Anti-inflammatory polyoxygenated furanocembranoids, salmacembranes A–B from the sea urchin Salmacis bicolor attenuate pro-inflammatory cyclooxygenases and lipoxygenase

Francis, Prima and Chakraborty, Kajal (2020) Anti-inflammatory polyoxygenated furanocembranoids, salmacembranes A–B from the sea urchin Salmacis bicolor attenuate pro-inflammatory cyclooxygenases and lipoxygenase. Medicinal Chemistry Research, 29. pp. 2066-2076.

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Abstract

Two undescribed polyoxygenated furanocembranoid derivatives, methyl 15-(9-hydroxy-8-methoxy-2,12-dimethyl-15-oxa-bicyclo [10.2.1]pentadeca-2,4,6,11-tetraen-3-yl)propanoate (salmacembrane A) and 1-(16-methyl-2,16-dihydrofuran)-8-methoxy-12- methyl-20-oxabicyclo[10.2.1]pentadeca-2,4,6,11-tetraen-9-ol (salmacembrane B), were isolated from the organic extract of sea urchin Salmacis bicolor (family Temnopleuridae) by extensive chromatographic purification. Their structures were elucidated using detailed spectroscopic evidence. Salmacembrane A displayed significantly greater attenuation property against pro-inflammatory cyclooxygenase-2 (IC50 1.71 mM) than that exhibited by salmacembrane B (IC50 1.99 mM). Salmacembrane A could potentially inhibit 5-lipoxygenase (IC50 1.87 mM) and its activity was significantly greater than that exhibited by anti-inflammatory agent ibuprofen (IC50 4.50mM, p < 0.05). The greater selectivity index (anti-cyclooxygense-2/anti-cyclooxygense-1) of salmacembrane A (1.06) than ibuprofen (0.43) further supported higher selectivity toward pro-inflammatory isoenzyme cyclooxygenase-2. Salmacembrane A displayed higher antioxidant properties against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) and 2,2- diphenyl-1-picrylhydrazyl (IC50 1.57 and 1.65mM, respectively) than those exhibited by salmacembrane B (IC50 > 1.85mM). In addition, these antioxidant activities were comparable to the standard α-tocopherol (IC50 DPPH 1.51 mM, IC50 ABTS+ 1.70mM p < 0.05). The higher electronic parameters obtained from structure–activity relationship analysis along with greater binding affinities of salmacembrane A at the active site of cyclooxygenase-2 ascribed its potential anti-inflammatory activity.

Item Type:	Article
Uncontrolled Keywords:	Sea urchin; Salmacis bicolor; Salmacembranes; Polyoxygenated furanocembranoids; Anti-inflammatory activity; Selectivity index
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:	13 Oct 2020 04:53
Last Modified:	13 Oct 2020 04:53
URI:	http://eprints.cmfri.org.in/id/eprint/14687

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