Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China
Abstract Five new 2-(2-phenylethyl)chromone derivatives, (5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol (1), (5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol (2), (6S,7S,8R)-2‑[2‑(4-methoxyphenyl)ethyl]‑6,7,8‑trihydroxy‑5,6,7,8‑tetrahydrochromone (3), (6S,7S,8R)-2‑(2-phenylethyl)‑6,7,8‑trihydroxy‑5,6,7,8‑tetrahydro...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
SpringerOpen
2022-01-01
|
| Series: | Natural Products and Bioprospecting |
| Subjects: | |
| Online Access: | https://doi.org/10.1007/s13659-022-00326-3 |
| _version_ | 1828893076366557184 |
|---|---|
| author | Lu Zhang Ping Yi Hui Yan Xiao-Nian Li Meng-Yuan Xia Jun Yang Ji-Feng Luo Yue-Qiu He Yue-Hu Wang |
| author_facet | Lu Zhang Ping Yi Hui Yan Xiao-Nian Li Meng-Yuan Xia Jun Yang Ji-Feng Luo Yue-Qiu He Yue-Hu Wang |
| author_sort | Lu Zhang |
| collection | DOAJ |
| description | Abstract Five new 2-(2-phenylethyl)chromone derivatives, (5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol (1), (5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol (2), (6S,7S,8R)-2‑[2‑(4-methoxyphenyl)ethyl]‑6,7,8‑trihydroxy‑5,6,7,8‑tetrahydrochromone (3), (6S,7S,8R)-2‑(2-phenylethyl)‑6,7,8‑trihydroxy‑5,6,7,8‑tetrahydrochromone (4), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone (5), three new sesquiterpenoids, (4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (6), (4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (7), and (4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (8), along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) calculations. The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma (PC12) cell injury induced by corticosterone. At concentrations from 5 to 40 µM, compounds 4 and 6, agarotetrol (9), and 6-hydroxy-2-(2-phenylethyl)chromone (17) showed significant protective activities against corticosterone-induced PC12 cell injury (P < 0.001). Graphical Abstract |
| first_indexed | 2024-12-13T13:47:20Z |
| format | Article |
| id | doaj.art-db9c1be1752f483db605930a6dcb34c9 |
| institution | Directory Open Access Journal |
| issn | 2192-2195 2192-2209 |
| language | English |
| last_indexed | 2024-12-13T13:47:20Z |
| publishDate | 2022-01-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Natural Products and Bioprospecting |
| spelling | doaj.art-db9c1be1752f483db605930a6dcb34c92022-12-21T23:43:21ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092022-01-0112111410.1007/s13659-022-00326-3Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in ChinaLu Zhang0Ping Yi1Hui Yan2Xiao-Nian Li3Meng-Yuan Xia4Jun Yang5Ji-Feng Luo6Yue-Qiu He7Yue-Hu Wang8Key Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesKey Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of SciencesKey Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesKey Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesKey Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesKey Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesKey Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesFaculty of Plant Protection, Yunnan Agricultural UniversityKey Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of SciencesAbstract Five new 2-(2-phenylethyl)chromone derivatives, (5S,6R,7R,8S,7ʹR)-7ʹ-hydroxyagarotetrol (1), (5S,6R,7R,8S,7ʹS)-7ʹ-hydroxyagarotetrol (2), (6S,7S,8R)-2‑[2‑(4-methoxyphenyl)ethyl]‑6,7,8‑trihydroxy‑5,6,7,8‑tetrahydrochromone (3), (6S,7S,8R)-2‑(2-phenylethyl)‑6,7,8‑trihydroxy‑5,6,7,8‑tetrahydrochromone (4), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone (5), three new sesquiterpenoids, (4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (6), (4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (7), and (4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (8), along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) calculations. The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma (PC12) cell injury induced by corticosterone. At concentrations from 5 to 40 µM, compounds 4 and 6, agarotetrol (9), and 6-hydroxy-2-(2-phenylethyl)chromone (17) showed significant protective activities against corticosterone-induced PC12 cell injury (P < 0.001). Graphical Abstracthttps://doi.org/10.1007/s13659-022-00326-3ThymelaeaceaeAquilaria sinensisSesquiterpenoids2-(2-Phenylethyl)chromonesNeuroprotective |
| spellingShingle | Lu Zhang Ping Yi Hui Yan Xiao-Nian Li Meng-Yuan Xia Jun Yang Ji-Feng Luo Yue-Qiu He Yue-Hu Wang Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China Natural Products and Bioprospecting Thymelaeaceae Aquilaria sinensis Sesquiterpenoids 2-(2-Phenylethyl)chromones Neuroprotective |
| title | Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China |
| title_full | Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China |
| title_fullStr | Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China |
| title_full_unstemmed | Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China |
| title_short | Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China |
| title_sort | five new 2 2 phenylethyl chromone derivatives and three new sesquiterpenoids from the heartwood of aquilaria sinensis an aromatic medicine in china |
| topic | Thymelaeaceae Aquilaria sinensis Sesquiterpenoids 2-(2-Phenylethyl)chromones Neuroprotective |
| url | https://doi.org/10.1007/s13659-022-00326-3 |
| work_keys_str_mv | AT luzhang fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT pingyi fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT huiyan fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT xiaonianli fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT mengyuanxia fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT junyang fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT jifengluo fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT yueqiuhe fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina AT yuehuwang fivenew22phenylethylchromonederivativesandthreenewsesquiterpenoidsfromtheheartwoodofaquilariasinensisanaromaticmedicineinchina |