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Antioxidant spiropharanone, an undescribed variant of trans-decalin spiro-γ-lactone, from pharaoh cuttlefish Sepia pharaonis: Twin inhibitors of inflammatory 5-lipoxygenase and serine protease dipeptidyl peptidase-4

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Relation http://eprints.cmfri.org.in/15261/
https://onlinelibrary.wiley.com/doi/abs/10.1111/jfbc.13919
 
Title Antioxidant spiropharanone, an undescribed variant of
trans-decalin spiro-γ-lactone, from pharaoh cuttlefish Sepia
pharaonis: Twin inhibitors of inflammatory 5-lipoxygenase and
serine protease dipeptidyl peptidase-4
 
Creator Shilpa, K P
Chakraborty, Kajal
 
Subject Biochemistry
Cephalopods
Fish Biotechnology
Molluscan Fisheries
Food Chemistry
 
Description Marine pharaoh cuttlefish Sepia pharaonis (family Sepiidae) is regarded as an econom-ically important class of cephalopod in the coastal Mediterranean and Asian regions.
Bioassay-guided chromatographic purification of solvent extract of S. pharaonis led
to the identification of a trans-decalin based spirolactone, spiropharanone, which
was characterized as 1-hydroxy-7-(4′-methoxy-3-methylbut-2-enyl)-3,9,15-trimethyl
-8-oxo-octahydro-5H-spiro[furan-8,9-naphtho]-8-yl-acetate by spectroscopic tech-niques. Spiropharanone exhibited significantly greater anti-inflammatory activity by
attenuating pro-inflammatory 5-lipoxygenase (IC50 1.02 mM) than the non-steroidal
drug ibuprofen (IC50 4.61 mM, p ≤ .05). Superior antioxidant properties of spirophara-none against free radicals (EC50 ~1.20 mM) and other oxidants (hydroxyl [EC50
0.97 mM] and superoxide [EC50 1.47 mM] scavenging) also reinforced its promising
anti-inflammatory activity. The studied spiropharanone also exhibited significant at-tenuation toward insulin secretion regulating enzyme dipeptidyl peptidase-4 (IC50
0.92 mM) recognizing its anti-hyperglycemic potential. Significantly higher electronic
properties (topological polar surface area ~100) combined with balanced hydrophilic-lipophilic properties (partition coefficient of logarithmic octanol-water ~3) and lesser
docking parameters of spiropharanone demonstrated that the compound could be
utilized as an important bioactive lead against oxidative stress, inflammation, and
hyperglycemic-related ailments.
 
Publisher Wiley
 
Date 2021
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/15261/1/Journal%20of%20Food%20Biochemistry_2021_Chakraborty%20Kajal.pdf
Shilpa, K P and Chakraborty, Kajal (2021) Antioxidant spiropharanone, an undescribed variant of trans-decalin spiro-γ-lactone, from pharaoh cuttlefish Sepia pharaonis: Twin inhibitors of inflammatory 5-lipoxygenase and serine protease dipeptidyl peptidase-4. Journal of Food Biochemistry. pp. 1-13.