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Journal: New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus. (Pubmed Central) - Nov 21, 2020
Compound 3 displayed antibacterial activity against Pseudomonas aeruginosa (minimum inhibitory concentration (MIC) = 32 μg/mL) and antifungal activity against Candida albicans (MIC = 32 μg/mL). In addition, compound 3 exhibited an inhibitory effect on protein tyrosine phosphatase 1 B (PTP1B), an important hypoglycemic target, with an inhibitory concentration (IC) value of 12.25 μM.
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Journal: Study of bicyclomycin biosynthesis in Streptomyces cinnamoneus by genetic and biochemical approaches. (Pubmed Central) - Nov 19, 2020
The 2,5-Diketopiperazines (DKPs) constitute a large family of natural products with important biological activities...The identity of the intermediates, which were reproduced in vitro using purified enzymes, allowed us to characterize the pathway and corroborate previous reports. Finally, we show that the putative antibiotic transporter was dispensable for the producing strain.
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Journal: Diketopiperazine Formation in Fungi requires Dedicated Cyclization and Thiolation Domains. (Pubmed Central) - Oct 31, 2020
Point mutation of conserved active sites in the C and T domains diminished cyclization activity of GliP in vitro and abolished gliotoxin biosynthesis in vivo. Verified NRPSs of other fungal DKPs terminate with similar CT domain couplets, suggesting a conserved strategy for DKP biosynthesis by fungal NRPSs.
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Journal: Reprogramming Escherichia coli for the production of prenylated indole diketopiperazine alkaloids. (Pubmed Central) - Oct 27, 2020
Purified product yields of 2-26 mg/L per culture were obtained from culture supernatants. Our study paves the way for the bioproduction of novel prenylated indole DKP alkaloids in a tractable chassis that can exploit the cyclodipeptide diversity achievable with CDPSs and the numerous described PT activities.
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Journal: Prebiotic oligomerization and self-assembly of structurally diverse xenobiological monomers. (Pubmed Central) - Oct 20, 2020
Many modern biopolymers degrade abiotically preferentially via processes which produce thermodynamically stable ring structures, e.g. diketopiperazines in the case of proteins and 2', 3'-cyclic nucleotide monophosphates in the case of RNA...We explored here the oligomerization of a structurally diverse set of prebiotically plausible xenobiological monomers, which can hydrolytically interconvert between cyclic and acyclic forms, alone or in the presence of glycine under moderate temperature drying conditions. These monomers included various lactones, lactams and a thiolactone, which varied markedly in their stability, propensity to oligomerize and apparent modes of initiation, and the oligomeric products of some of these formed self-organized microscopic structures which may be relevant to protocell formation.
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Journal: Chetomin rescues pathogenic phenotype of LRRK2 mutation in drosophila. (Pubmed Central) - Oct 1, 2020
As proof of principle, we demonstrated that Chetomin recapitulated the rescue in these mutant Drosophila. Our findings suggest that Chetomin can be a potential therapeutic compound in LRRK2 linked Parkinson's disease.
- |||||||||| Ampion (diketopiperazine) / Ampio, mycophenolate sodium / Generic mfg.
Journal: Secondary metabolites of the genus Penicillium from undisturbed and anthropogenically altered Antarctic habitats. (Pubmed Central) - Sep 30, 2020
It is only from contaminated soils there were isolated fungi that produced more structurally diverse secondary metabolites pertaining to polycyclic indole alkaloids and terpenoids. The fungi isolated from contaminated samples can be used in biodegradation of oil spills and bioremediation of the environment, and also as producers of promising biologically active compounds.
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Journal: In Silico Evaluation of the Radical Scavenging Mechanism of Mactanamide. (Pubmed Central) - Sep 30, 2020
Mactanamide (MA) is a diketopiperazine isolated from marine fungi of the genus Aspergillus...In polar media, the HOO radical scavenging activity of MA is therefore 18 times higher than that of Trolox, the reference compound when assessing antioxidant activity. The results presented here align well with the experimental data, validating the mechanistic pathways and thus providing useful insights into the antioxidant activity of MA.
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Journal: Four pairs of proline-containing cyclic dipeptides from Nocardiopsis sp. HT88, an endophytic bacterium of Mallotus nudiflorus L. (Pubmed Central) - Sep 2, 2020
The eight 2,5-diketopiperazines (DKPs) were identified as cyclo(L-Pro-L-Leu) (1), cyclo(Pro-Leu) (2), cyclo(L-trans-Hyp-L-Leu) (3), cyclo(D-trans-Hyp-D-Leu) (4), and cyclo(D-Pro-L-Phe) (5), cyclo(L-Pro-L-Phe) (6), and cyclo(D-cis-Hyp-L-Phe) (7), cyclo(L-trans-Hyp-L-Phe) (8), respectively. Up to date, this is the first isolation of four pairs of proline based DKPs from Nocardiopsis sp.
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Journal: Characterization of diketopiperazine heterodimers as potential chemical markers for discrimination of two dominant black aspergilli, Aspergillus niger and Aspergillus tubingensis. (Pubmed Central) - Aug 4, 2020
Pestalamide D exhibited significant activities against B. cinerea, C. lagenarium, and V. mali, with MIC values of 4, 8, and 8 μg/mL, respectively, compared with the positive controls carbendazim (MICs = 8, 4, and 4 μg/mL) and prochloraz (MICs = 8, 8, and 4 μg/mL). The results of this study reveal two additional chemical markers and provide a powerful tool for the rapid identification of black aspergilli.
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Journal: Draft Genome Sequence of Bacillus sp. Strain SPB7, Isolated from the Marine Sponge Spongia officinalis. (Pubmed Central) - Jul 29, 2020
This bacterium is a producer of an antimicrobial cyclic diketopiperazine, (3S,6S)-3,6-diisobutylpiperazine-2,5-dione. The genome consists of 4,511 protein-coding genes, 63 tRNAs, 2 16S rRNAs, 3 23S rRNAs, and a single copy of 5S rRNA.
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Journal: Total Synthesis of A54145 Factor D. (Pubmed Central) - Jul 22, 2020
The peptide was constructed by attaching the peptide to the 2'-chlorotrityl polystyrene resin via Sar5 and developing conditions that avoided diketopiperazine formation upon subsequent elaboration using 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis...Consistent with recent studies by others, we found that the MeOAsp residue has the 2S,3R configuration. We also established that the configuration of the stereocenter in the anteiso-undecanoyl lipid tail does not affect biological activity.
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Journal: Conformational Study of the Jet-Cooled Diketopiperazine Peptide Cyclo Tyrosyl-Prolyl. (Pubmed Central) - Jul 21, 2020
IR-UV results are not sufficient for unambiguous assignment of the observed spectra to either folded or extended conformations and the simulation of the vibronic pattern of the S-S transition is necessary. Still, the comparison between IR-UV results and anharmonic calculations allows explanation of the minor structural differences between cyclo LTyr-LPro and cyclo LTyr-DPro in terms of different NH···π and CH···π interactions.
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Journal: Antifungal Nafuredin and Epithiodiketopiperazine Derivatives From the Mangrove-Derived Fungus Trichoderma harzianum D13. (Pubmed Central) - Jul 19, 2020
Trichodermamide G was found to be a novel epithiodiketopiperazine derivative with an unprecedented cyclic system containing a sulfur bridge, and nafuredin C represented the third nafuredin derivative of these homologous compounds. The new compound nafuredin C exhibited obvious antifungal activity against Magnaporthe oryzae with a minimum inhibitory concentration (MIC) of 8.63 μM, which is on the same order of magnitude as the positive control carbendazim (MIC = 3.27 μM).
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Journal: Expanding the Structural Diversity of Drimentines by Exploring the Promiscuity of Two N-methyltransferases. (Pubmed Central) - Jul 15, 2020
Although diverse tailoring enzymes are found to be clustered with cyclodipeptide synthases (CDPSs) to perform further modification reactions on the diketopiperazine (DKP) rings generating complex DKP-containing compounds, so far, a limited number of methyltransferases (MTs) co-occurring with CDPS have been experimentally characterized...Their combinatorial expression with the dmt1 genes in different Streptomyces strains successfully generated eight unnatural DMT analogs. Our results enriched the MT tool-box, setting the stage for exploring the structural diversity of DKP derivatives for drug development.
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Journal: A Modular Construction of Epidithiodiketopiperazines. (Pubmed Central) - Jul 9, 2020
To this end, the utility of a bifunctional triketopiperazine building block for the straightforward synthesis of ETPs is reported. A modular strategy consisting of enolate alkylation followed by site-selective nucleophile addition enables the concise synthesis of (±)-hyalodendrin and a range of analogues.
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Preclinical, Journal: Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillusversicolor DY180635. (Pubmed Central) - Jul 3, 2020
The structures and absolute configurations of compounds 1-6 were determined by the comprehensive analyses of nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), and electronic circular dichroism (ECD) calculation. All isolated compounds were selected for the virtual screening on the coronavirus 3-chymoretpsin-like protease (Mpro) of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2), and the docking scores of compounds 1-2, 5, 6, 8 and 17 were top among all screened molecules, may be helpful in fighting with Corona Virus Disease-19 (COVID-19) after further studies.
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Journal: Ir-Catalyzed Double Asymmetric Hydrogenation of 3,6-Dialkylidene-2,5-diketopiperazines for Enantioselective Synthesis of Cyclic Dipeptides. (Pubmed Central) - Jul 2, 2020
The double hydrogenation of 5a to 6a proceeded significantly faster than that of its half-hydrogenated intermediate (S)-7a, indicating that the double AH reaction involves primarily a processive mechanism, in which a single catalyst molecule performs consecutive hydrogenation of the two C=C double bonds in substrate 5a without dissociation of the partially reduced 7a. The present protocol represents a rare example of asymmetric catalytic consecutive hydrogenation of heterocycles and provides an alternative way for efficient construction of cyclic dipeptides.
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Journal: Binding of distinct substrate conformations enables hydroxylation of remote sites in thaxtomin D by cytochrome P450 TxtC. (Pubmed Central) - Jun 12, 2020
Here we report biochemical, structural, and theoretical studies of TxtC, an unusual bifunctional CYP involved in the biosynthesis of the EPA-approved herbicide thaxtomin A. TxtC was shown to hydroxylate two remote sites within the Phe residue of its diketopiperazine substrate thaxtomin D. The reactions follow a preferred order, with hydroxylation of the α-carbon preceding functionalization of the phenyl group...Molecular dynamics simulations confirmed that the -hydrogen is sufficiently close to the ferryl oxygen atom to be extracted by it and indicated that the two substrate conformations cannot readily interconvert in the active site. These results indicate that TxtC is able to hydroxylate two spatially remote sites by binding distinct conformations of the substrate and monohydroxylated intermediate.
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Review, Journal: Occurrence and Properties of Thiosilvatins. (Pubmed Central) - May 28, 2020
However, recent observations indicate that these compounds have been possibly neglected in the metabolomic characterization of fungi, particularly from marine sources. Aspects concerning occurrence, bioactivities, structural, and biosynthetic properties of thiosilvatins are reviewed in this paper.
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Clinical, Journal, Cytokine storm: The novel immunomodulatory biologic LMWF5A for pharmacological attenuation of the "cytokine storm" in COVID-19 patients: a hypothesis. (Pubmed Central) - May 22, 2020
If successful, this therapy may attenuate the cytokine storm observed in these patients and potentially reduce mortality, increase ventilation free days, improve oxygenation parameters and consequently lessen the burden on patients and the intensive care unit. In conclusion, in vitro findings suggest that the immunomodulatory effects of LMWF5A make it a viable candidate for treating cytokine storm and restoring homeostasis to the immune response in COVID-19.
- |||||||||| amoxicillin / Generic mfg.
Journal: Mechanistic and ecotoxicological studies of amoxicillin removal through anaerobic degradation systems. (Pubmed Central) - May 17, 2020
fischeri was the most sensitive organism to effluent treated under semi-continuous flow conditions; a continuous reduction in bioluminescence of up to 88.8% was observed after 39 days of feeding, which was associated with by-products accumulation due to unbalanced conditions during anaerobic digestion. Changes in the physico-chemical characteristics of the effluent caused the accumulation and removal of AMX-DKP IV and modified the toxicity to Lactuca sativa and R. subcapitata.
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Journal: Citriperazines A-D produced by a marine algae-derived fungus Penicillium sp. KMM 4672. (Pubmed Central) - May 11, 2020
Four new diketopiperazine alkaloids, citriperazines A-D were isolated from algae-derived Penicillium sp...The absolute configurations of compounds 1 and 4 were established by comparison of calculated and experimental ECD spectra. The cytotoxicity of compounds 1-4 against several human prostate cell lines was evaluated.
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