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.

scholarly journals Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽  
2020 ◽  
Vol 18 (8) ◽  
pp. 426 ◽  
Author(s):  
Senhua Chen ◽  
Yanlian Deng ◽  
Chong Yan ◽  
Zhenger Wu ◽  
Heng Guo ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
2D Nmr ◽  
X Ray ◽  
X Ray Crystallography ◽  
Spectroscopic Analyses ◽  
Structure Activity ◽  
Ic50 Values ◽  
Alternaria Sp ◽  
Modified Mosher’S Method ◽  
Oxide Inhibition

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

scholarly journals Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

Molecules ◽  
2019 ◽  
Vol 24 (17) ◽  
pp. 3186 ◽  
Author(s):  
Vasilyev ◽  
Bizyaev ◽  
Komarov ◽  
Gatilov ◽  
Tkachev
Keyword(s):  
Calculated Data ◽  
Transition Metal Ions ◽  
Synthetic Approach ◽  
Spectroscopic Methods ◽  
Aromatic Diamines ◽  
X Ray ◽  
X Ray Crystallography ◽  
Chemical Structures ◽  
Polydentate Ligands ◽  
New Compounds

A synthetic approach to a new group of stable chiral C2-symmetric diimines with the 4,5-diazafluorene core has been developed based on condensation of dipinodiazafluorene with aromatic diamines. The chemical structures of new compounds were proven by spectroscopic methods and X-ray crystallography. All the compounds form solvates with organic solvents (chloroform, benzene, 1,4-dioxane) and water. Specific spectral data of the new compounds are explained using calculated data (DFT). Diimines of the pinodiazafluorene series give colored reactions with transition metal ions and can be regarded as prospective polydentate ligands with interesting luminescent and chiroptical properties.

Nitric Oxide Inhibitory Activity of Xanthones from the Green Fruits of Cratoxylum formosum ssp. pruniflorum

2010 ◽  
Vol 63 (11) ◽  
pp. 1550 ◽  
Author(s):  
Nawong Boonnak ◽  
Achjana Khamthip ◽  
Chatchanok Karalai ◽  
Suchada Chantrapromma ◽  
Chanita Ponglimanont ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Antibacterial Activity ◽  
Inhibitory Activity ◽  
Spectroscopic Methods ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ic50 Values ◽  
Mic Value

Three new xanthones, pruniflorone M-O (1–3), and a new xanthonolignoid, 3-methoxy-5′-demethoxycadensin G (4), were isolated from the green fruits of Cratoxylum formosum ssp. pruniflorum along with three known xanthones (5–7) and a known flavonoid (8). Their structures were elucidated by spectroscopic methods and the structure of 1 was also determined by X-ray crystallography. Compounds 2 and 7 showed potent nitric oxide inhibitory activity with IC50 values of 4.4 and 4.3 μM, respectively. Moreover, 7 also showed strong antibacterial activity against both Gram-positive and Gram-negative bacteria with an MIC value of 4.67 μg mL–1.

scholarly journals Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 69 ◽  
Author(s):  
Kazuki Watanabe ◽  
Yoshihiro Mimaki ◽  
Haruhiko Fukaya ◽  
Yukiko Matsuo
Keyword(s):  
Spectroscopic Analysis ◽  
Apoptotic Cell ◽  
2D Nmr ◽  
Phytochemical Analysis ◽  
X Ray ◽  
C 23 ◽  
The Family ◽  
Ic50 Values ◽  
Cycloartane Glycosides ◽  
New Compounds

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

scholarly journals Broad-Spectrum Antiviral Natural Products from the Marine-Derived Penicillium sp. IMB17-046

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2821 ◽  
Author(s):  
Jiao Li ◽  
Yujia Wang ◽  
Xiaomeng Hao ◽  
Shasha Li ◽  
Jia Jia ◽  
...  
Keyword(s):  
Broad Spectrum ◽  
Influenza A ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Gastric Diseases ◽  
X Ray Crystallography ◽  
Penicillium Sp ◽  
Ic50 Values ◽  
Antiviral Activities ◽  
New Compounds

A new pyrazine derivative, trypilepyrazinol (1), a new α-pyrone polyketide, (+)-neocitreoviridin (2), and a new ergostane analogue, 3β-hydroxyergosta-8,14,24(28)-trien-7-one (3), were isolated and characterized along with five known compounds from the marine-derived fungus Penicillium sp. IMB17-046. The structures of these new compounds were determined using spectroscopic data analyses (HRESIMS, 1D- and 2D-NMR), X-ray crystallography analysis, and TDDFT ECD calculation. Compounds 1 and 3 exhibited broad-spectrum antiviral activities against different types of viruses, including human immunodeficiency virus (HIV), hepatitis C virus (HCV), and influenza A virus (IAV), with IC50 values ranging from 0.5 to 7.7 μM. Compounds 1 and 2 showed antibacterial activities against Helicobacter pylori, a causative pathogen of various gastric diseases, with minimum inhibitory concentration (MIC) values of 1–16 μg/mL.

scholarly journals Mechanistic Insights into the Chaperoning of Human Lysosomal-Galactosidase Activity: Highly Functionalized Aminocyclopentanes and C-5a-Substituted Derivatives of 4-epi-Isofagomine

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 4025
Author(s):  
Patrick Weber ◽  
Martin Thonhofer ◽  
Summer Averill ◽  
Gideon J. Davies ◽  
Andres Gonzalez Santana ◽  
...  
Keyword(s):  
Lysosomal Storage Diseases ◽  
Hydroxyl Group ◽  
Glycosidase Inhibitors ◽  
Lysosomal Storage ◽  
X Ray ◽  
Pharmacological Chaperones ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
New Compounds ◽  
Derivatives Of

Glycosidase inhibitors have shown great potential as pharmacological chaperones for lysosomal storage diseases. In light of this, a series of new cyclopentanoid β-galactosidase inhibitors were prepared and their inhibitory and pharmacological chaperoning activities determined and compared with those of lipophilic analogs of the potent β-d-galactosidase inhibitor 4-epi-isofagomine. Structure-activity relationships were investigated by X-ray crystallography as well as by alterations in the cyclopentane moiety such as deoxygenation and replacement by fluorine of a “strategic” hydroxyl group. New compounds have revealed highly promising activities with a range of β-galactosidase-compromised human cell lines and may serve as leads towards new pharmacological chaperones for GM1-gangliosidosis and Morquio B disease.

scholarly journals Metabolites from the Fungus Phoma sp. 7210, Associated with Aizoon Canariense

2010 ◽  
Vol 5 (8) ◽  
pp. 1934578X1000500
Author(s):  
Jingqiu Dai ◽  
Hidayat Hussain ◽  
Siegfried Dräger ◽  
Barbara Schulz ◽  
Tibor Kurtán ◽  
...  
Keyword(s):  
Solid State ◽  
Absolute Configuration ◽  
Endophytic Fungus ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Spectral Measurements ◽  
X Ray ◽  
Mass Spectral ◽  
X Ray Crystallography ◽  
Ray Geometry

A new metabolite, 3,16-diketoaphidicolan (1), was isolated together with four known compounds: aphidicolin (2), 17-acetyl-aphidicolin (3), (+)-eupenoxide (4), and phomoxanthone A (5) from the endophytic fungus Phoma sp. The structure of the new compound 1 was determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and by mass spectral measurements) and confirmed by X-ray crystallography. Its absolute configuration was assigned by means of the solid-state CD/TDDFT approach comparing the solid-state CD spectrum with the TDDFT-calculated one on the X-ray geometry.

scholarly journals Verruculosins A–B, New Oligophenalenone Dimers from the Soft Coral-Derived Fungus Talaromyces verruculosus

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 516 ◽  
Author(s):  
Minghui Wang ◽  
Longhe Yang ◽  
Liubin Feng ◽  
Fan Hu ◽  
Fang Zhang ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Spectroscopic Data ◽  
Soft Coral ◽  
Optical Rotation ◽  
Tyrosine Phosphatase ◽  
X Ray ◽  
X Ray Crystallography ◽  
Lead Compounds ◽  
Ic50 Values ◽  
New Compounds

In an effort to discover new bioactive anti-tumor lead compounds, a specific tyrosine phosphatase CDC25B and an Erb family receptor EGFR were selected as drug screening targets. This work led to the investigation of the soft coral-derived fungus Talaromyces verruculosus and identification of two new oligophenalenone dimers, verruculosins A–B (1–2), along with three known analogues, bacillisporin F (3), duclauxin (4), and xenoclauxin (5). Compound 1 was the first structure of the oligophenalenone dimer possessing a unique octacyclic skeleton. The detailed structures and absolute configurations of the new compounds were elucidated on the basis of spectroscopic data, X-ray crystallography, optical rotation, Electronic Circular Dichroism (ECD) analysis, and nuclear magnetic resonance (NMR) calculations. Among which, compounds 1, 3, and 5 exhibited modest inhibitory activity against CDC25B with IC50 values of 0.38 ± 0.03, 0.40 ± 0.02, and 0.26 ± 0.06 µM, respectively.

scholarly journals Structure Elucidation of Prenyl- and Geranyl-Substituted Coumarins in Gerbera piloselloides by NMR Spectroscopy, Electronic Circular Dichroism Calculations, and Single Crystal X-ray Crystallography

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1706
Author(s):  
Tuo Li ◽  
Xue Ma ◽  
Daniil Fedotov ◽  
Louise Kjaerulff ◽  
Karla Frydenvang ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Electronic Circular Dichroism ◽  
X Ray ◽  
X Ray Crystallography ◽  
New Type ◽  
New Compounds ◽  
Circular Dichroïsm ◽  
Substituted Coumarins

Crude ethyl acetate extract of Gerbera piloselloides (L.) Cass. was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. This indicated the presence of a series of unprecedented prenyl- and geranyl-substituted coumarin derivatives correlated with both α-glucosidase and PTP1B inhibitory activity. Repeated chromatographic separation targeting these compounds led to the isolation of 13 new compounds, of which ten could be isolated as both enantiomers after chiral separation. The structures of all isolated compounds were characterized by HRMS and extensive 1D and 2D NMR analysis. The absolute configurations of the isolated compounds were determined by comparison of experimental and calculated electronic circular dichroism spectra. Compound 6 features a rare furan-oxepane 5/7 ring system, possibly formed through addition of a geranyl unit to C-3 of 5-methylcoumarin, representing a new type of geranyl-substituted coumarin skeleton. Compounds 19 and 24 are the first examples of dimeric natural products consisting of both coumarin and chromone moieties.

scholarly journals Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽  
2020 ◽  
Vol 19 (1) ◽  
pp. 9
Author(s):  
Ya-Ping Liu ◽  
Sheng-Tao Fang ◽  
Zhen-Zhen Shi ◽  
Bin-Gui Wang ◽  
Xiao-Nian Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Penicillium Oxalicum ◽  
Marine Phytoplankton ◽  
Cold Seep ◽  
Phytoplankton Species ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

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