Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium.
Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2'-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5-(methylthio)varacin (11). Compounds 1-11 were isolated from the ascidian collected in March (wet season), while 5-11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4-7 (1-4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 microM, respectively. Compounds 1-4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.
Nakazawa
Takahiro
T
Tohoku Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan.
Xu
Jingzhon
J
Nishikawa
Teruaki
T
Oda
Taiko
T
Fujita
Ayako
A
Ukai
Kazuyo
K
Mangindaan
Remy E P
RE
Rotinsulu
Henki
H
Kobayashi
Hisayoshi
H
Namikoshi
Michio
M
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D006224:Cricetinae; D003412:Cricetulus; D004926:Escherichia coli / Q000187:drug effects; D007214:Indonesia; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013455:Sulfur / Q000737:chemistry / Q000494:pharmacology; D014561:Urochordata / Q000737:chemistry*
D000470:Alkaloids; D013455:Sulfur