期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 12, 页码 5135-5143出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00695
关键词
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资金
- EU [311848, 246987]
- National Natural Science Fund of China [81225023, 41576130, 41428602, 81402844, 81373321, 81302691, 41476121]
- Shanghai Rising-Star program [14QA1402800]
- National High Technology Research and Development Program of China (863 Project) [2013AA092902]
- USDA-ARS [586408-1-603]
Fifteen polyketides, including the first hydroxylated plakortone (12) and plakdiepoxide (15), the first polyketide to embed a vicinal diepoxide, have been isolated from the Chinese sponge Plakortis simplex. The structures of the new metabolites were elucidated by analysis of spectroscopic data, Mosher's derivatization, and DFT computational calculations. The reactivity of the major endoperoxide of this sponge was investigated, suggesting that furan, furylidene, and plakilactone derivatives, well-known classes of natural products, could actually be chemical degradation products. Plakdiepoxide is a potent and selective modulator of peroxisome proliferator-activated receptor (PPAR)-gamma, while the diunsaturated C-12 fatty acid monotriajaponide (13) activates both PPAR-alpha and PPAR-gamma, a dual activity of potential great importance for the treatment of metabolic disorders.
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