Callyazepin and (3R)-Methylazacyclodecane, Nitrogenous Macrocycles from a Callyspongia sp. Sponge

  • J Nat Prod. 2016 Apr 22;79(4):1179-83. doi: 10.1021/acs.jnatprod.5b01078.
Chang-Kwon Kim  1 ,  Jung-Kyun Woo  1 ,  Yeon-Ju Lee  2 ,  Hyi-Seung Lee  2 ,  Chung J Sim  3 ,  Dong-Chan Oh  1 ,  Ki-Bong Oh  4 ,  Jongheon Shin  1
Affiliations
  • 1. Natural Products Research Institute, College of Pharmacy, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-742, Korea.
  • 2. Marine Natural Products Laboratory, Korea Institute of Ocean Science & Technology , P.O. Box 29, Seoul 425-600, Korea.
  • 3. Department of Biological Science, College of Life Science and Nano Technology, Hannam University , 461-6 Jeonmin, Yuseong, Daejeon 305-811, Korea.
  • 4. Department of Agricultural Biotechnology, College of Agriculture & Life Science, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-921, Korea.
PMID: 27015002 DOI: 10.1021/acs.jnatprod.5b01078
Abstract

Callyazepin (1) and (3R)-methylazacyclodecane (2), nitrogenous macrocycles, were isolated from a tropical Callyspongia sp. Sponge. The combined spectroscopic analyses revealed that the structure of 1 is a bicyclic azepane ammonium salt of a novel structural class derived from mixed biogenetic origins. The configuration of the whole molecule and the conformation of the formamide group were assigned by proton-proton coupling constants, a NOESY analysis, and the application of the phenylglycine methyl ester method. The structure of 2 was identified using combined spectroscopic analyses and ECD measurements. These compounds exhibited moderate cytotoxic activities against the K562 and A549 cell lines.