scholarly journals Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

2016 ◽  
Vol 12 ◽  
pp. 29-42 ◽  
Author(s):  
Miriana Kfoury ◽  
David Landy ◽  
Steven Ruellan ◽  
Lizette Auezova ◽  
Hélène Greige-Gerges ◽  
...  

Carvacrol and thymol have been widely studied for their ability to control food spoilage and to extend shelf-life of food products due to their antimicrobial and antioxidant activities. However, they suffer from poor aqueous solubility and pronounced flavoring ability that limit their application in food systems. These drawbacks could be surpassed by encapsulation in cyclodextrins (CDs). Applications of their inclusion complexes with CDs were reported without investigating the inclusion phenomenon in deep. In this study, inclusion complexes were characterized in terms of formation constants (K f), complexation efficiency (CE), CD:guest molar ratio and increase in bulk formulation by using an UV–visible competitive method, phase solubility studies as well as 1H and DOSY 1H NMR titration experiments. For the first time, a new algorithmic treatment that combines the chemical shifts and diffusion coefficients variations for all guest protons was applied to calculate K f. The position of the hydroxy group in carvacrol and thymol did not affect the stoichiometry of the inclusion complexes but led to a different binding stability with CDs. 2D ROESY NMR experiments were also performed to prove the encapsulation and illustrate the stable 3D conformation of the inclusion complexes. The structural investigation was accomplished with molecular modeling studies. Finally, the radical scavenging activity of carvacrol and thymol was evaluated by the ABTS radical scavenging assay. An improvement of this activity was observed upon encapsulation. Taken together, these results evidence that the encapsulation in CDs could be valuable for applications of carvacrol and thymol in food.

Processes ◽  
2020 ◽  
Vol 9 (1) ◽  
pp. 26
Author(s):  
Teodora Balaci ◽  
Bruno Velescu ◽  
Oana Karampelas ◽  
Adina Magdalena Musuc ◽  
George Mihai Nițulescu ◽  
...  

The aim of our study was to obtain rutoside (RUT) inclusion complexes in β-cyclodextrin (β-CD) and in hydroxypropyl-β-cyclodextrin (HP-β-CD), in a 1:1 molar ratio, using the lyophilization method of complexation in solution. The complexes were confirmed and characterized, in comparison with the raw materials and their simple physical mixtures, by SEM, DSC, and FT-IR analyses. The antioxidant activity of the compounds was assessed by using the 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and 2’-azino-bis(3-ethylbenzothiazolin-6-sulfonic) acid (ABTS) radicals, determining the radical scavenging activity, and by ferric reducing antioxidant power (FRAP) assay. The results revealed superior antioxidant ability for the inclusion complexes towards rutoside alone. The inclusion complexes were used as active ingredients in formulations of immediate-release tablets. The preformulation studies were performed on the powders for direct compression obtained after mixing the active ingredients with the excipients (Avicel PH 102, Polyplasdone XL-10, magnesium stearate, and talc). The materials were assessed for particle size, flowability, compressibility, and moisture content, establishing they are suitable for a direct compression process. The tablets were characterized regarding their pharmaco-technical properties and the results proved that the formulations lead to high-quality delivery systems, showing a good mechanical resistance with a low friability, excellent disintegration times, and satisfying dissolution rate. The performances were very similar for both formulations and the physico-mechanical properties of the tablets are not influenced by type of the used cyclodextrin, but the RUT- HP-β-CD tablets presented a higher dissolution rate.


2020 ◽  
Vol 8 (3) ◽  
pp. 9-13
Author(s):  
Purnamasari Nur Aini ◽  
Dzakwan Muhammad ◽  
Pramukantoro Ganet Eko ◽  
Mauludin Rachmat ◽  
El Fahmi

Background: Phytosomes are recently introduced drug delivery system and novel botanical formulation to produce lipophilic molecular complex to improve absorption and bioavailability of phytoconstituent. Myricetin is a well-known flavonoid with different biological effects and contributed in food preserving by free radical scavenging activity. However, bioavailability of myricetin is an important limiting factor for its antioxidant activities. Purpose: To overcome this limitation, in the present study we aimed to produce myricetin-loaded nano phytosomes to improve its physicochemical stability and bioavailability. Methods: myricetin-loaded nano phytosome was prepared by using phosphatidylcholine (PC) and cholesterol (CH). Myricetin nanophytosomes system was characterized by particle size analyzer, particle size distribution (PDI), encapsulation efficiency and potential antioxidant activity. Results: Results showed that formulation with the myricetin: PC: CH molar ratio of 1: 2: 0.8 had lower particle size (291.11 nm) and higher encapsulation efficiency percent (93%). Morphology analysis showed that myricetin nanophytosome spherical shape. The potential antioxidant data showed that incorporation myricetin in the phospholipid myricetin remained unchanged even after encapsulation of myricetin in binarynanophytosome formulation. Conclusion: Nano phytosomal formulation of myricetin showed promising potential in fortification of nutraceutical with water insoluble antioxidants.  


Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6840
Author(s):  
Zahraa Hammoud ◽  
Maya Kayouka ◽  
Adriana Trifan ◽  
Elwira Sieniawska ◽  
Jouda Mediouni Ben Jemâa ◽  
...  

The essential oil component α-pinene has multiple biological activities. However, its application is limited owing to its volatility, low aqueous solubility, and chemical instability. For the aim of improving its physicochemical properties, α-pinene was encapsulated in conventional liposomes (CLs) and drug-in-cyclodextrin-in-liposomes (DCLs). Hydroxypropyl-β-cyclodextrin/α-pinene (HP-β-CD/α-pinene) inclusion complexes were prepared in aqueous solution, and the optimal solubilization of α-pinene occurred at HP-β-CD:α-pinene molar ratio of 7.5:1. The ethanol-injection method was applied to produce different formulations using saturated (Phospholipon 90H) or unsaturated (Lipoid S100) phospholipids in combination with cholesterol. The size, the phospholipid and cholesterol incorporation rates, the encapsulation efficiency (EE), and the loading rate (LR) of α-pinene were determined, and the storage stability of liposomes was assessed. The results showed that α-pinene was efficiently entrapped in CLs and DCLs with high EE values. Moreover, Lipoid S100 CLs displayed the highest LR (22.9 ± 2.2%) of α-pinene compared to the other formulations. Both carrier systems HP-β-CD/α-pinene inclusion complex and Lipoid S100 CLs presented a gradual release of α-pinene. Furthermore, the DPPH radical scavenging activity of α-pinene was maintained upon encapsulation in Lipoid S100 CLs. Finally, it was found that all formulations were stable after three months of storage at 4 °C.


2019 ◽  
Author(s):  
Chem Int

In this study, we determined the chemical composition and antioxidant activities of the essential oils from two different varieties of khat (Catha edulis Forsk) cultivated in Ethiopia. The essential oils were extracted by hydrodistillation using the Clevenger type apparatus, identifications of compounds were made by gas chromatography and gas chromatography-mass spectrometry (GC-MS). Seventy seven different compounds were identified from essential oils of the two different khat cultivars. The essential oils in the samples from Bahir Dar and Wendo were composed of 50 and 34 compounds, respectively. The major compound identified in khat essentials oils include: limonene, 1-phenyl-1,2-propanedione, 1-hydroxy,1-phenyl-2-propanone, camphor, (sulfurous acid)-2-propylundecyl ester, hexadecane, O-mentha-1(7), 8-dien-3-ol, heptadecane, 10-methylnonadecane, (phthalic acid)-isobutyl octadecyl ester, and tritetracontane. The antioxidant and free radical scavenging activity of the oils were assessed by means of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical assay. The scavenging activities of the oils were 23.5-23.6 μg AAE/kg of fresh khat sample.


2011 ◽  
pp. 151-157 ◽  
Author(s):  
Marijana B. Saka ◽  
Julianna F. Gyura ◽  
Aleksandra Mišan ◽  
Zita I. Šereš ◽  
Biljana S. Pajin ◽  
...  

The antioxidant activity of cookies prepared by the addition of sugarbeet dietary fibers was investigated in order to estimate their influence on functional characteristics and shelf-life of cookies. Treated fiber (TF) was obtained from sugarbeet by extraction with sulfurous acid (75 °C at pH = 5.7during 60 min) and treatment with hydrogen peroxide (20 g/LH2O2 at pH = 11 during 24 h). The fiber obtained was dried (80 °C), ground and sieved. TF was investigated in comparison with commercially available Fibrex®. The cookies were prepared by the addition of 0, 7, 9 and 11% of sugarbeet dietary fiber as a substitute for wheat flour in the formulation of cookies. The antioxidant properties of cookies were tested every 7 days using a DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity test during 6 weeks of storage at room temperature (23 ± 1 ºC). The obtained results indicated that substitution of wheat flour with Fibrex® in the formulation of cookies upgraded the antioxidant activity, i.e. the functional characteristics of Fibrex®-enriched cookies and could prolong their shelf-life. In contrast, TF did not increase the antioxidant activity of TF-enriched cookies. The better antioxidant activities of Fibrex®-enriched cookies could be attributed to the presence of ferulic acid.


Author(s):  
Imane Rihab Mami ◽  
Noria Merad-Boussalah ◽  
Mohammed El Amine Dib ◽  
Boufeldja Tabti ◽  
Jean Costa ◽  
...  

Aim and Objective: Oxidative stress is implicated in the development and progression of many disease. Some of appropriate actions that could be initiated to taken to resolve the problem of these diseases are search for new antioxidant substances isolated from plants. The aims of this study were to study the intraspecies variations of A. verticillata and C. caeruleus essential oils from 8 locations using statistical analysis, the in vitro antioxidant properties of collective essential oils and in combinations. Materials and Methods: The essential oils were analyzed by GC and GC-MS. The intraspecies variations of the essential oil compositions were discussed using principal component analysis (PCA) and cluster analysis (CA). The antioxidant properties were evaluated DPPH-radical scavenging activity and β-carotene bleaching test. Results: The main components of Ammoides verticillata collective essential oil (Coll EO) were thymol (30.5%), carvacrol (23.2%), p-cymene (13.1%), limonene (12.5%) and terpinene-4-ol (12.3%). While roots of Carthamus caeruleus essential oil were dominated by carline oxide (86.2%). The chemical variability allowed the discrimination of two main Groups for both Coll EOs. A direct correlation between the altitudes, climate and the chemical compositions was evidenced. Ammoides verticulata and Carthamus caeruleus Coll Eos showed good antioxidant activity. In binary mixture, the interaction both Coll Eos and between oils rich of thymol and/or carvacrol with carlina oxide produced the best synergistic effects, compared to individual essential oils and the synthetic antioxidant (BHT). Conclusion: Ammoides verticillata and Carthamus caeruleus essential oil blends can be used as a natural food preservative and alternative to chemical antioxidants.


2019 ◽  
Vol 16 (3) ◽  
pp. 249-255
Author(s):  
Momin Khan ◽  
Umar Ali ◽  
Anis Ur Rahman ◽  
Muhammad Ibrahim ◽  
Abdul Hameed ◽  
...  

Background: The role of small molecules as antioxidants to prevent the oxidation of other molecules and inhibit them from radical formation is the area of much interest to cure disease especially cancer. Moreover, the antioxidants play important role as stabilizers to prevent oxidation of fuels and lubricants. </P><P> Methods: In the present study, fifteen tetrakis-Schiff’s bases derivatives (1-15) were synthesized and screened for their antioxidant activities. Compounds 1-15 were synthesized by continuous stirring of reaction mixture of 1,4-bis (hydrazonomethyl)benzene (1 mmol) with various substituted aromatic aldehydes (2 mmol) in distilled water using acetic acid as catalyst at room temperature for 2-10 min. </P><P> Results: Our present study showed that all compounds are better ferrous ion-chelating agents except compound 1,4-bis((E)-((E)-(3,4-dimethoxybenzylidene)hydrazono)methyl)benzene (6) (IC50 = 329.26 &#177; 4.75 &#181;M) which has slightly low activity than the standard EDTA (IC50 = 318.40 &#177; 5.53 μM). In addition, DPPH radical scavenging activity of eleven compounds showed higher activity than the standard. However, remaining four compounds showed comparable radical scavenging activity to the standard DPPH (IC50 = 257.77 &#177; 4.60 &#181;M). </P><P> Conclusion: The series of fifteen Schiff’s bases (1-15) were synthesized and evaluated as antioxidants. From both assays, it has been demonstrated that most of the tetrakis-Schiff’s bases have potential to serve as leads for the development of antioxidant agents for future research.


2020 ◽  
Vol 10 (2) ◽  
pp. 145-152 ◽  
Author(s):  
Imane Rihab Mami ◽  
Rania Belabbes ◽  
Mohammed El Amine Dib ◽  
Boufeldja Tabti ◽  
Jean Costa ◽  
...  

Background: Carthamus caeruleus belongs to the Asteraceae family. The roots are traditionally used as healing agents. They help to heal burns and treat skin diseases. They are also used against joint inflammation and are very effective against diseases such as irritable bowel syndrome for cancer patients. Objectives: The purpose of this work was i) to study the chemical composition of i) the essential oil and hydrosol extract of Carthamus caeruleus, ii) to isolate the major component of both extracts and iii) to evaluate their antioxidant, antifungal and insecticidal activities. Methods: The essential oil and hydrosol extract obtained from the roots were studied by GC and GC/MS. The antioxidant activities were performed using two different methods i) Radical scavenging activity (DPPH) and ii) the Ferric-Reducing Antioxidant Power (FRAP), using BHT as a positive control. Whereas, the antifungal activity of the essential oil and Carlina oxide was investigated against plant fungi. The fumigation toxicity of C. caeruleus essential oil besides Carlina oxide was evaluated against adults of Bactrocera oleae better known as the olive fly. Results: The essential oil and hydrosol extract were mainly represented by acetylenic compounds such as carline oxide and 13-methoxy carline oxide. Carlina oxide was isolated and identified by 1H and 13C NMR spectroscopic means. The results showed that Carlina oxide presented interesting antioxidant and antifungal properties, while C. caeruleus root essential oil had better insecticidal activity. Furthermore, Carlina oxide has demonstrated promising in vivo antifungal activity to control infection of apples by Penicillium expansum. Conclusion: Carlina oxide can be used as a natural food preservative and alternative to chemical fungicides to protect stored apple against Penicillium expansum.


2020 ◽  
Vol 10 (3) ◽  
pp. 312-321
Author(s):  
Idin Sahidin ◽  
Carla W. Sabandar ◽  
Wahyuni ◽  
Rini Hamsidi ◽  
Sandra Aulia Mardikasari ◽  
...  

Background: Marine sponges provided a great source of natural products with promising biological activity. This study was aimed to investigate the chemical constituents of methanol extracts of selected Indonesian marine sponges (Callyspongia sp., Clathria sp., Melophlus sarasinorum, and Xestospongia sp.), collected from the Saponda Islands, Southeast Sulawesi, Indonesia as well as to evaluate their antimicrobial and antioxidant activities. Methods: LCMS/MS analysis used to identify the compounds. Agar well diffusion and DPPH assays were used to evaluate the antimicrobial and antioxidant activities. Results: Chemical screening reported alkaloids, terpenoids, steroids, and saponins from all investigated sponges. The LC-MS/MS analysis identified various compounds which mainly contained steroids. Antimicrobial activity (against Bacillus subtilis, Escherichia coli, Salmonella enterica, and Candida albicans) was only shown by the Xestospongia sp. extract. Meanwhile, extracts of M. sarasinorum, Xestospongia sp., and Callyspongia sp. exhibited potent radical scavenging activity. Conclusion: The study concluded that the selected sponges could provide various groups of compounds. Methanol extracts of these sponges could be used as sources of antimicrobial and antioxidant agents.


2012 ◽  
Vol 1 (10) ◽  
pp. 79 ◽  
Author(s):  
G. Raja* ◽  
Ivvala Anand Shaker ◽  
Inampudi Sailaja ◽  
R. Swaminathan ◽  
S. Saleem Basha ◽  
...  

Natural antioxidants can protect the human body from free radicals and retard the progress of many chronic diseases as well as lipid oxidative rancidity in foods. The role of antioxidants has protected effect against free radical damage that may cause many diseases including cancer. Primary sources of naturally occurring antioxidants are known as whole grains, fruits, and vegetables. Several studies suggest that regular consumption of nuts, mostly walnuts, may have beneficial effects against oxidative stress mediated diseases such as cardiovascular disease and cancer. The role of antioxidants has attracted much interest with respect to their protective effect against free radical damage that may cause many diseases including cancer. Juglans regia L. (walnut) contains antioxidant compounds, which are thought to contribute to their biological properties. Polyphenols, flavonoids and flavonols concentrations and antioxidant activity of Leaves, Stems and Nuts extract of Juglans regia L. as evaluated using DPPH, ABTS, Nitric acid, hydroxyl and superoxide radical scavenging activity, lipid peroxidation and total oxidation activity were determined. The antioxidant activities of Leaves, Stems and Nuts extract of Juglans regia L. were concentration dependent in different experimental models and it was observed that free radicals were scavenged by the test compounds in all the models.


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