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Open AccessArticle

Compositions, Formation Mechanism, and Neuroprotective Effect of Compound Precipitation from the Traditional Chinese Prescription Huang-Lian-Jie-Du-Tang

1
School of Chinese Pharmacy, Beijing University of Chinese Medicine, Beijing 100102, China
2
Institute of Medicinal Plant Development, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100193, China
3
Department of Pathology, Beijing University of Chinese Medicine, Beijing 100102, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2016, 21(8), 1094; https://doi.org/10.3390/molecules21081094
Received: 30 June 2016 / Revised: 26 July 2016 / Accepted: 1 August 2016 / Published: 19 August 2016
(This article belongs to the Section Natural Products Chemistry)
Compounds in the form of precipitation (CFP) are universally formed during the decocting of Chinese prescriptions, such as Huang-Lian-Jie-Du-Tang (HLJDT). The formation rate of HLJDT CFP even reached 2.63% ± 0.20%. The identification by liquid chromatography mass spectrometry (LC-MSn) proved that the main chemical substances of HLJDT CFP are baicalin and berberine, which is coincident with the theory that the CFP might derive from interaction between acidic and basic compounds. To investigate the formation mechanism of HLJDT CFP, baicalin and berberine were selected to synthesize a simulated precipitation and then the baicalin–berberine complex was obtained. Results indicated that the melting point of the complex interposed between baicalin and berberine, and the UV absorption, was different from the mother material. In addition, 1H-NMR integral and high-resolution mass spectroscopy (HR-MS) can validate that the binding ratio was 1:1. Compared with baicalin, the chemical shifts of H and C on glucuronide had undergone significant changes by 1H-, 13C-NMR, which proved that electron transfer occurred between the carboxylic proton and the lone pair of electrons on the N atom. Both HLJDT CFP and the baicalin–berberine complex showed protective effects against cobalt chloride-induced neurotoxicity in differentiated PC12 cells. It is a novel idea, studying the material foundation of CFP in Chinese prescriptions. View Full-Text
Keywords: compounds in the form of precipitation; Huang-Lian-Jie-Du-Tang; material foundation; baicalin–berberine complex; formation mechanism; neuroprotective effect compounds in the form of precipitation; Huang-Lian-Jie-Du-Tang; material foundation; baicalin–berberine complex; formation mechanism; neuroprotective effect
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MDPI and ACS Style

Zhang, C.; Zhao, R.; Yan, W.; Wang, H.; Jia, M.; Zhu, N.; Zhu, Y.; Zhang, Y.; Wang, P.; Lei, H. Compositions, Formation Mechanism, and Neuroprotective Effect of Compound Precipitation from the Traditional Chinese Prescription Huang-Lian-Jie-Du-Tang. Molecules 2016, 21, 1094.

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