title: Diketopiperazine derivatives from the marine-derived actinomycete Streptomyces sp. FXJ7.328.
abstract: Five new diketopiperazine derivatives, (3Z,6E)-1-N-methyl-3-benzylidene-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.
authors.affiliation: Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. wangpei850212@163.com
authors.forename: Pei
authors.initials: P
authors.lastname: Wang
authors.forename: Lijun
authors.initials: L
authors.lastname: Xi
authors.forename: Peipei
authors.initials: P
authors.lastname: Liu
authors.forename: Yi
authors.initials: Y
authors.lastname: Wang
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Ying
authors.initials: Y
authors.lastname: Huang
authors.forename: Weiming
authors.initials: W
authors.lastname: Zhu
mesh_terms: D000998:Antiviral Agents / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D002942:Circular Dichroism; D054659:Diketopiperazines / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects; D020128:Inhibitory Concentration 50; D013057:Spectrum Analysis; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000998:Antiviral Agents; D054659:Diketopiperazines
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