Lissoclibadins 8-14, polysulfur dopamine-derived alkaloids from the colonial ascidian Lissoclinum cf. badium

Weifang Wang, Ohgi Takahashi, Taiko Oda, Takahiro Nakazawa, Kazuyo Ukai, Remy E.P. Mangindaan, Henki Rotinsulu, Defny S. Wewengkang, Hisayoshi Kobayashi, Sachiko Tsukamoto, Michio Namikoshi

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Seven new polysulfur alkaloids, lissoclibadins 8 (1)-14 (7), were isolated from an ascidian, Lissoclinum cf. badium, collected in Indonesia. The structures were assigned on the basis of their spectroscopic data and computational modeling study. Lissoclibadin 8 (1) had four identical dopamine-derived units, and this is the first instance of a tetramer. Lissoclibadin 9 (2) was the second example of trimers next to lissoclibadin 1 (8). Lissoclibadins 10 (3)-12 (5) were symmetric dimers, and 13 (6) had a dopamine and ethyl units connected by sulfide and disulfide bonds. Lissoclibadin 14 (7) was a varacin-type monomer. These compounds inhibited the colony formation of Chinese hamster V79 cells and cell proliferation of murine leukemia L1210 cells.

Original languageEnglish
Pages (from-to)9598-9603
Number of pages6
JournalTetrahedron
Volume65
Issue number46
DOIs
Publication statusPublished - 2009 Nov 14

Keywords

  • Cytotoxicity
  • L1210
  • Polysulfur alkaloid
  • Structure assignment
  • Tunicate
  • V79

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Wang, W., Takahashi, O., Oda, T., Nakazawa, T., Ukai, K., Mangindaan, R. E. P., Rotinsulu, H., Wewengkang, D. S., Kobayashi, H., Tsukamoto, S., & Namikoshi, M. (2009). Lissoclibadins 8-14, polysulfur dopamine-derived alkaloids from the colonial ascidian Lissoclinum cf. badium. Tetrahedron, 65(46), 9598-9603. https://doi.org/10.1016/j.tet.2009.09.056