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

Natural Products and Bioprospecting

Yue-Hu Wang¹  Ji-Feng Luo¹  Meng-Yuan Xia¹  Hui Yan¹  Jing-Hua Yang²  Yun-Song Wang²  Shu-Ya Wei³  Dong-Bao Hu⁴ 

[1] 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, 650201, Kunming, People’s Republic of China;Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, School of Pharmacy, Yunnan University, 650091, Kunming, People’s Republic of China;Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, School of Pharmacy, Yunnan University, 650091, Kunming, People’s Republic of China;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, 650201, Kunming, People’s Republic of China;School of Chemical Biology and Environment, Yuxi Normal University, 653100, Yuxi, People’s Republic of China;

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

DOI  :  10.1007/s13659-021-00313-0

来源: Springer

【 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.Graphic Abstract

【 授权许可】

CC BY