Characterization of substituted aryl meroterpenoids from red seaweed Hypnea musciformis as potential antioxidants

Chakraborty, Kajal and Joseph, Deepu and Joy, Minju and Raola, Vamshi Krishna (2016) Characterization of substituted aryl meroterpenoids from red seaweed Hypnea musciformis as potential antioxidants. Food Chemistry, 212. pp. 778-788.

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Abstract

The ethyl acetate fraction of red seaweed Hypnea musciformis was purified to yield three substituted aryl meroterpenoids, namely, 2-(tetrahydro-5-(4-hydroxyphenyl)-4-pentylfuran-3-yl)-ethyl-4-hydroxy benzoate (1), 2-2-[(4-hydroxybenzoyl)-oxy]-ethyl-4-methoxy-4-2-[(4-methylpentyl)oxy]-3,4-dihydro-2 H-6-pyranylbutanoic acid (2) and 3-((5-butyl-3-methyl-5,6-dihydro-2H-pyran-2-yl)-methyl)-4-meth oxy-4-oxobutyl benzoate (3). The structures of these compounds, as well as their relative stereochemistries, were confirmed by exhaustive NMR spectroscopic data analyses. Compound 1 exhibited similar 2,20-diphenylpicrylhydrazyl radical inhibiting and Fe2+ ion chelating activities (IC50 25.05 and 350.7 lM, respectively) as that of commercial antioxidant gallic acid (IC50 32.3 and 646.6 lM, respectively), followed by 3 (IC50 231.2 and 667.9 lM, respectively), and 2 (IC50 322.4 and 5115.3 lM, respectively), in descending order of activities. Structure-activity relationship analysis revealed that the antioxidant activities of these compounds were directly proportional to the steric and hydrophobic parameters. The seaweed derived aryl meroterpenoids might serve as potential lead antioxidative molecules for use in pharmaceutical and food industries.

Item Type:	Article
Uncontrolled Keywords:	Seaweed; Hypnea musciformis; Antioxidant activity; Aryl meroterpenoids; Nuclear magnetic resonance; spectroscopy; Structure-activity relationship
Subjects:	Fish Biotechnology > Bioactive compound Algae > Seaweed
Divisions:	CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division Subject Area > CMFRI-Kochi > Marine Biotechnology, Fish Nutrition and Health Division
Depositing User:	Arun Surendran
Date Deposited:	09 Dec 2016 06:44
Last Modified:	09 Dec 2016 06:44
URI:	http://eprints.cmfri.org.in/id/eprint/11337

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