Abstract
The mangosteen peels contain biologically active compounds, with antioxidant and anticancer properties. Among these isolated phytochemicals, α-mangostin is one of the most powerful natural antioxidants and anticancer compounds. This study focused on synthesizing novel α-mangostin (α-MG) derivatives at positions of C-3 and C-6 from extracted α-MG of mangosteen peels and investigating antioxidant and anticancer activities. The structures of the synthesized compounds were determined by using MS, 1H-NMR, 13C-NMR, and HPLC. The analysis of the interaction between structure and bioactivity showed that phenol groups on C-3 and C-6 positions play a crucial role in antiproliferative activity to boost both anticancer efficacy and drug-like properties. The antioxidant activity of α-MG and its derivatives were investigated by the DPPH method. Among α-MG derivatives, 1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-3,6-diyl bis(2-bromobenzoate) (compound 4) exhibited significant antioxidant property. The in vitro cytotoxicity against various cancer cell lines (HeLa, MCF-7, NCI–H460, and HepG2) was evaluated by the standard sulforhodamine B assay. The anticancer activities (HeLa, MCF-7, NCI–H460, and HepG2) of compound 4 are five to six times higher than those of α-MG and other derivatives. The acetylation at C-3 and C-6 of α-MG by halogen of benzoyl greatly improved cancer cell toxicity. Our results provide new opportunities for further explorations of α-MG derivatives for antioxidant property and promise as drugs in cancer therapy.
Highlights
Nowadays, the study of natural phytochemical substances from plants has continuously increased due to their effectiveness in preventing and treating various human diseases [1,2,3,4]. ese natural substances are an excellent alternative for therapeutic due to abundant resources, low cost, high biocompatibility, nontoxicity to the human body, and high biological and pharmacological activity
To improve the antioxidant and anticancer activities of α-MG, a series of new compounds were designed and synthesized from the pristine α-MG by simultaneously changing the substituents OH group on the C-3 and C-6 of α-MG by F−, Cl−, and Br− of benzoyl chloride. α-MG derivatives structures were determined using Mass Spectrometry (MS), 1H-NMR, 13C-NMR, and High-Performance Liquid Chromatography (HPLC). e antioxidant activity of α-MG and its derivatives were investigated by the DPPH method. e effects of cytotoxicity of the synthesized compounds were studied on four cancer cell lines (HeLa, MCF-7, NCI–H460, and HepG2)
Ese studies suggest that C-3 and C-6 phenol groups are critical to inhibiting cancer cell lines and increase the activity of drug-like properties [51,52,53]
Summary
The study of natural phytochemical substances from plants has continuously increased due to their effectiveness in preventing and treating various human diseases [1,2,3,4]. ese natural substances are an excellent alternative for therapeutic due to abundant resources, low cost, high biocompatibility, nontoxicity to the human body, and high biological and pharmacological activity. The study of natural phytochemical substances from plants has continuously increased due to their effectiveness in preventing and treating various human diseases [1,2,3,4]. Various parts of plants, including roots, stems, leaves, fruits, flowers, and seeds, can be used as sources for the extraction of natural bioactive compounds [5,6,7,8,9]. The mangosteen peels have been utilized extensively in traditional medicine for treating several illnesses, including skin infection, dysentery, trauma, abdominal pain, and wound infection, as well as cancer treatment [20,21,22]
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