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Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana

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Relation http://eprints.cmfri.org.in/11937/
https://link.springer.com/article/10.1007/s00044-018-2182-0
 
Title Oxygenated heterocyclic metabolites with dual cyclooxygenase-2
and 5-lipoxygenase inhibitory potentials from Rhizophora
annamalayana
 
Creator Chakraborty, Kajal
Raola, Vamshi Krishna
 
Subject Bioactive compounds
Biochemistry
Mangroves
 
Description Previously undescribed oxygenated heterocyclic metabolites were purified from the ethyl acetate fraction of natural
mangrove hybrid Rhizophora annamalayana. The purified metabolites were characterized as 11-(tetrahydro-14α-hydroxy-
13β-methylfuran-12-yl)-10β-methylbutyl benzoate (1), 13-(tetrahydro-15β,16α-dimethyl-18-oxo-2H-pyran-14-yl)-10β-
methylhept-12(E)-enyl benzoate (2), and dihydro-11-((7E)-2-hydroxy-8β-methyl-2H-chromen-9-yl)-13-methylpent-12(E)-
enyl)-17β-methylfuran-19(3H)-one (3) by the combined spectroscopic experiments. These metabolites were assessed for
their antioxidant and anti-inflammatory activities, and compared with the commercially available standards. The purified
compound 3 exhibited greater antioxidant activities as deduced by 2, 2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid and
2, 2-diphenyl-1-picrylhydrazyl quenching properties (IC50 2.10 and 2.22 mM, respectively) compared to the positive control
(α-tocopherol, IC50 1.46 and 1.69 mM, respectively). Consequently, the anti-inflammatory activity of compound 3 with
regard to the inhibitory property towards pro-inflammatory 5-lipoxygenase was greater (IC50 2.16 mM) than that exhibited
by the synthetic anti-inflammatory drug ibuprofen (IC50 4.51 mM). Electronic and hydrophobic parameters were deduced to
find the target bioactivities of the studied compounds. These oxygenated heterocyclic metabolites could be used as potential
therapeutic lead compounds in the pharmaceutical applications.
 
Date 2018
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/11937/1/Kajal%20Chakraborty_2018_Medicinal%20Chemistry%20Research_Oxygenated%20heterocyclic%20metabolites%20with%20dual%20cyclooxygenase-2%20and%205-lipoxygenase%20inhibitory%20potentials.pdf
Chakraborty, Kajal and Raola, Vamshi Krishna (2018) Oxygenated heterocyclic metabolites with dual cyclooxygenase-2 and 5-lipoxygenase inhibitory potentials from Rhizophora annamalayana. Medicinal Chemistry Research, 27. pp. 1679-1689.