Bisindole alkaloids of the topsentin and hamacanthin classes from a marine sponge Spongosorites sp.
Seven new (1 and 3-8) and seven known (2 and 9-14) bisindole alkaloids of the topsentin and hamacanthin classes were isolated from the MeOH extract of a marine sponge Spongosorites sp. by bioactivity-guided fractionation. The structure of compound 7 is a revision from our previous report. The planar structures were established on the basis of NMR and MS spectroscopic analyses. Configurations of these compounds were defined by NMR spectroscopy and optical rotation. It is noteworthy that both R and S isomers were isolated for the hamacanthins (1-4, 9, 10, 15, and 16), while a single stereoisomer was isolated for dihydrohamacanthins (5, 11-14, 17, and 18). Compounds 1-4, 6, and 8-14 showed marginal cytotoxicity against five human solid tumor cell lines, and compound 2 showed weak antibacterial activity against clinically isolated methicillin-resistant strains.
Bao
Baoquan
B
College of Pharmacy, Pusan National University, Busan 609-735, Korea.
Sun
Qishi
Q
Yao
Xinsheng
X
Hong
Jongki
J
Lee
Chong-O
CO
Cho
Hee Young
HY
Jung
Jee H
JH
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007093:Imidazoles / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology; D007723:Korea; D008386:Marine Biology; D016106:Methicillin Resistance / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011719:Pyrazines / Q000737:chemistry / Q000145:classification / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D007093:Imidazoles; D026121:Indole Alkaloids; D007211:Indoles; D011719:Pyrazines; C070184:topsentin; C091314:hamacanthine B