Comparative Study of Synthesis, Structural and Antioxidant Activity In Vitro of Some New Carboxylic α,α-diaminodiesters Derivatives

Considering the richness of heterocyclic chemistry, and the diversity of applications it possesses, in the present work we were interested in preparing new polyfunctional α,α-diaminodiesters derived from glycine, via the N-alkylation reaction of methyl 2-azido-2-benzamidoacetate with a series of heterocyclic and non-heterocyclic carboxylic aminoesters, using different bases. The structures of the synthesized molecules were characterized by 1D and 2D NMR spectroscopy, mass spectrometry (MS-ESI) and elemental analysis. Two compounds from this series were isolated as single crystals and their chemical structures were determined by X-ray diffraction. The antioxidant effect of the synthesized compounds was tested in vitro using the free radical scavenging power (DPPH) and reducing power (FRAP) tests. The results show that the different extracts tested have a relatively high antioxidant power compared to the positive control considered, especially for the compound methyl 2-benzamido-2-(2-methoxy-2-oxo-1-phenylethyl)amino)acetate, which showed a very strong antiradical power and reducing power.

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Phytochemical Screening, Polyphenols Content, Antioxidant Power, and Antibacterial Activity of Herniaria hirsuta from Morocco

The Scientific World JOURNAL ◽

10.1155/2018/7470384 ◽

2018 ◽

Vol 2018 ◽

pp. 1-7 ◽

Cited By ~ 1

Author(s):

Kenza Ammor ◽

Dalila Bousta ◽

Sanae Jennan ◽

Bahia Bennani ◽

Abdellah Chaqroune ◽

...

Keyword(s):

Antibacterial Activity ◽

Antioxidant Activities ◽

Radical Scavenging ◽

Reducing Power ◽

Antibacterial Activities ◽

Diffusion Method ◽

Antioxidant Power ◽

Negative Effect ◽

Hydroethanolic Extract

The aim of this study is to investigate in vitro antioxidant and antibacterial activities of the aqueous and hydroethanolic extracts for aerial parts of Herniaria hirsuta. Extracts were screened for their possible antioxidant activities by three tests: DPPH free radical-scavenging, reducing power, and molybdenum systems. The screening of antibacterial activity of extracts was individually evaluated against sixteen bacteria species using a disc diffusion method. Flavonoids, total phenols, and tannins content were performed for both extracts. It shows higher content in the hydroethanolic extract. The hydroethanolic extract showed a significant antioxidant activity for the three methods studies to the aqueous extract, but nonsignificant results compared to the reference (BHT). However, both extracts have negative effect on the strains studies for the antibacterial activity.

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Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

Planta Medica ◽

10.1055/a-1617-7573 ◽

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).

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Chemical Profiling and Biological Properties of Extracts from Different Parts of Colchicum Szovitsii Subsp. Szovitsii

Antioxidants ◽

10.3390/antiox8120632 ◽

2019 ◽

Vol 8 (12) ◽

pp. 632 ◽

Cited By ~ 1

Author(s):

Gabriele Rocchetti ◽

Biancamaria Senizza ◽

Gokhan Zengin ◽

Murat Ali Okur ◽

Domenico Montesano ◽

...

Keyword(s):

Biological Activities ◽

Radical Scavenging ◽

Reducing Power ◽

Extraction Methods ◽

Biological Properties ◽

Leaf Extracts ◽

Orthogonal Projections ◽

Antioxidant Power ◽

Latent Structures

Like other members of the Colchicum genus, C. szovitsii subsp. szovitsii is also of medicinal importance in Turkish traditional medicine. However, its biological properties have not been fully investigated. Herein, we focused on the evaluation of the in vitro antioxidant and enzyme inhibitory effects of flower, root and leaf extracts, obtained using different extraction methods. In addition, a comprehensive (poly)-phenolic and alkaloid profiling of the different extracts was undertaken. In this regard, ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS) allowed us to putatively annotate 195 polyphenols and 87 alkaloids. The most abundant polyphenols were flavonoids (83 compounds), whilst colchicine and 2-demethylcolchicine were some of the most widespread alkaloids in each extract analyzed. However, our findings showed that C. szovitsii leaf extracts were a superior source of both total polyphenols and total alkaloids (being, on average 24.00 and 2.50 mg/g, respectively). Overall, methanolic leaf extracts showed the highest (p < 0.05) ferric reducing antioxidant power (FRAP) reducing power (on average 109.52 mgTE/g) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging (on average 90.98 mgTE/g). Interestingly, each C. szovitsii methanolic extract was more active than the water extracts when considering enzymatic inhibition such as against tyrosinase, glucosidase, and acetylcholinesterase (AChE). Strong correlations (p < 0.01) were also observed between polyphenols/alkaloids and the biological activities determined. Multivariate statistics based on supervised orthogonal projections to latent structures discriminant analysis (OPLS-DA) allowed for the detection of those compounds most affected by the different extraction methods. Therefore, this is the first detailed evidence showing that C. szovitsii subsp. szovitsii might provide beneficial effects against oxidative stress and the associated chronic diseases. Nevertheless, the detailed mechanisms of action need to be further investigated.

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Antioxidant Activities of Extracts from Sarcocarp of Cotoneaster multiflorus

Journal of Chemistry ◽

10.1155/2018/4619768 ◽

2018 ◽

Vol 2018 ◽

pp. 1-7 ◽

Cited By ~ 3

Author(s):

Xiangping Liu ◽

Jia Jia ◽

Xuemin Jing ◽

Guoliang Li

Keyword(s):

Ethyl Acetate ◽

Antioxidant Activities ◽

Radical Scavenging ◽

Water Extract ◽

Reducing Power ◽

Ethyl Acetate Fraction ◽

Dependent Manner ◽

Antioxidant Power ◽

Water Fraction

The ethanol-water (7 : 3, v/v) extract of Cotoneaster multiflorus sarcocarp was sequentially fractionated by liquid-liquid partition using n-hexane, diethyl ether, methylene dichloride, and ethyl acetate. The contents of total polyphenols, total flavones, and oligomeric proanthocyanidins in the five parts (including the ethanol-water extract) were determined. In addition, 2,2-diphenyl-1-picrylhydrazyl free radical-scavenging, 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt radical cation decolorization, reducing power, ferric reducing antioxidant power, and lipid peroxidation inhibition assays were conducted to test the antioxidant activities of Sample 1 (the ethanol-water fraction) and Sample 2 (the ethyl acetate fraction) in vitro. In the above five assays, Sample 2 showed greater antioxidant capacities than Sample 1. Furthermore, Sample 2 was better able to protect low-density lipoproteins from oxidation in a dose-dependent manner. The test results show that C. multiflorus sarcocarp, especially the ethyl acetate-soluble fraction, may be a potential source of natural antioxidants.

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In vitro Antioxidant Activities and Effect of Hydroethanolic and Aqueous Extracts of Terminalia avicennioides (Combretaceae) on Salmonella

Microbiology Research Journal International ◽

10.9734/mrji/2020/v30i130185 ◽

2020 ◽

pp. 1-14

Author(s):

Louis-Claire Ndel Famen ◽

Benjamin Tangue Talom ◽

Richard Simo Tagne ◽

Gabriel Tchuente Kamsu ◽

Norbert Kodjio ◽

...

Keyword(s):

Typhoid Fever ◽

Antioxidant Activities ◽

Radical Scavenging ◽

Reducing Power ◽

Public Health Problem ◽

Stem Bark ◽

Poor Quality ◽

Antioxidant Power ◽

Good Ability

Today, Typhoid fever remains a public health problem in developing countries due to the poor quality of lifestyle associated with abusive and inappropriate use of antibiotics. Aims: Considering the ethnopharmacological relevance of Terminalia avicennioides (T. avicennioides) (Combretaceae), this study was designed to investigate the in vitro antisalmonella and antioxidant activities of various extracts of this plant. Methodology: The microdilution method was used to determine the Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) of T. avicennioides extract. These extracts were also subjected to in vitro antioxidant tests such as diphényl-2-picrylhydrazyle (DPPH) radical scavenging test, ferric reducing-antioxidant power (FRAP), hydroxyl radical (OH) nitric oxide (NO) and Hydrogen Peroxide Scavenging Capacity. Results: In vitro antisalmonella activity reveals that T. avicennioides stem bark extracts presented MIC values ranging from 64 to 512 μg / mL on tested microorganisms. This extract exhibited a good ability to trap DPPH with an IC50 of 8.30 μg / mL. The iron reducing power obtained with this extract had ODs ranging from 0.96 to 1.63. Phytochemical screening showed the presence of alkaloids, flavonoids, saponins, phenols anthocyanin and anthraquinone in all the extracts. Conclusion: The results suggest that stem extract of T. avicennioides contains antisalmonella and antioxidant substances, which could be used for the treatment of typhoid fever and another salmonellosis.

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Papaver Decaisnei: GC-MS Alkaloids Profiling, in Vitro Antioxidant, and Anticancer Activity

10.21203/rs.3.rs-1207324/v1 ◽

2022 ◽

Author(s):

Ahmed Aj.Jabbar ◽

Fuad Othman Abdullah ◽

Kamaran Kaiani Abdulrahman ◽

yaseen Galali ◽

Abdullah Sh. Sardar

Keyword(s):

Antioxidant Activity ◽

Radical Scavenging ◽

Reducing Power ◽

Phytochemical Analysis ◽

Endemic Plant ◽

Anticancer Activities ◽

Antioxidant Power ◽

Leaves And Roots ◽

Mcf 7

Abstract The Papaver L. plant have been well known as a source of pharmaceutically valuable alkaloids (noscapine, thebaine, codeine, roemerine, papaverine and morphine). The current study investigates the phytochemical, in-vitro antioxidant, and anticancer activities of papaver decaisnei, an endemic plant species to the flora of Kurdistan-Iraq. The chemical analysis of the methanolic (MeOH) extracts of flowers, leaves, and roots of papaver decaisnei were made by using gas chromatography-mass spectrophotometry (GC-MS), and the antioxidant activity evaluation done by radical scavenging [on 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2j-azino-bis (3- ethylbenzothiazoline-6-sulfonic acid) (ABTS)], and reducing power [cupric reducing antioxidant capacity (CUPRAC), and ferric reducing antioxidant power (FRAP)] assays. The anticancer actions were presented as IC50 (inhibitory concentration at 50%) on human colorectal adenocarcinoma (Caco-2), mammary cancer cells (MCF-7), and human cervical carcinoma (HeLa) cells. The results of the phytochemical analysis showed 17, 19, and 22 chemical compounds for flowers, leaves, and roots of P. decaisnei, respectively. The prevalent organic compounds of P. decaisnei were alkaloids, phenolics, fatty acids, esters, and phytosterols, namely Roemerine (70.44%), Decarbomethoxytabersonine, 9,12,15-Octadecatrien-1-ol, Hexadecanoic acid, 6,8-Dioxa-3-thiabicyclo(3,2,1)octane 3,3-dioxide, and γ-Sitosterol. The antioxidant activity of plant organ extracts was within 39.1-143.5 μg/ml for DPPH and 123.12-276.4 μg/ml for ABTS assays, while, the FRAP and CUPRAC values ranged within 12.4- 34.3 and 42.6-75.8 μg/ml, respectively. The anticancer action of P.decaisnei organ extracts was found against all tested human cell lines (Caco-2, MCF-7, HeLa) with inhibitory concentrations (IC50) values between 125.3-388.4 μg/ml. The presented data on alkaloid contents and biological activity of P. decaisnei can serve a ground knowledge for the future biomedical synthesis and cancer research projects.

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Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro

Molecules ◽

10.3390/molecules26010042 ◽

2020 ◽

Vol 26 (1) ◽

pp. 42

Author(s):

Katrin Kuck ◽

Guido Jürgenliemk ◽

Bartosz Lipowicz ◽

Jörg Heilmann

Keyword(s):

Ethanolic Extract ◽

2D Nmr ◽

Preparative Hplc ◽

Reference Compound ◽

2D Nmr Spectroscopy ◽

Vitro Assay ◽

Chemical Structures ◽

Inflammatory Processes ◽

First Time

By using various chromatographic steps (silica flash, CPC, preparative HPLC), 16 sesquiterpenes could be isolated from an ethanolic extract of myrrh resin. Their chemical structures were elucidated by 1D and 2D NMR spectroscopy and HRESIMS. Among them, six previously unknown compounds (1–6) and another four metabolites previously not described for the genus Commiphora (7, 10, 12, 13) could be identified. Sesquiterpenes 1 and 2 are novel 9,10-seco-eudesmanes and exhibited an unprecedented sesquiterpene carbon skeleton, which is described here for the first time. New compound 3 is an 9,10 seco-guaian and the only peroxide isolated from myrrh so far. Compounds 1, 2, 4, 7–9, 11, 13–16 were tested in an ICAM-1 in vitro assay. Compound 7, as well as the reference compound furanoeudesma-1,3-diene, acted as moderate inhibitors of this adhesion molecule ICAM-1 (IC50: 44.8 and 46.3 μM, respectively). These results give new hints on the activity of sesquiterpenes with regard to ICAM-1 inhibition and possible modes of action of myrrh in anti-inflammatory processes.

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EVALUATION OF IN VITRO- ANTI-OXIDANT POTENTIAL OF AQUEOUS ROOT EXTRACT OF CLERODENDRUM SERRATUM L.

Asian Journal of Pharmaceutical and Clinical Research ◽

10.22159/ajpcr.2017.v10i4.16930 ◽

2017 ◽

Vol 10 (4) ◽

pp. 402

Author(s):

Raj Kumar Tiwari ◽

Udayabanu Malairaman ◽

Silpi Chanda

Keyword(s):

Radical Scavenging ◽

Reducing Power ◽

Antioxidant Property ◽

Root Extract ◽

Antioxidant Power ◽

Ic50 Values ◽

Ferric Reducing Antioxidant Power ◽

Dpph Scavenging ◽

Aqueous Root Extract

Objective: The intent of this report was to investigate the effect of aqueous root extract of Clerodendrum serratum L. for antioxidant activity using divergent models viz. DPPH scavenging assay, Superoxide scavenging assay and Ferric Reducing Antioxidant Power (FRAP) assay.Materials and Methods: The root of C. serratum was extracted using water. The yield of aqueous extract was 10%w/w. The outcome was examined statistically by the regression method.Results and discussions: The IC50 values are 85.43 µg/ml and 107.59 µg/ml for DPPH radical scavenging and Superoxide scavenging assay respectively whereas FRAP showed significant reducing power activity with increased concentration of sample. The pilot study showed, a significant correlation existed between concentrations of the extract and percentage engrossment of free radicals.Conclusion: The antioxidant property may be corresponding to the polyphenols and flavonoids adjacent in the extract. These results clearly revealed that C. serratum might be effective against diseases analogous with free radical mediated. Keywords Clerodendrum serratum, DPPH, Superoxide, FRAP, Rutin, Antioxidant

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Briarenones A‒C, New Briarellin Diterpenoids from the Gorgonian Briareum violaceum

Marine Drugs ◽

10.3390/md17020120 ◽

2019 ◽

Vol 17 (2) ◽

pp. 120 ◽

Cited By ~ 1

Author(s):

Yang Cheng ◽

Atallah Ahmed ◽

Raha Orfali ◽

Chang-Feng Dai ◽

Jyh-Horng Sheu

Keyword(s):

Cytochalasin B ◽

2D Nmr ◽

Human Neutrophils ◽

Superoxide Anions ◽

X Ray Diffraction ◽

X Ray ◽

Chemical Structures ◽

Spectroscopic Analyses ◽

Phenyl Alanine

Three new eunicellin-derived diterpenoids of briarellin type, briarenones A‒C (1‒3), were isolated from a Formosan gorgonian Briareum violaceum. The chemical structures of the compounds were elucidated on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR. The absolute configuration of 1 was further confirmed by a single crystal X-ray diffraction analysis. The in vitro cytotoxic and anti-inflammatory potentialities of the isolated metabolites were tested against the growth of a limited panel of cancer cell lines and against the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine and cytochalasin B (fMLF/CB)-stimulated human neutrophils, respectively.

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Antioxidant Activities of Stilbenoids fromRheum emodiWall

Evidence-based Complementary and Alternative Medicine ◽

10.1155/2012/603678 ◽

2012 ◽

Vol 2012 ◽

pp. 1-7 ◽

Cited By ~ 11

Author(s):

Yuan-yuan Chai ◽

Fang Wang ◽

Yan-li Li ◽

Ke Liu ◽

Hui Xu

Keyword(s):

Antioxidant Activity ◽

Antioxidant Activities ◽

Inflammatory Diseases ◽

Radical Scavenging ◽

Reducing Power ◽

Antioxidant Potential ◽

Hydroxyl Group ◽

Antioxidant Power

Rheum emodiWall has been reported to possess protective effect in many inflammatory diseases and oxidative stress-related injuries. This study aims to investigate antioxidant power of stilbenoids fromR. emodiand then explore the material basis for its antioxidant potential. The most abundant stilbenoid piceatannol-4′-O-β-D-glucopyranoside (PICG) and its aglycon piceatannol (PICE) were isolated fromR. emodirhizome. Using well-accepted antioxidant chemicals as reference, antioxidant activity of these stilbenoids was examined by measuring DPPH and superoxide anion radical scavenging, ferric reducing power, and inhibition of lipid peroxidationin vitro. Both PICG and PICE displayed promising antioxidant activity in all the four assays. Comparisons among the tested compounds indicated that PICE has the most potent antioxidant activity and the presence of 3′-hydroxyl group may enhance antioxidant activity of stilbenoids. The antioxidative effect of PICE at the cellular level was further demonstrated on the model of hydrogen-peroxide-induced H9c2 rat cardiomyoblasts injury. Taking into account the rapidin vivometabolic transformation of PICG into PICE it can be inferred that the most abundant stilbenoid PICG may be an important constituent responsible for the antioxidant potential ofR. emodiand promising to be developed as an antioxidant agent for supplementary or therapeutic use.

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