Renilla luciferin

Renilla luciferin and luciferyl sulfate. Luciferyl sulfate is extracted from the organisms with methanol. The extract is concentrated, defatted with benzene, and the aqueous layer is extracted with ethyl acetate. Luciferyl sulfate in the extract is purified by chromatography on a column of Sephadex LH-20 (Hori et al., 1972 Inoue et al., 1977a). Free luciferin is obtained by heating the sulfate in 0.1 N HC1 at 90° C for 50 sec, followed by extraction with ethyl acetate. The luciferin of Renilla thus obtained was found to be identical with coelenterazine (Inoue et al., 1977a Hori et al., 1977). 

The name of coelenterazine. We suggested calling the new luciferin coelenterazine (Shimomura and Johnson, 1975b), although Inoue et al. (1976) named it Watasenia preluciferin. The compound has been called by various other names, such as coelenterate luciferin, coelenterate-type luciferin, Oplopborus luciferin, and Renilla luciferin. However, these two-word chemical names are cumbersome to use and inconvenient when applying a chemical prefix or suffix. Currently, the name coelenterazine is widely and commonly used. 

Cormier, M. J., and Dure, L. S. (1963). Studies on the bioluminescence of Balanoglossus biminiensis extracts. I. Requirement for hydrogen peroxide and characteristics of the system. J. Biol. Chem. 238 785-789. Cormier, M. J., and Hori, K. (1963). Studies on the bioluminescence of Renilla reniformis. IV. Non-enzymatic activation of Renilla luciferin. Biochim. Biophys. Acta 88 99-104. 

DeLuca, M., Dempsey, M. E., Hori, K., and Cormier, M. J. (1976). Source of oxygen in CO2 produced during chemiluminescence of firefly luciferyl-adenylate and Renilla luciferin. Biochem. Biophys. Res. Commun. 69 262-267. 

Hori, K., Anderson, J. M., Ward, W. W., and Cormier, M. J. (1975). Renilla luciferin as the substrate for calcium induced photoprotein luminescence. Assignment of luciferin tautomers in aequorin and mnemiopsin. Biochemistry 14 2371-2376. 

Inoue, S., et al. (1977a). Complete structure of Renilla luciferin and luciferyl sulfate. Tetrahedron Lett., pp. 2685-2688. 

In the case of Vargula luciferin the expected incorporation of one atom of lsO into C02 was observed, but with firefly and Renilla luciferins no lsO entered the C02. In these two cases, a somewhat different mechanism may hold. 

Renilla luciferin was converted to luciferyl sulfate (204) by treatment of the diacetate (203) with sulfur trioxide in pyridine followed by removal of the acetyl group with ammonia (77TL2685). 

Renilla and Cypridina luciferases (E.C. 1.13.12.5 - Renilla luciferin oxygen 2-oxidoreductase (decarboxylating) and E.C.. Z. 2.6 Cypri-dina luciferin oxygen 2-oxidoreductase (decarboxylating). 

Inoue, S., H. Kakoi, M. Murata, T. Goto, and O. Shimomura Complete Structure of Renilla Luciferin and Luciferyl Sulfate. Tetrahedron Letts 1977, 2685. 

Fig. 15. Light emission from Renilla and Cypridina luciferin by the action of luciferases (Renilla luciferin 2-monooxygenase and Cypridina luciferin 2-monooxygenase)...

---