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Antioxidant and anti-inflammatory cembrane-type diterpenoid from Echinoidea sea urchin Stomopneustes variolaris attenuates pro-inflammatory 5-lipoxygenase

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Relation http://eprints.cmfri.org.in/14164/
https://link.springer.com/article/10.1007%2Fs00044-020-02511-w
10.1007/s00044-020-02511-w
 
Title Antioxidant and anti-inflammatory cembrane-type diterpenoid from Echinoidea sea urchin Stomopneustes variolaris attenuates pro-inflammatory 5-lipoxygenase
 
Creator Francis, Prima
Chakraborty, Kajal
 
Subject Bioactive compounds
Biochemistry
Echinoderms
Sea Urchin
 
Description Chemical investigation of pharmacologically active compounds from the Echinoidea sea urchin Stomopneustes variolaris resulted in the separation of an unreported cembrane type of diterpenoid, which was characterised as 4-hydroxy-1-(16-methoxyprop-16-en-15-yl)-8-methyl-21,22-dioxatricyclo[11.3.1.15,8]octadecane-3,19-dione by spectroscopic experiments. The compound exhibited greater inhibitory potential against inflammatory agent 5-lipoxygenase (IC50 2.01 mM) than that exhibited by synthetic ibuprofen (IC50 4.50 mM). The selectivity ratio of cyclooxygenase-1 to cyclooxygenase-2 for the studied compound was found to be greater (1.25) than that of ibuprofen (0.43), which could be accounted for the prospective anti-inflammatory property of the cembrane-type diterpenoid against inducible pro-inflammatory cyclooxygenase-2. Potent antioxidant activity of the studied compound was characterised by its greater scavenging effects on 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid radicals (IC50 1.41 and 1.61 mM, respectively) than the standard antioxidative agent α-tocopherol (IC50 1.51 and 1.70 mM, respectively). The greater electronic parameters (topological polar surface area of 82.06) together with two hydrogen bonded interactions at the active site of cyclooxygenase-2 and lesser binding energy (−8.91 kcal/mol) corroborated its prospective anti-inflammatory activity. Therefore, the presently studied cembrane-type diterpenoid could be utilised in medicinal formulations as an effective anti-inflammatory agent.
 
Date 2020
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/14164/1/Medicinal%20Chemistry%20Research_2020_Kajal%20Chakraborty_Antioxidant%20and%20anti-inflammatory%20cembrane-typediterpenoid%20from%20Echinoidea%20sea%20urchin.pdf
Francis, Prima and Chakraborty, Kajal (2020) Antioxidant and anti-inflammatory cembrane-type diterpenoid from Echinoidea sea urchin Stomopneustes variolaris attenuates pro-inflammatory 5-lipoxygenase. Medicinal Chemistry Research, 29. pp. 656-664.