Spongiapyridine and Related Spongians Isolated from an Indonesian Spongia sp.

详细信息    查看全文

• 作者：Stephen M. Parrish ; Wesley Y. Yoshida ; Tamara P. Kondratyuk ; Eun-Jung Park ; John M. Pezzuto ; Michelle Kelly ; Philip G. Williams
• 刊名：Journal of Natural Products
• 出版年：2014
• 出版时间：July 25, 2014
• 年：2014
• 卷：77
• 期：7
• 页码：1644-1649
• 全文大小：252K
• ISSN：1520-6025

文摘

New compounds 18-nor-3,17-dihydroxyspongia-3,13(16),14-trien-2-one (1), 18-nor-3,5,17-trihydroxyspongia-3,13(16),14-trien-2-one (2), and spongiapyridine (3) and the known compound 17-hydroxy-4-epi-spongialactone A (4) were isolated from an Indonesian sponge of the genus Spongia. The structures of 1鈥?b>3 were deduced by analyses of physical and spectroscopic data. Diterpene 3 is unusual, as the D-ring is a pyridyl ring system rather than the standard 未-lactone. The structure elucidation of this compound was complicated by facile exchange of the axial proton at the C-11 methylene with deuterium from methanol-d₄. The isolated compounds were tested for biological activity in a battery of in vitro assays (TNF-伪-induced NF魏B, LPS-induced iNOS, RXR stimulation, quinone reductase 1 induction, aromatase inhibition, TRPM7 ion channels, and aspartic protease BACE1 inhibition). Norditerpene 2 modestly inhibited aromatase with an IC₅₀ of 34 渭M and induced quinone reductase 1 activity with a CD (the concentration needed to double the enzymatic response) of 11.2 渭M. The remaining isolates were inactive.