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

J Org Chem. 2018 Sep 7;83(17):9592-9603. doi: 10.1021/acs.joc.8b00310. Epub 2018 Aug 23.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Chemistry Techniques, Synthetic
  • Cyanobacteria / chemistry
  • Fatty Acids / chemistry
  • HeLa Cells
  • Humans
  • Lipopeptides / chemical synthesis*
  • Lipopeptides / chemistry
  • Lipopeptides / isolation & purification*
  • Lipopeptides / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Fatty Acids
  • Lipopeptides
  • jahanyne