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Researchers isolated 17 new diterpenoids from Sandwithia guyanensis, with jatrointelone K showing moderate anti-chikungunya virus activity. This study expands knowledge of natural product diversity and potential antiviral agents.

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Virology

Background:

  • Chikungunya virus (CHIKV) poses a significant global health threat, necessitating the discovery of novel antiviral agents.
  • Natural products, particularly diterpenoids, are a rich source of diverse chemical structures with potential biological activities.
  • Sandwithia guyanensis is a plant species with unexplored chemical constituents.

Purpose of the Study:

  • To isolate and characterize new diterpenoids from Sandwithia guyanensis using bioassay-guided fractionation.
  • To evaluate the anti-CHIKV activity of the isolated compounds.
  • To investigate the structural diversity and biosynthetic relationships of novel diterpenoids.

Main Methods:

  • Bioassay-guided fractionation of an EtOAc extract of Sandwithia guyanensis trunk bark using a CHIKV-cell-based assay.
  • Structure elucidation of new compounds using comprehensive NMR spectroscopic data analysis.
  • Determination of relative and absolute configurations via single-crystal X-ray diffraction analysis.
  • Chemical transformation to support biosynthetic relationships.
  • Molecular networking-based dereplication of known compounds.

Main Results:

  • Seventeen new diterpenoids (1-17) were isolated, including novel tetranorditerpenoids, trinorditerpenoids, euphoractines, sikkimenoid E, and jatrointelones.
  • Jatrointelones J (14) and M (17) are the first naturally occurring C-15 nonoxidized lathyrane-type diterpenoids.
  • Jatrointelone K (15) exhibited moderate anti-CHIKV activity with an EC50 of 14 μM.
  • Biosynthetic relationships between jatrointelones and euphoractines were supported by chemical transformation.
  • Analogues of 12-O-tetradecanoylphorbol-13-acetate (TPA) were dereplicated.

Conclusions:

  • The study successfully identified a diverse array of novel diterpenoids from Sandwithia guyanensis.
  • Jatrointelone K represents a potential lead compound for further development of anti-CHIKV therapeutics.
  • The findings contribute to the understanding of diterpenoid structural diversity and biosynthesis.