scholarly journals Saccharobisindole, Neoasterric Methyl Ester, and 7-Chloro-4(1H)-quinolone: Three New Compounds Isolated from the Marine Bacterium Saccharomonospora sp.

Marine Drugs ◽  
2021 ◽  
Vol 20 (1) ◽  
pp. 35
Author(s):  
Sohee Kim ◽  
Tu Cam Le ◽  
Sang-Ah Han ◽  
Prima F. Hillman ◽  
Ahreum Hong ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Marine Bacterium ◽  
High Resolution Mass Spectrometry ◽  
Micrococcus Luteus ◽  
Culture Broth ◽  
Chemical Components ◽  
Inhibition Activity ◽  
Chemical Structures ◽  
New Compounds ◽  
And Staphylococcus Aureus

Analysis of the chemical components from the culture broth of the marine bacterium Saccharomonospora sp. CNQ-490 has yielded three novel compounds: saccharobisindole (1), neoasterric methyl ester (2), and 7-chloro-4(1H)-quinolone (3), in addition to acremonidine E (4), pinselin (5), penicitrinon A (6), and penicitrinon E (7). The chemical structures of the three novel compounds were elucidated by the interpretation of 1D, 2D nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS) data. Compound 2 generated weak inhibition activity against Bacillus subtilis KCTC2441 and Staphylococcus aureus KCTC1927 at concentrations of 32 μg/mL and 64 μg/mL, respectively, whereas compounds 1 and 3 did not have any observable effects. In addition, compound 2 displayed weak anti-quorum sensing (QS) effects against S. aureus KCTC1927 and Micrococcus luteus SCO560.

scholarly journals Natalenamides A–C, Cyclic Tripeptides from the Termite-Associated Actinomadura sp. RB99

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3003 ◽  
Author(s):  
Seoung Rak Lee ◽  
Dahae Lee ◽  
Jae Sik Yu ◽  
René Benndorf ◽  
Sullim Lee ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cyclic Peptides ◽  
Culture Broth ◽  
Resonance Spectroscopy ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
Associated Bacteria ◽  
Chemical Structures ◽  
New Compounds ◽  
Powerful Strategy

In recent years, investigations into the biochemistry of insect-associated bacteria have increased. When combined with analytical dereplication processes, these studies provide a powerful strategy to identify structurally and/or biologically novel compounds. Non-ribosomally synthesized cyclic peptides have a broad bioactivity spectrum with high medicinal potential. Here, we report the discovery of three new cyclic tripeptides: natalenamides A–C (compounds 1–3). These compounds were identified from the culture broth of the fungus-growing termite-associated Actinomadura sp. RB99 using a liquid chromatography (LC)/ultraviolet (UV)/mass spectrometry (MS)-based dereplication method. Chemical structures of the new compounds (1–3) were established by analysis of comprehensive spectroscopic methods, including one-dimensional (1H and 13C) and two-dimensional (1H-1H-COSY, HSQC, HMBC) nuclear magnetic resonance spectroscopy (NMR), together with high-resolution electrospray ionization mass spectrometry (HR-ESIMS) data. The absolute configurations of the new compounds were elucidated using Marfey’s analysis. Through several bioactivity tests for the tripeptides, we found that compound 3 exhibited significant inhibitory effects on 3-isobutyl-1-methylxanthine (IBMX)-induced melanin production. The effect of compound 3 was similar to that of kojic acid, a compound extensively used as a cosmetic material with a skin-whitening effect.

scholarly journals New Antiproliferative Cembrane Diterpenes from the Red Sea Sarcophyton Species

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 411 ◽  
Author(s):  
Hossam M. Hassan ◽  
Mostafa E. Rateb ◽  
Marwa H. Hassan ◽  
Ahmed M. Sayed ◽  
Samah Shabana ◽  
...  
Keyword(s):  
Red Sea ◽  
Antiproliferative Activity ◽  
High Resolution Mass Spectrometry ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Future Design ◽  
Chemical Structures ◽  
New Compounds ◽  
Mcf 7

The combination of liquid chromatography coupled to high resolution mass spectrometry (LC-HRESMS)-based dereplication and antiproliferative activity-guided fractionation was applied on the Red Sea-derived soft coral Sarcophyton sp. This approach facilitated the isolation of five new cembrane-type diterpenoids (1–5), along with two known analogs (6 and 7), as well as the identification of 19 further, known compounds. The chemical structures of the new compounds were elucidated while using comprehensive spectroscopic analyses, including one-dimensional (1D) and two-dimensional (2D) NMR and HRMS. All of the isolated cembranoids (1–7) showed moderate in vitro antiproliferative activity against a human breast cancer cell line (MCF-7), with IC50 ranging from 22.39–27.12 µg/mL. This class of compounds could thus serve as scaffold for the future design of anticancer leads.

scholarly journals Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

2021 ◽  
Vol 17 ◽  
pp. 2390-2398
Author(s):  
Emmanuel Tope Oluwabusola ◽  
Olusoji O Adebisi ◽  
Fernando Reyes ◽  
Kojo S Acquah ◽  
Mercedes De La Cruz ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Antimicrobial Properties ◽  
2D Nmr ◽  
Culture Broth ◽  
Moderate Activity ◽  
North Central ◽  
Isolation And Characterization ◽  
Antimicrobial Evaluation ◽  
New Compounds

Five new phenolic siderophores 1–5 were isolated from the organic extract of a culture broth in a modified SGG medium of Pseudomonas sp. UIAU-6B, obtained from sediments collected from the Oyun river in North Central Nigeria. The structure of the new compounds, pseudomonin A–C (1–3) and pseudomobactin A and B (4 and 5) isolated alongside two known compounds, pseudomonine (6) and salicylic acid (7), were elucidated based on high-resolution mass spectrometry, 1D and 2D NMR analyses. The absolute configuration of the threonine residue in compounds 1–5 was determined by Marfey analysis. The antimicrobial evaluation of compound 4 exhibited the most potent activity against vancomycin-sensitive Enterococcus faecium VS144754, followed by 3 and 5, with MIC values ranging from 8 to 32 µg/mL. Compounds 2 and 3 exhibited moderate activity against Mycobacterium tuberculosis H37Rv, with MIC values of 7.8 and 15.6 µg/mL, respectively. Plausible biosynthetic hypotheses toward the new compounds 1–5 were proposed.

scholarly journals Viridistratins A−C, Antimicrobial and Cytotoxic Benzo[j]fluoranthenes from Stromata of Annulohypoxylon viridistratum (Hypoxylaceae, Ascomycota)

Biomolecules ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 805 ◽  
Author(s):  
Kevin Becker ◽  
Anna-Charleen Wessel ◽  
J. Jennifer Luangsa-ard ◽  
Marc Stadler
Keyword(s):  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
Biologically Active ◽  
Cytotoxic Activities ◽  
Tropical Fungi ◽  
Active Metabolites ◽  
Chemical Structures ◽  
New Compounds ◽  
Biologically Active Metabolites ◽  
Resolution Mass

During the course of our search for novel biologically active metabolites from tropical fungi, we are using chemotaxonomic and taxonomic methodology for the preselection of interesting materials. Recently, three previously undescribed benzo[j]fluoranthenes (1−3) together with the known derivatives truncatones A and C (4, 5) were isolated from the stromata of the recently described species Annulohypoxylon viridistratum collected in Thailand. Their chemical structures were elucidated by means of spectral methods, including nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). The new compounds, for which we propose the trivial names viridistratins A−C, exhibited weak-to-moderate antimicrobial and cytotoxic activities in cell-based assays.

scholarly journals Structure Elucidation and Cholinesterase Inhibition Activity of Two New Minor Amaryllidaceae Alkaloids

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1279
Author(s):  
Jana Maříková ◽  
Abdullah Al Mamun ◽  
Latifah Al Shammari ◽  
Jan Korábečný ◽  
Tomáš Kučera ◽  
...  
Keyword(s):  
Active Sites ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Cholinesterase Inhibition ◽  
Inhibition Activity ◽  
Amaryllidaceae Alkaloids ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Narcissus Pseudonarcissus ◽  
Inhibition Potency

Two new minor Amaryllidaceae alkaloids were isolated from Hippeastrum × hybridum cv. Ferrari and Narcissus pseudonarcissus cv. Carlton. The chemical structures were identified by various spectroscopic (one- and two-dimensional (1D and 2D) NMR, circular dichroism (CD), high-resolution mass spectrometry (HRMS) and by comparison with literature data of similar compounds. Both isolated alkaloids were screened for their human acetylcholinesterase (hAChE) and butyrylcholinesterase (hBuChE) inhibition activity. One of the new compounds, a heterodimer alkaloid of narcikachnine-type, named narciabduliine (2), showed balanced inhibition potency for both studied enzymes, with IC50 values of 3.29 ± 0.73 µM for hAChE and 3.44 ± 0.02 µM for hBuChE. The accommodation of 2 into the active sites of respective enzymes was predicted using molecular modeling simulation.

Synthesis and Antimicrobial activities of Some Polyphenol compounds by Nano ZnO-TBAB as a Heterogeneous Catalytic Media

2020 ◽  
Vol 17 ◽  
Author(s):  
Rahele Bargebid ◽  
Ali Khalafi-Nezhad ◽  
Kamiar Zomorodian ◽  
Leila Zamani ◽  
Ali Ahmadinejad ◽  
...  
Keyword(s):  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
Reusable Catalyst ◽  
Nano Zno ◽  
Antifungal Activities ◽  
Chemical Structures ◽  
Heterogeneous Catalytic ◽  
Solvent Free Conditions ◽  
New Compounds ◽  
Derivatives Of

Introduction: Mannich reaction is a typical example of a three-component condensation reaction and the chemistry of Mannich bases has been the matter of search by researchers. Here an efficient procedure for the synthesis of some new Mannich derivatives of simple phenols is described. Methods: In this procedure a microwave-assisted and solvent less condensation were done between different phenols, secondary amines and paraformaldehyde. The reactions proceed in the presence of catalytic amount of nano ZnO and tetrabutylammonium bromide (TBAB) in excellent yields. 10 new compounds were synthesized (A1-A10). Chemical structures of all new compounds were confirmed by different spectroscopic methods. We optimized the chemical reactions in different conditions. Optimization reactions were done in the presence of different mineral oxides, different amount of TBAB and also different solvents. Nano ZnO and TBAB in catalytic amounts and solvent free conditions were the best conditions. All the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated against some Candida, filaments fungi, gram positive and gram negative bacteria by broth micro dilution method as recommended by CLSI. Results: The result showed that compounds A2, A3 and A4 against most of the tested Candida species and compounds A5 and A7 against C. parapsilosis and C. tropicalis, exhibited considerable antifungal activities. Also Compounds A8 and A10 showed desirable antifungal activities against C. neoformance and C. parapsilosis, respectively. The antibacterial activities of the synthesized compounds were also evaluated. Compounds A6 - A10 against E. Fecalis and compounds A5, A7, A9 and A10 against P. aeruginosa showed desirable antibacterial activities. Discussion: We have synthesized some new Mannich adducts of poly-hydroxyl phenols in the presence of nano-ZnO as a reusable catalyst, with the hope of discovering new lead compounds serving as potent antimicrobial agents. The advantages of this method are generality, high yields with short reaction times, simplicity, low cost and matching with green chemistry protocols. The antimicriobial studies of Mannich derivatives of phenols showed desirable results in vitro.

Preparation and Antitubercular Activities of Palindromic Hydrazinecarbothioamides and Carbonothioic Dihydrazides

2019 ◽  
Vol 16 (11) ◽  
pp. 1202-1210 ◽  
Author(s):  
Michael Joseps Hearn ◽  
Gwendolyn Towers ◽  
Michael Henry Cynamon
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Virulent Strain ◽  
Chemotherapeutic Agents ◽  
Disc Diffusion ◽  
Global Public Health ◽  
Health Crisis ◽  
Chemical Structures ◽  
Public Health Crisis ◽  
Zones Of Inhibition ◽  
Diffusion Assay

Background:With approximately one-third of the world’s population infected, tuberculosis continues to be a global public health crisis. The rise of strains that are unusually virulent or highly resistant to current drugs is a cause of special concern, prompting research into new classes of compounds, as well as the re-evaluation of known chemotherapeutic agents.Objectives:The antimycobacterial activities associated with some recently-reported thiocarbonyl compounds kindled our interest in the synthesis of substituted hydrazinecarbothioamides (3) and carbonothioic dihydrazides (4), with the aim of investigating their potential in antitubercular drug design and discovery.Methods:In the present study, the title compounds 3 and 4 were prepared by the condensation of hydrazines with isothiocyanates in reactions readily controlled by stoichiometry, temperature and solvent. The compounds were assessed against Mycobacterium bovis BCG in Kirby-Bauer disc diffusion, and minimum inhibitory concentrations were determined against the virulent strain M. tuberculosis Erdman.Results:The chemical structures of these thermally stable compounds were determined by IR, 1HNMR, 13C-NMR, high-resolution mass spectrometry and elemental analysis. In the Kirby-Bauer disc diffusion assay, some of the compounds showed substantial diameters of inhibition against BCG. In some cases, the zones of inhibition were so large that no growth at all was observed on the assay plates. Against M. tuberculosis Erdman, several of the compounds showed significant activities. Compound 3h was the most active, demonstrating a minimum inhibitory concentration of 0.5 µg/mL.Conclusion:We found that the title compounds may be prepared conveniently in excellent purity and good yields. They are readily identified on the basis of their characteristic spectra. Some members of this class showed significant activities against mycobacteria. We conclude that further work will be warranted in exploring the antitubercular properties of these compounds.

scholarly journals Cylindromicin from Arctic-Derived Fungus Tolypocladium sp. SCSIO 40433

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1080
Author(s):  
Imran Khan ◽  
Jing Peng ◽  
Zhuangjie Fang ◽  
Wei Liu ◽  
Wenjun Zhang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Nuclear Overhauser Effect ◽  
Inhibition Activity ◽  
Tyrosinase Inhibition ◽  
Bioactive Natural Products ◽  
Chemical Structures ◽  
Overhauser Effect ◽  
Spectroscopic Analyses ◽  
Potential Resource ◽  
Nuclear Overhauser

The fungus strain SCSIO 40433 was isolated from an Arctic-derived glacier sediment sample and characterized as Tolypocladium cylindrosporum. A new compound, cylindromicin (1), and seven known secondary metabolites (2–8) were isolated from this strain. The chemical structures of these compounds were elucidated by comprehensive spectroscopic analyses. Cylindromicin (1) featured a 3,4-dihydro-2H-pyran skeleton. The absolute configuration of compound 1 was assigned via interpretation of key Nuclear Overhauser Effect Spectroscopy (NOESY) correlations and Electronic Circular Dichroism (ECD) calculation. Cylindromicin (1) exhibited significant tyrosinase inhibition activity. This study highlights Polar fungi as a potential resource for new bioactive natural products.

scholarly journals Biological Properties of Essential Oils from Thymus algeriensis Boiss

Plants ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 786
Author(s):  
Hamza Ouakouak ◽  
Adel Benarfa ◽  
Mohammed Messaoudi ◽  
Samir Begaa ◽  
Barbara Sawicka ◽  
...  
Keyword(s):  
Essential Oils ◽  
Micrococcus Luteus ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Cancer Cell Line ◽  
Antimicrobial Activities ◽  
Biological Properties ◽  
Chemical Components ◽  
Bornyl Acetate ◽  
Thymus Algeriensis

This study describes the chemical composition, antitumor, antioxidant, and antimicrobial activities of the plant Thymus algeriensis Boiss. Essential oils (EOs) were collected in different periods (before, during, and after flowering stage) from the El-Guetfa region, M’sila, Algeria. The EOs extraction was achieved using three distinguishing techniques: hydro (Clevenger trap), steam, and microwave distillations, targeting different aerial parts of the plant (stems, flowers, and leaves). The EOs chemical components were estimated using GC-FID and GC-MS apparatuses. The resulting yield of the extracted oil was moderate and ranged between 0.84 and 1.53% (wt/vol). In total, eighty-five components were identified, in which the oxygenated monoterpenes family formed the main portion, starting from 40.56 up to 70.66%. The obtained essential oil was dominated by five major components that varied from low to quite moderate percentages: camphor (17.45–32.56%), borneol (11.16–22.2%), camphene (7.53–12.86%), 1.8-cineole (5.16–11.21%), and bornyl acetate (3.86–7.92%). The biological results of this oil pointed out that the EOs extracted from the leaves part exposed a weak radical scavenging activity afterward using two well-known antioxidant assays DPPH (IC50 = 8.37 mg/mL) and ABTS (10.84 mg/mL). Meanwhile, this oil presented strong inhibition activity against colon cancer cell line HCT116 (LC50 = 39.8 µg/mL) and a moderate inhibitory against hepatocellular cancer cells HePG2 (LC50 > 100 µg/mL). In addition, this oil antimicrobial activity was quite important against Micrococcus luteus (M. luteus), Staphylococcus aureus CIP 7625, Escherichia coli ATCC 10536, Saccharomyces cerevisiae ATCC 4226, Candida albicans IPA200, Candida tropicalis (Ct), and Candida glabrata (Cg) after using Amoxicillin and Itraconazole as references.

scholarly journals Reaktive E=C(p–p)π Systeme, XXXIV Addition von Alkoholen oder primären Aminen an Phosphaalkene F3CP=C(F)OR. Neue Trifluormethylphosphane und -phosphaalkene/Reactive E = C( p – p ) π-Systems, XXXIV Addition of Alcohols or Primary Amines to Phosphaalkenes F3CP= C(F)OR . Novel Trifluoromethylphosphanes and Phosphaalkenes

1993 ◽  
Vol 48 (1) ◽  
pp. 58-67 ◽  
Author(s):  
Joseph Grobe ◽  
Duc Le Van ◽  
Gudrun Lange
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Molar Ratio ◽  
Primary Amines ◽  
The Novel ◽  
Experimental Conditions ◽  
Pull System ◽  
Fragment Ions ◽  
New Compounds ◽  
C Nmr

The course of the reactions o f fluorophosphaalkenes F3CP = C (F)OR [R = Me (1), Et (2)] with methanol or ethanol strongly depends on the experimental conditions. Thus at 70 °C a mixture of the 2-phosphapropionic acid ester F3CP (H )CO2R [R = Me (3), Et (4)] and trifluoromethylphosphane H2PCF3 is formed [molar ratio: 3 or 4 /H2 CF3 ≈1/1]. If the precursors F3CP (H )CO2R [R = Me (3), Et) are used as starting materials, the reaction with ROH under the same conditions affords 3 and 4, respectively, (90 to 95% yield) with only traces of H2PCF 3. In the presence o f iPr2NH these precursors react with R′OH to give the novel trifluoromethylphosphaalkenes F3CP = C (OR )OR [R /R′: Me/Me (6); E t/E t (7); Me/Et (8)]. With Et2NH , 3 undergoes an addition/elimination process yielding the interesting push/pull system Et2N(F)C = P-CO2Me (5). 1 and 2 react with primary amines R′NH2 (R′= tBu, Me) with stereoselective formation of the fairly labile phosphaalkenes F3CP = C(OR)NHR′ [R /R′: Me/tBu (9), Et/tBu(10), Me/Me (11)] with trans-positions for CF3 and NHR′.The new compounds 3 -11 were characterized by spectroscopic investigations (1H , 19F, 31P, 13C NMR ; IR, MS) and determination of M+ or typical fragment ions [M+ -OR ] by high resolution mass spectrometry.

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