Characterization of an anthraquinone fluor from the bioluminescent, pelagic polychaete Tomopteris.
Tomopteris is a cosmopolitan genus of polychaetes. Many species produce yellow luminescence in the parapodia when stimulated. Yellow bioluminescence is rare in the ocean, and the components of this luminescent reaction have not been identified. Only a brief description, half a century ago, noted fluorescence in the parapodia with a remarkably similar spectrum to the bioluminescence, which suggested that it may be the luciferin or terminal light-emitter. Here, we report the isolation of the fluorescent yellow-orange pigment found in the luminous exudate and in the body of the animals. Liquid chromatography-mass spectrometry revealed the mass to be 270 m/z with a molecular formula of C(15)H(10)O(5), which ultimately was shown to be aloe-emodin, an anthraquinone previously found in plants. We speculate that aloe-emodin could be a factor for resonant-energy transfer or the oxyluciferin for Tomopteris bioluminescence.
Monterey Bay Aquarium Research Institute, Moss Landing, CA, 95039, USA; Department of Ocean Sciences, University of California Santa Cruz, Santa Cruz, CA, USA.
Warren R
WR
Francis
Meghan L
ML
Powers
Steven H D
SH
Haddock
D000818:Animals; D000880:Anthraquinones / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D007211:Indoles / Q000737:chemistry; D049449:Luminescence; D013058:Mass Spectrometry; D015394:Molecular Structure; D010860:Pigments, Biological / Q000737:chemistry; D011077:Polychaeta / Q000737:chemistry* / Q000502:physiology; D011719:Pyrazines / Q000737:chemistry
D000880:Anthraquinones; D007211:Indoles; D010860:Pigments, Biological; D011719:Pyrazines; C014730:oxyluciferin; C518327:aloe emodin
Tomopteris; anthraquinone; bioluminescence; fluorescence; polychaete