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

Fingerprint

Urochordata
Alkaloids
Dopamine
Leukemia L1210
Indonesia
Cell proliferation
Sulfides
Cricetulus
Disulfides
Dimers
Monomers
Cell Proliferation

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Wang, W., Takahashi, O., Oda, T., Nakazawa, T., Ukai, K., Mangindaan, R. E. P., ... 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

Lissoclibadins 8-14, polysulfur dopamine-derived alkaloids from the colonial ascidian Lissoclinum cf. badium. / Wang, Weifang; Takahashi, Ohgi; Oda, Taiko; Nakazawa, Takahiro; Ukai, Kazuyo; Mangindaan, Remy E P; Rotinsulu, Henki; Wewengkang, Defny S.; Kobayashi, Hisayoshi; Tsukamoto, Sachiko; Namikoshi, Michio.

In: Tetrahedron, Vol. 65, No. 46, 14.11.2009, p. 9598-9603.

Research output: Contribution to journalArticle

Wang, W, Takahashi, O, Oda, T, Nakazawa, T, Ukai, K, Mangindaan, REP, Rotinsulu, H, Wewengkang, DS, Kobayashi, H, Tsukamoto, S & Namikoshi, M 2009, 'Lissoclibadins 8-14, polysulfur dopamine-derived alkaloids from the colonial ascidian Lissoclinum cf. badium', Tetrahedron, vol. 65, no. 46, pp. 9598-9603. https://doi.org/10.1016/j.tet.2009.09.056
Wang, Weifang ; Takahashi, Ohgi ; Oda, Taiko ; Nakazawa, Takahiro ; Ukai, Kazuyo ; Mangindaan, Remy E P ; Rotinsulu, Henki ; Wewengkang, Defny S. ; Kobayashi, Hisayoshi ; Tsukamoto, Sachiko ; Namikoshi, Michio. / Lissoclibadins 8-14, polysulfur dopamine-derived alkaloids from the colonial ascidian Lissoclinum cf. badium. In: Tetrahedron. 2009 ; Vol. 65, No. 46. pp. 9598-9603.
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