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Highly oxygenated antioxidative 2H-chromen derivative from the red seaweed Gracilaria opuntia with pro-inflammatory cyclooxygenase and lipoxygenase inhibitory properties

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Relation http://eprints.cmfri.org.in/13360/
https://www.tandfonline.com/doi/full/10.1080/14786419.2017.1378209
https://doi.org/10.1080/14786419.2017.1378209
 
Title Highly oxygenated antioxidative 2H-chromen derivative from
the red seaweed Gracilaria opuntia with pro-inflammatory
cyclooxygenase and lipoxygenase inhibitory properties
 
Creator Chakraborty, Kajal
Makkar, Fasina
 
Subject Bioactive compounds
Biochemistry
Seaweed
 
Description Phytochemical investigation of the thalli of ethyl acetate-methanol
extract of the red seaweed Gracilaria opuntia led to isolation of a
substituted 2H-chromen derivative of unusual structure possessing
highly oxygenated carbon skeleton, characterised as 2-acetoxy-2-(5-
acetoxy-4-methyl-2-oxotetrahydro-2H-pyran-4-yl)ethyl 4-(3-methoxy-
2-(methoxymethyl)-7-methyl-3,4,4a,7,8,8a-hexahydro-2H-chromen-4-
yloxy)-5-methylheptanoate, which have not been reported in nature.
The chemical structure was resolved by detailed spectroscopic analysis.
The anti-inflammatory activity of the newly reported metabolite was
determined by pro-inflammatory cyclooxygenase and 5-lipoxygenase
inhibitory assays. The anti-inflammatory selectivity index of the
title compound recorded greater value (SI: anti-cycloxygense-1IC50
/anti-cycloxygense-2IC50
~ 1.26) than synthetic NSAIDs (aspirin and
ibuprofen, SI: 0.02 and 0.44, respectively), and consequently, appeared
to be safer. The antioxidative activity of the title compound was
significantly greater as determined by 2, 2-diphenyl-1-picrylhydrazyl
and 2, 2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid)
radical scavenging activities (IC50 0.26–0.32 mg/mL) compared to
α-tocopherol (IC50 > 0.6 mg/mL), and was comparable to the synthetic
antioxidants butylated hydroxytoluene and butylated hydroxyanisole
(IC50 ~ 0.25–0.34 mg/mL).
 
Publisher Taylor and Francis
 
Date 2018
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/13360/1/Kajal%20Chakraborty_2018_Natural%20Product%20Research_Highly%20oxygenated%20antioxidative%202H%20chromen%20derivative%20from%20the%20red%20seaweed%20Gracilaria%20opuntia%20with%20pro%20inflammatory%20cyclooxygenase%20and%20lipoxygenase.pdf
Chakraborty, Kajal and Makkar, Fasina (2018) Highly oxygenated antioxidative 2H-chromen derivative from the red seaweed Gracilaria opuntia with pro-inflammatory cyclooxygenase and lipoxygenase inhibitory properties. Natural Product Research, 32 (23). pp. 2756-2765. ISSN 1478-6427 (Online)