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

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

36 Citations (Scopus)

105 Downloads (Pure)

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.

Original language	English
Pages (from-to)	2937-2952
Number of pages	16
Journal	Marine Drugs
Volume	12
Issue number	5
DOIs	https://doi.org/10.3390/md12052937
Publication status	Published - 16 May 2014

Keywords

haliclona simulans
marine sponges
steroids
antitrypanosomal
anti-mycobacterial

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md12052937Licence: CC BY 4.0

spongemarinedrugs-12-02937-v3
© 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
Final published version, 1.14 MBLicence: CC BY 4.0

36 Citations
1 Poster

Metabolomics as a tool in the identification and production of new antibiotics from sponges and endosymbiotic bacteria
Viegelmann, C. V., Hoe Leong, C., Clements, C., Abdelmohsen, U. R., Hentschel, U., Margassery, L. M., Kennedy, J., Perrocco, D., Dobson, A. D. W. & Edrada-Ebel, R., Feb 2013.
Research output: Contribution to conference › Poster › peer-review

1 Hosting an academic visitor

Burkhardt Flemer
Edrada-Ebel, R. (Host)
1 Aug 2011 → 21 Aug 2011
Activity: Hosting a visitor types › Hosting an academic visitor

Cite this

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title = "Isolation and identification of antitrypanosomal and antimycobacterial active steroids from the sponge haliclona simulans",

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.",

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author = "Christina Viegelmann and Jennifer Parker and Thengtheng Ooi and Carol Clements and Gr{\'a}inne Abbott and Louise Young and Jonathan Kennedy and Dobson, {Alan D W} and RuAngelie Edrada-Ebel",

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T1 - Isolation and identification of antitrypanosomal and antimycobacterial active steroids from the sponge haliclona simulans

AU - Viegelmann, Christina

AU - Parker, Jennifer

AU - Ooi, Thengtheng

AU - Clements, Carol

AU - Abbott, Gráinne

AU - Young, Louise

AU - Kennedy, Jonathan

AU - Dobson, Alan D W

AU - Edrada-Ebel, RuAngelie

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Y1 - 2014/5/16

N2 - 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.

AB - 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.

KW - haliclona simulans

KW - marine sponges

KW - steroids

KW - antitrypanosomal

KW - anti-mycobacterial

U2 - 10.3390/md12052937

DO - 10.3390/md12052937

M3 - Article

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SP - 2937

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JO - Marine Drugs

JF - Marine Drugs

IS - 5

ER -

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

Abstract

Keywords

UN SDGs

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Research output

Metabolomics as a tool in the identification and production of new antibiotics from sponges and endosymbiotic bacteria

Activities

Burkhardt Flemer

Cite this