Cytotoxic scalarane sesterterpenoids from the South China Sea sponge Carteriospongia foliascens.
Eleven new scalarane sesterterpenoids, including three 20,24-bishomo-25-norscalaranes, carteriofenones A–C (1–3), and eight 20,24-bishomoscalaranes, carteriofenones D–K (4–11), along with two known analogues (12 and 13), were obtained from the marine sponge Carteriospongia foliascens collected from the South China Sea. Their planar structures and relative configurations were elucidated by extensive NMR spectroscopic data. The absolute configuration of 3 was determined using the modified Mosher's method on its hydrolysis product. Scalarane sesterterpenoids with 4-methylpentanate or pentanoate substituents at the 12-position (1–8) were reported for the first time. Carteriofenones E–H (5–8) represented rare naturally occurring scalarane sesterterpenoids with a cyclobutane ring. Compound 4 showed cytotoxicity against the mouse lymphocytic leukemia cell line (P388) with an IC50 value of 0.96 μM.
Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China. changyun@ouc.edu.cn.
Fei
F
Cao
Ze-Hong
ZH
Wu
Chang-Lun
CL
Shao
Sen
S
Pang
Xiao-Yan
XY
Liang
Nicole J
NJ
de Voogd
Chang-Yun
CY
Wang
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D020128:Inhibitory Concentration 50; D051379:Mice; D011161:Porifera / Q000737:chemistry*; D054830:Sesterterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D054830:Sesterterpenes