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Bioassay-guided isolation, identification and molecular ligand-target insight of lipoxygenase inhibitors from leaves of Anisomeles malabarica R.Br.

ABSTRACT: BACKGROUND:Anisomeles malabarica R. Br. (Lamiaceae) is extensively used in traditional medicine in major parts of India for several medicinal purposes, including their use in rheumatism. MATERIALS AND METHODS:The air-dried leaves of A. malabarica were extracted with ethanol, defatted with n-hexane and then successively partitioned into chloroform and n-butanol fractions. Bioassay-guided fractionation and purification of chloroform fraction from A. malabarica lead to the isolation of lipoxygenase (LOX) inhibitors. The structures of isolated compounds were elucidated by ultraviolet, infrared, (1)H nuclear magnetic resonance (NMR), (13)C NMR and mass spectrometry spectroscopic techniques and assessed further by in vitro soybean lipoxygenase (sLOX) assay. In addition, the enzyme type inhibition was evaluated through molecular docking technique as a part of computational study. RESULTS:The bioactive compounds 3, 4 dihydroxy benzoic acid (1) and 4', 5, 7-trihydroxyflavone (2) were isolated from chloroform fraction of A. malabarica, whose bioactivity was observed to be dose-dependent compared to n-butanol fraction. Among the compounds, 3, 4 dihydroxy benzoic acid showed significant sLOX inhibitory activity with 74.04% ±2.6% followed by 4', 5, 7-trihydroxyflavone (34.68% ±1.9%). The computational analysis of compounds showed their molecular interaction with important amino acid residues and nonheme iron atom in the catalytic site of LOX by enlightening their potential binding mode at molecular level. CONCLUSIONS:The LOX inhibitory constituents were identified from A. malabarica by means of bioassay-guided fractionation process. The results derived from in vitro and computational experiments confirm the potential of the isolated compounds and provide additional evidence for its traditional use in inflammatory disorders.

SUBMITTER: Sudha A

PROVIDER: S-EPMC4189278 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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Bioassay-guided isolation, identification and molecular ligand-target insight of lipoxygenase inhibitors from leaves of Anisomeles malabarica R.Br.

Sudha A A Srinivasan P P

Pharmacognosy magazine 20140801 Suppl 3

<h4>Background</h4>Anisomeles malabarica R. Br. (Lamiaceae) is extensively used in traditional medicine in major parts of India for several medicinal purposes, including their use in rheumatism.<h4>Materials and methods</h4>The air-dried leaves of A. malabarica were extracted with ethanol, defatted with n-hexane and then successively partitioned into chloroform and n-butanol fractions. Bioassay-guided fractionation and purification of chloroform fraction from A. malabarica lead to the isolation ...[more]

PMID: 25298680

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Project description:To avoid the widespread resistance of commercial fungicides, new broad-spectrum botanical fungicides need to be developed. In previous bioactive screening assays, extracts of Artemisia ordosica Krasch. (A. ordosica) had highly antifungal activities, but the responsible phytochemicals were unidentified. In this study, active compounds of A. ordosica extracts were identified using a bioassay-guided method, and antifungal assays were performed in vitro and in vivo. The bioactive compounds were dissolved in petroleum ether, and the best antifungal fraction contained four compounds: trans-dehydromatricaria ester (TDDE), 7, 4-demetylnringenin, capillarin, and stearic acid. Among them, TDDE exhibited the highest antifungal activity against six pathogenic fungi and five bacteria. It exhibited significant fungicidal activity against Thanatephorus cucumeris and Botrytis cinerea with EC50 values of 0.464 μg/mL and 1.4 μg/mL, respectively. The living tissue bioassay results showed that the relative protection effects (RPE) of TDDE on tomato leaves, tomato fruit, and strawberry leaves infected with B. cinerea reached 76.78%, 86.2%, and 80.89%, respectively. In pot experiments, the RPE on tomato and strawberry plants infected with B. cinerea reached 84.11% and 96.37%, respectively. Morphological and physiological examination showed that TDDE had significant inhibitory effects on mycelial growth, including increased top offshoot, contorted hyphal tips, and extravasated cytochylema. Meanwhile, bactericidal activities of TDDE were significantly higher than kanamycin and streptomycin in five bacteria, and the plant tissue experiments further demonstrated that it had an 88.31% RPE on walnut leaves infected with Xanthomonas campestris pv. jugiandis, 72.18% RPE on potato infected with Erwinia carotovora subsp. carotovora, and 82.50% RPE on kiwifruit branches infected with Pseudomonas syringae pv. actinidiae. The active compounds isolated from A. ordosica in this study show great potential value for developing broad-spectrum fungicides, and also provide an important way to identify and isolate new bioactive products from medicinal plants.

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Bioassay-guided isolation, identification and molecular ligand-target insight of lipoxygenase inhibitors from leaves of Anisomeles malabarica R.Br.

Publications

Bioassay-guided isolation, identification and molecular ligand-target insight of lipoxygenase inhibitors from leaves of Anisomeles malabarica R.Br.

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