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Search for "metabolite" in Full Text gives 158 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells
Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133
- of THBERs 3a chosen as representative example, reveals that these two hydrogens are in cis position (Figure 4). Therefore, the THBERs 3 show the same configuration of the metabolite cavidine that is the 13-methyltetrahydroprotoberberine alkaloid which occur in various species of Corydalis [69
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
- the genus Doriprismatica and scalarane-containing dictyoceratid sponges of the Spongiidae family. The results also indicate that D. stellata passes the scalarane metabolite on to its egg ribbons, most likely for protective purposes. The scalarane showed antibacterial activity against the Gram-positive
- from the previously reported scalaranes [25][29][33][42][56][61][62], the new metabolite is functionalized at C-11 instead of C-12 and has a cyclopropane ring bridging C-3, C-22 and C-4 of ring A. Scalarane sesterterpenes are considered as chemotaxonomic markers for the sponge families Thorectidae
- between nudibranchs of the genus Doriprismatica and scalarane-containing dictyoceratid sponges of the families Thorectidae and Spongiidae. This relationship is further reflected by their shared specialized metabolite 12-deacetoxy-4-demethyl-11,24-diacetoxy-3,4-methylenedeoxoscalarin, as proven in this
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
- and subjected to metabolite analysis, which resulted in the discovery of a novel cyclopeptide, pseudosporamide (1), along with three new oligomycin-class polyketides, pseudosporamicins A–C (2–4). The unusual structure of compound 1, featured by a biaryl-bond bridging across a tripeptide scaffold, N
- widely used as an indicator of the taxonomic position of prokaryotes. It was believed that a high similarity of the 16S rRNA gene sequence implied the closeness or even the identity in other sets of genes including secondary metabolite biosynthetic genes. However, our recent analysis of Streptomyces
- species demonstrated that the distribution of secondary metabolite biosynthetic genes was not the same even in phylogenetically close species [11]. This finding became our starting point to explore the secondary metabolism in actinomycete genera from which no secondary metabolites were described. “Rare
Fabclavine diversity in Xenorhabdus bacteria
Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84
- 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
Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment
Beilstein J. Org. Chem. 2020, 16, 670–673, doi:10.3762/bjoc.16.64
- particular group of compounds of particular focus in our research activities are natural products with enamide moieties [11]. Among these, chondrochloren having a (Z)-enamide moiety features a rare structural motif. The myxobacterial metabolite chondrochloren A (1) was isolated from Chondromyces crocatus
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
- metabolite profiles using analytical HPLC coupled with diode array detection and mass spectrometry (HPLC–DAD–MS) revealed that the production of pigmentosin B (2) was apparently specific for Gibellula sp., while the glycoasperfuran 3 was specific for C. javanica. Keywords: antibiofilm agents; natural
- 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
- the secondary metabolite production among species of Cordycipitaceae, HPLC–UV–vis profiles of all fungal isolates were generated and compared to each other. This revealed that the individual species possessed unique secondary metabolite profiles. Pigmentosins A (1) and B (2) were detected in all
Two new aromatic polyketides from a sponge-derived Fusarium
Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289
- polyketide; Fusarium; marine fungus; secondary metabolite; sponge; Introduction Marine organisms have been known as a potential source of prospective bioactive compounds, and sponges are particularly emphasized as the most promising source among all marine invertebrates [1][2]. However, the collection of
- metabolite of the fungus Geosmithia [24]. Plant metabolites, feralolide and its glycoside, possessing the same skeleton as 2 were reported from the medicinal herb Aloe vera [29], but this carbon skeleton is novel as a fungal secondary metabolite. Experimental General experimental procedures NMR spectra were
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
Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering
Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283
- synthetic biology to engineer pathways that will expand molecular diversity, especially around scaffolds associated with high-value compounds. The biosynthetic logic of terpene formation differs significantly from the logic employed by other classes of secondary metabolite biosynthetic pathways. Bacterial
- lividans, under the control of exogenous promoters [92][93][94]. To minimize the cellular resource competition and facilitate cleaner analysis, many of these hosts have been engineered to remove native secondary-metabolite BGCs and for optimized terpene precursor supply [1][95][96][97]. Like Streptomyces
Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa
Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270
- isolated and characterized five previously undescribed secondary metabolites, skeletocutins M–Q (1–5), along with the known metabolite tyromycin A (6) from the fruiting bodies of the polypore Skeletocutis sp. The new compounds did not exhibit any antimicrobial, cytotoxic, or nematicidal activities. However
- by Skeletocutis. Interestingly, tyromycin A (6) was found to be the only common metabolite in fruiting bodies and mycelial cultures of the fungus, and none of the recently reported skeletocutins from the culture of the same strain were detected in the basidiomes. Keywords: basidiomycete
- MUCL56074. We have recently reported the known metabolite tyromycin A (6), together with 12 unprecedented congeners for which we proposed the trivial names skeletocutins A–L, which were obtained from a liquid culture of the same fungus [4]. A preliminary characterization of the producer organism suggested
Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256
- production of terpenoids as the dominant biosynthetic class of secondary metabolites. Results and Discussion Purification and identification The metabolite profile of A. nanangensis was examined on a limited range of solid and liquid media suitable for fungal metabolite production. The metabolite profile
- Aspergillus type species) and unidentified but metabolically talented fungi (>60,000 spectra from 3,000 species) returned no similar metabolite cohorts, suggesting an unknown species. Individual retention time/UV–vis searches of the dominant 15 secondary metabolites against our in-house pure metabolite
- library (>7,100 standards) also failed to provide a single known secondary metabolite, further suggesting the strain was a hitherto unaccounted species of Aspergillus. A. nanangensis was cultivated separately on jasmine rice and pearl barley for 21 days, which resulted in confluent and thick mycelial
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
- . Prof. Soedarto SH., Semarang 50275, Central Java, Indonesia 10.3762/bjoc.15.225 Abstract (2Z,4E)-3-Methyl-2,4-decadienoic acid (1) was identified as a major metabolite from a culture extract of a marine bacterium Microbulbifer which was collected from a stony coral Porites sp. NMR-based spectroscopic
Isolation of fungi using the diffusion chamber device FIND technology
Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216
- -dimethyl-4-oxobicyclo[3.1.1]hept-2-en-6-yl)pent-2-enoic acid, for which the trivial name heydenoic acid A is suggested. Notable is the occurrence of peaks containing m/z values attributable to isomers of the isolated metabolite. Compound 2 has a molecular formula of C15H22O3, (HRESIMS m/z: 251.1641 [M + H
- environment. Halotolerance was to date exclusively reported for members of the Cladosporium sphaerospermum complex [28]. Analysis of genes involved in secondary metabolite production suggested Cadophora malorum as a producer of bioactive compounds [29], as later confirmed by the results of Almeida et al. [30
Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica
Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189
- anti-inflammatory activity of compound 1 using rat macrophages. Results and Discussion L. archangelica metabolite isolation and identification For isolation of the major metabolites of L. archangelica, we used 100 g of fine ground seeds (Supporting Information File 1, Figure S2) and the method of
N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds
Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168
- can serve as the starting material to a variety of orthogonally protected derivatives of 2,3-diaminopropanoic acid. The bicyclic amino acid (S)-127 is a major metabolite of isazofos in corn grain and for toxicological studies both enantiomers were required [17]. To this end the aziridine ester (2S,1′R
Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif
Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144
- . Sulfone 8 was a relatively minor metabolite, at only 10% of sulfoxide 6. A chiral HPLC (IC column, solvent: 5% isopropanol in hexane; 1 mL/min) enantiomeric assay was conducted for sulfoxide 6 and the outcome compared with a racemic sample of 6, prepared by chemical oxidation of thioether 4 [22]. Although
- metabolised. Product profiles were again determined by HPLC analysis and relationships are summarised in Scheme 2. Incubation of racemic sulfoxide 6 led to a similar outcome to that for 4 with the formation of phenol sulfoxide 7 and phenol sulfone 8 suggesting that sulfoxide 6 is the first formed metabolite
- sulfoxide 6 to sulfone 9 in these re-incubation experiments. It may be that there is a barrier to uptake of the phenols into the fungal cells and that they are actively exuded when generated within the cell. As a final experiment sulfone 9, which was not observed as a metabolite, was prepared by mCPBA
Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1
Beilstein J. Org. Chem. 2019, 15, 1298–1303, doi:10.3762/bjoc.15.128
- domain organization of the two corresponding biosynthetic assembly lines further indicated that Massilia sp. NR 4-1 does not produce micacocidin, but a derivative of this secondary metabolite. The isolation of siderophores from microorganisms is usually straightforward due to their iron-dependent
- increased in the extract from the iron-deficient culture (Figure 1C). The corresponding metabolite, which is in the following referred to as massiliachelin (1), was subsequently isolated by HPLC. High-resolution ESIMS of 1 yielded a pseudomolecular ion peak at m/z 467.2033 [M + H]+, which indicates a
Phylogenomic analyses and distribution of terpene synthases among Streptomyces
Beilstein J. Org. Chem. 2019, 15, 1181–1193, doi:10.3762/bjoc.15.115
- , as they were present in all except one of the Streptomyces species (S. pactum KLBMP 5084) (Figure 1). This finding suggests that geosmin may have an important ecological function as a chemical signal or as protective specialised metabolite against biotic and abiotic stresses, similarly as the roles
- [33]. Therefore, these results could also be interpreted as evidence for a rapid evolution of secondary metabolite genes to create new natural products with beneficial ecological functions for the producing organism. While many streptomycetes produce geosmin as a major metabolite of their bouquets of
- transfers of terpene synthase genes in Streptomyces, but could also point to secondary metabolite genes as being less conserved than housekeeping (primary metabolism) genes. Rapid evolution of secondary metabolism can lead to new natural products with advanced ecological functions in specific ecological
New terpenoids from the fermentation broth of the edible mushroom Cyclocybe aegerita
Beilstein J. Org. Chem. 2019, 15, 1000–1007, doi:10.3762/bjoc.15.98
- secondary metabolite profiles of C. aegerita, we found several terpenoids in submerged cultures. Aside from the main metabolite, bovistol (1), two new bovistol derivatives B and C (2, 3) and pasteurestin C as a new protoilludane (4) were isolated by preparative HPLC. Their structures were elucidated by mass
- Discussion Both the ethyl acetate extract of the culture filtrate and the acetone extract of the mycelium of C. aegerita, grown in ZM/2 medium, contained a major metabolite with a molecular mass of 496 Da, as detected by HPLC–MS analysis. Its molecular formula C30H40O6 was deduced from its [M + Na]+ peak at
- bovistol, which was confirmed by the elucidation of the structure by COSY and HMBC NMR data [5]. In the course of the isolation of 1 the minor metabolites 2 and 3 accrued. Metabolite 2 was analysed for a molecular weight of 478 Da. Its molecular formula C30H38O5, deduced from HRESIMS data, indicated the
Back to the future: Why we need enzymology to build a synthetic metabolism of the future
Beilstein J. Org. Chem. 2019, 15, 551–557, doi:10.3762/bjoc.15.49
- cycle. To overcome the problem of unwanted malyl-CoA accumulation, a malyl-CoA thioesterase [59] had to be added to the synthetic network. This enzyme effectively recycles the dead-end metabolite back into two intermediates of the network, malate and free CoA, thus serving as a “proof-reading” enzyme at
Oxidative radical ring-opening/cyclization of cyclopropane derivatives
Beilstein J. Org. Chem. 2019, 15, 256–278, doi:10.3762/bjoc.15.23
- (Scheme 41). In 2015, Tyagi’s group presented a biomimetic synthesis of metabolite 149 from intermediate 148 by using catalytic vanadyl acetylacetonate and molecular O2 (Scheme 42) [122]. The transformation went through aerobic oxidation ring-opening of cyclopropanols. The results showed that the oxygen
- for the synthesis of metabolite. Acknowledgements The work was supported by the National Nature Science Foundation of China (Grant No. 21602056), Scientific Research Fund of Hunan Provincial Science and Technology Department (Grant No. 2018JJ3208), Scientific Research Fund of Hunan Provincial
Synthesis and biological activity of methylated derivatives of the Pseudomonas metabolites HHQ, HQNO and PQS
Beilstein J. Org. Chem. 2019, 15, 187–193, doi:10.3762/bjoc.15.18
- (HHQ, 1) are important signaling molecules involved in quorum sensing and as such play an important role in virulence regulation [3][10][11][12]. Another metabolite from the AQ biosynthesis pathway of P. aeruginosa is 2-heptyl-1-hydroxy-4(1H)-quinolone (generally referred to as 2-heptyl-4
Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates
Beilstein J. Org. Chem. 2019, 15, 130–136, doi:10.3762/bjoc.15.13
- is detected as metabolite in vivo in biochemistry [15], and is known to react in the atmosphere to afford the secondary organic aerosol as air pollutants [16]. Among the four diastereomers of LMdiols (Figure 2), 2b and 2c have already been reported [14][17][18][19][20]. Conversely, the distinct
N-Acylated amino acid methyl esters from marine Roseobacter group bacteria
Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276
- components of complex extracellular metabolite mixtures. The reported compounds are specific for Roseobacter group bacteria of the genera Roseovarius and Loktanella, in contrast to broadly distributed AHLs. Although their function as signalling compounds is not proven, the occurrence of 2-aminobutyric acid
Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers
Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241
- assumedly may not need to target the active site of the enzyme, but rather a different pocket or surface. To this end, further research on the exact molecular mechanism of the regulatory activity of PqsE is needed. PqsBC The small molecule 2-AA (27), which is also a secondary metabolite generated in the AQ
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