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

Yue-Qiu He¹  Ping Yi²  Ji-Feng Luo³  Lu Zhang³  Xiao-Nian Li³  Meng-Yuan Xia³  Yue-Hu Wang³  Hui Yan³  Jun Yang³ 

[1] Faculty of Plant Protection, Yunnan Agricultural University;Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences;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, Kunming Institute of Botany, Chinese Academy of Sciences;

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

DOI  :  10.1007/s13659-022-00326-3

来源: DOAJ

【 摘 要 】

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

【 授权许可】

Unknown