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Previously undescribed antioxidative and anti-inflammatory chromenyls bearing 3H-isochromenone and furanyl-2H-chromenyl skeletons from the venerid clam, Paphia malabarica

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Relation http://eprints.cmfri.org.in/9960/
 
Title Previously undescribed antioxidative and anti-inflammatory
chromenyls bearing 3H-isochromenone and furanyl-2H-chromenyl
skeletons from the venerid clam, Paphia malabarica
 
Creator Joy, Minju
Chakraborty, Kajal
 
Subject Bioactive compound
Clam
 
Description Previously undescribed chromenyl derivatives,
characterized as 7-(2′-ethyl-1′-hydroxynonan-2′-yl)-6,7,8,
8a-tetrahydro-3H-isochromen-1-(5H)-one (1) and 61-(3-
((E)-31b-(furan-2′-yl)-prop-31b-en-31-yl)-4a,5,6,8a-tetrahydro-
8-methyl-2H-chromen-6-yl)-ethyl-5′′-methyl-hexanoate (2)
were isolated from ethyl acetate-methanol extract of yellowfoot
bivalve clam, Paphia malabarica. Their structures have
skeletons composed of isochromen-(5H)-one and furanyl-2Hchromenyl
moieties, which are reported for the first time in
marine organism. These were characterized by extensive one
and two-dimensional nuclear magnetic resonance, infrared,
and high-resolution mass spectroscopic experiments. The title
compounds were evaluated for therapeutic potentials with
regard to anti-inflammatory and antioxidant properties compared
to known standards. These compounds exhibited
comparable 2, 2-diphenyl-1-picrylhydrazyl (DPPH) and 2, 2′-
azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS+)
radical scavenging activities with α-tocopherol (IC50
~0.6–0.7mg/mL). The significantly higher anti-5-
lipoxygenase activity of the title compounds (IC50
0.76–0.82mg/mL) than ibuprofen (IC50 0.93 mg/mL) indicated
their potential anti-inflammatory properties. The selectivity
indices (IC50 anti-cyclooxygenase-1/IC50anticyclooxygenase-
2) of compounds 1 (1.19) and 2 (1.31) well
established its safety profiles as an anti-inflammatory when
compared to known drug, ibuprofen (0.44). The target
bioactivities of chromenyl derivatives were guided by
hydrophobic and electronic parameters. These compounds
can be used as potential bioactive leads in functional food and
medicinal applications.
 
Date 2017
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/9960/1/Antioxidative%20and%20anti-inflammatory%20chromenyls%20from%20Paphia%20malabarica_Medicinal%20Chemistry%20Research_2017_Kajal%20Chakraborty.pdf
Joy, Minju and Chakraborty, Kajal (2017) Previously undescribed antioxidative and anti-inflammatory chromenyls bearing 3H-isochromenone and furanyl-2H-chromenyl skeletons from the venerid clam, Paphia malabarica. Medicinal Chemistry Research, 65. pp. 1-15.