New bioactive metabolites from Penicillium purpurogenum MM

2016 ◽  
Vol 71 (4) ◽  
pp. 287-295 ◽  
Author(s):  
Mohamed Shaaban ◽  
Mohammad Magdy El-Metwally ◽  
Hartmut Laatsch
Keyword(s):  
Mass Spectra ◽  
Dimethyl Acetal ◽  
Bioactive Metabolites ◽  
Cytotoxic Activities ◽  
Penicillium Purpurogenum ◽  
Chemical Structures ◽  
Ergosterol Peroxide ◽  
New Compounds ◽  
Taxonomic Characterization

AbstractThree new bioactive compounds, namely (S)-tenellic acid B dimethyl acetal (1a), (3R,3′R/S)-isotalarone (2), and (3R,5R)-cis-5-methyl-3-(2-oxobutyl)-dihydrofuran-2-one (3), were isolated from the terrestrial fungus Penicillium purpurogenum MM, together with 15 known metabolites: talaroflavone, pestalasin A, altenuene, penicillide, 3′-O-methyl-dehydroisopenicillide, rubralactone, tenellic acid B, diaporthin, butyrolactone 1, butyrolactone-V, 4-hydroxy-2-methoxyacetanilide, ergosterol, ergosterol peroxide, linoleic acid, and glycerol monolinoleate. The chemical structures of the three new compounds were confirmed by extensive one- and two-dimensional NMR and electron spray ionization high-resolution mass spectra measurements and by comparison with literature data. The absolute configurations of the new compounds, and of talaroflavone (4a) and tenellic acid B (2b), were determined by ab initio calculations of ECD, ORD, and NMR data. The antimicrobial and cytotoxic activities of the crude extract and of the isolated compounds were studied using a set of microorganisms and brine shrimp assay, respectively. The isolation and taxonomic characterization of P. purpurogenum MM is reported.

scholarly journals Synthesis and characterization of Fe3O4/PEG-400/oxalic acid magnetic nanoparticles as a heterogeneous catalyst for synthesis of pyrrolin-2-ones derivatives

2021 ◽  
pp. 59-59
Author(s):  
Seyran Esmaeilzadeh ◽  
Davood Setamdideh
Keyword(s):  
Oxalic Acid ◽  
Mass Spectra ◽  
Chemical Structure ◽  
Room Temperature ◽  
One Pot ◽  
Chemical Structures ◽  
Peg 400 ◽  
Ft Ir ◽  
New Compounds

In this study, oxalic acid has been successfully loaded on Fe3O4/PEG-400 under ultrasonic irradiation and Fe3O4/PEG/oxalic acid as a new nanomagnetic catalyst has been synthesized. The chemical structure of the catalyst has been investigated by FT-IR spectrum, XRD, EDX and SEM methods. The catalyst has been used for the synthesis of 3-acyl-5-hydroxy-3-pyrrolin-2-one derivatives from the corresponding aldehydes, anilines and dimethyl acetylenedicarboxylate (DMAD) by one-pot and three-component the MCR reaction in the excellent yields (90-95 %) of products within 24 hours at room temperature. The fourteen samples are available. The recovered catalyst could be satisfactorily used for the second and third run without regeneration. This method has green and eco-friendly profile. Also, this research introduces an improvement mechanism for the types of this reaction. The chemical structures of new compounds have been characterized by FT-IR, 1H-NMR, 13C-NMR, and Mass spectra.

A new furan carboxamide and two potential precursors from a terrestrial streptomycete

2017 ◽  
Vol 72 (3) ◽  
pp. 175-182 ◽  
Author(s):  
Humaira Naureen ◽  
Michel Feussi Tala ◽  
Khaled A. Shaaban ◽  
Mohamed Shaaban ◽  
Anja Schüffler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Density Functional ◽  
Acid Amide ◽  
Octadecenoic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Bioactive Metabolites ◽  
Cytotoxic Activities ◽  
Tetradecanoic Acid ◽  
Vinyl Phenol ◽  
New Compounds

Abstract Three new bioactive metabolites, 1,6-dihydroxy- 2-methyl-heptan-4-one (1), 4-hydroxy-1-(2-methyl-oxiranyl)- pentan-2-one (2), and 2-(2-hydroxy-propyl)-4-methylfuran- 3-carboxylic acid amide (3) were isolated from the terrestrial Streptomyces sp. isolate ANK245, along with the new microbial constituent p-vinylanisol (4a) and the known metabolites p-vinyl-phenol (4b) and phenethyl alcohol. Analysis of the nonpolar part of the extract by gas chromatography/mass spectrometry (GC-MS) provided further evidence for tetradecanoic acid, 9-octadecenoic acid, hexadecanoic acid, 2-methoxy-4-vinylphenol (4c), 4-hydroxy-3-methoxy-benzaldehyde, o-hydroxybiphenyl, and 1,5,9-trimethyl-4,8,13-cyclotetradecatrien-1,3-diol (5). Structures 1–3 of the new compounds were elucidated by nuclear magnetic resonance (NMR) and NMR spectroscopy, but mass spectrometry (MS) techniques and their absolute configuration were determined by density functional theory (DFT) calculations and Mosher derivatisation. Their antimicrobial and cytotoxic activities were evaluated in comparison with the crude bacterial extract.

scholarly journals MMHub, a database for the mulberry metabolome

Database ◽  
2020 ◽  
Vol 2020 ◽  
Author(s):  
Dong Li ◽  
Bi Ma ◽  
Xiaofei Xu ◽  
Guo Chen ◽  
Tian Li ◽  
...  
Keyword(s):  
Mass Spectra ◽  
Chemical Compounds ◽  
Bioactive Metabolites ◽  
Molecular Formula ◽  
Experimental Conditions ◽  
Chemical Structures ◽  
Pubchem Compound ◽  
Specific Distribution ◽  
Small Chemical ◽  
Metabolome Data

Abstract Mulberry is an important economic crop plant and traditional medicine. It contains a huge array of bioactive metabolites such as flavonoids, amino acids, alkaloids and vitamins. Consequently, mulberry has received increasing attention in recent years. MMHub (version 1.0) is the first open public repository of mass spectra of small chemical compounds (<1000 Da) in mulberry leaves. The database contains 936 electrospray ionization tandem mass spectrometry (ESI-MS2) data and lists the specific distribution of compounds in 91 mulberry resources with two biological duplicates. ESI-MS2 data were obtained under non-standardized and independent experimental conditions. In total, 124 metabolites were identified or tentatively annotated and details of 90 metabolites with associated chemical structures have been deposited in the database. Supporting information such as PubChem compound information, molecular formula and metabolite classification are also provided in the MS2 spectral tag library. The MMHub provides important and comprehensive metabolome data for scientists working with mulberry. This information will be useful for the screening of quality resources and specific metabolites of mulberry. Database URL: https://biodb.swu.edu.cn/mmdb/

scholarly journals Secondary metabolites of Phlebopus species from Northern Thailand

2020 ◽  
Vol 19 (12) ◽  
pp. 1525-1536
Author(s):  
Boontiya Chuankid ◽  
Hedda Schrey ◽  
Benjarong Thongbai ◽  
Olivier Raspé ◽  
Norbert Arnold ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Tumor Cell Lines ◽  
Submerged Cultures ◽  
Esi Ms ◽  
Spectroscopic Analyses ◽  
New Compounds ◽  
Comprehensive Characterization

AbstractSubmerged cultures of the edible mushrooms Phlebopus portentosus and Phlebopus spongiosus were screened for their secondary metabolites by HPLC-UV/Vis and HR-LC-ESI-MS. Two new compounds, 9′-hydroxyphenyl pulvinone (1), containing an unusual pulvinone structure, and phlebopyron (2), together with the seven known pigments, atromentic acid (3), xerocomic acid (4), variegatic acid (5), methyl atromentate (6), methyl isoxerocomate (7), methyl variegatate (8), and variegatorubin (9) were isolated from the cultures. Their structures were assigned on the basis of extensive 1D/2D NMR spectroscopic analyses, as well as HR-ESI-MS, and HR-ESI-MS/MS measurements. Furthermore, the isolated compounds were evaluated for their antimicrobial and cytotoxic properties. 9′-hydroxyphenyl pulvinone (1), xerocomic acid (4), and methyl variegatate (8) exhibited weak to moderate cytotoxic activities against several tumor cell lines. The present paper provides a comprehensive characterization of pigments from the class of pulvinic acids that are present in the basidiomes of many edible bolete species.

scholarly journals Cytotoxic Polyketides from the Marine Sponge-Derived Fungus Pestalotiopsis heterocornis XWS03F09

Molecules ◽  
2019 ◽  
Vol 24 (14) ◽  
pp. 2655 ◽  
Author(s):  
Lei ◽  
Lei ◽  
Zhou ◽  
Hu ◽  
Niu ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Fermentation Broth ◽  
Human Cancer ◽  
Optical Rotation ◽  
Cytotoxic Activities ◽  
Human Cancer Cell Lines ◽  
Chemical Structures ◽  
Ic50 Values ◽  
New Compounds

Four new compounds, including two new polyketides, heterocornols M and N (1, 2), and a pair of epimers, heterocornols O and P (3, 4), were isolated from the fermentation broth of the marine sponge-derived fungus Pestalotiopsis heterocornis XWS03F09, together with three known compounds (5–7). The new chemical structures were established on the basis of a spectroscopic analysis, optical rotation, experimental and calculated electronic circular dichroism (ECD). All of the compounds (1–7) were evaluated for their cytotoxic activities, and heterocornols M-P (1–4) exhibited cytotoxicities against four human cancer cell lines with IC50 values of 20.4–94.2 μM.

Synthesis and characterization of N-glucosylated dithiadiazepine derivatives through carbon-sulfur bond formation

2015 ◽  
Vol 21 (5) ◽  
pp. 269-272 ◽  
Author(s):  
Snehal A. Chavan ◽  
Avinash G. Ulhe ◽  
Baliram N. Berad
Keyword(s):  
Bond Formation ◽  
Synthesis And Characterization ◽  
Mass Spectral ◽  
H Nmr ◽  
Chemical Structures ◽  
Elemental Analyses ◽  
New Compounds ◽  
Sulfur Bond ◽  
C Nmr

AbstractNew 4,7-bis(arylamino)-2-tetra-O-acetyl-β-d-glucopyranosylimino-1,3,5,6-dithiadiazepines were synthesized via reaction of N-tetra-O-acetyl-β-d-glucopyranosyl isocyanodichloride with 1,6-diaryl-2,5-dithio-bis-ureas without using any catalyst. Thus, the synthesis of 7-membered heterocycles containing two sulfur and two nitrogen atoms through carbon-sulfur bond formation was explored. The chemical structures of these new compounds were elucidated by IR, 1H NMR, 13C NMR, mass spectral, and elemental analyses.

Synthesis and Pharmacological Evaluation of a Novel Series of Cyclopentenone Derivatives

2017 ◽  
Vol 41 (1) ◽  
pp. 50-56 ◽  
Author(s):  
Fatma A. El-Samahy ◽  
Marwa El-Hussieny ◽  
Naglaa F. El-Sayed ◽  
Elsayed M. Shalaby ◽  
Fayez H. Osman
Keyword(s):  
Mass Spectra ◽  
Secondary Amines ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Chemical Structures ◽  
Pharmacological Evaluation ◽  
New Compounds ◽  
C Nmr ◽  
Boiling Toluene

A novel series of cyclopent-2-enone derivatives have been synthesised by the reaction of 4-hydroxy-3,4-diphenylcyclopent-2-enone, cyclic secondary amines, phosphorus reagents, hexamethylphosphoramide and Lawesson's reagent in boiling toluene/THF. The chemical structures of new compounds were identified by 1H NMR, 13C NMR, 31P NMR and mass spectra. Furthermore, the structure of one of the synthesised compounds has been confirmed using single crystal X-ray diffraction. The pharmacological evaluation results of antilung and anticolon carcinoma cell line properties for the products are discussed.

Synthesis and characterization of di-n-hexylamino-substituted phthalocyanines

2002 ◽  
Vol 06 (07) ◽  
pp. 489-493 ◽  
Author(s):  
Gülay Gümüş ◽  
Vefa Ahsen
Keyword(s):  
Mass Spectra ◽  
Electronic Spectroscopy ◽  
Metal Salts ◽  
Synthesis And Characterization ◽  
Organic Base ◽  
Metal Free ◽  
Elemental Analyses ◽  
New Compounds

Metal-free- and metallophthalocyanines ( M = Ni , Zn and Co ) carrying four di-n-hexylamino and four chloro groups in peripheral positions have been synthesized from the corresponding dichlorophthalonitrile derivative in the presence of the anhydrous metal salts [ NiCl 2, Zn ( O 2 CMe )2, CoCl 2] or a strong organic base. The new compounds have been characterized by elemental analyses, IR, NMR and electronic spectroscopy and mass spectra.

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.

Synthesis, Antimicrobial Evaluation of Some New 1, 3, 4-Thiadiazoles and 1, 3, 4- Thiadiazines

2018 ◽  
Vol 15 (8) ◽  
pp. 1161-1170 ◽  
Author(s):  
Ameen Ali Abu-Hashem ◽  
Rasha A. M. Faty
Keyword(s):  
Antimicrobial Activity ◽  
Mass Spectra ◽  
High Yield ◽  
Spectroscopic Techniques ◽  
Chemical Structures ◽  
Antibiotic Drugs ◽  
Antimicrobial Evaluation ◽  
Bacteria And Fungi ◽  
New Compounds

Background: 1, 3, 4-thiadiazoles, 1, 3, 4-thiadiazines and thienopyrimidines have newly attracted attention due to their forceful pharmacological activities. They showed antimicrobial, antiviral, analgesic and anti-inflammatory properties. Objective: The aim of this research is to synthesize new thiadiazolothienopyrimidines (2-10), thienopyrimidothiadiazines (11-15), quinoxaline-thienopyrimidinones (16) and thienopyrimido- thiadiazinoquinoxalinones (17) via effectual high yield procedure for assessing their antimicrobial activity. Method: A series of new 1, 3, 4-thiadiazolothienopyrimidines, thienopyrimidothiadiazines and thienopyrimidothiadiazinoquinoxalinones was prepared from 6-acetyl-3-amino-5-methyl-2-thioxo-2, 3-dihydrothieno [2, 3-d] pyrimidin-4(1H)-one (1) as the beginning material. Results: The 1, 3, 4-thiadiazoles, 1, 3, 4-thiadiazines derivatives (1-17) were synthesized in adequate to good yields (60-85%) in a stepwise effectual procedure under condition. The chemical structures of these new compounds were confirmed via many spectroscopic techniques as UV, IR, NMR, mass spectra and elemental analysis. In vitro, antimicrobial was evaluated for the synthesized compounds using minimal inhibitory concentration of these compounds against bacteria and fungi. Conclusion: The 1, 3, 4-thiadiazole and 1, 3, 4-thiadiazine derivatives (15-17) exhibited higher antimicrobial activity (Gram-positive, Gram-negative bacteria and fungi) compared with the standard antibiotic drugs; Levofloxacin (Tavanic) and Nystatin.

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