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...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2007-03, Vol.70 (3), p.439-442
Main Authors: Nakazawa, Takahiro, Xu, Jingzhon, Nishikawa, Teruaki, Oda, Taiko, Fujita, Ayako, Ukai, Kazuyo, Mangindaan, Remy E. P, Rotinsulu, Henki, Kobayashi, Hisayoshi, Namikoshi, Michio
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Animals
Biological and medical sciences
Cricetinae
Cricetulus
Escherichia coli
Escherichia coli - drug effects
General pharmacology
Indonesia
Lissoclinum
Medical sciences
Microbial Sensitivity Tests
Molecular Structure
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Saccharomyces cerevisiae
Saccharomyces cerevisiae - drug effects
Staphylococcus aureus
Staphylococcus aureus - drug effects
Sulfur - chemistry
Sulfur - pharmacology
Urochordata - chemistry
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Summary: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 μM, respectively. Compounds 1−4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.
ISSN:0163-3864
1520-6025
DOI:10.1021/np060593c