Novel Bioactive Oxazolomycin Isomers Produced by Streptomyces albus JA3453.

Kanzaki, Hiroshi; Wada, Ken Ichi; Nitoda, Teruhiko; Kawazu, Kazuyoshi

doi:10.1271/bbb.62.438

Cited by 41 publications

(48 citation statements)

References 5 publications

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“…Therefore, antioxidant agents may also play a role in the regulation of growth and the composition of biofilms in H. panicea. Phytotoxic compounds and algicides may prevent the sponge from periphyton algae (53,104). An example of such a substance is oxazolomycin (produced by strain HB100).…”

Section: Discussionmentioning

confidence: 99%

Comprehensive Investigation of Marine Actinobacteria Associated with the Sponge Halichondria panicea

Schneemann

Nagel

Kajahn

et al. 2010

Appl Environ Microbiol

101

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Representatives of Actinobacteria were isolated from the marine sponge Halichondria panicea collected from the Baltic Sea (Germany). For the first time, a comprehensive investigation was performed with regard to phylogenetic strain identification, secondary metabolite profiling, bioactivity determination, and genetic exploration of biosynthetic genes, especially concerning the relationships of the abundance of biosynthesis gene fragments to the number and diversity of produced secondary metabolites. All strains were phylogenetically identified by 16S rRNA gene sequence analyses and were found to belong to the genera Actinoalloteichus, Micrococcus, Micromonospora, Nocardiopsis, and Streptomyces. Secondary metabolite profiles of 46 actinobacterial strains were evaluated, 122 different substances were identified, and 88 so far unidentified compounds were detected. The extracts from most of the cultures showed biological activities. In addition, the presence of biosynthesis genes encoding polyketide synthases (PKSs) and nonribosomal peptide synthetases (NRPSs) in 30 strains was established. It was shown that strains in which either PKS or NRPS genes were identified produced a significantly higher number of metabolites and exhibited a larger number of unidentified, possibly new metabolites than other strains. Therefore, the presence of PKS and NRPS genes is a good indicator for the selection of strains to isolate new natural products.Sponges are multicellular invertebrates and sessile filter feeders which are abundant in the oceans as well as in freshwater habitats (41). They gained great interest due to their association with a wide variety of microorganisms. These microorganisms are known to be a rich source of secondary metabolites (108), which exhibit a broad range of bioactivities such as inhibition of enzyme activities and cell division and antiviral, antimicrobial, anti-inflammatory, antitumor, cytotoxic, and cardiovascular properties (77).Numerous studies concerning specific aspects of spongebacterium associations were accomplished using distinct methods for the evaluation of the microbial diversity (mostly molecular approaches) or the bioactivities (culture-dependent methods) or biosynthetic aspects (chemical analyses and molecular approaches) of secondary metabolites of the associated bacteria (19,47,51,54,110,122,126). So far, there is less comprehensive information about the integration of this knowledge into concepts for sponge-bacterium interactions based on small molecules.We focused on Actinobacteria associated with Halichondria panicea Pallas (Porifera, Demospongiae, Halichondriida, Halichondriidae), a sponge species living in coastal habitats worldwide (9). Previous work demonstrated a phylogenetically diverse array of bacterial groups present in this sponge: representatives of Alphaproteobacteria, Betaproteobacteria, Gammaproteobacteria, Cytophaga/Flavobacteria, the Deinococcus group, low-GϩC-content Gram-positive bacteria, Actinobacteria, and Planctomycetales were identified by means of a genetic ...

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Section: Discussionmentioning

confidence: 99%

Comprehensive Investigation of Marine Actinobacteria Associated with the Sponge Halichondria panicea

Schneemann

Nagel

Kajahn

et al. 2010

Appl Environ Microbiol

101

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“…331 In addition to 199 and 207, several further congeners were described (200)(201)(202)(203)(204)(205)(206)(208)(209)(210)(211)(212)(213)(214)(215)(216)(217). [332][333][334][335][336][337][338] Noteworthy is the occurrence of the structurally related clathrynamides 212-217 in the marine sponges Clathria sp. and Psammoclemma sp., 334,338 which indicates that a bacterium might be the true source.…”

Section: Macrolactinsmentioning

confidence: 99%

Biosynthesis of polyketides by trans-AT polyketide synthases

2010

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“…This vegetative culture was incubated at 28°C for about 60 hours on a shaker with a 2.5 cm throw and set at 250 rpm. The vegetative culture (10 ml aliquots) was used to inoculate 2 liter baffled flasks each containing 500 ml of sterile production medium prepared from glucose 10 g, glycerol 5 g, corn steep liquor 3 g, beef extract 3 g, malt extract 3 g, yeast extract 3 g, calcium carbonate 2 g, thiamine 0.1 g made up to one liter with distilled water [11]. The medium was adjusted at pH 7.0, and then 1 ml of silicon defoamer-oil (Chem Service) was added to each flask before sterilization.…”

Section: Genome Scanningmentioning

confidence: 99%

Genomic Analyses Lead to Novel Secondary Metabolites

et al. 2006

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Genomic analyses of Amycolatopsis orientalis ATCC 43491 strain, deposited as a vancomycin producer, revealed the presence of genetic loci for the production of at least 10 secondary metabolites other than vancomycin. One of these gene clusters, which contained a type I polyketide synthase, was predicted to direct the synthesis of novel class of compound, a glycosidic polyketide ECO-0501 (1). Screening of culture extracts for a compound with the predicted physicochemical properties of the product from this locus, led to the isolation of the 13-Oglucuronide of 13-hydroxy-2,12,14,16,22-pentamethyl-28-(N-methyl-guanidino)-octacosa-2,4,6,8,10,14,20,24-octaenoic acid (2-hydroxy-5-oxo-cyclopent-1-enyl)-amide (ECO-0501, 1). The structure, confirmed by spectral analyses including MS, and 1D and 2D NMR experiments, were in accord with that predicted by genomic analyses. ECO-0501 possessed strong antibacterial activity against a series of Gram-positive pathogens including several strains of methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci (VRE). ECO-0501 was chemically modified by esterification (1aϳ1c), Nacetylation (1d) and hydrogenation (1e) in order to explore structure activity relationships (SAR). Keywords Amycolatopsis orientalis, ECO-0501, antibacterial, PKS I IntroductionDrug-resistant bacterial infections are a growing health concern. Resistance has been developed to every major class of antibiotics on the market, and an increasing number of pathogenic bacteria are becoming resistant to multiple classes of antibiotics, thereby limiting treatment options. Hence, there is a renewed urgency for the discovery of new classes of antibiotics for the treatment of drug resistant bacterial infections. To accelerate the discovery of such potential antibacterial candidates from natural resources a new, fast and efficient technology is needed. The genomics of secondary metabolite biosynthesis recently evolved to the point where analysis of the genome of an organism can define its biosynthetic capabilities for secondary metabolites. A genome scanning technique that has been developed in our laboratories, and used with our DECIPHER ® technology to analyze the genomes of actinomycetes for their secondary metabolite biosynthetic genes, greatly reduces the amount of sequencing required to define this capability [1,2]. This approach not only ascertains the potential of a producing organism, but it provides a handle to detect, isolate and structurally define a specific metabolite. We have demonstrated this approach in the isolation and structural determination of an antifungal Genomic Analyses Lead to Novel Secondary MetabolitesPart 3

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Novel Bioactive Oxazolomycin Isomers Produced by Streptomyces albus JA3453.

Cited by 41 publications

References 5 publications

Comprehensive Investigation of Marine Actinobacteria Associated with the Sponge Halichondria panicea

Comprehensive Investigation of Marine Actinobacteria Associated with the Sponge Halichondria panicea

Biosynthesis of polyketides by trans-AT polyketide synthases

Genomic Analyses Lead to Novel Secondary Metabolites

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