藏药镰形棘豆黄酮类成分抗炎与抗氧化活性研究及其含量测定
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摘要
本文通过水蒸气蒸馏、超临界CO2萃取和顶空萃取三种方法并结合GC和GC/MS技术分析藏药镰形棘豆(Oxytropis falcata Bunge)中的挥发性成分,共鉴定出58个化合物,分别占71.0%,85.6%和84.5%。烷烃类、黄酮类和醛类化合物为主要挥发性成分。三种方法得到的挥发性成分在保留时间值上具有一定的连续性,能更完全地阐述清楚藏药镰形棘豆的挥发性成分,为进一步开发利用这种药用植物提供科学依据。
在研究镰形棘豆总生物碱提取与纯化的工艺中。我们首先通过预试验确定镰形棘豆中生物碱的存在,然后通过单因素和L9(34)正交实验设计考察各因素对镰形棘豆总生物碱提取和纯化的影响。结果表明镰形棘豆总生物碱提取与纯化的最佳工艺如下：以含0.5%醋酸的40%乙醇溶液为提取溶剂,物料比(原料质量：酸性乙醇体积)为1：20,提取温度60℃,超声提取(30 min/次×2次)后,经732型阳离子交换树脂吸附,由1.0%NH3·H20的60%乙醇溶液提取树脂中总生物碱(30 min/次×3次),在此条件下镰形棘豆中总生物碱的提取效果最好。
为了考察镰形棘豆中总黄酮和总酚的含量。我们以芦丁和没食子酸为对照品,分别采用NaNO2-Al(NO3)3-NaOH和Folin-Ciocalteu比色法测定了镰形棘豆中总黄酮与总酚的含量。结果显示,芦丁浓度在4.2-50.4μg/mL范围内线性关系良好。该方法平均加样回收率为98.07%,RSD为1.488%(n=9)。西藏安多、班戈和青海共和县3个产地的镰形棘豆中总黄酮含量分别为1.218%、1.296%和1.139%。没食子酸浓度在0.804-6.432μg/mL范围内线性关系良好。该方法平均加样回收率为98.87%,RSD为2.484%(n=6),3个产地镰形棘豆中总酚的含量分别为0.530%、0.657%和0.493%。这两种方法灵敏准确、精密度高、稳定性好、重复性强,分别可以用作镰形棘豆中总黄酮和总酚含量的测定,为镰形棘豆抗氧化性和抗炎作用的研究提供参考。
此外本实验对镰形棘豆甲醇提取物,总黄酮和总生物碱部位进行了体外抗氧化性研究,分别采用总抗氧化活性、DPPH、羟基和超氧自由基清除实验作为评价其抗氧化性指标,筛选出总黄酮部位为镰形棘豆中有效的抗氧化活性部位,其总抗氧化活性为148.19±4.12]mg Vc/g, DPPH和羟基自由基清除的IC50值分别为53.24±1.42和365.66±5.98μg/mL。实验结果表明,镰形棘豆总黄酮有效部位具有较好的抗炎抗氧化活性,且无任何胃肠道刺激作用。其抗炎机制可能与降低机体脂质过氧化程度(MDA, P<0.05)与提高机体抗氧化酶活性(SOD, P <0.35; CAT, P<0.35和GSH-Px, P<0.01)有关。
本文通过柱层析方法从镰形棘豆植物中分离得到4个黄酮类化合物：2’,4’-二羟基查尔酮(1),7-羟基二氢黄酮(2),5,7-二羟基-4’-甲氧基黄酮醇(3)和5,7-二羟基-4’-甲氧基黄酮-3-O-β-半乳糖苷(4),化合物4为该属植物中首次分离得到。通过HPLC-DAD方法同时测定了这4个化合物的含量。此外,我们分别采用体外总抗氧化活性、DPPH和超氧自由基清除活性,细胞毒性和LPS诱导小鼠RAW264.7巨噬细胞产生NO抑制的实验对镰形棘豆黄酮类化合物的抗炎以及抗氧化活性进行研究。结果表明,化合物1和2具有较好的抑制LPS诱导RAW 264.7细胞产生NO的活性,四个化合物中化合物3表现出最强的体外清除自由基活性。它们的体外抗氧化与抗炎活性与镰形棘豆临床上常用的功效密切相关。因此,化合物1,2和3可以作为该植物的主要活性和指标性成分,为该植物在质量控制方面提供了参考。
To examine the volatile compositions from Oxytropis falcata Bunge, the volatiles were obtained using water distillation, supercritical CO2 extraction and headspace extraction methods and their chemical compositions were analyzed by GC and GC/MS.58 compounds were identified and the amount of the identified componunds represented for 71.0%,85.6% and 84.5% of all the volatiles, respectively. The main components were paraffin hydrocarbons 30.1%(water distillation), flavonoids 68.5%(supercritical CO2 extraction) and aldehydes 53.8% (headspace extraction). In addition, micromolecular terpenoids, organic acids, esters and nitrogenous compounds were also identified. It suggested that the retention times of the volatiles extracted using three methods were consecutive which could provide comprehensive volatile compositions of O. falcata Bunge and a scientific basis for further development and utilization of this medicinal plant.
To study on the extraction and purification of total alkaloids from Oxytropis falcata Bunge, Firstly, the existence of alkaloids in the material was determined by the preliminary experiments. Then the single-factor and L9 (34) orthogonal test were designed to study the effect of the extraction and purification of total alkaloids from Oxytropis falcata Bunge. The results indicated that the optimum condition on the extraction and purification of total alkaloids from Oxytropis falcata Bunge was as follows:0.5% HAc-40% ethanol solution as extraction solvent, the ratio of raw material powder to solvent was 1.0 g. 20 mL, extraction temperature was 60℃, after ultrasonic extraction (30 min/time×2 times), the cation exchange resins were used to extract and purify total alkaloids from the extracted materials with 1.0% NH3·H2O-60% ethanol solution (30 min/times×3 times). The best yield of total alkaloids could be obtained under this condition.
To investigate the contents of total flavonoids and phenolic acids from Oxytropis falcata. We determined the content of total flavonoids by NaNO2-Al(NO3)3-NaOH colorimetric assay with rutin as reference substance. And the content of total phenolic acids by using the Folin-Ciocalteu assay with gallic acid as reference substance. Rutin was found to show a good linear relationship in a range of 4.2-50.4μg/mL. The average recovery was 98.07% and the relative standard deviation (RSD) was 1.488%(n=9). Gallic acid showed a good linearity within a range of 0.804-6.432μg/mL. The average recovery was 98.87% and RSD was 2.484%(n=6). The contents of total flavonoids and phenolic acids in Oxytropis falcata from Tibet An duo, Tibet Bange and Qinghai Gong he were 1.218%,1.296%, 1.139% and 0.530%,0.657%,0.493%, respectively. These two proposed methods are sensitive, precise, accurate and reproducible, and are suitable for the determination of total flavonoids and phenolic acids from Oxytropis falcata Bunge.
In addition, various fractions extracted from Oxytropis falcata Bunge were investigated for their antioxidant activities in vitro for the first time. Flavonoid fraction (FF) was major active constituents responsible for the activities on three antioxidant models by total antioxidant activity (148.19±4.12 mg Vc/g), DPPH and hydroxyl radical-scavenging activities, with the IC50 of 53.24±1.42 and 365.66±5.98μg/mL, respectively. The anti-inflammatory mechanism of FF may be due, at least in part, to the decrease of MDA levels (P<0.05) and enhancement of SOD (P <0.35), CAT (P<0.35) and GSH-Px (P<0.01) activities without inducing any gastric damage. The results provide evidences to support the folk medicinal utilization of O. falcata for the treatment of inflammation.
Moreover, Oxytropis falcata Bunge has long been regarded as an anti-inflammatory medicinal plant. By the analysis of HPLC-DAD, four flavonoid compounds,2',4'-dihydroxy chalcone (1),7-hydroxy flavonone (2), 5,7-dihydroxy-4'-methoxy flavonol (3) and 5,7-dihydroxy-4'-methoxy flavone-3-O-β-D-galactoside (4), were isolated, identified and quantified.4 was isolated for the first time from this plant. In this study, we focused on evaluating the antioxidant activities of four flavonoid compounds on the total antioxidant activities, DPPH and superoxide radical-scavenging activities, for their cytotoxic and anti-inflammatory activities on the inhibition on LPS-induced NO production in RAW 264.7 cells. Taken together,3 as well as 1 and 2 could contribute, at least in part, to the anti-inflammatory properties of Oxytropis falcata Bunge, which could be used as marker compounds in the standardization and quality control for this medicinal plant.
在研究镰形棘豆总生物碱提取与纯化的工艺中。我们首先通过预试验确定镰形棘豆中生物碱的存在,然后通过单因素和L9(34)正交实验设计考察各因素对镰形棘豆总生物碱提取和纯化的影响。结果表明镰形棘豆总生物碱提取与纯化的最佳工艺如下：以含0.5%醋酸的40%乙醇溶液为提取溶剂,物料比(原料质量：酸性乙醇体积)为1：20,提取温度60℃,超声提取(30 min/次×2次)后,经732型阳离子交换树脂吸附,由1.0%NH3·H20的60%乙醇溶液提取树脂中总生物碱(30 min/次×3次),在此条件下镰形棘豆中总生物碱的提取效果最好。
为了考察镰形棘豆中总黄酮和总酚的含量。我们以芦丁和没食子酸为对照品,分别采用NaNO2-Al(NO3)3-NaOH和Folin-Ciocalteu比色法测定了镰形棘豆中总黄酮与总酚的含量。结果显示,芦丁浓度在4.2-50.4μg/mL范围内线性关系良好。该方法平均加样回收率为98.07%,RSD为1.488%(n=9)。西藏安多、班戈和青海共和县3个产地的镰形棘豆中总黄酮含量分别为1.218%、1.296%和1.139%。没食子酸浓度在0.804-6.432μg/mL范围内线性关系良好。该方法平均加样回收率为98.87%,RSD为2.484%(n=6),3个产地镰形棘豆中总酚的含量分别为0.530%、0.657%和0.493%。这两种方法灵敏准确、精密度高、稳定性好、重复性强,分别可以用作镰形棘豆中总黄酮和总酚含量的测定,为镰形棘豆抗氧化性和抗炎作用的研究提供参考。
此外本实验对镰形棘豆甲醇提取物,总黄酮和总生物碱部位进行了体外抗氧化性研究,分别采用总抗氧化活性、DPPH、羟基和超氧自由基清除实验作为评价其抗氧化性指标,筛选出总黄酮部位为镰形棘豆中有效的抗氧化活性部位,其总抗氧化活性为148.19±4.12]mg Vc/g, DPPH和羟基自由基清除的IC50值分别为53.24±1.42和365.66±5.98μg/mL。实验结果表明,镰形棘豆总黄酮有效部位具有较好的抗炎抗氧化活性,且无任何胃肠道刺激作用。其抗炎机制可能与降低机体脂质过氧化程度(MDA, P<0.05)与提高机体抗氧化酶活性(SOD, P <0.35; CAT, P<0.35和GSH-Px, P<0.01)有关。
本文通过柱层析方法从镰形棘豆植物中分离得到4个黄酮类化合物：2’,4’-二羟基查尔酮(1),7-羟基二氢黄酮(2),5,7-二羟基-4’-甲氧基黄酮醇(3)和5,7-二羟基-4’-甲氧基黄酮-3-O-β-半乳糖苷(4),化合物4为该属植物中首次分离得到。通过HPLC-DAD方法同时测定了这4个化合物的含量。此外,我们分别采用体外总抗氧化活性、DPPH和超氧自由基清除活性,细胞毒性和LPS诱导小鼠RAW264.7巨噬细胞产生NO抑制的实验对镰形棘豆黄酮类化合物的抗炎以及抗氧化活性进行研究。结果表明,化合物1和2具有较好的抑制LPS诱导RAW 264.7细胞产生NO的活性,四个化合物中化合物3表现出最强的体外清除自由基活性。它们的体外抗氧化与抗炎活性与镰形棘豆临床上常用的功效密切相关。因此,化合物1,2和3可以作为该植物的主要活性和指标性成分,为该植物在质量控制方面提供了参考。
To examine the volatile compositions from Oxytropis falcata Bunge, the volatiles were obtained using water distillation, supercritical CO2 extraction and headspace extraction methods and their chemical compositions were analyzed by GC and GC/MS.58 compounds were identified and the amount of the identified componunds represented for 71.0%,85.6% and 84.5% of all the volatiles, respectively. The main components were paraffin hydrocarbons 30.1%(water distillation), flavonoids 68.5%(supercritical CO2 extraction) and aldehydes 53.8% (headspace extraction). In addition, micromolecular terpenoids, organic acids, esters and nitrogenous compounds were also identified. It suggested that the retention times of the volatiles extracted using three methods were consecutive which could provide comprehensive volatile compositions of O. falcata Bunge and a scientific basis for further development and utilization of this medicinal plant.
To study on the extraction and purification of total alkaloids from Oxytropis falcata Bunge, Firstly, the existence of alkaloids in the material was determined by the preliminary experiments. Then the single-factor and L9 (34) orthogonal test were designed to study the effect of the extraction and purification of total alkaloids from Oxytropis falcata Bunge. The results indicated that the optimum condition on the extraction and purification of total alkaloids from Oxytropis falcata Bunge was as follows:0.5% HAc-40% ethanol solution as extraction solvent, the ratio of raw material powder to solvent was 1.0 g. 20 mL, extraction temperature was 60℃, after ultrasonic extraction (30 min/time×2 times), the cation exchange resins were used to extract and purify total alkaloids from the extracted materials with 1.0% NH3·H2O-60% ethanol solution (30 min/times×3 times). The best yield of total alkaloids could be obtained under this condition.
To investigate the contents of total flavonoids and phenolic acids from Oxytropis falcata. We determined the content of total flavonoids by NaNO2-Al(NO3)3-NaOH colorimetric assay with rutin as reference substance. And the content of total phenolic acids by using the Folin-Ciocalteu assay with gallic acid as reference substance. Rutin was found to show a good linear relationship in a range of 4.2-50.4μg/mL. The average recovery was 98.07% and the relative standard deviation (RSD) was 1.488%(n=9). Gallic acid showed a good linearity within a range of 0.804-6.432μg/mL. The average recovery was 98.87% and RSD was 2.484%(n=6). The contents of total flavonoids and phenolic acids in Oxytropis falcata from Tibet An duo, Tibet Bange and Qinghai Gong he were 1.218%,1.296%, 1.139% and 0.530%,0.657%,0.493%, respectively. These two proposed methods are sensitive, precise, accurate and reproducible, and are suitable for the determination of total flavonoids and phenolic acids from Oxytropis falcata Bunge.
In addition, various fractions extracted from Oxytropis falcata Bunge were investigated for their antioxidant activities in vitro for the first time. Flavonoid fraction (FF) was major active constituents responsible for the activities on three antioxidant models by total antioxidant activity (148.19±4.12 mg Vc/g), DPPH and hydroxyl radical-scavenging activities, with the IC50 of 53.24±1.42 and 365.66±5.98μg/mL, respectively. The anti-inflammatory mechanism of FF may be due, at least in part, to the decrease of MDA levels (P<0.05) and enhancement of SOD (P <0.35), CAT (P<0.35) and GSH-Px (P<0.01) activities without inducing any gastric damage. The results provide evidences to support the folk medicinal utilization of O. falcata for the treatment of inflammation.
Moreover, Oxytropis falcata Bunge has long been regarded as an anti-inflammatory medicinal plant. By the analysis of HPLC-DAD, four flavonoid compounds,2',4'-dihydroxy chalcone (1),7-hydroxy flavonone (2), 5,7-dihydroxy-4'-methoxy flavonol (3) and 5,7-dihydroxy-4'-methoxy flavone-3-O-β-D-galactoside (4), were isolated, identified and quantified.4 was isolated for the first time from this plant. In this study, we focused on evaluating the antioxidant activities of four flavonoid compounds on the total antioxidant activities, DPPH and superoxide radical-scavenging activities, for their cytotoxic and anti-inflammatory activities on the inhibition on LPS-induced NO production in RAW 264.7 cells. Taken together,3 as well as 1 and 2 could contribute, at least in part, to the anti-inflammatory properties of Oxytropis falcata Bunge, which could be used as marker compounds in the standardization and quality control for this medicinal plant.
引文
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