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.
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Medicinal Chemistry Research_2020_Kajal Chakraborty_Antioxidant and anti-inflammatory cembrane-typediterpenoid from Echinoidea sea urchin.pdf Restricted to Registered users only Download (1MB) | Please mail the copy request to cmfrilibrary@gmail.com |
Abstract
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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | Echinoidea sea urchin; Stomopneustes variolaris; Cembrane-type diterpenoid; Anti-inflammatory activity; Proinflammatory 5-lipoxygenase |
| Subjects: | Biochemistry > Bioactive compounds Biochemistry Echinoderms Echinoderms > Sea Urchin |
| Divisions: | CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division Subject Area > CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division |
| Depositing User: | Arun Surendran |
| Date Deposited: | 23 Mar 2020 05:18 |
| Last Modified: | 23 Mar 2020 05:18 |
| URI: | http://eprints.cmfri.org.in/id/eprint/14164 |
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