Actinomadura madurae

Madurastatins A1 (119 Scheme 11.17), A2 (120), A3 (121), B1 (122), and B2 (123) were isolated in 2004 from a clinical isolate of a pathogenic actinomycete, a strain of Actinomadura madurae [189]. The stereochemistry of the N-methyl-N-hydrox-yornithine residue remains unknown, but it was determined that the serine and aziridine residues are D, and the rest are L. 

Van Lanen, S.G., Oh, T.J., Liu, W. et al. (2007) Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis. Journal of the American Chemical Society, 129, 13082. 

Desferrimaduraferrin is a Fe " complexing metabolite of Actinomadura madurae 185). It consists of salicylic acid, p-Ala, Gly, L-Ser and 77 -hydroxy-77 -methyl-L-Om, with the latter incorporated in a heterocyclic system (Fig. 4, 13). From the same species the madurastatin group was obtained 136). The main representative A1 shows the sequence salicylic acid, o-azaridine carboxylic acid, L-Ala, p-Ala, 77 -hydroxy-77 -methyl-Om, L-cOHOm (Fig. 4, 14). In A2 the azaridine ring is opened giving a Ser residue, A3 is an isomer of the open form with the salicylic acid bound to the hydroxy group of Ser. B1 and B2 are the precursors A-salicyloyl-azaridine carboxylic acid and A-salicyloyl-Ser. The madurastatin species A1 forms a 1 1 Fe " complex as shown by mass spectrometry. 

Hantke K, Nicholson G. Rabsch W, Winkelmann G (2003) Salmochelins, Siderophores of Salmonella enterica and Uropathogenic Escherichia coli Strains, are Recognized by the Outer Membrane Receptor Iron. Proc Natl Acad Sci USA 100 3677 Harada K, Tomita K, Fuji K, Masuda K, Mikami Y, Yazawa K, Komaki H (2004) Isolation and Structural Characterization of Siderophores, Madurastatins, Produced by a Pathogenic Actinomadura madurae. J Antibiot 57 125... 

S. staurosporeus Anaya Actinomadura madurae A. melliaura Arcyria denudata Aspergillus flavus A. tubingensis Nocardia aerocoligenes Nocardiopsis dassonvillei Nocardiopsis sp. 

In 1997, Seto et al. reported the isolation of the novel neuronal protecting substances, carbazomadurin A (256) and carbazomaduiin B (257) from Actinomadura madurae 2808-SVl. Carbazomadurin B (257) was isolated from Nature in optically active form [a]p -I- 4.0 (c 0.05, MeOH). However, the absolute configuration was not determined (229) (Scheme 2.63). 

The previously known kedarcidin chromophore (7) is revised to CCC (7559), and the mechanism of action of this enediyne has been studied (1560). The new maduropeptin chromophore 1601 was isolated from Actinomadura madurae, which is associated with a protein of 14 amino acids (1561-1563). The non-protein associated enediyne N1999A2 (1602) was characterized from Streptomyces sp. AJ 9493 (1564), and confirmed by synthesis (1565,1566). 

Maduropeptin (MDP) 17, isolated in 1991 from the broth filtrate of Actinomadura madurae, consists of a 1 1 complex of an acidic water-soluble carrier apoprotein (32 kDa) and a labile enediyne chromophore, and showed potent antibacterial and antitumor activities [7]. The MDP apoprotein represented at that time a new protein class showing no sequence homology to the related chromoproteins neocarzistatin, auromomycin, actinoxanthin, C-1027, or kedarcidin, which were all in the 11.5-kDa... 

Harada, K. L, Tomita, K., Fujii, K., Masuda, K., Mikami, Y., Yazawa, K. and Komaki, H. 2004. Isolation and structure characterization of siderophore, madurastatins produced by a pathogenic Actinomadura madurae. J. Antibiot. 57 125-135. 

Actinomadura madurae, 986, 988 Activated charcoal, 3329 Activities of daily living (ADL), 1253 Acute pain, 1379... 

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