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Anti-inflammatory β-sitosterols from the Asiatic loop-root mangrove Rhizophora mucronata attenuate 5-lipoxygenase and cyclooxygenase-2 enzymes

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Relation http://eprints.cmfri.org.in/15234/
https://www.sciencedirect.com/science/article/pii/S0039128X21000726
10.1016/j.steroids.2021.108860
 
Title Anti-inflammatory β-sitosterols from the Asiatic loop-root mangrove Rhizophora mucronata attenuate 5-lipoxygenase and cyclooxygenase-2 enzymes
 
Creator Chakraborty, Kajal
Joy, Minju
Raola, Vamshi Krishna
 
Subject Bioprospecting
Biochemical composition
Mangroves
 
Description Four biogenic β-sitosterol analogues were identified from methanolic extract of the leaves of loop-root mangrove Rhizophora mucronata. These were characterized as 4, 14, 23-trimethyl-3β-sitosterol (1), 7-ethyl-3β-sitosterol (2), sitosteryl-3β-(33E)-pent-33-enoate (3) and 12α-hydroxy-3β-sitosterol (4) based on comprehensive spectroscopic techniques. Anti-inflammatory activities of β-sitosterol 4 against pro-inflammatory enzymes 5-lipoxygenase and cyclooxygenase-2 were found to be significantly higher (IC50 1.85 and 1.92 mM, respectively) compared to those demonstrated by compounds of 1-3 (p < 0.05). These β-sitosterol analogues disclosed superior selectivity indices (1.43-2.07) with regard to inducible cyclooxygenase-2 than its constitutive isoform cyclooxygenase-1, when compared to the standard, ibuprofen (0.44). Antioxidant properties of 12α-hydroxy-β-sitosterol (4) were found to be significantly greater (IC50 1.43-1.67 mM) than those of other sitosterol analogues. Structure-activity correlation analyses put forward that the bioactive potencies of the titled β-sitosterols were positively correlated to their electronic parameters. Molecular docking simulations were carried out in the active sites of 5-lipoxygenase/cyclooxygenase-2, and the docking scores and binding energies of the studied β-sitosterol analogues were positively correlated with their attenuation properties against 5-lipoxygenase and cyclooxygenase-2.
 
Publisher Elsevier
 
Date 2021
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/15234/1/Steroids_2021_Kajal%20Chakraborty_Anti%20inflammatory.pdf
Chakraborty, Kajal and Joy, Minju and Raola, Vamshi Krishna (2021) Anti-inflammatory β-sitosterols from the Asiatic loop-root mangrove Rhizophora mucronata attenuate 5-lipoxygenase and cyclooxygenase-2 enzymes. Steroids, 172. pp. 1-10.