title: Callyazepin and (3R)-Methylazacyclodecane, Nitrogenous Macrocycles from a Callyspongia sp. Sponge.
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.
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-742, Korea.
authors.forename: Chang-Kwon
authors.initials: CK
authors.lastname: Kim
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-742, Korea.
authors.forename: Jung-Kyun
authors.initials: JK
authors.lastname: Woo
authors.affiliation: Marine Natural Products Laboratory, Korea Institute of Ocean Science & Technology , P.O. Box 29, Seoul 425-600, Korea.
authors.forename: Yeon-Ju
authors.initials: YJ
authors.lastname: Lee
authors.affiliation: Marine Natural Products Laboratory, Korea Institute of Ocean Science & Technology , P.O. Box 29, Seoul 425-600, Korea.
authors.forename: Hyi-Seung
authors.initials: HS
authors.lastname: Lee
authors.affiliation: Department of Biological Science, College of Life Science and Nano Technology, Hannam University , 461-6 Jeonmin, Yuseong, Daejeon 305-811, Korea.
authors.forename: Chung J
authors.initials: CJ
authors.lastname: Sim
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-742, Korea.
authors.forename: Dong-Chan
authors.initials: DC
authors.lastname: Oh
authors.affiliation: Department of Agricultural Biotechnology, College of Agriculture & Life Science, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-921, Korea.
authors.forename: Ki-Bong
authors.initials: KB
authors.lastname: Oh
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University , San 56-1, Sillim, Gwanak, Seoul 151-742, Korea.
authors.forename: Jongheon
authors.initials: J
authors.lastname: Shin
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047128:Callyspongia / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020014:K562 Cells; D047028:Macrocyclic Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008849:Micronesia; D008968:Molecular Conformation; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas
chemical_list: C000610618:(3R)-methylazacyclodecane; D000970:Antineoplastic Agents; D047028:Macrocyclic Compounds; C000610617:callyazepin; D009584:Nitrogen