Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant
The ethyl ether extract of agarwood from an Aquilaria plant afforded six new sesquiterpenoids, Agarozizanol A − F (1−6), together with four known sesquiterpenoids and six known 2-(2-phenylethyl)chromones. Their structures were elucidated via detailed spectroscopic analysis, X-ray diffraction, and co...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2019-01-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | http://dx.doi.org/10.1080/14756366.2019.1576657 |
| _version_ | 1818574330395623424 |
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| author | Li Yang Yi-Ling Yang Wen-Hua Dong Wei Li Pei Wang Xue Cao Jing-Zhe Yuan Hui-Qin Chen Wen-Li Mei Hao-Fu Dai |
| author_facet | Li Yang Yi-Ling Yang Wen-Hua Dong Wei Li Pei Wang Xue Cao Jing-Zhe Yuan Hui-Qin Chen Wen-Li Mei Hao-Fu Dai |
| author_sort | Li Yang |
| collection | DOAJ |
| description | The ethyl ether extract of agarwood from an Aquilaria plant afforded six new sesquiterpenoids, Agarozizanol A − F (1−6), together with four known sesquiterpenoids and six known 2-(2-phenylethyl)chromones. Their structures were elucidated via detailed spectroscopic analysis, X-ray diffraction, and comparisons with the published data. All the isolates were evaluated for the α-glucosidase and tyrosinase inhibitory activities in vitro. Compounds 5, 7, 8, and 10 showed significant inhibition of α-glucosidase with IC50 values ranging between 112.3 ± 4.5 and 524.5 ± 2.7 µM (acarbose, 743. 4 ± 3.3 µM). Compounds 13 and 14 exhibited tyrosinase inhibitory effect with IC50 values of 89.0 ± 1.7 and 51.5 ± 0.6 µM, respectively (kojic acid, 46.1 ± 1.3). In the kinetic studies, compounds 5 and 14 were found to be uncompetitive inhibitors for α-glucosidase and mixed type inhibitors for tyrosinase, respectively. Furthermore, molecular docking simulations revealed the binding sites and interactions of the most active compounds with α-glucosidase and tyrosinase. |
| first_indexed | 2024-12-15T00:25:10Z |
| format | Article |
| id | doaj.art-a34bd049a1e949bd835f5644e989592d |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-12-15T00:25:10Z |
| publishDate | 2019-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-a34bd049a1e949bd835f5644e989592d2022-12-21T22:42:11ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742019-01-0134185386210.1080/14756366.2019.15766571576657Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plantLi Yang0Yi-Ling Yang1Wen-Hua Dong2Wei Li3Pei Wang4Xue Cao5Jing-Zhe Yuan6Hui-Qin Chen7Wen-Li Mei8Hao-Fu Dai9Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesInstitute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural SciencesThe ethyl ether extract of agarwood from an Aquilaria plant afforded six new sesquiterpenoids, Agarozizanol A − F (1−6), together with four known sesquiterpenoids and six known 2-(2-phenylethyl)chromones. Their structures were elucidated via detailed spectroscopic analysis, X-ray diffraction, and comparisons with the published data. All the isolates were evaluated for the α-glucosidase and tyrosinase inhibitory activities in vitro. Compounds 5, 7, 8, and 10 showed significant inhibition of α-glucosidase with IC50 values ranging between 112.3 ± 4.5 and 524.5 ± 2.7 µM (acarbose, 743. 4 ± 3.3 µM). Compounds 13 and 14 exhibited tyrosinase inhibitory effect with IC50 values of 89.0 ± 1.7 and 51.5 ± 0.6 µM, respectively (kojic acid, 46.1 ± 1.3). In the kinetic studies, compounds 5 and 14 were found to be uncompetitive inhibitors for α-glucosidase and mixed type inhibitors for tyrosinase, respectively. Furthermore, molecular docking simulations revealed the binding sites and interactions of the most active compounds with α-glucosidase and tyrosinase.http://dx.doi.org/10.1080/14756366.2019.1576657agarwoodaquilaria plantsesquiterpenoid2-(2-phenylethyl)chromoneα-glucosidase inhibitiontyrosinase inhibition |
| spellingShingle | Li Yang Yi-Ling Yang Wen-Hua Dong Wei Li Pei Wang Xue Cao Jing-Zhe Yuan Hui-Qin Chen Wen-Li Mei Hao-Fu Dai Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant Journal of Enzyme Inhibition and Medicinal Chemistry agarwood aquilaria plant sesquiterpenoid 2-(2-phenylethyl)chromone α-glucosidase inhibition tyrosinase inhibition |
| title | Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant |
| title_full | Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant |
| title_fullStr | Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant |
| title_full_unstemmed | Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant |
| title_short | Sesquiterpenoids and 2-(2-phenylethyl)chromones respectively acting as α-glucosidase and tyrosinase inhibitors from agarwood of an Aquilaria plant |
| title_sort | sesquiterpenoids and 2 2 phenylethyl chromones respectively acting as α glucosidase and tyrosinase inhibitors from agarwood of an aquilaria plant |
| topic | agarwood aquilaria plant sesquiterpenoid 2-(2-phenylethyl)chromone α-glucosidase inhibition tyrosinase inhibition |
| url | http://dx.doi.org/10.1080/14756366.2019.1576657 |
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