Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis

doi:10.1007/s13659-021-00313-0

应用天然产物 ›› 2021, Vol. 11 ›› Issue (5): 545-555.DOI: 10.1007/s13659-021-00313-0

• ORIGINAL ARTICLES • 上一篇下一篇

Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis

Shu-Ya Wei^1,2, Dong-Bao Hu³, Meng-Yuan Xia², Ji-Feng Luo², Hui Yan², Jing-Hua Yang¹, Yun-Song Wang¹, Yue-Hu Wang²

1 Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, School of Pharmacy, Yunnan University, Kunming 650091, People's Republic of China;
2 Key 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, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
3 School of Chemical Biology and Environment, Yuxi Normal University, Yuxi 653100, People's Republic of China

收稿日期:2021-04-08 出版日期:2021-10-24 发布日期:2021-09-27
通讯作者: Yun-Song Wang, Yue-Hu Wang
基金资助:
This study was supported by the National Natural Science Foundation of China (nos. 31960480, 81960629, 21662040, and 21462048) and the Joint Special Project of Local Undergraduate Universities in Yunnan Province, China (no. 2018FH001-024).

Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis

Shu-Ya Wei^1,2, Dong-Bao Hu³, Meng-Yuan Xia², Ji-Feng Luo², Hui Yan², Jing-Hua Yang¹, Yun-Song Wang¹, Yue-Hu Wang²

1 Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, School of Pharmacy, Yunnan University, Kunming 650091, People's Republic of China;
2 Key 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, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
3 School of Chemical Biology and Environment, Yuxi Normal University, Yuxi 653100, People's Republic of China

Received:2021-04-08 Online:2021-10-24 Published:2021-09-27
Contact: Yun-Song Wang, Yue-Hu Wang
Supported by:
This study was supported by the National Natural Science Foundation of China (nos. 31960480, 81960629, 21662040, and 21462048) and the Joint Special Project of Local Undergraduate Universities in Yunnan Province, China (no. 2018FH001-024).

摘要/Abstract

摘要： One novel spirolactone, aquilarisinolide (1), three new sesquiterpenoids, (2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one (2), (1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one (3), and (4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one (4), together with 13 known compounds (5-17) were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra. The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone (CORT) and 1-methyl-4-phenylpyridine ion (MPP⁺), as well as inhibitory activities against BACE1. Compound 4, 5,6-dihydroxy-2-(2-phenylethyl) chromone (5), daphnauranol B (7), 6-methoxy-2-[2-(3-methyoxyphenyl) ethyl]chromone (10), isoagarotetrol (14), and 1-hydroxy-1,5-diphenylpentan-3-one (16) showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20 μM (P < 0.001). Isoagarotetrol (14) showed a significant protective effect on MPP⁺-induced injury in PC12 cells at a concentration of 20 μM (P < 0.001), while compound 4 showed a moderate activity (P < 0.01). The BACE1-inhibitory activities of all tested compounds were very weak with less than 30% inhibition at a concentration of 20 μM.

关键词: Thymelaeaceae, Aquilaria sinensis, Sesquiterpenoids, 2-(2-phenylethyl) chromones, Neuroprotective

Abstract: One novel spirolactone, aquilarisinolide (1), three new sesquiterpenoids, (2R,4S,5R,7R)-2-hydroxyeremophila-9,11-dien-8-one (2), (1R,4S,5S,7R,11R)-13-hydroxyepidaphnauran-9-en-8-one (3), and (4R,5S,7R,8S,10S,13R)-8,13-dihydroxyrotunda-1,11-dien-3-one (4), together with 13 known compounds (5-17) were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The structures of the new compounds were elucidated based on the analysis of NMR and MS data and theoretical calculations their ECD spectra. The isolated compounds were evaluated for their protective activities against PC12 cell injury induced by corticosterone (CORT) and 1-methyl-4-phenylpyridine ion (MPP⁺), as well as inhibitory activities against BACE1. Compound 4, 5,6-dihydroxy-2-(2-phenylethyl) chromone (5), daphnauranol B (7), 6-methoxy-2-[2-(3-methyoxyphenyl) ethyl]chromone (10), isoagarotetrol (14), and 1-hydroxy-1,5-diphenylpentan-3-one (16) showed significant protective effects on CORT-induced injury in PC12 cells at a concentration of 20 μM (P < 0.001). Isoagarotetrol (14) showed a significant protective effect on MPP⁺-induced injury in PC12 cells at a concentration of 20 μM (P < 0.001), while compound 4 showed a moderate activity (P < 0.01). The BACE1-inhibitory activities of all tested compounds were very weak with less than 30% inhibition at a concentration of 20 μM.

Key words: Thymelaeaceae, Aquilaria sinensis, Sesquiterpenoids, 2-(2-phenylethyl) chromones, Neuroprotective

Shu-Ya Wei, Dong-Bao Hu, Meng-Yuan Xia, Ji-Feng Luo, Hui Yan, Jing-Hua Yang, Yun-Song Wang, Yue-Hu Wang. Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis[J]. 应用天然产物, 2021, 11(5): 545-555.

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Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis

Sesquiterpenoids and 2-(2-Phenylethyl) chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis

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