Justin Reinicke, Ryuju Kitatani, Shadi Sedghi Masoud, Kelly Kawabata Galbraith, Wesley Yoshida, Ayako Igarashi, Kazuo Nagasawa, Gideon Berger, Angel Yanagihara, Hiroshi Nagai, F David Horgen
Cubozoan nematocyst venoms contain known cytolytic and hemolytic proteins, but small molecule components have not been previously reported from cubozoan venom. We screened nematocyst extracts of Alatina alata and Chironex yamaguchii by LC-MS for the presence of small molecule metabolites. Three isomeric compounds, cnidarins 4A ( 1 ), 4B ( 2 ), and 4C ( 3 ), were isolated from venom extracts and characterized by NMR and MS, which revealed their planar structure as cyclic γ-linked tetraglutamic acids. The full configurational assignments were established by syntheses of all six possible stereoisomers, comparison of spectral data and optical rotations, and stereochemical analysis of derivatized degradation products...
February 17, 2020: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry