Luciferin biosynthesis in larval Pyrearinus termitilluminans (Coleoptera: elateridae)

Colepicolo, Pio; Pagni, Daniele; Bechara, Etelvino J.H.

doi:10.1016/0305-0491(88)90126-5

Cited by 5 publications

(6 citation statements)

References 11 publications

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“…Thus, similar to the method using the radioisotope-labeled compounds, the method of mass spectral analysis accompanied by the incorporation of stable isotope-labeled compounds is useful for investigating the biosynthetic process. With regard to studies on the biosynthesis of luciferin in firefly and click beetle, four biochemical investigations involving incorporation experiments with 14 C-labeled compounds have been reported [14] – [17] and studies using biomimetic synthesis have also been reported [16] , [18] .…”

Section: Introductionmentioning

confidence: 99%

“…However, the configuration of cysteine incorporated in beetle luciferin and the incorporation of cysteine into the benzothiazole ring with decarboxylation were not revealed. Further, in 1988, the injection experiment of [U- 14 C 6 ]-cystine into the larvae of the luminous click beetle Pyrearinus termitilluminans was performed, and the 14 C-labeled luciferin was extracted and was determined by TLC without the addition of luciferin [17] . As a result, cysteine from [U- 14 C 6 ]-cystine was incorporated into luciferin, similar to the case of adult P. pellucens [16] .…”

Section: Introductionmentioning

confidence: 99%

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Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of ʟ-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis

et al. 2013

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BackgroundBioluminescence in fireflies and click beetles is produced by a luciferase-luciferin reaction. The luminescence property and protein structure of firefly luciferase have been investigated, and its cDNA has been used for various assay systems. The chemical structure of firefly luciferin was identified as the ᴅ-form in 1963 and studies on the biosynthesis of firefly luciferin began early in the 1970’s. Incorporation experiments using 14C-labeled compounds were performed, and cysteine and benzoquinone/hydroquinone were proposed to be biosynthetic component for firefly luciferin. However, there have been no clear conclusions regarding the biosynthetic components of firefly luciferin over 30 years.Methodology/Principal FindingsIncorporation studies were performed by injecting stable isotope-labeled compounds, including ʟ-[U-13C3]-cysteine, ʟ-[1-13C]-cysteine, ʟ-[3-13C]-cysteine, 1,4-[D6]-hydroquinone, and p-[2,3,5,6-D]-benzoquinone, into the adult lantern of the living Japanese firefly Luciola lateralis. After extracting firefly luciferin from the lantern, the incorporation of stable isotope-labeled compounds into firefly luciferin was identified by LC/ESI-TOF-MS. The positions of the stable isotope atoms in firefly luciferin were determined by the mass fragmentation of firefly luciferin.ConclusionsWe demonstrated for the first time that ᴅ- and ʟ-firefly luciferins are biosynthesized in the lantern of the adult firefly from two ʟ-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of ʟ-cysteine.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of ʟ-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis

et al. 2013

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“…The bioluminescence systems used in these applications rely solely on commercially synthesized luciferin. Many attempts to resolve the luciferin biosynthetic pathway have been performed ( Okada et al, 1974 ; Okada, Iio & Goto, 1976 ; McCapra & Razavi, 1975 ; McCapra & Razavi, 1976 ; Colepicolo, Pagni & Bechara, 1988 ; Niwa, Nakamura & Ohmiya, 2006 ). Recently, Oba et al (2013) analyzed the luciferin biosynthetic pathway by injection of isotope-labeled compounds L-cysteine, hydroquinone, and benzoquinone into an adult lantern of firefly L. lateralis .…”

Section: Introductionmentioning

confidence: 99%

Transcriptome analysis reveals candidate genes involved in luciferin metabolism inLuciola aquatilis(Coleoptera: Lampyridae)

Vongsangnak

Chumnanpuen

Sriboonlert

2016

PeerJ

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Bioluminescence, which living organisms such as fireflies emit light, has been studied extensively for over half a century. This intriguing reaction, having its origins in nature where glowing insects can signal things such as attraction or defense, is now widely used in biotechnology with applications of bioluminescence and chemiluminescence. Luciferase, a key enzyme in this reaction, has been well characterized; however, the enzymes involved in the biosynthetic pathway of its substrate, luciferin, remains unsolved at present. To elucidate the luciferin metabolism, we performed a de novo transcriptome analysis using larvae of the firefly species, Luciola aquatilis. Here, a comparative analysis is performed with the model coleopteran insect Tribolium casteneum to elucidate the metabolic pathways in L. aquatilis. Based on a template luciferin biosynthetic pathway, combined with a range of protein and pathway databases, and various prediction tools for functional annotation, the candidate genes, enzymes, and biochemical reactions involved in luciferin metabolism are proposed for L. aquatilis. The candidate gene expression is validated in the adult L. aquatilis using reverse transcription PCR (RT-PCR). This study provides useful information on the bio-production of luciferin in the firefly and will benefit to future applications of the valuable firefly bioluminescence system.

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“…The putative biosynthetic precursors of d ‐luciferin are also cysteine and CHBT [6]. Incorporations of isotope‐labeled dl ‐cystine and CHBT into d ‐luciferin in fireflies have been reported [7–9]. However, the detail biosynthetic mechanism of firefly d ‐luciferin has remained ambiguous for almost half a century since the first report of its chemical structure [5].…”

Section: Introductionmentioning

confidence: 99%

Stereoisomeric bio‐inversion key to biosynthesis of firefly d‐luciferin

2006

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Luciferin biosynthesis in larval Pyrearinus termitilluminans (Coleoptera: elateridae)

Cited by 5 publications

References 11 publications

Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of ʟ-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis

Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of ʟ-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis

Transcriptome analysis reveals candidate genes involved in luciferin metabolism inLuciola aquatilis(Coleoptera: Lampyridae)

Stereoisomeric bio‐inversion key to biosynthesis of firefly d‐luciferin

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