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 New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 688
Author(s):  
Kim-Thao Le ◽  
Jan J. Bandolik ◽  
Matthias U. Kassack ◽  
Kenneth R. Wood ◽  
Claudia Paetzold ◽  
...  
Keyword(s):  
Ovarian Cancer Cell Line ◽  
Hawaiian Island ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time ◽  
Modified Mosher’S Method

The dichloromethane extract from leaves of Melicope barbigera (Rutaceae), endemic to the Hawaiian island of Kaua’i, yielded four new and three previously known acetophenones and 2H-chromenes, all found for the first time in M. barbigera. The structures of the new compounds obtained from the dichloromethane extract after purification by chromatographic methods were unambiguously elucidated by spectroscopic analyses including 1D/2D NMR spectroscopy and HRESIMS. The absolute configuration was determined by modified Mosher’s method. Compounds 2, 4 and the mixture of 6 and 7 exhibited moderate cytotoxic activities against the human ovarian cancer cell line A2780 with IC50 values of 30.0 and 75.7 µM for 2 and 4, respectively, in a nuclear shrinkage cytotoxicity assay.

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 Apoptotic Activity of New Oxisterigmatocystin Derivatives from the Marine-Derived Fungus Aspergillus nomius NC06

Marine Drugs ◽  
2021 ◽  
Vol 19 (11) ◽  
pp. 631
Author(s):  
Muh. Ade Artasasta ◽  
Yanwirasti Yanwirasti ◽  
Muhammad Taher ◽  
Akmal Djamaan ◽  
Ni Putu Ariantari ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Compounds ◽  
Ic50 Values ◽  
Rice Medium ◽  
Double Staining Method ◽  
Aspergillus Nomius ◽  
Apoptotic Activity ◽  
Ht 29

Sponge-derived fungi have recently attracted attention as an important source of interesting bioactive compounds. Aspergillus nomius NC06 was isolated from the marine sponge Neopetrosia chaliniformis. This fungus was cultured on rice medium and yielded four compounds including three new oxisterigmatocystins, namely, J, K, and L (1, 2, and 3), and one known compound, aspergillicin A (4). Structures of the compounds were elucidated by 1D and 2D NMR spectroscopy and by high-resolution mass spectrometry. The isolated compounds were tested for cytotoxic activity against HT 29 colon cancer cells, where compounds 1, 2, and 4 exhibited IC50 values of 1.21, 2.23, and 5.62 µg/mL, respectively. Under the fluorescence microscope by using a double staining method, HT 29 cells were observed to be viable, apoptotic, and necrotic after treatment with the cytotoxic compounds 1, 2, and 4. The result shows that compounds 1 and 2 were able to induce apoptosis and cell death in HT 29 cells.

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.

Non-Alkaloidal Compounds from the Bulbs of the Egyptian Plant Pancratium maritimum

2014 ◽  
Vol 69 (3-4) ◽  
pp. 92-98 ◽  
Author(s):  
Sabrin R. M. Ibrahim ◽  
Gamal A. Mohamed ◽  
Lamiaa A. Shaala ◽  
Diaa T. A. Youssef
Keyword(s):  
Cancer Cell Line ◽  
Prostate Cancer Cell Line ◽  
2D Nmr ◽  
Positive Control ◽  
Structure Identification ◽  
2D Nmr Spectroscopy ◽  
Mass Spectral ◽  
Phytochemical Investigation ◽  
New Compounds ◽  
Pancratium Maritimum

Phytochemical investigation of the cytotoxic fractions of fresh bulbs of Pancratium maritimum L. led to the isolation and structure identification of two new compounds, pancricin (1) and pancrichromone (4), together with four known compounds, including 2,4-dihydroxy-6- methoxy-3-methyl acetophenone (2), 5-formylfurfuryl acetate (3), 7-β-D-glucosyloxy-5-hydroxy-2- methylchromone (5), and ethyl-b-D-glucopyranoside (6). Their structures were established on the basis of 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC, and HMBC), as well as HR mass spectral analyses. The compounds were evaluated for their antimigratory and antiproliferative activities against the highly metastatic human prostate cancer cell line (PC-3M). Compound 5 was the most active compound displaying good activity in the proliferation assay comparable to that of the positive control 4-hydroxyphenylmethylene hydantoin, while it displayed only weak antimigratory activity compared to the positive control 4-ethylmercaptophenylmethylene hydantoin.

scholarly journals 5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid

Molbank ◽  
10.3390/m1238 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1238
Author(s):  
Ion Burcă ◽  
Valentin Badea ◽  
Calin Deleanu ◽  
Vasile-Nicolae Bercean
Keyword(s):  
Chemical Structure ◽  
Functional Group ◽  
Coupling Reaction ◽  
2D Nmr ◽  
Azo Coupling ◽  
2D Nmr Spectroscopy ◽  
Azo Compound ◽  
Ft Ir ◽  
New Compounds ◽  
Carboxylic Functional Group

A new azo compound was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound was hydrolyzed and thus a new chemical structure with a carboxylic functional group resulted. The structures of the new compounds were fully characterized by: UV–Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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).

scholarly journals Cryptic Secondary Metabolites from the Sponge-Associated Fungus Aspergillus ochraceus

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 99 ◽  
Author(s):  
Marian Frank ◽  
Ferhat Özkaya ◽  
Werner Müller ◽  
Alexandra Hamacher ◽  
Matthias Kassack ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Carcinoma Cells ◽  
Aspergillus Ochraceus ◽  
Nitrobenzoic Acid ◽  
Ovarian Carcinoma Cells ◽  
White Bean ◽  
Ic50 Values ◽  
Rice Medium ◽  
Human Ovarian Carcinoma ◽  
New Compounds

The fungus Aspergillus ochraceus was isolated from the Mediterranean sponge Agelas oroides. The initial fermentation of the fungus on solid rice medium yielded 16 known compounds (4–19). The addition of several inorganic salts to the rice medium mainly influenced the accumulation of these secondary metabolites. Fermentation of the fungus on white bean medium yielded the new waspergillamide B (1) featuring an unusual p-nitrobenzoic acid as partial structure. Moreover, two new compounds, ochraspergillic acids A and B (2 and 3), which are both adducts of dihydropenicillic acid and o- or p-aminobenzoic acid, were isolated from the co-culture of the fungus with Bacillus subtilis. Compound 2 was also detected in axenic fungal cultures following the addition of either anthranilic acid or tryptophan to the rice medium. The structures of the new compounds were established by 1D and 2DNMR experiments as well as from the HRMS data. The absolute configuration of 1 was elucidated following hydrolysis and derivatization of the amino acids using Marfey’s reagent. Viomellein (9) and ochratoxin B (18) exhibited strong cytotoxicity against the A2780 human ovarian carcinoma cells with IC50 values of 5.0 and 3.0 µM, respectively.

scholarly journals Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1440
Author(s):  
Alla A. Kicha ◽  
Dinh T. Ha ◽  
Timofey V. Malyarenko ◽  
Anatoly I. Kalinovsky ◽  
Roman S. Popov ◽  
...  
Keyword(s):  
Coastal Waters ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Effects ◽  
One Dimensional ◽  
The Common ◽  
Polyhydroxylated Steroids ◽  
New Compounds ◽  
Ht 29 ◽  
Inhibit Cell Proliferation

Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

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