scholarly journals New Antifungal Metabolites from the Mariana Trench Sediment-Associated Actinomycete Streptomyces sp. SY1965

Marine Drugs ◽  
2020 ◽  
Vol 18 (8) ◽  
pp. 385 ◽  
Author(s):  
Wenwen Yi ◽  
Le Qin ◽  
Xiao-Yuan Lian ◽  
Zhizhen Zhang
Keyword(s):  
High Performance ◽  
Nuclear Overhauser Effect ◽  
Ionization Mass ◽  
Mariana Trench ◽  
Streptomyces Sp ◽  
Antifungal Metabolites ◽  
Ionization Mass Spectroscopy ◽  
Noesy Experiment ◽  
Nuclear Overhauser ◽  
New Compounds

New streptothiazolidine A (1), streptodiketopiperazines A (2) and B (3), and (S)-1-(3-ethylphenyl)-1,2-ethanediol (4), together with eight known compounds (5–12), were isolated from the Mariana Trench sediment-associated actinomycete Streptomyces sp. SY1965. The racemic mixtures of (±)-streptodiketopiperazine (2 and 3) and (±)-1-(3-ethylphenyl)-1,2-ethanediol (4 and 5) were separated on a chiral high-performance liquid chromatography (HPLC) column. Structures of the new compounds were elucidated by their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data and extensive nuclear magnetic resonance (NMR) spectroscopic analyses. Streptothiazolidine A is a novel salicylamide analogue with a unique thiazolidine-contained side chain and its absolute configuration was established by a combination of nuclear Overhauser effect spectroscopy (NOESY) experiment, electronic circular dichroism (ECD) and 13C NMR calculations. New streptothiazolidine A (1) and streptodiketopiperazines A (2) and B (3) showed antifungal activity against Candida albicans with MIC values of 47, 42, and 42 g/mL, respectively.

scholarly journals New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 483
Author(s):  
Kuo Yong ◽  
Sidra Kaleem ◽  
Bin Wu ◽  
Zhizhen Zhang
Keyword(s):  
Chemical Degradation ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
Penicillium Sp ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Rice Medium ◽  
Antiglioma Activity ◽  
New Compounds

Seven novel compounds, namely peniresorcinosides A–E (1–5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8–17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

scholarly journals Antibacterial Meroterpenoids, Merochlorins G–J from the Marine Bacterium Streptomyces sp.

Marine Drugs ◽  
2021 ◽  
Vol 19 (11) ◽  
pp. 618
Author(s):  
Min-Ji Ryu ◽  
Prima F. Hillman ◽  
Jihye Lee ◽  
Sunghoon Hwang ◽  
Eun-Young Lee ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Nuclear Overhauser Effect ◽  
Antibacterial Activities ◽  
Streptomyces Sp ◽  
Overhauser Effect ◽  
Planar Structures ◽  
Value Range ◽  
Bacterium Strain ◽  
Nuclear Overhauser ◽  
And Staphylococcus Aureus

Four new chlorinated meroterpenoids, merochlorins G−J (1−4), and 10, a dihydronaphthalenedione precursor, along with known merochlorins A (5) and C−F (6−9), were obtained from cultivation of the bacterium strain Streptomyces sp. CNH-189, which was isolated from marine sediment. The planar structures of compounds 1−4 and 10 were elucidated by interpretation of MS, UV, and NMR spectroscopic data. The relative configurations of compounds 1−4 were determined via analysis of nuclear Overhauser effect (NOE) spectroscopic data, after which their absolute configurations were established by comparing the experimental electronic circular dichroism (ECD) spectra of compounds 1−4 to those of previously reported possible enantiomer models and DP4 calculations. Compound 3 displayed strong antibacterial activities against Bacillus subtilis, Kocuria rhizophila, and Staphylococcus aureus, with MIC values of 1, 2, and 2 μg/mL, respectively, whereas compound 1 exhibited weak antibacterial effects on these three strains, with a 16−32 μg/mL MIC value range.

Antiprotozoal Diterpenes from Perovskia abrotanoides

Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 913-919 ◽  
Author(s):  
Marzieh Tabefam ◽  
Mahdi Farimani ◽  
Ombeline Danton ◽  
Justine Ramseyer ◽  
Marcel Kaiser ◽  
...  
Keyword(s):  
High Performance ◽  
Leishmania Donovani ◽  
Ionization Mass ◽  
Trypanosoma Brucei Rhodesiense ◽  
Selective Toxicity ◽  
L6 Cells ◽  
Aerial Parts ◽  
New Compounds ◽  
Perovskia Abrotanoides ◽  
Ethyl Acetate Extracts

AbstractAs part of a screening for new antiparasitic natural products from Iranian plants, n-hexane and ethyl acetate extracts from the aerial parts of Perovskia abrotanoides were found to exhibit strong inhibitory activity against Trypanosoma brucei rhodesiense and Leishmania donovani. The activity was tracked by high-performance liquid chromatography (HPLC)-based activity profiling. Preparative isolation by a combination of silica gel column chromatography and HPLC afforded 17 diterpenoids (1–17), including 14 abietane-, two icetexane-, and one isopimarane-type derivatives. Among these, (5R,10S)-11-hydroxy-12-methoxy-20-norabieta-8,11,13-triene (2), 12-hydroxy-norabieta-1(10),8,11,13-tetraene-1,11-furan (6), and 12-methoxybarbatusol (9) were new compounds, the structure of which was established by comprehensive spectroscopic data analysis (one- and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectrometry, electronic circular dichroism). The antiprotozoal activity of the isolated compounds was evaluated against T. b. rhodesiense, Trypanosoma cruzi, L. donovani, and Plasmodium falciparum. Selectivity indexes (SI) were calculated in comparison to cytotoxicity on rat myoblast (L6) cells. Particularly active were 7α-ethoxyrosmanol (4) with an IC50 of 0.8 µM against T. b. rhodesiense (SI 14.9) and an IC50 of 1.8 µM (SI 6.9) against L. donovani, ferruginol (8) with an IC50 of 2.9 µM (SI 19.2) against P. falciparum, and miltiodiol (10) with an IC50 of 0.5 µM (SI 10.5) against T. b. rhodesiense. None of the compounds exhibited selective toxicity against T. cruzi (SI ≤ 1.6).

scholarly journals Two New Compounds from Rhizomes of Musa basjoo

2019 ◽  
Vol 14 (12) ◽  
pp. 1934578X1989343
Author(s):  
Li Jiang ◽  
Yang Wang ◽  
Min-Hui Zhu ◽  
Lin Zheng ◽  
Lin-Zhen Li ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Carboxylic Acid ◽  
High Resolution ◽  
Spectroscopic Analysis ◽  
Acid Ethyl Ester ◽  
Ethanol Extract ◽  
Ionization Mass ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
New Compounds

Two new compounds, rel-(3 S,4a R,10b R)-3-(4′-methoxyphenyl)-8-hydroxy-9-methoxy-4a,5,6,10b-tetrahydro-3 H-naphtho[2,1-b]pyran (1), 7-hydroxy- 2-phenylnaphthalene-1-carboxylic acid ethyl ester (2), were isolated from the 70% ethanol extract of the rhizomes of Musa basjoo. Their structures were determined on the basis of spectroscopic analysis including 1-dimensional (1D), 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectroscopy.

scholarly journals Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4192
Author(s):  
Zhe Guo ◽  
Zhong-Mei Zou
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
Chemical Diversity ◽  
Ionization Mass ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Planar Structures ◽  
Ionization Mass Spectroscopy ◽  
Epigenetic Manipulation ◽  
New Compounds ◽  
Mcf 7

Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), and two known compounds, pestaloficin C (3) and arthrinone (4). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds 1–2 were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.

scholarly journals ELECTROSPRAY IONIZATION MASS SPECTROMETRY FRAGMENTATION PATHWAYS OF SALTS OF SOME 1,2,4-TRIAZOLYLTHIOACETATE ACIDS, THE ACTIVE PHARMACEUTICAL INGREDIENTS

2018 ◽  
Vol 11 (10) ◽  
pp. 303
Author(s):  
Varynskyi Borys ◽  
Kaplaushenko Andriy ◽  
Parchenko Vladymyr
Keyword(s):  
Electrospray Ionization ◽  
High Performance ◽  
Pharmaceutical Formulations ◽  
Ionization Mass ◽  
Active Pharmaceutical Ingredients ◽  
Ionization Source ◽  
Fragmentation Pathways ◽  
Pharmaceutical Ingredients ◽  
Fragmentation Patterns ◽  
New Compounds

Objective: The goal of this research was to study fragmentation pathways of series salts of 1,2,4-triazolylthioacetate acids. Methods: The study was done in the Electrospray ionization source with single quadrupole mass spectrometer Agilent 6120 after elution through column Zorbax SB-C18, 30 mm × 4.6 mm, 1.8 μm at Agilent 1260 infinity high-performance liquid chromatography system. The series salts of 1,2,4-triazolylthioacetate acids were studied. These salts are active pharmaceutical ingredients of potential or registered pharmaceutical formulations. Results: The mass spectra of corresponding compounds have analyzed. The fragmentation patterns of these compounds decay have proposed. Conclusions: Studying the fragmentation of the indicated substances can be used for detecting the mentioned substances, as well as for confirming the structure of new compounds with the mass spectrum based on the patterns described above.

scholarly journals Antileishmanial Activity of Flavones-Rich Fraction From Arrabidaea chica Verlot (Bignoniaceae)

2021 ◽  
Vol 12 ◽  
Author(s):  
João Victor Silva-Silva ◽  
Carla Junqueira Moragas-Tellis ◽  
Maria do Socorro dos Santos Chagas ◽  
Paulo Victor Ramos de Souza ◽  
Celeste da Silva Freitas de Souza ◽  
...  
Keyword(s):  
High Performance ◽  
Peritoneal Macrophages ◽  
Ultrastructural Changes ◽  
Ionization Mass ◽  
Griess Reagent ◽  
Transmission Electron ◽  
Arrabidaea Chica ◽  
New Compounds ◽  
Hydroethanolic Extract

Acknowledging the need of identifying new compounds for the treatment of leishmaniasis, this study aimed to evaluate, from in vitro trials, the activity of flavones from Arrabidaea chica against L. amazonensis. The chromatographic profiles of the hydroethanolic extract and a flavone-rich fraction (ACFF) from A. chica were determined by high-performance liquid chromatography coupled with a diode-array UV-Vis detector (HPLC-DAD-UV) and electrospray ionization mass spectrometry in tandem (LC-ESI-MS-MS). The flavones luteolin (1) and apigenin (2), isolated from chromatographic techniques and identified by Nuclear Magnetic Resonance of 1H and 13C, were also quantified in ACFF, showing 190.7 mg/g and apigenin 12.4 mg/g, respectively. The other flavones were identified by comparing their spectroscopic data with those of the literature. The in vitro activity was assayed against promastigotes and intramacrophagic amastigote forms of L. amazonensis. Cytotoxicity tests were performed with peritoneal macrophages of BALB/c mice. Nitrite quantification was performed with Griess reagent. Ultrastructural investigations were obtained by transmission electron microscopy. Anti-Leishmania assays indicated that the IC50 values for ACFF, apigenin, and luteolin were obtained at 40.42 ± 0.10 and 31.51 ± 1.13 μg/mL against promastigotes, respectively. ACFF and luteolin have concentration-dependent cytotoxicity. ACFF and luteolin also inhibited the intra-macrophagic parasite (IC50 3.575 ± 1.13 and 11.78 ± 1.24 μg/mL, respectively), with a selectivity index of 11.44 for ACFF. Promastigotes exposed to ACFF and luteolin exhibited ultrastructural changes, such as intense cytoplasm vacuolization and mitochondrial swelling. These findings data evidence the antileishmanial action of flavone-rich fractions of A. chica against L. amazonensis, encouraging further studies.

scholarly journals Bioactive Metabolites from the Mariana Trench Sediment-Derived Fungus Penicillium sp. SY2107

Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 258 ◽  
Author(s):  
Sidra Kaleem ◽  
Le Qin ◽  
Wenwen Yi ◽  
Xiao-Yuan Lian ◽  
Zhizhen Zhang
Keyword(s):  
Antimicrobial Activities ◽  
Bioactive Metabolites ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
Mariana Trench ◽  
Penicillium Sp ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Rice Medium ◽  
Trench Sediments

Mariana Trench sediments are enriched in microorganisms, however, the structures and bioactivities of their secondary metabolites are not very known. In this study, a fungus Penicillium sp. SY2107 was isolated from a sample of Mariana Trench sediment collected at a depth of 11000 m and an extract prepared from the culture of this fungus in rice medium showed antimicrobial activities. Chemical investigation on this active extract led to the isolation of 16 compounds, including one novel meroterpenoid, named andrastone C. Structure of the new compound was elucidated based on high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses and a single crystal X-ray diffraction. The crystal structure of a known meroterpenoid andrastone B was also reported in this study. Both andrastones B and C exhibited antimicrobial activities against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, and Candida albicans with minimum inhibitory concentration (MIC) values in a range from 6 to 13 μg/mL.

scholarly journals Acylated Aminooligosaccharides with Inhibitory Effects against α-Amylase from Streptomyces sp. HO1518

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 403 ◽  
Author(s):  
Hai-Li Liu ◽  
Heng-Chao E ◽  
Ding-An Xie ◽  
Wen-Bo Cheng ◽  
Wan-Qi Tao ◽  
...  
Keyword(s):  
Type Ii Diabetes ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
Streptomyces Sp ◽  
Nmr Data ◽  
New Compounds ◽  
Drug Leads ◽  
Clinical Drug

Five new acylated aminooligosaccharides (1–5), together with one known related analogue (6), were isolated from Streptomyces sp. HO1518. Their structure was identified by extensive spectroscopic analysis, including 1D and 2D NMR data and high resolution electrospray ionization mass spectrometry (HRESIMS), and by comparison with those reported in the literature. All of the new compounds showed more promising porcine pancreatic α-amylase (PPA) inhibitory activities than the clinical drug acarbose, indicating them as potential pharmaceutical drug leads toward type II diabetes.

scholarly journals Stereochemical Investigations of Diastereomeric N-[2-(Aryl)-5-methyl-4-oxo-1,3-thiazolidine-3-yl]-pyridine-3-carboxamides by Nuclear Magnetic Resonance Spectroscopy (1D and 2D)

2015 ◽  
Vol 2015 ◽  
pp. 1-9 ◽  
Author(s):  
Öznur Demir-Ordu ◽  
Hale Demir-Dündar ◽  
Sumru Ozkirimli
Keyword(s):  
High Performance ◽  
Mass Spectra ◽  
Chiral Stationary Phase ◽  
Coupling Constants ◽  
Resonance Spectroscopy ◽  
H Nmr ◽  
Nuclear Overhauser Enhancement ◽  
Stereogenic Centers ◽  
Noesy Experiment ◽  
Nuclear Overhauser

Some new N-[2-(aryl)-5-methyl-4-oxo-1,3-thiazolidine-3-yl]-pyridine-3-carboxamides were synthesized and their structures were investigated by IR, NMR (1H, 13C, and 2D), and mass spectra. The presence of C-2 and C-5 stereogenic centers on the thiazolidinone ring resulted in diastereoisomeric pairs. The configurations of two stereogenic centers were assigned based upon 1H NMR analysis of coupling constants and 2D nuclear overhauser enhancement spectroscopy (NOESY) experiment. Resolution of the diastereoisomers was performed by high performance liquid chromatography (HPLC) using a chiral stationary phase.

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