Scytonemin: Difference between revisions

Scytonemin
Names
	IUPAC name (3E,3'E)-3,3'-bis(4-hydroxybenzylidene)-[1,1'-bi(cyclopenta[b]indole)]-2,2'(3H,3'H)-dione
	Other names Scytonemin
Identifiers
CAS Number	152075-98-4;
CompTox Dashboard (EPA)	DTXSID60934418 ;
Properties
Chemical formula	C36H20N2O4
Molar mass	544.6 g/mol
Appearance	brown solid
UV-vis (λmax)	325-425nm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Scytonemin

Scytonemin is a biological pigment synthesized by many strains of cyanobacteria, including Calothrix sp.^[2], Lyngbya aestuarii^[3], and others. It was originally discovered in 1849, although the structure remained unsolved until 1993^[4]. Scytonemin is believed to act as a sunscreen with a broad absorption from 325-425nm and a separate maxima at 250nm^[5], and its biosynthesis triggered by exposure to UV light^[6].

Biosynthesis

The biosynthesis in Lyngbya aestuarii was recently explored by Balskus, Case, and Walsh.

References

^ "Scytonemin CAS (152075-98-4)". Santa Cruz Biotechnology, Inc. Retrieved 5/30/2011. {{cite web}}: Check date values in: |accessdate= (help)
^ Castenholz, RW (2003). "The synthesis of the UV-screening pigment, scytonemin, and photosynthetic performance in isolates from closely related natural populations of cyanobacteria (Calothrix sp.)". Environ Microbiol. 5 (6): 484–91. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ Walsh, CT (18). "The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities". FEMS Bicrobiol. Ecol.: 1–11. doi:10.1111/j.1574-6941.2011.01113.x. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate=, |date=, and |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ Castenholz, R (1993). "The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria". Experientia. 49: 825–829. doi:10.1007/BF01923559. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ Castenholz, R (1993). "The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria". Experientia. 49: 825–829. doi:10.1007/BF01923559. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ Bandaranayake, Wickramasinghe (1998). "Mycosporines: are they nature's sunscreens?". Nat. Prod. Rep. 15: 159–172. doi:10.1039/A815159Y. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate= (help)
^ Walsh, CT (18). "The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities". FEMS Bicrobiol. Ecol.: 1–11. doi:10.1111/j.1574-6941.2011.01113.x. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate=, |date=, and |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

External links

http://www.ncbi.nlm.nih.gov/pubmed/21501195

[1] "Scytonemin CAS (152075-98-4)". Santa Cruz Biotechnology, Inc. Retrieved 5/30/2011. {{cite web}}: Check date values in: |accessdate= (help)

[2] Castenholz, RW (2003). "The synthesis of the UV-screening pigment, scytonemin, and photosynthetic performance in isolates from closely related natural populations of cyanobacteria (Calothrix sp.)". Environ Microbiol. 5 (6): 484–91. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[3] Walsh, CT (18). "The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities". FEMS Bicrobiol. Ecol.: 1–11. doi:10.1111/j.1574-6941.2011.01113.x. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate=, |date=, and |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[4] Castenholz, R (1993). "The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria". Experientia. 49: 825–829. doi:10.1007/BF01923559. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

[5] Castenholz, R (1993). "The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria". Experientia. 49: 825–829. doi:10.1007/BF01923559. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)

[6] Bandaranayake, Wickramasinghe (1998). "Mycosporines: are they nature's sunscreens?". Nat. Prod. Rep. 15: 159–172. doi:10.1039/A815159Y. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate= (help)

[7] Walsh, CT (18). "The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities". FEMS Bicrobiol. Ecol.: 1–11. doi:10.1111/j.1574-6941.2011.01113.x. Retrieved 5/30/2011. {{cite journal}}: Check date values in: |accessdate=, |date=, and |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

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@@ Line 16: / Line 16: @@
 |  Formula = C<sub>36</sub>H<sub>20</sub>N<sub>2</sub>O<sub>4</sub>
 |  MolarMass = 544.6 g/mol
+|  MolarMass_notes =
 |  Appearance = brown solid<ref>{{cite web|title=Scytonemin CAS (152075-98-4)|url=http://www.scbt.com/datasheet-202337-scytonemin.html|publisher=Santa Cruz Biotechnology, Inc.|accessdate=5/30/2011}}</ref>
 |  Density =
 |  MeltingPt =
+|  Melting_notes =
 |  BoilingPt =
-|  Solubility = }}
+|  Boiling_notes =
+|  SublimationConditions =
+|  Solubility =
+| SolubilityProduct =
+| SolubilityProductAs =
+| SolubilityOther = 25mg/ml DMSO
+| Solvent =
+| pKa =
+| pKb =
+| IsoElectricPt =
+| LambdaMax = 325-425nm
+| Absorbance =
+| BandGap =
+| ElectronMobility =
+| SpecRotation =
+| MagSus =
+| ThermalConductivity =
+| RefractIndex =
+| Viscosity =
+| CriticalRelativeHumidity =
+| Dipole =
+| Sheet Resistance =
+| Methacrylate Equiv Wt =
+| Bulk Conductivity =
+| AveragePoreSize =
+| PoreVolume =
+| SpecificSurfaceArea = }}
 | Section3 = {{Chembox Hazards
 |  MainHazards =
@@ Line 27: / Line 55: @@
 }}
-Scytonemin is a [[biological pigment]] synthesized by many strains of [[cyanobacteria]], including ''Calothrix sp.''<ref>Dillon JG, Castenholz RW. Environ Microbiol. 2003 Jun;5(6):484-91.</ref>, ''Lyngbya aestuarii''<ref>Balskus EP, Case RJ, Walsh CT. FEMS Microbiol Ecol. 2011 Apr 18. doi: 10.1111/j.1574-6941.2011.01113.x.</ref>, and others. Scytonemin is believed to act as a [[sunscreen]] with an absorption spectrum over 325-425nm, and its [[biosynthesis]] triggered by exposure to [[UV light]]. <br />
+Scytonemin is a [[biological pigment]] synthesized by many strains of [[cyanobacteria]], including ''Calothrix sp.''<ref>{{cite journal|last=Castenholz|first=RW|coauthors=Dillon, JG|title=The synthesis of the UV-screening pigment, scytonemin, and photosynthetic performance in isolates from closely related natural populations of cyanobacteria (Calothrix sp.).|journal=Environ Microbiol.|year=2003|month=Jun|volume=5|issue=6|pages=484-91}}</ref>, ''Lyngbya aestuarii''<ref>{{cite journal|last=Walsh|first=CT|coauthors=Balskus EP, Case RJ|title=The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities.|journal=FEMS Bicrobiol. Ecol.|date=18|year=2011|month=April|pages=1-11|doi=10.1111/j.1574-6941.2011.01113.x|url=http://www.ncbi.nlm.nih.gov/pubmed/21501195|accessdate=5/30/2011}}</ref>, and others. It was originally discovered in 1849, although the structure remained unsolved until 1993<ref>{{cite journal|last=Castenholz|first=R|coauthors=PJ Proteau, WH Gerwick, F Garcia-Pichel|title=The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria|journal=Experientia|year=1993|volume=49|pages=825-829|doi=10.1007/BF01923559|url=http://www.springerlink.com/content/lk3483k2615k503u/|accessdate=5/30/2011}}</ref>. Scytonemin is believed to act as a [[sunscreen]] with a broad absorption from 325-425nm and a separate maxima at 250nm<ref>{{cite journal|last=Castenholz|first=R|coauthors=PJ Proteau, WH Gerwick, F Garcia-Pichel|title=The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria|journal=Experientia|year=1993|volume=49|pages=825-829|doi=10.1007/BF01923559|url=http://www.springerlink.com/content/lk3483k2615k503u/|accessdate=5/30/2011}}</ref>, and its [[biosynthesis]] triggered by exposure to [[UV light]]<ref>{{cite journal|last=Bandaranayake|first=Wickramasinghe|title=Mycosporines: are they nature's sunscreens?|journal=Nat. Prod. Rep.|year=1998|volume=15|pages=159-172|doi=10.1039/A815159Y|url=http://pubs.rsc.org/en/Content/ArticleLanding/1998/NP/a815159y|accessdate=5/30/2011}}</ref>. <br />
-<br />
 == Biosynthesis ==
 The biosynthesis in ''Lyngbya aestuarii'' was recently explored by Balskus, Case, and Walsh.
-[[Image:Scytonemin biosynthesis.svg|800px|Scytonemin biosynthesis in ''Lyngbya aestuarii''.]]
+[[Image:Scytonemin biosynthesis.svg|center|800px|Scytonemin biosynthesis in ''Lyngbya aestuarii''.<ref>{{cite journal|last=Walsh|first=CT|coauthors=Balskus EP, Case RJ|title=The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities.|journal=FEMS Bicrobiol. Ecol.|date=18|year=2011|month=April|pages=1-11|doi=10.1111/j.1574-6941.2011.01113.x|url=http://www.ncbi.nlm.nih.gov/pubmed/21501195|accessdate=5/30/2011}}</ref>]]
 == References ==