scholarly journals Identification of a Collagenase-Inhibiting Flavonoid from Alchemilla vulgaris Using NMR-Based Metabolomics

Planta Medica ◽  
2018 ◽  
Vol 84 (12/13) ◽  
pp. 941-946 ◽  
Author(s):  
Manuela Mandrone ◽  
Aline Coqueiro ◽  
Ferruccio Poli ◽  
Fabiana Antognoni ◽  
Young Choi
Keyword(s):  
1H Nmr ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Bone Diseases ◽  
Activity Data ◽  
Federal Drug Administration ◽  
Natural Product Research ◽  
Partial Least Squares Model ◽  
Ethnobotanical Uses

AbstractThis paper describes the use of 1H NMR profiling and chemometrics in order to facilitate the selection of medicinal plants as potential sources of collagenase inhibitors. A total of 49 plants with reported ethnobotanical uses, such as the healing of wounds and burns, treatment of skin-related diseases, rheumatism, arthritis, and bone diseases, were initially chosen as potential candidates. The in vitro collagenase inhibitory activity of hydroalcoholic extracts of these plants was tested. Moreover, their phytochemical profiles were analyzed by 1H NMR and combined with the inhibitory activity data by an orthogonal partial least squares model. The results showed a correlation between the bioactivity and the concentration of phenolics, including flavonoids, phenylpropanoids, and tannins, in the extracts. Considering the eventual false-positive effect on the bioactivity given by tannins, a tannin removal procedure was performed on the most active extracts. After this procedure, Alchemilla vulgaris was the most persistently active, proving to owe its activity to compounds other than tannins. Thus, this plant was selected as the most promising and further investigated through bioassay-guided fractionation, which resulted in the isolation of a flavonoid, quercetin-3-O-β-glucuronide, as confirmed by NMR and HRMS spectra. This compound showed not only a higher activity than other flavonoids with the same aglycone moiety, but was also higher than doxycycline (positive control), the only Federal Drug Administration-approved collagenase inhibitor. The approach employed in this study, namely the integration of metabolomics and bioactivity-guided fractionation, showed great potential as a tool for plant selection and identification of bioactive compounds in natural product research.

scholarly journals Xanthine oxidase inhibitory activity of a new isocoumarin obtained from Marantodes pumilum var. pumila leaves

2020 ◽  
Vol 20 (1) ◽  
Author(s):  
Nor-Ashila Aladdin ◽  
Khairana Husain ◽  
Juriyati Jalil ◽  
Carla Wulandari Sabandar ◽  
Jamia Azdina Jamal
Keyword(s):  
Xanthine Oxidase ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Oxidase Inhibitor ◽  
Bone Diseases ◽  
Spectroscopic Techniques ◽  
Xanthine Oxidase Inhibitor ◽  
Margaric Acid ◽  
Bioassay Guided Fractionation

Abstract Background In traditional Malay medicine, Marantodes pumilum (Blume) Kuntze (family Primulaceae) is commonly used by women to treat parturition, flatulence, dysentery, dysmenorrhea, gonorrhea, and bone diseases. Preliminary screening of some Primulaceae species showed that they possess xanthine oxidase inhibitory activity. Thus, this study aimed to investigate the xanthine oxidase inhibitory activity of three varieties of M. pumilum and their phytochemical compounds. Method Dichloromethane, methanol, and water extracts of the leaves and roots of M. pumilum var. alata, M. pumilum var. pumila, and M. pumilum var. lanceolata were tested using an in vitro xanthine oxidase inhibitory assay. Bioassay-guided fractionation and isolation were carried out on the most active extract using chromatographic techniques. The structures of the isolated compounds were determined using spectroscopic techniques. Results The most active dichloromethane extract of M. pumilum var. pumila leaves (IC50 = 161.6 μg/mL) yielded one new compound, 3,7-dihydroxy-5-methoxy-4,8-dimethyl-isocoumarin (1), and five known compounds, viz. ardisiaquinone A (2), maesanin (3), stigmasterol (4), tetracosane (5), and margaric acid (6). The new compound was found to be the most active xanthine oxidase inhibitor with an IC50 value of 0.66 ± 0.01 μg/mL, which was not significantly different (p > 0.05) from that of the positive control, allopurinol (IC50 = 0.24 ± 0.00 μg/mL). Conclusion This study suggests that the new compound 3,7-dihydroxy-5-methoxy-4,8-dimethyl-isocoumarin (1), which was isolated from the dichloromethane extract of M. pumilum var. pumila leaves, could be a potential xanthine oxidase inhibitor.

Inhibitory effects of bioaccessible anthocyanins and procyanidins from apple, red grape, cinnamon on α-amylase, α-glucosidase and lipase

2020 ◽  
pp. 1-9
Author(s):  
Pınar Ercan ◽  
Sedef Nehir El
Keyword(s):  
Inhibitory Activity ◽  
Digestive Enzymes ◽  
Positive Control ◽  
Anthocyanin Content ◽  
Inhibitory Effects ◽  
Total Anthocyanin ◽  
Total Anthocyanin Content ◽  
Before And After ◽  
Red Grape

Abstract. The goals of this study were to determine and evaluate the bioaccessibility of total anthocyanin and procyanidin in apple (Amasya, Malus communis), red grape (Papazkarası, Vitis vinifera) and cinnamon (Cassia, Cinnamomum) using an in vitro static digestion system based on human gastrointestinal physiologically relevant conditions. Also, in vitro inhibitory effects of these foods on lipid (lipase) and carbohydrate digestive enzymes (α-amylase and α-glucosidase) were performed with before and after digested samples using acarbose and methylumbelliferyl oleate (4MUO) as the positive control. While the highest total anthocyanin content was found in red grape (164 ± 2.51 mg/100 g), the highest procyanidin content was found in cinnamon (6432 ± 177.31 mg/100 g) (p < 0.05). The anthocyanin bioaccessibilities were found as 10.2 ± 1%, 8.23 ± 0.64%, and 8.73 ± 0.70% in apple, red grape, and cinnamon, respectively. The procyanidin bioaccessibilities of apple, red grape, and cinnamon were found as 17.57 ± 0.71%, 14.08 ± 0.74% and 18.75 ± 1.49%, respectively. The analyzed apple, red grape and cinnamon showed the inhibitory activity against α-glucosidase (IC50 544 ± 21.94, 445 ± 15.67, 1592 ± 17.58 μg/mL, respectively), α-amylase (IC50 38.4 ± 7.26, 56.1 ± 3.60, 3.54 ± 0.86 μg/mL, respectively), and lipase (IC50 52.7 ± 2.05, 581 ± 54.14, 49.6 ± 2.72 μg/mL), respectively. According to our results apple, red grape and cinnamon have potential to inhibit of lipase, α-amylase and α-glucosidase digestive enzymes.

scholarly journals Ingol and Ingenol-Type Diterpenes from Euphorbia trigona Miller with Keratinocyte Inhibitory Activity

Plants ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1206
Author(s):  
Reham Hammadi ◽  
Norbert Kúsz ◽  
Csilla Zsuzsanna Dávid ◽  
Zoltán Behány ◽  
László Papp ◽  
...  
Keyword(s):  
Liquid Chromatography ◽  
Cytotoxic Activity ◽  
Inhibitory Activity ◽  
High Performance ◽  
Skin Condition ◽  
Positive Control ◽  
Active Species ◽  
The European Union ◽  
Ingenol Mebutate

Ingenol mebutate, isolated from Euphorbia peplus, is an ingenane-type diterpenoid, primarily used for the topical treatment of actinic keratosis, a premalignant skin condition. The aim of our work was to investigate other Euphorbia species to find structurally similar diterpenes that can be used as alternatives to ingenol mebutate. Pharmacological investigation of Euphorbia candelabrum, Euphorbia cotinifolia, Euphorbia ramipressa, and Euphorbia trigona revealed the potent keratinocyte (HPV-Ker cell line) inhibitory activity of these spurge species. From the methanolic extract of the aerial parts of Euphorbia trigona Miller, the most active species, five ingol (1–5) and four ingenane-type diterpenoids (6–9) were isolated by various chromatographic separation techniques, including open column chromatography, vacuum liquid chromatography, thin-layer chromatography, and high-performance liquid chromatography. The structures of the compounds were determined by NMR spectroscopic analysis and by comparison of the assignations with the literature data. The cytotoxic activity of the compounds against keratinocytes was tested in vitro by using ingenol mebutate as a positive control. Among the isolated compounds, two ingenane derivatives (6 and 7) exhibited remarkably stronger cytotoxic activity (IC50 values 0.39 μM and 0.32 μM, respectively) on keratinocytes than ingenol mebutate (IC50 value 0.84 μM). These compounds could serve as starting materials for further investigations to find alternatives to Picato® (with active substance ingenol mebutate), which was withdrawn from marketing authorization in the European Union.

scholarly journals In vivo hypotensive effect and in vitro inhibitory activity of some Cyperaceae species

2013 ◽  
Vol 49 (4) ◽  
pp. 803-809
Author(s):  
Monica Lacerda Lopes Martins ◽  
Henrique Poltronieri Pacheco ◽  
Iara Giuberti Perini ◽  
Dominik Lenz ◽  
Tadeu Uggere de Andrade ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Colorimetric Assay ◽  
Hypotensive Effect ◽  
Ace Inhibition ◽  
Inhibitory Effect ◽  
Positive Control ◽  
Total Phenolic ◽  
Before And After

In 1820, French naturalist August Saint Hillaire, during a visit in Espírito Santo (ES), a state in southeastern Brazil, reported a popular use of Cyperaceae species as antidote to snake bites. The plant may even have a hypotensive effect, though it was never properly researched. The in vitro inhibitory of the angiotensin converting enzyme (ACE) activity of eigth ethanolic extracts of Cyperaceae was evaluated by colorimetric assay. Total phenolic and flavonoids were determined using colorimetric assay. The hypotensive effect of the active specie (Rhychonospora exaltata, ERE) and the in vivo ACE assay was measured in vivo using male Wistar Kyoto (ERE, 0.01-100mg/kg), with acetylcholine (ACh) as positive control (5 µg/kg, i.v.). The evaluation of ACE in vivo inhibitory effect was performed comparing the mean arterial pressure before and after ERE (10 mg/kg) in animals which received injection of angiotensin I (ANG I; 0,03, 03 and 300 µg/kg, i.v.). Captopril (30 mg/kg) was used as positive control. Bulbostylis capillaris (86.89 ± 15.20%) and ERE (74.89 ± 11.95%, ERE) were considered active in the in vitro ACE inhibition assay, at 100 µg/mL concentration. ACh lead to a hypotensive effect before and after ERE's curve (-40±5% and -41±3%). ERE showed a dose-dependent hypotensive effect and a in vivo ACE inhibitory effect. Cyperaceae species showed an inhibitory activity of ACE, in vitro, as well as high content of total phenolic and flavonoids. ERE exhibited an inhibitory effect on both in vitro and in vivo ACE. The selection of species used in popular medicine as antidotes, along with the in vitro assay of ACE inhibition, might be a biomonitoring method for the screening of new medicinal plants with hypotensive properties.

scholarly journals Design, Synthesis and Pharmacological Evaluation of Novel Imidazopyridine Analogues as Proton Pump Antagonist

2020 ◽  
Vol 32 (4) ◽  
pp. 776-782
Author(s):  
Ravindra S. Sonawane ◽  
Kiran D. Patil ◽  
Avinash V. Patil
Keyword(s):  
Spectral Analysis ◽  
Proton Pump Inhibitors ◽  
Proton Pump ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Docking Studies ◽  
Design Synthesis ◽  
Standard Drug ◽  
Imidazopyridine Derivatives

A series of novel imidazopyridine derivatives as proton pump inhibitors was designed with compounds of CID data base and explored considering AZD0865 as standard. Many compounds were identified and docked in proton pump ATPase pocket (PDB ID: 4ux2). Molecular docking studies revealed that many compounds showed good proton pump ATPase inhibitory activity. The docking poses revealed the interaction of ligands with amino acid. The standard drug AZD0865 had docking score of -7.112302 and displayed interactions with Asn138 and Asp137. A series of novel imidazopyridine derivatives as proton pump inhibitors were docked, synthesized and characterized by IR, NMR, CHN and MS spectral analysis. The target imidazopyridines were prepared from substituted 2-aminonicotinic acid and 2-bromo-1-substituted ethanone. in vitro Studies explained that few compounds exhibited moderate to good proton pump ATPase inhibitory activity in comparison with the reference drugs i.e. AZD0865. Compounds 11 and 12 shown higher activities with the IC50 4.3. Compounds 1, 4, 6, 7, 8, 10 and 13 showed weak anti-ulcer activity with its IC50 5.2, 5.8, 5.5, 5.1, 4.9, 4.6 and 5.9 and positive control AZD0865 shown IC50 2.0.

scholarly journals LOWERING URIC ACID EFFICACY TEST OF THE COMBINED EXTRACT OF UNCARIA GAMBIR (HUNTER) ROXB. AND CAESALPINIA SAPPAN L. IN VIVO AND IN VITRO

2018 ◽  
Vol 11 (8) ◽  
pp. 166
Author(s):  
Sri Ningsih ◽  
Fahri Fahrudin
Keyword(s):  
Antioxidant Activity ◽  
Uric Acid ◽  
Inhibitory Activity ◽  
Positive Control ◽  
Polyphenol Content ◽  
Caesalpinia Sappan ◽  
In Vivo Experiments ◽  
A Value

 Objective: Hyperuricemia (high uric acid levels) prevalence increased year by year. This study was aimed to elaborate the in vitro xanthine oxidase (XO) inhibitory activity and in vivo lowering hyperuricemic effect of Uncaria gambir (Hunter) Roxb) (gambir), Caesalpinia sappan L. (secang) and the combined extract of secang and gambir (formulae extract [FE]).Methods: Gambir and secang extracts were prepared by maceration with ethanol and FE was the proportioned combination of these two extracts. XO inhibitory activity was determined by measuring the formation of uric acid in the xanthine/XO system in vitro using allopurinol as a positive control at 100 ug/mL. Antioxidant activity was by 1,1-diphenyl-2-picrylhydrazyl radical reducing methods. The in vivo experiments were conducted in the oxonate-induced hyperuricemia rat model, in which FE was gavaged p.o. at the arrange dose of 75, 150, and 300 mg/kg bw for 2 weeks. Polyphenol content was measured using Folin–Ciocalteu reagent spectrophotometrically.Results: The XO inhibitory activity of FE was 80% of allopurinol, while secang and gambir were 98% and 50%, respectively. The strength was appropriate to the total polyphenol content, in which it decreased in the order of secang (99%) > FE (86%) > gambir (46%). Furthermore, FE at all tested doses was able to decrease uric acid levels. FE also demonstrated antioxidant activity with a value of 74% relative to Vitamin C at 4 ug/mL.Conclusion: These studies could be concluded that FE exhibited the ability to decrease uric acid level so that it was potential to be developed further as a uric acid-lowering agent.

scholarly journals COMPARISON OF α –GLUCOSIDASE INHIBITORY ACTIVITY OF Moringa oleifera ETHANOLIC EXTRACT

2021 ◽  
Vol 9 (Spl-2-ICOPMES_2020) ◽  
pp. S269-S273
Author(s):  
Rizky Rahmwaty Alami ◽  
◽  
Herlina Rante ◽  
Yulia Yusrini Djabir ◽  
◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Moringa Oleifera ◽  
Ethanolic Extract ◽  
Ethanol Extract ◽  
Positive Control ◽  
Glucosidase Inhibitor ◽  
Plant Samples

The purpose of this research was to determine the α-glucosidase enzyme inhibitory activity of Moringa oleifera plant samples collected from the three geographical areas viz., Saragi, Bacuhau, and Batumatongka of Southeast Sulawesi Indonesia. Ethanol extract of Moringa leaves was prepared by the maceration method using 95% ethanol. The estimation of α –glucosidase inhibitory activity of this extract was performed in vitro. The results of the study showed that ethanolic extract of three Moringa samples i.e. Sarangi, Bacuhau, and Batumatongka had the IC50value of 18.62, 10.18, 10.58 ppm, respectively while IC50value for the acarbose positive control was reported 11.54ppm. From the results of this study, it can be concluded that ethanolic extract of Moringa could inhibit α –glucosidase and this potential was similar to the commercial α –glucosidase inhibitor acarbose.

scholarly journals Synthesis of new 3-(substituted-phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents

2018 ◽  
Vol 9 (1) ◽  
pp. 13-21 ◽  
Author(s):  
Chandrakant Pawar ◽  
Dattatraya Pansare ◽  
Devanand Shinde
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
1H Nmr ◽  
13C Nmr ◽  
Antiproliferative Activity ◽  
Positive Control ◽  
Antiproliferative Agents ◽  
Ic50 Values ◽  
Mcf 7

In the present work, we report the synthesis of a series of 3-(substituted phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives through Suzuki and Buchwald reaction. We have optimized methodology for targets from milligram to multi-gram scale. The newly synthesized compounds were characterized by 1H NMR, 19F NMR, 13C NMR, LC-MS techniques and purity was further checked by HPLC. The compounds were evaluated for their in-vitro antiproliferative activity against MCF-7, HeLa, A-549 and Du-145 cancer cell lines by CCK-8 assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees and 5-fluorouracil was used as positive control. Among these compounds 2d, 2g, 2i, 4e, 4h and 4k are most active compared to the standard. All the synthesized compounds show IC50 values from 1.82-9.52 µM in different cell lines. Amongst these, compounds 2d, 2g, 2i, 4e, 4h and 4k were most potent, with IC50 values ranging from 1.82-4.28 µM in different cell lines.

scholarly journals A New Flavone Glycoside From Lumnitzera littorea with In Vitro α-Glucosidase Inhibitory Activity

2019 ◽  
Vol 14 (6) ◽  
pp. 1934578X1985136
Author(s):  
Nguyen T. L. Thuy ◽  
Pham T. Thuy ◽  
Bui T. Tung ◽  
Huynh T. Loc ◽  
Truong T. T. Dang ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
High Resolution Mass Spectrometry ◽  
Positive Control ◽  
Mass Spectrometry Analysis ◽  
Two Dimensional ◽  
Flavone Glycoside ◽  
One Dimensional ◽  
Spectrometry Analysis ◽  
Resolution Mass

A new flavone glycoside, lumnitzerone (1), was isolated from leaves of Lumnitzera littorea, together with 9 known flavonoids. Their structures were elucidated by spectroscopic (one-dimensional, two-dimensional nuclear magnetic resonance) and high-resolution mass spectrometry analysis, and comparison with literature data. Extracts and all isolated compounds were evaluated for α-glucosidase inhibitory activity; all the extracts and most of the isolated compounds exhibited better activities than the positive control acarbose.

scholarly journals IN VITRO SCREENING OF ANTIOXIDANT AND ANTIAGING POTENTIAL OF CUCUMIS SATIVUS FRUIT EXTRACT

2020 ◽  
pp. 187-190
Author(s):  
CHANCHAL GARG ◽  
RAVINDER SINGH ◽  
MUNISH GARG
Keyword(s):  
Ethyl Acetate ◽  
Cucumis Sativus ◽  
Inhibitory Activity ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Ethyl Acetate Fraction ◽  
Positive Control ◽  
Dpph Radical ◽  
Dpph Radical Scavenging

Objective: The present study was designed to screen the anti-aging and anti-wrinkle potential of Cucumis sativus fruit through in vitro estimation of antioxidant, anti-hyaluronidase, anti-elastase, anti-collagenase/anti-matrix metalloproteinase (MMP)-1, and anti-tyrosinase activity. Methods: Raw juice of cucumber was taken, filtered and fractionated with ethyl acetate and n-butanol. The obtained extracts were then evaluated for their antioxidant potential through 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging assay taking ascorbic acid as positive control and other enzymatic activities in reference to hyaluronidase inhibition, MMP-1/collagenase inhibition, and elastase inhibition taking catechin as reference standard whereas for tyrosinase inhibition the standard used was quercetin. Results: All the evaluations were performed in triplicates and results were noted down. It was observed that aqueous extract of C. sativus fruits showed a maximum DPPH radical scavenging activity (p<0.0001), half-maximal inhibitory concentration (IC50) at a concentration of 122.67 μg/ml. The ethyl acetate fraction of C. sativus fruits exhibited maximum hyaluronidase (p<0.0001), MMP-1/collagenase (p<0.04), and tyrosinase (p<0.04) inhibitory activity, IC50 at a concentration of 59.54, 45.79, and 24.46 μg/ml, respectively. The elastase (p<0.0001) inhibitory activity by n-butanol fraction of C. sativus fruits extract was maximum, IC50 at a concentration of 52.76 μg/ml. Conclusion: A potent anti-aging and anti-wrinkle properties were well demonstrated by C. sativus, as depicted from the results obtained.

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