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<p>Oxyresveratrol is a naturally occurring phenolic compound found in various plant species, particularly in the heartwood of <i>Artocarpus lacucha</i>. There is a significant interest in oxyresveratrol due to its broad range of biological activities, including antioxidant, anti-inflammatory, anticancer and neuroprotective properties. It is well known that the introduction of fluorine can provide attractive opportunities in changing biological properties of a natural product. Accordingly, we synthesized fluorinated analogues of oxyresveratrol and evaluated their anticancer activity. By electrophilic fluorination with Selectfluor in the presence of nucleophiles, two new fluorinated compounds, i.e<i>.</i>, <i>anti</i>-1-[2-(3,5-dimethoxyphenyl)-2-fluoro-1-methoxy-ethyl]-2,4-dimethoxybenzene and <i>anti</i>-1-[2-(3,5-diacethoxyphenyl)-1,2-difluoro-ethyl]-2,4-diacetoxybenzene, were obtained in diastereomerically pure form. They exhibited up to ten-fold higher cytotoxicity against HepG2 cancer cells than the parent compound oxyresveratrol. Additionally, they displayed moderate activity against Caco-2 cancer cells, while oxyresveratrol and the common anticancer agent doxorubicin showed no cytotoxicity. These results indicate a beneficial effect of fluorination on the cytotoxicity of oxyresveratrol. Moreover, a wound-healing assay revealed that these fluorinated compounds displayed inhibition of the HepG2 cell migration.</p> Graphical abstract <p>Diastereomerically pure fluorinated derivatives of oxyresveratrol were synthesized for the first time via electrophilic fluorination using Selectfluor. These derivatives exhibited up to a tenfold increase in cytotoxicity against HepG2 and Caco-2 cancer cells compared with the parent compound, indicating that fluorine substitution enhances the cytotoxic potential of oxyresveratrol.</p>

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Synthesis of fluorinated analogues of oxyresveratrol and their cytotoxic activity against HepG2 and Caco-2 cancer cells

  • 期刊论文

  • 发表日期：

    2026年4月9日

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  • Nongnaphat Duangdee,
  • Natawadee Chamboonchu,
  • Boonwiset Seaho,
  • Wichayasith Inthakusol,
  • Wiratchanee Mahavorasirikul,
  • Wacharee Harnying,
  • Albrecht Berkessel,
  • Saisuree Prateeptongkum

摘要

Oxyresveratrol is a naturally occurring phenolic compound found in various plant species, particularly in the heartwood of Artocarpus lacucha. There is a significant interest in oxyresveratrol due to its broad range of biological activities, including antioxidant, anti-inflammatory, anticancer and neuroprotective properties. It is well known that the introduction of fluorine can provide attractive opportunities in changing biological properties of a natural product. Accordingly, we synthesized fluorinated analogues of oxyresveratrol and evaluated their anticancer activity. By electrophilic fluorination with Selectfluor in the presence of nucleophiles, two new fluorinated compounds, i.e., anti-1-[2-(3,5-dimethoxyphenyl)-2-fluoro-1-methoxy-ethyl]-2,4-dimethoxybenzene and anti-1-[2-(3,5-diacethoxyphenyl)-1,2-difluoro-ethyl]-2,4-diacetoxybenzene, were obtained in diastereomerically pure form. They exhibited up to ten-fold higher cytotoxicity against HepG2 cancer cells than the parent compound oxyresveratrol. Additionally, they displayed moderate activity against Caco-2 cancer cells, while oxyresveratrol and the common anticancer agent doxorubicin showed no cytotoxicity. These results indicate a beneficial effect of fluorination on the cytotoxicity of oxyresveratrol. Moreover, a wound-healing assay revealed that these fluorinated compounds displayed inhibition of the HepG2 cell migration.

Graphical abstract

Diastereomerically pure fluorinated derivatives of oxyresveratrol were synthesized for the first time via electrophilic fluorination using Selectfluor. These derivatives exhibited up to a tenfold increase in cytotoxicity against HepG2 and Caco-2 cancer cells compared with the parent compound, indicating that fluorine substitution enhances the cytotoxic potential of oxyresveratrol.