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.Graphic
Highlights
The resinous heartwood of Aquilaria sinensis (Lour.)Spreng. (Thymelaeaceae) is known as agarwood
We reported several neuroprotective compounds from the resinous heartwood of A. sinensis with the origin in Guangdong, China
One hexahydrochromone and three sesquiterpenoids exert significant protective effects on rat adrenal pheochromocytoma (PC12) cell injury induced by corticosterone (CORT), while the hexahydrochromone and one sesquiterpenoid exhibit significant protective effects on 1-methyl-4-phenylpyridine ion ( MPP+)-induced
Summary
(Thymelaeaceae) is known as agarwood (chen-xiang in Chinese). Chen-xiang, a traditional Chinese medicine, is used to treat thoraco-abdominal distension and pain (xiongfu zhang-men teng-tong), vomiting and hiccups due to stomach cold (wei-han ou-tu e-ni), and asthma due to kidney deficiency (shen-xu qi-ni chuan-ji) [1]. We reported several neuroprotective compounds from the resinous heartwood of A. sinensis with the origin in Guangdong, China. All of these compounds from the plant are inactive against beta-site amyloid precursor protein cleaving enzyme 1 (BACE1) [5]. The isolation and structural elucidation of 17 compounds (1–17, Fig. 1), including four new compounds (1–4), from chen-xiang with the origin in Hainan, China, along with bioassay results in the models of CORT-induced and M. PP+-induced PC12 cell damage and BACE1 inhibition, are reported
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