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

Mar Drugs. 2016 Feb 4;14(2):28. doi: 10.3390/md14020028.

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.

Keywords: HIV-1; Red Sea; Stylissa carteri; marine bioprospecting; reverse transcriptase.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Alkaloids / toxicity
  • Animals
  • Anti-HIV Agents / isolation & purification
  • Anti-HIV Agents / pharmacology*
  • Anti-HIV Agents / toxicity
  • Cell Survival / drug effects
  • Chromatography, High Pressure Liquid / methods
  • HIV Infections / drug therapy
  • HIV Infections / virology
  • HIV Reverse Transcriptase / drug effects
  • HIV-1 / drug effects*
  • Humans
  • Mass Spectrometry / methods
  • Porifera / metabolism*
  • Secondary Metabolism
  • Virus Replication / drug effects

Substances

  • Alkaloids
  • Anti-HIV Agents
  • reverse transcriptase, Human immunodeficiency virus 1
  • HIV Reverse Transcriptase