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.

[img] Text
Kajal Chakraborty_2020_Medicinal Chemistry Research_Antibacterial and antioxidant aryl-enclosed macrocyclic polyketide from intertidal macroalgae associated heterotrophic bacterium Shewanella algae.pdf
Restricted to Registered users only

Download (1MB) | Request a copy
Official URL: https://link.springer.com/article/10.1007/s00044-0...
Related URLs:

    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
    Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI-Kochi > Marine Biotechnology
    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

    Actions (login required)

    View Item View Item