Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium

Takahiro Nakazawa, Jingzhon Xu, Teruaki Nishikawa, Taiko Oda, Ayako Fujita, Kazuyo Ukai, Remy E.P. Mangindaan, Henki Rotinsulu, Hisayoshi Kobayashi, Michio Namikoshi

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Abstract

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-dimemoxy-6-(2′-N,N- dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5- (memylthio)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.

Original languageEnglish
Pages (from-to)439-442
Number of pages4
JournalJournal of Natural Products
Volume70
Issue number3
DOIs
Publication statusPublished - 2007 Mar 1

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Nakazawa, T., Xu, J., Nishikawa, T., Oda, T., Fujita, A., Ukai, K., Mangindaan, R. E. P., Rotinsulu, H., Kobayashi, H., & Namikoshi, M. (2007). Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium. Journal of Natural Products, 70(3), 439-442. https://doi.org/10.1021/np060593c