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Natural scopoletin isolated from rubiaceous plants: a precursor for the synthesis of benzoylscopoletin and its cytotoxicity

biochemistry
biotechnology
plant-science

Abstract

Background: Scopoletin, a compound abundant in Rubiaceae such as Lasianthus lucidus and Morinda citrifolia, has demonstrated various activities, including antimicrobial activity, antinociceptive properties or pain relief and effects on cancer cell lines. Accordingly, it has significant potential as a precursor for synthetic bioactive agents for reducing pain, such as its derivative includes a benzene ring. However, very little has been reported regarding normal cellular effects or human skin irritation of such synthetic compounds, knowledge which is necessary if they are to be further developed. Thus, the aim of this study was to isolate scopoletin from Thai Rubiaceae, synthesize a derivative, and test its cytotoxicity.

Materials and Methods: Stem bark of L. lucidus and fruits of M. citrifolia were extracted, and the extract was partitioned into hydrophilic and lipophilic fractions. Lipophilic extracts were further fractionated by column chromatography and analysed by HPLC-DAD. Purified scopoletin was used for the synthesis of its benzoate derivative, and their structures were confirmed with the help of NMR spectroscopy. The cytotoxicity of the derivative compound was tested in the immortalized human keratinocyte HaCaT cell line.

Results: The lipophilic extracts displayed scopoletin contents of 16.14% and 13.94%, respectively. Scopoletin was completely converted to a target derivative, 6-methoxy-2-oxo-4a,8a-dihydro-2H-chromen-7-yl benzoate. This compound exhibited an IC50 value of 182.95 ± 6.15 µg/mL, with cell viability increased at concentrations less than 15.63 µg/mL but decreased at concentrations of 31.25 to 500 µg/mL.

Conclusions: We completely actualized both isolation and synthesis to achieve a high yield of the target scopoletin and benzoylscopoletin. This is the first cytotoxicity report of benzoylscopoletin in HaCaT cells, which supports further pharmaceutical product development. The analyses demonstrate reproducible isolation of scopoletin and synthesis of the derivative.

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