Selina-1,3,7(11)-trien-8-one and Oxidoselina-1,3,7(11)-trien-8-one from Eugenia uniflora Leaf Essential Oil and Their Cytotoxic Effects on Human Cell Lines

The sesquiterpenes selina-1,3,7(11)-trien-8-one and oxidoselina-1,3,7(11)-trien-8-one were isolated from the essential oil of Eugenia uniflora L. leaves. The structures were elucidated using spectrometric methods (UV, GC–MS, NMR, and specific optical rotation). The relationship between antioxidant activity, as determined by DPPH assay, and the cytotoxic effect was evaluated using tumor cells, namely lung adenocarcinoma epithelial cells (A549) and human hepatoma carcinoma cells (HepG2), as well as a model of normal human lung fibroblast cells (IMR90). Both compounds did not show prominent free-radical scavenging activity according to DPPH assay, and did not inhibit lipid peroxidation in Wistar rat brain homogenate. The isolated compounds showed pro-oxidative effects and cytotoxicity in relation to the IMR90 cell line.

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Chemo-typing of Three Egyptian Rosemary Oil for Their Chemical Composition and Anti-oxidant Activity

Journal of Pharmaceutical Research International ◽

10.9734/jpri/2020/v32i330409 ◽

2020 ◽

pp. 9-14

Author(s):

Menna I. Elshorbagy ◽

Marwa Elsbaey ◽

Hany N. Baraka ◽

Mohamed Farid Lahloub

Keyword(s):

Antioxidant Activity ◽

Chemical Composition ◽

Essential Oil ◽

Essential Oils ◽

Radical Scavenging Activity ◽

Standard Procedure ◽

Radical Scavenging ◽

Volatile Oil ◽

Fused Silica ◽

Dpph Assay

Aims: To study the chemical composition of volatile oil samples from different place in Egypt (Mansoura, Gamsa and Assuit) and study their antioxidant activity determined by DPPH assay. Study Design: Hydro distillation of volatile oil samples and their GC/MS analysis and determination of their antioxidant activity by DPPH assay. Place and Duration of Study: Department of Pharmacognosy, Faculty of pharmacy, Mansoura university, Egypt, between June 2015 and November 2017. Methodology: The essential oil was isolated by hydro-distillation for 5 h using a Clevenger-type all-glass apparatus according to the standard procedure of the European pharmacopeia and volatile oils analysis was performed by GC and GC-MS. GC analysis was carried out using Focus-DSQ-ӀI GC/MS instrument (Thermo Scientific, MA, USA) equipped with TR-5 fused silica column (30 m × 0.25 mm, film thickness 0.25 µm). Results: The yield of the essential oils of three rosemary plants growing in Mansoura (RM), Gamsa (RG) and Assiut (RA) were 0.20% v/w, 0.32% v/w and 0.24% v/w, respectively. Their chemical composition was analyzed by GC/MS, RM and RG were found to be α-pinene dominated chemotypes, 32.4% and 29.6%, respectively, meanwhile RA was camphor dominated chemotype (17.2%). Furthermore, their antioxidant activity was determined by DPPH assay. Their IC50 values of essential oils of RM, RG and RA were 8.66 ± 0.7, 8.18 ± 0.5 and 9.74 ± 0.2, respectively. Conclusion: The GC/MS spectral data revealed the considerable difference between the chemical composition of essential oil constituents of RM, RG and RA which lead to different chemotypes. The present results also demonstrate that REO obtained from different areas in Egypt exhibited free radical scavenging activity determined by DPPH assay due to the synergistic effect between their constituents.

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The chemical composition, antimicrobial and antiradical properties of the essential oil of Achillea grandifolia aerial parts from Serbia

Botanica Serbica ◽

10.2298/botserb2102233d ◽

2021 ◽

Vol 45 (2) ◽

pp. 233-240

Author(s):

Milica Drobac ◽

Jelena Kukic-Markovic ◽

Marina Milenkovic ◽

Marjan Niketic ◽

Silvana Petrovic

Keyword(s):

Antimicrobial Activity ◽

Essential Oil ◽

Micrococcus Luteus ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Aromatic Plants ◽

Bacterial Strains ◽

Dpph Assay ◽

Light Yellow ◽

Aerial Parts

Aromatic plants and essential oils have many applications in medicine, pharmaceuticals, cosmetics, and the food industry. The essential oil of the flowering aerial parts of Achillea grandifolia, obtained by hydrodistillation, was analyzed for its constituents and investigated for antimicrobial and radical scavenging activity. The essential oil was characterized by a high amount of oxygenated monoterpenes (72.7%) with 1,8-cineole (29.2%) and camphor (23.4%) being the most abundant. Sesquiterpenes were present in smaller quantities (4.8%). Antimicrobial activity was tested against eight ATCC bacterial strains and two ATCC strains of Candida albicans. The essential oil exhibited highly pronounced antimicrobial activity against Micrococcus luteus with a MIC value of 3.50 ?g/mL, as well as significant antimicrobial activity (<100 ?g/mL) against Staphylococcus aureus, S. epidermidis and Bacillus subtilis. Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa were resistant. Achillea grandifolia essential oil exhibited concentration-dependent antiradical activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical with an SC50 value of 5.4 mg/mL. The TLC-DPPH assay revealed two main light yellow spots indicating components with anti-DPPH activity, which after isolation were identified as 1,8-cineole and camphor.

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Chemical variability and antioxidant activities of the essential oils of the aerial parts of Ammoides verticillata and the roots of Carthamus caeruleus and their synergistic effect in combination

Combinatorial Chemistry & High Throughput Screening ◽

10.2174/1386207323666200606213057 ◽

2020 ◽

Vol 23 ◽

Author(s):

Imane Rihab Mami ◽

Noria Merad-Boussalah ◽

Mohammed El Amine Dib ◽

Boufeldja Tabti ◽

Jean Costa ◽

...

Keyword(s):

Essential Oil ◽

Essential Oils ◽

Antioxidant Activities ◽

Radical Scavenging Activity ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Natural Food ◽

Chemical Compositions ◽

Chemical Variability ◽

Ammoides Verticillata

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.

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Synthesis, Characterization, Antimicrobial and Antioxidant Potential of Diazenyl Chalcones

Current Topics in Medicinal Chemistry ◽

10.2174/1568026618666180626095714 ◽

2018 ◽

Vol 18 (10) ◽

pp. 844-856 ◽

Cited By ~ 5

Author(s):

Harmeet Kaur ◽

Balasubramanian Narasimhan

Keyword(s):

Radical Scavenging Activity ◽

Radical Scavenging ◽

Antioxidant Potential ◽

Dilution Method ◽

Dpph Assay ◽

Antimicrobial Potential ◽

Structural Conformation ◽

Uv Visible ◽

Tube Dilution Method

A series of diazenyl chalcones was prepared by base catalyzed Claisen-Schmidt condensation of synthesized hydroxy substituted acetophenone azo dye with various substituted aromatic/ heteroaromatic aldehydes. The structural conformation of synthesized chalcones was done by a number of physicochemical and spectral means like FTIR, UV-visible, mass, NMR spectroscopy and CHNS/O analysis. These diazenyl chalcones were assessed for their in vitro antimicrobial potential against several Gram-negative, Gram-positive bacterial and fungal strains by serial tube dilution method. The fluconazole and cefadroxil were used as standard drugs. The target compounds were also evaluated for their antioxidant potential by DPPH assay. (2E)-3-(2,4-Dichlorophenyl)-1-(4-((2,6- dihydroxyphenyl)diazenyl)phenyl)prop-2-en-1-one (C-7) had shown very good antimicrobial potential with MIC ranges from 3.79 to 15.76 μg/ml against most of the tested microorganisms. Most of the synthesized diazenyl chalcones were found to be active against B. subtilis. The (2E)-1-(5-((2-Chloro- 4-nitrophenyl)diazenyl)-2-hydroxyphenyl)-3-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one (C-10) had shown high free radical-scavenging activity when compared with the ascorbic acid as the reference antioxidant.

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Chemical Composition, Antibacterial, Insecticidal and Anti-Oxidant Activities of Three Acantholimon Species (A. atropatanum, A. gilliatii and A. tragacanthium)

The Natural Products Journal ◽

10.2174/2210315509666190117153456 ◽

2020 ◽

Vol 10 (3) ◽

pp. 272-278

Author(s):

Ardalan Pasdaran ◽

Satyajit D. Sarker ◽

Lutfun Nahar ◽

Azadeh Hamedi

Keyword(s):

Antibacterial Activity ◽

Chemical Composition ◽

Essential Oil ◽

Essential Oils ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Main Compound ◽

Aerial Parts ◽

Anti Oxidant ◽

Gas Chromatography Mass Spectroscopy

Background: The essential oil from the Acantholimon genus have been an integral part of the traditional food additive in Middle East. Most of the plants in Acantholimon genus have not been studied scientifically. The aim of this study is to investigate the chemical composition, antibacterial, insecticidal and anti-oxidant activities of three Acantholimon species including Acantholimon atropatanum, A. gilliatii and A. tragacanthium. Method: The essential oils of the aerial parts were extracted by hydrodistillation. Chemical constitutions were identified by gas chromatography- mass spectroscopy technique, also their toxicities were assessed against the two important grain products pests, Oryzeaphilus mercator and Tribolium castaneum. Antibacterial activity was assessed against the three foodborne bacteria that include Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus based on the disc diffusion assay. Free-radical-scavenging property was identified based on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity. Results: 2-hexahydrofarnesyl acetone was the main compound in A. gilliatii and A. tragacanthium, whilst farnesyl acetone, heptacosane and germacrene D were the principal components of A. atropatanum essential oil. These oils exhibited 40-90% mortality of O. mercator and/or T. castaneum at a dose of 12 μl/l air after 48h of exposure, and exhibited significant free-radicalscavenging property (RC50 = 3.7 × 10-3 - 8.3 × 10-3 mg/ml). The oils of A. tragacanthium and A. gilliatii showed a weaker antibacterial activity compared to A. atropatanum. Conclusion: A. atropatanum, A. gilliatii and A. tragacanthium essential oils had significant insecticidal and anti-oxidant properties. They also showed week to moderate antibacterial activity against P. aeruginosa and S. aureus.

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Biological Activities of Carlina Oxide Isolated from the Roots of Carthamus caeruleus

The Natural Products Journal ◽

10.2174/2210315509666190117152740 ◽

2020 ◽

Vol 10 (2) ◽

pp. 145-152 ◽

Cited By ~ 1

Author(s):

Imane Rihab Mami ◽

Rania Belabbes ◽

Mohammed El Amine Dib ◽

Boufeldja Tabti ◽

Jean Costa ◽

...

Keyword(s):

Antifungal Activity ◽

Essential Oil ◽

Skin Diseases ◽

Antioxidant Activities ◽

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Penicillium Expansum ◽

Natural Food ◽

Antioxidant Power

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.

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Suggestions on the Contribution of Methyl Eugenol and Eugenol to Bay Laurel (Laurus nobilis L.) Essential Oil Preservative Activity through Radical Scavenging

Molecules ◽

10.3390/molecules26082342 ◽

2021 ◽

Vol 26 (8) ◽

pp. 2342

Author(s):

Nikolaos Nenadis ◽

Maria Papapostolou ◽

Maria Z. Tsimidou

Keyword(s):

Essential Oil ◽

Radical Scavenging Activity ◽

Pearson Correlation ◽

Radical Scavenging ◽

Methyl Eugenol ◽

Partial Least Square ◽

Least Square ◽

Partial Least Square Regression ◽

Positive Contribution ◽

Scavenging Activity

The present study examined the radical scavenging potential of the two benzene derivatives found in the bay laurel essential oil (EO), namely methyl eugenol (MEug) and eugenol (Eug), theoretically and experimentally to make suggestions on their contribution to the EO preservative activity through such a mechanism. Calculation of appropriate molecular indices widely used to characterize chain-breaking antioxidants was carried out in the gas and liquid phases (n-hexane, n-octanol, methanol, water). Experimental evidence was based on the DPPH• scavenging assay applied to pure compounds and a set of bay laurel EOs chemically characterized with GC-MS/FID. Theoretical calculations suggested that the preservative properties of both compounds could be exerted through a radical scavenging mechanism via hydrogen atom donation. Eug was predicted to be of superior efficiency in line with experimental findings. Pearson correlation and partial least square regression analyses of the EO antioxidant activity values vs. % composition of individual volatiles indicated the positive contribution of both compounds to the radical scavenging activity of bay laurel EOs. Eug, despite its low content in bay laurel EOs, was found to influence the most the radical scavenging activity of the latter.

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Composition and biological assays of the leaf essential oil of Asparagus flagellaris (Kunth) Bak

Clinical Phytoscience ◽

10.1186/s40816-020-00245-1 ◽

2021 ◽

Vol 7 (1) ◽

Author(s):

Oluwakayode O. Odeja ◽

Michael Gabriel Ibok ◽

Ejike O. Okpala

Keyword(s):

Free Radical ◽

Essential Oil ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Salmonella Typhi ◽

Antimicrobial Activities ◽

Free Radical Scavenging ◽

Gas Chromatography Mass Spectrometry ◽

Klebsiella Pneumonia ◽

Leaf Essential Oil

Abstract Background Asparagus flagellaris leaves are ethnomedicinally used to treat syphilis, gonorrhea and other sexually transmitted diseases (STDs), with no reports on the volatile constituents. This study was aimed to quantitatively and qualitatively characterise the composition of essential oil, evaluates the free radical scavenging and antimicrobial capacity of the essential oil. Methods The essential oil was isolated by hydrodistillation method using all-glass Clevenger-type apparatus, while the identification and quantification of constituents were performed by gas chromatography-mass spectrometry (GC-MS) technique. The antioxidant activity on 2, 2-diphenyl-1-picrylhydrazyl (DPPH) was evaluated and the oil was also tested against 10 strains of microorganisms consisting of 6 bacteria: Escherichia coli, Salmonella typhi, Klebsiella pneumonia, Pseudomonas aeruginosa, Staphylococcus aureus and Bacillus subtilis and 4 fungi: Candida albicans, Penicillium notatum, Aspergillus niger and Rhizopus spp. using broth dilution and surface plate methods, respectively. Results A pale yellow essential oil with a characteristic scent was obtained, with a yield of 0.80% (w/w). A total of 28 compounds accounting for 97.41% of the total oil contents were identified. The oil was predominated by Thymol and its derivatives, accounting for 57.48%. The most abundance (% area) constituents of the essential oil were 5-Thymyl tiglate (18.49%), Thymyl-2-methyl butyrate (17.34%), Thymol hydroquinone dimethyl ether (10.52%), Thymol methyl ether (9.42%) and 5-Propyl-1, 3-benzodioxole (4.59%). The essential oil showed a significant free radical scavenging activity compared to the standard antioxidant drugs used in this study, with % inhibition varying from 88.06 ± 0.0001 to 93.05 ± 0.0006. The leaf essential oil exhibited antimicrobial activity on all the tested organisms at 500–125 μg/mL, with an 18–10 mm inhibitory zone. Conclusion The leaf essential oil of A. flagellaris contains notable chemical compounds responsible for its antioxidant and antimicrobial activities.

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Diversity and honey properties of stingless bees from meliponiculture in East and North Kalimantan, Indonesia

Biodiversitas Journal of Biological Diversity ◽

10.13057/biodiv/d211021 ◽

2020 ◽

Vol 21 (10) ◽

Author(s):

SYAFRIZAL ◽

RICO RAMADHAN ◽

IRAWAN WIJAYA KUSUMA ◽

SAAT EGRA ◽

KUNIYOSHI SHIMIZU ◽

...

Keyword(s):

Stingless Bees ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Stingless Bee ◽

Phytochemical Screening ◽

Radical Scavengers ◽

Tropical Rain Forests ◽

Dpph Assay ◽

Research Areas ◽

Light Yellow

Abstract. Syafrizal, Ramadhan R, Kusuma IW, Egra S, Shimizu K, Kanzaki M, Arung ET. 2020. Diversity and honey properties of stingless bees from meliponiculture in East and North Kalimantan, Indonesia. Biodiversitas 21: 4623-4630. Kalimantan Island in Indonesia is covered by tropical rain forests that are rich in biodiversity. Species, include a stingless bee (Trigona spp.). Recently, stingless bee beekeeping (Meliponiculture) in this region has become popular because the honey has a unique taste, a mix of sweet, sour, and bitter which is highly valued. The objective of this study was to determine the diversity of stingless bee species, the number of colonies, type of hive, and honey properties such as taste, acidity, color, phytochemicals, and radical scavenging activity or antioxidant in meliponiculture in selected areas of Eastern and Northern Kalimantan, Indonesia. The area studied included Samarinda, Balikpapan, Penajam, Bontang, Sangatta, and Tarakan. The study conducted by visiting the farmers, collecting the stingless bees species and bee products (honey, propolis, and bee pollen), pH, color and taste determination, phytochemical screening, and DPPH assay. We found 12 species, with Heterotrigona itama and Tetragonula laeviceps being the main ones cultivated by people in all research areas, except Balikpapan. We counted 111 colonies of T. laeviceps and 99 of H. itama in the meliponiculture. There were three types of hive used by farmers in meliponiculture. Most of the honey tasted sweet and sour with acidity or pH ranging from 3-4, and color from dark brown to light yellow. The phytochemicals contained tannin, alkaloid, flavonoid, triterpenoid, carotenoid, coumarin, saponin, and carbohydrate. The Tetragonula sarawakensis honey was the most potent in term radical scavengers. Our findings showed that stingless bee honey contains antioxidants with phytochemicals that are very useful for human health.

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Radical scavenging and antimicrobial activity of essential oil and extracts of Echinophora sibthorpiana Guss. from Macedonia

Archives of Biological Sciences ◽

10.2298/abs1401401m ◽

2014 ◽

Vol 66 (1) ◽

pp. 401-413 ◽

Cited By ~ 7

Author(s):

Ksenija Mileski ◽

Ana Dzamic ◽

Ana Ciric ◽

Slavica Grujic ◽

M. Ristic ◽

...

Keyword(s):

Essential Oil ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Antimicrobial Properties ◽

Ethanol Extract ◽

Antimicrobial Effect ◽

Total Phenolic ◽

Scavenging Activity ◽

Aerial Parts ◽

Positive Controls

This study was undertaken to determine the antioxidant and antimicrobial effect of essential oil and extracts of Echinophora sibthorpiana Guss. (fam. Apiaceae) collected in Macedonia. The chemical composition of E. sibthorpiana essential oil was characterized by the presence of methyl eugenol (60.40%), p-cymene (11.18%) and ?-phellandrene (10.23%). The free radical scavenging activity of extracts and essential oil was evaluated by DPPH and ABTS assays. The aqueous extract of aerial parts exhibited the strongest scavenging activity (IC50=1.67 mg/ml); results of the ABTS test showed that the most effective was the ethanol extract of aerial parts (1.11 mg vit. C/g). The essential oil showed stronger antioxidant activity compared to hydroxyanisole, ascorbic acid and quercetin that were used in the DPPH and ABTS tests, respectively. The total phenolic and flavonoid concentrations in the extracts ranged between 38.65-60.72 mg GA/g, and 3.15-19.00 mg Qu/g, respectively. The antimicrobial properties of the extracts and essential oil were investigated using a micro-well dilution technique against human pathogenic strains. The results were comparable with the effects of the positive controls, streptomycin and fluconazole. These findings indicate that E. sibthorpiana extracts and oil can be used in preventive treatments and as an alternative for synthetic preservatives.

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