New Hydroquinone Monoterpenoid and Cembranoid-Related Metabolites from the Soft Coral Sarcophyton tenuispiculatum

Abstract

Chemical investigation of the marine soft coral Sarcophyton tenuispiculatum resulted in the isolation of a 1,4-dihydrobenzoquinone, sarcotenuhydroquinone (1), three new cembranoids, sarcotenusenes A‒C (2‒4), and ten previously reported metabolites 5–14. The chemical structures of all isolated metabolites were determined by detailed spectroscopic analyses. In biological assays, anti-inflammatory, cytotoxic, and peroxisome proliferator-activated receptor γ (PPAR-γ) transcription factor assays of all compounds were performed. None of the isolated compounds were found to exhibit activity in the PPAR-γ transcription factor assay. The anti-inflammatory assays showed that (+)-7α,8β-dihydroxydeepoxysarcophine (13) inhibited the production of IL-1β to 56 ± 1% at a concentration of 30 µM in lipopolysaccharide (LPS)-stimulated J774A.1 macrophage cells. In addition, 1 and 2 were found to exhibit cytotoxicity towards a panel of cancer cell lines.

Cytotoxic Compounds from Alcyoniidae: An Overview of the Last 30 Years

“…Moreover, compound (2S,7S,8S)-sarcophytoxide ( 151), (2S,7R,8R)-sarcophytoxide (152), 3,4-dihydro-4α-hydroxy-∆2-sarcophine (154), and the hydroperoxide (155) showed cytotoxicity against HepG2 cells with (IC 50 values of 35.2 ± 4.4, 28.6 ± 3.4, 34.5 ± 4.2, and 36.4 ± 5.3 µM respectively. Furthermore, compounds sarcotenuhydroquinone (149) and sarcophytonin F (153) resulted cytotoxic toward the MDA-MB-231 cell line with an (IC 50 value of 36.4 ± 3.6 and 38.6 ± 5.0 µM, respectively [74].…”

Cembranoids of Soft Corals: Recent Updates and Their Biological Activities

“…The three novel cembranoids sarcotenusenes A-C 148–150 were mostly inactive in PPAR-ɣ transcription factor assay; cytotoxic assay towards MCF-7, MDA-MB-231, HepG2 and HeLa cell line; and inflammatory assay. Moreover, (2S, 7S, 8S)-sarcophytoxide 151 , (2S, 7R, 8R)-sarcophytoxide 152 , sarcophytonin F 153 , 3,4-dihydro-4α-hydroxy-∆ 2 -sarcophine 154 , A hydroperoxide obtained by autoxidation of dihydrofuranocembranoid 155 , and ( +)-7 α ,8 β -dihydroxydeepoxysarcophine 156 were also displayed various results on the abovementioned assay [ 46 ]. Additionaly, six cembranoids were isolated from S. roseum collected in Dahab, Red Sea, Egypt.…”

“…Whilst compound 151–152, 154–155 showed cytotoxicity against HepG2 with IC 50 value of 35.2 ± 4.4; 28.6 ± 3.4; 34.5 ± 4.2 and 36.4 ± 5.3 µm, respectively. Furthermore, compound 153 showed cytotoxicity towards MDA-MB-231 cell line with an IC 50 value of 38.6 ± 5.0 µm [ 46 ].…”

“…[ 45 ]. In addition, Sarcophyton tenuispiculatum contained 156 which possessed anti-inflammatory activity through inhibiting the production of IL-1β to 56 ± 1% in LPS-stimulated murine macrophage J774A.1 cell at a concentration of 30 µm [ 46 ]. New briaranes 357 and 360 exhibited anti-inflammatory activity by enhancing the release of iNOS (142.03 and 134.11%, respectively) and COX-2 (159.21 and 196.03%, respectively) in LPS-stimulated RAW 264.7 macrophage cells at concentration of 10 µM [ 93 ].…”

Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

“…These secondary metabolites help the organisms to defend themselves against the predators and adapt to the environment stress [ 5 ]. Furthermore, some of the isolates have been demonstrated to possess various biological activities, such as cytotoxic [ 6 , 7 , 8 , 9 , 10 , 11 , 12 ], anti-inflammatory [ 6 , 7 , 13 , 14 , 15 , 16 , 17 , 18 ], neuroprotective [ 19 ], antibacterial [ 19 ], and antiviral activities [ 12 , 20 ]. The diversified structures and various biological applications of marine natural products thus prompt us to further explore the secondary metabolites from organisms of the Sarcophyton genus.…”