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Mar. Drugs 2016, 14(2), 28; doi:10.3390/md14020028

Alkaloids from the Sponge Stylissa carteri Present Prospective Scaffolds for the Inhibition of Human Immunodeficiency Virus 1 (HIV-1)

1
Red Sea Research Center, Division of Biological and Environmental Science and Engineering, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia
2
Research Unit Analytical BioGeoChemistry, Helmholtz Zentrum Muenchen, 85764 Neuherberg, Germany
3
Institute of Virology, Helmholtz Zentrum Muenchen, German Research Center for Environmental Health, Ingolstädter Landstraße 1, D-85764 Neuherberg, Germany
4
Analytical Food Chemistry, Technical University of Munich, 85354 Freising Weihenstephan, Germany
5
Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Paul Long
Received: 21 July 2015 / Revised: 18 December 2015 / Accepted: 14 January 2016 / Published: 4 February 2016
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Abstract

The sponge Stylissa carteri is known to produce a number of secondary metabolites displaying anti-fouling, anti-inflammatory, and anti-cancer activity. However, the anti-viral potential of metabolites produced by S. carteri has not been extensively explored. In this study, an S. carteri extract was HPLC fractionated and a cell based assay was used to evaluate the effects of HPLC fractions on parameters of Human Immunodeficiency Virus (HIV-1) infection and cell viability. Candidate HIV-1 inhibitory fractions were then analyzed for the presence of potential HIV-1 inhibitory compounds by mass spectrometry, leading to the identification of three previously characterized compounds, i.e., debromohymenialdisine (DBH), hymenialdisine (HD), and oroidin. Commercially available purified versions of these molecules were re-tested to assess their antiviral potential in greater detail. Specifically, DBH and HD exhibit a 30%–40% inhibition of HIV-1 at 3.1 μM and 13 μM, respectively; however, both exhibited cytotoxicity. Conversely, oroidin displayed a 50% inhibition of viral replication at 50 μM with no associated toxicity. Additional experimentation using a biochemical assay revealed that oroidin inhibited the activity of the HIV-1 Reverse Transcriptase up to 90% at 25 μM. Taken together, the chemical search space was narrowed and previously isolated compounds with an unexplored anti-viral potential were found. Our results support exploration of marine natural products for anti-viral drug discovery. View Full-Text
Keywords: Stylissa carteri; marine bioprospecting; HIV-1; reverse transcriptase; Red Sea Stylissa carteri; marine bioprospecting; HIV-1; reverse transcriptase; Red Sea
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MDPI and ACS Style

O’Rourke, A.; Kremb, S.; Bader, T.M.; Helfer, M.; Schmitt-Kopplin, P.; Gerwick, W.H.; Brack-Werner, R.; Voolstra, C.R. Alkaloids from the Sponge Stylissa carteri Present Prospective Scaffolds for the Inhibition of Human Immunodeficiency Virus 1 (HIV-1). Mar. Drugs 2016, 14, 28.

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