Two unprecedented cembrene-type terpenes from an indonesian soft coral sarcophyton sp.

Magie M. Kapojos, Jong Soo Lee, Taiko Oda, Takahiro Nakazawa, Ohgi Takahashi, Kazuyo Ukai, Remy E.P. Mangindaan, Henki Rotinsulu, Defny S. Wewengkang, Sachiko Tsukamoto, Hisayoshi Kobayashi, Michio Namikoshi

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20 Citations (Scopus)

Abstract

Two unusual cembranoids, sarcofuranocembrenolides A (1) and B (2), were isolated from a soft coral Sarcophyton sp. together with five known cembranoids (3-7). Compound 1 had a unique carbon skeleton of 8,19-bisnorfuranocembrenolide. Compound 2 was a furanocembrenolide, but a C1 unit (C-20) was attached to C-10 instead of C-12 of the ordinary cembrenolides. These rearrangements are unique in the biosynthesis of cembranoid diterpenes. Lobohedleolide (5), (7Z)-lobohedleolide (6), and denticulatolide (7) inhibited the colony formation of V79 cells at ED50 values of 4.6 (abt. 1.52), 3.7 (1.22), and 3.6 (1.40) μM (μg/mL), respectively, and reduced TNF-α production from LPS-stimulated RAW264.7 cells at 3.0-10.0 μM.

Original languageEnglish
Pages (from-to)641-645
Number of pages5
JournalTetrahedron
Volume66
Issue number3
DOIs
Publication statusPublished - 2010 Jan 16

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Keywords

  • Cembrene
  • Furanocembrenolide
  • RAW264.7 cell
  • Structure assignment
  • TNF-α
  • V79 cell

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Kapojos, M. M., Lee, J. S., Oda, T., Nakazawa, T., Takahashi, O., Ukai, K., Mangindaan, R. E. P., Rotinsulu, H., Wewengkang, D. S., Tsukamoto, S., Kobayashi, H., & Namikoshi, M. (2010). Two unprecedented cembrene-type terpenes from an indonesian soft coral sarcophyton sp. Tetrahedron, 66(3), 641-645. https://doi.org/10.1016/j.tet.2009.11.078