Study of two isoforms of lipoxygenase by kinetic assays, docking and molecular dynamics of a specialised metabolite isolated from the aerial portion of Lithrea caustica (Anacardiaceae) and its synthetic analogs

Muñoz-Ramírez, Alejandra; Torrent-Farías, Claudia; Mascayano-Collado, Carolina; Urzúa-Moll, Alejandro

doi:10.1016/j.phytochem.2020.112359

Cited by 3 publications

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“…The solvent was evaporated under reduced pressure in a rotatory evaporator, yielding the corresponding acetyl derivatives. The products from each reaction were purified by column chromatography and analyzed by FTIR and 1 H and 13 C NMR were identified as ( Z )-1,2-diacetyl-3-(pentadec-10’-enyl)-benzene ( 4 ) and 1,2-diacetyl-3-pentadecylbenzene ( 5 ) ( Muñoz-Ramírez et al, 2020 ).…”

Section: Methodsmentioning

confidence: 99%

Inhibition of Soybean 15-Lipoxygenase and Human 5-Lipoxygenase by Extracts of Leaves, Stem Bark, Phenols and Catechols Isolated From Lithraea caustica (Anacardiaceae)

et al. 2020

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Lithraea caustica (Molina) Hook. and Arn. (Anacardiaceae), common name Litre, is an evergreen endemic plant used in the Mapuche Chilean folk medicine. The stem juice of L. caustica mixed with Rubus ulmifolius (blackberry) is used to treat cough and the infusion of leaves is used in baths to treat joint inflammations. In this study, the activities of 3-n-alk(en)yl-catechols, obtained from the dichloromethane extract of the epicuticular compounds of fresh leaves (DCME), stem bark petroleum ether extract (PEE), fractions of phenols and phenol-acid compounds obtained from the methanolic extract (methanolic extract) of defatted leaves and aqueous infusion (AE) from fresh leaves, were evaluated as in vitro inhibitors of soybean 15-lipoxygenase (15-sLOX) and human 5-lipoxygenase (5-hLOX), one of the inflammation pathways. The 3-n-alk(en)yl-catechols were characterized by gas chromatography-mass spectrometry and 1D and 2D nuclear magnetic resonance analysis as mixtures of 3-[(10E)-pentadec-10′-en-1-yl]-catechol, 3-[(10Z)-pentadec-10′-en-1-yl]-catechol and 3-n-pentadecylcatechol. In addition, two fractions, obtained from MeOHE, were characterized by liquid chromatography electrospray ionization tandem mass spectrometric as complex mixtures of known acids and phenolic compounds. DCME, MeOHE and ethyl acetate extract (AcOEtE) extracts showed inhibition against 15-sLOX, and the AE of fresh leaves, showed the best inhibition against 5-hLOX. The mixture of 3-n-alk(en)yl-catechols showed inhibition of 15-sLOX and 5-hLOX. The compounds 3-[(10Z)-pentadec-10′-en-1-yl]-catechol (IC50 2.09 µM) and 3-n-pentadecylcatechol (IC50 2.74 µM) showed inhibition against 5-hLOX. The inhibition values obtained for the 3-n-alk(en)yl-catechols are in the range of well-known inhibitors of 5-hLOX. Acetylation of the 3-n-alk(en)yl-catechols blocks the inhibitory activity, indicating that the free catechol function is necessary for the enzyme inhibition. In addition, the fractions of phenols and phenol-acid compounds showed inhibitory activity against 15-sLOX and the AE, showed a good inhibition against 5-hLOX. These results would be in agreement with the use of L. caustica, as an anti-inflammatory in Mapuche ethnomedicine.

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Section: Methodsmentioning

confidence: 99%

Inhibition of Soybean 15-Lipoxygenase and Human 5-Lipoxygenase by Extracts of Leaves, Stem Bark, Phenols and Catechols Isolated From Lithraea caustica (Anacardiaceae)

et al. 2020

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“…Natural anti-oxidants from plants counteract and attenuate cellular oxidative stress, reducing various diseases (Xu et al, 2017;Jamshidi-kia et al, 2020;Muñoz-Ramírez et al, 2020). Despite these established studies and advancements made, diseases such as cardiovascular diseases (CVD), inflammatory and metabolic disorders are prevalent and widespread in society.…”

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Morphology, phytochemistry, and medicinal properties of South African Mangifera indica L. leaves for summer and winter seasons.

Maharaj

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Herbal preparations of plants continue to present mankind with novel remedies as many of these plants contain important secondary metabolites. Plant species of the family Anacardiaceae are rich in bioactive phytochemicals. Mangifera indica (Anacardiaceae) is an introduced and naturalised species to South Africa. Herbal use of this plant has not been fully documented; however, it is used in traditional medicine. This study aimed at characterizing the morphology, phytochemistry, and biological activity of Mangifera indica leaves harvested in winter and summer. The foliar biology of the plant was conducted by various microscopy techniques such as stereo- and Scanning electron microscopy. The length and diameter of the different trichome types were measured using ImageJ. The non-glandular trichome lengths range between 70 - 200 μm. The peltate gland trichomes consist of 2 rows of 8 oblong cells each with a size ranging from 32- 48 μm. Morphological observations using stereo- and SEM revealed the presence of non-glandular trichomes with cuticular warts and glandular peltate trichomes on the leaves of Mangifera indica. Transmission electron micrographs showed the presence of numerous mitochondria, starch grains, plastoglobuli, and plastids. The results for summer and winter leaves resembled somewhat similar-to-identical morphological characteristics on all fronts. For the phytochemical and biological assays, this study aimed to investigate some of the phytochemical and biological properties using different solvents (hexane, chloroform, and methanol) for extraction of the leaves of Mangifera indica for the summer and winter seasons. Preliminary phytochemical screening for the hexane, chloroform and methanolic extracts was done using a reflux extraction apparatus to uncover the presence of different metabolites and the anti-oxidant screening was done by the radical scavenging activity, which was established using the 2,2-diphenyl-1-picrylhydrazyl assay. Potent radical scavenging activity was exhibited for both summer and winter seasons with hexane and methanolic extracts for summer (IC50 of 19.53 μg/mL and 12.71 μg/mL respectively) and winter (22.32 μg/mL and 14.35 μg/mL respectively) in comparison to the control ascorbic acid which produced an IC50 of 3.20 μg/mL. The summer extracts had better radical scavenging IC50 capacity than winter extracts. The antibacterial activity of the methanolic leaf extracts for summer and winter of Mangifera indica were evaluated against the bacterial species: Gram-negative Escherichia coli (ATCC 25922) and Gram-positive: Staphylococcus aureus (ATCC ATCC 43300). For S. aureus (ATTC 43300), the summer crude extract displayed lower antibacterial activity than the control streptomycin, the summer extracts had a zone of inhibition of 14.17 mm while streptomycin had a 16.67 mm zone of inhibition. winter extracts had a zone of inhibition of 12 mm while streptomycin had a 13.67 mm zone of inhibition. For E. coli (ATCC 25922), the summer crude extract displayed higher antibacterial activity than the control gentamycin; the summer extract had a zone of inhibition of 18.05 mm while gentamycin had a 17.5 mm zone of inhibition. The winter extracts had a zone of inhibition of 8.5 mm. while gentamycin had a 14.5 mm zone of inhibition. Between seasons, summer had better antibacterial activity compared to winter for both Gram-positive and Gram-negative bacteria. Phytochemical screening showed the presence of phenols, flavonoids, tannins, and terpenoids, alkaloids, phytosterols, saponins, steroids, and carbohydrates. Potent radical scavenging activity was exhibited for the hexane and methanolic extracts for summer and winter, indicating that Mangifera indica is a potential source of medicinally important compounds. Antibacterial screening showed positive results with antibacterial properties for both summer and winter samples revealing its valuable biological activities. Summer overall performed better than the winter season. Future studies on this plant species are recommended to advance the use of indigenous herbal medicine or produce novel drug leads. To our knowledge, this study represents the first recent investigation in South Africa describing key foliar micromorphological features, phytochemicals, and biological activities of Mangifera indica L.

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New insight in secretory structures and secretion composition in Rhus typhina L. – Anatomical, histochemical, and ultrastructural studies

Konarska

2024

Micron

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Study of two isoforms of lipoxygenase by kinetic assays, docking and molecular dynamics of a specialised metabolite isolated from the aerial portion of Lithrea caustica (Anacardiaceae) and its synthetic analogs

Cited by 3 publications

References 27 publications

Inhibition of Soybean 15-Lipoxygenase and Human 5-Lipoxygenase by Extracts of Leaves, Stem Bark, Phenols and Catechols Isolated From Lithraea caustica (Anacardiaceae)

Inhibition of Soybean 15-Lipoxygenase and Human 5-Lipoxygenase by Extracts of Leaves, Stem Bark, Phenols and Catechols Isolated From Lithraea caustica (Anacardiaceae)

Morphology, phytochemistry, and medicinal properties of South African Mangifera indica L. leaves for summer and winter seasons.

New insight in secretory structures and secretion composition in Rhus typhina L. – Anatomical, histochemical, and ultrastructural studies

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