KR101897811B1 - Manufacturing method for mass-production of ginsenoside Rh1-S, Rh1-R, Rg4 and Rg6 - Google Patents

Abstract

The present invention relates to a method for producing at least one specific ginsenoside selected from the group consisting of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 by mixing distilled water into ginsenoside Re, . Since the specific ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 exist in a small amount in the ginseng extract, the amount of the purified ginsenosides is so small that it is difficult to use them. However, Rin, Rh1-R, Rg4 and Rg6 are produced using only the detachable ginsenoside Re, so that the ginsenosides Rc, Rd , Rf and the like can be prevented and purification of the specific ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 is easy, and mass production is very easy. In addition, when the ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 are produced through the acid treatment, the separation resin is contaminated during the separation and purification and the long-term use is difficult. Since the ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 can be mass-produced by mixing distilled water with ginsenoside Re and treating the mixture at high temperature and high pressure, contamination problems that may occur during the separation process can be solved, Is easy to manufacture.

Description

Rh1-R, Rg4 and Rg6 of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6,

The present invention relates to a method for producing at least one ginsenoside selected from the group consisting of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 from ginsenoside Re.

Ginseng ( Panax ginseng ) is a perennial plant belonging to the genus Ginseng ( Araliaceae ). It has been traditionally used in the prevention and treatment of various diseases in Korea and China. It has excellent therapeutic effect and has no side effect It is known.

Ginseng saponin, which is the main effect of ginseng, is known as ginsenoside and is known to have a unique chemical structure and pharmacological effect unlike saponin found in other plants.

Ginsenoside is a neutral glycoside conjugated with glucose, arabinose, xylose, rhamnose, and the like on a triterpenoid-based dammarane skeleton. At present, more than 30 chemical structures have been identified. Depending on the nature of the chemical structure, protopanaxadiol (PPD) (19 species), protopanaxatriol (PPT) (10 species) Oleanane system (one species).

The major ginsenosides present in fresh ginseng and white ginseng are Rg1, Re, Rf, Rh1, Rb1, Rb2, Rc, and Rd, accounting for 80-90% or more of the total ginsenosides. On the other hand, in the case of the specific ginsenosides, a part of the sugar is separated from the ginsenosides present in a large amount, or a dehydration reaction occurs, and ginseng is present in a small amount in water and alcohol-extracted extracts.

The pharmacological activity by the ginsenoside is indicated by the specific ginsenoside originating from the above-mentioned ginsenosides present in large quantities, and it is considered that the pharmacological activity by the ginsenoside is enhanced by the immunosuppressive effect, anti-inflammatory, antiallergic, anticancer, hypotensive, anti-cholesterol, (Kim, YS et al., Arch Pharm Res., 2000; Tachikawa, E. et al., Biochem Pharmacol., 2003; Tsai, SC et al , Chin J Physiol., 2003, Shibata, S., J Korean Med Sci., 2001). In addition, in the case of specific ginsenosides, unlike ginsenosides present in large quantities, the intestinal absorption rate is excellent and is suitable for use as a pharmaceutical composition for various diseases. Therefore, there is a need for research on a method for mass-producing a specific ginsenoside having excellent pharmacological activity and easy absorption.

Regarding the method for producing ginsenoside Rh1-S, Rh1-R, Rg4 or Rg6, Korean Patent Registration No. 10-0564383 discloses a method for producing ginsenosides Re1 and Rg1 using citric acid as F4 (Rg4), Rg6, Rh4. Korean Patent No. 10-1625474 discloses a method for mass-producing ginsenoside Rh4 by mixing an organic acid with ginsenoside Re and then subjecting it to high temperature and high pressure treatment. No. 10-2012-0134166 discloses a method for producing ginseng extract containing micro ginsenoside at a high concentration using lactic acid bacteria. However, when ginsenoside Re is mixed with distilled water and subjected to high temperature and high pressure treatment, Rh1-S, Rh1 -R, Rg4 and Rg6 have not been disclosed.

Korean Patent No. 10-0564383 (Method for producing ginsenoside derivative, registered on March 20, 2006) Korean Patent No. 10-1625474 (Mass Production Method of Ginsenosides Al HQ 4, registered on May 24, 2016) Korean Patent Laid-Open No. 10-2012-0134166 (Method for producing ginseng extract containing trace amount of ginsenosides, December 12, 2012)

Kim, YS et al., Differential expression of protein kinase C subtypes during ginsenoside Rh2-Induced apoptosis in SK-N-BE (2) and C6Bu-1 cells, Arch Pharm Res., 23 (5), 518-524, 2000 . Shibata, S., Chemistry and cancer prevention activities of ginseng saponins and some related triterpenoid compounds, J Korean Med Sci., 16 (suppl), S28-37, 2001. Tachikawa, E. et al., In vitro inhibition of adrenal catecholamine secretion by steroidal metabolites of ginseng saponins, Biochem Pharmacol., 66 (11), 2213-2221, 2003. Tsai, S. C. et al., Stimulation of the secretion of luteinizing hormone by ginsenoside-Rb1 in male rats, Chin J Physiol., 46 (1), 1-7, 2003.

It is an object of the present invention to provide a method for producing at least one ginsenoside selected from the group consisting of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 from ginsenoside Re.

The present invention relates to a process for producing at least one ginsenoside selected from the group consisting of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 from ginsenoside Re,

(Step 1) Separation of ginsenoside Re from ginseng;

(2 steps) Mixing 250 to 350 parts by weight of distilled water with 100 parts by weight of ginsenoside Re produced in step 1;

(3 step) a step of subjecting ginsenoside Re mixed with distilled water to a high-temperature high-pressure treatment; And

(4 steps), the ginsenoside foodstuffs subjected to high-temperature and high-pressure treatment are subjected to chromatography to separate and prepare at least one ginsenoside selected from the group consisting of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 step; .

Also, ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 are produced from ginsenoside Re through the process of Reaction Scheme 1 below.

[Reaction Scheme 1]

The ginsenoside Re in the above one step is obtained from ginseng extract. The ginseng extract can be prepared by using all of the ginseng-derived roots, fruits, leaves, stems and the like derived from ginseng, A large amount of ginsenoside Re can be obtained.

Ginseng used in the extraction of the ginsenoside Re is a perennial plant belonging to the genus Panax (Panax), ginseng (Panax ginseng), hwagisam (Panax quinquefolia), jeonchilsam (thirty-seven, Panax notoginseng), jukjeol three (Panax japonicus), Panaxa pseudoginseng . And one species selected from Panax vietnamensis , Panax elegatior , Panax wangianus and Panax bipinratifidus , Panax angustifolium , It is most preferable to use Korean ginseng, which is known to have a high saponin content, but the type of ginseng is not particularly limited thereto.

The ginseng extract may be extracted by using ginseng as a solvent, water, a C1 to C4 alcohol, or a mixture thereof. The C1 to C4 alcohols may be selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol and isobutanol ≪ / RTI > The water, the C1 to C4 alcohol, or the mixed solution thereof used in the preparation of the ginseng extract may be used in an amount of 1 to 40 times the volume of the ginseng used (1 to 40 L based on 1 kg of ginseng) 40 times, and the process can be repeated from 1 to 4 times.

In order to extract ginsenoside Re from the ginseng extract, ginseng water, C1-C4 alcohol, or a mixed solution thereof is dissolved in water and extracted with n-hexane, methylene chloride, acetone, chloroform, Ethyl acetate, diethyl ether, water-saturated butanol, and n-butanol, or sequentially fractionated by combining these solvents and then purified using column chromatography . The extraction time of the extract or the fraction thereof is not particularly limited, but it is preferably extracted within 10 minutes to 1 day. As the extraction apparatus, a conventional extraction apparatus, an ultrasonic pulverization extractor, or a fractionator may be used.

On the other hand, the ginseng extract may be isolated or isolated by known methods used for the separation and extraction of plant components, such as extraction with an organic solvent (alcohol, ether, acetone, etc.), distribution with hexane and water, Ginsenoside Re can be obtained by fractionation or purification using a suitable combination method. The chromatography can be carried out using silica gel column chromatography, LH-20 column chromatography, ion exchange resin chromatography, medium pressure liquid chromatography chromatography, thin layer chromatography (TLC), silica gel vacuum liquid chromatography, and high performance liquid chromatography.

In the above two steps, 250 to 350 parts by weight of distilled water is mixed with 100 parts by weight of ginsenoside Re. When the amount of distilled water mixed in 100 parts by weight of ginsenoside Re exceeds 250 parts by weight or exceeds 350 parts by weight, The amount of ginsenoside Re remaining unconverted to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6, which are the specific ginsenosides to be produced in large quantities in the present invention, is large, and production cost is lost.

The high-temperature and high-pressure treatment in the above three steps is carried out at a temperature range of 110 to 140 ° C and a pressure of 0.11 to 0.16 MPa for 7 to 9 hours. When the high temperature and high pressure treatment time is less than 7 hours or the pressure is 0.11 , Rh1-R, Rg4 and Rg6 are produced under the condition that the temperature is less than 110 占 폚 or less than 100 占 폚, or the temperature is lower than 110 占 폚, due to the remaining ginsenoside Re not converted to the specific ginsenoside, The yield of obtaining Rh1-S, Rh1-R, Rg4 and Rg6 is remarkably lowered, which is not economical. Further, when the high-temperature and high-pressure treatment time exceeds 12 hours or the pressure exceeds 0.16 MPa or the temperature exceeds 140 ° C, the ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 are increased The increase in the effect to be caused is not large and can be rather reduced, leading to a loss of manufacturing cost, which is not preferable.

It is preferable to use reversed-phase column chromatography (C18) or HPLC for the chromatography in the above-mentioned 4 steps, and the purified ginsenoside by this chromatography preferably has a purity of 90% or more, more preferably 90 to 99 %, And most preferably 95 to 99%.

The present invention relates to a method for producing at least one specific ginsenoside selected from the group consisting of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 by mixing distilled water into ginsenoside Re, . Since the specific ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 exist in a small amount in the ginseng extract, the amount of the purified ginsenosides is so small that it is difficult to use them. However, Rin, Rh1-R, Rg4 and Rg6 are produced using only the detachable ginsenoside Re, so that the ginsenosides Rc, Rd , Rf and the like can be prevented and purification of the specific ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 is easy, and mass production is very easy. In addition, when the ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 are produced through the acid treatment, the separation resin is contaminated during the separation and purification and the long-term use is difficult. Since the ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 can be mass-produced by mixing distilled water with ginsenoside Re and treating the mixture at high temperature and high pressure, contamination problems that may occur during the separation process can be solved, Is easy to manufacture.

Fig. 1 shows the HPLC results of the conversion of ginsenosides Re to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 when subjected to high temperature and high pressure under the conditions of Example 1.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the present invention is not limited to the embodiments described herein but may be embodied in other forms. Rather, the intention is to provide an exhaustive, complete, and complete disclosure of the principles of the invention to those skilled in the art.

<Example 1> Preparation of Rh1-S, Rh1-R, Rg4 and Rg6 from ginsenoside Re>

10 kg of a 70% (v / v) aqueous methanol solution was added to 1 kg of dried ginseng leaves collected from Geumsan in September, 2013, and leached for one day, followed by ultrasonic shaking for 3 hours and filtration. After filtration, the remaining ginseng leaves were added with 8 liters of 70% (v / v) methanol, and then the leaching and ultrasonic shaking were repeated two more times. The filtrates obtained in the above procedure were combined and concentrated under reduced pressure to obtain 416 g &Lt; / RTI &gt; Then, the methanol extract was completely dissolved in 3 L of water by shaking ultrasonically, and then 2 L of diethyl ether was added thereto, followed by stirring at room temperature for 2 days. After the stirring, the solution was transferred to a separatory funnel to remove the diethyl ether layer, and 5 liters of water saturated butanol was added to the remaining water layer, followed by stirring in a stirrer for 2 days. The stirred solution was transferred to a separatory funnel and separated for more than one day. Only the butanol layer was collected and concentrated under reduced pressure to obtain 157 g of completely dried butanol extract. Thereafter, 157 g of the butanol fraction was dissolved in methanol, mixed with 500 g of silica gel (250 to 400 mesh), kneaded, and concentrated under reduced pressure to prepare fine powder. In addition, the silica gel is kneaded in chloroform, poured into an open column of 12 × 50 cm, filled up to a height of 25 cm, and then used to separate the sea sand (silica sand and silica gel) ) Was raised by 2 cm, and then the powder was raised. The mixture was mixed with chloroform: methanol: water at a ratio of 10: 2: 0.2 (1500 ml: 300 ml: 30 ml) in a separatory funnel, and the lower layer was taken and separated and purified using silica gel column chromatography as a developing solvent, A column fraction containing a large amount of side Re was obtained, which was concentrated under reduced pressure. The column fraction containing the ginsenoside Re was subjected to C18 reverse phase column chromatography. A C18 reversed phase packing material kneaded with a 40% (v / v) aqueous methanol solution was filled in a 3.5 x 60 cm flash column to a height of 30 cm, (V: v), 3: 1 (v / v) methanol: water in a 1: 1 (v: v) (v: v). Through the above procedure, 11.5 g of pure ginsenoside Re was finally obtained.

10 mg of the ginsenoside Re obtained in the above procedure was taken into a 1.5 ml vial and mixed with 25 μl or 35 μl of distilled water. The resulting mixture was placed in a 125 ml tube, 5 ml of distilled water was added thereto, Lt; / RTI &gt; Then, the mixture was placed in a sterilizer (SANYO autoclave, MLS-3780 model) and steamed at 120 ° C under a pressure of 0.13-0.15 MPa for 8 hours. The resulting water was dried in Centrifan PE. The concentrated powders were firstly separated by C18 reverse phase column chromatography. At this time, the C18 reversed phase filler kneaded with a 40% (v / v) methanol aqueous solution was filled up to a height of 30 cm on a 3.5 × 60 cm flash column, and the water was dissolved in an aqueous 25% (v / v) methanol aqueous solution, Methanol: water was used as a developing solvent, and it was separated and purified at a ratio of 1: 1 (v: v) to 2: 1 (v: v) and 3: 1 (v: v).

The first-purified fractions CFr01 and CFr02 from the C18 reverse phase column chromatography method were subjected to secondary purification by multiple preparative HPLC using YMC's LC-forte / R. The column used was YMC-Dispopack AT ODS-25 (40 g), which was separated and purified by connecting it to three multiples. Water (H ₂ O) and acetonitrile (CH ₃ CN) were used as the solvents used for separation. After sufficiently filling the YMC-Dispopack AT ODS-25 with an aqueous 15% (v / v) acetonitrile solution , And the sample was dissolved in a 35% (v / v) methanol aqueous solution and loaded. (20% B), 25-90 minutes (40% B), 90-90 minutes (40% B) and water (H ₂ O, A solvent) and acetonitrile (CH ₃ CN, B solvent) A concentration gradient of 120 minutes (50% B), 120-135 minutes (65% B), 135-155 minutes (85% B), 155-160 minutes (100% (Gradient elution system) to obtain ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6. Part of the concentrated powder was taken from the concentrate before separation and purification, and the conversion to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 was confirmed by HPLC analysis and shown in Table 2 of Experimental Example 1 below.

<Comparative Example 1> Preparation of Comparative Ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 (1)

Rh1-S, Rh1-R, Rg4 and Rg6 were prepared in the same manner as in Example 1 except that they were matured for 2, 4, 6 or 10 hours instead of 8 hours in a sterilizer, The conversion to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 was confirmed through analysis. The results are shown in Table 2 of Experimental Example 1 as Comparative Examples 1-1 to 1-4.

<Comparative Example 2> Preparation of Comparative Ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 (2)

Rh1-S, Rh1-R, Rg4 and Rg6 were prepared in the same manner as in Example 1 except that they were matured at 100 DEG C or 150 DEG C for 8 hours instead of being steamed at 120 DEG C for 8 hours in a sterilizer, HPLC analysis confirmed conversion of ginsenoside Re to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6, and was shown in Table 2 of Experimental Example 1 as Comparative Examples 2-1 and 2-2.

< Comparative Example  3. Compared to Gencenoside Rh1 -S, Rh1 -R, Rg4  And Of Rg6  Manufacturing ③>

Rd1-S, Rh1-R, Rg4 and Rg6 were prepared in the same manner as in Example 1 except that 10 mg of ginsenoside Re was taken into 1.5 ml vials and 10, 50 or 100 μl And the conversion of ginsenoside Re to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 was measured by HPLC analysis of the boiled water according to the amount of distilled water mixed for 8 hours in a sterilizer The results are shown in Table 2 of Experimental Example 1 and Comparative Examples 3-1 to 3-3.

&Lt; Comparative Example 4: Preparation of Comparative Ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 &

10 mg of ginsenoside Re obtained in the same manner as in Example 1 was taken in a 5 ml round-bottom flask and dissolved in 10 ml of distilled water. A reflux device and a heating mantle were placed in the sample, and the mixture was heated to reflux at 100 ° C for 30 days. After the reaction was completed, the flask was cooled to room temperature, and distilled water was removed from the reduced pressure concentrator. Part of the dried reaction product was taken out and analyzed by HPLC to determine the ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 .

&Lt; Comparative Example 5: Preparation of Comparative Ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 &

10 mg of ginsenoside Re obtained in the same manner as in Example 1 was taken and placed in a vial of 1.5 ml, and 25 μl of apple vinegar was mixed. The sample was placed in a 125 ml tube and the distilled water 5 Ml was added and the sample was boiled. Thereafter, the mixture was placed in a sterilizer (SANYO autoclave, MLS-3780 model), and the mixture was steamed at 121 DEG C under a pressure of 0.13 to 0.15 MPa for 2 hours. The boiled water was dried in Centrifan PE and the concentrated powder was analyzed by HPLC to confirm the conversion to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6.

EXPERIMENTAL EXAMPLE 1 Confirmation of conversion of ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 [

In order to measure the change of ginsenoside Re, the above-mentioned samples 1 to 2 and Comparative Examples 1 to 5 were dried in a Centrifan PE to remove a small amount of water 1 mg of each sample was taken and dissolved in 1 ml of methanol for HPLC. The filtrate was filtered through a 0.50 μm filter and used for HPLC analysis.

HPLC performance conditions column ACE 5-C ₁₈ (250 x 4.6 mm) Flow rate 1.0 ml / min Detector UV detector, 205nm Solvent A; H ₂ O, B; CH ₃ CN
(35% B), 85- 105 minutes (50% B), 105-135 minutes (65% B), 135-145 minutes (85% B) 145-155 minutes (100% B), 155-160 minutes (100% B), 160-163 minutes (20% B), 163-165 minutes (20% B) Temperature 40 ℃

Condition Ginsenoside (占 퐂 / mg) Re Rh1-S Rh1-R Rg4 Rg6 Rh4 total Example 1 25 [mu] L, 120 [deg.] C for 8 hours, 7.0 153.0 121.0 228.0 202.0 4.2 715.2 Example 2 Mu] l, 120 [deg.] C for 8 hours, 4.1 148.0 119.0 212.0 196.5 3.1 682.7 Comparative Example 1-1 25 [mu] L, 120 [deg.] C for 2 hours, 513.9 25.3 19.4 101.7 65.1 0 725.4 Comparative Example 1-2 25 [mu] L, 120 [deg.] C for 4 hours, 305.6 64.1 61.8 122.9 123.9 3.5 681.8 Comparative Example 1-3 25 [mu] l, 120 [deg.] C for 6 hours, 85.3 122.0 95.3 200.6 147.0 9.2 659.4 Comparative Example 1-4 25 [mu] l, 120 [deg.] C for 10 hours, 0 108.0 98.0 145.0 122.0 53.0 526.0 Comparative Example 2-1 25 쨉 l, at 100 캜 for 8 hours, 202.1 101.2 108.0 158.2 146.2 2.8 718.5 Comparative Example 2-2 25 [mu] L, 150 [deg.] C for 8 hours, 12.1 83.1 76.4 135.2 115.4 132.2 554.4 Comparative Example 3-1 10 [mu] l, 120 [deg.] C for 8 hours, 151.4 101.1 96.8 192.6 151.0 4.3 697.2 Comparative Example 3-2 50 쨉 l, 120 째 C, 8 hours, 97.0 102.0 101.0 193.0 159.0 5.9 657.9 Comparative Example 3-3 100 占 퐇, 120 占 폚 for 8 hours, 87.0 112.4 98.1 194.0 165.0 0.8 657.3 Comparative Example 4 Boiling 30 days 0 62.1 26.4 3.4 20.6 4.1 116.6 Comparative Example 5 After 25 占 퐇 of acid treatment, the mixture was stirred at 120 占 폚 for 2 hours, 0 20.5 23.1 60.5 33.1 274.5 411.7

Referring to Table 2 and FIG. 1, when distilled water was mixed with ginsenoside Re as in the present invention and then subjected to high-temperature and high-pressure treatment, most of the ginsenoside Re was hydrolyzed almost without any remaining ginsenoside Re, -S, Rh1-R, Rg4 and Rg6.

However, unlike the present invention, Comparative Examples 1-1 to 1-4 in which the time for high-temperature and high-pressure treatment is out of 7 to 9 hours and Comparative Examples 1-1 to 1-4 in which the temperature is out of 110 to 140 ° C in the high- 1 to 2-2 and Comparative Examples 3-1 to 3-3 in which the amount of distilled water added to 10 mg of ginsenoside Re deviates from 20 to 40 쨉 l, It was confirmed that the conversion rates to senosides Rh1-S, Rh1-R, Rg4 and Rg6 were significantly lower than those of the examples of the present invention, which is not economical.

In the case of Comparative Example 4 heated to a high temperature of 100 占 폚 under the condition that no pressure was applied, the temperature was changed very slowly to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6, , And it was confirmed that the ginsenoside Re completely disappeared only after 30 days and that the conversion rate to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6 was as low as about 10% in ginsenoside Re Respectively.

On the other hand, in the case of Comparative Example 5 in which acid was treated instead of distilled water for ginsenoside Re, the target ginsenosides of the present invention, which were not converted to ginsenosides Rh1-S, Rh1-R, Rg4 and Rg6, Rh4. &Lt; / RTI &gt;

Thus, the method of mixing distilled water in ginsenoside Re as described in the present invention and then subjecting it to high-temperature and high-pressure treatment at 110 to 140 ° C for 7 to 9 hours is a method for converting the conversion rate Can be remarkably increased, which is an easy method for mass production.

Claims (3)

(Step 1) Separation of ginsenoside Re from ginseng;
(2 steps) Mixing 250 to 350 parts by weight of distilled water with 100 parts by weight of ginsenoside Re produced in step 1;
Treating the ginsenoside Re mixed with distilled water in the step (3 step) 2 for 7 to 9 hours at a temperature of from 110 to 140 캜 and a pressure of from 0.11 to 0.16 MPa at a high temperature and a high pressure; And
Chromatography of the high-temperature and high-pressure treated ginsenoside product in step (4 step) to separate and prepare at least one ginsenoside selected from ginsenoside Rh1-S or Rh1-R;
Wherein at least one ginsenoside selected from ginsenoside Rh1-S or Rh1-R is produced from ginsenoside Re. delete The method according to claim 1,
The ginsenoside Re of the four steps is subjected to chromatography to obtain at least one ginsenoside selected from ginsenoside Rh1-S or Rh1-R having a purity of 90% or more. From the ginsenoside Re, Rh1-S or Rh1-R. &Lt; / RTI &gt;

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