白藜芦醇与γ-倒捻子素的结构改造和抗肿瘤活性及油茶皂苷的提取、纯化的研究
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摘要
油茶皂苷是从油茶饼粕中提取出来的五环三萜类混合物,其结构是由皂苷配基、糖体和有机酸三部分组成。研究表明：油茶皂苷是一种性能优良的非离子型天然表面活性剂,并具有溶血性、抗渗消炎、化痰止咳、镇痛、抗菌、抗癌等许多生物活性,广泛应用于建材、日用化工、农药行业及食品工业。
本文致力于天然产物的提取分离与结构改造及其生物活性的研究。首先探讨了油茶粕中油茶皂苷的提取分离工艺,对现有的油茶皂苷分离提取工艺进行改进,提出了先后使用大孔树脂,聚酰胺树脂及Sephadex LH-20凝胶柱进行分离,并使用比色法对产品进行测定,得到了较纯的油茶皂苷产品。其次,我们以天然提取的白藜芦醇及γ-倒捻子素为原料,对其结构进行修饰改造,合成了5个化合物,用1H NMR对其进行了结构表征。将合成的新化合物进行抗肿瘤生物活性试验的研究,在此基础上讨论了化合物与抗肿瘤活性之间的构效关系。本论文的主要研究内容归纳为如下几个方面：
1.在查阅了大量文献的基础上,全面系统的归纳了油茶皂苷的提取分离工艺及白藜芦醇与γ-倒捻子素及其衍生物的研究现状和其药理活性。
2.以江西产的油茶粕为原料,用70%乙醇,料液比1：5(w/v),在60℃下浸提3h,将提取出的油茶皂苷粗品经大孔树脂,聚酰胺树脂及Sephadex LH-20凝胶柱进行分离。并探讨了溶剂、流速、不同洗脱方案等分别对大孔树脂,聚酰胺树脂及Sephadex LH-20凝胶柱分离纯化油茶皂苷的影响。
3.分别以白藜芦醇和γ-倒捻子素为母体,根据其官能团特点,设计合成了4个白藜芦醇的衍生物及1个γ-倒捻子素衍生物。由于白藜芦醇和γ-倒捻子素的酚羟基具有很强的供电子能力,这可能是其具有抗氧化能力的主要原因,于是对其上的酚羟基进行结构修饰,合成的新化合物分别通过1HNMR分别确定了它们的结构。
4.以阿霉素和他莫西芬为对照物,采用MTT法对白藜芦醇及γ-倒捻子素衍生物抗肿瘤活性进行首次测试。实验结果表明：对比于其它的白藜芦醇衍生物,化合物TY-1对肿瘤细胞MCF-7和A549的抗癌活性最佳,IC50值分别是6.05umol/L和8.27umol/L,化合物TY-2对HepG2癌细胞株抗癌效果最好,它IC50值是8.71umol/L。对γ-倒捻子素衍生物,当γ-倒捻子素的2,3,6位上的酚羟基上的氢全部被苄基取代时,其生物活性不显著。
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.
本文致力于天然产物的提取分离与结构改造及其生物活性的研究。首先探讨了油茶粕中油茶皂苷的提取分离工艺,对现有的油茶皂苷分离提取工艺进行改进,提出了先后使用大孔树脂,聚酰胺树脂及Sephadex LH-20凝胶柱进行分离,并使用比色法对产品进行测定,得到了较纯的油茶皂苷产品。其次,我们以天然提取的白藜芦醇及γ-倒捻子素为原料,对其结构进行修饰改造,合成了5个化合物,用1H NMR对其进行了结构表征。将合成的新化合物进行抗肿瘤生物活性试验的研究,在此基础上讨论了化合物与抗肿瘤活性之间的构效关系。本论文的主要研究内容归纳为如下几个方面：
1.在查阅了大量文献的基础上,全面系统的归纳了油茶皂苷的提取分离工艺及白藜芦醇与γ-倒捻子素及其衍生物的研究现状和其药理活性。
2.以江西产的油茶粕为原料,用70%乙醇,料液比1：5(w/v),在60℃下浸提3h,将提取出的油茶皂苷粗品经大孔树脂,聚酰胺树脂及Sephadex LH-20凝胶柱进行分离。并探讨了溶剂、流速、不同洗脱方案等分别对大孔树脂,聚酰胺树脂及Sephadex LH-20凝胶柱分离纯化油茶皂苷的影响。
3.分别以白藜芦醇和γ-倒捻子素为母体,根据其官能团特点,设计合成了4个白藜芦醇的衍生物及1个γ-倒捻子素衍生物。由于白藜芦醇和γ-倒捻子素的酚羟基具有很强的供电子能力,这可能是其具有抗氧化能力的主要原因,于是对其上的酚羟基进行结构修饰,合成的新化合物分别通过1HNMR分别确定了它们的结构。
4.以阿霉素和他莫西芬为对照物,采用MTT法对白藜芦醇及γ-倒捻子素衍生物抗肿瘤活性进行首次测试。实验结果表明：对比于其它的白藜芦醇衍生物,化合物TY-1对肿瘤细胞MCF-7和A549的抗癌活性最佳,IC50值分别是6.05umol/L和8.27umol/L,化合物TY-2对HepG2癌细胞株抗癌效果最好,它IC50值是8.71umol/L。对γ-倒捻子素衍生物,当γ-倒捻子素的2,3,6位上的酚羟基上的氢全部被苄基取代时,其生物活性不显著。
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.
引文
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