New Biscembranoids Sardigitolides A–D and Known Cembranoid-Related Compounds from Sarcophyton digitatum: Isolation, Structure Elucidation, and Bioactivities

Abstract

Chemical examination from the cultured soft coral Sarcophyton digitatum resulted in the isolation and structural identification of four new biscembranoidal metabolites, sardigitolides A–D (1–4), along with three previously isolated biscembranoids, sarcophytolide L (5), glaucumolide A (6), glaucumolide B (7), and two known cembranoids (8 and 9). The chemical structures of all isolates were elucidated on the basis of 1D and 2D NMR spectroscopic analyses. Additionally, in order to discover bioactivity of marine natural products, 1–8 were examined in terms of their inhibitory potential against the upregulation of inflammatory factor production in lipopolysaccharide (LPS)-stimulated murine macrophage J774A.1 cells and their cytotoxicities against a limited panel of cancer cells. The anti-inflammatory results showed that at a concentration of 10 µg/mL, 6 and 8 inhibited the production of IL-1β to 68 ± 1 and 56 ± 1%, respectively, in LPS-stimulated murine macrophages J774A.1. Furthermore, sardigitolide B (2) displayed cytotoxicities toward MCF-7 and MDA-MB-231 cancer cell lines with the IC50 values of 9.6 ± 3.0 and 14.8 ± 4.0 µg/mL, respectively.

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

“…Cell lines were purchased from the American Type Culture Collection (Rockville, MD, USA). Cytotoxicity testing for all compounds 1 – 14 was carried out using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay as in the previous report [ 31 , 32 ]. Doxorubicin, the positive control in the MTT assay, showed cytotoxicity towards MCF-7, MDA-MB-231, HepG2, and HeLa cancer cell lines, with IC 50 values of 6.8 ± 1.4, 6.3 ± 1.2, 9.6 ± 1.8, and 8.1 ± 2.1 ( µ M), respectively.…”

“…Murine macrophage cell line J774A.1 was purchased from the American Type Culture Collection. Screening about the generation of pro-inflammatory cytokines in LPS-stimulated J774A.1 macrophage cells was carried out according to the previous report [ 32 ]. The concentrations of the produced cytokines were measured using ELISA according to the previous work [ 33 ] and manufacturer′s protocol.…”

Cembranoids of Soft Corals: Recent Updates and Their Biological Activities

“…The only known cembranoid collected from this species namely isosarcophytonolide D 147 . The reported cembrane-type diterpenoid from S. digitatum was reported to display various anti-cancer and anti-inflammatory activities [ 45 ]. Another study reported nine cembranoids from Sarcophyton tenuispiculatum which culture at Kaohsiung Medical University, Taiwan.…”

“…In addition, 146 exhibited cytotoxicity towards MCF-7, MDA-MB-231, and HepG2 with IC 50 value of 9.4 ± 3.0; 17.8 ± 4.5; 14.9 ± 4.2 µg/mL, respectively. Lastly, 147 showed cytotoxicity towards MCF-7 with an IC 50 value of 10.9 ± 4.3 µg/mL [ 45 ].…”

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.…”