Antibacterial and antioxidant aryl-enclosed macrocyclic polyketide from intertidal macroalgae associated heterotrophic bacterium Shewanella algae

Vinaya, K K and Chakraborty, Kajal and Joy, Minju (2020) Antibacterial and antioxidant aryl-enclosed macrocyclic polyketide from intertidal macroalgae associated heterotrophic bacterium Shewanella algae. Medicinal Chemistry Research, 29. pp. 145-155.

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Abstract

Previously unreported aryl-enclosed 12-membered macrocyclic polyketide characterised as 2′-[(8-ethyl-8-methyl-2,5-dioxo-1-oxacyclododecanyl)methoxy]-methyl benzoate, was identified from the organic extract of Shewanella algae, a heterotrophic gamma proteobacterium, isolated from an intertidal marine macroalgae Hypnea valentiae. The titled macrocyclic polyketide displayed potential antibacterial activity (minimum inhibitory concentration 3.75 µg/mL) compared to that exhibited by chloramphenicol (6.25 µg/mL). Potent antioxidant activity of the studied compound was characterised by its greater scavenging effects on 2,2-diphenyl-1-picrylhydrazyl radical and 2,2′-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid (IC50 0.59 and 0.53 mg/mL, respectively) compared with standard, α-tocopherol (IC50 > 0.65 mg/mL). In silico molecular docking studies of the polyketide with the penicillin binding protein active sites encoded in methicillin resistant Staphylococcus aureus core genome displayed lesser binding energy of −10.31 kcal/mol, which could be correlated with its in vitro antibacterial activities. Structure-activity correlation studies demonstrated the direct relationship of electronic and optimum hydrophobic properties of the macrocyclic polyketide with its bioactivities. Therefore, the presently studied aryl-enclosed macrocyclic compound could be utilised as potent antioxidant and antibacterial pharmacophore in the medicinal formulations.

Item Type:	Article
Uncontrolled Keywords:	Shewanella algae; Heterotrophic gamma proteobacterium; Hypnea valentiae; Macrocyclic polyketide; Antibacterial activity; Structure-activity correlation studies
Subjects:	Biochemistry > Bioactive compounds 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:	13 Jan 2020 06:56
Last Modified:	13 Jan 2020 06:56
URI:	http://eprints.cmfri.org.in/id/eprint/14027

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