A new alkaloid and a new benzaldehyde derivative from the twig of Zanthoxylum rhetsa (Roxb.) DC.

Abstract

A new alkaloid, 2-acetyl-4-methoxyfuro[2,3-b]quinoline (1), and a new benzaldehyde derivative, (2′S)-4-(2′-hydroxy-3′-methyl-3′-butenoxy)benzaldehyde (2), were isolated from the twig of Zanthoxylum rhetsa (Roxb.) DC. along with twenty-six known compounds (3−28). Their structures were determined by spectroscopic analysis (1D and 2D NMR spectroscopy and HRMS analysis) and comparison with data reported in the literature. Thirteen of the known compounds were evaluated for their cytotoxic activities against human cancer cell lines that included MDA-MB-231, SW1353, A549, and HCT116. (±)-8-Acetonyldihydronitidine (15) showed moderate cytotoxicity toward the SW1353 cancer cell line with an IC₅₀ value of 18.90±0.39 µg/mL, and exhibited weak cytotoxic activity against MDA-MB-231, A549 and HCT116 cell lines with IC₅₀ values of 49.86−71.32 µg/mL.

Keywords:

• Zanthoxylum rhetsa
• alkaloid
• benzaldehyde derivative
• cytotoxicity

Acknowledgments

The Graduate School, the Division of Physical Science, Faculty of Science, Prince of Songkla University and the Natural Product Research Center of Excellence are acknowledged for partial support. The authors would like to thank the Faculty of Science, Prince of Songkla University for NMR analysis, the Scientific Equipment Center, Prince of Songkla University for the MS analysis and Mr. Thomas Duncan Coyne for his assistance with the English text.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported from the Center of Excellence for Innovation in Chemistry (PERCH-CIC) and National Research Council of Thailand (Grant No. N41A640071).