A practical, biomimetic, one-pot synthesis of firefly luciferin.

The bioluminescence reaction of firefly luciferase with D-luciferin has become an indispensable imaging technique in modern biology and life science experiments, but the high cost of D-luciferin is limiting its further application. Here, we report a practical, one-pot synthesis of D-luciferin from p-benzoquinone (p-BQ), L-cysteine methyl ester and D-cysteine, with an overall yield of 46%. Our route, which is six steps in length and proceeds via 2-cyano-6-hydroxybenzothiazole, is inspired by the mechanistic study of our previously reported biomimetic, non-enzymatic, one-pot formation of L-luciferin from p-BQ and L-cysteine.

Global species delimitation of the cosmopolitan marine littoral earthworm Pontodrilus litoralis (Grube, 1855).

The marine littoral earthworm Pontodrilus litoralis (Grube, 1855) is widely distributed and is reported as a single species. This study utilized an integrative taxonomic approach based upon morphological examination, phylogenetic reconstruction, and molecular species delimitation, to test whether the taxon is a single species or a species complex. For this, a total of 114 P.

Contribution to the taxonomy of Lobellini (Collembola: Neanurinae) and investigations on luminous Collembola from Japan.

Lobella sauteri was redescribed based on the lectotype and specimens obtained from the type locality Bugenji, Yokohama, Kanagawa, as the true identity of the luminous Collembola, Lobella sp. Lobella sauteri has morphological traits characteristic of the genus currently called Telobella. As L.

A new species of the genus sensu lato () from Hachijo Island, Japan.

sp. nov. is described and illustrated.

A new discovery of the bioluminescent terrestrial snail genus Phuphania (Gastropoda: Dyakiidae).

The mysterious world of the bioluminescent molluscs in terrestrial ecosystems is mesmerizing, but Quantula striata was previously the only terrestrial mollusc known to be luminescent. Here, we document the new discovery of bioluminescence in four land snails, namely Phuphania crossei, P. globosa, P.

The Luminous Fungi of Japan.

Luminous fungi have long attracted public attention in Japan, from old folklore and fiction to current tourism, children's toys, games, and picture books. At present, 25 species of luminous fungi have been discovered in Japan, which correspond to approximately one-fourth of the globally recognized species. This species richness is arguably due to the abundant presence of mycophiles looking to find new mushroom species and a tradition of night-time activities, such as firefly watching, in Japan.

Flickering flash signals and mate recognition in the Asian firefly, Aquatica lateralis.

Nocturnal fireflies sometimes use intricate bioluminescent signal systems for sexual communication. In this study, we examined flash signals and mate recognition in the Asian firefly, Aquatica lateralis, under natural field conditions. We found that the flash pattern of females changes after copulation, from simple short flashes to flashes with longer duration and flickering.

14-3-3 proteins are luciferases candidate proteins from lanternfish Diaphus watasei.

The lanternfish is a deep-sea fish with ventral-lateral and head photophores. It uses its ventral-lateral photophores to camouflage its ventral silhouette, a strategy called counterillumination. The bioluminescent reaction of lanternfish involves coelenterazine as a substrate luciferin but the enzyme catalyzing the bioluminescent reaction has not been identified.

Firefly genomes illuminate the evolution of beetle bioluminescent systems.

Fireflies are one of the best-known bioluminescent organisms, and the reaction mechanism and ecological utility of bioluminescence have been well-studied. Genome assemblies of six species of bioluminescent beetles have recently been published. These studies have focused on the evolution of novelties; luciferase, and the biosynthesis of luciferin and defensive chemicals.

Etmopterus lantern sharks use coelenterazine as the substrate for their luciferin-luciferase bioluminescence system.

The lantern shark genus Etmopterus contains approximately 40 species of deep-sea bioluminescent cartilaginous fishes. They emit blue light mainly from the ventral body surface. The biological functions of this bioluminescence have been discussed based on the luminescence patterns, but the bioluminescence mechanism remains uncertain.

Occurrence of bioluminescent and nonbioluminescent species in the littoral earthworm genus Pontodrilus.

Pontodrilus litoralis is a cosmopolitan littoral earthworm known to exhibit bioluminescence. Recently, a congeneric species, Pontodrilus longissimus, from Thailand was described. These species are sympatric, but their burrowing depths on Thai beaches are different.

Kleptoprotein bioluminescence: fish obtain luciferase from ostracod prey.

Through their diet, animals can obtain substances essential for imparting special characteristics, such as toxins in monarch butterflies and luminescent substances in jellyfishes. These substances are typically small molecules because they are less likely to be digested and may be hard for the consumer to biosynthesize. Here, we report that , a bioluminescent fish, obtains not only its luciferin but also its luciferase enzyme from bioluminescent ostracod prey.

Reflector of the body photophore in lanternfish is mechanistically tuned to project the biochemical emission in photocytes for counterillumination.

Lanternfish, a family Myctophidae, use ventro-lateral body photophores for camouflage of the ventral silhouette, a strategy called counterillumination. While other deep-sea fishes possess pigmented filters and silver reflectors to match sunlight filtering down through the depths, myctophids developed a blue-green reflector for this purpose. In this study, we showed in a lanternfish Diaphus watasei that the reflector comprised monolayered iridophores containing multilayered guanine crystals which enable high reflection with light interference colouration.

Bioluminescence chemistry of fireworm .

Marine polychaetes , commonly known as fireworms, emit bright blue-green bioluminescence. Until the recent identification of the luciferase enzyme, little progress had been made toward characterizing the key components of this bioluminescence system. Here we present the biomolecular mechanisms of enzymatic (leading to light emission) and nonenzymatic (dark) oxidation pathways of newly described luciferin.

Size variation and geographical distribution of the luminous earthworm (Grube, 1855) (Clitellata, Megascolecidae) in Southeast Asia and Japan.

The luminous earthworm (Grube, 1855) occurs in a very wide range of subtropical and tropical coastal areas. Morphometrics on size variation (number of segments, body length and diameter) and genetic analysis using the mitochondrial cytochrome c oxidase subunit 1 (COI) gene sequence were conducted on 14 populations of from Southeast Asia and Japan. Statistical inference on morphometric data revealed significantly different size variations in the body length and diameter among these 14 populations of .

Bioluminescence properties of Thelepus japonicus (Annelida: Terebelliformia).

Terebelliformia is a benthic group of marine annelid worms. The bioluminescence of several species has been reported in taxonomical and histological literature, but very little information is known about the biochemical aspects of this phenomenon. In this study, we examined the basic properties of the luminescence system using an extract of the Japanese terebelliform worm, Thelepus japonicus.

Genetically encodable bioluminescent system from fungi.

Bioluminescence is found across the entire tree of life, conferring a spectacular set of visually oriented functions from attracting mates to scaring off predators. Half a dozen different luciferins, molecules that emit light when enzymatically oxidized, are known. However, just one biochemical pathway for luciferin biosynthesis has been described in full, which is found only in bacteria.

Firefly genomes illuminate parallel origins of bioluminescence in beetles.

Fireflies and their luminous courtships have inspired centuries of scientific study. Today firefly luciferase is widely used in biotechnology, but the evolutionary origin of bioluminescence within beetles remains unclear. To shed light on this long-standing question, we sequenced the genomes of two firefly species that diverged over 100 million-years-ago: the North American and Japanese To compare bioluminescent origins, we also sequenced the genome of a related click beetle, the Caribbean , with bioluminescent biochemistry near-identical to fireflies, but anatomically unique light organs, suggesting the intriguing hypothesis of parallel gains of bioluminescence.

2-S-cysteinylhydroquinone is an intermediate for the firefly luciferin biosynthesis that occurs in the pupal stage of the Japanese firefly, Luciola lateralis.

Firefly luciferin is a natural product that is well-known to function as the substrate of the bioluminescence reaction in luminous beetles. However, the details of the biosynthetic system are still unclear. In this study, we showed by LC-MS/MS analysis that stable isotope-labeled 2-S-cysteinylhydroquinone was incorporated into firefly luciferin in living firefly specimens.

Luciferase of the Japanese syllid polychaete Odontosyllis undecimdonta.

Odontosyllis undecimdonta is a marine syllid polychaete that produces bright internal and exuded bioluminescence. Despite over fifty years of biochemical investigation into Odontosyllis bioluminescence, the light-emitting small molecule substrate and catalyzing luciferase protein have remained a mystery. Here we describe the discovery of a bioluminescent protein fraction from O.

Identification of hispidin as a bioluminescent active compound and its recycling biosynthesis in the luminous fungal fruiting body.

We previously showed that luminous fungi share a common mechanism in bioluminescence, and identified hispidin as a luciferin precursor in Neonothopanus nambi mycelium. Here we showed the presence of hispidin as a bioluminescent active compound at 25-1000 pmol g in the fruiting bodies of Mycena chlorophos, Omphalotus japonicus, and Neonothopanus gardneri. These results suggest that luminous mushrooms contain hispidin as a luciferin precursor.

Biochemical characteristics and gene expression profiles of two paralogous luciferases from the Japanese firefly Pyrocoelia atripennis (Coleoptera, Lampyridae, Lampyrinae): insight into the evolution of firefly luciferase genes.

Two paralogous genes of firefly luciferase, Luc1 and Luc2, have been isolated from the species in two subfamilies, Luciolinae and Photurinae, of the family Lampyridae. The gene expression profiles have previously been examined only in the species of Luciolinae. Here we isolated Luc1 and Luc2 genes from the Japanese firefly Pyrocoelia atripennis.

Mechanism and color modulation of fungal bioluminescence.

Bioluminescent fungi are spread throughout the globe, but details on their mechanism of light emission are still scarce. Usually, the process involves three key components: an oxidizable luciferin substrate, a luciferase enzyme, and a light emitter, typically oxidized luciferin, and called oxyluciferin. We report the structure of fungal oxyluciferin, investigate the mechanism of fungal bioluminescence, and describe the use of simple synthetic α-pyrones as luciferins to produce multicolor enzymatic chemiluminescence.

Identification and characterization of the Luc2-type luciferase in the Japanese firefly, Luciola parvula, involved in a dim luminescence in immobile stages.

Nocturnal Japanese fireflies, Luciola parvula, emit from their lanterns a yellow light, one of the most red-shifted colors found among fireflies. Previously, we isolated and characterized two different types of luciferase gene, Luc1 and Luc2, from the fireflies Luciola cruciata and Luciola lateralis; Luc1 is responsible for the green-yellow luminescence of larval and adult lanterns, whereas Luc2 is responsible for the dim greenish glow of eggs and pupal bodies. The biological role of firefly lanterns in adults is related to sexual communication, but why the eggs and pupae glow remains uncertain.