CN111388491A - Rare monomer ginsenoside composition and its preparation method - Google Patents
Rare monomer ginsenoside composition and its preparation method Download PDFInfo
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- CN111388491A CN111388491A CN202010383844.4A CN202010383844A CN111388491A CN 111388491 A CN111388491 A CN 111388491A CN 202010383844 A CN202010383844 A CN 202010383844A CN 111388491 A CN111388491 A CN 111388491A
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- Prior art keywords
- rare
- ginsenoside
- parts
- composition
- rare ginsenoside
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- 229930182494 ginsenoside Natural products 0.000 title claims abstract description 234
- 229940089161 ginsenoside Drugs 0.000 title claims abstract description 209
- 239000000203 mixture Substances 0.000 title claims abstract description 149
- 239000000178 monomer Substances 0.000 title claims abstract description 94
- 238000002360 preparation method Methods 0.000 title claims abstract description 57
- RWXIFXNRCLMQCD-JBVRGBGGSA-N (20S)-ginsenoside Rg3 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O RWXIFXNRCLMQCD-JBVRGBGGSA-N 0.000 claims abstract description 70
- XIRZPICFRDZXPF-UHFFFAOYSA-N Ginsenoside Rg3 Natural products CC(C)=CCCC(C)(O)C1CCC(C2(CC(O)C3C4(C)C)C)(C)C1C(O)CC2C3(C)CCC4OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O XIRZPICFRDZXPF-UHFFFAOYSA-N 0.000 claims abstract description 67
- PYXFVCFISTUSOO-UHFFFAOYSA-N betulafolienetriol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC(C(C)(O)CCC=C(C)C)C4C(O)CC3C21C PYXFVCFISTUSOO-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000605 extraction Methods 0.000 claims abstract description 27
- CKUVNOCSBYYHIS-UHFFFAOYSA-N (20R)-ginsenoside Rg3 Natural products CC(C)=CCCC(C)(O)C1CCC(C2(CCC3C4(C)C)C)(C)C1C(O)CC2C3(C)CCC4OC1OC(CO)C(O)C(O)C1O CKUVNOCSBYYHIS-UHFFFAOYSA-N 0.000 claims abstract description 26
- CKUVNOCSBYYHIS-IRFFNABBSA-N (20S)-ginsenoside Rh2 Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CKUVNOCSBYYHIS-IRFFNABBSA-N 0.000 claims abstract description 26
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- NJUXRKMKOFXMRX-RNCAKNGISA-N Ginsenoside Rg5 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(/C)=C/CC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O NJUXRKMKOFXMRX-RNCAKNGISA-N 0.000 claims abstract description 24
- NJUXRKMKOFXMRX-AXUZFSSLSA-N ginsenoside Rg5 Natural products CC(=CCC=C(C)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]3[C@@]4(C)CC[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]4CC[C@@]23C)C NJUXRKMKOFXMRX-AXUZFSSLSA-N 0.000 claims abstract description 24
- NJUXRKMKOFXMRX-UHFFFAOYSA-N ginsenoside Rz1 Natural products CC(C)=CCC=C(C)C1CCC(C2(CCC3C4(C)C)C)(C)C1C(O)CC2C3(C)CCC4OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O NJUXRKMKOFXMRX-UHFFFAOYSA-N 0.000 claims abstract description 24
- WMGBQZAELMGYNO-YMWSGFAJSA-N (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-[[(3s,5r,8r,9r,10r,12r,13r,14r,17s)-12-hydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]oxane-3,4,5-triol Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(=C)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O WMGBQZAELMGYNO-YMWSGFAJSA-N 0.000 claims abstract description 23
- UZRSSXUIXNCYLP-UHFFFAOYSA-N Ginsenoside Rk2 Natural products CC(=CCCC(=C)C1CCC2(C)C1C(O)CC3C4(C)CCC(OC5CC(O)C(O)C(CO)O5)C(C)(C)C4CCC23C)C UZRSSXUIXNCYLP-UHFFFAOYSA-N 0.000 claims abstract description 23
- KWDWBAISZWOAHD-MHOSXIPRSA-N (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-[[(3s,5r,8r,9r,10r,12r,13r,14r,17s)-12-hydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]o Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(=C)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KWDWBAISZWOAHD-MHOSXIPRSA-N 0.000 claims abstract description 21
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- PHLXREOMFNVWOH-YAGNRYSRSA-N Ginsenoside Rh3 Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(\C)=C/CC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PHLXREOMFNVWOH-YAGNRYSRSA-N 0.000 claims abstract description 15
- PHLXREOMFNVWOH-DNQFHFKUSA-N Ginsenoside Rh3 Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1C(C)(C)[C@H]2[C@@](C)([C@@H]3[C@](C)([C@@]4(C)[C@H]([C@H](O)C3)[C@@H](/C(=C/C/C=C(\C)/C)/C)CC4)CC2)CC1 PHLXREOMFNVWOH-DNQFHFKUSA-N 0.000 claims abstract description 15
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Abstract
The invention discloses a rare monomer ginsenoside composition, which comprises one or more of rare ginsenoside Rg3, rare ginsenoside Rg5, rare ginsenoside Rh2, rare ginsenoside Rh3, rare ginsenoside Rk1, rare ginsenoside Rk2, rare ginsenoside aPPD and rare ginsenoside aPPT. The rare monomer ginsenoside composition can improve the functions and the immune function of a human body; the product can not be left in human body, has no side effect on human body, and can be well absorbed by human body through intestinal tract. By the extraction method of the rare ginsenoside Rg3, the rare ginsenoside Rg3 with higher purity can be prepared without inert gas protection or heating condition; the preparation product prepared by the invention is placed for 7 days or even 30 days, has no serious deformation, cracking, powdering or abnormal color, and has good stability.
Description
Technical Field
The invention belongs to the field of functional foods and medicines, and particularly relates to a rare monomer ginsenoside composition and a preparation method thereof.
Background
In recent years, the incidence of cancer in China is on the rise, about 300 million people suffer from cancer every year, and the research of various anti-cancer health-care foods becomes a research hotspot at present. Ginseng (Panax ginseng C.A. Mey), which is otherwise known as Huangshen, Dijing and Shencao, is a perennial herb plant of Panax of Araliaceae of Umbelliferae, called "king of Baicao", and has excellent anticancer activity. The main active component of the compound is ginsenoside, which belongs to triterpenes. The rare ginsenoside is a secondary metabolic derivative generated after the ginsenoside is converted, and has stronger biological activity.
At present, rare ginsenoside products rarely exist in the market, and are single or combination of two, the function is single, and products with multiple-effect functions are rarely available; in the extraction method of the rare ginsenoside Rg3 in the prior art, inert gas protection or high-temperature heating condition is often needed, and the purity of the rare ginsenoside is not high; meanwhile, the existing rare ginsenoside preparation has the problems of poor stability, insufficient structural stability, easy deformation after long-time placement, even loss of effective components and the like. Therefore, a new and rare monomer ginsenoside composition is needed.
Disclosure of Invention
In order to solve the above problems, the present invention provides in a first aspect a rare monomeric ginsenoside composition comprising one or more combinations of rare ginsenosides Rg3, Rg5, Rh2, Rh3, Rk1, Rk2, aappd, and alppt.
As a preferable technical scheme, the composition comprises, by weight, 0.5-30 parts of rare ginsenoside Rg3, 1-10 parts of rare ginsenoside Rg5, 0.5-5 parts of rare ginsenoside Rh2, 1-10 parts of rare ginsenoside Rh3, 1-5 parts of rare ginsenoside Rk1, 1-10 parts of rare ginsenoside Rk2, 1-20 parts of rare ginsenoside aPPD and 1-10 parts of rare ginsenoside aPPT.
As a preferable technical scheme, the method for extracting the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to the weight parts, 1-10 parts of ginseng is crushed, 1-10 parts of solvent type degreasing agent is added, the mixture is degreased and filtered, filter residue is collected, 5-40 parts of water is added, and the mixture is uniformly mixed to obtain a mixed water solution;
step two: adding a pH regulator into the mixed aqueous solution obtained in the step one to regulate the pH to 5.5-6.5, adding biological enzyme, continuously adding 3-30 parts of water, uniformly mixing, adding a polyhydroxy compound, stirring and reacting at 20-30 ℃ for 5-10 h, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.05-0.07 Mpa and temperature of 20-40 ℃ to obtain a concentrated solution;
and step three, adsorbing the concentrated solution obtained in the step two by using a polystyrene resin chromatographic column at the flow rate of 20-40 m L/min, washing impurities by using deionized water and (10-30) wt% of ethanol respectively, eluting by using (70-90) wt% of ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 20-30 ℃ to obtain ginsenoside Rg 3.
As a preferable technical scheme, the pH adjusting agent in the second step is selected from one or more of acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, oxalic acid, citric acid, malic acid, monofluoroacetic acid, difluoroacetic acid, trifluoroacetic acid, monochloroacetic acid, dichloroacetic acid and trichloroacetic acid.
As a preferred technical solution, the biological enzyme in the second step is selected from one or more of cellulase, hemicellulase, proteolytic enzyme, pectinase and lactase.
As a preferable technical scheme, the polyhydroxy compound in the second step is selected from one or more of vitamin C, vitamin C glucoside, vitamin C phosphate, sodium vitamin C phosphate and magnesium vitamin C phosphate.
The second aspect of the invention provides a rare ginsenoside preparation prepared from the rare monomer ginsenoside composition, and the preparation raw materials comprise 60-80 parts by weight of rare monomer ginsenoside composition and 300-400 parts by weight of polysaccharide.
As a preferred technical scheme, the polysaccharide is a polysaccharide containing 2-10 glycosidic bonds.
As a preferred technical scheme, the rare ginsenoside preparation also comprises auxiliary materials as raw materials for preparation.
The third aspect of the invention provides an application of a rare ginsenoside preparation prepared from the rare monomer ginsenoside composition, which is applied to capsules, tablets, soft capsules, liquid, granules, dry powder, oral liquid, pills, paste and gels.
Has the advantages that: the rare monomer ginsenoside composition can improve the functions of human bodies and immunity, enhance the phagocytic function of mononuclear macrophage NK cells and neutrophil granulocytes and the proliferation and differentiation function of lymphocytes; the product can not be left in human body, has no side effect on human body, and can be well absorbed by human body through intestinal tract. By the extraction method of the rare ginsenoside Rg3, the rare ginsenoside Rg3 with higher purity can be prepared without inert gas protection or heating condition; the preparation product prepared by the invention is placed for 7 days or even 30 days, has no serious deformation, cracking, powdering or abnormal color, and has good stability.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the description of the embodiments are briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
FIG. 1 is a schematic view of the molecular structure of the rare ginsenoside Rg 3;
FIG. 2 is a schematic view of the molecular structure of the rare ginsenoside Rg 5;
FIG. 3 is a schematic view of the molecular structure of the rare ginsenoside Rh 2;
FIG. 4 is a schematic view of the molecular structure of the rare ginsenoside Rh 3;
FIG. 5 is a schematic view of the molecular structure of the rare ginsenoside Rk 1;
FIG. 6 is a schematic view of the molecular structure of the rare ginsenoside Rk 2;
FIG. 7 is a schematic view of the molecular structure of the rare ginsenoside aPPD (S);
FIG. 8 is a schematic view of the molecular structure of the rare ginsenoside aPPT (S);
FIG. 9 is a schematic diagram of the rare monomer ginsenoside composition obtained in example 1 of the present invention phagocytosing chicken red blood cells by macrophages in abdominal cavity of nude mice.
① -chicken erythrocyte which is not phagocytized, ② -nude mouse abdominal cavity macrophage which is phagocytosed by chicken erythrocyte.
Detailed Description
The technical features of the technical solutions provided by the present invention are further clearly and completely described below with reference to the specific embodiments, and the scope of protection is not limited thereto.
The words "preferred", "more preferred", and the like, in the present invention refer to embodiments of the invention that may provide certain benefits, under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
In order to solve the above problems, the present invention provides in a first aspect a rare monomeric ginsenoside composition comprising one or more combinations of rare ginsenosides Rg3, Rg5, Rh2, Rh3, Rk1, Rk2, aappd, and alppt.
< ginsenoside >
Ginseng (Panax ginseng C.A. Mey), which is otherwise known as Huangshen, Dijing and Shencao, is a perennial herb of Panax of Araliaceae of Umbelliferae. It includes ginseng (p.ginseng), american ginseng (p.quequefolius), panax notoginseng (p.notoginseng), panax japonicus (p.uaponicus) and other varieties.
[ EFFECT ]: tonify primordial qi, recover pulse to stop collapse, tonify spleen and lung, promote fluid production, and induce tranquilization.
[ INDICATIONS ]: asthenia, collapse, cold limbs, weak pulse, spleen deficiency, anorexia, lung deficiency, cough, asthma, body fluid deficiency, thirst, internal heat, asthenia, palpitation, insomnia, sexual impotence, and cold womb; heart failure, cardiogenic shock; can be used for treating short breath, dyspnea, palpitation, amnesia, thirst, hyperhidrosis, anorexia, asthenia, acute and chronic diseases, and shock and collapse caused by blood loss; to reinforce primordial qi, relieve collapse and promote fluid production, tranquilize mind; it is indicated for deficiency due to overstrain, poor appetite, lassitude, regurgitation, diarrhea, cough, dyspnea, spontaneous sweating, palpitation, amnesia, vertigo, headache, impotence, frequent micturition, diabetes, metrorrhagia, metrostaxis, chronic infantile convulsion, and deficiency of both qi and blood.
Ginsenosides, i.e., ginsenosides, are mainly found in ginseng, are the main active ingredients in ginseng, and belong to steroid compounds.
The rare monomer ginsenoside is a secondary metabolic derivative generated after the ginsenoside is converted, and has stronger biological activity. The ginseng is not particularly limited, and Chinese ginseng, Korean ginseng, American ginseng and pseudo-ginseng can be selected, and the production area of the ginseng is also not particularly limited, such as American ginseng produced in Canada.
The rare monomer ginsenoside is named according to R in thin layer chromatographyfThe values (specific shift values) are named as Ro, Ra, Rb1, Rb3, Rc, Rf, Rg1, Rg2, Rg3, Rg5, Rh1, Rh2, Rh3, Rk1 and Rk2 from small to large. The rare ginsenoside aPPD belongs to dammarane type tetracyclic triterpenoid ginsenoside compounds, and the carbons of the rare ginsenoside aPPD after the prototype of the rare ginsenoside is 20 are connected by a direct connection type structure, so the rare ginsenoside aPPD is called 20(S) -PPD or 20(R) -PPD; wherein 20(S) -PPD, aPPD (S), the 20-hydroxy group can be subjected to configuration transformation to generate 20(R) -PPD, namely aPPD (R); preferably, the rare ginsenoside aPPD is aPPD (S). The rare ginsenoside aPPT also comprises 20(S) -PPT and 20(R) -PPT; 20(S) -PPT, aPPT (S), wherein the hydroxyl at position 20 can be subjected to configuration transformation to generate 20(R) -PPT; preferably, the rare ginsenoside aPPT is aPPT (S). The rare ginsenoside Rg3, the rare ginsenoside Rg5, the rare ginsenoside Rh2, the rare ginsenoside Rh3, the rare ginsenoside Rk1, the rare ginsenoside Rk2, the rare ginsenoside aPPD and the rare ginsenoside aPPT have the structural formulas shown in the attached drawings 1-8.
In a preferred embodiment, the rare monomeric ginsenoside composition comprises rare ginsenoside Rg3, rare ginsenoside Rg5, rare ginsenoside Rh2, rare ginsenoside Rh3, rare ginsenoside Rk1, rare ginsenoside Rk2, rare ginsenoside ppd, rare ginsenoside aPPT.
In a more preferred embodiment, the composition comprises, by weight, 0.5 to 30 parts of rare ginsenoside Rg3, 1 to 10 parts of rare ginsenoside Rg5, 0.5 to 5 parts of rare ginsenoside Rh2, 1 to 10 parts of rare ginsenoside Rh3, 1 to 5 parts of rare ginsenoside Rk1, 1 to 10 parts of rare ginsenoside Rk2, 1 to 20 parts of rare ginsenoside aPPD, and 1 to 10 parts of rare ginsenoside aPPT.
In a further preferred embodiment, the composition comprises, by weight parts, 30 parts rare ginsenoside Rg3, 10 parts rare ginsenoside Rg5, 5 parts rare ginsenoside Rh2, 10 parts rare ginsenoside Rh3, 5 parts rare ginsenoside Rk1, 5 parts rare ginsenoside Rk2, 20 parts rare ginsenoside ppd, 10 parts rare ginsenoside aptt.
The inventor finds that the system has extremely high antitumor activity when 0.5-30 parts of rare ginsenoside Rg3, 1-10 parts of rare ginsenoside Rg5, 0.5-5 parts of rare ginsenoside Rh2, 1-10 parts of rare ginsenoside Rh3, 1-5 parts of rare ginsenoside Rk1 and 1-10 parts of rare ginsenoside Rk2 are adopted in the process of continuous exploration. The inventor conjectures that the rare ginsenoside Rh2 can block the biosynthesis of RNA and protein in the G1 phase of the reproductive cycle of tumor cells, and cooperates with the inhibiting effect of a certain proportion of rare ginsenoside Rg5 and rare ginsenoside Rg3 on the G2 phase of the reproductive cycle of the tumor cells to inhibit the synthesis of protein and ATP in the mitosis prophase of the tumor cells so as to slow down the proliferation and growth speed of the tumor cells; meanwhile, the rare ginsenoside Rg5 and the rare ginsenoside Rg3 can also prevent the adhesion and infiltration of tumor cells to fibronectin and laminin, and inhibit the proliferation of vascular endothelial cells and the formation of tumor neovascularization. The rare ginsenoside Rk1 and Rk2 can cooperate with rare ginsenoside Rh2 to promote reverse transformation of tumor cells and form differentiation to normal cells. However, the inventors have also found that when such rare ginsenoside compositions are used, they cause central nervous system hyperexcitability, which tends to cause irritability, impulsivity and variable mood.
The inventor finds that when 1-20 parts of rare ginsenoside aPPD and 1-10 parts of rare ginsenoside aPPT are combined with the composition, the problem of central nervous hyperexcitability can be solved, and the antitumor activity of the system can be further improved. The inventor conjectures the possible reason that, on one hand, a certain proportion of rare ginsenoside aPPD and rare ginsenoside aPPT cooperate with the rare ginsenoside to directly exert toxic action on tumor cells, provide an action target point for cancer suppressor genes and promote the apoptosis of the tumor cells; on the other hand, the medicine can also protect neurons from being invaded by toxic substances of tumor cells, promote immune cells to generate cytokines, improve the functions of a human body and immunity, and enhance the phagocytic function of mononuclear macrophage NK cells and neutrophils and the proliferation and differentiation function of lymphocytes. The composition does not remain in human body, has no side effect on human body, and can be well absorbed by human body through intestinal tract.
(rare ginsenoside Rg3)
In a preferred embodiment, the method for extracting the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to the weight parts, 1-10 parts of ginseng is crushed, 1-10 parts of solvent type degreasing agent is added, the mixture is degreased and filtered, filter residue is collected, 5-40 parts of water is added, and the mixture is uniformly mixed to obtain a mixed water solution;
step two: adding a pH regulator into the mixed aqueous solution obtained in the step one to regulate the pH to 5.5-6.5, adding biological enzyme, continuously adding 3-30 parts of water, uniformly mixing, adding a polyhydroxy compound, stirring and reacting at 20-30 ℃ for 5-10 h, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.05-0.07 Mpa and temperature of 20-40 ℃ to obtain a concentrated solution;
and step three, adsorbing the concentrated solution obtained in the step two by using a polystyrene resin chromatographic column at the flow rate of 20-40 m L/min, washing impurities by using deionized water and (10-30) wt% of ethanol respectively, eluting by using (70-90) wt% of ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 20-30 ℃ to obtain ginsenoside Rg 3.
In a more preferred embodiment, the method for extracting the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to parts by weight, 5 parts of ginseng is crushed, 5 parts of solvent type degreasing agent is added for mixing and degreasing, then the mixture is filtered, filter residue is collected and 20 parts of water are added for mixing uniformly, and mixed water solution is obtained;
step two: adding a pH regulator into the mixed aqueous solution obtained in the step one to regulate the pH value to 6, adding biological enzyme, continuously adding 15 parts of water, uniformly mixing, adding a polyhydroxy compound, stirring and reacting at 25 ℃ for 8 hours, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.06Mpa and temperature of 30 ℃ to obtain concentrated solution;
and step three, adsorbing the concentrated solution obtained in the step two by using a polystyrene resin chromatographic column at the flow rate of 30m L/min, washing impurities by using deionized water and 20 wt% of ethanol respectively, eluting by using 80 wt% of ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 25 ℃ to obtain the ginsenoside Rg 3.
Solvent type degreasing agent
In a preferred embodiment, the solvent-based degreasing agent is selected from one or more of petroleum ether, gasoline, kerosene, trichloroethylene and dichloromethane.
In a preferred embodiment, the solvent-based degreaser is petroleum ether.
pH regulator
In a preferred embodiment, the pH regulator in step two is selected from the group consisting of acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, oxalic acid, citric acid (CAS number 77-92-9), malic acid (CAS number 6915-15-7), monofluoroacetic acid (CAS number 144-49-0), difluoroacetic acid (CAS number 381-73-7), trifluoroacetic acid (CAS number 76-05-1), monochloroacetic acid (CAS number 79-11-8), dichloroacetic acid (CAS number 79-43-6), trichloroacetic acid (CAS number 76-03-9).
In a more preferred embodiment, the pH adjusting agent in step two is selected from one or more of acetic acid, hydrochloric acid, phosphoric acid, oxalic acid, citric acid, and malic acid.
In a further preferred embodiment, the pH adjusting agent in step two is acetic acid.
Biological enzymes
In a preferred embodiment, the biological enzyme in the second step is selected from one or more of cellulase, hemicellulase, proteolytic enzyme, pectinase and lactase.
Examples of hemicellulases include, but are not limited to: mannanase, xylanase and polygalacturonase.
As examples of proteolytic enzymes, include, but are not limited to: papain, chymopapain A, chymopapain B, and papain B.
As examples of pectinases, including but not limited to: polymethylgalactanase, pectin lyase, pectate lyase, polygalacturonase, polygalacturonate lyase.
In a more preferred embodiment, the biological enzyme in step two is a cellulase and/or a proteolytic enzyme.
In a further preferred embodiment, the biological enzymes in step two are cellulase and proteolytic enzymes.
In a preferred embodiment, the weight ratio of the cellulase to the proteolytic enzyme is (0.5-2): 1.
in a more preferred embodiment, the cellulase (CAS number 9012-54-8) and proteolytic enzyme are present in a weight ratio of 1: 1.
in a preferred embodiment, the proteolytic enzyme is papain (CAS number 9001-73-4).
Polyhydroxy compounds
In a preferred embodiment, the polyhydroxy compound in step two is selected from one or more of vitamin C (CAS number 50-81-7), vitamin C glycoside (CAS number 129499-78-1), vitamin C phosphate (CAS number 23313-12-4), sodium vitamin C phosphate (CAS number 66170-10-3), magnesium vitamin C phosphate (CAS number 113170-55-1).
In a more preferred embodiment, the polyol in step two is vitamin C.
In a preferred embodiment, the weight ratio of the biological enzyme to the polyol is 1: (0.2-0.5).
In a more preferred embodiment, the weight ratio of the biological enzyme to the polyol is 1: 0.35.
polystyrene resin
In a preferred embodiment, the polystyrene resin is a polystyrene resin containing phenolic hydroxyl groups and/or a polystyrene-divinylbenzene adsorbent resin.
In a more preferred embodiment, the polystyrene resin is a polystyrene-divinylbenzene adsorbent resin.
The polystyrene-divinylbenzene adsorption resin is HP20 polystyrene-divinylbenzene adsorption resin which is purchased from Mitsubishi Japan.
In a preferred embodiment, the volume ratio of 80 wt% ethanol, 20 wt% ethanol and deionized water in the third step is 1: (0.5-1): (1-2).
In a more preferred embodiment, the volume ratio of 80 wt% ethanol, 20 wt% ethanol and deionized water in the third step is 1: 0.75: 1.25.
the inventor finds that when the pH value of the solution is adjusted to 5.5-6.5, the weight ratio of the biological enzyme is (0.5-2): 1 cellulase and proteolytic enzyme, and a certain proportion of polyhydroxy compound is used, when the adsorption is carried out by a polystyrene resin chromatographic column, inert gas protection or high-temperature heating condition is not needed, and the rare ginsenoside Rg3 with higher purity can be prepared. The inventor believes that under the condition that the pH is 5.5-6.5, a specific dienol structure in a molecule of a polyhydroxy compound can catalyze cellulase and proteolytic enzyme in a certain proportion to a certain extent, the cellulase is promoted to hydrolyze insoluble cellulose in the cell wall of the ginseng into glucose, so that effective components in the ginseng cell flow out, and the effective components of the ginseng are hydrolyzed by cysteine contained in the active center of the papain to be converted into rare ginsenoside Rg 3; active hydroxyl groups of molecules of the polyhydroxy compounds can also protect the formed rare ginsenoside Rg3 to a certain extent, so that the yield is further improved; further, by adsorption through a polystyrene resin chromatographic column and by adopting a specific extraction solvent and an elution process, the components such as volatile oil, saccharides and the like are separated by utilizing different adsorption and desorption acting forces of the adsorbent on different structural substances, so that the purity of the rare ginsenoside Rg3 is improved.
The extraction methods of the rare ginsenoside Rg5, the rare ginsenoside Rh2, the rare ginsenoside Rh3, the rare ginsenoside Rk1, the rare ginsenoside Rk2, the rare ginsenoside aPPD and the rare ginsenoside aPPT are not particularly limited, and the rare ginsenosides can be obtained commercially, for example, from Nanjing spring and autumn bioengineering Co., Ltd, and various extraction methods known to those skilled in the art can be adopted, for example, the following steps can be adopted: according to the weight parts, 1-2 parts of ginseng are crushed, 10-20 parts of 60-98 wt% ethanol is added for cold soaking extraction, macroporous resin adsorption column separation is carried out after hydrolysis treatment, 60-75 wt% ethanol is added for elution after impurity washing by distilled water, the obtained eluent is subjected to reduced pressure concentration and drying, and the steps can be adjusted according to the required rare ginsenoside.
The second aspect of the invention provides a rare ginsenoside preparation prepared from the rare monomer ginsenoside composition, and the preparation raw materials comprise 60-80 parts by weight of rare monomer ginsenoside composition and 300-400 parts by weight of polysaccharide.
In a preferred embodiment, the rare ginsenoside preparation prepared from the rare monomer ginsenoside composition comprises 70 parts by weight of rare monomer ginsenoside composition and 350 parts by weight of polysaccharide.
< polysaccharides >
In a preferred embodiment, the polysaccharide is a polysaccharide having 2 to 10 glycosidic linkages.
In a preferred embodiment, the polysaccharide containing 2-10 glycosidic linkages is selected from the group consisting of xylo-oligosaccharide, dextrin, chitin (CAS number 1398-61-4), raffinose (CAS number 512-69-6), stachyose (CAS number 10094-58-3) in combination with one or more thereof.
As examples of xylo-oligosaccharides, including but not limited to: xylobiose (CAS number 6860-47-5), xylotriose (CAS number 47592-59-6), xylotetraose (CAS number 22416-58-6), and xylohexaose (CAS number 49694-21-5).
Examples of dextrins include, but are not limited to: cyclodextrin, maltodextrin.
In a preferred embodiment, the polysaccharide having 2 to 10 glycosidic linkages is a cyclodextrin.
In a preferred embodiment, the cyclodextrin is selected from the group consisting of α -cyclodextrin, β -cyclodextrin, γ -cyclodextrin, or a combination of one or more thereof.
In a more preferred embodiment, the cyclodextrin is selected from the group consisting of β -cyclodextrin (CAS number: 7585-39-9), hydroxypropyl- β -cyclodextrin (CAS number: 128446-35-5), hydroxyethyl- β -cyclodextrin (CAS number: 128446-32-2) in combination with one or more thereof.
In a further preferred embodiment, the cyclodextrin is hydroxypropyl- β -cyclodextrin.
The inventor finds that when a composition consisting of one or more of rare ginsenoside Rg3, rare ginsenoside Rg5, rare ginsenoside Rh2, rare ginsenoside Rh3, rare ginsenoside Rk1, rare ginsenoside Rk2, rare ginsenoside aPPD and rare ginsenoside aPPT is prepared into a preparation in the actual production process, the obtained preparation has poor stability and insufficient structural stability, and is easy to deform after being placed for a long time, even leads to loss of effective components. When a polysaccharide having 2 to 10 glycosidic bonds, particularly cyclodextrin, is used, the above phenomenon can be effectively improved. The inventors believe that the cyclodextrin molecular cavities can contain and protect the rare ginsenoside composition and promote good dispersion of the rare ginsenoside composition in the formulation; meanwhile, intermolecular acting force is formed among special groups on cyclodextrin molecules and other auxiliary materials, so that the stability of the rare ginsenoside composition in a system is improved; and the polysaccharide with 2-10 glycosidic bonds can also improve the adhesion among the components of the preparation, improve the structural stability of the preparation, and is not easy to deform and lose effective components after being placed for a long time.
In a preferred embodiment, the rare ginsenoside preparation is prepared from raw materials which also comprise auxiliary materials.
< auxiliary materials >
The invention has no special limitation on the auxiliary materials, and can be adjusted according to the type and the actual requirement of the preparation. Examples include, but are not limited to, adsorbents, binders, lubricants, dispersants, wetting agents, disintegrants, flavorants, colorants, flavorants, bacteriostats, preservatives, adhesives, stabilizers, transdermal enhancers, suspending agents, co-solvents, buffers, emulsifiers, humectants.
The third aspect of the invention provides an application of a rare ginsenoside preparation prepared from the rare monomer ginsenoside composition, which is applied to capsules, tablets, soft capsules, liquid, granules, dry powder, oral liquid, pills, paste and gels.
Examples of tablets include, but are not limited to: plain tablets, coated tablets, sustained-release tablets, dispersible tablets, buccal tablets and chewable tablets.
Examples of liquid formulations include, but are not limited to: drop, decoction, syrup, injection, liniment, spray, and lotion.
Examples of pills include, but are not limited to: dripping pill, honeyed pill, paste pill, or concentrated pill.
Examples of pastes include, but are not limited to: ointment formula and ointment.
The method for preparing the formulation of the present invention is not particularly limited, and various methods for preparing formulations well known to those skilled in the art can be used.
The present invention will now be described in detail by way of examples, and the starting materials used are commercially available unless otherwise specified.
Examples
Example 1
Example 1 provides a rare monomer ginsenoside composition comprising, by weight, 30 parts rare ginsenoside Rg3, 10 parts rare ginsenoside Rg5, 5 parts rare ginsenoside Rh2, 10 parts rare ginsenoside Rh3, 5 parts rare ginsenoside Rk1, 5 parts rare ginsenoside Rk2, 20 parts rare ginsenoside appd(s), 10 parts rare ginsenoside appt(s). The rare ginsenoside Rg5, Rh2, Rh3, Rk1, Rk2, aPPD (S), aPPT (S) are purchased from Nanjing Chunqiu bioengineering Co., Ltd.
The extraction method of the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to the weight portion, 5 portions of ginseng are crushed, 5 portions of petroleum ether are added for mixing and degreasing, then filtration is carried out, filter residue is collected and is added with 20 portions of water for even mixing, and mixed water solution is obtained;
step two: adding acetic acid into the mixed aqueous solution obtained in the step one to adjust the pH value to 6, adding biological enzyme, continuously adding 15 parts of water, uniformly mixing, adding vitamin C, stirring and reacting at 25 ℃ for 8 hours, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.06Mpa and temperature of 30 ℃ to obtain concentrated solution; the biological enzyme is cellulase and papain, and the weight ratio of the cellulase to the papain is 1: 1; the weight ratio of the biological enzyme to the vitamin C is 1: 0.35;
and step three, adsorbing the concentrated solution obtained in the step two by using an HP20 polystyrene-divinylbenzene adsorbent resin chromatographic column at the flow rate of 30m L/min, washing impurities by using deionized water and 20 wt% of ethanol respectively, eluting by using 80 wt% of ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 25 ℃ to obtain ginsenoside Rg3, wherein the volume ratio of the 80 wt% of ethanol to the 20 wt% of ethanol to the deionized water is 1: 0.75: 1.25.
The present invention also provides a rare ginsenoside granule prepared from the rare monomer ginsenoside composition, wherein the raw materials for preparing the rare monomer ginsenoside composition comprise 70 parts by weight of the rare monomer ginsenoside composition and 350 parts by weight of hydroxypropyl- β -cyclodextrin.
The preparation method of the granules comprises the following steps of mixing the rare monomer ginsenoside composition and hydroxypropyl- β -cyclodextrin, adding deionized water, adjusting to slurry with the solid content of 10 wt%, then carrying out spray drying on the obtained slurry to prepare powder, adding starch according to 25% of the total mass of the obtained composition powder after the air inlet temperature is 170 ℃ and the air outlet temperature is 90 ℃ to obtain the composition powder, preparing granules by adopting a fluidized bed granulation method, and drying to obtain the granules.
Example 2
Example 2 provides a rare monomer ginsenoside composition comprising, by weight, 0.5 parts rare ginsenoside Rg3, 1 part rare ginsenoside Rg5, 0.5 parts rare ginsenoside Rh2, 1 part rare ginsenoside Rh3, 1 part rare ginsenoside Rk1, 1 part rare ginsenoside Rk2, 1 part rare ginsenoside aPPD (S), 1 part rare ginsenoside aPPT (S). The rare ginsenoside Rg5, Rh2, Rh3, Rk1, Rk2, aPPD (S), aPPT (S) are purchased from Nanjing Chunqiu bioengineering Co., Ltd.
The extraction method of the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to the weight portion, 1 portion of ginseng is crushed, 1 portion of petroleum ether is added for mixing and degreasing, then the filtering is carried out, the filter residue is collected and added with 5 portions of water for mixing evenly, and a mixed water solution is obtained;
step two: adding acetic acid into the mixed aqueous solution obtained in the step one to adjust the pH value to 5.5, adding biological enzyme, continuously adding 3 parts of water, uniformly mixing, adding vitamin C, stirring and reacting at 20 ℃ for 5 hours, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.05Mpa and temperature of 20 ℃ to obtain concentrated solution; the biological enzyme is cellulase and papain, and the weight ratio of the cellulase to the papain is 0.5: 1; the weight ratio of the biological enzyme to the vitamin C is 1: 0.2;
and step three, adsorbing the concentrated solution obtained in the step two by using an HP20 polystyrene-divinylbenzene adsorbent resin chromatographic column at the flow rate of 2m L/min, washing impurities by using deionized water and 10 wt% of ethanol respectively, eluting by using 70 wt% of ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 20 ℃ to obtain ginsenoside Rg3, wherein the volume ratio of the 70 wt% of ethanol to the 10 wt% of ethanol to the deionized water in the step three is 1: 0.5: 1.
The present invention also provides a rare ginsenoside granule prepared from the rare monomer ginsenoside composition, wherein the preparation raw materials comprise 60 parts by weight of the rare monomer ginsenoside composition and 300 parts by weight of polysaccharide.
The preparation method of the granules is the same as that of example 1.
Example 3
Example 3 provides a rare monomer ginsenoside composition comprising, by weight, 30 parts rare ginsenoside Rg3, 10 parts rare ginsenoside Rg5, 5 parts rare ginsenoside Rh2, 10 parts rare ginsenoside Rh3, 5 parts rare ginsenoside Rk1, 10 parts rare ginsenoside Rk2, 20 parts rare ginsenoside appd(s), 10 parts rare ginsenoside appt(s). The rare ginsenoside Rg5, Rh2, Rh3, Rk1, Rk2, aPPD (S), aPPT (S) are purchased from Nanjing Chunqiu bioengineering Co., Ltd.
The extraction method of the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to the weight portion, 10 portions of ginseng are crushed, 10 portions of petroleum ether are added for mixing and degreasing, then the filtering is carried out, filter residues are collected and added with 40 portions of water for even mixing, and mixed water solution is obtained;
step two: adding acetic acid into the mixed aqueous solution obtained in the step one to adjust the pH value to 6.5, adding biological enzyme, continuously adding 30 parts of water, uniformly mixing, adding vitamin C, stirring and reacting at 30 ℃ for 10 hours, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.07Mpa and temperature of 40 ℃ to obtain concentrated solution; the biological enzyme is cellulase and papain, and the weight ratio of the cellulase to the papain is 2: 1; the weight ratio of the biological enzyme to the vitamin C is 1: 0.5;
and step three, adsorbing the concentrated solution obtained in the step two by using an HP20 polystyrene-divinylbenzene adsorbent resin chromatographic column at the flow rate of 40m L/min, washing impurities by using deionized water and 30 wt% ethanol respectively, eluting by using 90 wt% ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 30 ℃ to obtain ginsenoside Rg3, wherein the volume ratio of 80 wt% ethanol to 20 wt% ethanol to deionized water in the step three is 1 (0.5-1) to 1-2.
The present invention also provides a rare ginsenoside granule prepared from the rare monomer ginsenoside composition, wherein the preparation raw materials comprise 80 parts by weight of the rare monomer ginsenoside composition and 400 parts by weight of polysaccharide.
The preparation method of the granules is the same as that of example 1.
Example 4
Example 4 provides a rare monomer ginsenoside composition, which is embodied in the same manner as in example 1.
This example also provides a dry powder of rare ginsenosides prepared from the rare monomer ginsenoside composition, which is prepared from the rare monomer ginsenoside composition 70 parts by weight and hydroxypropyl- β -cyclodextrin 350 parts by weight.
The preparation method of the dry powder comprises the following steps of mixing a rare monomer ginsenoside composition and hydroxypropyl- β -cyclodextrin, adding deionized water, adjusting to a slurry with the solid content of 10 wt%, then carrying out spray drying on the obtained slurry to obtain powder, adding starch according to 40% of the total mass of the obtained composition powder after the air inlet temperature is 170 ℃ and the air outlet temperature is 90 ℃ to obtain the composition powder, preparing the powder by adopting a fluidized bed preparation method, and drying to obtain the dry powder.
Example 5
Example 5 provides a rare monomer ginsenoside composition, which is embodied in the same manner as in example 1.
The present invention also provides a rare ginsenoside capsule prepared from the rare monomer ginsenoside composition, wherein the preparation raw materials comprise 70 parts by weight of the rare monomer ginsenoside composition and 350 parts by weight of hydroxypropyl- β -cyclodextrin.
The preparation method of the capsule comprises the following steps of mixing the rare monomer ginsenoside composition and hydroxypropyl- β -cyclodextrin, adding deionized water, adjusting to obtain slurry with the solid content of 10 wt%, spray-drying the obtained slurry to obtain powder, adding starch according to 40% of the total mass of the obtained composition powder at the air inlet temperature of 170 ℃ and the air outlet temperature of 90 ℃ to obtain the composition powder, preparing the powder by adopting a fluidized bed preparation method, drying, and filling the powder into empty capsules to obtain the capsule.
Example 6
Example 6 provides a rare monomer ginsenoside composition, which is embodied in the same manner as in example 1.
The present invention also provides a rare ginsenoside drop pill prepared from the rare monomer ginsenoside composition, wherein the raw materials for preparing the drop pill comprise 70 parts by weight of the rare monomer ginsenoside composition, 350 parts by weight of hydroxypropyl- β -cyclodextrin and 100 parts by weight of PEG 6000.
The preparation method of the dripping pill comprises the following steps of mixing a rare monomer ginsenoside composition, hydroxypropyl- β -cyclodextrin and PEG6000, adding deionized water, adjusting to a slurry with a solid content of 10 wt%, mixing uniformly, condensing into pills in a cooling manner by adopting a dripping method, adding a coolant, cooling for 90 minutes, and carrying out spray drying at an air inlet temperature of 170 ℃ and an air outlet temperature of 90 ℃, thus obtaining the dripping pill.
Example 7
Example 7 provides a rare monomeric ginsenoside composition, which is embodied in the same manner as in example 1.
The present invention also provides a tablet of rare ginsenoside prepared from the rare monomer ginsenoside composition, which is prepared from the rare monomer ginsenoside composition 70 parts by weight and hydroxypropyl- β -cyclodextrin 350 parts by weight.
The preparation method of the tablet comprises the following steps of mixing a rare monomer ginsenoside composition and hydroxypropyl- β -cyclodextrin, adding deionized water, adjusting to obtain slurry with the solid content of 10 wt%, spray-drying the obtained slurry to obtain powder, adding starch according to 25% of the total mass of the obtained composition powder at the air inlet temperature of 170 ℃ and the air outlet temperature of 90 ℃ to obtain the composition powder, preparing granules by adopting a fluidized bed granulation method, drying, tabletting and coating to obtain the tablet.
Example 8
Example 8 provides a rare monomer ginsenoside composition, which is rare ginsenoside Rg 3. The extraction method of the rare ginsenoside Rg3 is the same as that of example 1.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 9
Example 9 provides a rare monomer ginsenoside composition comprising, in parts by weight, 30 parts rare ginsenoside Rg3, 20 parts rare ginsenoside appd(s). The extraction method of the rare ginsenoside Rg3 is the same as that of example 1. The rare ginsenoside aPPD (S) is purchased from Nanjing spring and autumn bioengineering Co.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 10
Example 10 provides a rare monomeric ginsenoside composition comprising, in parts by weight, 30 parts rare ginsenoside Rg3, 20 parts rare ginsenoside appd(s), 5 parts rare ginsenoside Rh 2. The extraction method of the rare ginsenoside Rg3 is the same as that of example 1. The rare ginsenoside Rh2 and rare ginsenoside aPPD (S) are purchased from Nanjing spring and autumn bioengineering Co.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 11
Example 11 provides a rare monomeric ginsenoside composition comprising, in parts by weight, 30 parts rare ginsenoside Rg3, 20 parts rare ginsenoside ppd, 5 parts rare ginsenoside Rh2, 5 parts rare ginsenoside Rk 2. The extraction method of the rare ginsenoside Rg3 is the same as that of example 1. The rare ginsenoside Rh2, the rare ginsenoside Rk2 and the rare ginsenoside aPPD are purchased from Nanjing spring and autumn bioengineering Co.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 12
Example 12 provides a rare monomeric ginsenoside composition comprising, in parts by weight, 30 parts rare ginsenoside Rg3, 20 parts rare ginsenoside appd(s), 5 parts rare ginsenoside Rh2, 5 parts rare ginsenoside Rk1, 5 parts rare ginsenoside Rk 2. The extraction method of the rare ginsenoside Rg3 is the same as that of example 1. The rare ginsenoside Rh2, rare ginsenoside Rk1, rare ginsenoside Rk2 and rare ginsenoside aPPD (S) are purchased from Nanjing spring and autumn bioengineering Co.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 13
Example 13 provides a rare monomeric ginsenoside composition comprising, in parts by weight, 30 parts rare ginsenoside Rg3, 10 parts rare ginsenoside Rg5, 20 parts rare ginsenoside appd(s), 5 parts rare ginsenoside Rh2, 5 parts rare ginsenoside Rk1, 5 parts rare ginsenoside Rk 2. The extraction method of the rare ginsenoside Rg3 is the same as that of example 1. The rare ginsenoside Rg5, rare ginsenoside Rh2, rare ginsenoside Rk1, rare ginsenoside Rk2, and rare ginsenoside aPPD (S) were purchased from Nanjing spring and autumn bioengineering Co.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 14
Example 14 provides a rare monomeric ginsenoside composition comprising, in parts by weight, 30 parts rare ginsenoside Rg3, 10 parts rare ginsenoside Rg5, 5 parts rare ginsenoside Rh2, 5 parts rare ginsenoside Rk1, 5 parts rare ginsenoside Rk2, 20 parts rare ginsenoside ppd(s), 10 parts rare ginsenoside alppt. The extraction method of the rare ginsenoside Rg3 is the same as that of example 1. The rare ginsenoside Rg5, Rh2, Rh3, Rk1, Rk2, aPPD (S), and aPPT are purchased from Nanjing Chunqiu bioengineering Co., Ltd.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 15
Example 15 provides a rare monomeric ginsenoside composition, which is specifically implemented in a manner similar to example 1, except that the pH of step two of the extraction process of rare ginsenoside Rg3 is replaced by 5 instead of 6.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 16
Example 16 provides a rare monomeric ginsenoside composition, which is specifically implemented in a manner similar to example 1, except that the pH of step two of the extraction process of rare ginsenoside Rg3 is replaced by 7 from 6.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 17
Example 17 provides a rare monomeric ginsenoside composition, which is implemented in a similar manner as example 1, except that the biological enzyme in step two of the extraction process of rare ginsenoside Rg3 is papain.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 18
Example 18 provides a rare monomeric ginsenoside composition, which is implemented in a similar manner as in example 1, except that the biological enzymes in the second step of the extraction method of rare ginsenoside Rg3 are cellulase and papain, and the weight ratio of the two enzymes is 2.2: 1.
this example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 19
Example 19 provides a rare monomeric ginsenoside composition, which is implemented in a similar manner as example 1, except that the biological enzyme in step two of the extraction process of rare ginsenoside Rg3 is cellulase.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 20
Example 20 provides a rare monomeric ginsenoside composition, which is implemented in a similar manner as in example 1, except that vitamin C is absent in step two of the extraction process of the rare ginsenoside Rg 3.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 21
Example 21 provides a rare monomeric ginsenoside composition, which is implemented in a similar manner as in example 1, except that the weight ratio of bio-enzyme in step two and vitamin C in the extraction method of rare ginsenoside Rg3 is 1: 1.
this example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 22
Example 22 provides a rare monomer ginsenoside composition, which is similar to example 1, except that in the third step of the extraction method of the rare ginsenoside Rg3, the concentrated solution obtained in the second step is adsorbed by using a silica gel chromatographic column at a flow rate of 30m L/min, impurities are washed away by deionized water and 20 wt% of ethanol respectively, then the eluted solution is eluted by 80 wt% of ethanol, and the eluted solution is subjected to vacuum concentration and drying at 25 ℃ to obtain ginsenoside Rg3, wherein the volume ratio of the 80 wt% of ethanol to the 20 wt% of ethanol to the deionized water is 1: 0.75: 1.25.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and the raw materials and preparation method are the same as those in example 1.
Example 23
Example 23 provides a rare monomeric ginsenoside composition as in example 1.
This example also provides granules of rare ginsenosides prepared from the above rare monomer ginsenoside composition, and its specific embodiment is similar to example 1, except that hydroxypropyl- β -cyclodextrin is replaced with starch (CAS No. 9005-25-8).
Example 24
Example 24 provides a rare monomeric ginsenoside composition as in example 1.
This example also provides granules of rare ginsenosides prepared from the above rare monomeric ginsenoside composition, and the specific embodiment thereof is similar to example 1, except that hydroxypropyl- β -cyclodextrin was replaced with α -cyclodextrin (CAS No. 10016-20-3).
Example 25
Example 25 provides a rare monomeric ginsenoside composition as in example 1.
This example also provides granules of rare ginsenosides prepared from the above rare monomeric ginsenoside composition, and the specific embodiment thereof is similar to example 1, except that hydroxypropyl- β -cyclodextrin is replaced with γ -cyclodextrin (CAS No. 10016-20-3).
Example 26
Example 26 provides a rare monomeric ginsenoside composition as in example 1.
This example also provides a granule of rare ginsenosides prepared from the above rare monomer ginsenoside composition, which is prepared in a similar manner to example 1, except that hydroxypropyl- β -cyclodextrin is not present in the raw materials.
Example 27
Example 27 provides a rare monomeric ginsenoside composition as in example 1.
This example also provides a granule of rare ginsenoside prepared from the above rare monomer ginsenoside composition, which is prepared in a similar manner to example 1, except that the raw material for preparing the granule contains hydroxypropyl- β -cyclodextrin in an amount of 250 parts by weight.
Example 28
Example 28 provides a rare monomeric ginsenoside composition as in example 1.
This example also provides a granule of rare ginsenoside prepared from the above rare monomer ginsenoside composition, which is prepared in a similar manner to example 1, except that the raw material for preparing the granule contains 450 parts by weight of hydroxypropyl- β -cyclodextrin.
Evaluation of Performance
1. And (3) testing the efficacy:
1) and (3) immune function test: the experimental animal selects a medical experimental-grade nude mouse, tumor cell strains are injected subcutaneously into the nude mouse, after tumors are formed, solutions obtained by dissolving the rare monomer ginsenoside composition granules prepared in the example 1 in distilled water are respectively infused into the nude mouse by a low-dose group, a medium-dose group and a high-dose group, and the low, medium and high doses are respectively 250mg/kg of the low-dose group, 500mg/kg of the medium-dose group and 1500mg/kg of the high-dose group by calculating according to 5 times, 10 times and 30 times (the human recommended amount is 2-4g/d) of the low, medium and high dose groups, and the doses are converted doses for the intragastric infusion.
The nude mice are PBS negative and post-inoculation CTX positive control groups, and are subjected to abdominal gavage by a low-dose group (2.5mg/10g of body weight), medium-dose group (5mg/10g of body weight) and high-dose group (15mg/10g of body weight), all tumor-bearing nude mice are subjected to abdominal gavage for 2 times every day for 20 consecutive days, the mice are killed by removing necks on the 2 nd day after drug withdrawal, tumor masses are cut off and weighed, and the tumor inhibition rate is calculated, wherein the tumor inhibition rate (%) (the average tumor weight of the control group-the average tumor weight of the administration group)/the average tumor weight of the control group is × 100%.
According to the method in the technical specifications of health food inspection and evaluation and the experimental technology of immunotoxicology of the literature, the immune function of a nude mouse is measured, after a ConA-induced nude mouse spleen lymphocyte transformation test, a nude mouse serum hemolysin (hemagglutination), antibody-producing cell detection, a nude mouse abdominal cavity macrophage phagocytic chicken erythrocyte test (in-vivo method), a mononuclear macrophage phagocytic function measurement and an NK cell activity measurement (L DH measurement) are carried out, and then the gastric perfusion rare monomer ginsenoside composition is used for influencing the proliferation capacity of the ConA-induced nude mouse lymphocytes, the rare monomer ginsenoside composition in a low-dose group, a medium-dose group and a high-dose group can improve the proliferation capacity of the ConA-induced nude mouse lymphocytes, and the low-dose group, the medium-dose group and the high-dose group have significance (P <0.01), which shows that the rare monomer ginsenoside composition has the effect of stimulating the spleen lymphocytes to proliferate.
The difference in the number of antibody-producing cells (number of plaques) was significant (p <0.01) both in the intragastric dose and high dose groups, with the number of hemolytic plaques being 109 of splenocytes. It is shown that the rare monomer ginsenoside composition has the function of promoting proliferation of antibody-producing cells.
2) The result of the serum hemolysin determination shows that: the serum hemolysin antibody volume number of the nude mice of the medium-dose group and the high-dose group is higher than that of the original antibody volume number, and the difference is significant (P < 0.01). The rare monomer ginsenoside composition has the function of improving the serum lectin level of the nude mice, and the humoral immunity function is improved by promoting the generation of antibodies in the nude mice.
3) And (3) tumor inhibition rate: analysis was performed using SPSS software and statistics are expressed as "X. + -. s".
① the effect of rare monomer ginsenoside composition on tumor weight and tumor inhibition rate of nude mice with spleen tumor.
TABLE 1 Effect of rare monomeric ginsenoside compositions on tumor weight and tumor inhibition rate of splenic tumor nude mice
Dosage (mg/kg) | Initial body weight (g) | Final body weight (g) | Tumor weight (g) | Tumor inhibition Rate (%) |
Is not used | 19.20(±0.45) | 21.05(±0.62) | 0.88(±0.05) | 0.00 |
250 | 18.63(±0.37) | 20.35(±0.54) | 0.79 (soil 0.03) | 10.22%* |
500 | 19.28(±0.52) | 21.42(±0.52) | 0.65(±0.02) | 26.13%*# |
1500 | 19.13(±0.47) | 20.62(±0.54) | 0.51(±0.03) | 42.04%*# |
Note: p <0.01 compared to negative controls and P <0.05 compared to CTX positive controls.
② the effect of rare monomer ginsenoside composition on tumor weight and tumor inhibition rate of lung cancer mice.
The test method comprises the following steps: a medical experimental-grade nude mouse is selected, lung cancer tumor strains are injected subcutaneously into the nude mouse, and the rare monomer ginsenoside composition granules prepared in the example 1 are filled into stomach to obtain a solution dissolved in distilled water.
The modeling method comprises the steps of taking L ewis lung cancer cell strains in a logarithmic growth phase, filtering the cell strains by a 200-mesh filter screen to prepare single-cell suspensions, diluting the suspensions into 8 × 108/m L cell suspensions by using normal saline, inoculating the cell suspensions to the armpits of the right forelimb of nude mice by using a 0.1m L conventional method, performing abdominal gavage (2.5mg/10g of body weight) on the nude mice in a low-dose group, performing abdominal gavage (5mg/10g of body weight) on a medium-dose group, performing abdominal gavage (15mg/10g of body weight) on a high-dose group, performing abdominal gavage 2 times every day for all the nude mice with lung cancer for 20 consecutive days, removing necks and killing the mice on a 2 days after drug withdrawal, sectioning and weighing tumor masses, and calculating the tumor inhibition rate, wherein the tumor inhibition rate (%) is (average tumor weight of a control group-average tumor weight of an administration group)/average tumor weight of a control group of × 100.
TABLE 2 Effect of rare monomer ginsenoside compositions on tumor weight and tumor inhibition rate of splenic tumor nude mice
Dosage (mg/kg) | Initial body weight (g) | Final body weight (g) | Tumor weight (g) | Tumor inhibition Rate (%) |
Is not used | 19.70(±0.45) | 21.65(±0.52) | 1.16(±0.03) | 0.00 |
250 | 19.88(±0.38) | 20.76(±0.44) | 0.94(±0.03) | 18.96%* |
500 | 19.67(±0.52) | 21.04(±0.53) | 0.73(±0.02) | 37.06%*# |
1500 | 19.15(±0.47) | 20.56(±0.54) | 0.54(±0.03) | 53.44%*# |
Note: p <0.01 compared to negative controls and P <0.05 compared to CTX positive controls.
As can be seen from tables 1 and 2, the tumor inhibition effect (P <0.01) was significant in both the high dose group and the low dose group compared to the experimental nude mice without gavage rare monomer ginsenoside composition, wherein the tumor inhibition rate in the high dose group was over 85%. It is shown from the process of gastric lavage of nude mice that the survival status and activity of the nude mice of the high-dose group and the low-dose group are obviously better than those of the CTX control group, which also shows that the rare monomer ginsenoside composition is helpful to improve the immunity of the nude mice.
4) The effect on the phagocytic capacity of macrophages. The effect of the rare monomer ginsenoside composition on phagocytosis of chicken red blood cells by abdominal macrophages of nude mice is tested.
According to test results, the phagocytic rate and the phagocytic index of abdominal macrophages of medium and high dose groups are remarkably increased compared with those of blank groups (P < 0.05), which shows that the rare monomer ginsenoside composition improves the phagocytic capacity of abdominal macrophages of mice, and the increase of each dose group of carbon clearance phagocytic index is not very remarkable.
The comprehensive efficacy test result shows that: the rare monomer ginsenoside composition disclosed by the invention plays a role in immune monitoring, and macrophages in immune cells can directly phagocytose variant cells; has obvious difference on killing tumor cell biomembrane by NK cell, inactivating tumor cell and playing cell immunity function. And the phagocytosis rate and the phagocytosis index of abdominal cavity macrophages of medium and high dose groups are found to be remarkably different from those of blank groups (P <0.01), which indicates that the rare monomer ginsenoside composition improves the phagocytosis capacity of abdominal cavity macrophages of mice. Meanwhile, the NK cell activity is increased along with the increase of the dosage of the rare monomer ginsenoside composition, wherein the NK cell activity of medium and high dose groups is increased remarkably (P < 0.01). The rare monomer ginsenoside composition can improve the immunocompetence of mice. Through comprehensive analysis of the test results of the immune function test, the immunity of the mice in medium and high dose groups is obviously improved, which shows that the rare monomer ginsenoside composition has the function of obviously improving the immunity.
2. And (3) purity testing: the purity of the rare ginsenoside Rg3 contained in the rare ginsenoside Rg3 obtained in examples 1 to 3 and 15 to 22 was measured by high performance liquid chromatography, and the results are shown in Table 3.
TABLE 3 purity test results
Examples | Purity test/%) |
Example 1 | 97.1 |
Example 2 | 96.9 |
Example 3 | 97.1 |
Example 15 | 82.3 |
Example 16 | 66.7 |
Example 17 | 71.0 |
Example 18 | 65.8 |
Example 19 | 59.2 |
Example 20 | 54.6 |
Example 21 | 86.3 |
Example 22 | 60.1 |
3. And (3) stability testing: the rare ginsenoside preparations obtained in examples 1 to 4, 6 to 14 and 23 to 28 were spread on the bottom of a culture dish (until the whole culture dish was just full of the sample), the culture dish containing the sample was placed in a ventilated, cool and dry place, and 10 volunteers were randomly selected to evaluate the shape of the product after 7 days and 30 days, respectively. The evaluation standard is that if the product has no serious deformation, cracking, chalking or abnormal color, the product is marked as 2 points; if the product has slight deformation, cracking, chalking or abnormal color, the score is 1; if the product is severely deformed, cracked, chalked or abnormal in color, the average score is scored as 0 and is shown in Table 4.
Table 4 stability test results
The combination of the above experimental results shows that: animal experiment research shows that the rare monomer ginsenoside composition has the functions of obviously improving the immunity and inhibiting tumors; purity tests show that the purity of the obtained rare ginsenoside Rg3 can reach 96.9-97.1 by the extraction method of the rare ginsenoside Rg3 without inert gas protection or heating conditions; stability tests show that the preparation product prepared by the invention is placed for 7 days or even 30 days, has no serious deformation, cracking, powdering or abnormal color and has good stability.
The foregoing examples are merely illustrative and serve to explain some of the features of the method of the present invention. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. The invention is not limited to the embodiments described above, but rather, many modifications and variations may be made by one skilled in the art without departing from the scope of the invention.
Claims (10)
1. A rare monomer ginsenoside composition is characterized by comprising one or more of rare ginsenoside Rg3, rare ginsenoside Rg5, rare ginsenoside Rh2, rare ginsenoside Rh3, rare ginsenoside Rk1, rare ginsenoside Rk2, rare ginsenoside aPPD and rare ginsenoside aPPT.
2. The rare monomer ginsenoside composition of claim 1, wherein the composition comprises, by weight, 0.5 to 30 parts of rare ginsenoside Rg3, 1 to 10 parts of rare ginsenoside Rg5, 0.5 to 5 parts of rare ginsenoside Rh2, 1 to 10 parts of rare ginsenoside Rh3, 1 to 5 parts of rare ginsenoside Rk1, 1 to 10 parts of rare ginsenoside Rk2, 1 to 20 parts of rare ginsenoside aPPD, and 1 to 10 parts of rare ginsenoside aPPT.
3. The rare monomeric ginsenoside composition of claim 1 or claim 2, wherein the extraction method of the rare ginsenoside Rg3 comprises the following steps:
the method comprises the following steps: according to the weight parts, 1-10 parts of ginseng is crushed, 1-10 parts of solvent type degreasing agent is added, the mixture is degreased and filtered, filter residue is collected, 5-40 parts of water is added, and the mixture is uniformly mixed to obtain a mixed water solution;
step two: adding a pH regulator into the mixed aqueous solution obtained in the step one to regulate the pH to 5.5-6.5, adding biological enzyme, continuously adding 3-30 parts of water, uniformly mixing, adding a polyhydroxy compound, stirring and reacting at 20-30 ℃ for 5-10 h, performing centrifugal separation, and concentrating the solution obtained by separation to half of the original volume under the conditions of vacuum degree of 0.05-0.07 Mpa and temperature of 20-40 ℃ to obtain a concentrated solution;
and step three, adsorbing the concentrated solution obtained in the step two by using a polystyrene resin chromatographic column at the flow rate of 20-40 m L/min, washing impurities by using deionized water and (10-30) wt% of ethanol respectively, eluting by using (70-90) wt% of ethanol, and performing vacuum concentration and drying on the obtained eluent at the temperature of 20-30 ℃ to obtain ginsenoside Rg 3.
4. A rare monomer ginsenoside composition of claim 3, wherein the pH regulator in step two is selected from the group consisting of acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, oxalic acid, citric acid, malic acid, monofluoroacetic acid, difluoroacetic acid, trifluoroacetic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid.
5. The rare monomeric ginsenoside composition of claim 3, wherein the biological enzyme in step two is selected from the group consisting of cellulase, hemicellulase, proteolytic enzyme, pectinase, and lactase.
6. The rare monomeric ginsenoside composition of claim 3, wherein the polyhydroxy compound in step two is selected from the group consisting of vitamin C, vitamin C glycoside, vitamin C phosphate, sodium vitamin C phosphate, and magnesium vitamin C phosphate.
7. A rare ginsenoside preparation prepared from the rare monomer ginsenoside composition of any one of claims 1-6, wherein the preparation raw materials comprise 60-80 parts by weight of the rare monomer ginsenoside composition and 300-400 parts by weight of polysaccharide.
8. The rare ginsenoside preparation prepared from the rare monomer ginsenoside composition of claim 7, wherein the polysaccharide is a polysaccharide containing 2-10 glycosidic linkages.
9. The rare ginsenoside preparation prepared from the rare monomer ginsenoside composition of claim 7 or 8, wherein the raw materials for the preparation further comprise adjuvants.
10. An application of the rare ginsenoside preparation prepared from the rare monomer ginsenoside composition according to any one of claims 7-9, wherein the rare ginsenoside preparation is applied to capsules, tablets, soft capsules, liquid, granules, dry powder, oral liquid, pills, paste and gels.
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CN112294830A (en) * | 2020-09-29 | 2021-02-02 | 吉林瑞诺科技有限公司 | American ginseng leaf product rich in rare ginsenoside |
CN116077679A (en) * | 2023-04-11 | 2023-05-09 | 中国农业科学院特产研究所 | Ginsenoside RK1 cyclodextrin inclusion compound and preparation and sleep improvement application thereof |
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