Bioactive sulfated sesterterpene alkaloids and sesterterpene sulfates from the marine sponge Fasciospongia sp.
Two new sulfated sesterterpene alkaloids, 19-oxofasciospongine A (3) and fasciospongine C (4), and a new sesterterpene sulfate, 25-hydroxyhalisulfate 9 (5), along with two known sesterterpene sulfates, halisulfates 7 (6) and 9 (7), were isolated from an organic extract of the marine sponge Fasciospongia sp. The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopic studies as well as by HRESIMS analysis. Compounds 1-7 exhibited inhibitory activity against Streptomyces 85E in the hyphae-formation inhibition assay. Compounds 1, 2, and 4-7 were not cytotoxic when tested at 20 microg/mL with MCF-7, LNCaP, and LU cell lines. Only compound 3 demonstrated a moderate cytotoxic effect on the MCF-7 (IC(50) 13.4 microM), LNCaP (IC(50) 21.8 microM), and LU-1 cells (IC(50) 5.0 microM), respectively.
Yao
Guangmin
G
Department of Chemistry and Biochemistry, College of Science and Engineering, University of Minnesota Duluth, 1039 University Drive, Duluth, Minnesota 55812, USA.
Kondratyuk
Tamara P
TP
Tan
Ghee T
GT
Pezzuto
John M
JM
Chang
Leng Chee
LC
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D054830:Sesterterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013302:Streptomyces / Q000187:drug effects; D013463:Sulfuric Acid Esters / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
C550407:19-oxofasciospongine A; C550406:25-hydroxyhalisulfate 9; D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D054830:Sesterterpenes; D013463:Sulfuric Acid Esters; C550408:fasciospongine C