scholarly journals Lanostane Triterpenes from Gloeophyllum odoratum and Their Anti-Influenza Effects

Planta Medica ◽  
2018 ◽  
Vol 85 (03) ◽  
pp. 195-202 ◽  
Author(s):  
Ulrike Grienke ◽  
Julia Zwirchmayr ◽  
Ursula Peintner ◽  
Ernst Urban ◽  
Martin Zehl ◽  
...  
Keyword(s):  
Fruit Body ◽  
Ionization Mass ◽  
Body Extract ◽  
H1n1 Strain ◽  
Ic50 Values ◽  
H3n2 Influenza ◽  
Work Up ◽  
First Time ◽  
H3n2 Influenza Virus

AbstractIn an in vitro screening for anti-influenza agents from European polypores, the fruit body extract of Gloeophyllum odoratum dose-dependently inhibited the cytopathic effect of the H3N2 influenza virus A/Hong Kong/68 (HK/68) in Madin Darby canine kidney cells with a 50% inhibitory concentration (IC50) of 15 µg/mL, a noncytotoxic concentration. After a chromatographic work-up, eight lanostane triterpenes (1–8) were isolated and their structures were elucidated based on high-resolution electrospray ionization mass spectrometry analyses, and one- and two-dimensional nuclear magnetic resonance experiments. Constituents 1 (gloeophyllin K) and 2 (gloeophyllin L) are reported here for the first time, and compounds 5, 7, and 8 have not been described for the investigated fungal material so far. The highest activity was determined for trametenolic acid B (3) against HK/68 and the 2009 pandemic H1N1 strain A/Jena/8178/09 with IC50 values of 14 and 11 µM, respectively. In a plaque reduction assay, this compound was able to bind to cell-free viruses and to neutralize their infectivity.

scholarly journals High-resolution AP-SMALDI MSI as a tool for drug imaging in Schistosoma mansoni

2021 ◽  
Author(s):  
Annika S. Mokosch ◽  
Stefanie Gerbig ◽  
Christoph G. Grevelding ◽  
Simone Haeberlein ◽  
Bernhard Spengler
Keyword(s):  
Schistosoma Mansoni ◽  
Egg Production ◽  
Drug Repurposing ◽  
Cancer Drug ◽  
Ionization Mass ◽  
Parasitic Flatworm ◽  
Paired Female ◽  
First Time ◽  
Organ Tropism

AbstractSchistosoma mansoni is a parasitic flatworm causing schistosomiasis, an infectious disease affecting several hundred million people worldwide. Schistosomes live dioeciously, and upon pairing with the male, the female starts massive egg production, which causes pathology. Praziquantel (PZQ) is the only drug used, but it has an inherent risk of resistance development. Therefore, alternatives are needed. In the context of drug repurposing, the cancer drug imatinib was tested, showing high efficacy against S. mansoni in vitro. Besides the gonads, imatinib mainly affected the integrity of the intestine in males and females. In this study, we investigated the potential uptake and distribution of imatinib in adult schistosomes including its distribution kinetics. To this end, we applied for the first time atmospheric-pressure scanning microprobe matrix-assisted laser desorption/ionization mass spectrometry imaging (AP-SMALDI MSI) for drug imaging in paired S. mansoni. Our results indicate that imatinib was present in the esophagus and intestine of the male as early as 20 min after in vitro exposure, suggesting an oral uptake route. After one hour, the drug was also found inside the paired female. The detection of the main metabolite, N-desmethyl imatinib, indicated metabolization of the drug. Additionally, a marker signal for the female ovary was successfully applied to facilitate further conclusions regarding organ tropism of imatinib. Our results demonstrate that AP-SMALDI MSI is a useful method to study the uptake, tissue distribution, and metabolization of imatinib in S. mansoni. The results suggest using AP-SMALDI MSI also for investigating other antiparasitic compounds and their metabolites in schistosomes and other parasites. Graphical abstract

scholarly journals Mammalian Arginase Inhibitory Activity of Methanolic Extracts and Isolated Compounds from Cyperus Species

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1694
Author(s):  
Kamel Arraki ◽  
Perle Totoson ◽  
Alain Decendit ◽  
Andy Zedet ◽  
Justine Maroilley ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Methanolic Extract ◽  
Significant Inhibition ◽  
Isolation And Identification ◽  
Vasorelaxant Effect ◽  
Methanolic Extracts ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
First Time

Polyphenolic enriched extracts from two species of Cyperus, Cyperus glomeratus and Cyperus thunbergii, possess mammalian arginase inhibitory capacities, with the percentage inhibition ranging from 80% to 95% at 100 µg/mL and 40% to 64% at 10 µg/mL. Phytochemical investigation of these species led to the isolation and identification of two new natural stilbene oligomers named thunbergin A-B (1–2), together with three other stilbenes, trans-resveratrol (3), trans-scirpusin A (4), trans-cyperusphenol A (6), and two flavonoids, aureusidin (5) and luteolin (7), which were isolated for the first time from C.thunbergii and C. glomeratus. Structures were established on the basis of the spectroscopic data from MS and NMR experiments. The arginase inhibitory activity of compounds 1–7 was evaluated through an in vitro arginase inhibitory assay using purified liver bovine arginase. As a result, five compounds (1, 4–7) showed significant inhibition of arginase, with IC50 values between 17.6 and 60.6 µM, in the range of those of the natural arginase inhibitor piceatannol (12.6 µM). In addition, methanolic extract from Cyperus thunbergii exhibited an endothelium and NO-dependent vasorelaxant effect on thoracic aortic rings from rats and improved endothelial dysfunction in an adjuvant-induced arthritis rat model.

scholarly journals In vitro Antidiabetic, anti-obesity and antioxidant proprities of Rosemary extracts

2014 ◽  
Vol 10 (2) ◽  
pp. 2305-2316 ◽  
Author(s):  
Manel Ben Ali ◽  
Kais Mnafgui ◽  
Abdelfattah Feki ◽  
Mohamed Damak ◽  
Noureddine Allouche
Keyword(s):  
Essential Oil ◽  
Ethyl Acetate ◽  
Pancreatic Lipase ◽  
Antioxidant Properties ◽  
Methanolic Extracts ◽  
Ic50 Values ◽  
Inhibitory Potential ◽  
Prevention Of Diabetes ◽  
First Time

Diabetes mellitus is a serious health problem worldwide that has adverse and long-lasting consequences for individuals, families, and communities. Hence, this study sought to investigate the inhibitory potential of rosemary extracts on key-enzymes related to diabetes such as α-amylase and pancreatic lipase activities, as well as to assess their antioxidant properties in vitro. The IC50 values of Rosemary essential oil, ethyl acetate and methanolic extracts against α-amylase were 28.36, 34.11 and 30.39 µg/mL respectively, and those against pancreatic lipase were 32.25, 36.64 and 34.07 µg/mL, suggesting strong anti-diabetic and anti-obesity effects of Rosemary. The methanolic extract was found to be the highest in levels of phenolic (282.98 µgGAE/mg extract) and flavonoids (161.05 µg QE /mg extract) contents as well as in the antioxidant activity (IC50 = 15.82 µg/mL) as compared to other extracts ethyl acetate (IC50 = 32.23 µg/mL) and essential oil  (IC50 = 96.12 µg/mL).Antioxidant efficacy of Rosemary extracts has been estimated in the stabilization of sunflower oil (SFO) at three different concentrations, i.e. 200 (SFO-200), 500 (SFO-500) and 1000 ppm (SFO-1000). Results showed the highest efficiency of SFO-1000.The results obtained in this study demonstrated for the first time that Rosemary is a potent source of natural inhibitors of α-amylase and pancreatic lipase with powerful antioxidants proprieties that might be used in the food stabilization and the prevention of diabetes and obesity complications as a complementary pharmacological drug.

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 Antiprotozoal Activity Against Entamoeba histolytica of Flavonoids Isolated from Lippia graveolens Kunth

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2464
Author(s):  
Ramiro Quintanilla-Licea ◽  
Javier Vargas-Villarreal ◽  
María Julia Verde-Star ◽  
Verónica Mayela Rivas-Galindo ◽  
Ángel David Torres-Hernández
Keyword(s):  
Entamoeba Histolytica ◽  
Inhibitory Concentration ◽  
Public Health Problem ◽  
In Vitro Tests ◽  
Antiprotozoal Activity ◽  
Subsequent Work ◽  
Antiamoebic Activity ◽  
Work Up ◽  
First Time

Amebiasis caused by Entamoeba histolytica is nowadays a serious public health problem worldwide, especially in developing countries. Annually, up to 100,000 deaths occur across the world. Due to the resistance that pathogenic protozoa exhibit against commercial antiprotozoal drugs, a growing emphasis has been placed on plants used in traditional medicine to discover new antiparasitics. Previously, we reported the in vitro antiamoebic activity of a methanolic extract of Lippia graveolens Kunth (Mexican oregano). In this study, we outline the isolation and structure elucidation of antiamoebic compounds occurring in this plant. The subsequent work-up of this methanol extract by bioguided isolation using several chromatographic techniques yielded the flavonoids pinocembrin (1), sakuranetin (2), cirsimaritin (3), and naringenin (4). Structural elucidation of the isolated compounds was achieved by spectroscopic/spectrometric analyses and comparing literature data. These compounds revealed significant antiprotozoal activity against E. histolytica trophozoites using in vitro tests, showing a 50% inhibitory concentration (IC50) ranging from 28 to 154 µg/mL. Amebicide activity of sakuranetin and cirsimaritin is reported for the first time in this study. These research data may help to corroborate the use of this plant in traditional Mexican medicine for the treatment of dyspepsia.

scholarly journals Momilactones A, B, and Tricin in Rice Grain and By-Products are Potential Skin Aging Inhibitors

Foods ◽  
2019 ◽  
Vol 8 (12) ◽  
pp. 602 ◽  
Author(s):  
Nguyen Van Quan ◽  
Dam Duy Thien ◽  
Tran Dang Khanh ◽  
Hoang-Dung Tran ◽  
Tran Dang Xuan
Keyword(s):  
Liquid Chromatography ◽  
High Performance ◽  
Biological Activities ◽  
Ultra Performance Liquid Chromatography ◽  
Skin Aging ◽  
Ionization Mass ◽  
Rice Grain ◽  
Synergistic Activity ◽  
Ic50 Values

We previously reported the inhibitory potentials of momilactones A (MA) and B (MB) against key enzymes related to type 2 diabetes and obesity. In this study, antioxidant and anti-skin-aging activities of MA and MB were investigated and compared with tricin, a well-known antioxidant and antiaging flavonoid in rice. MA, MB, and tricin were purified from rice husk by column chromatography and their biological activities were subsequently assayed by in vitro trials. The contents of MA, MB, and tricin of different commercial rice cultivars in Japan were quantified and confirmed by ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS) and high-performance liquid chromatography (HPLC) analyses. The antioxidant assays revealed a synergistic activity of the mixture MA and MB (MAB, 1:1, v/v). In addition, in 2,2’-azino-bis (ABTS) assay, IC50 values of MAB (0.3 mg/mL) and tricin (0.3 mg/mL) was 4-fold and 9-fold greater than that of individual MB (1.3 mg/mL) or MA (2.8 mg/mL), respectively. The in vitro enzymatic assays on pancreatic elastase and tyrosinase indicated that MA and MB were potential to relief skin wrinkles and freckles. In detail, MA exerted higher inhibition on both enzymatic activities (30.9 and 37.6% for elastase and tyrosinase inhibition, respectively) than MB (18.5 and 12.6%) and MAB (32.0 and 19.7%) at a concentration of 2.0 mg/mL. Notably, MA and the mixture MAB exhibited stronger inhibitions on elastase and tyrosinase in comparison with tricin and vanillin. MA, MB, and tricin in rice are potential to develop cosmetics as well as supplements for skin aging treatments.

scholarly journals Cytotoxic Pentacyclic Triterpenoids from Combretum oliviforme

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500
Author(s):  
Xiao-Peng Wu ◽  
Chang-Ri Han ◽  
Guang-Ying Chen ◽  
Yuan Yuan ◽  
Jian-Ying Xie
Keyword(s):  
Cytotoxic Activity ◽  
Cancer Cell Line ◽  
Lung Cancer Cell Line ◽  
Human Lung Cancer ◽  
Ionization Mass ◽  
Human Gastric Cancer ◽  
Pentacyclic Triterpenoids ◽  
Acetyl Group ◽  
First Time

Four pentacyclic triterpenoids were obtained from the leaves of Combretum oliviforme Chao, 3β–hydroxyolean–12–en–28–oic acid (1), 23– O–[α-L-(4′-acetylrhamnopyranosyl)]–imberbic acid (2), 23–acetoxy–3β–acetylimberbic acid–29–methyl ester (3), and 23– O–[α-L-rhamnopyranosyl]-1,3β-diacetylimberbic acid (4). Hydrolysis of 2 and 4 gave 23–hydroxyimberbic acid (5). The structures were elucidated by NMR, electrospray ionization mass spectrometry (ESIMS) and comparison with literature data. Compounds 1, 2, 3 and 4 were isolated from C. oliviforme Chao leaves for the first time and 3 for the first time from any natural source. All compounds were tested in vitro for their activity against human lung cancer cell line SPC-A-1, human erythroleukaemic line K562 and human gastric cancer SGC-7901 cells. Compounds 1, 3, 4 and 5 had cytotoxic activity for the three cell lines with IC50 0.69-69.68 μM. These results suggest that the presence of acetyl group in the triterpene aglycone structure plays an essential role for cytotoxic activity.

In Vitro Human Dihydroorotate Dehydrogenase Inhibitory, Anti-inflammatory and Cytotoxic Activities of Alkaloids from the Seeds of Nigella glandulifera

Planta Medica ◽  
2018 ◽  
Vol 84 (14) ◽  
pp. 1013-1021 ◽  
Author(s):  
Jun-Bo Gao ◽  
Xing-Jie Zhang ◽  
Rui-Han Zhang ◽  
Li-Li Zhu ◽  
De-Bing Pu ◽  
...  
Keyword(s):  
Folk Medicine ◽  
Positive Control ◽  
Cytotoxic Activities ◽  
Dihydroorotate Dehydrogenase ◽  
X Ray Diffraction ◽  
Ic50 Values ◽  
Pharmacologically Active ◽  
Pharmacologically Active Compounds ◽  
First Time

AbstractFour new dolabellane-type diterpene alkaloids, glandulamines A – D (1 – 4), together with twelve known compounds (5 – 16), were isolated from the seeds of Nigella glandulifera using repeated column chromatography and semipreparative HPLC. The structures of 1 – 16 were elucidated based on NMR data analysis, HRMS experiments and other spectroscopic interpretations. The absolute configuration of 5 was determined by single-crystal X-ray diffraction data for the first time. Compounds 10 and 12 showed human dihydroorotate dehydrogenase inhibitory activity with IC50 values of 61.1 ± 5.3 and 45.9 ± 3.0 µM, respectively. Molecular docking of the active compound 12 and positive control teriflunomide on the inhibitor-binding site of human dihydroorotate dehydrogenase was subsequently performed to visualize the interaction pattern. In addition, compounds 8 and 10 exhibited inhibitory effects against lipopolysaccharide-induced nitric oxide production with inhibition rates of 61 and 41%, respectively, at the concentration of 10 µM. Compounds 9 and 12 showed cytotoxic activities with cell viability varying from 29 ~ 57% at 100 µM against T98G, U87, U251, and GL261 glioma cancer cell lines. These data provide new insights on the pharmacologically active compounds of this plant widely used in folk medicine.

scholarly journals Antioxidant and Hepatoprotective Activity of Phenyl Glycosides Isolated From Heliciopsis lobata

2020 ◽  
Vol 15 (8) ◽  
pp. 1934578X2094625
Author(s):  
Bui Van Trung ◽  
Do Thi Thao ◽  
Duong Hong Anh ◽  
Phan Van Kiem ◽  
Pham Hung Viet
Keyword(s):  
Barbituric Acid ◽  
Multiple Bond ◽  
Radical Scavenging ◽  
Hepatoprotective Activity ◽  
Ionization Mass ◽  
Chemical Structures ◽  
Heteronuclear Single Quantum Correlation ◽  
First Time ◽  
C Nmr

A new macrocyclic glycoside named helilobatoside A (1) and 5 known phenyl glycosides as 3,5-dimethoxy-4-hydroxyphenyl-1- O-β-d-glucopyranoside (2), tachioside (3), isotachioside (4), 1-(4-hydroxy-3-methoxyphenyl)-1-propanone-3- O-β-d-glucopyranoside (5), and 1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone-3- O-β-d-glucopyranoside (6), were isolated from the wood of Heliciopsis lobata (Merr.) Sleumer. Their chemical structures were elucidated using a combination of high-resolution electrospray ionization mass spectrometry, 1-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectral data as well as by comparison with data in the previous literature. This is the first time the 13C NMR data of compounds 5 and 6 were reported and also were assigned by heteronuclear single quantum correlation and heteronuclear multiple bond correlation spectra. Compounds 2-6 were first isolated from Heliciopsis genus. The isolated compounds were evaluated for their antioxidant and hepatoprotective activities in vitro. Compound 2 showed potential as an antioxidant in a 2,2-diphenyl-1-picryl-hydrazyl-hydrate assay (half-maximal inhibitory concentration [IC50] = 6.07 ± 0.17 µg/mL) and in thio-barbituric acid reactive substances assay (IC50 = 89.55 ± 8.26 µg/mL). This compound could also reduce the toxic effects of carbon tetrachloride on HepG2 survival and significantly protect the viability of cells up to 52.25 ± 4.36% at the 100 µg/mL treatment ( P < 0.05). Thus, with obtained results, the hepatoprotective activity of compound 2 could be related to radical scavenging and limited the lipid peroxidative activities.

scholarly journals Chemical Constituents From the Aerial Part of Tiliacora triandra (Colebr.) Diels and Their α-Glucosidase and α-Amylase Inhibitory Activity

2020 ◽  
Vol 15 (1) ◽  
pp. 1934578X1989959
Author(s):  
Emmanuel Ayobami Makinde ◽  
Chitchamai Ovatlarnporn ◽  
Chonlatid Sontimuang ◽  
Gaëtan Herbette ◽  
Opeyemi Joshua Olatunji
Keyword(s):  
Inhibitory Activity ◽  
Chemical Constituents ◽  
Ethyl Linoleate ◽  
Resonance Spectroscopy ◽  
Ionization Mass ◽  
Pheophorbide A ◽  
Aerial Parts ◽  
Fatty Acid Derivatives ◽  
First Time

Two new fatty acid derivatives identified as 5,7-dihydroxy-6-oxoheptadecanoic acid (1) and ethyl-5,7-dihydroxy-6-oxooctadecanoate (2) together with four known compounds, ethyl linolenate (3), ethyl linoleate (4), ethyl pheophorbide A (5), and pheophorbide A (6), were isolated from the aerial parts of Tiliacora triandra. All the compounds were isolated from T. triandra for the first time. The structures of the compounds were elucidated using high-resolution electrospray ionization mass spectrometry, 1-dimensional and 2-dimensional nuclear magnetic resonance spectroscopy, and comparison with literature data. All the isolated compounds were evaluated for their in vitro inhibitory activity against α-glucosidase and α-amylase. Compounds 1-6 exhibited α-glucosidase inhibitory activity with half-maximal inhibitory concentration values (IC50) values in the range of 11.58-424.06 μM, while only compound 1 displayed inhibitory activity against α-amylase at an IC50 value of 26.27 μM.

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