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. 2016 Jan 26;21(2):150.
doi: 10.3390/molecules21020150.

Imidazole Alkaloids from the South China Sea Sponge Pericharax heteroraphis and Their Cytotoxic and Antiviral Activities

Kai-Kai Gong  1   2 , Xu-Li Tang  3 , Yi-Sheng Liu  4 , Ping-Lin Li  5 , Guo-Qiang Li  6
Affiliations

Imidazole Alkaloids from the South China Sea Sponge Pericharax heteroraphis and Their Cytotoxic and Antiviral Activities

Kai-Kai Gong et al. Molecules. .

Abstract

Marine sponges continue to serve as a rich source of alkaloids possessing interesting biological activities and often exhibiting unique structural frameworks. In the current study, chemical investigation on the marine sponge Pericharax heteroraphis collected from the South China Sea yielded one new imidazole alkaloid named naamidine J (1) along with four known ones (2-5). Their structures were established by extensive spectroscopic methods and comparison of their data with those of the related known compounds. All the isolates possessed a central 2-aminoimidazole ring, substituted by one or two functionalized benzyl groups in some combination of the C4 and C5 positions. The cytotoxicities against selected HL-60, HeLa, A549 and K562 tumor cell lines and anti-H1N1 (Influenza a virus (IAV)) activity for the isolates were evaluated. Compounds 1 and 2 exhibited cytotoxicities against the K562 cell line with IC50 values of 11.3 and 9.4 μM, respectively. Compound 5 exhibited weak anti-H1N1 (influenza a virus, IAV) activity with an inhibition ratio of 33%.

Keywords: 2-aminoimidazole alkaloids; Pericharax heteroraphis; anti-H1N1 activity; cytotoxicities; sponge.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of compounds 1–5.
Figure 2
Figure 2
Structure of naamidine A.
Figure 3
Figure 3
Selected key HMBC and NOESY correlations of compound 1.
Figure 4
Figure 4
The HPLC and UV chromatograms of 2-aminoimidazole alkaloids.
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