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Sesquiterpenoids and 2-(2-Phenylethyl)chromone Derivatives from the Resinous Heartwood of Aquilaria sinensis
Natural Products and Bioprospecting ( IF 4.8 ) Pub Date : 2021-06-01 , DOI: 10.1007/s13659-021-00313-0
Shu-Ya Wei 1, 2 , Dong-Bao Hu 3 , Meng-Yuan Xia 2 , Ji-Feng Luo 2 , Hui Yan 2 , Jing-Hua Yang 1 , Yun-Song Wang 1 , Yue-Hu Wang 2
Affiliation  

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 (517) 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



中文翻译:


沉香树脂心材中的倍半萜类化合物和 2-(2-苯乙基)色酮衍生物



一种新型螺内酯,沉香木内酯 ( 1 ),三种新型倍半萜类化合物,(2 R ,4 S ,5 R ,7 R )-2-羟基eremophila-9,11-dien-8-one ( 2 ),(1 R ,4 S , 5S , 7R , 11R )-13-羟基epidaphnauran-9-en-8-酮( 3 ),和( 4R , 5S , 7R , 8S , 10S , 13R )-8,13 -diHydroxyrotunda-1,11-dien-3-one ( 4 ) 以及 13 种已知化合物 ( 517 ) 从白木香(瑞香科)的树脂心材中分离出来。基于NMR和MS数据分析以及ECD谱的理论计算,阐明了新化合物的结构。评估了分离的化合物对皮质酮 (CORT) 和 1-甲基-4-苯基吡啶离子 (MPP + ) 诱导的 PC12 细胞损伤的保护活性,以及​​对 BACE1 的抑制活性。化合物4、5,6-二羟基-2-(2-苯基乙基)色酮( 5 )、瑞香醇B( 7 )、6-甲氧基-2-[2-(3-甲氧基苯基)乙基]色酮( 10 )、异琼脂四醇( 14 )和1-羟基-1,5-二苯基戊-3-酮( 16 )在20μM浓度下对CORT诱导的PC12细胞损伤具有显着的保护作用( P < 0.001)。浓度为 20 μM 的异琼脂四醇 ( 14 ) 对 MPP +诱导的 PC12 细胞损伤显示出显着的保护作用 ( P < 0.001),而化合物4显示出中等活性 ( P < 0.01)。 所有测试化合物的 BACE1 抑制活性都很弱,浓度为 20 μM 时抑制率低于 30%。

 图文摘要

更新日期:2021-06-01
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