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Xenicanes attenuate pro-inflammatory 5-lipoxygenase: Prospective natural anti-inflammatory leads from intertidal brown seaweed Padina tetrastromatica

  • Tima Antony
  • Kajal ChakrabortyEmail author
Original Research
  • 22 Downloads

Abstract

Two previously unreported xenicane class of novaxenicin-type xenicin diterpenoids (12) bearing cyclonona[d]furo [2,3-b]pyrandiol and three xeniolide-type diterpenoids with unprecedented octahydrocyclonona[c]pyran-3(1H)-one backbones (35) were separated from the organic extract of the intertidal seaweed Padina tetrastomatica (family Dictyotaceae), collected from southern India. The compounds were deduced to bear a xenicane moiety with a 2-oxabicyclo[7.4.0]tridecane cyclic system. The structures of these specialized metabolites were attributed based on the extensive nuclear magnetic resonance spectral analyses, and comparison of related compounds. Xeniolide-type diterpenes (3–5) registered significantly greater attenuation potential against pro-inflammatory 5-lipoxygenase (IC50 ~ 2.04 mM) than that exhibited by non-steroidal anti-inflammatory drug ibuprofen (IC50 4.50 mM, P< 0.05). The xeniolide derivative octahydro-1,7-dihydroxy-4-(41-hydroxy-42-methylpropyl)-6-(61-hydroxy-62-propenyl)-10-methyl-cyclonona[c]pyran-3(1H)-one (5) exhibited comparable antioxidant activity (DPPH IC50 1.73 mM) along with standard antioxidative agent α-tocopherol (IC50 < 2 mM). In silico molecular modelling studies were performed to designate the 5-lipoxygenase inhibitory mechanism of the xenicanes, and the comparison of docking parameters suggested that the xeniolide derivative 5 exhibited least binding energy of −11.56 kcal mol−1, and that was corroborated with its greater inhibition potential against the pro-inflammatory enzyme. These results demonstrated that the xeniolide-type diterpenoids with previously unreported δ-lactone cyclononane framework might constitute promising anti-inflammatory leads with pro-inflammatory 5-lipoxygenase enzyme inhibitory activities.

Keywords

Padina tetrastromatica Xenicane-type diterpenoids Xenicins Xeniolides Anti-inflammatory 5-Lipoxygenase enzyme inhibitory 

Notes

Acknowledgements

The present work was supported by Science and Engineering Research Board (SERB) (grant number SR/S1/OC-96A/2012) of Department of Science and Technology, New Delhi, India. The authors thank the Director, Indian Council of Agricultural Research-Central Marine Fisheries Research Institute (ICAR-CMFRI), and Head, Marine Biotechnology Division, ICAR-CMFRI for guidance and support.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Supplementary material

44_2019_2322_MOESM1_ESM.doc (4.3 mb)
Supplementary information.

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Copyright information

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

Authors and Affiliations

  1. 1.Marine Bioprospecting Section of Marine Biotechnology DivisionCentral Marine Fisheries Research InstituteCochinIndia
  2. 2.Department of ChemistryMangalore UniversityMangalagangothriIndia

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