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 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 Novel Bioactive Penicipyrroether A and Pyrrospirone J from the Marine-Derived Penicillium sp. ZZ380

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 292 ◽  
Author(s):  
Tengfei Song ◽  
Mingmin Tang ◽  
Hengju Ge ◽  
Mengxuan Chen ◽  
Xiaoyuan Lian ◽  
...  
Keyword(s):  
Inhibitory Concentration ◽  
Structural Type ◽  
Ionization Mass ◽  
Isolation And Identification ◽  
Penicillium Sp ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Fused Ring ◽  
Ic50 Values ◽  
Fused Ring System

The marine-sourced fungus Penicillium sp. ZZ380 was previously reported to have the ability to produce a series of new pyrrospirone alkaloids. Further investigation on this strain resulted in the isolation and identification of novel penicipyrroether A and pyrrospirone J. Each of them represents the first example of its structural type, with a unique 6/5/6/5 polycyclic fusion that is different from the 6/5/6/6 fused ring system for the reported pyrrospirones. Their structures were elucidated by extensive nuclear magnetic resonance (NMR) and high resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic analyses, electronic circular dichroism (ECD) and 13C NMR calculations and X-ray single crystal diffraction. Penicipyrroether A showed potent antiproliferative activity against human glioma U87MG and U251 cells with half maximal inhibitory concentration (IC50) values of 1.64–5.50 μM and antibacterial inhibitory activity with minimum inhibitory concentration (MIC) values of 1.7 μg/mL against methicillin-resistant Staphylococcus aureus and 3.0 μg/mL against Escherichia coli.

scholarly journals Two New Neo-debromoaplysiatoxins—A Pair of Stereoisomers Exhibiting Potent Kv1.5 Ion Channel Inhibition Activities

Marine Drugs ◽  
2019 ◽  
Vol 17 (12) ◽  
pp. 652 ◽  
Author(s):  
Ting-Ting Fan ◽  
Hui-Hui Zhang ◽  
Yang-Hua Tang ◽  
Fan-Zhong Zhang ◽  
Bing-Nan Han
Keyword(s):  
Atomic Orbital ◽  
Ionization Mass ◽  
Spectroscopic Techniques ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Channel Inhibition ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Novel Structures ◽  
Absolute Stereochemistry ◽  
Shift Calculation

A pair of stereoisomers possessing novel structures with 6/6/5 fused-ring systems, neo-debromoaplysiatoxin E (1) and neo-debromoaplysiatoxin F (2), were isolated from the marine cyanobacterium Lyngbya sp. Their structures were elucidated using various spectroscopic techniques including high resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR). The absolute stereochemistry was determined by calculated electronic circular dichroism (ECD) and gauge-independent atomic orbital (GIAO) NMR shift calculation followed by DP4+ analysis. Significantly, this is the first report on aplysiatoxin derivatives with different absolute configurations at C9–C12 (1: 9S, 10R, 11S, 12S; 2: 9R, 10S, 11R, 12R). Compounds 1 and 2 exhibited potent blocking activities against Kv1.5 with IC50 values of 1.22 ± 0.22 μM and 2.85 ± 0.29 μM, respectively.

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 Azaphilones from the Red Sea Fungus Aspergillus falconensis

Marine Drugs ◽  
2020 ◽  
Vol 18 (4) ◽  
pp. 204 ◽  
Author(s):  
Dina H. El-Kashef ◽  
Fadia S. Youssef ◽  
Rudolf Hartmann ◽  
Tim-Oliver Knedel ◽  
Christoph Janiak ◽  
...  
Keyword(s):  
Red Sea ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
X Ray Diffraction ◽  
2D Nmr Spectroscopy ◽  
Nmr Data ◽  
Ic50 Values ◽  
Rice Medium ◽  
Optical Rotations ◽  
New Compounds

The marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Canyon at Dahab, Red Sea, yielded two new chlorinated azaphilones, falconensins O and P (1 and 2) in addition to four known azaphilone derivatives (3−6) following fermentation of the fungus on solid rice medium containing 3.5% NaCl. Replacing NaCl with 3.5% NaBr induced accumulation of three additional new azaphilones, falconensins Q−S (7−9) including two brominated derivatives (7 and 8) together with three known analogues (10−12). The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopy and HRESIMS data as well as by comparison with the literature. The absolute configuration of the azaphilone derivatives was established based on single-crystal X-ray diffraction analysis of 5, comparison of NMR data and optical rotations as well as on biogenetic considerations. Compounds 1, 3−9, and 11 showed NF-κB inhibitory activity against the triple negative breast cancer cell line MDA-MB-231 with IC50 values ranging from 11.9 to 72.0 µM.

scholarly journals Potential Antiviral Xanthones from a Coastal Saline Soil Fungus Aspergillus iizukae

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 449 ◽  
Author(s):  
Hui-Hui Kang ◽  
Huai-Bin Zhang ◽  
Mei-Jia Zhong ◽  
Li-Ying Ma ◽  
De-Sheng Liu ◽  
...  
Keyword(s):  
Saline Soil ◽  
Soil Fungus ◽  
Ionization Mass ◽  
Strong Activity ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Coastal Saline Soil ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Simplex Virus ◽  
Relationship Of

Five new (1–5) and two known xanthones (6 and 7), one of the latter (6) obtained for the first time as a natural product, together with three known anthraquinones, questin, penipurdin A, and questinol, were isolated from the coastal saline soil-derived Aspergillus iizukae by application of an OSMAC (one strain many compounds) approach. Their structures were determined by interpretation of nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, as well as comparison of these data with those of related known compounds. Antiviral activity of xanthones 1−7 was evaluated through the cytopathic effect (CPE) inhibition assay, and compound 2 exhibited distinctly strong activity towards influenza virus (H1N1), herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) with IC50 values of 44.6, 21.4, and 76.7 μM, respectively, which indicated that it was worth to further investigate it as a potential lead compound. The preliminary structure-activity relationship of the xanthones is discussed.

scholarly journals Fe(III)-doxycycline complexes with diimine ligands: Syntheses, characterization and biological properties

2019 ◽  
Vol 38 (1) ◽  
pp. 29
Author(s):  
Joshua A Obaleye ◽  
Olufunso Olumide Abosede
Keyword(s):  
Binding Constants ◽  
Biological Properties ◽  
Axial Position ◽  
Klebsiella Pneumonia ◽  
Ionization Mass ◽  
Polypyridyl Ligands ◽  
Diimine Ligands ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Ct Dna

Three new iron(III) complexes of doxycycline viz: [Fe(dox)2Cl]Cl2 (1), [Febpy(dox)Cl]Cl2 (2) and [Fephen(dox)Cl]Cl2 (3), where dox is doxycycline, bpy is 2,2ʹ-bipyridine and phen is 1,10-phenanthroline, were synthesized and characterized by elemental analysis, electronic absorption, FT-IR, and electrospray ionization mass spectroscopy. Doxycycline and the polypyridyl ligands behave as bidendate ligands; the polypyridyl ligands coordinate through the two diimine nitrogen atoms and doxycycline through enolate and diketoamide oxygen atoms of ring A in a five-coordinate system with chloride atom in the axial position. Their antibacterial and antiplasmodial activities against chloroquine-sensitive Plasmodium falciparum NF54 and their interaction with calf thymus (CT) DNA using electronic titration were investigated. The three complexes showed good activity against strains of Staphylococcus aureus and Klebsiella pneumonia. The complexes bind moderately to CT DNA with binding constants of 5.6 × 104 and 4.8 × 104 for complexes 2 and 3, respectively.

Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

Planta Medica ◽  
2021 ◽  
Author(s):  
Julianna Max ◽  
Jörg Heilmann
Keyword(s):  
Petroleum Ether Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Ionization Mass ◽  
2D Nmr Spectroscopy ◽  
Vitro Assay ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Adamantane Skeleton

Abstract 1H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1–14), while 5 further compounds showed an adamantane skeleton (15–19). Except for hookerione C (15), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other Hypericum species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Taeniocarpium Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based in vitro assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC50 values in the range ~ 3 – 22 µM, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-α-induced ICAM-1 expression was determined for 1 – 5, 7, and 10 – 12. Substances 3 and 12 reduced the ICAM-1 expression significantly (to 46.7% of control for 3, 62.3% for 12, at 50 µM).

Sign in / Sign up

Export Citation Format

Share Document