Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant
Nine new sesquiterpenoids (<b>1</b>–<b>9</b>) were isolated from ethyl ether extract of agarwood originated from <i>Aquilaria</i> sp., including three novel sesquiterpenoids (<b>1</b>–<b>3</b>) derived from zizaane, together with six zizaan...
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/1/198 |
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| author | Jing-Zhe Yuan Yi-Ling Yang Wei Li Li Yang Hao-Fu Dai Attila Mándi Cai-Hong Cai Hui-Qin Chen Wen-Hua Dong Tibor Kurtán Wen-Li Mei Hao Wang |
| author_facet | Jing-Zhe Yuan Yi-Ling Yang Wei Li Li Yang Hao-Fu Dai Attila Mándi Cai-Hong Cai Hui-Qin Chen Wen-Hua Dong Tibor Kurtán Wen-Li Mei Hao Wang |
| author_sort | Jing-Zhe Yuan |
| collection | DOAJ |
| description | Nine new sesquiterpenoids (<b>1</b>–<b>9</b>) were isolated from ethyl ether extract of agarwood originated from <i>Aquilaria</i> sp., including three novel sesquiterpenoids (<b>1</b>–<b>3</b>) derived from zizaane, together with six zizaane-type sesquiterpenoids (<b>4</b>–<b>9</b>). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound <b>9</b> exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC<sub>50</sub> value of 62.22 ± 1.27 μM. |
| first_indexed | 2024-03-10T03:29:54Z |
| format | Article |
| id | doaj.art-69e9cad8bfc94cfb81b0e6ae62a13631 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:29:54Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-69e9cad8bfc94cfb81b0e6ae62a136312023-11-23T11:58:10ZengMDPI AGMolecules1420-30492021-12-0127119810.3390/molecules27010198Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> PlantJing-Zhe Yuan0Yi-Ling Yang1Wei Li2Li Yang3Hao-Fu Dai4Attila Mándi5Cai-Hong Cai6Hui-Qin Chen7Wen-Hua Dong8Tibor Kurtán9Wen-Li Mei10Hao Wang11School of Life Sciences, Hainan University, Haikou 570228, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaDepartment of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaDepartment of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, HungaryHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaHainan Engineering Research Center of Agarwood, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, ChinaNine new sesquiterpenoids (<b>1</b>–<b>9</b>) were isolated from ethyl ether extract of agarwood originated from <i>Aquilaria</i> sp., including three novel sesquiterpenoids (<b>1</b>–<b>3</b>) derived from zizaane, together with six zizaane-type sesquiterpenoids (<b>4</b>–<b>9</b>). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound <b>9</b> exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC<sub>50</sub> value of 62.22 ± 1.27 μM.https://www.mdpi.com/1420-3049/27/1/198agarwood<i>Aquilaria</i> sp.sesquiterpenoidzizaaneTDDFT-ECDanti-inflammatory effect |
| spellingShingle | Jing-Zhe Yuan Yi-Ling Yang Wei Li Li Yang Hao-Fu Dai Attila Mándi Cai-Hong Cai Hui-Qin Chen Wen-Hua Dong Tibor Kurtán Wen-Li Mei Hao Wang Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant Molecules agarwood <i>Aquilaria</i> sp. sesquiterpenoid zizaane TDDFT-ECD anti-inflammatory effect |
| title | Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant |
| title_full | Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant |
| title_fullStr | Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant |
| title_full_unstemmed | Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant |
| title_short | Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an <i>Aquilaria</i> Plant |
| title_sort | zizaane type sesquiterpenoids and their rearranged derivatives from agarwood of an i aquilaria i plant |
| topic | agarwood <i>Aquilaria</i> sp. sesquiterpenoid zizaane TDDFT-ECD anti-inflammatory effect |
| url | https://www.mdpi.com/1420-3049/27/1/198 |
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