Resorcylic Acid Lactones Produced by an Endophytic Penicillium ochrochloron Strain from Kadsura angustifolia

Planta Medica ◽  
2020 ◽  
Author(s):  
Hong Chuan Song ◽  
Dan Qin ◽  
Hai Yang Liu ◽  
Jin Yan Dong ◽  
Chuan You ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Tumor Cell Line ◽  
Antibacterial Activities ◽  
Preparative Hplc ◽  
Solid Culture ◽  
Ic50 Value ◽  
Resorcylic Acid Lactones ◽  
New Compounds ◽  
First Time

AbstractFour new β-resorcylic acid lactones, including penochrochlactone A (2), 4-O-desmethyl-aigialomycin B (4), and penochrochlactones C and D (5 and 6), two compounds isolated from a natural source for the first time, 5α, 6β-acetonide-aigialomycin B (1) and penochrochlactone B (3), together with six known compounds, aigialomycin F (7), aigialomycins A, B, and D (8–10), zeaenol (11), and oxozeaenol (12), were isolated from a mycelial solid culture of the endophytic fungus Penicillium ochrochloron SWUKD4.1850 from the medicinal plant Kadsura angustifolia by sequential purification over silica gel, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were elucidated by extensive spectroscopic analysis and chemical conversions. In addition, all the new compounds were evaluated for their cytotoxic and antibacterial activities in vitro. Penochrochlactone C (5) displayed moderate cytotoxicity against the HeLa tumor cell line with an IC50 value of 9.70 µM. In the antibacterial assays, compounds 4 – 6 exhibited moderate activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa with MIC values between 9.7 and 32.0 µg/mL.

scholarly journals Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2862
Author(s):  
Christine C. Waleguele ◽  
Brice M. Mba’ning ◽  
Angelbert F. Awantu ◽  
Jean J. K. Bankeu ◽  
Yannick S. F. Fongang ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
Trypanosoma Brucei Brucei ◽  
Preliminary Screening ◽  
Nmr Data ◽  
Antitrypanosomal Activity ◽  
Phytochemical Investigation ◽  
Ic50 Value ◽  
New Compounds ◽  
First Time

The MeOH/CH2Cl2 (1:1) extracts of the roots and leaves of Beilschmiedia louisii and B. obscura showed potent antitrypanosomal activity during preliminary screening on Trypanosoma brucei brucei. Phytochemical investigation of these extracts led to the isolation of a mixture of two new endiandric acid derivatives beilschmiedol B (1) and beilschmiedol C (2), and one new phenylalkene obscurene A (3) together with twelve known compounds (4–15). In addition, four new derivatives (11a–11d) were synthesized from compound 11. Their structures were elucidated based on their NMR and MS data. Compounds 5, 6, and 7 were isolated for the first time from the Beilschmiedia genus. Additionally, the NMR data of compound 4 are given here for the first time. The isolates were evaluated for their antitrypanosomal and antimalarial activities against Tb brucei and the Plasmodium falciparum chloroquine-resistant strain Pf3D7 in vitro, respectively. From the tested compounds, the mixture of new compounds 1 and 2 exhibited the most potent antitrypanosomal activity in vitro with IC50 value of 4.91 μM.

scholarly journals Secondary Metabolites with Antimicrobial Activities from Chamaecyparis obtusa var. formosana

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 429
Author(s):  
Ming-Der Wu ◽  
Ming-Jen Cheng ◽  
Jih-Jung Chen ◽  
Nanthaphong Khamthong ◽  
Wen-Wei Lin ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
High Resolution Mass Spectrometry ◽  
Chamaecyparis Obtusa ◽  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
The Past ◽  
Nmr Data ◽  
The Mean ◽  
New Compounds ◽  
First Time

Seven new compounds, including one dimer novel skeleton, chamaecyformosanin A (1); three diterpenes, chamaecyformosanins B–D (2-4); one sesquiterpene, chamaecyformosanin E (5); and two monoterpenes, chamaecyformosanins F and G (6 and 7) were isolated from the methanol extract of the bark of Chamaecyparis obtusa var. formosana. Their structures were established by the mean of spectroscopic analysis and the comparison of NMR data with those of known analogues. Their structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry. Furthermore, the isolated compounds were subjected to an evaluation of their antimicrobial activity. Metabolites 1, 3, and 4 present antibacterial activities. It is worth mentioning that the chemical composition of the bark of C. obtusa var. formosana has never been studied in the past. This is the first time the barks from C. obtusa var. formosana were studied and two new skeleton compounds, 1 and 7, were obtained.

scholarly journals New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 478 ◽  
Author(s):  
Runlin Cai ◽  
Hongming Jiang ◽  
Zhenming Zang ◽  
Chunyuan Li ◽  
Zhigang She
Keyword(s):  
Inhibitory Activity ◽  
Pathogenic Bacteria ◽  
Data Interpretation ◽  
Antibacterial Activities ◽  
Vitro Assay ◽  
E Coli ◽  
Ic50 Value ◽  
Aspergillus Sp ◽  
New Compounds

Three new benzofuranoids, asperfuranoids A–C (1–3), two new phenylpropanoid derivatives (6 and 7), and nine known analogues (4, 5, and 8–14) were isolated from the liquid substrate fermentation cultures of the mangrove endopytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were determined by extensive spectroscopic data interpretation. The absolute configurations of 1–3 were assigned via the combination of Mosher’s method, and experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 were a pair of enantiomers and their absolute configurations were established for the first time on the basis of their ECD spectra aided with ECD calculations. All isolated compounds (1–14) were evaluated for their enzyme inhibitory activity against α-glucosidase and antibacterial activities against four pathogenic bacteria (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa). Among them, compound 6 exhibited potent inhibitory activity against α-glucosidase in a standard in vitro assay, with an IC50 value of 12.4 μM, while compounds 8 and 11 showed activities against S. aureus, E. coli, and B. subtilis, with MIC values in the range of 4.15 to 12.5 μg/mL.

scholarly journals Sesquiterpenoids From the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

2021 ◽  
Vol 12 ◽  
Author(s):  
Ting Shi ◽  
Xiang-Qian Li ◽  
Li Zheng ◽  
Ya-Hui Zhang ◽  
Jia-Jia Dai ◽  
...  
Keyword(s):  
Pathogenic Fungi ◽  
Antibacterial Activities ◽  
Aeromonas Salmonicida ◽  
Systematic Research ◽  
Cytotoxic Activities ◽  
Hepg2 Cell Lines ◽  
New Compounds ◽  
The Antarctic ◽  
First Time ◽  
Hepatoma Hepg2

The fungal strains Pseudogymnoascus are a kind of psychrophilic pathogenic fungi that are ubiquitously distributed in Antarctica, while the studies of their secondary metabolites are infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11 led to the isolation of six new tremulane sesquiterpenoids pseudotremulanes A–F (1–6), combined with one known analog 11,12-epoxy-12β-hydroxy-1-tremulen-5-one (7), and five known steroids (8–12). The absolute configurations of the new compounds (1–6) were elucidated by their ECD spectra and ECD calculations. Compounds 1–7 were proved to be isomeride structures with the same chemical formula. Compounds 1/2, 3/4, 1/4, and 2/3 were identified as four pairs of epimerides at the locations of C-3, C-3, C-9, and C-9, respectively. Compounds 8 and 9 exhibited cytotoxic activities against human breast cancer (MDA-MB-231), colorectal cancer (HCT116), and hepatoma (HepG2) cell lines. Compounds 9 and 10 also showed antibacterial activities against marine fouling bacteria Aeromonas salmonicida. This is the first time to find terpenoids and steroids in the fungal genus Pseudogymnoascus.

scholarly journals New Poly(Propylene Imine) Dendrimer Modified with Acridine and Its Cu(II) Complex: Synthesis, Characterization and Antimicrobial Activity

Materials ◽  
2019 ◽  
Vol 12 (18) ◽  
pp. 3020 ◽  
Author(s):  
Paula Bosch ◽  
Desislava Staneva ◽  
Evgenia Vasileva-Tonkova ◽  
Petar Grozdanov ◽  
Ivanka Nikolova ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Copper Ions ◽  
Spectral Characteristics ◽  
Dilution Method ◽  
Pathogenic Microorganisms ◽  
Paramagnetic Resonance ◽  
Poly Propylene ◽  
New Compounds ◽  
First Time

A second-generation poly(propylene imine) dendrimer modified with acridine and its Cu(II) complex have been synthesized for the first time. It has been found that two copper ions form complexes with the nitrogen atoms of the dendrimeric core by coordinate bonds. The new compounds have been characterized by nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), fourier-transform infrared spectroscopy (FTIR) and fluorescence spectroscopy. The spectral characteristics of the modified dendrimer have been measured in different organic solvents, and a negative fluorescence solvatochromism has been observed. The antimicrobial activity of the dendrimers has been tested against model pathogenic microorganisms in agar and by broth dilution method. The cotton fabric treated with both dendrimers has been evaluated towards pathogenic microorganisms. The obtained modified cotton fabrics have been shown to hamper bacterial growth and to prevent biofilm formation. Dendrimer cytotoxicity has been investigated in vitro in the model HEp-2 cell line.

scholarly journals Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Study ◽  
Positive Control ◽  
Hydroxyl Group ◽  
Etoac Extract ◽  
The Third ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

Synthesis and Evaluation of in vitro Antiplatelet Aggregation Activities of 2-Methoxy-5-Aminobenzamides

2019 ◽  
Vol 16 (9) ◽  
pp. 1040-1050
Author(s):  
Lili Liu ◽  
Xiujie Liu ◽  
Guangling Chen ◽  
Kai Qiu
Keyword(s):  
L929 Cells ◽  
Cytotoxicity Activity ◽  
Antiplatelet Aggregation ◽  
Ic50 Value ◽  
Lower Effect ◽  
New Compounds ◽  
Group Characteristics ◽  
Better Than ◽  
Methoxybenzoic Acid

Objective: According to the principles of drug design, the structures of picotamide and betrixaban were combined to design novel series of 2-methoxy-5-aminobenzamides. A total of twenty new compounds 1a-1t have been synthesized and evaluated for their antiplatelet aggregation activities in vitro. Methods: In the structural design of target compounds 1a-1t, the betrixaban was retained group characteristics and the picotamide was retained its 1, 3, 4-substitution position. With 2-methoxybenzoic acid as starting material, compounds 1a-1t were synthesized after 5 steps of nitration, acylation, ammoniation, reduction and secondary ammoniation. And their antiplatelet aggregation activities in vitro were assessed by the Born test with ADP, arachidonic acid and collagen as inducing agents, respectively, and with aspirin and picotamide as two reference drugs. Results: The compound 1f (46.14%±0.07) had the highest activity for ADP and its IC50 value was 0.17 µM, far better than the two control drugs aspirin (0.44 µM) and picotamide (0.47 µM). The IC50 value of four compounds 1i (0.24 µM), 1j (0.22 µM), 1r (0.25 µM) and 1t (0.24 µM), displayed higher antiplatelet activities in vitro for AA than aspirin (0.43 µM) and picotamide (0.34 µM). Evaluation of cytotoxicity activity of the compounds against L929 cells line revealed that at lower concentration of 10 µmol·L-1, compound 1p had lower effect on L929 cells, and its cell survival rate (88.24%±4.16) was higher than that (82.35%±4.16) of picotamide. Conclusion: Novel series of 2-methoxy-5-aminobenzamides has shown higher in vitro antiplatelet activities and lower effect on L929 cells at lower concentration.

scholarly journals Design, Synthesis and Biological Evaluation of Novel 4-Substituted Coumarin Derivatives as Antitumor Agents

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2281 ◽  
Author(s):  
Ran An ◽  
Zhuang Hou ◽  
Jian-Teng Li ◽  
Hao-Nan Yu ◽  
Yan-Hua Mou ◽  
...  
Keyword(s):  
Antitumor Agents ◽  
Cancer Cell Line ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Hypoxic Conditions ◽  
Ca Ix ◽  
Ic50 Value ◽  
Almost All ◽  
New Compounds

Herein, fifteen new compounds containing coumarin, 1,2,3-triazole and benzoyl- substituted arylamine moieties were designed, synthesized and tested in vitro for their anticancer activity. The results showed that all tested compounds had moderate antiproliferative activity against MDA-MB-231, a human breast cancer cell line, under both normoxic and hypoxic conditions. Furthermore, the 4-substituted coumarin linked with benzoyl 3,4-dimethoxyaniline through 1,2,3-triazole (compound 5e) displayed the most prominent antiproliferative activities with an IC50 value of 0.03 μM, about 5000 times stronger than 4-hydroxycoumarin (IC50 > 100 μM) and 20 times stronger than doxorubicin (IC50 = 0.60 μM). Meanwhile, almost all compounds revealed general enhancement of proliferation-inhibiting activity under hypoxia, contrasted with normoxia. A docking analysis showed that compound 5e had potential to inhibit carbonic anhydrase IX (CA IX).

scholarly journals New Compounds from Leaves of Smallanthus sonchifolius

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400
Author(s):  
Xiang Zheng ◽  
Gai Kuo ◽  
Dou De-Qiang ◽  
Kang Ting-Guo ◽  
Shi Yu-Yuan ◽  
...  
Keyword(s):  
Benzyl Alcohol ◽  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Trienoic Acid ◽  
Octadecatrienoic Acid ◽  
Smallanthus Sonchifolius ◽  
New Compounds ◽  
First Time ◽  
Chemical Evidence

A new octadecatrienoic acid and a new benzyl glycoside, along with a known compound, were isolated from the leaves of Smallanthus sonchifolius. The structures of the two new compounds were elucidated as 13(R)-hydroxy-octadeca-(9E,11E,15Z)-trienoic acid (1) and benzyl alcohol 7-O-α-L-arabinopyranosyl(1″→2′)-β-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trienoic acid (3) by comparison of its spectral data with that reported. Compound 3 was isolated for the first time from the title plant.

scholarly journals Antileishmanial Phenylpropanoids from the Leaves ofHyptis pectinata(L.) Poit

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Rosangela A. Falcao ◽  
Patricia L. A. do Nascimento ◽  
Silvana A. de Souza ◽  
Telma M. G. da Silva ◽  
Aline C. de Queiroz ◽  
...  
Keyword(s):  
Rosmarinic Acid ◽  
Bacterial Infections ◽  
Ethanol Extract ◽  
Spectroscopic Methods ◽  
Etoh Extract ◽  
Promastigote Form ◽  
Water Fractions ◽  
New Compounds ◽  
First Time

Hyptis pectinata, popularly known in Brazil as “sambacaitá” or “canudinho,” is an aromatic shrub largely grown in the northeast of Brazil. The leaves and bark are used in an infusion for the treatment of throat and skin inflammations, bacterial infections, pain, and cancer. Analogues of rosmarinic acid and flavonoids were obtained from the leaves ofHyptis pectinataand consisted of two new compounds, sambacaitaric acid (1) and 3-O-methyl-sambacaitaric acid (2), and nine known compounds, rosmarinic acid (3), 3-O-methyl-rosmarinic acid (4), ethyl caffeate (5), nepetoidin A (6), nepetoidin B (7), cirsiliol (8), circimaritin (9), 7-O-methylluteolin (10), and genkwanin (11). The structures of these compounds were determined by spectroscopic methods. Compounds1–5, and7were evaluatedin vitroagainst the promastigote form ofL. braziliensis, and the ethanol extract. The hexane, ethyl acetate, and methanol-water fractions were also evaluated. The EtOH extract, the hexane extract, EtOAc, MeOH:H2O fractions; and compounds1,2and4exhibited antileishmanial activity, and compound1was as potent as pentamidine. In contrast, compounds3,5, and7did not present activity against the promastigote form ofL. braziliensisbelow 100 µM. To our knowledge, compounds1and2are being described for the first time.

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