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Prospective natural anti-inflammatory drimanes attenuating proinflammatory 5-lipoxygenase from marine macroalga Gracilaria salicornia

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Relation http://eprints.cmfri.org.in/13642/
https://www.sciencedirect.com/science/article/pii/S221192641830866X?via%3Dihub
https://doi.org/10.1016/j.algal.2019.101472
 
Title Prospective natural anti-inflammatory drimanes attenuating proinflammatory
5-lipoxygenase from marine macroalga Gracilaria salicornia
 
Creator Chakraborty, Kajal
Antony, Tima
Joy, Minju
 
Subject Bioactive compound
Biochemistry
Algae
 
Description The 5-lipoxygenase-associated cascade has appeared as potential therapeutic target in attenuating inflammatory
pathologies. Progression and pathophysiology of inflammation have also shown potential involvement of oxidative
stress and inflammatory pathways. Three drimane sesquiterpene quinols, characterised as 3-(hept-36-
enyloxy)-decahydro-4,6a,12a,12b-tetramethyl-1H-benzo[a]xanthene-4,10,12-triol (1), 13-[[2-(hexyloxy)-
2,5,5,8a-tetramethyldecahydro-1-naphthalenyl](methoxy)methyl]benzenol (2), and 1-butoxy-4,4,11b,11c-tetramethyl-
decahydrobenzo[kl]xanthen-10-ol (3) were purified from the organic extract of intertidal marine
macroalga Gracilaria salicornia, obtained from the southeast coastal regions of Indian peninsular. The 1H-benzo
[a]xanthene-triol derivative (1) registered potential activities against pro-inflammatory 5-lipoxygenase (IC50
1.7 mM) and free radicals (IC50 1.3–1.6 mM). The in silico molecular modelling studies to designate 5-lipoxygenase
inhibitory mechanism of the studied analogues and the comparison of docking parameters attributed
that the drimane sesquiterpene 1 exhibited least binding energy of −12.30 kcal mol−1, and showed effective
hydrogen bonding interactions with the catalytic site of the enzyme. The higher electronic parameters and
permissible hydrophobic-hydrophilic balance of the drimane sesquiterpene bearing 1H-benzo[a]xanthene-triol
moiety (1) appeared to constitute significant roles towards the attenuation of pro-inflammatory 5-lipoxygenase.
Putative biosynthetic pathway of the studied compounds involving cyclisation of farnesyl diphosphate and
carbocationic rearrangement through a battery of enzyme-mediated cascade validated their structural attributions.
These results demonstrated that the drimane-type sesquiterpenoids with 1H-benzo[a]xanthene-triol framework
could be used as a potential therapeutic agent for the treatment of 5-lipoxygenase-mediated inflammatory
pathologies.
 
Date 2019
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/13642/1/Kajal%20Chakraborty_2019_Algal%20Research_Natural%20anti-inflammatory%20drimanes%20attenuating%20pro-inflammatory%205-lipoxygenase%20from%20marine%20macroalga%20Gracilaria%20salicornia.pdf
Chakraborty, Kajal and Antony, Tima and Joy, Minju (2019) Prospective natural anti-inflammatory drimanes attenuating proinflammatory 5-lipoxygenase from marine macroalga Gracilaria salicornia. Algal Research, 40. pp. 1-11.