Lipoxygenase Inhibitory Constituents from Periploca a phylla (original) (raw)
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Natural product research, 2018
A new peroxy fatty acid, tagetnoic acid (5) [4-((3S,6S)-6-((3E,8E)-octadeca-3,8-dien-1-yl)-3,6-dihydro-1,2-dioxin-3-yl)butanoic acid] and four known metabolites: ecliptal (5-formyl-α-terthiophene) (1), 5-(4-hydroxybut-1-ynyl)-2,2'-bithiophene (2), 22,23-dihydrospinasterone (3), and stigmasterol (4) were separated from the n-hexane fraction of the aerial parts of Tagetes minuta L. (Asteraceae). Their chemical structures were verified using IR, UV, 2D and 1D NMR, and HRMS. Compounds 3-5 displayed potent lipoxygenase inhibitory potential with ICs 2.26, 1.83, and 1.17 μM, respectively compared to indomethacin (IC 0.89 μM). Moreover, molecular docking study revealed that the potent activity of 5 is due to H-bonding and hydrophobic interaction. The results of this study suggested that Tagetes minuta dietary consumption would be useful for the individuals at risk of acute and chronic inflammatory disorders.
Lipoxygenase Inhibition by Plant Extracts
Biomolecules
Lipoxygenases are widespread enzymes that catalyze oxidation of polyunsaturated fatty acids (linoleic, linolenic, and arachidonic acid) to produce hydroperoxides. Lipoxygenase reactions can be desirable, but also lipoxygenases can react in undesirable ways. Most of the products of lipoxygenase reactions are aromatic compounds that can affect food properties, especially during long-term storage. Lipoxygenase action on unsaturated fatty acids could result in off-flavor/off-odor development, causing food spoilage. In addition, lipoxygenases are present in the human body and play an important role in stimulation of inflammatory reactions. Inflammation is linked to many diseases, such as cancer, stroke, and cardiovascular and neurodegenerative diseases. This review summarized recent research on plant families and species that can inhibit lipoxygenase activity.
Periplocain A, a New Naphthalene Derivative from Periploca aphylla Growing in Saudi Arabia
Periplocain A (2), a new naphthalene derivative together with four known compounds: 2-ethylhexyl benzoate (1), quercetin-3-O-a-L-rhamnopyranoside (3), quercetin-3-O-b-D-glucopyranoside (4), and quercetin-3-(6-O-a-L-rhamnopyranosyl-bD-glucopyranoside) (5) were isolated from the AcOEt fraction of the aerial parts of Periploca aphylla (Asclepiadaceae). Their structures were established by multiple spectroscopic methods in addition to HR-ESI-MS and by comparison with literature data.
Journal of The Science of Food and Agriculture, 2009
BACKGROUND: The root powder of Periploca laevigata is used for preparing soft drinks and as an aromatic in Tunisia. The infusion or decoction of its root bark has widespread use in folk medicine. The plant is used to treat digestive disorders and hypertensive effects as well as other health problems.RESULTS: The antioxidant activities of extracts of P. laevigata root bark obtained with solvents of different polarity were investigated using assays of 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity, ferric-reducing capacity, β-carotene-bleaching ability, hydroxyl radical-scavenging activity and lipid peroxidation inhibition. The methanol extract, with the highest amount of total phenolics and flavonoids, showed the highest antioxidant activities in all assays, followed by the water extract. Gas chromatography/mass spectrometry was used to determine the composition of the water and methanol extracts. Thirty-four compounds were identified in the methanol extract, with proflavine (516.2 g kg−1 dry matter (DM)) and 4-methoxysalicylaldehyde (198.3 g kg−1 DM) being the most abundant. Sixteen compounds were identified in the water extract, of which 4-hydroxy-3-methoxyphenethylene glycol (351.2 g kg−1 DM) was the main component.CONCLUSION: As far as is known, this is the first report on the chemical composition and biological activities of phenolic extracts from P. laevigata. The results of the study indicate that the root bark of this plant might be a good candidate for further investigation in developing new antioxidants. Copyright © 2009 Society of Chemical Industry