In silico and in vitro anti-inflammatory study of phenolic compounds isolated from Eucalyptus maculata resin

Plant resins are rich in bioactive compounds with high medicinal values. However, the chemistry and anti-inflammatory activity of the resins produced by trees of the genus Eucalyptus were scarcely investigated. The inflammatory targets cyclooxygenase-1 (COX-1), COX-2, TNF-, NF-B, and NO were signifi...

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Bibliographic Details
Published in:Scientific reports 2023-02, Vol.13 (1), p.2093-2093, Article 2093
Main Authors: Ali, Dalia E., Gedaily, Rania A. El, Ezzat, Shahira M., Sawy, Maged A. El, Meselhy, Meselhy R., Abdel-Sattar, Essam
Format: Article
Language:English
Subjects:
631/154
631/1647/2230
631/1647/2258
631/1647/767
692/53
Acids
Anti-inflammatory agents
Anti-Inflammatory Agents - pharmacology
Antioxidants
Bioactive compounds
Celecoxib
Cinnamic acid
Cyclooxygenase 2
Cyclooxygenase-1
Dichloromethane
Enzymes
Eucalyptus - chemistry
Eucalyptus maculata
Humanities and Social Sciences
Inflammation
Kaempferol
Medicinal plants
multidisciplinary
NF-kappa B
NF-κB protein
Oxidative stress
Pharmacy
Phenolic compounds
Phenols
Plant Extracts - pharmacology
Polyphenols
Resins
Science
Science (multidisciplinary)
Tumor necrosis factor-TNF
Tumor necrosis factor-α
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Summary:Plant resins are rich in bioactive compounds with high medicinal values. However, the chemistry and anti-inflammatory activity of the resins produced by trees of the genus Eucalyptus were scarcely investigated. The inflammatory targets cyclooxygenase-1 (COX-1), COX-2, TNF-, NF-B, and NO were significantly inhibited by the methanolic extract of Eucalyptus maculata kino resin (EME) and its CH 2 Cl 2 soluble fraction (MCF). Sakuranetin ( C1 ), ( E )-cinnamic acid ( C2 ), kaempferol 7- methyl ether ( C3 ), 7- O -methyl aromadendrin ( C4 ), and 1,6- dicinnamoyl- O-α -D-glucopyranoside ( C5 ) were isolated from MCF. Three compounds ( C1 , C2, and C4 ) showed potent in vitro COX-1 inhibition, while C5 inhibited COX-2, TNF- α , NF-κB, and NO significantly. An in-silico study revealed that C5 had the highest binding affinity to the active site in COX-2 with binding energy score (S) of -14.85 kcal/mol, better than celecoxib (COX-2 inhibitor). In conclusion, 1,6-dicinnamoyl- O-α -D-glucopyranoside ( C5 ) could be investigated further in the search for anti-inflammatory agents.
ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-023-28221-y