4.7 Article

Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 17, 页码 9592-9603

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00310

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  1. Ministry of Education, Culture, Sports, Science and Technology of Japan [16H03285, 15K01803, 15H06584]
  2. Keio Leading-Edge Laboratory of Science, and Technology (KLL)Specified Research Projects

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Two new jahanyne analogues, jahanene and jahanane, highly N-methylated lipopeptides, were isolated from a marine cyanobacterium Okeania sp., and their structures were determined by NMR and MS. In addition, we achieved total syntheses of the jahanyne family and assessed their activities. The resulting growth-inhibitory activity of jahanyne was nearly one-tenth of the previously reported activity. Furthermore, we found that the degree of unsaturation at the terminus of the fatty acid moiety affected the growth-inhibitory activity against human cancer cells.

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