Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response
(±)-Hypersines A–C (<b>1</b>–<b>3</b>), the three pairs of enantiomerically pure monoterpenoid polyprenylated acylphloroglucinols with an unprecedented 6/6/5/4 fused ring system, were isolated from <i>Hypericum elodeoides</i>. Their structures, including absolute...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-10-01
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| Series: | Biomedicines |
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| Online Access: | https://www.mdpi.com/2227-9059/9/10/1473 |
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| author | Xiang-Zhong Liu Mi Zhou Chun-Chun Du Hong-Hong Zhu Xi Lu Shou-Lun He Guang-Hui Wang Ting Lin Wen-Jing Tian Hai-Feng Chen |
| author_facet | Xiang-Zhong Liu Mi Zhou Chun-Chun Du Hong-Hong Zhu Xi Lu Shou-Lun He Guang-Hui Wang Ting Lin Wen-Jing Tian Hai-Feng Chen |
| author_sort | Xiang-Zhong Liu |
| collection | DOAJ |
| description | (±)-Hypersines A–C (<b>1</b>–<b>3</b>), the three pairs of enantiomerically pure monoterpenoid polyprenylated acylphloroglucinols with an unprecedented 6/6/5/4 fused ring system, were isolated from <i>Hypericum elodeoides</i>. Their structures, including absolute configurations, were elucidated by comprehensive spectroscopic data, single-crystal X-ray diffraction, and quantum chemical calculations. The plausible, biosynthetic pathway of <b>1</b>–<b>3</b> was proposed. Moreover, the bioactivity evaluation indicated that <b>1a</b> might be a novel DNA damage response inhibitor, and could enhance MCF-7 cell sensitivity to the anticancer agent, camptothecin. |
| first_indexed | 2024-03-10T06:42:09Z |
| format | Article |
| id | doaj.art-1ce9ed445995477387859556503cd17c |
| institution | Directory Open Access Journal |
| issn | 2227-9059 |
| language | English |
| last_indexed | 2024-03-10T06:42:09Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomedicines |
| spelling | doaj.art-1ce9ed445995477387859556503cd17c2023-11-22T17:32:27ZengMDPI AGBiomedicines2227-90592021-10-01910147310.3390/biomedicines9101473Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage ResponseXiang-Zhong Liu0Mi Zhou1Chun-Chun Du2Hong-Hong Zhu3Xi Lu4Shou-Lun He5Guang-Hui Wang6Ting Lin7Wen-Jing Tian8Hai-Feng Chen9Fujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, ChinaFujian Provincial Key Laboratory of Innovative Drug Target, School of Pharmaceutical Sciences, Xiamen University, Xiamen 361102, China(±)-Hypersines A–C (<b>1</b>–<b>3</b>), the three pairs of enantiomerically pure monoterpenoid polyprenylated acylphloroglucinols with an unprecedented 6/6/5/4 fused ring system, were isolated from <i>Hypericum elodeoides</i>. Their structures, including absolute configurations, were elucidated by comprehensive spectroscopic data, single-crystal X-ray diffraction, and quantum chemical calculations. The plausible, biosynthetic pathway of <b>1</b>–<b>3</b> was proposed. Moreover, the bioactivity evaluation indicated that <b>1a</b> might be a novel DNA damage response inhibitor, and could enhance MCF-7 cell sensitivity to the anticancer agent, camptothecin.https://www.mdpi.com/2227-9059/9/10/1473Guttiferae<i>Hypericum elodeoides</i>acylphloroglucinolbiosynthetic pathwayDNA damage response inhibitor |
| spellingShingle | Xiang-Zhong Liu Mi Zhou Chun-Chun Du Hong-Hong Zhu Xi Lu Shou-Lun He Guang-Hui Wang Ting Lin Wen-Jing Tian Hai-Feng Chen Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response Biomedicines Guttiferae <i>Hypericum elodeoides</i> acylphloroglucinol biosynthetic pathway DNA damage response inhibitor |
| title | Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response |
| title_full | Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response |
| title_fullStr | Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response |
| title_full_unstemmed | Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response |
| title_short | Unprecedented Monoterpenoid Polyprenylated Acylphloroglucinols with a Rare 6/6/5/4 Tetracyclic Core, Enhanced MCF-7 Cells’ Sensitivity to Camptothecin by Inhibiting the DNA Damage Response |
| title_sort | unprecedented monoterpenoid polyprenylated acylphloroglucinols with a rare 6 6 5 4 tetracyclic core enhanced mcf 7 cells sensitivity to camptothecin by inhibiting the dna damage response |
| topic | Guttiferae <i>Hypericum elodeoides</i> acylphloroglucinol biosynthetic pathway DNA damage response inhibitor |
| url | https://www.mdpi.com/2227-9059/9/10/1473 |
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