2,5-dione (3), (3Z,6Z)-3-((1H-imidazol-5-yl)-methylene)-6-isobutylidenepiperazine-2,5-dione (4), and (3Z,6S)-3-benzylidene-6-(2S-but-2-yl)piperazine-2,5-dione (5), were isolated from the marine-derived actinomycete Streptomyces sp. FXJ7.328. The structures of 1–5 were determined by spectroscopic analysis, CD exciton chirality, the modified Mosher’s, Marfey’s and the C3 Marfey’s methods. Compound 3 showed modest antivirus activity against influenza A (H1N1) virus with an IC50 value of 41.5 ± 4.5 μM. In addition, compound 6 and 7 displayed potent anti-H1N1 activity with IC50 value of 28.9 ± 2.2 and 6.8 ± 1.5 μM, respectively. Due to the lack of corresponding data in the literature, the 13C NMR data of (3Z,6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione (6) were also reported here for the first time.
Keywords: Streptomyces; diketopiperazine derivatives; antivirus activity; H1N1
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MDPI and ACS Style
Wang, P.; Xi, L.; Liu, P.; Wang, Y.; Wang, W.; Huang, Y.; Zhu, W. Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328. Mar. Drugs 2013, 11, 1035-1049.
Wang P, Xi L, Liu P, Wang Y, Wang W, Huang Y, Zhu W. Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328. Marine Drugs. 2013; 11(4):1035-1049.
Wang, Pei; Xi, Lijun; Liu, Peipei; Wang, Yi; Wang, Wei; Huang, Ying; Zhu, Weiming. 2013. "Diketopiperazine Derivatives from the Marine-Derived Actinomycete Streptomyces sp. FXJ7.328." Mar. Drugs 11, no. 4: 1035-1049.