Luciferin

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This is a space-filling model of firefly luciferin. Color

coding: yellow=sulfur; blue=nitrogen; black=carbon;
red=oxygen; white=hydrogen.
Luciferin (from the Latin lucifer, "light-
bringer") is a generic term for the light-
emitting compound found in organisms
that generate bioluminescence. Luciferins
typically undergo an enzyme-catalysed
oxidation and the resulting excited state
intermediate emits light upon decaying to
its ground state. This may refer to
molecules that are substrates for both
luciferases and photoproteins.[1]

Types
Luciferins are a class of small-molecule
substrates that are oxidized in the
presence of a luciferase (an enzyme) to
produce energy in the form of light. It is
not known just how many types of
luciferins there are, but some of the better-
studied compounds are listed below.

Because of the chemical diversity of

luciferins, there is no clear unifying
mechanism of action, except that all
require molecular oxygen at some step,[2]
Based on the variety of luciferins and
luciferases, their diverse reaction
mechanisms and scattered phylogenetic
distribution, it is estimated that many of
them have arisen independently in the
course of evolution.[2]
Firefly …

This structure of firefly luciferin is reversed (left to

right) from the space-filling model shown above

Firefly luciferin is the luciferin found in

many Lampyridae species. It is the
substrate of beetle luciferases (EC
1.13.12.7) responsible for the
characteristic yellow light emission from
fireflies, though can cross-react to produce
light with related enzymes from non-
luminous species.[3] The chemistry is
unusual, as adenosine triphosphate (ATP)
is required for light emission, in addition to
molecular oxygen.[4]

Snail …

Latia luciferin

Latia luciferin is, in terms of chemistry,

(E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohex-
1-yl)-1-buten-1-ol formate and is from the
freshwater snail Latia neritoides.[5]

Bacterial …
 

Bacterial luciferin (FMN)

Bacterial luciferin is two-component

system consisting of flavin
mononucleotide and a fatty aldehyde
found in bioluminescent bacteria.

Coelenterazine …
 

Coelenterazine

Coelenterazine is found in radiolarians,

ctenophores, cnidarians, squid, brittle
stars, copepods, chaetognaths, fish, and
shrimp. It is the prosthetic group in the
protein aequorin responsible for the blue
light emission.[6]

Dinoflagellate …
 

Luciferin of dinoflagellates (R = H) resp. of euphausiid

shrimps (R = OH). The latter is also called Component

F.

Dinoflagellate luciferin is a chlorophyll

derivative (i. e. a tetrapyrrole) and is found
in some dinoflagellates, which are often
responsible for the phenomenon of
nighttime glowing waves (historically this
was called phosphorescence, but is a
misleading term). A very similar type of
luciferin is found in some types of
euphausiid shrimp.[7]

Vargulin …

Vargulin (cypridinluciferin)

Vargulin is found in certain ostracods and

deep-sea fish, to be specific, Poricthys.
Like the compound coelenterazine, it is an
imidazopyrazinone and emits primarily
blue light in the animals.
Fungi …

3-hydroxy hispidin from N. nambi

Foxfire is the bioluminescence created by

some species of fungi present in decaying
wood. While there may be multiple
different luciferins within the kingdom of
fungi, 3-hydroxy hispidin was determined
to be the luciferin in the fruiting bodies of
several species of fungi, including
Neonothopanus nambi, Omphalotus
olearius, Omphalotus nidiformis, and
Panellus stipticus.[8]

References
1. Hastings JW (1996). "Chemistries and
colors of bioluminescent reactions: a
review". Gene. 173 (1 Spec No): 5–11.
doi:10.1016/0378-1119(95)00676-1 .
PMID 8707056 .
2. Hastings JW (1983). "Biological
diversity, chemical mechanisms, and
the evolutionary origins of
bioluminescent systems". J. Mol. Evol.
19 (5): 309–21.
Bibcode:1983JMolE..19..309H .
 doi:10.1007/BF02101634 .
PMID 6358519 .
3. Viviani, V.R., Bechara, E.J.H. (1996).
"Larval Tenebrio molitor (Coleoptera:
Tenebrionidae) Fat Body Extracts
Catalyze Firefly D-Luciferin-and ATP-
Dependent Chemiluminescence: A
Luciferase-like Enzyme".
Photochemistry and Photobiology. 63
(6): 713–718. doi:10.1111/j.1751-
1097.1996.tb09620.x .
4. Green A, McElroy WD (October 1956).
"Function of adenosine triphosphate in
the activation of luciferin". Arch.
Biochem. Biophys. 64 (2): 257–71.
 doi:10.1016/0003-9861(56)90268-5 .
PMID 13363432 .
5. EC 1.14.99.21 . ORENZA: a database
of ORphan ENZyme Activities,
accessed 27 November 2009.
6. Shimomura O, Johnson FH (April
1975). "Chemical nature of
bioluminescence systems in
coelenterates" . Proc. Natl. Acad. Sci.
U.S.A. 72 (4): 1546–49.
Bibcode:1975PNAS...72.1546S .
doi:10.1073/pnas.72.4.1546 .
PMC 432574 . PMID 236561 .
7. Dunlap, JC; Hastings, JW; Shimomura,
O (1980). "Crossreactivity between the
 light-emitting systems of distantly
related organisms: Novel type of light-
emitting compound" . Proc. Natl.
Acad. Sci. U.S.A. 77 (3): 1394–97.
Bibcode:1980PNAS...77.1394D .
doi:10.1073/pnas.77.3.1394 .
PMC 348501 . PMID 16592787 .
8. Purtov KV, Petushkov VN, Baranov MS,
Mineev KS, Rodionova NS, Kaskova
ZM, Tsarkova AS, Petunin AI, Bondar
VS, Rodicheva EK, Medvedeva SE, Oba
Y, Arseniev AS, Lukyanov S, Gitelson JI,
Yampolsky IV (2015). "The Chemical
Basis of Fungal Bioluminescence".
Angewandte Chemie International
Edition. 54 (28): 8124–8128.
 doi:10.1002/anie.201501779 .
PMID 26094784 .

External links
"Major luciferin types" . The
Bioluminescence Web Page. University of
California, Santa Barbara. 2009-01-09.
Retrieved 2009-03-06.

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Last edited 3 months ago by WDistrict

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