Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential
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...
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| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2021-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2021/9985604 |
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| author | Vy Anh Tran Thu-Thao Thi Vo My-Nuong Thi Nguyen Nguyen Duy Dat Van-Dat Doan Thanh-Quang Nguyen Quang Hieu Vu Van Thuan Le Thanh Danh Tong |
| author_facet | Vy Anh Tran Thu-Thao Thi Vo My-Nuong Thi Nguyen Nguyen Duy Dat Van-Dat Doan Thanh-Quang Nguyen Quang Hieu Vu Van Thuan Le Thanh Danh Tong |
| author_sort | Vy Anh Tran |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-2adf1c0024da422fb9b5a40ea0fa61cc |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2021-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-2adf1c0024da422fb9b5a40ea0fa61cc2025-08-20T03:54:42ZengWileyJournal of Chemistry2090-90632090-90712021-01-01202110.1155/2021/99856049985604Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer PotentialVy Anh Tran0Thu-Thao Thi Vo1My-Nuong Thi Nguyen2Nguyen Duy Dat3Van-Dat Doan4Thanh-Quang Nguyen5Quang Hieu Vu6Van Thuan Le7Thanh Danh Tong8Institute of Research and Development, Duy Tan University, Danang 550000, VietnamInstitute of Research and Development, Duy Tan University, Danang 550000, VietnamDepartment of Genetics, University of Science, Ho Chi Minh City, VietnamFaculty of Chemical & Food Technology, University of Technology and Education, Thu Duc, Ho Chi Minh City 700000, VietnamFaculty of Chemical Engineering, Industrial University of Ho Chi Minh City, 12 Nguyen Van Bao, Ho Chi Minh 700000, VietnamFaculty of Technology, Van Lang University, Ho Chi Minh City, VietnamNTT Hi-Tech Institute, Nguyen Tat Thanh University, 300A Nguyen Tat Thanh, Ward 13, District 4, Ho Chi Minh City, VietnamFaculty of Environmental and Chemical Engineering, Duy Tan University, Danang 550000, VietnamVietnam National University, Ho Chi Minh City, VietnamThe 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.http://dx.doi.org/10.1155/2021/9985604 |
| spellingShingle | Vy Anh Tran Thu-Thao Thi Vo My-Nuong Thi Nguyen Nguyen Duy Dat Van-Dat Doan Thanh-Quang Nguyen Quang Hieu Vu Van Thuan Le Thanh Danh Tong Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential Journal of Chemistry |
| title | Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential |
| title_full | Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential |
| title_fullStr | Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential |
| title_full_unstemmed | Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential |
| title_short | Novel α-Mangostin Derivatives from Mangosteen (Garcinia mangostana L.) Peel Extract with Antioxidant and Anticancer Potential |
| title_sort | novel α mangostin derivatives from mangosteen garcinia mangostana l peel extract with antioxidant and anticancer potential |
| url | http://dx.doi.org/10.1155/2021/9985604 |
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