Isolation and identification of antitrypanosomal and antimycobacterial active steroids from the sponge Haliclona simulans

Christina Viegelmann; Jennifer Parker; Thengtheng Ooi; Carol Clements; Gráinne Abbott; Louise Young; Jonathan Kennedy; Alan D W Dobson; RuAngelie Edrada-Ebel

doi:10.3390/md12052937

Isolation and identification of antitrypanosomal and antimycobacterial active steroids from the sponge Haliclona simulans

Mar Drugs. 2014 May 16;12(5):2937-52. doi: 10.3390/md12052937.

Authors

Christina Viegelmann¹, Jennifer Parker², Thengtheng Ooi³, Carol Clements⁴, Gráinne Abbott⁵, Louise Young⁶, Jonathan Kennedy⁷, Alan D W Dobson⁸, RuAngelie Edrada-Ebel⁹

Affiliations

¹ Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. christina.viegelmann@strath.ac.uk.
² Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. jennifer.parker.100@strath.ac.uk.
³ Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. thengthengooi@hotmail.com.
⁴ Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. c.j.clements@strath.ac.uk.
⁵ Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. grainne.abbott@strath.ac.uk.
⁶ Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. louise.c.young@strath.ac.uk.
⁷ Marine Biotechnology Centre, Environmental Research Institute, University College Cork, Lee Road, Cork, Ireland. jonathan.kennedy@ucc.ie.
⁸ Marine Biotechnology Centre, Environmental Research Institute, University College Cork, Lee Road, Cork, Ireland. A.Dobson@ucc.ie.
⁹ Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, The John Arbuthnott Building, 161 Cathedral Street, Glasgow, Scotland G4 0RE, UK. ruangelie.edrada-ebel@strath.ac.uk.

Abstract

The marine sponge Haliclona simulans collected from the Irish Sea yielded two new steroids: 24-vinyl-cholest-9-ene-3β,24-diol and 20-methyl-pregn-6-en-3β-ol,5a,8a-epidioxy, along with the widely distributed 24-methylenecholesterol. One of the steroids possesses an unusually short hydrocarbon side chain. The structures were elucidated using nuclear magnetic resonance spectroscopy and confirmed using electron impact- and high resolution electrospray-mass spectrometry. All three steroids possess antitrypanosomal and anti-mycobacterial activity. All the steroids were found to possess low cytotoxicity against Hs27 which was above their detected antitrypanosomal potent concentrations.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / pharmacology*
Cell Survival / drug effects
Humans
Hydroxycholesterols / chemistry
Hydroxycholesterols / isolation & purification
Hydroxycholesterols / pharmacology*
Molecular Conformation
Mycobacterium / drug effects*
Porifera / chemistry*
Pregnanes / chemistry
Pregnanes / isolation & purification
Pregnanes / pharmacology*
Trypanocidal Agents / chemistry
Trypanocidal Agents / isolation & purification
Trypanocidal Agents / pharmacology*
Trypanosoma / drug effects

Substances

20-methyl-pregn-6-en-3beta-ol,5a,8a-epidioxy
24-vinyl-cholest-9-ene-3beta,24-diol
Anti-Bacterial Agents
Hydroxycholesterols
Pregnanes
Trypanocidal Agents