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Molecular structure of the luciferins identified in marine and terrestrial bioluminescent organisms. Modified from Kaskova et al. (2016). 

Molecular structure of the luciferins identified in marine and terrestrial bioluminescent organisms. Modified from Kaskova et al. (2016). 

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ABSTRACT Bioluminescence - visible and cold light emission by living organisms - is a worldwide phenomenon, reported in terrestrial and marine environments since ancient times. Light emission from microorganisms, fungi, plants and animals may have arisen as an evolutionary response against oxygen toxicity and was appropriated for sexual attraction,...

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... is believed that the acquisition of bioluminescence occurred discontinuously at least 30 times along the evolution, on the basis of the varied luciferase structures, enzymatic mechanisms and luciferin nature clarified until now in distant luminous organisms. Kaskova et al. (2016) listed nine luciferins identified up to the present: FMNH/ long chain aldehyde in bacteria (Aliivibrio fisheri), linear tetrapyrrole in dinoflagellates (Lingulodinium polyedra, formely Goniaulax), hispidin in fungi, an aliphatic formylenol in a clam (Latia luciferin), two imidazopyrazines in crustaceans (Vargula, formerly Cypridina luciferin) and coelenterates (Renilla and Aequorea luciferin), a N-isovaleryl- 3-aminopropanal in the earthworm Diplocardia, a peptide in another earthworm (Fridericia), and a benzothiazolyl thiazole in coleopterans (Fig. 2). Luciferins of the blue-emitting flies Arachnocampa (New Zealand) and Orphelia (United States of America) are still under investigation ( Viviani et al. ...
Context 2
... first acts as a ligase at costs of ATP to activate the luciferin carboxylic group as a luciferyl-adenylate anhydride (Fig. 3, 1) and sequentially as an oxygenase by inserting molecular oxygen into the luciferin α-carbanion to form an α-hydroperoxide ( Fig. 3, 2). This intermediate then undergoes cyclization with release of AMP to a putative four-membered ring peroxide (Fig.3, 3), named α-peroxylactone or dioxetanone ( Bartoloni et al. 2015, Bastos et al. 2017), whose cleavage (Fig. 3, 7) yields CO 2 and the oxyluciferin in the excited singlet, fluorescent state (Fig. 3, 4-6) (Shimomura et al. 1977, Oba et al. 2003). The topology of the luciferase active site is importantly affected by (i) the pH in lampyrid luciferases, but not in elaterids and phengodids (Viviani and Bechara 1995); (ii) the polarity of the microenvironment; and (iii) the luciferin binding and catalytic amino acids which may favor formation of the excited oxyluciferin either in its red (λ max ~ 615 nm) monoanion keto form (Fig. 3, 4) and green (540 nm) dianion enolate form (Fig. 3, 5) (Shimomura 2012, Viviani et al. 2012). These facts led to the belief that an important basic amino acid residue like arginine present, distant or absent near the nascent excited oxyluciferin assists the formation of the keto or enolate ...
Context 3
... is believed that the acquisition of bioluminescence occurred discontinuously at least 30 times along the evolution, on the basis of the varied luciferase structures, enzymatic mechanisms and luciferin nature clarified until now in distant luminous organisms. Kaskova et al. (2016) listed nine luciferins identified up to the present: FMNH/ long chain aldehyde in bacteria (Aliivibrio fisheri), linear tetrapyrrole in dinoflagellates (Lingulodinium polyedra, formely Goniaulax), hispidin in fungi, an aliphatic formylenol in a clam (Latia luciferin), two imidazopyrazines in crustaceans (Vargula, formerly Cypridina luciferin) and coelenterates (Renilla and Aequorea luciferin), a N-isovaleryl- 3-aminopropanal in the earthworm Diplocardia, a peptide in another earthworm (Fridericia), and a benzothiazolyl thiazole in coleopterans (Fig. 2). Luciferins of the blue-emitting flies Arachnocampa (New Zealand) and Orphelia (United States of America) are still under investigation ( Viviani et al. ...
Context 4
... first acts as a ligase at costs of ATP to activate the luciferin carboxylic group as a luciferyl-adenylate anhydride (Fig. 3, 1) and sequentially as an oxygenase by inserting molecular oxygen into the luciferin α-carbanion to form an α-hydroperoxide ( Fig. 3, 2). This intermediate then undergoes cyclization with release of AMP to a putative four-membered ring peroxide (Fig.3, 3), named α-peroxylactone or dioxetanone ( Bartoloni et al. 2015, Bastos et al. 2017), whose cleavage (Fig. 3, 7) yields CO 2 and the oxyluciferin in the excited singlet, fluorescent state (Fig. 3, 4-6) (Shimomura et al. 1977, Oba et al. 2003). The topology of the luciferase active site is importantly affected by (i) the pH in lampyrid luciferases, but not in elaterids and phengodids (Viviani and Bechara 1995); (ii) the polarity of the microenvironment; and (iii) the luciferin binding and catalytic amino acids which may favor formation of the excited oxyluciferin either in its red (λ max ~ 615 nm) monoanion keto form (Fig. 3, 4) and green (540 nm) dianion enolate form (Fig. 3, 5) (Shimomura 2012, Viviani et al. 2012). These facts led to the belief that an important basic amino acid residue like arginine present, distant or absent near the nascent excited oxyluciferin assists the formation of the keto or enolate ...

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Citations

... Bioluminescence lampyrid in fireflies originates from the larval stage (Martin et al., 2017), where it acts as an aposematic signal (De Cock & Matthysen, 2003;Marek et al., 2011) that tells predators that they are unpalatable (Vencl et al., 2016). It could also be a possible tactic to attract prey (Bechara & Stevani, 2018). Attested per Moiseff and Copeland (2010), synchronous flashing is a behavioural technique to reduce visual clutter. ...
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... Bioluminescence lampyrid in fireflies originates from the larval stage (Martin et al., 2017), where it acts as an aposematic signal (De Cock & Matthysen, 2003;Marek et al., 2011) that tells predators that they are unpalatable (Vencl et al., 2016). It could also be a possible tactic to attract prey (Bechara & Stevani, 2018). Attested per Moiseff and Copeland (2010), synchronous flashing is a behavioural technique to reduce visual clutter. ...
... Bioluminescence is the result of the conversion of chemical energy into photons ( Figure 1). (Bechara & Stevani, 2018) Note. Luciferin: Oxidation of a substrate; O 2 (Luciferase): Catalysed molecular oxygen; Oxyluciferin: Singlet excited-state product Thus, using identical chemical routes involving the luciferin compound, Elateridae, Rhagophthalmidae, Phengodidae, and Lampyridae emit light, as do various structurally alike to luciferases (Day et al., 2009). ...
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Chapter
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