Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000824.1:
Cluster 1Alkaloid129254
The following clusters are from record BGC0000824.2:
Cluster 2Alkaloid15646

BGC0000824, scytonemin biosynthetic gene cluster from Nostoc punctiforme. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Scytonemin
ChEMBL ID: 505177
ChemSpider ID: 16736974
SMILES string: Copy to clipboard
Molecular formula: C36H22N2O4
Average molecular mass: 546.6 Da
Molecular activity: Other
Molecular target: polo-like kinase 1; protein kinase C

Class-specific details

Biosynthetic class(es):
Alkaloid
Alkaloid subclass:
Indole/benzopyrrole

Gene cluster description

scytonemin (BGC0000824). Gene Cluster 1. Biosynthetic class = Alkaloid. GenBank CP001037, positions 1514904-1544157. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Homologous known gene clusters

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Enzymatic assays, Gene expression correlated with compound production, Sequence-based prediction
MIxS-compliance:Unknown
Comments:The second genomic locus I listed for scytonemin biosynthesis involves 5 genes (Npun_F5232-Npun5236) that have been shown to be upregulated through cDNA analysis by UV light (as has the main scytonemin cluster) and are shown to be associated with the main scytonemin cluster in other cyanobacterial species but are separated from the scytonmein cluster in Nostoc. Also, the genes Npun_1277 and Npun_1278 are thought through sequence analysis to be involved in scytonemin biosynthesis, particularly signaling but are located on a different operon. These are included as part of the main scytonemin gene cluster however there is no experimental evidence to support this. All of the genes from Npun_R1260-Npun_R1276 have been shown through cDNA assays to be upregulated under UV light, a known key factor in the production of scytonemin.
Contact for this cluster:Carla S. Jones (Roosevelt University)

Literature references

1. Sorrels CM et al. (2009) Organization, evolution, and expression analysis of the biosynthetic gene cluster for scytonemin, a cyanobacterial UV-absorbing pigment. Appl Environ Microbiol 75(14):4861-9. doi: 10.1128/AEM.02508-08. Epub
2. Jones CS et al. (2011) Probing the in vivo biosynthesis of scytonemin, a cyanobacterial ultraviolet radiation sunscreen, through small scale stable isotope incubation studies and MALDI-TOF mass spectrometry. Bioorg Med Chem 19(22):6620-7. doi: 10.1016/j.bmc.2011.06.005. Epub
3. Balskus EP, Walsh CT. (2008) Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin. J Am Chem Soc 130(46):15260-1. doi: 10.1021/ja807192u. Epub 2008 Oct
4. Soule T et al. (2007) Molecular genetics and genomic analysis of scytonemin biosynthesis in Nostoc punctiforme ATCC 29133. J Bacteriol 189(12):4465-72. doi: 10.1128/JB.01816-06. Epub 2007 Mar 9.
5. Balskus EP, Walsh CT. (2009) An enzymatic cyclopentyl[b]indole formation involved in scytonemin biosynthesis. J Am Chem Soc 131(41):14648-9. doi: 10.1021/ja906752u.
6. Soule T et al. (2009) Gene expression patterns associated with the biosynthesis of the sunscreen scytonemin in Nostoc punctiforme ATCC 29133 in response to UVA radiation. J Bacteriol 191(14):4639-46. doi: 10.1128/JB.00134-09. Epub 2009 May 8.
7. Jones CS et al. (2011) Probing the in vivo biosynthesis of scytonemin, a cyanobacterial ultraviolet radiation sunscreen, through small scale stable isotope incubation studies and MALDI-TOF mass spectrometry. Bioorg Med Chem 19(22):6620-7. doi: 10.1016/j.bmc.2011.06.005. Epub
8. Soule T et al. (2009) A comparative genomics approach to understanding the biosynthesis of the sunscreen scytonemin in cyanobacteria. BMC Genomics 10:336. doi: 10.1186/1471-2164-10-336.
9. Balskus EP et al. (2011) The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities. FEMS Microbiol Ecol 77(2):322-32. doi:
10. Ekebergh A et al. (2011) Oxidative coupling as a biomimetic approach to the synthesis of scytonemin. Org Lett 13(16):4458-61. doi: 10.1021/ol201812n. Epub 2011 Jul 25.
11. Stevenson CS et al. (2002) The identification and characterization of the marine natural product scytonemin as a novel antiproliferative pharmacophore. J Pharmacol Exp Ther 303(2):858-66. doi: 10.1124/jpet.102.036350.
12. Garcia-Pichel F et al. (1992) Evidence for an ultraviolet sunscreen role of the extracellular pigment scytonemin in the terrestrial cyanobacterium Chlorogloeopsis sp. Photochem Photobiol 56(1):17-23.
13. Stevenson CS et al. (2002) Scytonemin--a marine natural product inhibitor of kinases key in hyperproliferative inflammatory diseases. Inflamm Res 51(2):112-4.
14. Proteau PJ et al. (1993) The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria. Experientia 49(9):825-9.

BGC0000824, scytonemin biosynthetic gene cluster from Nostoc punctiforme. Locus 2. Full MIBiG entry.

Chemical compounds

Compound: Scytonemin
ChEMBL ID: 505177
ChemSpider ID: 16736974
SMILES string: Copy to clipboard
Molecular formula: C36H22N2O4
Average molecular mass: 546.6 Da
Molecular activity: Other
Molecular target: polo-like kinase 1; protein kinase C

Class-specific details

Biosynthetic class(es):
Alkaloid
Alkaloid subclass:
Indole/benzopyrrole

Gene cluster description

scytonemin (BGC0000824). Gene Cluster 2. Biosynthetic class = Alkaloid. GenBank CP001037, positions 1514904-1544157. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Homologous known gene clusters

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Enzymatic assays, Gene expression correlated with compound production, Sequence-based prediction
MIxS-compliance:Unknown
Comments:The second genomic locus I listed for scytonemin biosynthesis involves 5 genes (Npun_F5232-Npun5236) that have been shown to be upregulated through cDNA analysis by UV light (as has the main scytonemin cluster) and are shown to be associated with the main scytonemin cluster in other cyanobacterial species but are separated from the scytonmein cluster in Nostoc. Also, the genes Npun_1277 and Npun_1278 are thought through sequence analysis to be involved in scytonemin biosynthesis, particularly signaling but are located on a different operon. These are included as part of the main scytonemin gene cluster however there is no experimental evidence to support this. All of the genes from Npun_R1260-Npun_R1276 have been shown through cDNA assays to be upregulated under UV light, a known key factor in the production of scytonemin.
Contact for this cluster:Carla S. Jones (Roosevelt University)

Literature references

1. Sorrels CM et al. (2009) Organization, evolution, and expression analysis of the biosynthetic gene cluster for scytonemin, a cyanobacterial UV-absorbing pigment. Appl Environ Microbiol 75(14):4861-9. doi: 10.1128/AEM.02508-08. Epub
2. Jones CS et al. (2011) Probing the in vivo biosynthesis of scytonemin, a cyanobacterial ultraviolet radiation sunscreen, through small scale stable isotope incubation studies and MALDI-TOF mass spectrometry. Bioorg Med Chem 19(22):6620-7. doi: 10.1016/j.bmc.2011.06.005. Epub
3. Balskus EP, Walsh CT. (2008) Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin. J Am Chem Soc 130(46):15260-1. doi: 10.1021/ja807192u. Epub 2008 Oct
4. Soule T et al. (2007) Molecular genetics and genomic analysis of scytonemin biosynthesis in Nostoc punctiforme ATCC 29133. J Bacteriol 189(12):4465-72. doi: 10.1128/JB.01816-06. Epub 2007 Mar 9.
5. Balskus EP, Walsh CT. (2009) An enzymatic cyclopentyl[b]indole formation involved in scytonemin biosynthesis. J Am Chem Soc 131(41):14648-9. doi: 10.1021/ja906752u.
6. Soule T et al. (2009) Gene expression patterns associated with the biosynthesis of the sunscreen scytonemin in Nostoc punctiforme ATCC 29133 in response to UVA radiation. J Bacteriol 191(14):4639-46. doi: 10.1128/JB.00134-09. Epub 2009 May 8.
7. Jones CS et al. (2011) Probing the in vivo biosynthesis of scytonemin, a cyanobacterial ultraviolet radiation sunscreen, through small scale stable isotope incubation studies and MALDI-TOF mass spectrometry. Bioorg Med Chem 19(22):6620-7. doi: 10.1016/j.bmc.2011.06.005. Epub
8. Soule T et al. (2009) A comparative genomics approach to understanding the biosynthesis of the sunscreen scytonemin in cyanobacteria. BMC Genomics 10:336. doi: 10.1186/1471-2164-10-336.
9. Balskus EP et al. (2011) The biosynthesis of cyanobacterial sunscreen scytonemin in intertidal microbial mat communities. FEMS Microbiol Ecol 77(2):322-32. doi:
10. Ekebergh A et al. (2011) Oxidative coupling as a biomimetic approach to the synthesis of scytonemin. Org Lett 13(16):4458-61. doi: 10.1021/ol201812n. Epub 2011 Jul 25.
11. Stevenson CS et al. (2002) The identification and characterization of the marine natural product scytonemin as a novel antiproliferative pharmacophore. J Pharmacol Exp Ther 303(2):858-66. doi: 10.1124/jpet.102.036350.
12. Garcia-Pichel F et al. (1992) Evidence for an ultraviolet sunscreen role of the extracellular pigment scytonemin in the terrestrial cyanobacterium Chlorogloeopsis sp. Photochem Photobiol 56(1):17-23.
13. Stevenson CS et al. (2002) Scytonemin--a marine natural product inhibitor of kinases key in hyperproliferative inflammatory diseases. Inflamm Res 51(2):112-4.
14. Proteau PJ et al. (1993) The structure of scytonemin, an ultraviolet sunscreen pigment from the sheaths of cyanobacteria. Experientia 49(9):825-9.