1. Densazalin, a New Cytotoxic Diazatricyclic Alkaloid from the Marine Sponge Haliclona densaspicula
- Author
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Sangbum Lee, Yong Tae Jeong, Buyng Su Hwang, Eun Ju Jeong, and Jung-Rae Rho
- Subjects
Stereochemistry ,Pharmaceutical Science ,Organic chemistry ,010402 general chemistry ,Mass spectrometry ,01 natural sciences ,Analytical Chemistry ,Haliclona densaspicula ,QD241-441 ,Haliclona ,Drug Discovery ,Bioassay ,Cytotoxic T cell ,Moiety ,Physical and Theoretical Chemistry ,densazalin ,Carbon chain ,biology ,010405 organic chemistry ,Chemistry ,Alkaloid ,biology.organism_classification ,0104 chemical sciences ,Sponge ,Chemistry (miscellaneous) ,cytotoxic alkaloid ,Molecular Medicine ,1,3-alkylpyridine - Abstract
Densazalin, a polycyclic alkaloid, was isolated from the marine sponge Haliclona densaspicula collected in Korea. The complete structure of the compound was determined by spectroscopic methods, including 1D and 2D nuclear magnetic resonance techniques, high-resolution mass spectrometry, and comparison of the calculated and measured electronic circular dichroism spectra. Densazalin possesses a unique 5,11-diazatricyclo[7.3.1.02,7]tridecan-2,4,6-triene moiety, which is connected by two linear carbon chains. This compound was derived from the biogenetic precursor bis-1,3-dialkylpyridnium. Densazalin exhibited cytotoxic activity on two human tumor cell lines (AGS and HepG2) in the Cell Counting Kit-8 (CCK-8) bioassay, with IC50 values ranging from 15.5 to 18.4 μM.
- Published
- 2021