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Bioassay-Guided Isolation and Identification of Cytotoxic Compounds from Melaleuca quinquenervia Fruits. 2024

Achara Raksat, and Md Samiul Huq Atanu, and Sheyanne Mendez, and Rafael de la Zerda, and Rui Sun, and Sarot Cheenpracha, and Marisa Wall, and Charles J Simmons, and Philip G Williams, and Ghee T Tan, and Supakit Wongwiwatthananukit, and Leng Chee Chang
Department of Pharmaceutical Sciences, The Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, Hawaii 96720, United States.

The fruit extract of Melaleuca quinquenervia yielded a total of 19 compounds, including two novel spiro-biflavonoid enantiomers (1a and 1b) and a chalcone derivative (3). Their structures were determined through spectroscopic analysis. The enantiomers of the racemic mixture of compound 1 were successfully resolved into (+)-1 and (-)-1 using chiral-phase HPLC. Single-crystal X-ray diffraction analysis was also used to confirm the structure of 1. The enantiomeric configurations of 1 and 2 were determined through a comparison of the calculated and experimental electronic circular dichroism spectra. Compounds 2 (melanervin), 14 (methyl betulinate), 15 (3-O-acetylbetulinic acid), and 16 (pyracrenic acid) were found to be highly cytotoxic, with compound 16 showing superior growth inhibition of nonsmall cell lung cancer cells (A549 cells) (IC50 2.8 ± 0.1 μM) compared to cisplatin (IC50 3.3 ± 0.0 μM), a positive control chemotherapeutic drug. Both compound 16 and cisplatin were significantly more cytotoxic toward A549 lung cancer cells compared to nontumorigenic Vero E6 cells.

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