アクチノロージン

アクチノロージン
	IUPAC名 [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]
識別情報
CAS登録番号	1397-77-9
ChemSpider	16735642
ChEBI	CHEBI:2448 ;
	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;
	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;
特性
モル質量	634.54 g mol-1
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

アクチノロージン(Actinorhodin)は、Streptomyces coelicolorが生産するベンゾイソクロマンキノン系のポリケチド抗生物質である[2][3]。アクチノロージンの生産に関与する遺伝子クラスターは、生合成酵素と、抗生物質の輸送を担う遺伝子を含む[4]。この抗生物質は、pHに依存して色が変わるため、酸塩基指示薬としての効果も持つ[5]。

出典

“Actinorhodin (CHEBI:2448)”. EBI Small Molecule Database (2008年2月18日). 2010年2月9日閲覧。
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”. Biotechnology (N.Y.) 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; Fernandez-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. PMID 8636024.

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[ebi-1] “Actinorhodin (CHEBI:2448)”. EBI Small Molecule Database (2008年2月18日). 2010年2月9日閲覧。

[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”. Biotechnology (N.Y.) 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; Fernandez-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. PMID 8636024.