Dinghupeptins A-D, Chymotrypsin Inhibitory Cyclodepsipeptides Produced by a Soil-Derived Streptomyces.

Four new cyclodepsipeptides, dinghupeptins A-D (1-4), possessing a rare N5-(2-hydroxylethyl)glutamine moiety, were isolated from cultures of the soil-derived Streptomyces sp. SC0581. Their structures were elucidated by spectroscopic and advanced Marfey's amino acid analysis, and their 3D structures were established by theoretical conformational analysis. Compounds 1 and 2, containing a 3-amino-6-hydroxypiperidone unit, displayed selective inhibition of chymotrypsin with IC50 values of 2.1 and 1.1 μM, respectively. Enzyme kinetic analysis and molecular docking experiments revealed they are competitive inhibitors binding to the active site of chymotrypsin.

• Publication year

  2018

• Venue

  Journal of Natural Products

• Publication date

  2018-09-17

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.jnatprod.7b01009PMID 30222343
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Isolation of Acacetin from Calea urticifolia with Inhibitory Properties against Human Monoamine Oxidase-A and -B.

  2016cited by this paper
• Mode of pancreatic lipase inhibition activity in vitro by some flavonoids and non-flavonoid polyphenols.

  2015cited by this paper
• Bisacremines A-D, Dimeric Acremines Produced by a Soil-Derived Acremonium persicinum Strain.

  2015cited by this paper
• Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.

  2014cited by this paper
• Cytotoxic and Antibacterial Quinone Sesquiterpenes from a Myrothecium Fungus.

  2014cited by this paper
• Concerted action of P450 plus helper protein to form the amino-hydroxy-piperidone moiety of the potent protease inhibitor crocapeptin.

  2013cited by this paper
• SAR analysis and bioactive potentials of freshwater and terrestrial cyanobacterial compounds: a review

  2013cited by this paper
• Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

  2010cited by this paper
• Ligand docking and binding site analysis with PyMOL and Autodock/Vina

  2010cited by this paper
• Depsipeptides from a Guamanian Marine Cyanobacterium, Lyngbya bouillonii, with Selective Inhibition of Serine Proteases.

  2010cited by this paper
• Micropeptins from an Israeli fishpond water bloom of the cyanobacterium Microcystis sp.

  2010cited by this paper
• Eight novel serine proteases inhibitors from a water bloom of the cyanobacterium Microcystis sp.

  2010cited by this paper
• Protease inhibitors from a water bloom of the cyanobacterium Microcystis aeruginosa.

  2009cited by this paper
• Symplocamide A, a potent cytotoxin and chymotrypsin inhibitor from the marine Cyanobacterium Symploca sp.

  2008cited by this paper
• The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals

  2008cited by this paper
• Proteinase-activated receptor-2 expression in breast cancer and the role of trypsin on growth and metabolism of breast cancer cell line MDA MB-231.

  2007cited by this paper
• Lyngbyastatins 5-7, potent elastase inhibitors from Floridian marine cyanobacteria, Lyngbya spp.

  2007cited by this paper
• Two new chymotrypsin inhibitors isolated from the Cyanobacterium Microcystis aeruginosa NIES-88.

  2005cited by this paper
• Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy.

  2005cited by this paper
• The serine proteinase thrombin promotes migration of human renal carcinoma cells by a PKA-dependent mechanism.

  2002cited by this paper
• Thrombin enhances adhesion in pancreatic cancer in vitro through the activation of the thrombin receptor PAR 1.

  2001cited by this paper
• Molecular structure of FR901277, a novel inhibitor of human leukocyte elastase, and its binding mode simulation.

  1999cited by this paper
• Activation of Type IV Procollagenases by Human Tumor-associated Trypsin-2*

  1997cited by this paper
• FR901277, a novel inhibitor of human leukocyte elastase from Streptomyces resistomycificus. Producing organism, fermentation, isolation, physico-chemical and biological properties.

  1993cited by this paper
• Serine proteases: structure and mechanism of catalysis.

  1977cited by this paper
• Influence of the Distance of the Proline Carbonyl from the β and γ Carbon on the 13C Chemical Shifts

  1975cited by this paper
• Influence of the distance of the proline carbonyl from the beta and gamma carbon on the 13C chemical shifts.

  1975cited by this paper
• 13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols

  1946cited by this paper

• Soil-Associated Microorganisms: A Natural Source of Biologically Active Compounds.

  2026cites this paper
• Total Syntheses of Stereoisomeric Congeners of Rufomycin Natural Products Having Anti-Mycobacterial Activity

  2025cites this paper
• Synthesis, DFT investigation, molecular docking, drug-likeness and molecular dynamic analysis of new quinoxaline-based pyrazoline derivatives

  2025cites this paper
• Side-Chain Macrocyclization in Ahp-Bicyclodepsipeptides Biosynthesis Involves Cytochrome P450-Catalyzed Sequential Aromatic Hydroxylation and C─N Coupling.

  2025cites this paper
• Isolation and structure determination of a new depsipeptide crocapeptin C from the myxobacterium Melittangium boletus

  2024cites this paper
• Synthesis of Novel Quinolines with Antibacterial Activity

  2023cites this paper
• Molecular docking, drug-likeness and DFT study of some modified tetrahydrocurcumins as potential anticancer agents

  2023cites this paper
• Recent advances on cyclodepsipeptides: biologically active compounds for drug research

  2023cites this paper
• Sadopeptins A and B, Sulfoxide- and Piperidone-Containing Cyclic Heptapeptides with Proteasome Inhibitory Activity from a Streptomyces sp.

  2023cites this paper
• Streptomyces: Still the Biggest Producer of New Natural Secondary Metabolites, A Current Perspective

  2022cites this paper
• First report on the synthesis and structural studies of trans-Phakellistatin 18: a rotamer of marine natural product phakellistatin 18

  2022cites this paper
• Synthesis, Antibacterial Activity, and Molecular Docking Study of Bispyrazole‐Based Derivatives as Potential Antibacterial Agents

  2022cites this paper
• New ent-kaurene and germacrene derivatives from Mesona procumbens Hemseley and their biological activity

  2022cites this paper
• Acuminatums E and F, two new cyclic lipopeptides from Fusarium lateritium HU0053 and their antifungal activity

  2022cites this paper
• Design, synthesis, and biological activity of 9-O-cinnamoylberberines as novel lipid-lowering agents.

  2022cites this paper
• Synthesis and cytotoxic activity of ethyl ferulate derivatives as potent anti-inflammatory agents

  2022cites this paper
• Synthesis and Cytotoxic Activity of Novel Ergosterol Peroxide Derivatives with Acrylate or Propionate Side Chain

  2022cites this paper
• Actinobacteria in natural products research: Progress and prospects.

  2021cites this paper
• From dolastatin 13 to cyanopeptolins, micropeptins, and lyngbyastatins: the chemical biology of Ahp-cyclodepsipeptides.

  2020cites this paper
• Thermodynamics, Kinetics and Mechanisms of Non-competitive Allosteric Inhibition of Chymotrypsin by Dihydrolipoic Acid-Coated Gold Nanoclusters.

  2020cites this paper
• Isolation, Identification, and Decomposition of Antibacterial Dialkylresorcinols from a Chinese Pseudomonas aurantiaca Strain.

  2020cites this paper
• MolDiscovery: learning mass spectrometry fragmentation of small molecules

  2020cites this paper
• α-Chymotrypsin catalyses the synthesis of methotrexate oligomers

  2020cites this paper
• Dihydrochalcones from the leaves of Lithocarpus litseifolius

  2020cites this paper
• Screening for natural inhibitors of human topoisomerases from medicinal plants with bio-affinity ultrafiltration and LC–MS

  2019cites this paper
• Screening for natural inhibitors of human topoisomerases from medicinal plants with bio-affinity ultrafiltration and LC–MS

  2019cites this paper