Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum

Mohamed Elamir F. Hegazy; Amira M. Gamal Eldeen; Abdelaaty A. Shahat; Fathy F. Abdel-Latif; Tarik A. Mohamed; Bruce R. Whittlesey; Paul W. Paré

doi:10.3390/md10010209

Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum

Mohamed Elamir F. Hegazy, Amira M. Gamal Eldeen, Abdelaaty A. Shahat, Fathy F. Abdel-Latif, Tarik A. Mohamed, Bruce R. Whittlesey, Paul W. Paré

Chemistry and Biochemistry

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55 Scopus citations

Abstract

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 P450 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.

Original language	English
Pages (from-to)	209-222
Number of pages	14
Journal	Marine Drugs
Volume	10
Issue number	1
DOIs	https://doi.org/10.3390/md10010209
State	Published - Jan 2012

Keywords

Cancer chemo-preventive activity
Diterpenes
Sarcophyton glaucum
Soft coral

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title = "Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum",

abstract = "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 P450 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.",

keywords = "Cancer chemo-preventive activity, Diterpenes, Sarcophyton glaucum, Soft coral",

author = "Hegazy, {Mohamed Elamir F.} and {Gamal Eldeen}, {Amira M.} and Shahat, {Abdelaaty A.} and Abdel-Latif, {Fathy F.} and Mohamed, {Tarik A.} and Whittlesey, {Bruce R.} and Par{\'e}, {Paul W.}",

year = "2012",

month = jan,

doi = "10.3390/md10010209",

language = "English",

volume = "10",

pages = "209--222",

journal = "Marine Drugs",

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T1 - Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum

AU - Hegazy, Mohamed Elamir F.

AU - Gamal Eldeen, Amira M.

AU - Shahat, Abdelaaty A.

AU - Abdel-Latif, Fathy F.

AU - Mohamed, Tarik A.

AU - Whittlesey, Bruce R.

AU - Paré, Paul W.

PY - 2012/1

Y1 - 2012/1

N2 - 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 P450 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.

AB - 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 P450 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.

KW - Cancer chemo-preventive activity

KW - Diterpenes

KW - Sarcophyton glaucum

KW - Soft coral

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DO - 10.3390/md10010209

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SN - 1660-3397

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EP - 222

JO - Marine Drugs

JF - Marine Drugs

IS - 1

ER -

Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum

Abstract

Keywords

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