Two New Prenylated Isoflavonoids from Erinacea anthyllis with Antioxidant and Antibacterial Activities

Two new prenylated isoflavonoids, namely Erinasone A and Erinasone B along with 19 known secondary metabolites, including twelve isoflavonoids, three polyphenols, one flavonol, two flavanones and three steroids, were isolated from the whole plant (roots and aerial parts) of Erinacea anthyllis. Structures of all isolated compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, HSQC, TOCSY, HMBC and NOESY), mass spectrometry (ESI-MS), UV-Vis, measurement of optical rotation [α]D and by comparison with the literature data. The total phenolic and flavonoid contents were determined in this study. Furthermore, the antioxidant and antibacterial activities of the EtOAc and n-BuOH extracts of E. anthyllis were evaluated. These extracts exhibited moderate antibacterial and antioxidant activities. Their IC50 values were approximately 0.04 mg/mL ( n-BuOH) and 0.037 mg/mL (EtOAc). Consequently, Erinacea anthyllis is a rich source of polyphenolic compounds particularly isoflavonoids used as chemotaxonomic markers for the subfamily Papilionoideae of the family Fabaceae.

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Phenolic Compounds from An Algerian Endemic Species of Hypochaeris laevigata var. hipponensis and Investigation of Antioxidant Activities

Plants ◽

10.3390/plants9040514 ◽

2020 ◽

Vol 9 (4) ◽

pp. 514 ◽

Cited By ~ 1

Author(s):

Nabila Souilah ◽

Zain Ullah ◽

Hamdi Bendif ◽

Kamel Medjroubi ◽

Tahar Hazmoune ◽

...

Keyword(s):

Phenolic Compounds ◽

Antioxidant Activities ◽

Quinic Acid ◽

Total Phenolic ◽

Antioxidant Action ◽

Endemic Plant ◽

Aerial Parts ◽

Phenolic Constituents ◽

First Time ◽

Phenolic And Flavonoid

Hypochaeris laevigata var. hipponensis (Asteraceae) is an endemic plant from Algeria. In the current study, we analyzed for the first time its chemical composition, especially phenolic constituents of dichloromethane (DCM), ethyl acetate (EA), and n-butanol (BuOH) fractionsof the aerial parts of Hypochaeris laevigata var. hipponensis by liquid chromatography-mass spectrometry (LC-MS/MS). The number of phenolic compounds detected in DCM, EA, and BuOH fractions were found to be 9, 20, and 15, respectively. More specifically, 12 phenolic acids were detected. Among them, quinic acid, chlorogenic acid, and caffeic acid were the most abundant ones. Meanwhile, only seven flavonoids were detected. Among them, rutin, apigetrin, and isoquercitrin were the major ones. We also determined the total phenolic and flavonoid contents, and fraction EA showed the highest values, followed by BuOH, and DCM fractions. Furthermore, the antioxidant action was dictated by five methods and the tested plant fractions demonstrated a noteworthy antioxidant action.

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Characterization of Chemical Compounds and Antioxidant Activity of Centaurea solstitialis sp. schouwii (DC.) Q. et S. (Asteraceae)

Current Bioactive Compounds ◽

10.2174/1573407215666190213125259 ◽

2020 ◽

Vol 16 (5) ◽

pp. 618-626

Author(s):

Lamia Aliouche ◽

Paul Mosset ◽

Francisco León ◽

Ignacio Brouard ◽

Samir Benayache ◽

...

Keyword(s):

Antioxidant Activity ◽

Secondary Metabolites ◽

Ethyl Acetate ◽

Sesquiterpene Lactone ◽

Antioxidant Activities ◽

Centaurea Solstitialis ◽

Total Phenolic ◽

Butanol Extract ◽

Aerial Parts ◽

Phenolic And Flavonoid

Background: The antioxidant activity and the total phenolic and flavonoid contents of the derived extracts (chloroform, ethyl acetate and n-butanol) of the 70% hydroalcoholic extract of the aerial parts of Centaurea solstitialis growing in Algeria was assessed. The active extracts were selected for phytochemical investigations. Methods: The antioxidant capabilities of the extracts were assessed using 1, 1-diphenyl-2- picrylhydrazyl radical (DPPH•) scavenging and Cupric Ion Reducing Antioxidant Capacity (CUPRAC) assays. Butylhydroxyanisole (BHA), butylhydroxytoluene (BHT) and α –tocopherol were used as positive controls. The total phenolic content and total flavonoid content of the extracts were determined as gallic acid equivalents and quercetin equivalents, respectively. Chromatographic methods were used to isolate the secondary metabolites and spectrometric and spectroscopic methods were used to determine their chemical structures. Results: The ethyl acetate extract exhibited the highest antioxidant activities followed by the n-butanol extract. The highest phenolic and flavonoid contents were found in the n-butanol extract. Phytochemical study of the ethyl acetate and n-butanol extracts led to the isolation of an undescribed guaianolide named 3-(4-hydroxybenzoyl)-cynaratriol and a known sesquiterpene lactone along with three known flavonoid glycosides. Their structures were established by spectral analyzes mainly high resolution electrospray ionisation mass spectrometry (HR-ESIMS) and 1D and 2D nuclear magnetic resonance experiments. Conclusion: The extracts of aerial parts of C. solstitialis showed significant antioxidant activities. An undescribed sesquiterpene lactone and four known secondary metabolites were isolated from the most active extracts.

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Chemical composition and antioxidant activity of Astragalus monspessulanus L. growing in semiarid areas of Algeria

Journal of the Serbian Chemical Society ◽

10.2298/jsc161212085b ◽

2018 ◽

Vol 83 (1) ◽

pp. 31-38 ◽

Cited By ~ 3

Author(s):

Sawsen Bourezzane ◽

Hamada Haba ◽

Christophe Long ◽

Mohammed Benkhaled

Keyword(s):

Antioxidant Activity ◽

Antioxidant Activities ◽

Optical Rotation ◽

Radical Scavenging ◽

2D Nmr ◽

Test Method ◽

Phytochemical Study ◽

Butanol Extract ◽

Aerial Parts ◽

Nmr Techniques

This paper reports a phytochemical study of the aerial parts of Astragalus monspessulanus L. growing in Algeria. It deals with the isolation and structure elucidation of 13 known compounds. From the n-butanol extract, seven flavonoids 1?7, two saponins and one lignan were isolated. In addition, two phytosterols and one triterpenoid were isolated from the ethyl acetate extract. The structures of all the isolated products were determined by using 1D and 2D-NMR techniques, measurement of optical rotation, mass spectrometry ESI-MS and by comparison with literature data. Furthermore, the antioxidant activity of the n-butanol extract of the aerial parts of Astragalus monspessulanus L. was investigated using the DPPH radical scavenging and ferrous ion chelating assays. The n-butanol extract showed low (EC50 = 2.09?0.434 mg mL-1) to moderate (IC50 = 63.60?0.01 ?g mL-1) antioxidant activities depending on the test method.

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Antioxidant, Antimicrobial, and Free Radical Scavenging Potential of Aerial Parts of Periploca aphylla and Ricinus communis

ISRN Pharmacology ◽

10.5402/2012/563267 ◽

2012 ◽

Vol 2012 ◽

pp. 1-6 ◽

Cited By ~ 14

Author(s):

Jamshed Iqbal ◽

Sumera Zaib ◽

Umar Farooq ◽

Afsar Khan ◽

Irum Bibi ◽

...

Keyword(s):

Antioxidant Activities ◽

Ricinus Communis ◽

Radical Scavenging ◽

Antibacterial Activities ◽

Total Phenolic ◽

Dilution Method ◽

Standard Drug ◽

Phenolic Contents ◽

Aerial Parts

Context. Many diseases are associated with oxidative stress caused by free radicals. Objective. The present study evaluated the in vitro antioxidant and antibacterial activities of various extracts of aerial parts of Periploca aphylla and Ricinus communis. Materials and Methods. In vitro antioxidant activities of the plant extract were determined by DPPH and NO scavenging method. Superoxide anion radical activity was measured by the reduction of nitro blue tetrazolium as compared with standard antioxidants. Total phenolic contents and antibacterial activities of these plants were determined by gallic acid equivalent (GAE) and serial tube dilution method, respectively. Results. Plants showed significant radical scavenging activity. The results were expressed as IC50. n-Propyl gallate and 3-t-butyl-4-hydroxyanisole were used as standards for antioxidant assay. All the extracts of both plants showed comparable IC50 to those of standards. Plants extract exhibited high phenolic contents and antibacterial activities were comparable with standard drug, Ciprofloxacin. Discussion and Conclusion. The present study provides evidence that Periploca aphylla and Ricinus communis prove to be potent natural antioxidants and could replace synthetic antioxidants. Plants can also be used against pathogenic bacterial strains.

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Nutritional Composition,α-Glucosidase Inhibitory and Antioxidant Activities ofOphiopogon japonicusTubers

Journal of Chemistry ◽

10.1155/2015/893074 ◽

2015 ◽

Vol 2015 ◽

pp. 1-7

Author(s):

Yancui Wang ◽

Feng Liu ◽

Zongsuo Liang

Keyword(s):

Amino Acids ◽

Methanol Extract ◽

Antioxidant Activities ◽

Nutritional Composition ◽

Total Phenolic ◽

Ophiopogon Japonicus ◽

Nutritional Compounds ◽

Chloroform Methanol ◽

Phenolic And Flavonoid

Ophiopogon japonicustubers have been widely used as food and traditional Chinese medicine in China. However, their nutritional composition has not been fully reported yet. This study aimed to analyze the nutritional composition ofO. japonicustubers. Theα-glucosidase inhibitory and antioxidant activities of the extracts obtained fromO. japonicustubers were also evaluated byin vitroassays. The results indicated thatO. japonicustubers are rich in carbohydrates, proteins, minerals, and amino acids. Among four extracts, the n-butanol fraction (nBF) and chloroform/methanol extract (CME) ofO. japonicustubers had high amounts of total phenolic and flavonoid contents and exhibited goodα-glucosidase inhibitory and antioxidant activities. Theα-glucosidase inhibition of nBF was higher than acarbose. Overall,O. japonicustubers are full of nutritional compounds and have goodα-glucosidase inhibitory and antioxidant activities.

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Establishing Relationship between Vitamins, Total Phenolic and Total Flavonoid Content and Antioxidant Activities in Various Honey Types

Molecules ◽

10.3390/molecules26154399 ◽

2021 ◽

Vol 26 (15) ◽

pp. 4399

Author(s):

Norhasnida Zawawi ◽

Pei Juin Chong ◽

Nurul Nadhirah Mohd Tom ◽

Nurkhairina Solehah Saiful Anuar ◽

Salma Malihah Mohammad ◽

...

Keyword(s):

Antioxidant Capacity ◽

Phenolic Acids ◽

Antioxidant Activities ◽

Natural Antioxidants ◽

Total Phenolic ◽

Flavonoid Content ◽

Extrinsic Factors ◽

Biochemical Compounds ◽

Phenolic And Flavonoid

Honey is a well-known natural sweetener and is rich in natural antioxidants that prevent the occurrence of oxidative stress, which is responsible for many human diseases. Some of the biochemical compounds in honey that contribute to this property are vitamins and phenolic compounds such as phenolic acids and flavonoids. However, the extent to which these molecules contribute towards the antioxidant capacity in vitro is inconsistently reported, especially with the different analytical methods used, as well as other extrinsic factors that influence these molecules’ availability. Therefore, by reviewing recently published works correlating the vitamin, total phenolic, and flavonoid content in honey with its antioxidant activities in vitro, this paper will establish a relationship between these parameters. Based on the literature, vitamins do not contribute to honey’s antioxidant capacity; however, the content of phenolic acids and flavonoids has an impact on honey’s antioxidant activity.

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ANTIMICROBIAL AND ANTIOXIDANT ACTIVITIES OF SELECTED PLANTS USED BY POPULATIONS FROM JURUENA VALLEY, LEGAL AMAZON, BRAZIL

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i5.17086 ◽

2017 ◽

Vol 9 (5) ◽

pp. 179

Author(s):

Larissa Irene Da Silva ◽

Arunachalam Karuppusamy ◽

Fabio Miyajima ◽

Ivana Maria Povoa Violante ◽

Isanete Geraldini Costa Bieski ◽

...

Keyword(s):

Antioxidant Activities ◽

Shigella Flexneri ◽

Antibacterial Activities ◽

Total Phenolic ◽

Moderate Activity ◽

Cedrela Odorata ◽

Frap Assay ◽

Antioxidant Power ◽

Mato Grosso

Objective: The purpose of this study was to evaluate selected Brazilian plants from Juruena valley region of Mato Grosso, for their in vitro antimicrobial and antioxidant activities.Methods: The powder obtained from different parts of the twenty-six (26) plants were macerated in hydroethanolic solution to obtain the extracts. The hydroethanolic extracts were tested for their in vitro antimicrobial activity by determining the MIC using broth microdilution. The 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical, ferric reducing antioxidant power (FRAP) and nitric oxide (NO) methods were used for the determination of antioxidant activities. Correlation between classes of secondary metabolites and antioxidant activity was assessed.Results: Phanera glabra extract (HEPg) showed broad antibacterial spectrum, presenting the best activity against Klebsiella pneumoniae. Hevea microphylla extract (HEHm) presented a narrow spectrum of antibacterial activity with strong effect against Shigella flexneri. The only plant with broad spectrum antifungal activity was Bertholletia excelsa (HEBe), with moderate activity against strains of Aspergillus and Candida. The following extracts were prominent regarding their activities in the DPPH and FRAP assays-HEBe, Cariniana rubra (HECr) and in the FRAP assay alone, Cedrela odorata (HECo) and HEPg. None of the extracts was active in the NO assay. A significant association was observed between DPPH activity and the total phenolic contents.Conclusion: Our results justified the use of some of the investigated plants in the Brazilian ethnomedicine. The antibacterial activities of these plants are bacteriostatic in nature. These findings support that a number of investigated plants could be a valuable source of new antioxidant and antimicrobial compounds that can potentially deliver novel mechanisms of actions.However, further studies are required.

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NEW FLAVONOIDS FROM THE AERIAL PARTS OF POLYGONUM EQUISETIFORME SM (POLYGONACEAE)

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.15593 ◽

2017 ◽

Vol 9 (2) ◽

pp. 166 ◽

Cited By ~ 2

Author(s):

Sayed A. El-toumy ◽

Joslin Y. Salib ◽

Nabila H. Shafik ◽

Asmaa S. Abd Elkarim ◽

Gihan A. Mick

Keyword(s):

Antioxidant Activity ◽

Methyl Ester ◽

Secondary Metabolites ◽

Gallic Acid ◽

Total Phenolic ◽

Flavonoid Content ◽

Isolation And Identification ◽

Aerial Parts ◽

Dpph Method ◽

Phenolic And Flavonoid

Objective: The current study was to deal the isolation and identification of secondary metabolites from Polygonum equisetiforme and evaluation of antioxidant activity of its extract.Methods: The methanol-water extract (7:3) of the air-dried aerial parts of Polygonum equisetiforme was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of these compounds were elucidated by UV and 1D⁄2D H⁄ C NMR spectroscopy and compared with the literature data. The crude extract was evaluated for in vitro antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method.Results: Ten secondary metabolites were isolated from Polygonum equisetiforme in this study. Of which three new flavonoids named as 3,5,7,2’,5’ pentahydroxyflavone 3-O-b-D-glucopyranoside (1), 3,5,7,2’,5’ pentahydroxyflavone 3-O-b-D-glucopyranoside 8 C-sulphated (2) and quercetin 3-O-β-D-glucucorinde 6''-methyl ester 8-sulphated (3) as well as quercetin 3-O-β-D-glucucorinde methyl ester (4), quercetin 3-O-β-D-glucopyranoside (5), quercetin 7-O-β-D-glucopyranoside (6), quercetin(7), myricetin (8), P-methoxy gallic acid methyl ester (9) and gallic acid (10). The antioxidant potential of P. equisetiforme extract was evaluated by investigating it's total phenolic and flavonoid content and DPPH radical scavenging activity whereby the extract showed significant antioxidant activity (IC50 = 37.45 μg/ml). The total phenolic and flavonoid content was found to be 130.79±5.502 and 45.8±1.63 μg/ml, respectively.Conclusion: Polygonum equisetiforme is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as an antioxidant drug.

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Application of Heating on the Antioxidant and Antibacterial Properties of Malaysian and Australian Stingless Bee Honey

Antibiotics ◽

10.3390/antibiotics10111365 ◽

2021 ◽

Vol 10 (11) ◽

pp. 1365

Author(s):

Nurul Ainaa Farhanah Mat Ramlan ◽

Aina Syahirah Md Zin ◽

Nur Fatihah Safari ◽

Kim Wei Chan ◽

Norhasnida Zawawi

Keyword(s):

Heat Treatment ◽

Antioxidant Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Antibacterial Properties ◽

Antibacterial Activities ◽

Heat Treatments ◽

Stingless Bee ◽

Total Phenolic ◽

Antioxidant Power

In the honey industry, heat treatments are usually applied to maintain honey’s quality and shelf life. Heat treatment is used to avoid crystallisation and allow the easy use of honey, but treatment with heat might affect the antioxidant and antibacterial activities, which are the immediate health effects of honey. This study will determine the effect of heat treatment on Malaysian and Australian stingless bee honey (SBH) produced by the common bee species in both countries. Eighteen honey samples were subjected to heat at 45 °C, 55 °C and 65 °C for one hour and subsequently analysed for their total phenolic content (TPC), total flavonoid content (TFC), DPPH radical scavenging activity, ferric reducing antioxidant power (FRAP) and minimum inhibitory concentration (MIC). The results show that all samples had high TPC, TFC and antioxidant activities before the treatment. The heat treatments did not affect (p < 0.05) the TPC, TFC and antioxidant activities in most samples, but did inhibit the antibacterial activities consistently in most of the samples, regardless of the bee species and country of origin. This study also confirms a strong correlation between TPC and TFC with FRAP activities for the non-heated and heated honey samples (p < 0.05). Other heat-sensitive bioactive compounds in SBH should be measured to control the antibacterial properties present.

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