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. 2013 Mar 28;11(4):1035-49.
doi: 10.3390/md11041035.

Diketopiperazine derivatives from the marine-derived actinomycete Streptomyces sp. FXJ7.328

Pei Wang  1 , Lijun Xi, Peipei Liu, Yi Wang, Wei Wang, Ying Huang, Weiming Zhu
Affiliations
Free PMC article

Diketopiperazine derivatives from the marine-derived actinomycete Streptomyces sp. FXJ7.328

Pei Wang et al. Mar Drugs. .
Free PMC article

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.

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Figures

Figure 1
Figure 1
Chemical structures of compounds 1–10 from Streptomyces sp. FXJ7.328.
Figure 2
Figure 2
Selected 2D NMR correlations for 1–5.
Figure 3
Figure 3
The stable conformers of 1c and 2c and the measured CD curve for p-bromobenzoate 1c.
Figure 4
Figure 4
The postulated biosynthetic pathway of 1–3 and 5–8.
Figure 5
Figure 5
The structure-activity relationship (SAR) of compounds 3–7 and 9 for anti-H1N1 viral activity.
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