Novel Synthesis of Prenylated Phenols and Their Antioxidant Properties

A novel method for the prenylation of phenols has been developed using 2-methyl-but-3-ene-2-ol as the prenylating agent in the presence of Amberlyst 15. The prenylated catechols and quinols showed better antioxidant activity than the corresponding non-prenylated compounds in the in vitro DPPH and lipid peroxidation assay. The resorcinol derivatives did not show significant antioxidant activity.

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Aqueous Extracts of Teucrium polium Possess Remarkable Antioxidant Activity In Vitro

Evidence-based Complementary and Alternative Medicine ◽

10.1093/ecam/nel028 ◽

2006 ◽

Vol 3 (3) ◽

pp. 329-338 ◽

Cited By ~ 52

Author(s):

Predrag Ljubuncic ◽

Suha Dakwar ◽

Irina Portnaya ◽

Uri Cogan ◽

Hassan Azaizeh ◽

...

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Rat Liver ◽

Antioxidant Properties ◽

Liver Homogenate ◽

Plasma Oxidation ◽

Teucrium Polium ◽

Liver Homogenates ◽

Β Carotene

Teucrium poliumL. (Lamiaceae) (RDC 1117) is a medicinal plant whose species have been used for over 2000 years in traditional medicine due to its diuretic, diaphoretic, tonic, antipyretic, antispasmodic and cholagogic properties. The therapeutic benefit of medicinal plants is often attributed to their antioxidant properties. We previously reported that an aqueous extract of the leaves and stems of this plant could inhibit iron-induced lipid peroxidation in rat liver homogenate at concentrations that were not toxic to cultured hepatic cells. Others have reported that organic extracts of the aerial components of this plant could inhibit oxidative processes. Against this background, we felt further investigation on the antioxidant action of the extract ofT. poliumprepared according to traditional Arab medicine was warranted. Accordingly, we assessed (i) its ability to inhibit (a) oxidation of β-carotene, (b) 2,2′-azobis(2-amidinopropan) dihydrochloride (AAPH)-induced plasma oxidation and (c) iron-induced lipid peroxidation in rat liver homogenates; (ii) to scavenge the superoxide ($${\hbox{ O }}_{2}^{\bullet -}$$) radical and the hydroxyl radical (OH•); (iii) its effects on the enzyme xanthine oxidase activity; (iv) its capacity to bind iron; and (v) its effect on cell glutathione (GSH) homeostasis in cultured Hep G2 cells. We found that the extract (i) inhibited (a) oxidation of β-carotene, (b) AAPH-induced plasma oxidation (c) Fe2+-induced lipid peroxidation in rat liver homogenates (IC50 = 7 ± 2 μg ml−1); (ii) scavenged $${\hbox{ O }}_{2}^{\bullet -}$$(IC50 = 12 ± 3 μg ml−1) and OH• (IC50 = 66 ± 20 μg ml−1); (iii) binds iron (IC50 = 79 ± 17 μg ml−1); and (iv) tended to increase intracellular GSH levels resulting in a decrease in the GSSG/GSH ratio. These results demonstrate that the extract prepared from theT. poliumpossesses antioxidant activityin vitro. Further investigations are needed to verify whether this antioxidant effect occursin vivo.

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Role of transferrin and ceruloplasmin in antioxidant activity of lung epithelial lining fluid

Journal of Applied Physiology ◽

10.1152/jappl.1988.64.5.2092 ◽

1988 ◽

Vol 64 (5) ◽

pp. 2092-2099 ◽

Cited By ~ 45

Author(s):

E. R. Pacht ◽

W. B. Davis

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Serum Proteins ◽

Antioxidant Properties ◽

Epithelial Lining ◽

Epithelial Lining Fluid ◽

Lung Epithelial ◽

Ferroxidase Activity

Lung epithelial lining fluid (ELF) is a thin layer of plasma ultrafiltrate and locally secreted substances that may provide antioxidant protection and serve as a "front-line" defense for the lower respiratory tract epithelium. To characterize the antioxidant properties of ELF, young, healthy, nonsmoking volunteers underwent bronchoalveolar lavage with determination of ELF volumes and ELF proteins. ELF (greater than 0.4 ml) is a potent inhibitor of lipid peroxidation as measured by malondialdehyde (MDA) production in an in vitro iron-dependent assay system. Two serum proteins, transferrin and ceruloplasmin, were quantitated in ELF and found to be potent inhibitors of lipid peroxidation. Other ELF components, including vitamin E, vitamin C, and albumin, did not function as antioxidants in this system. Several experimental observations suggest that ELF transferrin was more important than ceruloplasmin in inhibiting lipid peroxidation: 1) ELF concentrations of transferrin were 20-fold higher than those for ceruloplasmin; 2) ELF antioxidant activity was abolished by preincubation with Fe3+; 3) ELF antioxidant activity was minimally affected by sodium azide, which is known to inhibit ceruloplasmin ferroxidase activity; and 4) ELF ceruloplasmin ferroxidase activity was virtually nondetectable. ELF possesses a significant antioxidant activity that may be important in vivo in protecting the lung from oxidant injury.

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A comparative study of phenolic compound antioxidant activity by the polarography method, using microsomal lipid peroxidation in vitro

Current Issues in Pharmacy and Medical Sciences ◽

10.1515/cipms-2018-0034 ◽

2018 ◽

Vol 31 (4) ◽

pp. 186-189

Author(s):

Anatolii Gordiienko ◽

Mykola Blazheyevskyi ◽

Ivan Iurchenko

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Phenolic Compounds ◽

Chemical Structure ◽

Quantitative Estimation ◽

Antioxidant Properties ◽

Microsomal Lipid Peroxidation ◽

Phenolcarboxylic Acids ◽

Inhibition Ability

Abstract For comparative purposes, a quantitative estimation of antioxidant activity of phenolic compounds of different classes was conducted by way of the polarography method, via the ADP-Fe2+ model of the induced ascorbate-dependent lipid peroxidation of rat liver micro-somes within an in-vitro system. As a result, it was recognized that the antioxidant properties of phenolic compounds depend on the nature and chemical structure of several substances. In respect of such activity, leaders in the classes of investigated polyphenolic compounds are: Propyl gallate = Gallotannin (Phenolcarboxylic acids and their derivatives) > Quercetin = Myricetin (Flavonols) > Luteolin (Flavo n) = Mangiferin (Xanthones) > Kaempferol (Flavonols) = Catechin (Flavans). Thus, the assessment of the inhibition ability of the lipid peroxidation of microsomes by phenolic compounds can be used as an accessible test for the preliminary quantitative estimation of their antioxidant properties.

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Inhibition of Fe2+ Induced Lipid Peroxidation in Rats Brain by Extract of Euphorbia heterophylla in vitro

European Journal of Medicinal Plants ◽

10.9734/ejmp/2019/v27i130103 ◽

2019 ◽

pp. 1-8

Author(s):

Leye Jonathan Babatola ◽

Oluwakemisola B. Oshanimi ◽

Olanrewaju M. Oluba ◽

Lawrence Okoror ◽

Adewale Agboola Odutuga

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Methanol Extract ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Reducing Power ◽

Total Phenol ◽

Dependent Manner ◽

Significant Difference

This study is sought to determine the antioxidant activity and protective ability of aqueous and methanol extractible phytochemicals from Euphorbia heterophylla leaves on lipid peroxidation induced in rat brain by pro-oxidant, in vitro. The extracts of the leaves were prepared, and the ability of the extracts is to inhibit 25 µM FeSO4 induced lipid peroxidation in isolated rats’ brain, were determined. Thereafter, total phenol content, reducing power (FRAP), Fe (II) chelating, and DPPH* free radical scavenging ability of the extracts was determined and considered as an index of antioxidant activity. The results revealed that the extracts inhibit malondialdehyde (MDA) production in the basal and pro-oxidant induced lipid peroxidised rats in a dose-dependent manner, [methanol 80.11%, aqueous 70.3%] with the methanol extract (MEE) significantly (P< 0.05) than that of aqueous extract (AEE). The methanol extract (0.74 ± 0.6 mg/g) had higher total phenol contents than the aqueous (0.57 ± 1.2 mg/g); likewise the methanol extract had higher reducing power (0.08 ± 0.2, 0.03 ± 0.1 mg/g), but had no significant difference in Fe (II) chelating ability (EC50= 0.34, 0.36) with DPPH* scavenging ability (EC50=0.075, 0.075). This antioxidant properties and the protective effect of this leaf could be harnessed in the management and prevention of degenerative diseases in association with oxidative stress.

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Chemical Composition and Antioxidant Properties of Essential Oils from Peppermint, Native Spearmint and Scotch Spearmint

Molecules ◽

10.3390/molecules24152825 ◽

2019 ◽

Vol 24 (15) ◽

pp. 2825 ◽

Cited By ~ 9

Author(s):

Zhaohai Wu ◽

Bie Tan ◽

Yanhong Liu ◽

James Dunn ◽

Patricia Martorell Guerola ◽

...

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Chemical Composition ◽

Essential Oils ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Reducing Power ◽

C Elegans ◽

Reducing Power Assay

Natural antioxidants have drawn growing interest for use in animal feed and the food industry. In the current study, essential oils (EOs) obtained from hydrodistillation of three mentha species, including Mentha piperita (peppermint), Mentha spicata (native spearmint) and Mentha gracilis (Scotch spearmint), harvested in the Midwest region in the United States, were analyzed for their chemical composition using gas chromatography-mass spectrometry, and their antioxidant properties were assessed through chemical assays, in vitro cell culture modeling and in Caenorhabditis elegans (C. elegans). The activity of ferric iron reduction and free-radical scavenging capacity were assessed through chemical-based assays, including the reducing power assay, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, and Trolox equivalent antioxidant capacity assay (TEAC). Subsequently, the capacity of EOs to mitigate lipid peroxidation was analyzed at various doses using fresh liver homogenates from pigs. A porcine jejunum epithelial cell line (IPEC-J2) was employed as in vitro model to study the cellular antioxidant activity of the mint EOs. Finally, the effectiveness of mint EOs to alleviate acute systemic oxidative damage were evaluated in vivo using C. elegans. Data were analyzed by the MIXED procedure of SAS. Contrast statement was performed to assess linear or quadratic effects of mint EOs given at various doses. All three EOs are mostly composed of monoterpenes and their derivatives (76–90%), but differed in the major compounds, which are menthol and menthone (50%) in peppermint EO and carvone (70%) in spearmint EOs. Three mint EOs demonstrated prominent radical scavenging and Fe3+ reducing activity in chemical-based assays. In comparison with native and Scotch spearmint EOs, peppermint EO had the lowest (p < 0.05) half maximal effective concentration (EC50) in DPPH and TEAC assays and higher efficacy in the reducing power assay. All three EOs exhibited equivalent activity in mitigation of chemical-induced lipid peroxidation in liver tissues in a dose-dependent manner (linear, p < 0.001). The maximal cellular antioxidant activity (CAA) was observed at 5 µg/mL for peppermint, and 100 µg/mL for native and Scotch spearmint EOs. The addition of 25 µg/mL of both spearmint EOs increased (p < 0.05) cellular concentrations of glutathione in H2O2-treated IPEC-J2 cells, suggesting enhanced endogenous antioxidant defense. Supplementation of 100 µg/mL of peppermint or Scotch spearmint EO significantly increased (p < 0.05) the survival rate of C. elegans in response to H2O2-induced oxidative stress. The protective effect is comparable to that of supplementation of 10 µg/mL of ascorbic acid. However native spearmint EO failed to reduce the death rate within the same supplementation dose (10–200 μg/mL).

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Antioxidant Activity of Actinodaphne Hookeri Meissn Leaves

Journal of Scientific Research ◽

10.3329/jsr.v1i3.2266 ◽

2009 ◽

Vol 1 (3) ◽

pp. 606-614

Author(s):

D. D. Prajapati ◽

N. Patel ◽

K. Mruthunjaya ◽

R. Savadi

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Antioxidant Capacity ◽

Total Antioxidant Capacity ◽

Antioxidant Properties ◽

Phytochemical Investigation ◽

Experimental Parameters ◽

Total Antioxidant ◽

Treatment Of Diabetes

Leaves of Actinodaphne hookeri (AH) Meissn (family, lauraceae, pisa) are used traditionally in the treatment of diabetes, disorders of the urinary tract which are more common in Chhattisgarh and eastern part of India. It contains flavonoids and quercetin-3-rhamnoside as an important constituent. The leaves were extracted with 70% hydro alcoholic solvent. Preliminary phytochemical investigation showed the presence of triterpenoids, alkaloids, tannins, flavonoids, glycosides and carbohydrates. The antioxidant activity of 70% hydro alcoholic extracts of AH was evaluated in vitro by various experimental parameters such as b-carotene-linoleic acid, lipid peroxidation and total antioxidant capacity. Our results showed that Actinodaphne hookeri leaves displayed potent antioxidant properties, supporting the ethnomedical use given to this plant to treat diabetes and urinary disorder. Keywords: Actinodaphne hookeri; Antioxidant; Lipid peroxidation; Total antioxidant capacity. © 2009 JSR Publications. ISSN: 2070-0237 (Print); 2070-0245 (Online). All rights reserved.DOI: 10.3329/jsr.v1i3.2266 J. Sci. Res. 1 (3), 606-614 (2009)

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Antioxidant Activity of Flavonoids from Sweet Potato Vines In Vitro

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.236-238.2634 ◽

2011 ◽

Vol 236-238 ◽

pp. 2634-2638 ◽

Cited By ~ 2

Author(s):

Ying Chang Li

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Free Radicals ◽

Sweet Potato ◽

Antioxidant Properties ◽

Reducing Power ◽

Superoxide Anions ◽

Ascorbic Acids ◽

Hydroxyl Free Radicals

Flavonoids from Sweet potato vines are often regarded as a functional ingredient to promote nutritional value of food. In this study, the antioxidant activity of flavonoids from Sweet potato vines was evaluated by various methods with ascorbic acid as control standards. The results showed that flavonoids could inhibit lipid peroxidation, increase reducing power, scavenge hydroxyl free radicals, superoxide anions and DPPH radicals. Those antioxidant properties of the flavonoids depended on flavonoids content and increased with increasing of sample content. The flavonoids were better than ascorbic acids on inhibiting lipid peroxidation, but it was weaker than ascorbic acids on reducing power and scavenging hydroxyl free radicals, superoxide anions and DPPH radicals. ID50 (50% inhibiting dose) of inhibiting lipid peroxidation, scavenging hydroxyl free radicals, superoxide anions and DPPH radicals of the flavonoids was 17.48μg, 204.95μg, 139.02μg, 138.35μg separately. Therefore, the flavonoids from sweet potato vines is a kind of natural and effective antioxidant and free radical remover.

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Evaluation of Scavenger Properties of some Flavonoidic Vegetal Extracts Obtained from Crataegus monogyna Jacq.

Key Engineering Materials ◽

10.4028/www.scientific.net/kem.415.41 ◽

2009 ◽

Vol 415 ◽

pp. 41-44

Author(s):

Cornelia Nichita ◽

Georgeta Neagu ◽

Virginia Vulturescu ◽

Lucia Pirvu ◽

Nicoleta Maria Badea ◽

...

Keyword(s):

Lipid Peroxidation ◽

Antioxidant Activity ◽

Ex Vivo ◽

Crataegus Monogyna ◽

Lipid Peroxidation Assay ◽

Parallel Behaviour

The scavenger properties of some flavonoidic vegetal extracts obtained from Crataegus monogyna Jacq have been studied using the chemiluminescence technique and ex vivo lipid peroxidation assay. A correlation between antioxidant activity and phenolic/flavonoidic content was observed for all the seven extracts, and a parallel behaviour with the antioxidant activity determinated by ex vivo lipid peroxidation assay and in vitro chemiluminescence tests was also noted.

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Chemical Composition, In Vitro and In Silico Antioxidant Potential of Melissa officinalis subsp. officinalis Essential Oil

Antioxidants ◽

10.3390/antiox10071081 ◽

2021 ◽

Vol 10 (7) ◽

pp. 1081

Author(s):

Matilda Rădulescu ◽

Călin Jianu ◽

Alexandra Teodora Lukinich-Gruia ◽

Marius Mioc ◽

Alexandra Mioc ◽

...

Keyword(s):

Antioxidant Activity ◽

Chemical Composition ◽

Essential Oil ◽

In Silico ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Inhibitory Effect ◽

Melissa Officinalis ◽

Β Carotene

The investigation aimed to study the in vitro and in silico antioxidant properties of Melissa officinalis subsp. officinalis essential oil (MOEO). The chemical composition of MOEO was determined using GC–MS analysis. Among 36 compounds identified in MOEO, the main were beta-cubebene (27.66%), beta-caryophyllene (27.41%), alpha-cadinene (4.72%), caryophyllene oxide (4.09%), and alpha-cadinol (4.07%), respectively. In vitro antioxidant properties of MOEO have been studied in 2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging, and inhibition of β-carotene bleaching assays. The half-maximal inhibitory concentration (IC50) for the radical scavenging abilities of ABTS and DPPH were 1.225 ± 0.011 μg/mL and 14.015 ± 0.027 μg/mL, respectively, demonstrating good antioxidant activity. Moreover, MOEO exhibited a strong inhibitory effect (94.031 ± 0.082%) in the β-carotene bleaching assay by neutralizing hydroperoxides, responsible for the oxidation of highly unsaturated β-carotene. Furthermore, molecular docking showed that the MOEO components could exert an in vitro antioxidant activity through xanthine oxidoreductase inhibition. The most active structures are minor MOEO components (approximately 6%), among which the highest affinity for the target protein belongs to carvacrol.

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Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

Molecules ◽

10.3390/molecules26123579 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3579

Author(s):

Svetlana A. Popova ◽

Evgenia V. Pavlova ◽

Oksana G. Shevchenko ◽

Irina Yu. Chukicheva ◽

Aleksandr V. Kutchin

Keyword(s):

Antioxidant Activity ◽

Antioxidant Properties ◽

Biological Properties ◽

High Reactivity ◽

Biologically Active ◽

Brain Lipids ◽

Wide Range ◽

Privileged Structure ◽

Vitro Model

The pyrazoline ring is defined as a “privileged structure” in medicinal chemistry. A variety of pharmacological properties of pyrazolines is associated with the nature and position of various substituents, which is especially evident in diarylpyrazolines. Compounds with a chalcone fragment show a wide range of biological properties as well as high reactivity which is primarily due to the presence of an α, β-unsaturated carbonyl system. At the same time, bicyclic monoterpenoids deserve special attention as a source of a key structural block or as one of the pharmacophore components of biologically active molecules. A series of new diarylpyrazoline derivatives based on isobornylchalcones with different substitutes (MeO, Hal, NO2, N(Me)2) was synthesized. Antioxidant properties of the obtained compounds were comparatively evaluated using in vitro model Fe2+/ascorbate-initiated lipid peroxidation in the substrate containing brain lipids of laboratory mice. It was demonstrated that the combination of the electron-donating group in the para-position of ring B and OH-group in the ring A in the structure of chalcone fragment provides significant antioxidant activity of synthesized diarylpyrazoline derivatives.

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