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Yuichi Oba - One of the best experts on this subject based on the ideXlab platform.
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resurrecting the ancient glow of the fireflies
Science Advances, 2020Co-Authors: Yuichi Oba, Kaori Konishi, Daichi Yano, Hideyuki Shibata, Daiichiro Kato, Tsuyoshi ShiraiAbstract:The color of Firefly bioluminescence is determined by the structure of luciferase. Firefly luciferase genes have been isolated from more than 30 species, producing light ranging in color from green to orange-yellow. Here, we reconstructed seven ancestral Firefly luciferase genes, characterized the enzymatic properties of the recombinant proteins, and determined the crystal structures of the gene from ancestral Lampyridae. Results showed that the synthetic luciferase for the last common Firefly ancestor exhibited green light caused by a spatial constraint on the luciferin molecule in enzyme, while fatty acyl-CoA synthetic activity, an original function of Firefly luciferase, was diminished in exchange. All known Firefly species are bioluminescent in the larvae, with a common ancestor arising approximately 100 million years ago. Combined, our findings propose that, within the mid-Cretaceous forest, the common ancestor of fireflies evolved green light luciferase via trade-off of the original function, which was likely aposematic warning display against nocturnal predation.
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one pot non enzymatic formation of Firefly luciferin in a neutral buffer from p benzoquinone and cysteine
Scientific Reports, 2016Co-Authors: Shusei Kanie, Yuichi Oba, Makoto Ojika, Toshio NishikawaAbstract:Firefly luciferin, the substrate for the bioluminescence reaction of luminous beetles, possesses a benzothiazole ring, which is rare in nature. Here, we demonstrate a novel one-pot reaction to give Firefly luciferin in a neutral buffer from p-benzoquinone and cysteine without any synthetic reagents or enzymes. The formation of Firefly luciferin was low in yield in various neutral buffers, whereas it was inhibited or completely prevented in acidic or basic buffers, in organic solvents, or under a nitrogen atmosphere. Labelling analysis of the Firefly luciferin using stable isotopic cysteines showed that the benzothiazole ring was formed via the decarboxylation and carbon-sulfur bond rearrangement of cysteine. These findings imply that the biosynthesis of Firefly luciferin can be developed/evolved from the non-enzymatic production of Firefly luciferin using common primary biosynthetic units, p-benzoquinone and cysteine.
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Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of L-Cysteine Is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract:Background: Bioluminescence 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 D-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 Findings: Incorporation studies were performed by injecting stable isotope-labeled compounds, including L-[U-13C3]-cysteine, L-[1-13C]-cysteine, L-[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. Conclusions: We demonstrated for the first time that D- and L-Firefly luciferins are biosynthesized in the lantern of the adult Firefly from two L-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of L
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Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of L-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract: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 D-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 L-[U-13C3]-cysteine, L-[1-13C]-cysteine, L-[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 D- and L-Firefly luciferins are biosynthesized in the lantern of the adult Firefly from two L-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of L-cysteine.
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Mass spectrum of D-Firefly luciferin by ESI-TOF-MS analysis.
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract:A. The structure of D-Firefly luciferin and the predicted mass fragment ions. The parent ion of D-luciferin at m/z 281 (M+H)+ (a), and its fragment ions at m/z 235 (b) and 177 (c). B. ESI-TOF-MS analysis of synthetic D-Firefly luciferin.
Christopher K Cratsley - One of the best experts on this subject based on the ideXlab platform.
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Flash Signal Evolution, Mate Choice, and Predation in Fireflies
Annual Review of Entomology, 2008Co-Authors: Sara M. Lewis, Christopher K CratsleyAbstract:Many key advances in our understanding of Firefly biology and signaling have been made over the past two decades. Here we review this recent research, which includes new phylogenetic results that shed light on the evolution of courtship signal diversity within the family Lampyridae, new insights into Firefly flash control, and the discovery of Firefly nuptial gifts. We present a comprehensive overview of sexual selection in lampyrids, including evidence from Photinus fireflies that females choose their mates on the basis of male flash signals, and discuss the importance of examining both precopulatory and postcopulatory sexual selection in this group. Finally, we review recent findings on Firefly chemical defenses, and discuss their implications for flash signal evolution in response to generalist predators as well as specialist predatory fireflies. This review provides new insight into how Firefly flash signals have been shaped by the dual evolutionary processes of sexual selection (mate choice) and natural selection (predation), and proposes several exciting directions for future research
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flash signal evolution mate choice and predation in fireflies
Annual Review of Entomology, 2008Co-Authors: Sara M. Lewis, Christopher K CratsleyAbstract:Many key advances in our understanding of Firefly biology and signaling have been made over the past two decades. Here we review this recent research, which includes new phylogenetic results that shed light on the evolution of courtship signal diversity within the family Lampyridae, new insights into Firefly flash control, and the discovery of Firefly nuptial gifts. We present a comprehensive overview of sexual selection in lampyrids, including evidence from Photinus fireflies that females choose their mates on the basis of male flash signals, and discuss the importance of examining both precopulatory and postcopulatory sexual selection in this group. Finally, we review recent findings on Firefly chemical defenses, and discuss their implications for flash signal evolution in response to generalist predators as well as specialist predatory fireflies. This review provides new insight into how Firefly flash signals have been shaped by the dual evolutionary processes of sexual selection (mate choice) and natu...
Stephen C Miller - One of the best experts on this subject based on the ideXlab platform.
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luciferin amides enable in vivo bioluminescence detection of endogenous fatty acid amide hydrolase activity
Journal of the American Chemical Society, 2015Co-Authors: David M Mofford, Gadarla Randheer Reddy, Spencer T Adams, G Kiran Kumar S Reddy, Stephen C MillerAbstract:Firefly luciferase is homologous to fatty acyl-CoA synthetases. We hypothesized that the Firefly luciferase substrate d-luciferin and its analogs are fatty acid mimics that are ideally suited to probe the chemistry of enzymes that release fatty acid products. Here, we synthesized luciferin amides and found that these molecules are hydrolyzed to substrates for Firefly luciferase by the enzyme fatty acid amide hydrolase (FAAH). In the presence of luciferase, these molecules enable highly sensitive and selective bioluminescent detection of FAAH activity in vitro, in live cells, and in vivo. The potency and tissue distribution of FAAH inhibitors can be imaged in live mice, and luciferin amides serve as exemplary reagents for greatly improved bioluminescence imaging in FAAH-expressing tissues such as the brain.
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Luciferin Amides Enable in Vivo Bioluminescence Detection of Endogenous Fatty Acid Amide Hydrolase Activity
2015Co-Authors: David M Mofford, Gadarla Randheer Reddy, Spencer T Adams, G Kiran Kumar S Reddy, Stephen C MillerAbstract:Firefly luciferase is homologous to fatty acyl-CoA synthetases. We hypothesized that the Firefly luciferase substrate d-luciferin and its analogs are fatty acid mimics that are ideally suited to probe the chemistry of enzymes that release fatty acid products. Here, we synthesized luciferin amides and found that these molecules are hydrolyzed to substrates for Firefly luciferase by the enzyme fatty acid amide hydrolase (FAAH). In the presence of luciferase, these molecules enable highly sensitive and selective bioluminescent detection of FAAH activity in vitro, in live cells, and in vivo. The potency and tissue distribution of FAAH inhibitors can be imaged in live mice, and luciferin amides serve as exemplary reagents for greatly improved bioluminescence imaging in FAAH-expressing tissues such as the brain
Satoshi Inouye - One of the best experts on this subject based on the ideXlab platform.
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Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of L-Cysteine Is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract:Background: Bioluminescence 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 D-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 Findings: Incorporation studies were performed by injecting stable isotope-labeled compounds, including L-[U-13C3]-cysteine, L-[1-13C]-cysteine, L-[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. Conclusions: We demonstrated for the first time that D- and L-Firefly luciferins are biosynthesized in the lantern of the adult Firefly from two L-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of L
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Biosynthesis of Firefly Luciferin in Adult Lantern: Decarboxylation of L-Cysteine is a Key Step for Benzothiazole Ring Formation in Firefly Luciferin Synthesis
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract: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 D-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 L-[U-13C3]-cysteine, L-[1-13C]-cysteine, L-[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 D- and L-Firefly luciferins are biosynthesized in the lantern of the adult Firefly from two L-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of L-cysteine.
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Mass spectrum of D-Firefly luciferin by ESI-TOF-MS analysis.
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract:A. The structure of D-Firefly luciferin and the predicted mass fragment ions. The parent ion of D-luciferin at m/z 281 (M+H)+ (a), and its fragment ions at m/z 235 (b) and 177 (c). B. ESI-TOF-MS analysis of synthetic D-Firefly luciferin.
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Proposed biosynthetic pathway of Firefly luciferin in the lantern of adult Firefly.
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract:Proposed biosynthetic pathway of Firefly luciferin in the lantern of adult Firefly.
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Relative isotopic peak intensities (%) of the parent and its fragment mass from Firefly luciferin in the lantern extracts after injecting L-Cys[U-13C3] with 1,4-hydroquinone or p-benzoquinone into the adult of L. lateralis.
2013Co-Authors: Yuichi Oba, Makoto Ojika, Shusei Kanie, Naoki Yoshida, Satoshi InouyeAbstract:a (a) represents the parent mass of Firefly luciferin with MH+281 (+0, 100%). (b) and (c) represent the fragment ion mass from Firefly luciferin with MH+235 (+0, 100%) and MH+177 (+0, 100%), respectively, as shown in Fig. 2. The numbers in bold are the significant mass peaks containing the incorporated stable isotope atoms.
Sara M. Lewis - One of the best experts on this subject based on the ideXlab platform.
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Flash Signal Evolution, Mate Choice, and Predation in Fireflies
Annual Review of Entomology, 2008Co-Authors: Sara M. Lewis, Christopher K CratsleyAbstract:Many key advances in our understanding of Firefly biology and signaling have been made over the past two decades. Here we review this recent research, which includes new phylogenetic results that shed light on the evolution of courtship signal diversity within the family Lampyridae, new insights into Firefly flash control, and the discovery of Firefly nuptial gifts. We present a comprehensive overview of sexual selection in lampyrids, including evidence from Photinus fireflies that females choose their mates on the basis of male flash signals, and discuss the importance of examining both precopulatory and postcopulatory sexual selection in this group. Finally, we review recent findings on Firefly chemical defenses, and discuss their implications for flash signal evolution in response to generalist predators as well as specialist predatory fireflies. This review provides new insight into how Firefly flash signals have been shaped by the dual evolutionary processes of sexual selection (mate choice) and natural selection (predation), and proposes several exciting directions for future research
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flash signal evolution mate choice and predation in fireflies
Annual Review of Entomology, 2008Co-Authors: Sara M. Lewis, Christopher K CratsleyAbstract:Many key advances in our understanding of Firefly biology and signaling have been made over the past two decades. Here we review this recent research, which includes new phylogenetic results that shed light on the evolution of courtship signal diversity within the family Lampyridae, new insights into Firefly flash control, and the discovery of Firefly nuptial gifts. We present a comprehensive overview of sexual selection in lampyrids, including evidence from Photinus fireflies that females choose their mates on the basis of male flash signals, and discuss the importance of examining both precopulatory and postcopulatory sexual selection in this group. Finally, we review recent findings on Firefly chemical defenses, and discuss their implications for flash signal evolution in response to generalist predators as well as specialist predatory fireflies. This review provides new insight into how Firefly flash signals have been shaped by the dual evolutionary processes of sexual selection (mate choice) and natu...
