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Styryllactones from Goniothalamus tamirensis.

Pornphimol Meesakul1, Wuttichai Jaidee2, Christopher Richardson3

  • 1Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Science, Mae Fah Luang University, Chiang Rai, 57100, Thailand; School of Chemistry and Molecular Bioscience, University of Wollongong, Wollongong, New South Wales, 2522, Australia.

Phytochemistry
|January 10, 2020
PubMed
Summary

Phytochemical analysis of Goniothalamus tamirensis yielded 15 compounds, including novel styryllactones. (-)-5-Acetoxygoniothalamin showed potent cytotoxicity against colon cancer cells, outperforming doxorubicin.

Keywords:
AnnonaceaeCytotoxicityGoniothalamus tamirensisStyryllactoneStyryllactone dimer

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Area of Science:

  • Natural Product Chemistry
  • Medicinal Chemistry
  • Organic Chemistry

Background:

  • Goniothalamus tamirensis is a plant species with potential medicinal properties.
  • Phytochemical investigations are crucial for discovering new bioactive compounds.

Purpose of the Study:

  • To isolate and identify compounds from Goniothalamus tamirensis extracts.
  • To evaluate the cytotoxic activity of isolated compounds against cancer cell lines.

Main Methods:

  • Phytochemical analysis of plant extracts using spectroscopic methods (NMR, MS).
  • Chemical synthesis of Goniotamirenone A via [2+2] cycloaddition.
  • Determination of absolute configurations using ECD data and X-ray crystallography.
  • Cytotoxicity assays (IC50) against HCT116 colon cancer cells.

Main Results:

  • Fifteen compounds were isolated, including three new styryllactones (goniotamirenones A-C) and two new natural products.
  • (-)-5-Acetoxygoniothalamin demonstrated significant cytotoxicity (IC50 = 8.6 μM) against HCT116 cells, exceeding doxorubicin's activity (IC50 = 9.7 μM).
  • (Z)-6-Styryl-5,6-dihydro-2-pyranone showed moderate activity (IC50 = 22.1 μM).

Conclusions:

  • Goniothalamus tamirensis is a source of novel styryllactones with potential anticancer properties.
  • (-)-5-Acetoxygoniothalamin is a promising candidate for further development as an anticancer agent.
  • Structural elucidation and synthesis of these compounds advance natural product chemistry.