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

  • Vinaya Kizhakkepatt Kizhakkekalam
  • Kajal ChakrabortyEmail author
  • Minju Joy
Original Research


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.


Shewanella algae Heterotrophic gamma proteobacterium Hypnea valentiae Macrocyclic polyketide Antibacterial activity Structure-activity correlation studies 



This work was supported by funding under Kerala State Council for Science, Technology and Environment (Grant No. 040/FSHP-LSS/2014/KSCSTE). The authors are thankful to Indian Council of Agricultural Research, New Delhi for providing facilities to carry out the work. The authors thank the Director, Central Marine Fisheries Research Institute and Dean, Faculty of Marine Sciences, Lakeside Campus, Cochin University of Science and Technology for support. Thanks are due to the Head, Marine Biotechnology Division, Central Marine Fisheries Research Institute for facilitating the research activities.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2019_2468_MOESM1_ESM.doc (15.9 mb)
Supplementary Information


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Central Marine Fisheries Research InstituteCochinIndia
  2. 2.Faculty of Marine Sciences, Lakeside CampusCochin University of Science and TechnologyCochinIndia

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