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      Chemical constituents of Phragmanthera austroarabica A. G. Mill and J. A. Nyberg with potent antioxidant activity

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          Abstract

          Background:

          Phragmanthera austroarabica A.G. Mill. and J. A. Nyberg is a semi parasitic plant belonging to family Loranthaceae. It was collected from Saudi Arabia. It is widely used in folk medicine among the kingdom in treatment of various diseases including diabetes mellitus.

          Objective:

          The total alcoholic extract of P. austroarabica collected from Saudi Arabia was investigated for the chemical structure and prominent biological activity of the main constituents.

          Materials and Methods:

          Isolation of the active constituents was performed using different chromatographic techniques including column chromatography packed with silica or sephadex and preparative thin layer chromatography. The structures of the isolated compounds were established based on different spectroscopic data as mass spectrum, one-dimensional and two-dimensional nuclear magnetic resonance (correlation spectroscopy, heteronuclear single quantum coherence, and heteronuclear multiple-bond correlation).

          Results:

          Phytochemical investigation of the plant resulted in isolation of 12 compounds. The isolated compounds were identified as chrysophanic acid, emodin, chrysophanic acid-8- O-glucoside, emodin-8- O-glucoside, pectolinarigenin, quercetin, dillenetin-3- O-glucoside, catechin, catechin-4’- O-gallate, methyl gallate, lupeol and ursolic acid. All the isolated phenolic compounds revealed significant free radical scavenging activities when tested using 2,2-diphenyl-1-picrylhydrazyl reagent.

          Conclusion:

          The antioxidant activities of the isolated compounds can justify the use of P. austroarabica in traditional medicine for treatment of diabetes and verify its possible application as an antihyperglycemic drug.

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          Most cited references23

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          Structure-antioxidant activity relationships of flavonoids and phenolic acids.

          The recent explosion of interest in the bioactivity of the flavonoids of higher plants is due, at least in part, to the potential health benefits of these polyphenolic components of major dietary constituents. This review article discusses the biological properties of the flavonoids and focuses on the relationship between their antioxidant activity, as hydrogen donating free radical scavengers, and their chemical structures. This culminates in a proposed hierarchy of antioxidant activity in the aqueous phase. The cumulative findings concerning structure-antioxidant activity relationships in the lipophilic phase derive from studies on fatty acids, liposomes, and low-density lipoproteins; the factors underlying the influence of the different classes of polyphenols in enhancing their resistance to oxidation are discussed and support the contention that the partition coefficients of the flavonoids as well as their rates of reaction with the relevant radicals define the antioxidant activities in the lipophilic phase.
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            Lupeol, a novel anti-inflammatory and anti-cancer dietary triterpene.

            In the Western world, an average of 250 mg per day of triterpenes (member of phytosterol family), largely derived from vegetable oils, cereals, fruits and vegetables is consumed by humans. During the last decade, there has been an unprecedented escalation of interest in triterpenes due to their cholesterol-lowering properties and evidence of this phenomenon include at least 25 clinical studies, 20 patents and at least 10 major commercially triterpene-based products currently being sold all around the world. Lupeol a triterpene (also known as Fagarsterol) found in white cabbage, green pepper, strawberry, olive, mangoes and grapes was reported to possess beneficial effects as a therapeutic and preventive agent for a range of disorders. Last 15 years have seen tremendous efforts by researchers worldwide to develop this wonderful molecule for its clinical use for the treatment of variety of disorders. These studies also provide insight into the mechanism of action of Lupeol and suggest that it is a multi-target agent with immense anti-inflammatory potential targeting key molecular pathways which involve nuclear factor kappa B (NFkappaB), cFLIP, Fas, Kras, phosphatidylinositol-3-kinase (PI3K)/Akt and Wnt/beta-catenin in a variety of cells. It is noteworthy that Lupeol at its effective therapeutic doses exhibit no toxicity to normal cells and tissues. This mini review provides detailed account of preclinical studies conducted to determine the utility of Lupeol as a therapeutic and chemopreventive agent for the treatment of inflammation and cancer.
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              The relative antioxidant activities of plant-derived polyphenolic flavonoids.

              The relative antioxidant activities, against radicals generated in the aqueous phase, of a range of plant-derived polyphenolic flavonoids, constituents of fruit, vegetables, tea and wine, have been assessed. The results show that compounds such as quercetin and cyanidin, with 3',4' dihydroxy substituents in the B ring and conjugation between the A and B rings, have antioxidant potentials four times that of Trolox, the vitamin E analogue. Removing the ortho-dihydroxy substitution, as in kaempferol, or the potential for electron delocalisation by reducing the 2,3 double bond in the C ring, as in catechin and epicatechin, decreases the antioxidant activity by more than 50%, but these structures are still more effective than alpha-tocopherol or ascorbate. The relative significance of the positions and extents of hydroxylation of the A and B rings to the total antioxidant activity of these plant polyphenolics is demonstrated.
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                Author and article information

                Journal
                Pharmacognosy Res
                Pharmacognosy Res
                PR
                Pharmacognosy Research
                Medknow Publications & Media Pvt Ltd (India )
                0976-4836
                0974-8490
                Oct-Dec 2014
                : 7
                : 4
                : 335-340
                Affiliations
                [1] Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt
                Author notes
                Address for correspondence: Dr. Jihan M. Badr, Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt. E-mail: jihanbadr2010@ 123456hotmail.com
                Article
                PR-7-335
                10.4103/0974-8490.158436
                4660512
                5139e589-e988-4acd-922a-3a98654ef520
                Copyright: © Pharmacognosy Research

                This is an open access article distributed under the terms of the Creative Commons Attribution NonCommercial ShareAlike 3.0 License, which allows others to remix, tweak, and build upon the work non commercially, as long as the author is credited and the new creations are licensed under the identical terms.

                History
                : 28 August 2014
                : 21 October 2014
                : 21 October 2015
                Categories
                Original Article

                Pharmacology & Pharmaceutical medicine
                antioxidant,loranthaceae,nuclear magnetic resonance,phragmanthera

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