TY - JOUR
T1 - Two unprecedented cembrene-type terpenes from an indonesian soft coral sarcophyton sp.
AU - Kapojos, Magie M.
AU - Lee, Jong Soo
AU - Oda, Taiko
AU - Nakazawa, Takahiro
AU - Takahashi, Ohgi
AU - Ukai, Kazuyo
AU - Mangindaan, Remy E.P.
AU - Rotinsulu, Henki
AU - Wewengkang, Defny S.
AU - Tsukamoto, Sachiko
AU - Kobayashi, Hisayoshi
AU - Namikoshi, Michio
N1 - Funding Information:
This work was supported in part by Grant-in-Aid for Scientific Research (No. 18032033) and for Scientific Research on Priority Areas (No. 17035029) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan. We thank Ms. D.A. Sumilat of Sam Ratulangi University for identification of the soft coral. J.-S.L. is grateful to the Japan Society for the Promotion of Science (JSPS) for financial support to study in Japan (The Invitation Fellowship for Research in Japan, Long-Term).
PY - 2010/1/16
Y1 - 2010/1/16
N2 - 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.
AB - 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.
KW - Cembrene
KW - Furanocembrenolide
KW - RAW264.7 cell
KW - Structure assignment
KW - TNF-α
KW - V79 cell
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U2 - 10.1016/j.tet.2009.11.078
DO - 10.1016/j.tet.2009.11.078
M3 - Article
AN - SCOPUS:71949105697
SN - 0040-4020
VL - 66
SP - 641
EP - 645
JO - Tetrahedron
JF - Tetrahedron
IS - 3
ER -