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First report of two new antioxidative meroterpeno 2H-pyranoids from short-necked yellow-foot clam Paphia malabarica (family: Veneridae) with bioactivity against pro-inflammatory cyclooxygenases and lipoxygenase

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Relation http://eprints.cmfri.org.in/11338/
https://www.ncbi.nlm.nih.gov/pubmed/27471883
 
Title First report of two new antioxidative meroterpeno
2H-pyranoids from short-necked yellow-foot clam Paphia
malabarica (family: Veneridae) with bioactivity against
pro-inflammatory cyclooxygenases and lipoxygenase
 
Creator Joy, Minju
Chakraborty, Kajal
 
Subject Clam
New record
Bioactive compounds
 
Description Two new meroterpeno 2H-pyranoids were isolated from the
EtOAc:MeOH extract of yellow-foot clam Paphia malabarica. The
structures of these newly reported compounds were elucidated based
on spectroscopic interpretations. This is the first report of biogenic
2H-pyrans bearing decadienyl and allyloxy-(isopentanyl)-cyclohexene
skeletons from marine biota. The extended C18 sesquiterpenoid
with prenylated irregular farnesene framework was characterised
as 2-((E)-deca-1,8-dien-10-yl)-11,12-dihydro-13-propyl-2H-pyran (1).
The compound 2, 1′-((10E)-10-(10-(pentan-4-yl)-cyclohex-4-enyl)-
allyloxy)-tetrahydro-2′,2′-dimethyl-2H-pyran represents the first
example of naturally occurring C21 prenylated bisabolene-type
meroterpenoid, whereas tetrahydro-2′,2′-dimethyl-2H-pyran remains
attached at C-2′ position of rearranged bisabolene framework formed
by allyloxy linkage. The antioxidant activities (DPPH/ABTS+) of 1 and
2 were comparable (IC50 < 1.0 mg/mL) with α-tocopherol. In addition,
these compounds exhibited greater activity against cyclooxygenase-2
than COX-1, and the selectivity indices were significantly lesser (~1.1).
No significant differences in anti-5-lipoxygenase activity of 1 and 2
(IC50 1.02–1.06 mg/mL) than ibuprofen (IC50 0.93 mg/mL) indicated the
potential anti-inflammatory properties of title compounds.
 
Publisher Taylor and Francis
 
Date 2016
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/11338/1/First%20report%20of%20two%20new%20antioxidative%20meroterpeno_Natural%20Product%20research_Kajal%20Chakraborty_2016.pdf
Joy, Minju and Chakraborty, Kajal (2016) First report of two new antioxidative meroterpeno 2H-pyranoids from short-necked yellow-foot clam Paphia malabarica (family: Veneridae) with bioactivity against pro-inflammatory cyclooxygenases and lipoxygenase. Natural Product Research. pp. 1-11. ISSN 1478-6427 (Online)