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.
Highlights
Marine natural products are diverse in terms of chemical structures as well as biological activities.The Red Sea serves as an epicenter for marine bio-diversity with a high endemic biota
Collected specimens of S. glaucum were immediately frozen in dry ice and kept at −20 °C
Precedent from soft coral literature led to the assumption of a cembranoid-skeleton backbone [19]
Summary
Marine natural products are diverse in terms of chemical structures as well as biological activities. During the past 20 years, thousands of novel marine metabolites have been identified and assayed for anticancer activity [17] Most of these drug leads are identified by high-throughput in vitro screening via a cost-effective testing of cancer cell lines derived from human and rodent sources. We report the isolation of three new and two known cembranolides (Chart 1) from an ethyl acetate extraction of the Red Sea soft coral Sarcophyton glaucum. Structures of these isolated metabolites were elucidated by 1D and 2D spectroscopic techniques, while the absolute configuration of 1 and 2 were confirmed by X-ray diffraction and circular dichroism (CD) analyses.
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