Streptomyces strains

Tetracyclines are produced by various Streptomyces strains and are extensively applied in human and veterinary medicine. They display a broad spectrum of antimicrobial activity in combination with low toxicity and can be applied orally. The most commonly prescribed tetracycline drugs are tetracycline itself and oxytetracycline, an oxygenated derivative, which are directly isolated from fermentation liquors, and doxycycline whose partial synthesis from oxy-... 

S,3S)-Dicarboxyaziridine (112) was isolated from a Streptomyces strain in 1975 and found to have moderate antibacterial activity against Aeromonas salmonecida [176]. Subsequent studies showed that 112 acts as a competitive inhibitor of fumar-ase, through mimicry of a carbanionic transition state [177]. No biosynthetic studies have been reported for 112, but it is conceivable that it may arise from cydiza-tion of (3R)-hydroxyaspartic acid (Figure 11.18). 

Lutz-Wahl S, P Fischer, C Schmidt-Dannert, W Wohlleben, B Hauer, RD Schmid (1998) Stereo- and regio-selective hydroxylation of a-ionone by Streptomyces strains. Appl Environ Microbiol 64 3878-3881. 

Chun, J. Atalan, E. Ward, A. C. Goodfellow, M. Artificial neural network analysis of pyrolysis mass spectrometric data in the identification of Streptomyces strains. FEMS Microbiol. Lett. 1993,107,321-325. 

Streptomyces strains are Gram positive [54], they have good secretion capacities and extensive fermentation knowledge has been accumulated. Mostly, they were used for the production of secondary metabolites with potent biological activities, such as antibiotics, immunosuppressors or pesticides. Constitutive [55] and inducible [56] expression is possible. Up to 40% of the total soluble cellular protein was reported in the case of inducible expression. 

Traditionally, the majority of the studies in this area have emphasized the analysis of microorganisms, in particular of soil actinomycetes, as the most relevant source of potential herbicide agents. The plant kingdom, however, has also been explored for the discovery of new herbicides. So far, bialaphos, originally isolated from different Streptomyces strains, is the only commercial herbicide derived from a microbial source. On the other hand, cymethylin, an analog of the mono terpenoid 1,8-cineole, as well as... 

Two Streptomyces strains, S. badius and S. viridosporus, were found to be able to grow on kraft lignin (In-dulin ATR) as sole carbon source. The resulting APPL (Acid Precipitable Polymeric Lignin) was characterized by FTIR and elemental analysis for C, H and N, and was found to contain proteins in addition to a relatively demethoxylated lignin component. The proteins were further characterized by amino acid analysis, while the lignin component was separated by solvent extraction and its molecular weight distribution determined by HPSEC. 

Gabosines which have been isolated from Streptomyces strains constitute a family of keto carbasugars, most of them possessing a trihydroxylated cyclohexenone structure. Because of their interesting bioactivities, a large number of synthetic approaches to these compounds have been proposed (for example [115, 116]). The shortest route (four to five steps) to gabosines I and G was accomplished starting... 

Thirty percent of 500 marine Streptomyces strains showed interesting properties in some respect. From 100 selected strains more than 50 new compounds were isolated in a previous project. Their structural diversity, however, was similar to that from terrestrial sources. 

Diazaquinomycin A 123 is a natural antibacterial agent isolated from a Streptomyces strain and has been synthesized by Avendafio and co-workers <1998TL673> (for previous syntheses, see <1996CHEC-II(7)921>). 6-Azapinanaomycin A methyl ester 124 and 6-azaeleutherin 125 have been shown to be effective antibiotics <1997S567>. 

Renin inhibitors have been found among naturally occurring phospholipids and synthetic phosphatidylethanolamine derivatives. Pepstatin (5.131), isolated from Streptomyces strains, is a pentapeptide with an acylated N-terminus and the unusual 4-amino-3-hydroxy-6-methylheptanoic acid (AHMH) residues. It is a general protease... 

A large number of a, 3-didehydro-a-amino acids have been identified as constituents of relatively low molecular weight cyclic compounds from microbial sources. However, the presence of a,p-didehydroalanine in bacterial as well as in mammalian histidine ammonia lyase and in phenylalanine ammonia lyase shows that the occurrence of a,p-didehydro-a-amino acids is not limited to small molecules alone 8 These residues are incorporated in natural sequences by posttranslation modification. a,p-Didehydro-a-amino acids have also been postulated to be precursors in the biosynthesis of several heterocyclic metabolites including penicillin and cephalosporin 9 Other well-known compounds containing ,( -di-dehydro-a-amino acids are nisin 10,11 (a food preservative112 ), subtilin (a broad spectrum antibiotic) 13 and some of the metabolites isolated from Streptomyces strains such as gri-seoviridin 14 ... 

Sulfamoyl-2-chloroadenosine (121) from a strain of Streptomyces alhus possesses potent herbicidal activity on broad leaf weeds in post-emergent application (80 percent control on Sinapis alba, Stellaria media, Veronica persica, and Xanthium spinosum at <24 g/acre). Unfortunately, this compound also exhibits strong mammalian toxicity (LCso in mouse fibroblasts 0.013 pg/ml). Nucleocidin glucoside (122), a fluoronucleoside from a Streptomyces strain, is a weak herbicide [97]. 

The antimicrobial napyradiomycins A (192) and B (193) produced by a Streptomyces strain have been shown to be estrogen-receptor antagonists [154]. 

A Streptomyces strain isolated from Brazilian (Maytenus aquifolia) and South African (Putterlickia retrospinosa, Putterlickia verrucosa) plants has furnished celastramycin A (1212) (1225). A new isomer of the known rumbrin ( ) was isolated from an Australian soil ascomycete, Gymnoascus reessii, and named (12 ,)-isorumbrin (1213) (1226). Somewhat earlier, the three related auxarconju-gatins A, B, and (3 Z)-A (1214-1216) were characterized from an Arizona soil microorganism Auxarthron conjugatum (1227). A basidiomycete fungus from a New Zealand forest, Chamonixia pachydermis, produces pachydermin (1217) (1228). 

A novel ansamycin, naphthomycin K (1641), was isolated from a Streptomyces strain of the medicinal plant Maytenus hookeri (1616). This compound was cytotoxic (P388 and A-549 cell lines) but inactive against Staphylococcus aureus and Mycobacterium tuberculosis. An Amycolatopsis sp. has furnished the ansacarbami-tocins A-F, Al, B1 (1642-1649), which are similar to the ansamitocins (1617). 

Isomarinone (1679), an isomer of the previously known marinone (7), was isolated from the same tropical sediment bacterium (1638). Another marine-derived bacterium related to the genus Streptomyces has yielded the novel azamerone (1680) (1639). The British Columbian medicinal plant Moneses uniflora contains the antibiotic 8-chlorochimaphilin (1681), which is more active than chimaphilin (1640). Sesame roots (Sesamum indicum) have yielded the red chlorinated naphthoquinone chlorosesamone (1682) (1641). Cultures of Streptomyces strain LL-A9227 produce chloroquinocin (1683), which has some antibacterial activity against Gram-positive bacteria (1642). The two xestoquinones 1684 and 1685 were characterized from the Philippino sponge Xestospongia sp., and display topoisomerase II activity (1643). 

The Streptomyces strain that produces celastramycin A (1212) has also yielded celastramycin B (2166) (1225). Another Streptomyces sp. has afforded bischloro-anthrabenzoxocinone ((-)-BABX) (2167), which has antibacterial activity and inhibits ligand-binding activity of liver X receptors (1937). An example of a rare chlorinated anthraquinone is anthrasesamone C (2168), which was characterized in the Japanese plant Sesamum indicum (1938). The angucycline-type marmycin B... 

Baur S, Niehaus J. Karagouni AD, Katsifas EA, Chalkou K, Meintanis C, Jones AL, Goodfellow M, Ward AC, Beil W, Schneider K, Siissmuth RD, Fiedler H-P (2006) Fluostatins C-E, Novel Members of the Fluostatin Family Produced by Streptomyces Strain Acta 1383. J Antibiot 59 293... 

Pullen C, Schmitz P, Meurer K, Bamberg DD, Lohmann S, De Castro Franca S, Groth I, Schlegel B, Mollmann U, Gollmick F, Grafe U, Leistner E (2002) New and Bioactive Compounds from Streptomyces Strains Residing in the Wood of Celastraceae. Planta 216 162... 

Li S-M, Heide L (2005) New Aminocoumarin Antibiotics from Genetically Engineered Streptomyces Strains. Curr Med Chem 12 419... 

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