2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation
Aquisinenins G–I (<b>1</b>–<b>3</b>), three new 2-(2-phenylethyl)chromone-sesquiterpene hybrids, were isolated from the ethanol extract of Hainan agarwood derived from <i>Aquilaria sinensis</i>. Spectroscopic techniques, such as <sup>1</sup>D and <s...
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2025-04-01
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| author | Guan-Hua Xu Ya-Li Wang Hao Wang Hui-Qin Chen Wen-Hua Dong Sheng-Zhuo Huang Cai-Hong Cai Jing-Zhe Yuan Wen-Li Mei Shou-Bai Liu Hao-Fu Dai |
| author_facet | Guan-Hua Xu Ya-Li Wang Hao Wang Hui-Qin Chen Wen-Hua Dong Sheng-Zhuo Huang Cai-Hong Cai Jing-Zhe Yuan Wen-Li Mei Shou-Bai Liu Hao-Fu Dai |
| author_sort | Guan-Hua Xu |
| collection | DOAJ |
| description | Aquisinenins G–I (<b>1</b>–<b>3</b>), three new 2-(2-phenylethyl)chromone-sesquiterpene hybrids, were isolated from the ethanol extract of Hainan agarwood derived from <i>Aquilaria sinensis</i>. Spectroscopic techniques, such as <sup>1</sup>D and <sup>2</sup>D NMR and HRESIMS, were used to determine their structures. Experimental and computed ECD data were compared to confirm their absolute configurations. Compounds <b>1</b>–<b>3</b> are uncommon dimeric derivatives of 2-(2-phenylethyl)chromone-sesquiterpene, characterized by the fusion of 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone with agarofuran or agarospirane-type sesquiterpene units by an ester linkage. Compound <b>1</b> inhibited nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells, showing an IC<sub>50</sub> value of 22.31 ± 0.42 μM. The neuroprotective effects of compounds <b>1</b> and <b>3</b> against H<sub>2</sub>O<sub>2</sub>-induced apoptosis were assessed in human neuroblastoma SH-SY5Y cells. Compound <b>1</b> demonstrated cytotoxicity with IC<sub>50</sub> values of 72.37 ± 0.20 μM against K562 and 61.47 ± 0.22 μM against BEL-7402, while compounds <b>2</b> and <b>3</b> showed cytotoxicity across all five tested human cancer cell lines. |
| format | Article |
| id | doaj-art-9503a4c01f6f4f73bfb89109df7526b7 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-9503a4c01f6f4f73bfb89109df7526b72025-08-20T03:52:57ZengMDPI AGMolecules1420-30492025-04-01309198410.3390/molecules300919842-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity EvaluationGuan-Hua Xu0Ya-Li Wang1Hao Wang2Hui-Qin Chen3Wen-Hua Dong4Sheng-Zhuo Huang5Cai-Hong Cai6Jing-Zhe Yuan7Wen-Li Mei8Shou-Bai Liu9Hao-Fu Dai10Key Laboratory of Genetics and Germplasm Innovation of Tropical Special Forest Trees and Ornamental Plants, Ministry of Education, College of Tropical Agriculture and Forestry, Hainan University, Danzhou 571737, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaKey Laboratory of Genetics and Germplasm Innovation of Tropical Special Forest Trees and Ornamental Plants, Ministry of Education, College of Tropical Agriculture and Forestry, Hainan University, Danzhou 571737, ChinaKey Laboratory of Natural Products Research and Development of Li Folk Medicine of Hainan Province, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaAquisinenins G–I (<b>1</b>–<b>3</b>), three new 2-(2-phenylethyl)chromone-sesquiterpene hybrids, were isolated from the ethanol extract of Hainan agarwood derived from <i>Aquilaria sinensis</i>. Spectroscopic techniques, such as <sup>1</sup>D and <sup>2</sup>D NMR and HRESIMS, were used to determine their structures. Experimental and computed ECD data were compared to confirm their absolute configurations. Compounds <b>1</b>–<b>3</b> are uncommon dimeric derivatives of 2-(2-phenylethyl)chromone-sesquiterpene, characterized by the fusion of 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone with agarofuran or agarospirane-type sesquiterpene units by an ester linkage. Compound <b>1</b> inhibited nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells, showing an IC<sub>50</sub> value of 22.31 ± 0.42 μM. The neuroprotective effects of compounds <b>1</b> and <b>3</b> against H<sub>2</sub>O<sub>2</sub>-induced apoptosis were assessed in human neuroblastoma SH-SY5Y cells. Compound <b>1</b> demonstrated cytotoxicity with IC<sub>50</sub> values of 72.37 ± 0.20 μM against K562 and 61.47 ± 0.22 μM against BEL-7402, while compounds <b>2</b> and <b>3</b> showed cytotoxicity across all five tested human cancer cell lines.https://www.mdpi.com/1420-3049/30/9/1984Hainan agarwood2-(2-phenylethyl)chromone-sesquiterpene hybridsstructure elucidationanti-inflammatory activityneuroprotective activitycytotoxic activity |
| spellingShingle | Guan-Hua Xu Ya-Li Wang Hao Wang Hui-Qin Chen Wen-Hua Dong Sheng-Zhuo Huang Cai-Hong Cai Jing-Zhe Yuan Wen-Li Mei Shou-Bai Liu Hao-Fu Dai 2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation Molecules Hainan agarwood 2-(2-phenylethyl)chromone-sesquiterpene hybrids structure elucidation anti-inflammatory activity neuroprotective activity cytotoxic activity |
| title | 2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation |
| title_full | 2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation |
| title_fullStr | 2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation |
| title_full_unstemmed | 2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation |
| title_short | 2-(2-Phenylethyl)chromone-Sesquiterpene Hybrids from Agarwood of <i>Aquilaria sinensis</i>: Characterization and Biological Activity Evaluation |
| title_sort | 2 2 phenylethyl chromone sesquiterpene hybrids from agarwood of i aquilaria sinensis i characterization and biological activity evaluation |
| topic | Hainan agarwood 2-(2-phenylethyl)chromone-sesquiterpene hybrids structure elucidation anti-inflammatory activity neuroprotective activity cytotoxic activity |
| url | https://www.mdpi.com/1420-3049/30/9/1984 |
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