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

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Relation http://eprints.cmfri.org.in/14687/
https://link.springer.com/article/10.1007%2Fs00044-020-02620-6
https://doi.org/10.1007/s00044-020-02620-6
 
Title Anti-inflammatory polyoxygenated furanocembranoids,
salmacembranes A–B from the sea urchin Salmacis bicolor attenuate
pro-inflammatory cyclooxygenases and lipoxygenase
 
Creator Francis, Prima
Chakraborty, Kajal
 
Subject Bioactive compounds
Biochemistry
Echinoderms
Sea Urchin
 
Description 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.
 
Date 2020
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/14687/1/Medicinal%20Chemistry%20Research_2020_Kajal%20Chakraborty_Anti-inflammatory%20polyoxygenated%20furanocembranoids.pdf
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.