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Two unprecedented cembrene-type terpenes from an indonesian soft coral sarcophyton sp. |
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| Authors: | Magie M Kapojos Taiko Oda Ohgi Takahashi Remy EP Mangindaan Defny S Wewengkang Sachiko Tsukamoto Michio Namikoshi |
| Institution: | a Department of Natural Product Chemistry, Tohoku Pharmaceutical University, Aoba-ku, Sendai 981-8558, Japan b Faculty of Pharmaceutical Sciences, Keio University, Minato-ku, Tokyo 105-8512, Japan c Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia d Faculty of Medical and Pharmaceutical Sciences, Kumamoto University, Oe-honmachi, Kumamoto 862-0973, Japan e Institute of Molecular and Cellular Biosciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-0032, Japan |
| 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. |
| Keywords: | Furanocembrenolide Cembrene Structure assignment V79 cell RAW264 7 cell TNF-α |
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