CN113150057A - 一种新骨架单体化合物刺老苞皂苷c及其体外抗氧化作用 - Google Patents
一种新骨架单体化合物刺老苞皂苷c及其体外抗氧化作用 Download PDFInfo
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- CN113150057A CN113150057A CN202110338334.XA CN202110338334A CN113150057A CN 113150057 A CN113150057 A CN 113150057A CN 202110338334 A CN202110338334 A CN 202110338334A CN 113150057 A CN113150057 A CN 113150057A
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Abstract
本发明涉及刺老苞研究技术领域,更具体的说是涉及一种新骨架单体化合物刺老苞皂苷C及其体外抗氧化作用。本发明提供了一种新骨架单体化合物刺老苞皂苷C，从药用植物刺老苞中首次分离制备出一种新骨架单体化合物刺老苞皂苷C，并进行了单体化合物体外抗氧化作用的研究，为今后开展刺老苞相关通过抗氧化或淬灭自由基功能治疗相关疾病(心血管疾病、关节炎、老年黄斑变性等)的治病作用提供了可靠的实验数据支撑与理论依据。
Description
技术领域
本发明涉及刺老苞研究技术领域,更具体的说是涉及一种新骨架单体化合物刺老苞皂苷C及其体外抗氧化作用。
背景技术
刺老苞Aralia echinocaulis Hand.-Mazz.为五加科楤木属植物，在我国分布广泛，生于森林中，垂直分布海拔可达2600m。药材块片状或槽状，气微香，嚼之带粘液性，味辛，性平。归肝、肾经，功能滋阴健肾，祛风湿，壮筋骨，散瘀血，消肿毒，可用于风湿痹痛、跌打损伤、骨折等治疗。
现阶段刺老苞的研究，多集中在药材鉴定、人工栽培与药理作用等方面，而关于其药效物质基础的研究较为薄弱。目前从刺老苞中分离鉴定的化合物有皂苷类10个、挥发油95个、有机酸类1个及甾醇类1个，此外，刺老苞还含有丰富的糖类及微量元素。刺老苞根皮中总多糖、总黄酮的含量分别为7.33％及0.92％，钙、镁、铯、镓、铜、锌等无机元素含量较高，尤其是铜、钙、铯元素的含量高过同类中草药10多倍。刺老苞根皮能通过增强细胞活力、提高超氧化物歧化酶(SOD)活性及细胞膜流动性，降低活性自由氧(ROS)及脂质过氧化物(LPO)的含量，从而改善H2O2对MC3T3-E1成骨细胞的氧化损伤。但就其单体化合物体外淬灭不同来源的自由基的研究较为稀少
综上所述，现有技术存在以下缺陷：
缺陷一：现阶段刺老苞的研究，多集中在药材鉴定、人工栽培与药理作用等方面，而关于其药效物质基础的研究较为薄弱。目前从刺老苞中分离鉴定的化合物有皂苷类10个、挥发油95个、有机酸类1个及甾醇类1个。本专利从刺老苞中分离出一种新骨架单体化合物，即刺老苞皂苷C。
缺陷二：现阶段刺老苞的上述新骨架单体化合物的体外抗氧化作用尚无报道。本专利对刺老苞皂苷C体外DPPH自由基的清除能力、·OH诱导DNA氧化损伤的保护作用以及H2O2诱导DNA氧化损伤的保护作用进行了首次研究。
发明内容
有鉴于此，本发明的目的在于提供一种新骨架单体化合物刺老苞皂苷C 及其体外抗氧化作用，即从刺老苞中首次分离出刺老苞皂苷C，即刺老苞皂苷 C体外DPPH自由基的清除能力、·OH诱导DNA氧化损伤的保护作用以及 H2O2诱导DNA氧化损伤的保护作用进行了首次研究。
为实现上述目的，本发明提供如下技术方案：
刺老苞根皮2.0kg以70％乙醇加热回流提取3次，每次加入7L乙醇加热 2h，提取物旋转蒸发为400mL浸膏，取200mL浸膏以10％乙醇稀释为2.5L 溶液过MCI-GEL大孔树脂，乙醇-水按照10％、30％、50％、70％、90％乙醇梯度洗脱，收集各洗脱部分，回收溶剂，低温真空干燥为粉末。共得到9份样品，分别为10％乙醇Fr.1-4、10％乙醇Fr.5-9、30％乙醇Fr.1-3、30％-50％乙醇 Fr.3-4、50％乙醇Fr.1、50％乙醇Fr.2-3、70％乙醇Fr.1、70％乙醇Fr.2-4、90％乙醇Fr.1-3，通过薄层色谱检测；
取70％乙醇Fr.1部位4.00g，以乙腈∶水＝38∶62溶液溶解，过滤，湿法过C18柱，柱体积1L；以乙腈∶水＝38∶62、40∶60、43∶57、47∶53、 50∶50梯度洗脱，依据液相图谱合并浓缩，得14份样品Fr.T1-14，Fr.T5为化合物XIV 28mg。
所述化合物V为刺老苞皂苷C。
所述水中含0.01％甲酸。
所述刺老苞皂苷C对DPPH自由基有一定的清除能力。
所述刺老苞皂苷C对·OH诱导DNA氧化损伤有保护作用。
所述刺老苞皂苷C对H2O2诱导DNA氧化损伤有保护作用。
经由上述的技术方案可知，与现有技术相比，本发明从药用植物刺老苞中首次分离制备出本种植物未报道的刺老苞皂苷C，并进行了刺老苞皂苷C 体外抗氧化作用的研究，为今后开展地梢瓜相关通过抗氧化或淬灭自由基功能治疗相关疾病(心血管疾病、关节炎、老年黄斑变性等)的治病作用提供了可靠的实验数据支撑与理论依据。
具体实施方式
下面将结合本发明实施例，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
一、刺老苞皂苷C的分离鉴定方法：
(1)提取：刺老苞根皮2.0kg以70％乙醇加热回流提取3次，每次加入 7L乙醇加热2h，提取物旋转蒸发为400mL浸膏，取200mL浸膏以10％乙醇稀释为2.5L溶液过MCI-GEL大孔树脂，乙醇-水(10％、30％、50％、70％、90％乙醇梯度)梯度洗脱，收集各洗脱部分，回收溶剂，低温真空干燥为粉末。共得到9份样品，分别为10％乙醇Fr.1-4、10％乙醇Fr.5-9、30％乙醇Fr.1-3、 30％-50％乙醇Fr.3-4、50％乙醇Fr.1、50％乙醇Fr.2-3、70％乙醇Fr.1、70％乙醇 Fr.2-4、90％乙醇Fr.1-3，通过薄层色谱检测；
取70％乙醇Fr.1部位4.00g，以乙腈∶水(0.01％甲酸)＝38∶62溶液溶解，过滤，湿法过C18柱，柱体积1L。以乙腈∶水(0.01％甲酸)＝38∶62、 40∶60、43∶57、47∶53、50∶50梯度洗脱，依据液相图谱合并浓缩，得14 份样品Fr.T1-14，Fr.T5为化合物XIV(28mg)；
利用MCI-GEL大孔树脂、硅胶柱及色谱制备等方法，从刺老苞提取物中分离鉴定得到了一种新骨架单体化合物(化合物XIV)，通过对化合物的MS、 13C-NMR、1H-NMR、HSQC、HMBC、1H-1HCOSY等波谱学方法鉴定化合物结构，所得化合物数据未见文献报道，鉴定为新化合物。
(2)鉴定：刺老苞皂苷C(echinocaulisaponin C，化合物XIV)：
化合物XIV为白色粉末，硫酸乙醇显紫色。TOF-MS：m/z 779.4193[M-H2O]-，分子式为C41H66O15(理论值798.4420)。1H NMR(表1)显示该化合物有7 个甲基信号，分别为δ0.71(3H,s)，0.90(3H,s)，0.91(3H,s)，0.93(3H,s)， 1.22(3H,s)，1.29(3H,s)和1.51(s,3H)，糖质子信号δ3.5-6.5。13C NMR 在δ108.33，δ109.86处显示两个糖端基碳信号。通过1H-1HCOZY，质子信号在δ4.98(d,J＝7.74Hz),4.09(s),4.30(s)/4.70(s)，4.80(s)有相关性，质子信号在δ6.14(s),4.86(s)，4.77(s),δ5.01(d,J＝3.96Hz)，4.14(d,J ＝4.27Hz)/4.23(d,J＝3.65Hz)有相关性，将与氢信号相对应的碳信号通过 HSQC相连，确定对应的碳信号。根据文献比较，由糖1H和13C NMR数据确定为α-L-呋喃阿拉伯糖和β-D-吡喃葡萄糖醛酸。通过1H-1H COZY，质子信号在δ4.67(s)与δ1.68(o)/2.62(o,H-15)相关，因此δ69.83为16位的碳信号。在HMBC中，δ4.98(d，J＝7.74Hz，glc H-1’)与δ90.37(C-3)有关，因此糖与C-3相连。通过HMBC确定化合物XIV上与质子信号相邻的碳信号，它们分别为δ90.37(C-3)，29.27(C-24)，40.87(C-4)相关的δ0.93 (s，3H，H-23)；δ0.71(s，3H，H-25)与δ40.18(C-1)，57.11(C-5)， 50.86(C-9)，38.25(C-10)有关；δ0.90(s，3H，H-26)与δ35.54(C-7)， 42.23(C-8)，50.86(C-9)有关；δ1.51(s，3H，H-27)与δ44.79(C-13)， 42.87(C-14)，36.49(C-15)有关。δ1.29(s，3H，H-29)以及δ0.91(s， 3H，H-30)都与δ85.48有关，因此δ85.48为20位的碳信号。通过文献[10] 对比，化合物XIV苷元上的碳信号与熊果酸型皂苷相似，但苷元的C-12和C-13 位没有双键，C-16及C-20号位连了羟基。化合物XIV的苷元是一种新骨架苷元，命名为刺老苞苷元II(echinocaulisaglycone II)。因此，化合物XIV的结构为刺老苞苷元II-3-O-[α-L-呋喃阿拉伯糖(1”→4’)-β-D-吡喃葡萄糖醛酸 (echinocaulisaglycone II3-O-α-L-arabinopyranosyl-(1”→4’)-β -D-glucopyranosiduronic acid)，该化合物未见文献报道，命名为刺老苞皂苷C (echinocaulisaponin C)化学结构式为：其中(o)表示与其他峰重叠。
表1刺老苞皂苷C的13C-NMR及1H-NMR数据
二、体外抗氧化作用的研究：
刺老苞皂苷C的体外抗氧化活性评价
1、实验材料及仪器：
样品：刺老苞皂苷C
芦丁标准品(CAS#160-16-8，HPLC＞98％)、DPPH、氢氧化钠、亚硝酸钠、硝酸铝、EDTA二钠、3％过氧化氢：北京生化试剂公司；无水乙醇、六水合硫酸亚铁铵：北京市通广精细化工公司；维生素C：日本富士和光纯叶株式会；DNA 提取试剂盒(GD3121-1250preps)：BIOMIGA；酶标仪FlexStation 3：Molecular Devices。
2、实验方法与结果：
2.1、对DPPH自由基的清除能力
采用DPPH自由基清除模型，评价样品体外抗氧化能力。取96孔板，样品孔中加入不同浓度的样品溶液100μL，然后加入100μL的2×10-7mol/mL的 DPPH溶液；样参孔中分别加入不同浓度的样品溶液100μL、无水乙醇100μL；对照孔中加入DPPH溶液100μL、蒸馏水100μL，混匀，室温避光静置反应 30min，于517nm处测吸光值，以Vc为对照，用半数抑制率IC50表示抗氧化能力。
采用DPPH自由基清除模型，评价刺老苞皂苷A的抗氧化能力。其中， DPPH自由基的清除率的计算公式如下：
DPPH自由基清除率＝[1-(Ai-Aj)/A0]×100％。
其中，Ai为加入某浓度提取液反应液的吸光度，Aj是该浓度提取液在测定波长的本底吸光度，A0为阴性对照，即不加提取液时反应液的吸光度。
结果表明(表2)样品刺老苞皂苷C对DPPH自由基均有不同程度清除能力，清除率随溶液浓度的增大而增强。刺老苞皂苷C水溶物与醇溶物的清除率范围为27.86％～85.12％，IC50为0.3012mg/mL与30.18％～89.40％，IC50为 0.2652mg/ml。通过比较，相同浓度的刺老苞皂苷C醇溶物比其水溶物的清除率好。
2.2、对·OH诱导DNA氧化损伤的保护作用
在96孔板中依次加入1μL 100ng/μL DNA、10μL 0.1mol/L(NH4)2Fe(SO4)2 溶液、10μL 0.17mol/L的EDTA二钠溶液、10μL 0.015％H2O2溶液、10μL 10 mg/mLVc溶液、10μL不同浓度的样品溶液、40μLTE缓冲溶液，最后加入 0.5μL Goldview染料，轻轻摇匀静置反应5min，以维生素C为对照，测其荧光强度(荧光测定条件为：在激发波长486nm下扫描500～695nm范围内的荧光光强度)。
结果表明(表3)刺老苞皂苷C对·OH诱导DNA氧化损伤均有不同程度保护作用，作用效果随溶液浓度的增大而增强。刺老苞皂苷C水溶物与醇溶物的荧光强度范围分别为0.258～0.390与0.321～0.437。通过比较，相同浓度的刺老苞皂苷C醇溶物比其水溶物对·OH诱导DNA氧化损伤的保护作用更好。
表3刺老苞皂苷C对·OH诱导DNA氧化损伤的保护作用
2.3、对H2O2诱导DNA氧化损伤的保护作用
在96孔板中依次加入1μL 100ng/μL DNA溶液、10μL 3％H2O2溶液， 5μL样品溶液，95μL TE缓冲溶液以及0.5μL Goldview溶液，轻轻摇匀后静置反应10min，将盛样品比色皿放在紫外灯下照射10min，以维生素C为对照，测其荧光强度(荧光测定条件为：在激发波长486nm下扫描500～695nm 范围内的荧光光强度)。
结果表明(表4)样品刺老苞皂苷C对H2O2诱导DNA氧化损伤均有不同程度保护作用，作用效果随溶液浓度的增大而增强。刺老苞皂苷C水溶物与醇溶物的荧光强度范围分别为0.221～0.365与0.306～0.412。通过比较，相同浓度的刺老苞皂苷C醇溶物比其水溶物对H2O2诱导DNA氧化损伤的保护作用更好。
表4刺老苞皂苷C对H2O2诱导DNA氧化损伤的保护作用
本发明从药用植物刺老苞中首次分离制备出刺老苞皂苷C，并进行了刺老苞皂苷C体外抗氧化作用的研究，为今后开展刺老苞相关通过抗氧化或淬灭自由基功能治疗相关疾病(心血管疾病、关节炎、老年黄斑变性等)的治病作用提供了可靠的实验数据支撑与理论依据。
本说明书中各个实施例采用递进的方式描述，每个实施例重点说明的都是与其他实施例的不同之处，各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言，由于其与实施例公开的方法相对应，所以描述的比较简单，相关之处参见方法部分说明即可。
对所公开的实施例的上述说明，使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的，本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下，在其它实施例中实现。因此，本发明将不会被限制于本文所示的这些实施例，而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (6)
1.一种新骨架单体化合物刺老苞皂苷C，其特征在于，所述的刺老苞皂苷C的制备方法包括以下步骤：
刺老苞根皮2.0kg以70％乙醇加热回流提取3次，每次加入7L乙醇加热2h，提取物旋转蒸发为400mL浸膏，取200mL浸膏以10％乙醇稀释为2.5L溶液过MCI-GEL大孔树脂，乙醇-水按照10％、30％、50％、70％、90％乙醇梯度洗脱，收集各洗脱部分，回收溶剂，低温真空干燥为粉末。共得到9份样品，分别为10％乙醇Fr.1-4、10％乙醇Fr.5-9、30％乙醇Fr.1-3、30％-50％乙醇Fr.3-4、50％乙醇Fr.1、50％乙醇Fr.2-3、70％乙醇Fr.1、70％乙醇Fr.2-4、90％乙醇Fr.1-3，通过薄层色谱检测；
取70％乙醇Fr.1部位4.00g，以乙腈∶水＝38∶62溶液溶解，过滤，湿法过C18柱，柱体积1L；以乙腈∶水＝38∶62、40∶60、43∶57、47∶53、50∶50梯度洗脱，依据液相图谱合并浓缩，得14份样品Fr.T1-14，Fr.T5为化合物XIV28mg。
2.根据权利要求1所述的一种新骨架单体化合物刺老苞皂苷C，其特征在于，所述化合物XIV为刺老苞皂苷C。
3.根据权利要求2所述的一种新骨架单体化合物刺老苞皂苷C，其特征在于，所述水中含0.01％甲酸。
4.根据权利要求3所述的一种新骨架单体化合物刺老苞皂苷A的体外抗氧化作用，其特征在于，所述刺老苞皂苷C对DPPH自由基有一定的清除能力。
5.根据权利要求3所述的一种新骨架单体化合物刺老苞皂苷A的体外抗氧化作用，其特征在于，所述刺老苞皂苷C对·OH诱导DNA氧化损伤有保护作用。
6.根据权利要求3所述的一种新骨架单体化合物刺老苞皂苷A的体外抗氧化作用，其特征在于，所述刺老苞皂苷C对H2O2诱导DNA氧化损伤有保护作用。
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Non-Patent Citations (2)
| Title |
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| 燕梦云: "土家族药刺老苞根皮皂苷类化学成分的分离鉴定及对原代破骨细胞的抑制作用", 《中国优秀硕士学位论文（医药卫生科技辑）》 * |
| 王萌萌等: "土家传统药刺老苞总皂苷对 H2O2诱导的 MC3T3-E1成骨细胞损伤改善", 《中国民族医药杂志》 * |
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