Tridentatols D-H, nematocyst metabolites and precursors of the activated chemical defense in the marine hydroid Tridentata marginata (Kirchenpauer 1864).
The marine hydroid Tridentata marginata (Kirchenpauer 1864) produces tridentatols A-C (1-3), of which 1 is a potent deterrent to fish predation. This paper reports the structures of five additional secondary metabolites, tridentatols D-H (4-8), that have been isolated from this hydroid. When hydroid tissue is crushed, as attacking predators would do, tridentatols E-H (5-8), which do not deter fish feeding, are rapidly converted to tridentatols A-D (1-4), thereby repelling potential predators. Additionally, the tridentatols were isolated from this hydroid's nematocysts (i.e., stinging organelles), representing the first report of a nonprotein venom produced by cnidarian nematocysts. The structures of 4-8 were determined by interpretation of their spectral data.
Lindquist
Niels
N
University of North Carolina at Chapel Hill, Marine Sciences Program, Institute of Marine Sciences, Morehead City, North Carolina 28557, USA. nlindquist@unc.edu.us
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003063:Cnidaria; D003064:Cnidarian Venoms / Q000737:chemistry* / Q000378:metabolism; D005247:Feeding Behavior / Q000187:drug effects; D005399:Fishes / Q000502:physiology; D008386:Marine Biology; D015394:Molecular Structure; D009657:North Carolina; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017550:Spectroscopy, Fourier Transform Infrared
D003064:Cnidarian Venoms; D010636:Phenols; C121186:tridentatol A