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Study on, Modification and Antitumor Activity of Resveratrol and γ-Mangostin Derivatives, Extraction and Purification of Saponin

Author: XiaoZhiBin
Tutor: LuYu
School: Nanchang University
Course: Biochemical Engineering
Keywords: Camellia saponin extraction Sephadex LH-20 resveratrol γ-mangostin derivatives synthetic anti-cancer acvitity
CLC: TQ423.2
Type: Master's thesis
Year: 2011
Downloads: 56
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Abstract


Camellia saponin obtained from out cake of camellia oleifera seeds, is a mixture of acylated oleanene-type pentacyclic triterpene oligoglycoside, composed by three parts, including theasaponin-genin, glucoside and organic acids.Researches at present shows that, it is an excellent non-ioin surface active agent,as well as many bioactivities,such as hemolytic activity, anti-permeability effect and diminishing inflammation, eliminating sputum to stop cough, easing pain, antibiotic capability anti-cancer and others, are widely used in building materials, daily chemical industry, pesticides and food industry.In this paper, extraction, purification, modification and antitumor activity of natural product have been studied. First, to purify total camellia saponin from seeds of camellia oleifera, macroporous adsorbent resins named as D4020, polymide resin, Sephadex LH-20 column chromatography were investigated one after another. Colorimetric method has been used to analysis the quantitative of total camellia saponin. Second, the natural extract of resveratrol andγ-mangostin as the raw material,5 derivatives were synthesized. The stuctures are confirmed by 1H NMR. Biological activity of synthetic compounds were investigated and the relationship between the chemical structure and antitumor activity on the basis is discussed. The main content are as follows:First, The recent progress of the biological activities, synthesis and strueture-activity relationship of resveratrol andγ-mangostin and their derivatives were reviewed extensively based on the detailed investigation of related literatures.Second, the optimum technological conditions for extracting saponin from Camellia oleifera Abel.are determined as follows:extraction temperature 60℃,the solid-liquid ratio 1:5,total extraction time 3h,and 70% ethanol as extraction solvent. Then, the total camellia saponin was purified through macroporous adsorbent resins named as D4020, polymide resin, Sephadex LH-20 column chromatography. And we investigated the effect of different solvents, flow rate and method of elution.Third, resveratrol and y-mangostin as the raw materials, according to their function group,5 kinds of derivatives were designed and synthesized. The two raw materials have hydroxyl guoups that have strong capacity for electronic, so the two raw materials have strong antioxidant activity, the 5 kinds of derivatives were obtained by modifying the hydroxyl groups.The structure of all compounds were confirmed by 1H NMR.Fourth, as contrast by adriamycin and tamoxifen, a primary anticancer activity of derivatives of resveratrol and y-mangostin were tested by MTT method in the first, and the structure-activity relationship was discussed.The compounds TY-1 has the best anti-tumor activety than others of derivatives of resveratrol against the MCF-7 and A549 cells line and the IC50 were 6.05 umol/L and 8.27umol/L.TY-2 is better anti-tumor activety than others of derivatives of resveratrol against the HepG2 cell line and the IC50 were 8.71 umol/L. The anti-tumor activety is not very well when the 2,3,6 hydroxyl group of y-mangostin were all substituted by benzyl groups. The structure-acvitity relationship show that the reservation of hydroxyl groups of resveratrol could help to enhance anti-cancer acvitity.

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CLC: > Industrial Technology > Chemical Industry > Reagents and the production of pure chemicals > Surfactant > Non-ionic surfactants
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