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Search for "actinomycetes" in Full Text gives 28 result(s) in Beilstein Journal of Organic Chemistry.
Confirmation of the stereochemistry of spiroviolene
Beilstein J. Org. Chem. 2024, 20, 852–858, doi:10.3762/bjoc.20.77
- spiroviolene and spirograterpene A therefore indicated that there must exist two terpene cyclases of different origins (Actinomycetes and Fungus) that were able to carry out similar chemical processes for the formation of the intriguing 5-5-5-5 tetracyclic ring system. Also, our study supports the proposed
Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria
Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75
- been laterally transferred several times, within and among the Alphaproteobacteria, Betaproteobacteria, Deltaproteobacteria, and Actinomycetes lineages. The combined data suggest that NNG degradation activity is found in diverse bacteria. Additionally, these bacteria were isolated from geographically
Methodology for awakening the potential secondary metabolic capacity in actinomycetes
Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69
- drug discovery. However, it is becoming difficult to obtain novel compounds because of repeated isolation around the world. Therefore, a new strategy for discovering novel secondary metabolites is needed. Many researchers believe that actinomycetes have as yet unanalyzed secondary metabolic activities
- , and the associated undiscovered secondary metabolite biosynthesis genes are called “silent” genes. This review outlines several approaches to further activate the metabolic potential of actinomycetes. Keywords: actinomycete; co-culture; heat shock metabolites (HSMs); secondary metabolites; silent
- actinomycetes. Secondary metabolites produced by actinomycetes, representing a class of compounds with a diverse chemical space, have promising potential as sources of bioactive substances [10]. Due to his discovery of streptomycin from Streptomyces griseus, Waksman was awarded the Nobel Prize in Physiology and
A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001
Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44
- Actinomycetes are well-known as the main producers of bioactive compounds such as antibiotics, anticancers, and immunosuppressants. Screening of natural products from actinomycetes has been an essential part of several drug discovery programs. Finding such novel biologically active metabolites is immensely
- important because of their beneficial health effects. Recently, the discovery of new compounds has diverted attention to rare actinomycetes, since they are rich sources of natural products. In this study, a collection of rare actinomycetes at Kitasato University has been screened for potential novel
- compound producers. Among the rare actinomycetes, Saccharopolyspora sp. KR21-0001 isolated from soil on Ōha Island, Okinawa, Japan was selected as a potential producer. The strain was cultured in 20 L of production medium in a jar fermenter and the culture broth was extracted. Further purification revealed
Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway
Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1
- the presence of more than 100 ava cluster-related biosynthetic gene clusters (BGCs) in actinomycetes; however, their functions remained unclear. In this study, we focused on an ava cluster-related BGC in Kutzneria albida (cma cluster), and revealed that it is responsible for p-coumaric acid
- -dependent deamination pathway for the production of avenalumic acid or p-coumaric acid. Keywords: actinomycetes; avenalumic acid; biosynthesis; p-coumaric acid; polyketides; Introduction The genomes of microorganisms possess diverse biosynthetic gene clusters (BGCs) to produce natural products [1]. In
- particular, actinomycetes, a major source of bioactive compounds, have numerous BGCs in their genomes, but the majority of them are thought to be silent under laboratory conditions [2]. Because these orphan BGCs are often related to the production of unknown natural products, genome mining has been
Functional characterisation of twelve terpene synthases from actinobacteria
Beilstein J. Org. Chem. 2023, 19, 1386–1398, doi:10.3762/bjoc.19.100
- phylogenetically related enzymes were in one case not expressed and in two cases inactive, suggesting pseudogenisation in the respective branch of the phylogenetic tree. Furthermore, a diterpene synthase for allokutznerene and a sesterterpene synthase for sesterviolene were identified. Keywords: actinomycetes
- have been reported. Here, we report on the discovery and functional characterisation of four sesquiterpene synthases from actinomycetes with novel functions, in addition to several actinomycete terpene synthases for which functional homologs have been identified before. Results and Discussion
- related enzymes from other actinomycetes with a pairwise identity of 69% may also function as (+)-δ-cadinol synthases (Figure S11, Supporting Information File 1). The enzyme from S. jumonjiensis (Table 1, entry 2) showed the fully established conserved motifs including the aspartate-rich region (83DDVRSE
Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum
Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12
- attractive resource of new therapeutics, which are not found from terrestrial bioresources [4][5][6]. While a large majority of marine microbe-derived natural products are from fungi and actinomycetes, less attention has been paid to non-actinomycetal bacteria [6][7][8][9]. Particularly, secondary
Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes
Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203
- .17.203 Abstract A genome mining survey combined with metabolome analysis of publicly available strains identified Couchioplanes sp. RD010705, a strain belonging to an underexplored genus of rare actinomycetes, as a producer of new metabolites. HPLC-DAD-guided fractionation of its fermentation extracts
- were weakly inhibitory against Kocuria rhizophila at MIC 100 μg/mL and none were cytotoxic against P388 at the same concentration. Keywords: Couchioplanes; prenylated tryptophan; rare actinomycete; unsaturated fatty acid; Introduction Actinomycetes, a subgroup of filamentous Gram-positive bacteria
- within the class Actinomycetales, have provided many important clinical drugs [1][2], agrochemicals [3], food additives [4][5], and biochemical reagents [6][7][8][9], and continue to be a core source of bioactive molecules [10]. While most of the actinomycetes-derived compounds have been reported from
Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura
Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141
- cytotoxicity against P388 murine leukemia cells with IC50 values of 33 and 89 μM, respectively. Keywords: Actinomadura; nomimicin; polyketide; spirotetronate; Introduction Actinomycetes are a valuable source of bioactive compounds, accounting for approximately two thirds of all known antibiotics, and more
- than 70% of them are produced by the genus Streptomyces [1]. However, intensive and concentrated screening activities on soil actinomycetes resulted in the repeated isolation of known compounds [2], which consequently prompted the exploration of untouched niches, such as extreme environments [3]. The
- marine environment is now attracting attention as a promising source for actinomycetes potentially producing new secondary metabolites [4][5]. Indeed, a large number of pharmaceutically worthy new compounds has been found from marine actinomycetes in various niches including sediments, sea water, marine
Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of 1JC,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites
Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222
- [1]. More than 10,000 secondary metabolites have been isolated from actinomycetes, accounting for almost 45% of all known microbial secondary metabolites. Particularly, 70% of them were isolated from the genus Streptomyces, the dominant genus commonly found in terrestrial environments [2]. The number
- of new bioactive compounds from actinomycetes, especially those from terrestrial sources, is likely reaching a plateau after intensive screening activities over several decades [3]. Actinomycetes also inhabit marine environments, including seashores, coastal waters, and bottom sediments or can be
- found in association with marine organisms such as invertebrates and plants [4][5]. Marine actinomycetes show unique physiological adaptations distinct from their terrestrial counterparts in terms of pressure, salinity, or low-temperature tolerance, which might affect their metabolic ability in their
4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity
Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124
- emerging source of bioactive molecules. Many new structure classes, even after being spun off as a new genus from Pseudomonas in 1992 [14], have been discovered from this group, which, along with their large genomes comparable to those of actinomycetes or myxobacteria, demonstrate a higher capacity of
A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium
Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97
- , National Institute of Technology and Evaluation (NBRC), Kisarazu, Chiba 292-0818, Japan 10.3762/bjoc.16.97 Abstract Aside from the well-studied conventional actinomycetes such as Streptomyces, the less investigated genera of actinomycetes also represent a promising source of natural products. Genome
- discovery of new natural products. Keywords: DFT-based calculation; oligomycin; peptide; polyketides; Pseudosporangium; rare actinomycetes; Introduction Microbial secondary metabolites have been used as therapeutic drugs [1], veterinary medicines [2], agrochemicals [3], food preservatives/colorings [4][5
- actinomycetes” refers to non-Streptomyces actinomycetes [12] and the representative genera, such as Micromonospora, Actinomadura, Nocardia, Actinoplanes, and Saccharothrix, which are no longer rare in terms of difficulties in isolation, already provided thousands of new metabolites [13][14]. Meanwhile, the
Fabclavine diversity in Xenorhabdus bacteria
Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84
- actinomycetes and myxobacteria, the genera Photorhabdus and Xenorhabdus are promising sources to discover new SMs since up to 6.5% of their overall genome sequence are associated with SM biosynthesis [5][6]. This includes antimicrobials like isopropylstilbene, xenocoumacins, amicoumacin, and several other SMs
Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus
Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29
- strepchloritides [7], nahuoic acids B–E [8], and pteridic acids C–G [9], were obtained from actinobacteria associated with soft corals. There is no report indeed on natural products from actinobacteria residing in stony corals. Actinomycetes of the genus Micrococcus are Gram-positive, aerobic, and nonmotile cocci
- . Unlike the majority of actinomycetes, they typically form tetrad clusters but not hyphae [10]. Micrococcus is ubiquitous in distribution and, similar to other actinomycetes, marine Micrococcus are commonly associated with marine invertebrates, such as sponges and corals [4][11][12]. Distinct classes of
Two new aromatic polyketides from a sponge-derived Fusarium
Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289
- sponges in massive amounts leads to environmental disturbance since marine sponges play a key role in building coral reefs [3][4]. As a filter feeder, sponges host an enormous amount of microorganisms including algae, bacteria, actinomycetes, and fungi [5][6][7]. Many of these microorganisms produce
Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225
- the nucleophilic carbons originated from the methyl carbon of acetate (C2) since SAM acts as an electrophilic methyl donor. In most of the bacteria including actinomycetes, methyl branching in polyketide chain is derived from methylmalonyl CoA, thereby the methylation position must be also the α
Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides
Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174
- muramyl peptides induce significantly higher activation of NOD2 than MDP [29][30]. Mycobacteria present in complete Freund’s adjuvant, and related Actinomycetes, produce N-glycolyl MDP by the hydroxylase action on MDP (N-acetylmuramic acid within the peptidoglycan). The influence of structural
An overview of recent advances in duplex DNA recognition by small molecules
Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93
Volatiles from three genome sequenced fungi from the genus Aspergillus
Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77
- ][30], but geosmin could not be observed as a volatile of A. fischeri. The bacterial geosmin synthase is a class I terpene synthase (TS) with two domains [31] that occurs in many actinomycetes, cyanobacteria and myxobacteria, but fungal geosmin biosynthesis must require a different enzyme, because no
Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces
Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47
- valine and its C-methylation with methionine and the polyol carbons are derived from a glycolysis intermediate, possibly hydroxymalonyl-ACP. Keywords: biosynthesis; butyrolactol; contiguous polyol; hydroxymalonyl-ACP; polyketide; Streptomyces; tert-butyl; Introduction Actinomycetes produce structurally
- templates for new pharmacophores [3]. While the frequency of discovering new skeletons from actinomycetes seems declining, biosynthetic analysis of structurally unique known compounds and the following bioengineering of biosynthetic genes are currently becoming an essential part of the creation of new drug
- polyketide. Examples of similar but shorter polyol carbon chains are ossamycin [19], IB-96212 [20], and antifungalmycin [21], all of which are the secondary metabolites of actinomycetes (Figure 3). In our investigation on secondary metabolites of marine actinomycetes, butyrolactol A (1) was found to be
Mechanistic investigations on six bacterial terpene cyclases
Beilstein J. Org. Chem. 2016, 12, 1839–1850, doi:10.3762/bjoc.12.173
- ploughed earth. Only recent research revealed that terpenes are in fact widespread in bacteria, in particular in actinomycetes and a few other taxa that are actively engaged in secondary metabolism [7][8][9]. Since a couple of years the rapidly evolved genome sequencing techniques allow for a mining of
Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148
- heterocyclic compounds are produced by a range of actinomycetes and a deeper understanding of their biosynthesis was for a long time hampered by the inability to identify their biosynthetic genes. Those were finally discovered by a comparative genomics approach in which the clusters of thiolactomycin (165
Mycothiol synthesis by an anomerization reaction through endocyclic cleavage
Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35
- occurrence of multiple-drug-resistant (MDR), extensive-drug-resistant (EDR), and totally drug-resistant (TDR) pathogens has increased the need for new drug candidates for treating tuberculosis. Mycothiol (MSH) 1 is the main low-molecular-weight thiol found in most actinomycetes, including Mycobacteria and
- the cytosol. Gram-positive bacteria including actinomycetes lack glutathione, instead, MSH is found as the major low-molecular-weight thiol. It is considered that MSH is required for maintaining a reducing intracellular environment in Gram-positive bacteria, similar to glutathione in eukaryotes and
Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5
Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146
- that are accompanied by a broad range of headspace constituents that occur in many actinomycetes. Volatiles might be of ecological importance for the producing organism, and, as biosynthetic intermediates or shunt products, they can be useful as indicators of antibiotic production in a bacterium
- . Keywords: headspace analysis; natural products; polyketide biosynthesis; pyridine derivatives; streptazolin; volatile compounds; Introduction Actinomycetes are excellent producers of diverse and bioactive secondary metabolites. These metabolites belong to many different structural classes including
- polyketides, nonribosomal peptides, terpenoids, alkaloids, lipids and others. Such compounds became a major source of biologically active natural products as antibiotics, cytotoxic compounds, immunosuppressants etc. In addition, actinomycetes are also able to produce and release a wide variety of volatile
Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis
Beilstein J. Org. Chem. 2013, 9, 2767–2777, doi:10.3762/bjoc.9.311
- , but the overall trend is similar, and therefore chlorine and bromine are also the most widespread halogens in natural products from terrestrial organisms. Many biologically active halogenated secondary metabolites are known from actinomycetes including vancomycin [4], chloramphenicol [5], rebeccamycin
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