Actinorhodin

Actinorhodin
Names
	IUPAC name [3'-carboxymethyl-5,5',10,10'-tetrahydroxy-1,1'-dimethyl-6,6',9,9'-tetraoxo-3,3',4,4'6,6'9,9'-octahydro-1H,1'H-8,8'-bi(benzo[g]isochromen)-3-yl]acetic acid[1]
Identifiers
CAS Number	1397-77-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	76401
ChEBI	CHEBI:2448 ;
ChemSpider	16735642 ;
KEGG	C06691;
PubChem CID	5280985;
	InChI InChI=1S/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33-34,39-40H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1 Key: VTIKDEXOEJDMJP-WYUUTHIRSA-N ; InChI=1/C32H26O14/c1-9-21-15(3-11(45-9)5-19(35)36)29(41)23-17(33)7-13(27(39)25(23)31(21)43)14-8-18(34)24-26(28(14)40)32(44)22-10(2)46-12(6-20(37)38)4-16(22)30(24)42/h7-12,33-34,39-40H,3-6H2,1-2H3,(H,35,36)(H,37,38)/t9-,10-,11+,12+/m1/s1 Key: VTIKDEXOEJDMJP-WYUUTHIRBL;
	SMILES OC(=O)C[C@@H]5CC=6C(=O)c4c(O)cc(c3cc(O)c2C(=O)C=1C[C@@H](CC(O)=O)O[C@H](C)C=1C(=O)c2c3O)c(O)c4C(=O)C=6[C@@H](C)O5;
Properties
Chemical formula	C32H26O14
Molar mass	634.54 g mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Actinorhodin is a benzoisochromanequinone polyketide antibiotic produced by Streptomyces coelicolor.^[2]^[3] The gene cluster responsible for actinorhodin production contains the biosynthetic enzymes and genes responsible for export of the antibiotic.^[4] The antibiotic also has the effect of being a pH indicator due to its pH-dependent color change.^[5]

References

↑ "Actinorhodin (CHEBI:2448)". EBI Small Molecule Database. 18 February 2008. Retrieved 9 February 2010.
↑ Magnolo SK, Leenutaphong DL, DeModena JA, et al. (May 1991). "Actinorhodin production by Streptomyces coelicolor and growth of Streptomyces lividans are improved by the expression of a bacterial hemoglobin". Bio/Technology. 9 (5): 473–6. doi:10.1038/nbt0591-473. PMID 1367312.
↑ Brian P, Riggle PJ, Santos RA, Champness WC (June 1996). "Global negative regulation of Streptomyces coelicolor antibiotic synthesis mediated by an absA-encoded putative signal transduction system". J. Bacteriol. 178 (11): 3221–31. PMC 178074. PMID 8655502.
↑ Tahlan, K; Ahn SK; Sing A; Bodnaruk TD; Willems AR; Davidson AR; Nodwell JR. (February 2007). "Initiation of actinorhodin export in Streptomyces coelicolor". Molecular Microbiology. 63: 951–961. doi:10.1111/j.1365-2958.2006.05559.x. PMID 17338074.
↑ Bystrykh, LV; Fernández-Moreno MA; Herrema JK; Malpartida F; Hopwood DA; Dijkhuizen L (April 1996). "Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2)". Journal of Bacteriology. 178: 2238–44. PMC 177931. PMID 8636024.

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[ebi-1] "Actinorhodin (CHEBI:2448)". EBI Small Molecule Database. 18 February 2008. Retrieved 9 February 2010.

[pmid1367312-2] Magnolo SK, Leenutaphong DL, DeModena JA, et al. (May 1991). "Actinorhodin production by Streptomyces coelicolor and growth of Streptomyces lividans are improved by the expression of a bacterial hemoglobin". Bio/Technology. 9 (5): 473–6. doi:10.1038/nbt0591-473. PMID 1367312.

[pmid8655502-3] Brian P, Riggle PJ, Santos RA, Champness WC (June 1996). "Global negative regulation of Streptomyces coelicolor antibiotic synthesis mediated by an absA-encoded putative signal transduction system". J. Bacteriol. 178 (11): 3221–31. PMC 178074. PMID 8655502.

[Tahlan-4] Tahlan, K; Ahn SK; Sing A; Bodnaruk TD; Willems AR; Davidson AR; Nodwell JR. (February 2007). "Initiation of actinorhodin export in Streptomyces coelicolor". Molecular Microbiology. 63: 951–961. doi:10.1111/j.1365-2958.2006.05559.x. PMID 17338074.

[Bystrykh-5] Bystrykh, LV; Fernández-Moreno MA; Herrema JK; Malpartida F; Hopwood DA; Dijkhuizen L (April 1996). "Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2)". Journal of Bacteriology. 178: 2238–44. PMC 177931. PMID 8636024.