丙二酰基人参皂苷化学成分及其治疗2型糖尿病大鼠的药效学研究
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摘要
本项研究采用常规的天然产物化学方法,并结合现代的HPLC分离技术,运用IR.MS. HR-SI-MS.1H NMR、13C NMR和2D NMR (HSQC and HMBC)等光谱鉴定技术,从中国鲜人参中分离鉴定了13个单体皂苷。其中首次获得了一个新化合物——丙二酰基人参皂苷Ra3,其结构鉴定为：3-0-[6-0-丙二酰-(?)-D-葡萄吡喃糖(1→2)-(?)-D-葡萄吡糖]-20-0-[β-D-木糖(1→3)-(?)-D-葡萄吡喃糖(1→6)-(?)-D-葡萄吡喃糖]-20(S)-原人参二醇{3-O-(6-O-malonyl-β-D-glucopyranosyl(1→2)-β-D-glucopyranoside)-20-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside20(s)一protopanaxadiol}。
应用正交试验设计,研究了丙二酰基人参皂苷的超声提取方法,结果发现溶剂的倍数,溶剂的浓度,提取时间和提取次数均对丙二酰基人参皂苷的提取量有影响,四因素的优化组合是A2B3C3D3.即：溶剂倍数为10倍,乙醇浓度为80%,提取时间30 min,提取次数3次。
采用HPLC对不同采收时期(出苗展叶期、开花期、绿果期、红果期、采收期、枯萎期)采摘的卜6年生的人参主根中包括丙二酰基人参皂苷在内的10种主要皂苷进行了测定,结果展示了4种丙二酰基人参皂苷含量在人参的不同年生和不同采收期(除少数时期外)均高于6种中性皂苷,占人参总皂苷的44%-59%,为人参皂苷的主要构成部分。
采用高脂饮食联合小剂量STZ腹腔注射建立2型糖尿病模型,观察了丙二酰基人参皂苷对2型糖尿病的治疗作用。结果表明丙二酰基人参皂苷具有显著的降低空腹血糖的作用,明显提高机体对葡萄糖的耐受量和胰岛素敏感指数。另外,还有一定的降低血脂,改善脂质紊乱的作用。
Diabetes Mellitus is the glucose, protein and lipid metabolic disorder syndrome caused by absolute or relative lack of insulin secretion, the basic characteristics of which is blood glucose increasing. There are two forms of diabetes:insulin-dependent diabetes mellitus(IDDM, type 1) and non-insulin-dependent diabetes mellitus (NIDDM, type 2),95% of the diabetes are NIDDM. Currently, with the improvement of living level and the change of food structure, incidence rate of diabetes tend to rise up year by year, Diabetes has become the third disease causing death following cancer and cardiovascular disease. Diabetes mellitus has been a great public heath problem because of the harms of DM and its various chromic complications, besides huge direct and indirect medical cost. Therefore, it is very important to look for a safe and effective method to control blood sugar for diabetes prevention and treatment.
Now the antidiabetes drugs include insulin sulfonylurea derivatives, thiazolid derivatives, biguanidine derivatives, a-glucosidase inhibitor agent. Though we can select different kinds of drugs to treat diabetes nellitus, oral hypoglycemic drugs have many adverse reactions and toxic effects. The adverse reaction and Somogy caused by vein injecting insulin for a long time make us to find a better drug in Chinese traditional medicine.
Ginseng(Panax ginseng C. A. Meyer) has been used in China for thousands of years as a traditional nedicine. Panax ginseng has been recorded to treat "Xiaoke" symptom in many ancient Chinese medical literatures. "Xiaoke", in general, indicates diabetes mellitus. Modern pharmacological studies have shown that in vitro and in vivo animal studies and clinical trials support the claim that the root of Panax ginseng and the (?)oot of other ginseng products possess antihyperglycemic activity, without evidence of adverse effects or :oxicity, ginseng, has been used clinically to treat diabetes.
Ginsenosides are the main active constituents in P. ginseng and More than 50 ginsenosides have been identified, isolated and characterised till now. Malonyl-ginsenosides (MGR) are natural ginsenosides exist in (?)oth fresh and air-dried ginseng roots which contain malonyl residue attached to glucose unit of the (?)orresponding neutral ginsenosides such as Rb1, Rb2, Re, Rd to form m-Rb1, m-Rb2, m-Rc and m-Rd. Malonyl ginsenosides are unstable and demalonylate to the corresponding neutral ginsenosides under high (?)emperature conditions.The content of acidic saponins malonyl-ginsenoside Rb1, Rb2, Re, and Rd represent between 35 and 60% of the total content of ginsenosides in P. ginseng. Since it can't solve in n-BuOH, a lot of VIGR had been removed in the water portion as residues during the extraction process of total saponins and solation and purification were very difficult. The true ginsenosides of ginseng and previous pharmacological studies of ginsenosides were being underestimated by ignoring of MGR, the pharmacological effect of MGR has not been explored so far; So literature reports were seldom.
In order to evaluate the quality of ginseng and to the settle foundation of new drug exploitation, this text begins with water-soluble saponin research which were about its'extraction, separation, identification, content and anti-diabetes pharmacology activity.
Thirteen saponins were isolated from fresh ginseng in China by the different process of the extraction and isolation, such as extraction of organic solvent, Macro-reticular resins, ODS column chromatography, silica gen column chromatography and others. On the basis of the physical constants, chemical evidence and spectrum analysis[IR、LCQ-MS、HR-SI-MS.1H NMR、13C NMR and 2D NMR (HSQC and HMBC)], The thirteen compounds were characterized. Among them, a new compound, Malonyl ginsenoside-Ra3 elucidated as 3-0-(6-O-malonyl-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside)-20-O-β-D-xylopyranosyl (1→3)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside-20(s)-protopanaxadiol.
The orthogonal experiment was used for study of ultrasound-assisted extraction process of malonyl-ginsenosides. The result indicated that the multiple of solvent, concentration of solvent, hours of extraction and times of extraction are the important factors. Though concentration of solvent is inferior effect factor compared with the other three factors, it got to remarkable distinction. The optimal selection of the four factors is multiple of solvent with 10-fold, concentration of methanol with 80%, hours of extraction for 30 min and times of extraction for 3 times.
The contents of 10 ginsenosides (m-Rb), m-Rb2, m-Rc, m-Rd, Rg1, Re, Rbb Rc, Rb2, Rd) in different growing seasons and ages of Panax ginseng (obtained from Jingyu County in Jilin Province, China) were quantified by high-performance liquid chromatography coupled with UV-vis detector (HPLC-UV). The results indicate that the content of malonyl ginsenosides in P. ginseng root increases with age and the growing season, the increase rate of the content of ginsenoside is different. Content of M-Rb1、M-Rc、M-Rb2、Rb1 and Rg1 in P. ginseng root is higher compared with other ginsenosides, the total content of malonyl ginsenosides changed slowly in one and three-year-old P. ginseng, while rapidly in four and five-year-old. The content of malonyl ginsenosides is highest in red fruit period and higher in green fruit period than that in other growing seasons. The content of malonyl ginsenosides present between 44 and 59% of total ginsenosides, with several exceptions, malonyl ginsenosides in most of harvests and ages are slightly higher than six ginsenosides.
The aims of this investigation were to characterize the regulation of glucocorticoid hormone. Male Wistar rats were randomly divided into five groups:Malonyl ginsenosides was administrated at 50mg/Kg for Low-dose malonyl ginsenosides group and at 100mg/Kg for high dose malonyl ginsenosides group by gastric gavage for 5 weeks. Control rats were gavaged with an equal volume of vehicle (distilled water). After six months on HFD. The animals were divided into control (n=10), diabetes mellitus (n=10), treated with LMGR (n=10), and treated with HMGR (n=10). Glucose tolerance test, insulin tolerance test and relevant index calculation were used to evaluate the fasting blood glucose, self-regulating ability of blood glucose, levels insulin sensitivity and insulin resistance for analysis of analogues.
The results showed that LMGR group (50mg/Kg) rats could decrease fasting plasma glucose, but the effect was not significant (P>0.05); while HMGR group (100mg/Kg) rats had significantly decreased fasting blood glucose(P<0.01).
Glucose tolerance test results demonstrated that the model group glucose the area of under the curve were significantly higher than LMGR and HMGR group. The area under the curve was compared with model group, showed significant dose-dependent. Type 2 diabetic rats decreased glucose tolerance, insulin resistance occurs, and malonyl ginsenosides treatment significantly increased the amount the body glucose tolerance and improved insulin resistance.
Malonyl ginsenosides reduced body weight, serum triglyceride (TG) and total cholesterol (TC) levels in diabetic rats, the level of TC was significantly lower than model group (P<0.05). It suggested that malonyl ginsenosides improved the disorder of the serum lipid metabolism.
The achievements of this research are as follows:
On the basis of the physical constants, chemical evidence and spectrum analysis[IR、LCQ-MS HR-SI-MS.'H NMR、13C NMR and 2D NMR (HSQC and HMBC)], a new compound, Malonyl ginsenoside-Ra3 elucidated as 3-0-(6-O-malonyl-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside)-20-0-β-D-xylopyranosyl (1→3)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside-20(s)-protopanaxadiol.
The contents of 10 ginsenosides (m-Rb1,m-Rb2, m-Rc, m-Rd, Rg1, Re, Rb1, Rc, Rb2, Rd) in different growing seasons and ages of Panax ginseng were quantified by high-performance liquid chromatography coupled with UV-vis detector. The results show that the content of malonyl ginsenosides present between 44 and 59% of total ginsenosides, with several exceptions, malonyl ginsenosides in most of harvests and ages are slightly higher than six ginsenosides.
We studied the effect of MGR on improvement of glycemia, lipid metabolism and the insulin resistance in Type 2 Diabetes Mellitus Rats (T2DM). The results suggested that MGR could decrease the blood glucose, improve the disorder of the serum lipid metabolism and Insulin sensitivity in T2DM rats.
应用正交试验设计,研究了丙二酰基人参皂苷的超声提取方法,结果发现溶剂的倍数,溶剂的浓度,提取时间和提取次数均对丙二酰基人参皂苷的提取量有影响,四因素的优化组合是A2B3C3D3.即：溶剂倍数为10倍,乙醇浓度为80%,提取时间30 min,提取次数3次。
采用HPLC对不同采收时期(出苗展叶期、开花期、绿果期、红果期、采收期、枯萎期)采摘的卜6年生的人参主根中包括丙二酰基人参皂苷在内的10种主要皂苷进行了测定,结果展示了4种丙二酰基人参皂苷含量在人参的不同年生和不同采收期(除少数时期外)均高于6种中性皂苷,占人参总皂苷的44%-59%,为人参皂苷的主要构成部分。
采用高脂饮食联合小剂量STZ腹腔注射建立2型糖尿病模型,观察了丙二酰基人参皂苷对2型糖尿病的治疗作用。结果表明丙二酰基人参皂苷具有显著的降低空腹血糖的作用,明显提高机体对葡萄糖的耐受量和胰岛素敏感指数。另外,还有一定的降低血脂,改善脂质紊乱的作用。
Diabetes Mellitus is the glucose, protein and lipid metabolic disorder syndrome caused by absolute or relative lack of insulin secretion, the basic characteristics of which is blood glucose increasing. There are two forms of diabetes:insulin-dependent diabetes mellitus(IDDM, type 1) and non-insulin-dependent diabetes mellitus (NIDDM, type 2),95% of the diabetes are NIDDM. Currently, with the improvement of living level and the change of food structure, incidence rate of diabetes tend to rise up year by year, Diabetes has become the third disease causing death following cancer and cardiovascular disease. Diabetes mellitus has been a great public heath problem because of the harms of DM and its various chromic complications, besides huge direct and indirect medical cost. Therefore, it is very important to look for a safe and effective method to control blood sugar for diabetes prevention and treatment.
Now the antidiabetes drugs include insulin sulfonylurea derivatives, thiazolid derivatives, biguanidine derivatives, a-glucosidase inhibitor agent. Though we can select different kinds of drugs to treat diabetes nellitus, oral hypoglycemic drugs have many adverse reactions and toxic effects. The adverse reaction and Somogy caused by vein injecting insulin for a long time make us to find a better drug in Chinese traditional medicine.
Ginseng(Panax ginseng C. A. Meyer) has been used in China for thousands of years as a traditional nedicine. Panax ginseng has been recorded to treat "Xiaoke" symptom in many ancient Chinese medical literatures. "Xiaoke", in general, indicates diabetes mellitus. Modern pharmacological studies have shown that in vitro and in vivo animal studies and clinical trials support the claim that the root of Panax ginseng and the (?)oot of other ginseng products possess antihyperglycemic activity, without evidence of adverse effects or :oxicity, ginseng, has been used clinically to treat diabetes.
Ginsenosides are the main active constituents in P. ginseng and More than 50 ginsenosides have been identified, isolated and characterised till now. Malonyl-ginsenosides (MGR) are natural ginsenosides exist in (?)oth fresh and air-dried ginseng roots which contain malonyl residue attached to glucose unit of the (?)orresponding neutral ginsenosides such as Rb1, Rb2, Re, Rd to form m-Rb1, m-Rb2, m-Rc and m-Rd. Malonyl ginsenosides are unstable and demalonylate to the corresponding neutral ginsenosides under high (?)emperature conditions.The content of acidic saponins malonyl-ginsenoside Rb1, Rb2, Re, and Rd represent between 35 and 60% of the total content of ginsenosides in P. ginseng. Since it can't solve in n-BuOH, a lot of VIGR had been removed in the water portion as residues during the extraction process of total saponins and solation and purification were very difficult. The true ginsenosides of ginseng and previous pharmacological studies of ginsenosides were being underestimated by ignoring of MGR, the pharmacological effect of MGR has not been explored so far; So literature reports were seldom.
In order to evaluate the quality of ginseng and to the settle foundation of new drug exploitation, this text begins with water-soluble saponin research which were about its'extraction, separation, identification, content and anti-diabetes pharmacology activity.
Thirteen saponins were isolated from fresh ginseng in China by the different process of the extraction and isolation, such as extraction of organic solvent, Macro-reticular resins, ODS column chromatography, silica gen column chromatography and others. On the basis of the physical constants, chemical evidence and spectrum analysis[IR、LCQ-MS、HR-SI-MS.1H NMR、13C NMR and 2D NMR (HSQC and HMBC)], The thirteen compounds were characterized. Among them, a new compound, Malonyl ginsenoside-Ra3 elucidated as 3-0-(6-O-malonyl-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside)-20-O-β-D-xylopyranosyl (1→3)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside-20(s)-protopanaxadiol.
The orthogonal experiment was used for study of ultrasound-assisted extraction process of malonyl-ginsenosides. The result indicated that the multiple of solvent, concentration of solvent, hours of extraction and times of extraction are the important factors. Though concentration of solvent is inferior effect factor compared with the other three factors, it got to remarkable distinction. The optimal selection of the four factors is multiple of solvent with 10-fold, concentration of methanol with 80%, hours of extraction for 30 min and times of extraction for 3 times.
The contents of 10 ginsenosides (m-Rb), m-Rb2, m-Rc, m-Rd, Rg1, Re, Rbb Rc, Rb2, Rd) in different growing seasons and ages of Panax ginseng (obtained from Jingyu County in Jilin Province, China) were quantified by high-performance liquid chromatography coupled with UV-vis detector (HPLC-UV). The results indicate that the content of malonyl ginsenosides in P. ginseng root increases with age and the growing season, the increase rate of the content of ginsenoside is different. Content of M-Rb1、M-Rc、M-Rb2、Rb1 and Rg1 in P. ginseng root is higher compared with other ginsenosides, the total content of malonyl ginsenosides changed slowly in one and three-year-old P. ginseng, while rapidly in four and five-year-old. The content of malonyl ginsenosides is highest in red fruit period and higher in green fruit period than that in other growing seasons. The content of malonyl ginsenosides present between 44 and 59% of total ginsenosides, with several exceptions, malonyl ginsenosides in most of harvests and ages are slightly higher than six ginsenosides.
The aims of this investigation were to characterize the regulation of glucocorticoid hormone. Male Wistar rats were randomly divided into five groups:Malonyl ginsenosides was administrated at 50mg/Kg for Low-dose malonyl ginsenosides group and at 100mg/Kg for high dose malonyl ginsenosides group by gastric gavage for 5 weeks. Control rats were gavaged with an equal volume of vehicle (distilled water). After six months on HFD. The animals were divided into control (n=10), diabetes mellitus (n=10), treated with LMGR (n=10), and treated with HMGR (n=10). Glucose tolerance test, insulin tolerance test and relevant index calculation were used to evaluate the fasting blood glucose, self-regulating ability of blood glucose, levels insulin sensitivity and insulin resistance for analysis of analogues.
The results showed that LMGR group (50mg/Kg) rats could decrease fasting plasma glucose, but the effect was not significant (P>0.05); while HMGR group (100mg/Kg) rats had significantly decreased fasting blood glucose(P<0.01).
Glucose tolerance test results demonstrated that the model group glucose the area of under the curve were significantly higher than LMGR and HMGR group. The area under the curve was compared with model group, showed significant dose-dependent. Type 2 diabetic rats decreased glucose tolerance, insulin resistance occurs, and malonyl ginsenosides treatment significantly increased the amount the body glucose tolerance and improved insulin resistance.
Malonyl ginsenosides reduced body weight, serum triglyceride (TG) and total cholesterol (TC) levels in diabetic rats, the level of TC was significantly lower than model group (P<0.05). It suggested that malonyl ginsenosides improved the disorder of the serum lipid metabolism.
The achievements of this research are as follows:
On the basis of the physical constants, chemical evidence and spectrum analysis[IR、LCQ-MS HR-SI-MS.'H NMR、13C NMR and 2D NMR (HSQC and HMBC)], a new compound, Malonyl ginsenoside-Ra3 elucidated as 3-0-(6-O-malonyl-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside)-20-0-β-D-xylopyranosyl (1→3)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside-20(s)-protopanaxadiol.
The contents of 10 ginsenosides (m-Rb1,m-Rb2, m-Rc, m-Rd, Rg1, Re, Rb1, Rc, Rb2, Rd) in different growing seasons and ages of Panax ginseng were quantified by high-performance liquid chromatography coupled with UV-vis detector. The results show that the content of malonyl ginsenosides present between 44 and 59% of total ginsenosides, with several exceptions, malonyl ginsenosides in most of harvests and ages are slightly higher than six ginsenosides.
We studied the effect of MGR on improvement of glycemia, lipid metabolism and the insulin resistance in Type 2 Diabetes Mellitus Rats (T2DM). The results suggested that MGR could decrease the blood glucose, improve the disorder of the serum lipid metabolism and Insulin sensitivity in T2DM rats.
引文
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