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.

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