Novel Furanyl-Substituted Isochromanyl Class of Anti-Inflammatory Turbinochromanone from Brown Seaweed Turbinaria conoides

Dhara, Subhajit and Chakraborty, Kajal (2022) Novel Furanyl-Substituted Isochromanyl Class of Anti-Inflammatory Turbinochromanone from Brown Seaweed Turbinaria conoides. Chemistry and Biodiversity.

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Abstract

Organic extract of the brown seaweed Turbinaria conoides (Sargassaceae) was chromatographically fractionated to yield an undescribed furanyl-substituted isochromanyl metabolite, named as turbinochromanone, which was characterized as methyl 4-[(3S)-8-{[(3R)-4-ethyl-2,3-dihydrofuran-3-yl]methyl}-1-oxo-3,4-dihydro-1H-2- benzopyran-3-yl]butanoate. The isochromanyl derivative possessed comparable attenuation potential against 5- lipoxygenase (IC50 3.70 μM) with standard 5-lipoxygenase inhibitor drug zileuton (IC50 2.41 μM). Noticeably, the index of anti-inflammatory selectivity of turbinochromanone (~1.7) was considerably greater than that exhibited by the standard agent diclofenac (1.06). Antioxidant properties of turbinochromanone against oxidants (IC50~24 μM) further supported its potential anti-inflammatory property. Greater electronic properties (topological polar surface area of 61.8) along with comparatively lesser docking parameters of the studied compound with aminoacyl residues of targeted enzymes (cyclooxygenase-2 and 5-lipoxygenase) (binding energy of 11.05 and 9.40 kcal mol^1, respectively) recognized its prospective anti-inflammatory potential. In an aim to develop seaweed-based natural anti-inflammatory leads, the present study isolated turbinochromanone as promising 5-lipoxygenase and cyclooxygenase-2 inhibitor, which could be used for pharmaceutical and biotechnological applications.

Item Type:	Article
Uncontrolled Keywords:	Turbinaria conoides; furanyl-substituted isochromanyl; turbinochromanone; 5-lipoxygenase; index of anti-inflammatory selectivity
Subjects:	Biochemistry Algae
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 2021 10:22
Last Modified:	27 Dec 2023 11:31
URI:	http://eprints.cmfri.org.in/id/eprint/15583

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