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Search for "metabolites" in Full Text gives 247 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.
Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97
- methodology is still not available. As of 2006, the family forms a sister taxon to the Omphalotaceae within the suborder of Marasmiineae (Agaricales) [2][3]. Among Basidiomycota, the Marasmiineae are most famous for their abundant chemical diversity. Metabolites with various bioactivities described from
- characterization. Results Structure elucidation of the secondary metabolites 2–6 Preparative HPLC of the supernatant crude extract of a submerged cultivation of Marasmius sp. strain MFLUCC 14-0681 in ZM½ media led to the isolation of six carotane sesquiterpenoids, fulvoferruginins A–F (1–6, Figure 1). The first
- fulvoferruginins A–F (1–6), aside from the known antifungal activity of fulvoferruginin (1), no other antimicrobial activities were observed (Table S2 in Supporting Information File 1). All metabolites were also tested against the murine fibroblast cell line L929 and the cervix carcinoma cell line KB3.1. While all
A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry
Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91
- distributions of metabolites and identifying specific symbiotic bacteria. Keywords: algae; AP-SMALDI; ectoine; holobiont; high-resolution mass spectrometry; mass spectrometry imaging; marine bacteria; Ulva; Introduction In intertidal zones with high temporal and spatial ecosystem variations, bacteria and
- specialised metabolites involved in host–bacteria interactions. In our study, comparative metabolomics using atmospheric pressure scanning microprobe matrix-assisted laser desorption/ionisation high-resolution mass spectrometry (AP-SMALDI-HRMS) enables the identification of specialised metabolites of the
- profile fingerprint matching [26][27][28]. Our research combines cutting-edge laser scanning microscopy and high-resolution mass spectrometry to uncover Ulva/bacteria interactions and specialised metabolites at the microscale level. In this study, we demonstrate that the chemosphere of U. mutabilis
Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols
Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52
- synthetic methods for secosteroids is wide. However, usually these are multistep sequences exploiting toxic oxidants. Marine invertebrates are a rich source of oxidated and highly functionalized steroidal metabolites, including secosteroids. Since the first isolation of 9,11-secosterol from
Synthetic strategies of phosphonodepsipeptides
Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41
- , indicating that this strategy was not suitable for the synthesis of γ-phosphonodepsipeptides (Scheme 13) [28]. Folylpolyglutamate synthetase catalyzes an ATP-dependent ligation reaction. The reaction results in the synthesis of poly(γ-glutamate) metabolites of folates and some antifolates. Three γ
Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement
Beilstein J. Org. Chem. 2021, 17, 439–460, doi:10.3762/bjoc.17.40
- changes and other types of stress. For example, in exponentially growing E. coli, the intracellular concentration of proline was determined as 3.9 × 10−4 mol⋅L−1. This data ranks proline as the 41st in the list of metabolites and as the 9th among the amino acids coded into proteins [60]. The two main
Identification of volatiles from six marine Celeribacter strains
Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38
- incorporation was observed for the other two sulfur atoms of 41 prompted us to further investigate the biosynthetic origin of the benzothiazol-2-ylsulfanyl portion of 41 to establish its natural origin. Several feeding experiments with central primary metabolites including (13C6)glucose, (13C5)ribose and
- by DddW, DddP, DddQ, DddL, DddY or DddK, and C) structures of DHPS and sulfur-containing secondary metabolites. Synthesis of sulfur-containing compounds detected in the Celeribacter headspace extracts. A) Synthesis of 2-(methyldisulfanyl)benzothiazole (41) and B) synthesis of ethyl (Z)- and (E)-3
Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines
Beilstein J. Org. Chem. 2021, 17, 334–342, doi:10.3762/bjoc.17.31
- address: MSD UK Discovery Centre, Francis Crick Institute, 1 Midland Road, London, NW1 1AT, United Kingdom 10.3762/bjoc.17.31 Abstract A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B – three
- papers addressed their biosynthesis. Thus, the investigation of the metabolites of Streptomyces sp. MA37 (from a soil sample obtained in Legon, Ghana) revealed the production of legonmycins A (3) and B (4) (Figure 2) and found that just four genes (lgnA–D) were necessary for their biosynthesis [22
- pxaAB gene cluster in E. coli, and analysis of the metabolites by differential 2D NMR spectroscopy, led to the isolation and characterization of pyrrolizixenamide A (9) and, subsequently, pyrrolizixenamides B–D (10–12). Ultimately, an analogous biosynthetic pathway to that proposed for the legonmycins
19F NMR as a tool in chemical biology
Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28
- pesticide cyhalothrin [106] by the fungus Cunninghamella elegans. In the former, 19F NMR demonstrated the appearance of phase 1 (oxidative) and phase 2 (conjugative) metabolites, and in the latter, it was possible to monitor the migration of the pesticide into the biomass in the first 24 h after its
- introduction before being biotransformed to new trifluoromethyl-containing metabolites (Figure 15). 19F NMR was also employed to determine the degree of biotransformation of drug-like fluorophenylpyridine carboxylic acids in the same fungus [107]. However, aside from these few examples, the technique is not
- . [110] investigated the bacterial degradation of pentafluorosulfanyl (SF5)-substituted aminophenols and via 19F NMR analysis of culture extracts was able to determine the production of new fluorinated metabolites (Figure 16). Subsequent analysis by GC–MS was required to further characterize the products
Molecular basis for protein–protein interactions
Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1
- can only be fully exploited via interactions, either in the form of PPIs or with other metabolites and biomolecules, such as nucleic acids. Thus, the identification of the molecular binding partners that proteins interact with is an interesting avenue to facilitate the discovery of the protein
Chemical constituents of Chaenomeles sinensis twigs and their biological activity
Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257
- continuing search for cytotoxic, antineuroinflammatory, and neurotrophic secondary metabolites from C. sinensis [13][14][15][21], the isolates (1–12) were tested for these biological activities. The cytotoxicity was evaluated on the basis of the growth inhibitory effects of the isolated compounds 1–12
- new drug candidates although further studies are needed. This phytochemical study on C. sinensis may exemplify, how novel secondary metabolites still remain undiscovered among the numerous well-known plant species. Experimental General experimental procedures. Optical rotation data were recorded using
Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities
Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248
- , Kgs. Lyngby, Denmark 10.3762/bjoc.16.248 Abstract Secondary metabolites provide Bacillus subtilis with increased competitiveness towards other microorganisms. In particular, nonribosomal peptides (NRPs) have an enormous antimicrobial potential by causing cell lysis, perforation of fungal membranes
- the principle root microbiome of maize [22]. Secondary metabolites (SMs) are believed to be important mediators of the interactions between microorganisms [23]. Many of them are well-studied in vitro, but the true ecological role of SMs is still the subject of investigations. Different opinions about
- fusiformis M5 confirmed the impact of B. subtilis-produced surfactin on the growth. Results Impact of B. subtilis secondary metabolites on taxonomic groups in semisynthetic mock communities We established soil-derived semisynthetic mock communities and supplemented them with B. subtilis WT P5_B1, the
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
- -10-1 Yurigaoka, Natori, Miyagi 981-1295, Japan Department of Marine Science, Faculty of Fisheries and Marine Science, Diponegoro University, Semarang, Central Java 50275, Indonesia 10.3762/bjoc.16.222 Abstract Chemical investigation of secondary metabolites from a marine-derived actinomycete strain
- -enantiomers with a ratio of 73:27, 4 is the pure (S)-enantiomer, and 5 is the (S)-enantiomer with 98% ee. The present study illustrates the diversity in the stereochemistry of anteiso branching in bacterial metabolites. Compounds 1−4 were moderately antimicrobial against Gram-positive bacteria and fungi, with
- [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
Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale
Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177
- sahnii, syn. Mycoleptodiscus indicus) are members of the Muyocopron genus [10]. Therefore, three azaphilone dimers [11] and a triterpenoid [12] previously isolated from Mycoleptodiscus indicus are now considered to be metabolites of Muyocopron strains. However, little information exists regarding the
- fungal metabolites produced by Muyocopron spp. Thus, as part of our research into the natural products produced by plant-associated fungi [13][14][15], we isolated two new azaphilones from the cultures of an endophytic fungus, namely Muyocopron laterale ECN279. Herein, the isolation, structural
Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio
Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154
- ]. Others can fix nitrogen [5], have phototrophy [6], or produce a plant hormone [7], and thus showing a higher metabolic versatility, which is also represented by 150 and more secondary metabolites discovered from this genus [8]. As part of our continuing study on the secondary metabolites of marine
Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)
Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132
- defend themselves with toxic or deterrent molecules [1][2][3][4][5][6][7][8]. Sponges (Porifera), for example, represent one of the main sources of marine bioactive natural products, due to their impressive chemical armoury [4]. These specialized metabolites can be produced either by the sponge itself or
- by associated microbial symbionts [9][10][11][12][13][14][15][16]. Their production is assumed to be useful against numerous environmental stress factors, such as predation, pathogens, overgrowth by fouling organisms, or competition for space [4][10][15][17]. Though defensive metabolites are
- metabolites to their own advantage [2][5][9][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Besides, specific metabolites can be passed on from the sea slugs to their similarly conspicuous and physically defenceless eggs. This has been shown exemplarily for the egg ribbons of certain
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
- secondary metabolism [15]. In the course of our continuing studies on bioactive metabolites of less studied bacterial taxa [16], Burkholderia sp. 3Y-MMP, isolated from soil by an exhaustive enrichment culture under Zn2+-load, was selected for a detailed chemical study, which resulted in the isolation of 4
- without a 3-methyl group, and the former lineages are unique to Burkholderia producers [28]. These metabolites are shown to be biosynthesized by head-to-head condensation of anthranilate and β-ketoacylate precursors, followed by a modification at C3 or nitrogen by putative monooxygenases or
A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA
Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100
- different levels, including DNA, RNA, proteins, and small molecule metabolites. Today, along with other methods in clinical diagnosis biosensors are ubiquitously used in the biomedical field. The first prototype of a biosensor was invented by Leland Clark and Champ Lyons in 1962 as an amperometric Clark
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
- mining indicated that members of the underexplored genus Pseudosporangium, from which no secondary metabolites have been reported to date, may harbor the biosynthetic machinery for the formation of novel natural products. The strain RD062863, that is available at a public culture collection, was obtained
- 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
- analytical technologies, the searching process for new microbial secondary metabolites became faster and more efficient [10]. However, there existed a substantial number of unstudied bacterial genera for which secondary metabolic ability is still unknown at the genus level. The 16S rRNA gene sequences are
Fabclavine diversity in Xenorhabdus bacteria
Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84
- global threat of multiresistant pathogens has to be answered by the development of novel antibiotics. Established antibiotic applications are often based on so-called secondary or specialized metabolites (SMs), identified in large screening approaches. To continue this successful strategy, new sources
- metabolite; Xenorhabdus; Introduction The constantly increasing threat of multiresistant pathogens requires the development of new antibiotics, as they are indispensable to maintain the state of health of our society [1]. Bacterial natural products, also called secondary or specialized metabolites (SM
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
- assignment of an E geometry at C8 in 2. As metabolites of microbes, compounds 1 and 2 are unprecedented in terms of bearing a 2,4-dienone system. Both 1 and 2 showed antibacterial activity against the plant pathogen Rhizobium radiobacter and the fish pathogen Tenacibaculum maritimum, with a contrasting
- was obtained from stony coral Catalaphyllia sp. and identified as a member of the genus Micrococcus by 16S rRNA gene sequence analysis. The HPLC–UV analysis of the fermentation broth of strain C5-9 indicated the presence of metabolites showing UV absorption around 275 nm. A large-scale shaking culture
- antimicrobial metabolites from an actinomycete [36] and a basidiomycete fungus [37]. In addition, long-chain saturated fatty acids possessing a keto group were detected in the solvent extract of Legionella by GC–MS analysis [38]. Fatty acid components in fresh water-derived Micrococcus species were
Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211
Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28
- : secalonic acids, ergoflavins, and ergochrysins), which are well-known mycotoxins that exhibit toxic, antibacterial, and mutagenic properties [1]. On the other hand, a limited number of monomeric tetrahydroxanthones has been reported as fungal metabolites to date, including the blennolides [2], diversonolic
Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica
Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293
- , Thailand Department of Chemistry, Faculty of Science, Prince of Songkla University, Songkhla 90112, Thailand 10.3762/bjoc.15.293 Abstract In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone
- bioactive secondary metabolites. Herein, we report on the isolation, structure elucidation, and biological activities of six compounds from Gibellula sp. and Cordyceps javanica. Furthermore, the species-specific patterns of secondary metabolite production were studied. Results and Discussion Structure
- close to each other [23], and they produce the same secondary metabolites according to the evidence from Kadlec and co-workers [24], Jegorov and co-workers [25], and Luangsa-ard and co-workers [26]. They unveiled the existences of beauverolides and beauvericin, originally described from Beauveria, in
Two new aromatic polyketides from a sponge-derived Fusarium
Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289
- structurally unique secondary metabolites with various biological activities [8][9]. Specifically, sponge-associated fungi are attracting substantial attention because of their high capability of producing a wide range of bioactive compounds [5][10][11]. As a tropical country, Indonesia is known as the second
- database. HPLC/UV-guided purification of the secondary metabolites from this strain led to the isolation of two new polyketides, karimunones A (1) and B (2), together with five known compounds (3–7, Figure 1). Compound 1 was obtained as a red powder. TOF-HRESIMS analysis gave a deprotonated molecule [M − H
- summary, our chemical analysis of a sponge-derived fungus of the genus Fusarium led to the identification of two new and three known aromatic polyketides (1 and 2, and 3–5, respectively) and two sesquiterpenes (6 and 7). Although secondary metabolites of Fusarium were extensively studied in the past [26
Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis
Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286
- Saarbrücken, Germany 10.3762/bjoc.15.286 Abstract The argyrins are secondary metabolites from myxobacteria with antibiotic activity against Pseudomonas aeruginosa. Studying their structure–activity relationship is hampered by the complexity of the chemical total synthesis. Mutasynthesis is a promising
Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering
Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283
- metabolites on the planet. To date more than 70,000 terpenoids (dictionary of natural products) have been characterized and grouped into more than 400 structural families – the vast majority of which have been isolated from plants and fungi [1]. Their structural diversity reflects the breadth of their
- functional roles, which range from widely distributed metabolites like cholesterol, to those with more restricted distribution like vitamins A and D, carotenoids, and steroid hormones, to some with highly restricted distribution like pheromones, fragrances, and defense metabolites [2][3]. Many of the more
- restricted members possess significant biological activities, like the anticancer agent taxol (1) [4] or the antimalarial agent artemisinin (2, Figure 1) [5][6]. The structural diversity and functional utility of this class of specialized metabolites have combined to encourage efforts to apply the tools of
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