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Phytochemical and Primary Biological Research on Three Medicinal Plants

Author: HeZhengChun
Tutor: PanYuanJiang
School: Zhejiang University
Course: Organic Chemistry
Keywords: Lysimachia parvifolia Frahoh Leycesteria formosa Wall Citrusmedica L. var. sarcodactylis Hort polysaccharide structural elucidation cytotoxicity immunological activity
CLC: R284
Type: PhD thesis
Year: 2014
Downloads: 137
Quote: 0
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Abstract


Since1960s, with the successful development of some herbal medicines, it has been one hot research field for most chemists to find drug or leading compounds from natural plants. China is a country rich in natural plant resources and parts of them have been used in traditional Chinese medicine for a long history. As a multi-ethnic country, various ethnodrugs were developed and enriched the medicinal plant resources. However, little information on their chemical components is known for most of them. So it is believed that analysis and identification of chemical components in these plants is not only necessary but also important for the development of traditional Chinese medicines.This paper was composed of five sections, contents including extraction, isolation and identification of chemical components from three medicinal plants. Two of them were mainly focused on the small molecules and their cytotoxicities. The other plant was focused on its macromolecule constituents (polysaccharide) and their immunological activities.Phytochemical studies on Lysimachia Parvifolia Frahoh and Leycesteria formosa Wall were carried out using modern chromatographic methods, leading to the isolation of22and22compounds respectively. Their structures were elucidated on the basis of chemical analysis, ESI-MS, IR, GC-MS,1D/2D NMR spectra.41of them were identified and5of them were newly reported compounds, and they are elucidated as follows:13β-28-epoxy-3β,22a,23-trihydroxyolean-16-one (C30H48O5);13β-28-epoxy-22a,23-dihydroxyolean-3,16-dione(C3oH4605); anagalligenone-3-O-α-L-arabinopyranoside(C35H56O8); anagalligenone-3-O-[β-D-glucopyranosyl(1→4)-α-L-arabinopyranoside](C41H66013); anagalligenone-3-O-[β-D-xylopyranosyl(1→2)-β-D-glucopyranosyl(1→4)-α-L-arabinopyranoside](C46H74O17).According to the structural features of obtained compounds and the reports on the bioactivities of this type compound,25compounds were selected in evaluation of cytotoxicities in vitro on six human cancer cell lines, using conventional drug-sensitivity screening method (MTT). The results showed that some of them have strong cytotoxic activities on all tested cell lines. Considering the results, the most powerful compound10and GepG2cell lines were selected for possible mechanism exploration. Annexin-V/PI double staining was used for flow cytometry (FCM) to evaluate the apoptosis, and PI and DAPI staining were used for morphology observation. The results showed that compound10was acting on cell membrane to destroy the cytoskeleton in a short time, lead to break of cell membrane and cytoplasm flowed out, finally caused the cell necrosis.Four water-soluble polysaccharides, FCp-1, FCp-2, FCp-3and FCp-4were obtained from finger citron fruits (Citrus medica L. var. sarcodactylis) by hot-water extraction and ethanol precipitation, followed by conventional separation procedure. Based on the calibration curve, molecular weights of them were estimated to be113.9,32.6,140.3and177.1kDa respectively. The acid hydrolysis, methylation, IR, GC-MS and NMR experiments were used for composition analysis. FCp-1was a heteropolysaccharide composed of arabinose, galactose, glucose, rhamnose and xylose, with a molar ratio of3.0:7.0:4.1:1.0:1.5. FCp-2and FCp-4were→4)-α-D-GalpA(1→linking galacturonan differ in molecular weights. FCp-3was a→6)-α-D-Glcp(1→linking glucan. According to the results of in vitro assays, FCp-3showed significantly and moderately enhancing capacities towards the proliferation of splenocytes and thymocytes respectively. Thus, FCp-3or analogs may have potential application as immunomodulatory agents.

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