Squid, bioluminescent

Inoue, S., Sugiura, S., Kakoi, H., and Hashizume, K. (1975). Squid bioluminescence. II. Isolation from Watasenia scintillans and synthesis of 2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-3,7-dihydroimidazo[l, 2-a]pyrazin-3-one. Chem. Lett., pp. 141-144. 

Inoue, S., et al. (1977b). Squid bioluminescence IV. Isolation and structural elucidation of Watasenia dehydropreluciferin. Chem. Lett., pp. 259-262. 

Isobe M, Kuse M, Yasuda Y, Takahashi H. Synthesis of C-Dehydrocoelenterazine and model studies on Symplectoteuthis squid bioluminescence. BioMed Chem Lett 1998 8 2919-24. 

Goto T, lio H, Inoue S, Kakoi H. Squid bioluminescence. I. Stmcture of Watasenia oxyluciferin, a possible light-emitter in the bioluminescence of Watasenia scintillans. Tetrahedron Lett 1974 2321-4. 

Inoue S, Kakoi H, Goto T. Squid bioluminescence. III. Isolation and structure of Watasenia luciferin. Tetrahedron Lett 1976 2971-4. 

Bioluminescence functions in mating (fireflies, the Bahama fireworm), in the search for prey (angler fish, Photmus fireflies), camouflage (hatchet fish, squid), schooling (euphausiid shrimp), and to aid deep water fish (flashlight fish, Photoblepharon to see in the dark ocean depths. 

Soon after the hypothetical structure was published, coelenterazine was isolated as an actual substance from the liver of the luminous squid Watasenia scintillans, and it was chemically synthesized (Inoue et al., 1975). The availability of synthetic coelenterazine led to the important discovery that the treatment of the luminescence product of aequorin with coelenterazine results in the regeneration of active aequorin (Shimomura and Johnson, 1975c), which consequently confirmed the presence of a coelenterazine moiety in the aequorin molecule. During the same period, it became increasingly evident that coelenterazine is involved as a luciferin in various bioluminescent organisms, such as the sea cactus Cavernularia, the sea pen Ptilosarcus, and the sea pansy Renilla (Shimomura and Johnson, 1975b). 

The enol-sulfate form (I), which is the precursor of the luciferin in the bioluminescence system of the sea pansy Renilla (Hori et al., 1972), can be readily converted into coelenterazine by acid hydrolysis. The enol-sulfate (I), dehydrocoeienterazine (D) and the coelenterazine bound by the coelenterazine-binding proteins are important storage forms for preserving unstable coelenterazine in the bodies of luminous organisms. The disulfate form of coelenterazine (not shown in Fig. 5.5) is the luciferin in the firefly squid Watasenia (Section 6.3.1). An enol-ether form of coelenterazine bound with glucopyra-nosiduronic acid has been found in the liver of the myctophid fish Diapbus elucens (Inoue et al., 1987). 

In Mollusca, bioluminescence occurs in a great variety of organisms having distinctly different appearances, such as the classes Gastropoda (limpets, snails and sea hares), Bivalvia (clams), and Cephalopoda (squids and octopuses). All luminous molluscs currently known are marine organisms, except the New Zealand fresh water limpet Latia neritoides and the Malaysian land snail Quantula (Dyakia) striata. No information is yet available on the biochemical aspects of the Quantula luminescence. 

There are many kinds of bioluminescent squids. Some of them harbor luminous bacteria for their light emission (Harvey, 1952 Haneda, 1985), but all other luminous squids currently known utilize coelenterazine or its derivatives in their bioluminescence systems, and... 

Matsui, S., et al. (1988). 4-Hydroxyretinal, a new pigment chromophore found in the bioluminescent squid, Watasenia scintillans. Biochim. Bio-phys. Acta 966 370-374. 

Takahashi, H., and Isobe, M. (1993). Symplectoteuthis bioluminescence. (1). Structure and binding form of chromophore in photoprotein of a luminous squid. Bioorg. Med. Chem. Lett. 3 2647-2652. 

Takahashi, H., Yasuda, Y., and Isobe, M. (1994). Bioluminescence mechanism on Okinawan squid. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 36th, pp. 144-151. 

Tsuji, F. I. (1985). ATP-dependent bioluminescence in the firefly squid, Watasenia scintillans. Proc. Natl. Acad. Sci. USA 82 4629-4632. 

Tsuji, F. I. (2002). Bioluminescence reaction catalyzed by membrane-bound luciferase in the firefly squid Watasenia scintillans. Biochim. Biophys. Acta 1564 189-197. 

Tsuji, F. I., and Leisman, G. (1982). Membrane-bound bioluminescence in the pelagic squid. Symplectoteutbis oualaniensis. In Hastings, J. W., and Gitelzon, I. I. (eds.), Biolyumin. Tikhon Okeane. Mater. Simp. Tikhookean. Nauchn. Kongr. 14th, 1979, pp. 127-135. Akad. Nauk SSSR, Sib. Otd., Inst. Fiz. Krasnoyarsk, USSR. 

Bioluminescence is the production of light by living systems. The best-known example of this phenomenon is the characteristic glow of the firefly, but other luminous species include bacteria, fungi and other animals such as jellyfish, scale-worms, deep-sea squid, prawn and fish. In animals bioluminescence is used as a diversionary tactic when disturbed, to attract prey and of course as a mating signal during courtship. 

Animals use bioluminescence for several different reasons. The bioluminescent squid, for example, uses bioluminescence to get away from predators. The squid squirts out a big cloud of glowing chemicals and escapes from danger while the predator is distracted. Tiny, shrimp-like animals called krill also use their light power to try to avoid being eaten. For krill, there is safety in... 

Boettcher, K.J., Ruby, E.G., and McFall-Ngai, M.J., Bioluminescence in the symbiotic squid Euprymna scolopes is controlled by a daily biological rhythm, J. Comp. Physiol, 179, 65, 1996. 

R653 M. Isobe, M. Kuse, T. Fujii, H. Takahashi, K. Ohshima, H. Mori, J.-Y. Ahn and M. Tsukasa, Molecular Mechanisms of Bioluminescence of Symplectin, a Photoprotein from Okinawan Squid, Symplectoteuthis Oualaniensis L , Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 2000, 42, 97... 

Tsuji FI, Leisman G. K /Na -triggered bioluminescence in the oceanic squid Symplectoteuthis oualaniensis. Proc Natl Acad Sci USA 1981 78 6719-23. 

---