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

Research output: Contribution to journalArticle

67 Citations (Scopus)

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

Fingerprint

Urochordata
Ascidiacea
Alkaloids
aromatic compounds
alkaloids
Indonesia
Chinese hamsters
Cricetulus
Yeast
Escherichia coli
Saccharomyces cerevisiae
Staphylococcus aureus
dry season
wet season
anti-infective agents
organisms
cells

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Nakazawa, T., Xu, J., Nishikawa, T., Oda, T., Fujita, A., Ukai, K., ... 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

Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium. / Nakazawa, Takahiro; Xu, Jingzhon; Nishikawa, Teruaki; Oda, Taiko; Fujita, Ayako; Ukai, Kazuyo; Mangindaan, Remy E P; Rotinsulu, Henki; Kobayashi, Hisayoshi; Namikoshi, Michio.

In: Journal of Natural Products, Vol. 70, No. 3, 03.2007, p. 439-442.

Research output: Contribution to journalArticle

Nakazawa, T, Xu, J, Nishikawa, T, Oda, T, Fujita, A, Ukai, K, Mangindaan, REP, Rotinsulu, H, Kobayashi, H & Namikoshi, M 2007, 'Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium', Journal of Natural Products, vol. 70, no. 3, pp. 439-442. https://doi.org/10.1021/np060593c
Nakazawa, Takahiro ; Xu, Jingzhon ; Nishikawa, Teruaki ; Oda, Taiko ; Fujita, Ayako ; Ukai, Kazuyo ; Mangindaan, Remy E P ; Rotinsulu, Henki ; Kobayashi, Hisayoshi ; Namikoshi, Michio. / Lissoclibadins 4-7, polysulfur aromatic alkaloids from the Indonesian ascidian Lissoclinum cf. badium. In: Journal of Natural Products. 2007 ; Vol. 70, No. 3. pp. 439-442.
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