Oxaspiro Indiculides from Old Woman Octopus Cistopus indicus as Dual Inhibitors of Inducible Cyclooxygenase and Lipoxygenase

Silpa, K P and Chakraborty, Kajal (2022) Oxaspiro Indiculides from Old Woman Octopus Cistopus indicus as Dual Inhibitors of Inducible Cyclooxygenase and Lipoxygenase. Chemistry and Biodiversity. pp. 1-12.

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Abstract

The organic extract of the old woman octopus Cistopus indicus (Octopodidae), ubiquitous in the Central and South Indo-Pacific to the tropical Indian Ocean, was chromatographically fractionated over a reverse-phase adsorbent to yield two oxygenated spiro heterocyclic compounds, named indiculides A and B. Their structures were elucidated by using comprehensive spectroscopic methods. The radical scavenging potential displayed by indiculide A (IC50 ∼1.2 mM) besides attenuating the cyclooxygenase isoforms (COX-1/COX-2; IC50 3.36/3.02 μM) showed considerably superior activities when equated to those showed by indiculide B (IC50 3.45/3.22 μM). The inhibition property of indiculide A against 5-LOX (IC50 2.57 μM) was significantly greater than that of the standard 5-LOX inhibitor zileuton (IC50 3.70 μM, p<0.05). A greater selectivity index (anti-COX-1/anti-COX-2, 1.11) was perceived for indiculide A than that demonstrated by indiculide B (1.07) and anti-inflammatory drug diclofenac (0.96). Structure bio-activity relation study of indiculide A disclosed proportionality to the electronic properties besides permissible hydrophobicity-lipophilicity equilibrium, which could result in its efficient interface with the active site of inflammatory enzyme causing promising anti-inflammatory potential. Larger hydrogen bond networks of indiculide A on account of the more electronic-rich centers in conjunction with reduced docking factors reinforced its noteworthy attenuation potential against 5-LOX. The in vitro bioactivity assessment and in silico docking results were further validated by the superior drug-like characteristics of indiculide A (drug-likeness score, 0.21) than B analog, and therefore, the former metabolite could be a potential anti-inflammatory lead

Item Type:	Article
Uncontrolled Keywords:	Cistopus indicus; old woman octopus; octopodidae; oxaspiro indiculides A-B; anti-inflammatory activity
Subjects:	Biochemistry Molluscan Fisheries > Cephalopods
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:	12 Jul 2022 05:45
Last Modified:	12 Jul 2022 05:45
URI:	http://eprints.cmfri.org.in/id/eprint/16043

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