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Bioactivity-Guided Separation of Potential D2 Dopamine Receptor Antagonists from Aurantii Fructus based on Molecular Docking Combined with High-Speed Counter-Current Chromatography

by Yingjie He 1,2,†, Shihao Zhu 1,2,†, Changqiao Wu 1,2, Ying Lu 1,2,* and Qi Tang 1,2,*
1
Hunan Key Laboratory of Traditional Chinese Veterinary Medicine, Hunan Agricultural University, Changsha 410128, China
2
Horticulture and Landscape College, Hunan Agricultural University, Changsha 410128, China
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2018, 23(12), 3135; https://doi.org/10.3390/molecules23123135
Received: 1 November 2018 / Revised: 26 November 2018 / Accepted: 28 November 2018 / Published: 29 November 2018
(This article belongs to the Section Natural Products Chemistry)
The typical compounds of Aurantii fructus (AF) reported in previous research were screened for their high antagonistic ability on the D2 dopamine receptor (D2R) in silico, and then bioactivity-guided separation was undertaken on the potential D2R antagonists from AF using high-speed counter-current chromatography (HSCCC). Three flavanones, two polymethoxyflavonoids, and three coumarins were effectively isolated from ethanol extracts of Aurantii fructus (AF) by the use of a two-step HSCCC method, and their chemical structures were identified by mass spectrometry, 1H-NMR, and 13C-NMR and compared with published data. Firstly, crude extract of 70% ethanol eluent (150 mg) was isolated by HSCCC using an n-hexane−ethyl acetate−n-butanol−methanol−0.05% acetic acid (1:3:1.8:1:5, v/v/v/v/v) solvent system, and compounds 1 (naringin, 28 mg), 2 (neohesperidin, 13 mg), 3 (meranzin, 5 mg) and 4 (poncirin, 3 mg) were successfully isolated with 98.5%, 95.1%, 97.7%, and 92.4% purity, respectively. Then, the crude extract of 95% ethanol eluent (120 mg) was isolated by n-hexane−n-butanol−ethanol (methanol)−0.05% acetic acid (2:0.6:1:3, v/v/v/v) solvent system and compounds 3 (meranzin, 3 mg), 5 (meranzin hydrate, 4 mg), 6 (isomeranzin, 6 mg), 7 (nobiletin, 10 mg), and 8 (tangeretin, 7 mg) were successfully isolated with 95.8%, 98.5%, 95.1%, 92.4%, and 97.7% purity, respectively. Naringenin, a parent structure of naringin with the excellent binding score of −9.3 kcal/mol, was completely in conjunction with the active site of D2R, indicating that it is critical for the treatment of gastrointestinal dysfunction. The results indicated that the bioactivity-guided method is practical for the effective separation of active compounds from natural resources. View Full-Text
Keywords: Aurantii fructus; molecular docking; high-speed counter-current chromatography; D2 dopamine receptor antagonists; naringenin Aurantii fructus; molecular docking; high-speed counter-current chromatography; D2 dopamine receptor antagonists; naringenin
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He, Y.; Zhu, S.; Wu, C.; Lu, Y.; Tang, Q. Bioactivity-Guided Separation of Potential D2 Dopamine Receptor Antagonists from Aurantii Fructus based on Molecular Docking Combined with High-Speed Counter-Current Chromatography. Molecules 2018, 23, 3135.

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