Asperflamides A and B from Aspergillus flavipes DZ-3, an Endophytic Fungus of Eucommia ulmoides Oliver

The fungus strain DZ-3 was isolated from twigs of the well-known medicinal plant Eucommia ulmoides Oliver and identified as Aspergillus flavipes. Two new alkaloids, named asperflaloids A and B (1 and 2), together with 10 known compounds (3–12) were obtained from the EtOAc extract of the strain. Interestingly, the alkaloids 1–4 with different frameworks are characterized by the presence of the same anthranilic acid residue. The structures were established by detailed analyses of the spectroscopic data. The absolute configuration of asperflaloids A and B was resolved by quantum chemistry calculation. All compounds were screened for their inhibitions against α-glucosidase and the antioxidant capacities. The results were that compound 3 had an IC50 value of 750.8 μM toward α-glucosidase, and the phenol compounds 7 and 8 exhibited potent antioxidant capacities with IC50 values 14.4 and 27.1 μM respectively.

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Inhibition of Protein Tyrosine Phosphatase 1B by Lutein Derivatives isolated from Mexican Oregano (Lippia graveolens)

Phytothérapie ◽

10.3166/phyto-2018-0074 ◽

2018 ◽

Vol 17 (3) ◽

pp. 134-139

Author(s):

R.M. Perez-Gutierrez

Keyword(s):

Protein Tyrosine Phosphatase ◽

Inhibitory Activity ◽

Spectroscopic Data ◽

Methanol Extract ◽

Tyrosine Phosphatase ◽

Positive Control ◽

Protein Tyrosine Phosphatase 1B ◽

Protein Tyrosine ◽

Ic50 Value ◽

Ic50 Values

Methanol extract from Lippia graveolens (Mexican oregano) was studied in order to identify inhibitory bioactives for protein tyrosine phosphatase 1B (PTP1B). Known flavone as lutein (1), and another flavone glycoside such as lutein-7-o-glucoside (2), 6-hydroxy-lutein-7-ohexoside (3) and lutein-7-o-ramnoide (4) were isolated from methanol extract of aerial parts of the Lippia graveolens. All isolates were identified based on extensive spectroscopic data analysis, including UV, IR, NMR, MS and compared with spectroscopic data previously reported. These flavones were evaluated for PTP1B inhibitory activity. Among them, compounds 1 and 3 displayed potential inhibitory activity against PTP1B with IC50 values of 7.01 ± 1.25 μg/ml and 18.4 μg/ml, respectively. In addition, compound 2 and 4 showed moderate inhibitory activity with an IC50 value of 23.8 ± 6.21 and 67.8 ± 5.80 μg/ml respectively. Among the four compounds, luteolin was found to be the most potent PTP1B inhibitor compared to the positive control ursolic acid, with an IC50 value of 8.12 ± 1.06 μg/ml. These results indicate that flavonoids constituents contained in Lippia graveolens can be considered as a natural source for the treatment of type 2 diabetes.

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

Marine Drugs ◽

10.3390/md18030164 ◽

2020 ◽

Vol 18 (3) ◽

pp. 164 ◽

Cited By ~ 1

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).

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Secondary Metabolites with Anti-Inflammatory Activities from One Actinobacteria Amycolatopsis taiwanensis

Molecules ◽

10.3390/molecules26195765 ◽

2021 ◽

Vol 26 (19) ◽

pp. 5765

Author(s):

Yung-Shun Su ◽

Ming-Der Wu ◽

Jih-Jung Chen ◽

Ming-Jen Cheng ◽

Yueh-Hsiung Kuo ◽

...

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

The North ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Production Activity ◽

Inos Inhibitor ◽

Ic50 Values ◽

New Compounds

Phytochemical investigation and chromatographic separation of extracts from one new actinobacteria strain Amycolatopsis taiwanensis that was isolated from soil of Yilan township, in the north of Taiwan, led to the isolation of nine new compounds, amycolataiwanensins A–I (1–9, resp.), and one new natural product, namely amycolataiwanensin J (10). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic-data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Of the isolates, 3, 5, 7 and 8 exhibited potent anti-NO production activity, with IC50 values of 17.52, 12.31, 17.81 and 13.32 μM, respectively, compared to that of quercetin, an iNOS inhibitor with an IC50 value of 35.94 μM. This is the first report on indole metabolite from the genus Amycolatopsis.

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Isolation of Bioactive Compounds from Aspergillus terreus LS07

Indonesian Journal of Chemistry ◽

10.22146/ijc.21243 ◽

2014 ◽

Vol 14 (3) ◽

pp. 304-310 ◽

Cited By ~ 4

Author(s):

Rizna Triana Dewi ◽

Sanro Tachibana ◽

Puspa Dewi ◽

L.B.S. Kardono ◽

Muhammad Ilyas

Keyword(s):

Free Radicals ◽

Oleic Acid ◽

Aspergillus Terreus ◽

Spectroscopic Analysis ◽

The Other ◽

Significant Activity ◽

Active Components ◽

Etoac Extract ◽

Ic50 Value ◽

Ic50 Values

This study aims to search for the active components from Aspergillus terreus LS07 which isolated from an Indonesian soil. Bioassay-guided fractionations of the ethyl acetate (EtOAc) extract against α-glucosidase and DPPH free radical to give four isolated compounds: oleic acid (1), ergosterol (2), butyrolactone I (3), and butyrolactone II (4). The structures of these metabolites were assigned on the basis of detailed spectroscopic analysis. Oleic acid (1) was showed significant activity toward α-glucosidase with IC50 value of 8.54 μM, but not for antioxidant. Butyrolactone I (3) and II (4) were showed significant activities against the α-glucosidase with their IC50 values at 52.17 and 96.01 μM, and those against DPPH free radicals at 51.39 and 17.64 μM, respectively. On the other hand, ergosterol (2) did not show any activities.

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Optimization protocol and bioactivity assessment for the microwave-assisted extraction of flavonoids from Eucommia ulmoides Oliver seed meal using response surface methodology

BioResources ◽

10.15376/biores.16.4.7367-7378 ◽

2021 ◽

Vol 16 (4) ◽

pp. 7367-7378

Author(s):

Hui Ouyang ◽

Songlin Li ◽

Wanxi Peng ◽

Zhuping Xiao ◽

Yongkang Zhang

Keyword(s):

Response Surface Methodology ◽

Response Surface ◽

Seed Meal ◽

Eucommia Ulmoides ◽

Total Flavonoids ◽

Microwave Assisted Extraction ◽

Microwave Assisted ◽

Assisted Extraction ◽

Ic50 Value ◽

Eucommia Ulmoides Oliver

Response surface methodology was utilized to optimize the microwave-assisted extraction of flavonoids from Eucommia ulmoides Oliver seed meal. In addition, the optimal processing conditions for the extraction of E. ulmoides seed meal flavonoids were as follows: a processing time of 30 min, a liquid to solid ratio of 54 to 1 (mL/g), an ethanol concentration of 77%, and a temperature of 69 °C. The total flavonoids extraction percentage was 0.6611%. Moreover, the total flavonoids extracted from E. ulmoides seed meal were good for scavenging diphenyl picryl hydrazinyl. The E. ulmoides seed meal total flavonoids exhibited an obvious dose-dependent inhibitory effect on α-glucosidase in the concentration range of 0.05 to 1.0 mg·mL−1. The IC50 value of the E. ulmoides seed meal flavonoids was slightly lower than the IC50 value of acarbose. According to the results of the xanthine oxidase inhibitory activity test, the IC50 value of the E. ulmoides seed meal flavonoids was higher than the IC50 value of allopurinol.

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Inhibition by Glaucocalyxin A of Aggregation of Rabbit Platelets Induced by ADP, Arachidonic Acid and Platelet-Activating Factor, and Inhibition of [3H]-PAF Binding

Thrombosis and Haemostasis ◽

10.1055/s-0038-1648470 ◽

1992 ◽

Vol 67 (04) ◽

pp. 458-460 ◽

Cited By ~ 12

Author(s):

Zhang Bin ◽

Long Kun

Keyword(s):

Arachidonic Acid ◽

Platelet Aggregation ◽

Platelet Activating Factor ◽

Northeastern China ◽

Ethereal Extract ◽

Ic50 Value ◽

Rabbit Platelets ◽

Ic50 Values ◽

Induced Aggregation

SummaryGlaucocalyxin A is a new diterpenoid isolated from the ethereal extract of the leaves of Rabdosia japonica (Burm f) Hara var glaucocalyx (Maxim) Hara (Labiatae) collected in the northeastern China. When it was incubated with washed rabbit platelets, glaucocalyxin A inhibited ADP- or arachidonic acid-induced platelet aggregation with IC50 values of 4.4 μmol/1, 14.1 μmol/1 respectively. Glaucocalyxin A also inhibited PAF-induced aggregation of rabbit platelets which were refractory to ADP and arachidonic acid with an IC50 value of 13.7 μmol/1. Analysis of [3H]-PAF binding showed that glaucocalyxin A prevented [3H]-PAF binding to intact washed rabbit platelets with an IC50 value of 8.16 μmol/1, which was consistent with its inhibition of PAF-induced platelet aggregation.

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Synthesis and Assessment of Novel Anti-chlamydial Benzylidene Acylhydrazides Derivatives

Letters in Drug Design & Discovery ◽

10.2174/1570180814666170526170227 ◽

2018 ◽

Vol 15 (1) ◽

pp. 31-36 ◽

Cited By ~ 5

Author(s):

Xiaofeng Bao ◽

Ying Xue ◽

Chao Xia ◽

Yin Lu ◽

Ningjing Yang ◽

...

Keyword(s):

Inhibitory Effect ◽

Dependent Manner ◽

Iron Starvation ◽

Hydrochloride Salt ◽

Obligate Intracellular ◽

Biphasic Life Cycle ◽

Ic50 Value ◽

Ic50 Values ◽

Dose Dependent ◽

Better Than

Background: Chlamydiae, characterized by a unique biphasic life cycle, are a group of Gram-negative obligate intracellular bacterial pathogens responsible for diseases in a range of hosts including humans. Benzylidene acylhydrazide CF0001 could inhibit chlamydiae independent of iron starvation and T3SS inhibition. This finding promoted us to design and synthesize more benzylidene acylhydrazides to find novel anti-chlamydial agents. Methods: The carboxylic acids 1a-1d were coupled with Boc-hydrazide inpresence of EDCI and DMAP to obtain the intermediate 2a-2d in 60-62% yields. N-Boc deprotections were performed to obtain hydrazide hydrochloride salt 3a-3d. Nextly, the hydrazides were subjected to condensation with aldehydes to obtain benzylidene acylhydrazides 4a-4g in 30-52% yields in two steps. Results: Compound 4d exhibited best inhibitory effect on the formation and growth of chlamydial inclusions. The IC50 value of compound 4d for infectious progenies was 3.55 µM, better than 7.30 µM of CF0001. Conclusion: To find novel anti-chlamydial agents, we have designed and synthesized benzylidene acylhydrazides 4a-4g. Compounds 4a, 4d, 4g showed inhibitory activity on C. muridarum with the IC50 values from 3.55-12 µM. The 3,5-dibromo-4-hydroxyl substitutes on ring B are critical to keep their anti-chlamydial activity. Compound 4d inhibited C. muridarum in a dose-dependent manner without apparent cytotoxicity.

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Synthesis and Structure−Activity Relationship Studies of N-monosubstituted Aroylthioureas as Urease Inhibitors

Medicinal Chemistry ◽

10.2174/1573406416999200818152440 ◽

2020 ◽

Vol 16 ◽

Author(s):

Wei-Wei Ni ◽

Hai-Lian Fang ◽

Ya-Xi Ye ◽

Wei-Yi Li ◽

Li Liu ◽

...

Keyword(s):

Regression Analysis ◽

Mammalian Cells ◽

Intact Cell ◽

Linear Regression Analysis ◽

Positive Control ◽

Acetohydroxamic Acid ◽

Urease Inhibitors ◽

Ic50 Value ◽

Ic50 Values ◽

Low Cytotoxicity

Background: Thiourea is a classical urease inhibitor usually as a positive control, and many N,N`-disubstituted thioureas have been determined as urease inhibitors. However, due to steric hindrance, N,N`-disubstituted thiourea motif could not bind urease as thiourea. On the contrary, N-monosubstituted thioureas with a tiny thiourea motif could theoretically bind into the active pocket as thiourea. Objective: A series of N-monosubstituted aroylthioureas were designed and synthesized for evaluation as urease inhibitors. Methods: Urease inhibition was determined by the indophenol method and IC50 values were calculated using computerized linear regression analysis of quantal log dose-probit functions. The kinetic parameters were estimated viasurface plasmon resonance (SPR) and by nonlinear regression analysis based on the mixed type inhibition model derived from Michaelis-Menten kinetics. Results: Compounds b2, b11and b19 reversibly inhibited urease with a mixed mechanism, and showed excellent potency against both cell-free urease and urease in intact cell, with IC50 values being 90-to 450-fold and 5-to 50-fold lower than the positive control acetohydroxamic acid, respectively. The most potent compound b11 showed IC50 value of 0.060 ±0.004μM against cell-free urease, which bound to urea binding site with a very low KDvalue (0.420±0.003nM) and a very long residence time (6.7 min). Compound b11was also demonstrated having very low cytotoxicity to mammalian cells. Conclusion: These results revealed that N-monosubstituted aroylthioureas clearly bind the active site of urease as expected, and represent a new class of urease inhibitors for the development of potential therapeutics against infections caused by ure-ase-containing pathogens.

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