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

2018; American Chemical Society; Volume: 83; Issue: 17 Linguagem: Inglês

10.1021/acs.joc.8b00310

1520-6904

Arihiro Iwasaki, Haruka Fujimura, Shinichiro Okamoto, Takafumi Kudo, Shizuka Hoshina, Shimpei Sumimoto, Toshiaki Teruya, Kiyotake Suenaga,

Algal biology and biofuel production

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.