close all open/close all
Jump cluster list

Cluster information : Actinorhodin


close this sectionCompound

Entry nameActinorhodin
PKS TypeTypeII
Starter Unitmalonyl-CoA
Chain Length8
Sugar Unitnone
ClassificationBenzoisochromanequinone (BIQ)
ActivityAntibacterial
Organocatalysis
CompositionC32H26O14
Actinorhodin

close this sectionOriginal source


close this sectionPKS/NRPS Module

KS3..374
CLF2..360
ACP6..79

close this sectionReference

Nucleotide sequence and deduced functions of a set of cotranscribed genes of Streptomyces coelicolor A3(2) including the polyketide synthase for the antibiotic actinorhodin.
Fernandez-Moreno MA, Martinez E, Boto L, Hopwood DA, Malpartida F
[PMID: 1527048]J Biol Chem. 267 (1992) 19278-90
Transcriptional organization and regulation of an antibiotic export complex in the producing Streptomyces culture.
Caballero JL, Malpartida F, Hopwood DA
[PMID: 1716725]Mol Gen Genet. 228 (1991) 372-80
Organisation and functions of the actVA region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor.
Caballero JL, Martinez E, Malpartida F, Hopwood DA
[PMID: 1766437]Mol Gen Genet. 230 (1991) 401-12
The act cluster contains regulatory and antibiotic export genes, direct targets for translational control by the bldA tRNA gene of Streptomyces.
Fernandez-Moreno MA, Caballero JL, Hopwood DA, Malpartida F
[PMID: 1878971]Cell. 66 (1991) 769-80
Biosynthesis of anthraquinones by interspecies cloning of actinorhodin biosynthesis genes in streptomycetes: clarification of actinorhodin gene functions.
Bartel PL, Zhu CB, Lampel JS, Dosch DC, Connors NC, Strohl WR, Beale JM Jr, Floss HG
[PMID: 2394677]J Bacteriol. 172 (1990) 4816-26
Nucleotide sequence, transcription and deduced function of a gene involved in polyketide antibiotic synthesis in Streptomyces coelicolor.
Hallam SE, Malpartida F, Hopwood DA
[PMID: 2469622]Gene. 74 (1988) 305-20
Identification of a flavin:NADH oxidoreductase involved in the biosynthesis of actinorhodin. Purification and characterization of the recombinant enzyme.
Kendrew SG, Harding SE, Hopwood DA, Marsh EN
[PMID: 7615536]J Biol Chem. 270 (1995) 17339-43
Stationary-phase production of the antibiotic actinorhodin in Streptomyces coelicolor A3(2) is transcriptionally regulated.
Gramajo HC, Takano E, Bibb MJ
[PMID: 7683365]Mol Microbiol. 7 (1993) 837-45
DNA sequence and functions of the actVI region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor A3(2).
Fernandez-Moreno MA, Martinez E, Caballero JL, Ichinose K, Hopwood DA, Malpartida F
[PMID: 7929165]J Biol Chem. 269 (1994) 24854-63
Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2).
Bystrykh LV, Fernandez-Moreno MA, Herrema JK, Malpartida F, Hopwood DA, Dijkhuizen L
[PMID: 8636024]J Bacteriol. 178 (1996) 2238-44
Identification of a monooxygenase from Streptomyces coelicolor A3(2) involved in biosynthesis of actinorhodin: purification and characterization of the recombinant enzyme.
Kendrew SG, Hopwood DA, Marsh EN
[PMID: 9209048]J Bacteriol. 179 (1997) 4305-10
Proof that the ACTVI genetic region of Streptomyces coelicolor A3(2) is involved in stereospecific pyran ring formation in the biosynthesis of actinorhodin.
Ichinose K, Surti C, Taguchi T, Malpartida F, Booker-Milburn KI, Stephenson GR, Ebizuka Y, Hopwood DA
[PMID: 10091691]Bioorg Med Chem Lett. 9 (1999) 395-400
A chain initiation factor common to both modular and aromatic polyketide synthases.
Bisang C, Long PF, Cortes J, Westcott J, Crosby J, Matharu AL, Cox RJ, Simpson TJ, Staunton J, Leadlay PF
[PMID: 10519556]Nature. 401 (1999) 502-5
Mechanistic analysis of a type II polyketide synthase. Role of conserved residues in the beta-ketoacyl synthase-chain length factor heterodimer.
Dreier J, Khosla C
[PMID: 10684659]Biochemistry. 39 (2000) 2088-95
Chemical characterisation of disruptants of the Streptomyces coelicolor A3(2) actVI genes involved in actinorhodin biosynthesis.
Taguchi T, Itou K, Ebizuka Y, Malpartida F, Hopwood DA, Surti CM, Booker-Milburn KI, Stephenson GR, Ichinose K
[PMID: 10805574]J Antibiot (Tokyo). 53 (2000) 144-52
Genetic Contributions to Understanding Polyketide Synthases.
Hopwood DA
[PMID: 11851466]Chem Rev. 97 (1997) 2465-2498
Primary and secondary metabolism, and post-translational protein modifications, as portrayed by proteomic analysis of Streptomyces coelicolor.
Hesketh AR, Chandra G, Shaw AD, Rowland JJ, Kell DB, Bibb MJ, Chater KF
[PMID: 12421300]Mol Microbiol. 46 (2002) 917-32
An antibiotic factory caught in action.
Keatinge-Clay AT, Maltby DA, Medzihradszky KF, Khosla C, Stroud RM
[PMID: 15286722]Nat Struct Mol Biol. 11 (2004) 888-93
The crystal structure of the actIII actinorhodin polyketide reductase: proposed mechanism for ACP and polyketide binding.
Hadfield AT, Limpkin C, Teartasin W, Simpson TJ, Crosby J, Crump MP
[PMID: 15458634]Structure. 12 (2004) 1865-75
Remarkably different structures and reaction mechanisms of ketoreductases for the opposite stereochemical control in the biosynthesis of BIQ antibiotics.
Taguchi T, Kunieda K, Takeda-Shitaka M, Takaya D, Kawano N, Kimberley MR, Booker-Milburn KI, Stephenson GR, Umeyama H, Ebizuka Y, Ichinose K
[PMID: 15498668]Bioorg Med Chem. 12 (2004) 5917-27
Transcriptional activation of the pathway-specific regulator of the actinorhodin biosynthetic genes in Streptomyces coelicolor.
Uguru GC, Stephens KE, Stead JA, Towle JE, Baumberg S, McDowall KJ
[PMID: 16164554]Mol Microbiol. 58 (2005) 131-50
Self-malonylation is an intrinsic property of a chemically synthesized type II polyketide synthase acyl carrier protein.
Arthur CJ, Szafranska A, Evans SE, Findlow SC, Burston SG, Owen P, Clark-Lewis I, Simpson TJ, Crosby J, Crump MP
[PMID: 16285746]Biochemistry. 44 (2005) 15414-21
Possible involvement of ActVI-ORFA in transcriptional regulation of actVI tailoring-step genes for actinorhodin biosynthesis.
Taguchi T, Okamoto S, Lezhava A, Li A, Ochi K, Ebizuka Y, Ichinose K
[PMID: 17227452]FEMS Microbiol Lett. 269 (2007) 234-9
Initiation of actinorhodin export in Streptomyces coelicolor.
Tahlan K, Ahn SK, Sing A, Bodnaruk TD, Willems AR, Davidson AR, Nodwell JR
[PMID: 17338074]Mol Microbiol. 63 (2007) 951-61
Actinorhodin biosynthesis: structural requirements for post-PKS tailoring intermediates revealed by functional analysis of ActVI-ORF1 reductase.
Itoh T, Taguchi T, Kimberley MR, Booker-Milburn KI, Stephenson GR, Ebizuka Y, Ichinose K
[PMID: 17579485]Biochemistry. 46 (2007) 8181-8
Investigation of transcription repression and small-molecule responsiveness by TetR-like transcription factors using a heterologous Escherichia coli-based assay.
Ahn SK, Tahlan K, Yu Z, Nodwell J
[PMID: 17644591]J Bacteriol. 189 (2007) 6655-64
Dissecting the component reactions catalyzed by the actinorhodin minimal polyketide synthase.
Beltran-Alvarez P, Cox RJ, Crosby J, Simpson TJ
[PMID: 18034463]Biochemistry. 46 (2007) 14672-81
Inhibition kinetics and emodin cocrystal structure of a type II polyketide ketoreductase.
Korman TP, Tan YH, Wong J, Luo R, Tsai SC
[PMID: 18205400]Biochemistry. 47 (2008) 1837-47
Crystal structures of the Streptomyces coelicolor TetR-like protein ActR alone and in complex with actinorhodin or the actinorhodin biosynthetic precursor (S)-DNPA.
Willems AR, Tahlan K, Taguchi T, Zhang K, Lee ZZ, Ichinose K, Junop MS, Nodwell JR
[PMID: 18207163]J Mol Biol. 376 (2008) 1377-87
Mechanism and regulation of the Two-component FMN-dependent monooxygenase ActVA-ActVB from Streptomyces coelicolor.
Valton J, Mathevon C, Fontecave M, Niviere V, Ballou DP
[PMID: 18245777]J Biol Chem. 283 (2008) 10287-96
Localization of the ActIII actinorhodin polyketide ketoreductase to the cell wall.
Xu XP, Wang ZJ, Fan KQ, Wang SL, Jia CJ, Han H, Ramalingam E, Yang KQ
[PMID: 18691223]FEMS Microbiol Lett. 287 (2008) 15-21
Ligand recognition by ActR, a TetR-like regulator of actinorhodin export.
Tahlan K, Yu Z, Xu Y, Davidson AR, Nodwell JR
[PMID: 18804114]J Mol Biol. 383 (2008) 753-61
Biosynthesis of actinorhodin and related antibiotics: discovery of alternative routes for quinone formation encoded in the act gene cluster.
Okamoto S, Taguchi T, Ochi K, Ichinose K
[PMID: 19246012]Chem Biol. 16 (2009) 226-36
Biosynthesis of aromatic polyketides in bacteria.
Das A, Khosla C
[PMID: 19292437]Acc Chem Res. 42 (2009) 631-9
Probing the Interactions of early polyketide intermediates with the Actinorhodin ACP from S. coelicolor A3(2).
Evans SE, Williams C, Arthur CJ, Ploskon E, Wattana-amorn P, Cox RJ, Crosby J, Willis CL, Simpson TJ, Crump MP
[PMID: 19361520]J Mol Biol. 389 (2009) 511-28
Preliminary kinetic analysis of acyl carrier protein-ketoacylsynthase interactions in the actinorhodin minimal polyketide synthase.
Beltran-Alvarez P, Arthur CJ, Cox RJ, Crosby J, Crump MP, Simpson TJ
[PMID: 19381365]Mol Biosyst. 5 (2009) 511-8
Structural and biochemical analyses of regio- and stereospecificities observed in a type II polyketide ketoreductase.
Javidpour P, Korman TP, Shakya G, Tsai SC
[PMID: 21506596]Biochemistry. 50 (2011) 4638-49
Epoxyquinone formation catalyzed by a two-component flavin-dependent monooxygenase involved in biosynthesis of the antibiotic actinorhodin.
Taguchi T, Okamoto S, Hasegawa K, Ichinose K
[PMID: 22086671]Chembiochem. 12 (2011) 2767-73
Identification of the actinorhodin monomer and its related compound from a deletion mutant of the actVA-ORF4 gene of Streptomyces coelicolor A3(2).
Taguchi T, Ebihara T, Furukawa A, Hidaka Y, Ariga R, Okamoto S, Ichinose K
[PMID: 22765902]Bioorg Med Chem Lett. (2012)
A two-step mechanism for the activation of actinorhodin export and resistance in Streptomyces coelicolor.
Xu Y, Willems A, Au-Yeung C, Tahlan K, Nodwell JR
[PMID: 23073761]MBio. 3 (2012) e00191-12
Biosynthetic conclusions from the functional dissection of oxygenases for biosynthesis of actinorhodin and related streptomyces antibiotics.
Taguchi T, Yabe M, Odaki H, Shinozaki M, Metsa-Ketela M, Arai T, Okamoto S, Ichinose K
[PMID: 23601640]Chem Biol. 20 (2013) 510-20
The determinants of activity and specificity in actinorhodin type II polyketide ketoreductase.
Javidpour P, Bruegger J, Srithahan S, Korman TP, Crump MP, Crosby J, Burkart MD, Tsai SC
[PMID: 24035284]Chem Biol. 20 (2013) 1225-34
Modeling linear and cyclic PKS intermediates through atom replacement.
Shakya G, Rivera H Jr, Lee DJ, Jaremko MJ, La Clair JJ, Fox DT, Haushalter RW, Schaub AJ, Bruegger J, Barajas JF, White AR, Kaur P, Gwozdziowski ER, Wong F, Tsai SC, Burkart MD
[PMID: 25406716]J Am Chem Soc. 136 (2014) 16792-9
Structure and biosynthetic implication of 5R-(N-acetyl-L-cysteinyl)-14S-hydroxy-dihydrokalafungin from a mutant of the actVA-ORF4 gene for actinorhodin biosynthesis in Streptomyces coelicolor A3(2).
Taguchi T, Maruyama T, Sawa R, Igarashi M, Okamoto S, Ichinose K
[PMID: 25690356]J Antibiot (Tokyo). 68 (2015) 481-3
Highly efficient editing of the actinorhodin polyketide chain length factor gene in Streptomyces coelicolor M145 using CRISPR/Cas9-CodA(sm) combined system.
Zeng H, Wen S, Xu W, He Z, Zhai G, Liu Y, Deng Z, Sun Y
[PMID: 26318449]Appl Microbiol Biotechnol. 99 (2015) 10575-85

close this sectionData download

Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Actinorhodin
Genomic nucleotide sequence
24 KB
Nucleotide sequences of the coding regions
7 KB
Translation of the coding sequences
5 KB
List of genes/ORFs
1 KB

 

 
GenBank format
51 KB
X62373
Genomic nucleotide sequence
6 KB
Nucleotide sequences of the coding regions
5 KB
Translation of the coding sequences
2 KB
List of genes/ORFs
923 B

 

 

 
X58833
Genomic nucleotide sequence
5 KB
Nucleotide sequences of the coding regions
6 KB
Translation of the coding sequences
2 KB
List of genes/ORFs
875 B

 

 

 
M64683
Genomic nucleotide sequence
6 KB
Nucleotide sequences of the coding regions
6 KB
Translation of the coding sequences
2 KB
List of genes/ORFs
636 B

 

 

 
M19536
Genomic nucleotide sequence
1 KB
Nucleotide sequences of the coding regions
858 B
Translation of the coding sequences
315 B
List of genes/ORFs
252 B

 

 

 
X63449
Genomic nucleotide sequence
5 KB
Nucleotide sequences of the coding regions
6 KB
Translation of the coding sequences
2 KB
List of genes/ORFs
948 B

 

 

 

close this sectionHistory

  • 2016-12-27[Update]
  • 2016-01-27[Update]
  • 2013-12-27[Update]
  • 2013-05-28[Update]
  • 2013-01-16[Update]
  • 2012-10-02[Update]
  • 2012-08-03[Update]
  • 2012-06-04[Release]