Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum

A chemical investigation of an ethyl acetate extract of the Red Sea soft coral Sarcophyton glaucum has led to the isolation of two peroxide diterpenes, 11(S) hydroperoxylsarcoph-12(20)-ene (1), and 12(S)-hydroperoxylsarcoph-10-ene (2), as well as 8-epi-sarcophinone (3). In addition to these three ne...

Descripción completa

Detalles Bibliográficos
Autores principales: Hegazy, Mohamed-Elamir F., Gamal Eldeen, Amira M., Shahat, Abdelaaty A., Abdel-Latif, Fathy F., Mohamed, Tarik A., Whittlesey, Bruce R., Paré, Paul W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3280536/
https://www.ncbi.nlm.nih.gov/pubmed/22363231
http://dx.doi.org/10.3390/md10010209
_version_ 1782223843001106432
author Hegazy, Mohamed-Elamir F.
Gamal Eldeen, Amira M.
Shahat, Abdelaaty A.
Abdel-Latif, Fathy F.
Mohamed, Tarik A.
Whittlesey, Bruce R.
Paré, Paul W.
author_facet Hegazy, Mohamed-Elamir F.
Gamal Eldeen, Amira M.
Shahat, Abdelaaty A.
Abdel-Latif, Fathy F.
Mohamed, Tarik A.
Whittlesey, Bruce R.
Paré, Paul W.
author_sort Hegazy, Mohamed-Elamir F.
collection PubMed
description A chemical investigation of an ethyl acetate extract of the Red Sea soft coral Sarcophyton glaucum has led to the isolation of two peroxide diterpenes, 11(S) hydroperoxylsarcoph-12(20)-ene (1), and 12(S)-hydroperoxylsarcoph-10-ene (2), as well as 8-epi-sarcophinone (3). In addition to these three new compounds, two known structures were identified including: ent-sarcophine (4) and sarcophine (5). Structures were elucidated by spectroscopic analysis, with the relative configuration of 1 and 2 confirmed by X-ray diffraction. Isolated compounds were found to be inhibitors of cytochrome P(450) 1A activity as well as inducers of glutathione S-transferases (GST), quinone reductase (QR), and epoxide hydrolase (mEH) establishing chemo-preventive and tumor anti-initiating activity for these characterized metabolites.
format Online
Article
Text
id pubmed-3280536
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-32805362012-02-23 Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum Hegazy, Mohamed-Elamir F. Gamal Eldeen, Amira M. Shahat, Abdelaaty A. Abdel-Latif, Fathy F. Mohamed, Tarik A. Whittlesey, Bruce R. Paré, Paul W. Mar Drugs Article A chemical investigation of an ethyl acetate extract of the Red Sea soft coral Sarcophyton glaucum has led to the isolation of two peroxide diterpenes, 11(S) hydroperoxylsarcoph-12(20)-ene (1), and 12(S)-hydroperoxylsarcoph-10-ene (2), as well as 8-epi-sarcophinone (3). In addition to these three new compounds, two known structures were identified including: ent-sarcophine (4) and sarcophine (5). Structures were elucidated by spectroscopic analysis, with the relative configuration of 1 and 2 confirmed by X-ray diffraction. Isolated compounds were found to be inhibitors of cytochrome P(450) 1A activity as well as inducers of glutathione S-transferases (GST), quinone reductase (QR), and epoxide hydrolase (mEH) establishing chemo-preventive and tumor anti-initiating activity for these characterized metabolites. MDPI 2012-01-18 /pmc/articles/PMC3280536/ /pubmed/22363231 http://dx.doi.org/10.3390/md10010209 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland http://creativecommons.org/licenses/by/3.0/ 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/).
spellingShingle Article
Hegazy, Mohamed-Elamir F.
Gamal Eldeen, Amira M.
Shahat, Abdelaaty A.
Abdel-Latif, Fathy F.
Mohamed, Tarik A.
Whittlesey, Bruce R.
Paré, Paul W.
Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum
title Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum
title_full Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum
title_fullStr Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum
title_full_unstemmed Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum
title_short Bioactive Hydroperoxyl Cembranoids from the Red Sea Soft Coral Sarcophyton glaucum
title_sort bioactive hydroperoxyl cembranoids from the red sea soft coral sarcophyton glaucum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3280536/
https://www.ncbi.nlm.nih.gov/pubmed/22363231
http://dx.doi.org/10.3390/md10010209
work_keys_str_mv AT hegazymohamedelamirf bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum
AT gamaleldeenamiram bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum
AT shahatabdelaatya bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum
AT abdellatiffathyf bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum
AT mohamedtarika bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum
AT whittleseybrucer bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum
AT parepaulw bioactivehydroperoxylcembranoidsfromtheredseasoftcoralsarcophytonglaucum

Ejemplares similares