Dactylospenes A–E, Sesterterpenes from the Marine Sponge <i>Dactylospongia elegans</i>
Hao-Bing Yu,
Bin-Bin Gu,
Arihiro Iwasaki,
Wen-Li Jiang,
Andrew Ecker,
Shu-Ping Wang,
Fan Yang,
Hou-Wen Lin
Affiliations
Hao-Bing Yu
Department of Marine Biomedicine and Polar Medicine, Naval Medical Center of PLA, Second Military Medical University, Shanghai 200433, China
Bin-Bin Gu
Research Center for Marine Drugs, State Key Laboratory of Oncogenes and Related Genes, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China
Arihiro Iwasaki
Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan
Wen-Li Jiang
Department of Biochemistry and Molecular Biology, College of Basic Medical Sciences, Second Military Medical University, Shanghai 200433, China
Andrew Ecker
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, CA 92093, USA
Shu-Ping Wang
Research Center for Marine Drugs, State Key Laboratory of Oncogenes and Related Genes, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China
Fan Yang
Research Center for Marine Drugs, State Key Laboratory of Oncogenes and Related Genes, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China
Hou-Wen Lin
Research Center for Marine Drugs, State Key Laboratory of Oncogenes and Related Genes, School of Medicine, Shanghai Jiao Tong University, Shanghai 200127, China
Chemical investigation on a marine sponge, Dactylospongia elegans, yielded five new γ-oxygenated butenolide sesterterpene derivatives, dactylospenes A–E (1–5), as well as two known biosynthetically related compounds, luffariellolide (6) and furospinosulin B (7). The structures of these compounds were elucidated on the basis of their spectroscopic data, experimental and calculated electronic circular dichroism (ECD) analysis, as well as comparison of the NMR data with those of known analogs. These metabolites are the first γ-oxygenated butenolide sesterterpenes to be reported from this genus. These compounds were evaluated in antimicrobial, anti-inflammatory, and cytotoxic assays. Only compounds 1, 3, and 6 exhibited moderate cytotoxicity against DU145, SW1990, Huh7, and PANC-1 cancer cell lines with IC50 values in the range of 2.11–13.35 μM. Furthermore, compound 2, without cytotoxicity, exhibited significant inhibitory effects (inhibitory rate 77.5%) on nitric oxide production induced by lipopolysaccharide at 10 μM.
