新疆一枝蒿体外抗肿瘤物质基础及制备工艺研究
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摘要
一枝蒿(Artemisia rupestris L.)为菊科(Compositae)蒿属岩蒿植物,以全草入药,是维吾尔医常用药材。因它唯独生长在中国新疆境内的天山、阿尔泰山和昆仑山山脉,海拔1600～4500米的森林草原带地区,并在新疆民间沿用已久,故名新疆一枝蒿。自古以来新疆流传着“家有一枝蒿不怕毒蛇咬”和“家有一枝蒿,百病都除掉”的谚语。维吾尔药志中记载它有祛风活血、散瘀消肿、健胃消食、清热解毒、抗过敏、解蛇毒等功效。其化学成分主要含有黄酮类、酮酸类、萜类、多糖类、挥发油、多肽和生物碱类化合物。目前临床上广泛将其用于抗感冒病毒方面,而新疆学者对一枝蒿的研究也多集中在抗感冒病毒和抗乙肝病毒方面。鉴于在对一枝蒿药理作用的深入研究中发现一枝蒿黄酮类成分具有诱导肿瘤细胞分化,对肿瘤细胞的增殖及DNA的合成有明显的抑制作用,但其确切的抗肿瘤活性部位和起作用的物质基础尚未明确。为了了解一枝蒿中抗肿瘤活性物质基础,开拓其应用范围,进一步开发这一传统维吾尔药材,我们对一枝蒿体外抗肿瘤活性部位、活性化学成分、制备工艺及质量控制方法方面进行了研究探讨。
目的:1)确定一枝蒿体外抗肿瘤活性部位及其主要活性成分。2)优选一枝蒿活性部位的制备工艺。3)建立一枝蒿活性部位的质量控制方法。
方法:1)在进行文献调研的基础上,采用生物活性跟踪手段,对新疆一枝蒿不同提取溶剂下得到的提取物及通过大孔吸附树脂不同乙醇浓度洗脱下得到的洗脱物进行了体外抗HL-60人白血病瘤株、BGC-823人胃癌瘤株、Bel-7402人肝癌瘤株、KB人鼻咽癌瘤株的活性实验筛选,并首次采用多种纯化分离方法(大孔吸附树脂、硅胶柱层析、聚酰胺柱层析、Sephadex LH-20柱层析)和结构鉴定技术(UV、IR、EI-MS、1HNMR、13CNMR、DEPT、HMQC、HMBC等波谱学技术和化学方法)对筛选出的活性部位化学成分进行了系统研究。同时首次运用电喷雾电离技术对从一枝蒿中提取分离得到的紫花牡荆素的结构和质谱裂解机制进行研究,并完整地分析了其主要的特征碎片离子和该化合物的裂解途径。2)以活性部位中化学成分为优选指标,采用单因素试验与多因素试验相结合的方法,首次对一枝蒿活性部位提取工艺和纯化工艺进行了研究。3)通过方法学考察建立了活性部位及其药材的质量控制方法。
结果:1)新疆一枝蒿水提取物以70%乙醇洗脱物能明显的抑制上述四种瘤株细胞生长,提示具有良好的体外抗肿瘤效果,可能为抗肿瘤所在的活性部位,同时从70%乙醇洗脱物中分离得到了16个单体化合物,通过理化性质分析和波谱解析鉴定了13个化合物,这些化合物中8个为首次从该植物中分离得到,其中2个为首次从该属植物中分离得到。其中黄酮类化合物8个,倍半萜类2个,甾类2个,其他1个。同时发现紫花牡荆素主要通过C环、A环的碎裂而发生裂解,出现碎片m/z 375、342、314、299、285、271以及碎片m/z 375又裂解成碎片m/z 342,碎片m/z 342又裂解成碎片m/z 314,碎片m/z 314又裂解成碎片m/z 299,碎片m/z 299又裂解成碎片m/z 285或271为ESI-MS裂解特征。由此可初步推断黄酮类化合物ESI-MS裂解规律同样遵循EI-MS裂解规律。2)经过提取工艺筛选、大孔树脂纯化工艺筛选及提取纯化工艺3批验证,最后确定一枝蒿活性部位提取工艺路线为:以水为一枝蒿药材的提取溶剂,提取3次,每次30分钟,第1次加水量为14倍,第2次加水量为14倍,第3次加水量为14倍,趁热过滤,合并提取液,减压回收溶剂,冷冻干燥得一枝蒿水提取物;纯化工艺条件为:一枝蒿水提取物用HPD-450型树脂纯化,上样浓度为30 mg/ml,原液(pH=6)上样,吸附流速为2 ml/min,树脂柱径高比1∶9,上样量与树脂体积比1∶15。以2倍树脂体积的蒸馏水清洗树脂柱后,用70%乙醇洗脱,吸脱剂用量为6倍量树脂体积,洗脱流速为2 ml/min。树脂经95%乙醇和1mol/L NaOH再生后,可重复使用7次。3)首次建立了一枝蒿活性部位及一枝蒿药材中同时测定槲皮素、木犀草素、山奈酚和紫花牡荆素的高效液相色谱方法。
结论:1)活性部位的确定及活性成分的分离为进一步开发研究一枝蒿奠定了药效物质基础。同时对紫花牡荆素的结构以及裂解途径的解析为进一步研究黄酮类化合物的代谢与结构修饰提供了参考依据。2)3批样品的制备和含量测定结果表明一枝蒿活性部位提取纯化工艺合理,稳定。提取物得率10.36～11.98%,总黄酮含量50%以上(51.29%～53.95%),符合要求。主要有效成分木犀草素和紫花牡荆素的含量分别为9.77%～9.84%、23.77%～24.16%,基本稳定且符合要求。同时体外药效学实验表明3批活性部位制备样品的体外药理活性与活性实验筛选用的70%乙醇洗脱物的活性无统计学差别,说明优选出的制备工艺取得了预期的结果。3)3批一枝蒿活性部位样品及3批药材中四种黄酮类成分的含量测定结果表明,建立的诸方法操作简便,精密度和重复性良好,回收率合格,测定结果准确,可作为一枝蒿活性部位及其药材的质量控制方法。为进一步进行创新药物的开发研制,制订科学、合理、严格的质量控制标准和评价体系奠定了基础。
Artemisia rupestris L., which is widely used by Uyghur native people, belongs to the genus Artemisia of family Compositae. It only grows in Xinjiang region of China, especially in the regions of Tian-shan mountains, A-ertai mountains and Kun-lun mountains, distributing widely at an altitude of 1600~4500 m and grows on grassy areas of subalpine and in needle-leaved forests, so it was named Xinjiang Artemisia rupestris. In ancient, a folk saying of“Where there is Artemisia rupestris L., Where there is no toxin of sankes.”and“Where there is Artemisia rupestris L., Where there is no disease.”is widespread in Xinjiang. It was recorded in“The Uyghur Traditional Medicine RecordsⅠ”and some clinical data indicated that Artemisia rupestris L. has pharmacological activities such as dispelling wind and promoting blood flow, removing blood stasis and relieving swelling, strengthening the stomach to promote digestion, clearing away heat and toxins, anti-anaphylaxis and relieving toxins of snakes. It was reported that Artemisia rupestris L. contains mainly chemical constituents such as flavonoids, keto-acid oxoacid, terpenoids, polysaccharides, volatile oil, polypeptide and alkaloids. Nowadays, researching of Artemisia rupestris L. was focused on anti- influenza and anti-hepatitis B virus by scientists in Xinjiang. Lately, it was reported that flavonoids of Artemisia rupestris L. could exert their anti-proliferative effects on human liver tumor cell through inducing apoptosis and/or toxicity. In order to clarify the anti-tumor components, extend the clinical effects and further develop the traditional Uyghur resources, we carried out systematical investigation of active parts, active components of anti-tumor in vitro, preparative technology and the methods of quality control of the active part of Artemisia rupestris L.
Objectives: 1) To screen the active parts and active constituents of anti-tumor in vitro of Artemisia rupestris L. 2) To optimize the preparative technology of the active part of Artemisia rupestris L. 3) To establish the methods of quality control of the active part of Artemisia rupestris L..
Methods: 1) On the basis of systematical consulting the researching literatures of chemical constituents and biological activities study on the genus Artemisia plants, by means of bioactivity-guiding, anti-tumor activity screening assay of four-tumor cell lines in vitro were made on water extract, 95% ethanol extract, chloroform extract of Artemisia rupestris L. and water eluant, 30% ethanol eluant, 50% ethanol eluant, 70% ethanol eluant, 90% ethanol eluant by HPD-450 macroporous absorption resin, and the chemical constituents of the active part of Artemisia rupestris L. were researched for the first time. Several purification and separation methods (column chromatography on macroporous absorption resin, silical gel, polyamide, Sephadex LH-20) and many kinds of structure elucidation and identification technologies (UV, IR, EI-MS, 1H- NMR, 13C-NMR, DEPT, HMQC and HMBC) were used. And structure and MS/MS fragment pathway of casticin obtained from active part of Artemisia rupestris L. were elucidated with electron spray ionization mass spectrometry for the first time. The characteristic ions and fragment mechanism were explained. 2) According to the mono factor design and multifactors design, we used the contents of the mainly active constituents as index to select the extraction technology and purification technology of the active part of Artemisia rupestris L. for the first time. 3) The methods of quality control of the active part were established after the methodology validation.
Results: 1) 70% ethanol eluant from water extract showed promising inhibitory tumor effects on the tested tumor cell lines and suggest that 70% ethanol eluant might be active part of anti-tumor in vitro, and 16 compounds were isolated from the 70% ethanol eluant of Artemisia rupestris L. and 13 compounds were elucidated on the basis of the physico-chemical properties and spectra analysis. Among them, 8 compounds were isolated from the plant for the first time and 2 compounds was isolated from the genus Artemisia for the first time. And among them, 8 compounds belong to flavonoids, 2 sesquiterpenes, 2 sterols and 1 other. And the results also showed that casticin mainly fragmented on the C ring and A ring. The characteristic ions of casticin were m/z 375, 342, 314, 299, 285 or 271 and m/z 375 fragment to m/z 342, ion m/z 342 fragment to m/z 314, ion m/z 314 fragment to m/z 299, ion m/z 299 fragment to m/z 285 or 271. And it was preliminaryly deduced that ESI-MS fragment pathway of flavonoids is similar to EI-MS fragment pathway of flavonoids. 2) After optimizing of the extraction technology and purification technology of the active part and verified through 3 batches of samples, the extraction technology of the active part was as following: the extracting solvent was pure water, extracting 3 times, first added 14 times extracting solvent to the materials, second added 14 times extracting solvent to the materials and third added 14 times extracting solvent to the materials and the extracting lasted 30 minutes each time. The purification technology of the active part was as following: water extract of Artemisia rupestris L. (the concentration of original solution of the extract was 30 mg/ml, pH=6) was subjected to HPD-450 resin column (diameter/high=1:9) with the adsorbing current velocity 2 ml/min, the ratio of loading capacity to resin volume was 1:15. After eluted with water (twice of resin volumn), the resin was eluted by 70% ethanol with 6 times of resin volumn under the flow rate 2 ml/min. The resin could be used for 7 times repeatedly after regenerated with 95% ethanol and 1 mol/L NaOH. 3) For the first time, the quantitative methods of mainly active constituents, such as quercetin, luteolin, kaempferol and casticin in Artemisia rupestris L. extract and Artemisia rupestris L. were established by HPLC.
Conclusions: 1) The study of active parts and active constituents provided a substance basis of actions for further developing Artemisia rupestris L. And providing important information for flavonoids metabolism and structural modification researching on MS/MS fragment pathway of casticin. 2) The extraction and purification technology of Artemisia rupestris L. was reasonable, steady and repetitive. The yield ratio of Artemisia rupestris L. extract was 10.36~11.98%. The contents of total flavonoids was over 50% (51.29~53.95%) which met the demands. The mainly active constituents of luteolin and casticin were 9.77~9.84% and 23.77~24.16%, respectively. These results were steady and satisfied. The results of principle pharmacodynamics in vitro showed that the active part was as same as the 70% ethanol eluant screened assay in vitro in the first part, so it indicated that optimizing the preparative technology of the active part obtained anticipated result. 3) 3 batches of samples showed that established methods were easy and accurate, had nice recovery rates and good repetition, and could be used to control the quality of Artemisia rupestris L. extract and Artemisia rupestris L. which provided a basis for developing a novel drug and establishing its scientific, reasonable and strict quality control system in the future.
目的:1)确定一枝蒿体外抗肿瘤活性部位及其主要活性成分。2)优选一枝蒿活性部位的制备工艺。3)建立一枝蒿活性部位的质量控制方法。
方法:1)在进行文献调研的基础上,采用生物活性跟踪手段,对新疆一枝蒿不同提取溶剂下得到的提取物及通过大孔吸附树脂不同乙醇浓度洗脱下得到的洗脱物进行了体外抗HL-60人白血病瘤株、BGC-823人胃癌瘤株、Bel-7402人肝癌瘤株、KB人鼻咽癌瘤株的活性实验筛选,并首次采用多种纯化分离方法(大孔吸附树脂、硅胶柱层析、聚酰胺柱层析、Sephadex LH-20柱层析)和结构鉴定技术(UV、IR、EI-MS、1HNMR、13CNMR、DEPT、HMQC、HMBC等波谱学技术和化学方法)对筛选出的活性部位化学成分进行了系统研究。同时首次运用电喷雾电离技术对从一枝蒿中提取分离得到的紫花牡荆素的结构和质谱裂解机制进行研究,并完整地分析了其主要的特征碎片离子和该化合物的裂解途径。2)以活性部位中化学成分为优选指标,采用单因素试验与多因素试验相结合的方法,首次对一枝蒿活性部位提取工艺和纯化工艺进行了研究。3)通过方法学考察建立了活性部位及其药材的质量控制方法。
结果:1)新疆一枝蒿水提取物以70%乙醇洗脱物能明显的抑制上述四种瘤株细胞生长,提示具有良好的体外抗肿瘤效果,可能为抗肿瘤所在的活性部位,同时从70%乙醇洗脱物中分离得到了16个单体化合物,通过理化性质分析和波谱解析鉴定了13个化合物,这些化合物中8个为首次从该植物中分离得到,其中2个为首次从该属植物中分离得到。其中黄酮类化合物8个,倍半萜类2个,甾类2个,其他1个。同时发现紫花牡荆素主要通过C环、A环的碎裂而发生裂解,出现碎片m/z 375、342、314、299、285、271以及碎片m/z 375又裂解成碎片m/z 342,碎片m/z 342又裂解成碎片m/z 314,碎片m/z 314又裂解成碎片m/z 299,碎片m/z 299又裂解成碎片m/z 285或271为ESI-MS裂解特征。由此可初步推断黄酮类化合物ESI-MS裂解规律同样遵循EI-MS裂解规律。2)经过提取工艺筛选、大孔树脂纯化工艺筛选及提取纯化工艺3批验证,最后确定一枝蒿活性部位提取工艺路线为:以水为一枝蒿药材的提取溶剂,提取3次,每次30分钟,第1次加水量为14倍,第2次加水量为14倍,第3次加水量为14倍,趁热过滤,合并提取液,减压回收溶剂,冷冻干燥得一枝蒿水提取物;纯化工艺条件为:一枝蒿水提取物用HPD-450型树脂纯化,上样浓度为30 mg/ml,原液(pH=6)上样,吸附流速为2 ml/min,树脂柱径高比1∶9,上样量与树脂体积比1∶15。以2倍树脂体积的蒸馏水清洗树脂柱后,用70%乙醇洗脱,吸脱剂用量为6倍量树脂体积,洗脱流速为2 ml/min。树脂经95%乙醇和1mol/L NaOH再生后,可重复使用7次。3)首次建立了一枝蒿活性部位及一枝蒿药材中同时测定槲皮素、木犀草素、山奈酚和紫花牡荆素的高效液相色谱方法。
结论:1)活性部位的确定及活性成分的分离为进一步开发研究一枝蒿奠定了药效物质基础。同时对紫花牡荆素的结构以及裂解途径的解析为进一步研究黄酮类化合物的代谢与结构修饰提供了参考依据。2)3批样品的制备和含量测定结果表明一枝蒿活性部位提取纯化工艺合理,稳定。提取物得率10.36～11.98%,总黄酮含量50%以上(51.29%～53.95%),符合要求。主要有效成分木犀草素和紫花牡荆素的含量分别为9.77%～9.84%、23.77%～24.16%,基本稳定且符合要求。同时体外药效学实验表明3批活性部位制备样品的体外药理活性与活性实验筛选用的70%乙醇洗脱物的活性无统计学差别,说明优选出的制备工艺取得了预期的结果。3)3批一枝蒿活性部位样品及3批药材中四种黄酮类成分的含量测定结果表明,建立的诸方法操作简便,精密度和重复性良好,回收率合格,测定结果准确,可作为一枝蒿活性部位及其药材的质量控制方法。为进一步进行创新药物的开发研制,制订科学、合理、严格的质量控制标准和评价体系奠定了基础。
Artemisia rupestris L., which is widely used by Uyghur native people, belongs to the genus Artemisia of family Compositae. It only grows in Xinjiang region of China, especially in the regions of Tian-shan mountains, A-ertai mountains and Kun-lun mountains, distributing widely at an altitude of 1600~4500 m and grows on grassy areas of subalpine and in needle-leaved forests, so it was named Xinjiang Artemisia rupestris. In ancient, a folk saying of“Where there is Artemisia rupestris L., Where there is no toxin of sankes.”and“Where there is Artemisia rupestris L., Where there is no disease.”is widespread in Xinjiang. It was recorded in“The Uyghur Traditional Medicine RecordsⅠ”and some clinical data indicated that Artemisia rupestris L. has pharmacological activities such as dispelling wind and promoting blood flow, removing blood stasis and relieving swelling, strengthening the stomach to promote digestion, clearing away heat and toxins, anti-anaphylaxis and relieving toxins of snakes. It was reported that Artemisia rupestris L. contains mainly chemical constituents such as flavonoids, keto-acid oxoacid, terpenoids, polysaccharides, volatile oil, polypeptide and alkaloids. Nowadays, researching of Artemisia rupestris L. was focused on anti- influenza and anti-hepatitis B virus by scientists in Xinjiang. Lately, it was reported that flavonoids of Artemisia rupestris L. could exert their anti-proliferative effects on human liver tumor cell through inducing apoptosis and/or toxicity. In order to clarify the anti-tumor components, extend the clinical effects and further develop the traditional Uyghur resources, we carried out systematical investigation of active parts, active components of anti-tumor in vitro, preparative technology and the methods of quality control of the active part of Artemisia rupestris L.
Objectives: 1) To screen the active parts and active constituents of anti-tumor in vitro of Artemisia rupestris L. 2) To optimize the preparative technology of the active part of Artemisia rupestris L. 3) To establish the methods of quality control of the active part of Artemisia rupestris L..
Methods: 1) On the basis of systematical consulting the researching literatures of chemical constituents and biological activities study on the genus Artemisia plants, by means of bioactivity-guiding, anti-tumor activity screening assay of four-tumor cell lines in vitro were made on water extract, 95% ethanol extract, chloroform extract of Artemisia rupestris L. and water eluant, 30% ethanol eluant, 50% ethanol eluant, 70% ethanol eluant, 90% ethanol eluant by HPD-450 macroporous absorption resin, and the chemical constituents of the active part of Artemisia rupestris L. were researched for the first time. Several purification and separation methods (column chromatography on macroporous absorption resin, silical gel, polyamide, Sephadex LH-20) and many kinds of structure elucidation and identification technologies (UV, IR, EI-MS, 1H- NMR, 13C-NMR, DEPT, HMQC and HMBC) were used. And structure and MS/MS fragment pathway of casticin obtained from active part of Artemisia rupestris L. were elucidated with electron spray ionization mass spectrometry for the first time. The characteristic ions and fragment mechanism were explained. 2) According to the mono factor design and multifactors design, we used the contents of the mainly active constituents as index to select the extraction technology and purification technology of the active part of Artemisia rupestris L. for the first time. 3) The methods of quality control of the active part were established after the methodology validation.
Results: 1) 70% ethanol eluant from water extract showed promising inhibitory tumor effects on the tested tumor cell lines and suggest that 70% ethanol eluant might be active part of anti-tumor in vitro, and 16 compounds were isolated from the 70% ethanol eluant of Artemisia rupestris L. and 13 compounds were elucidated on the basis of the physico-chemical properties and spectra analysis. Among them, 8 compounds were isolated from the plant for the first time and 2 compounds was isolated from the genus Artemisia for the first time. And among them, 8 compounds belong to flavonoids, 2 sesquiterpenes, 2 sterols and 1 other. And the results also showed that casticin mainly fragmented on the C ring and A ring. The characteristic ions of casticin were m/z 375, 342, 314, 299, 285 or 271 and m/z 375 fragment to m/z 342, ion m/z 342 fragment to m/z 314, ion m/z 314 fragment to m/z 299, ion m/z 299 fragment to m/z 285 or 271. And it was preliminaryly deduced that ESI-MS fragment pathway of flavonoids is similar to EI-MS fragment pathway of flavonoids. 2) After optimizing of the extraction technology and purification technology of the active part and verified through 3 batches of samples, the extraction technology of the active part was as following: the extracting solvent was pure water, extracting 3 times, first added 14 times extracting solvent to the materials, second added 14 times extracting solvent to the materials and third added 14 times extracting solvent to the materials and the extracting lasted 30 minutes each time. The purification technology of the active part was as following: water extract of Artemisia rupestris L. (the concentration of original solution of the extract was 30 mg/ml, pH=6) was subjected to HPD-450 resin column (diameter/high=1:9) with the adsorbing current velocity 2 ml/min, the ratio of loading capacity to resin volume was 1:15. After eluted with water (twice of resin volumn), the resin was eluted by 70% ethanol with 6 times of resin volumn under the flow rate 2 ml/min. The resin could be used for 7 times repeatedly after regenerated with 95% ethanol and 1 mol/L NaOH. 3) For the first time, the quantitative methods of mainly active constituents, such as quercetin, luteolin, kaempferol and casticin in Artemisia rupestris L. extract and Artemisia rupestris L. were established by HPLC.
Conclusions: 1) The study of active parts and active constituents provided a substance basis of actions for further developing Artemisia rupestris L. And providing important information for flavonoids metabolism and structural modification researching on MS/MS fragment pathway of casticin. 2) The extraction and purification technology of Artemisia rupestris L. was reasonable, steady and repetitive. The yield ratio of Artemisia rupestris L. extract was 10.36~11.98%. The contents of total flavonoids was over 50% (51.29~53.95%) which met the demands. The mainly active constituents of luteolin and casticin were 9.77~9.84% and 23.77~24.16%, respectively. These results were steady and satisfied. The results of principle pharmacodynamics in vitro showed that the active part was as same as the 70% ethanol eluant screened assay in vitro in the first part, so it indicated that optimizing the preparative technology of the active part obtained anticipated result. 3) 3 batches of samples showed that established methods were easy and accurate, had nice recovery rates and good repetition, and could be used to control the quality of Artemisia rupestris L. extract and Artemisia rupestris L. which provided a basis for developing a novel drug and establishing its scientific, reasonable and strict quality control system in the future.
引文
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