WO2004054595A1

WO2004054595A1 - A method for preparing low polar ginsenoside and aglucon thereof by catalytic pyrolysis

Info

Publication number: WO2004054595A1
Application number: PCT/CN2003/001055
Authority: WO
Inventors: Ling Yany; Ke-Jiang He; Peng Li; Yi Yang
Original assignee: Dalian Institute Of Chemical Physics
Priority date: 2002-12-13
Filing date: 2003-12-11
Publication date: 2004-07-01
Also published as: CN1269835C; CN1508147A

Abstract

A method for preparing low polar ginsenoside and aglucon thereof by catalytic pyrolysis, characterized in that: raw material ginsenoside was subjected to braize at high temperature of 110-180°C, wherein using acid as catalyst. The present invention definites the catalyst which necessary for high temperature pyrolysis of ginsenoside, solves the mechanism or essential problems associated with high temperature pyrolysis of natural ginsenoside in the processing technology of dried steamed root of Panax ginseng (Araliaceae), provides a handy and high effective method for preparing low polar ginsenoside. Using the method provided by the present invention to prepare low polar ginsenoside, technology is handy, quality is controllable, percent conversion of material aglucon is high, total yield of aglucon as primary product is high, and cost is low; when combining with isolation and purification technology, can prepare monomeric low polar ginsenoside in bulk. The prepared low polar ginsenoside monomer or mixture thereof both can combine with various official medicinal or food excipient and accessory ingredient to prepare various dosage form for medical, cosmetic and functional food use, and can be used as material for synthesize other bioactive compound.

Description

Method for preparing lower ginsenoside and its aglycon by catalytic pyrolysis Technical field:

The present invention relates to the preparation of low-polar ginsenosides from ginsenosides or plants containing ginsenosides (which can be derived from rhizomes and leaves of ginseng, panax notoginseng, American ginseng, and Gynostemma pentaphyllum and their products such as white ginseng, red ginseng or its extracts, etc.) The method, in particular, relates to a method for preparing a ginsenoside derivative by pyrolysis using an acid as a catalyst.

Background technique:

Ginseng has a variety of physiological and pharmacological effects, such as anti-tumor, enhance immunity, improve microcirculation, stabilize blood pressure, regulate blood sugar, lower blood fat, soothe the nerves, anti-aging, anti-stress, regulate digestive function, prevent gastrointestinal ulcer, improve quality of life, Enhance memory and learning ability. In terms of anti-tumor, ginseng has: 1. Regulation of gene expression and differentiation of tumor cells; 2. Inhibition of tumor invasion and metastasis; 3. Inhibition of tumor-induced neovascularization; 4. Reduction of toxic and side effects of chemotherapy drugs; 5. Reverse tumor resistance, increase the sensitivity of chemotherapeutics, and enhance the efficacy of chemotherapy.

The medicinal forms of ginseng are fresh ginseng, white ginseng, and red ginseng. The relationship between the three is that fresh ginseng is often dried at room temperature to obtain white ginseng, and steamed and dried to red ginseng. Use experience and pharmaceutical research show that the efficacy of red ginseng is higher than that of white ginseng and fresh ginseng. Modern research has further proved that the unique medicinal effects of red ginseng benefit from the natural trace or rare ingredients such as the unique Rg ₂ , Rg ₃ , R, Rk and polyacetylene compounds such as ginsynol. Traditionally, the preparation of ginseng is only based on the appearance and texture of red ginseng, not the content of active ingredients. Recently, Japanese Patent Publication (62-158490) reported that the ginsenoside Rh culture content was significantly increased after high temperature treatment at 110 ~ 160 ° C; U.S. Patent (5776460) reported treatment at 120 ~ 180 ° C. After 0.5 to 20 hours, the low-polar saponins in ginseng increased 20 to 40 times. However, neither of the two patents deals with the transformation mechanism of high-temperature pyrolysis. As a result, only the temperature is controlled, and the quality and quantity of ginseng pyrolysis products cannot be constant, that is, the conversion rates of natural ginsenosides in different batches of products are different. The content and proportion of low-polar saponins in products are different. US patent (5776460) shows that most of the triol-type ginsenosides are converted into volatile substances after pyrolysis at high temperature, and the required saponins such as Rg ₂ , F ₄ , Rg ₆ , R Rh ₄ and Rk ₃ cannot be obtained in large quantities.

The research of the present invention shows that malonate, aspartic acid, and glutamic acid in ginseng are natural catalysts for the pyrolysis of ginseng. By quantitatively using the catalyst in the present invention, the reaction can be controlled, targeted and maximized. Preparation of low-polarity ginsenosides and their derivatives has great development and application value.

Technical content of the invention:

The invention provides a method for preparing a ginsenoside derivative using ginsenoside or a plant containing ginsenoside as a raw material. The method is simple, convenient, and low in cost, and can be used to prepare low-polar ginsenosides and their derivatives on a large scale and in batches. Materials, characterized in that catalysts and high-temperature pyrolysis (or steaming) are necessary or necessary conditions of the present invention.

In the method provided by the present invention, the raw materials used are any plants containing ginsenosides (such as rhizomes and leaves of ginseng, panax notoginseng, American ginseng, and Gynostemma pentaphyllum and their products) and their tissue cultures. , Root, stem, leaf, etc.) and any form (tissue block, powder or extract thereof), or monomer ginsenoside or a mixture of two or more monomer ginsenosides of any of the following purity: Natural ginsenoside: Rb ^ Rb ₂ , Rb ₃ , Rc, Rd, R _gl , Re and Rf, etc .;

Glycol type ginsenosides with free 3 hydroxyl groups: 20-O-β glucose-20 (S) -protopanaxadiol [20-O- β-D-glucopyranosyl -20 (S) -protopanaxadiol, CK for short], 20 -O- -L- arabinose (1-6)-β-D-glucose-20 (S) -protopanaxadiol [20-〇- a -L-arabinopyranosyl (1-6)-β-D-glucopyranosyl 20 (S) -protopanaxadiol, CY for short, 20-O- -L-arabinose (1-6)-β-D-glucose-20 (S) -protopanaxadiol [20-O- α -L- ambinofuranosyl (1 → 6)-β -D-glucopyranosyl 20 (S) -protopanaxadiol, referred to as Mc〗 and 20-O- β -D-xylose- β -D-glucose-20 (S) -protopanaxadiol [ 20-O- β -D -xylopyranosyl (l → 6)-β -D-glucopyranosyl- 20 (S) -protopanaxadiol (referred to as Mx); Triol-type ginsenosides with 6 hydroxyl groups free: 20-O-β-D-glucose-20 (S) -protopanaxadiol [20-〇-β-D-glucopyranosyl-20 (S) -protopanaxatriol, referred to as F !].

In the method provided by the present invention, the catalyst used is one of the following acids or two or more mixed acids. (1) Polybasic organic acids such as oxalic acid, malonic acid, succinic acid, butanedioic acid, tartaric acid, malic acid, citric acid, adipic acid, phthalic acid, aspartic acid, glutamic acid, etc .; (2) ) -Methyl organic acids such as amino acids, uronic acid, formic acid, glacial acetic acid, lactic acid, propionic acid, butyric acid, valeric acid, benzoic acid, salicylic acid, sulfosalicylic acid, benzenesulfonic acid, monofluoroacetic acid, two Fluoroacetic acid, trifluoroacetic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, etc .; (3) Inorganic acids such as boric acid, hydrochloric acid, sulfuric acid, phosphoric acid, etc. The molar ratio of ginsenoside to catalyst is 1: 0.01 to 1: 1; the catalyst is used by preparing the catalyst as an aqueous solution and infiltrating and mixing it with raw materials and steaming.

In the method provided by the present invention, the pyrolysis temperature is 110 to 180 ° C, and the time is 0.5 to 10 hours. In the method provided by the present invention, the catalyst is an acid, and a wide range of options can be used. Inorganic strong acids such as nitric acid have great damage to saponins, and are not suitable for use as the final product is mostly food or pharmaceuticals. Comprehensive factors such as hydrolysis time, yield, process, cost and quality, malonic acid and succinic acid are the best choices. The type of catalyst (acidity) and the amount (addition amount) are directly related to the pyrolysis temperature and reaction time: 1. The relationship between the type and amount of the catalyst and the optimal temperature is that when the optimal temperature is exceeded, saponin destruction increases, and vice versa The required pyrolysis time is prolonged; 2. When the amount of catalyst exceeds the most applicable amount, saponin destruction increases, and conversely, the required pyrolysis time increases. Taking catalyst malonic acid and succinic acid as examples, the optimal molar ratio of ginsenoside to catalyst is 1: 0.3 ~ 1: 0.5, the optimal temperature for pyrolysis is 120 ° C, and the optimal reaction time is 4 to 6 hours. .

In the method provided by the present invention, pyrolysis needs to be performed in a closed container such as a pressure cooker, and the heating medium may be steam, air, carbon dioxide, nitrogen, an inert gas, or two or more of them. When using non-steam as a heating medium, a small amount of water should be added to the container to keep the raw materials moist and improve the reaction efficiency.

In the method provided by the present invention, the prepared low-polar ginsenosides and their aglycones are: (1) Glycol type ginsenoside with free hydroxyl group at position 20

Ginsenoside _{20- (R) -Rg 3, 20-} (S) -Rg 3, 20- (R) -Rh 2 20- (S) -Rh 2.;

(2) Triol-type ginsenoside free from hydroxyl group at position 20

Ginsenosides 20- (R) -Rg ₂ , 20- (S) -Rg ₂ ,

(3) Glycol type ginsenosides with 20-position ethylenic bonds

^ 20 ( ₂₁ ) _diol type ginsenoside: ^,;

20 (22) —diol type ginsenosides: _Rg5 , ₃ , _Rs4 .

(4) Triol type ginsenoside with ethylenic bond at position 20

^ 20 ( ₂₁ ) —triol-type ginsenosides: _Rg6 , ^ 3, _Rs7 ,

Δ ^{20 (22)} -triol type ginsenosides: F ₄ , R ₄ , Rs _6;

(5) Glycol ginsenosides

Protopanaxadiol (PPD);

(6) Triol type ginsenoside

Protopanaxatriol (PPT);

(7) Glycol ginsenoside derivatives

3β, 12 β-dihydroxy-20 (21), 24 (25) -diene-dammarane [dammar-3 β, 12 β -dihydroxyl-20 (21), 24 (25) -diene, abbreviations. ( ²¹ ) -PPD],

3β, 12 β-dihydroxy-20 (22), 24 (25) -diene-dammar [dammar-3 β, 12 β-dihydroxyl-20 (22), 24 (25) -diene, abbreviations / ^ ^{2 ()} ( ²² ) -PPD];

(8) Triol type ginsenoside derivatives

3β, 6α, 12 β-trihydroxyl-20 (21), 24 (25) -diene-dammarane [dammar-3 β, 6 α, 12 β -trihydroxyl-20 (21), 24 (25)- diene, referred to as ^{20 (21)} -PPT],

3β, 6α, 12 β-trihydroxyl-20 (22), 24 (25) -diene-dammar [dammar-3 β, 6 α, 12 β-trihydroxyl-20 (22), 24 (25)- diene, referred to as Zl ² ° ( ²² ) -PPT]. In the method provided by the present invention, different raw materials will obtain different pyrolysis products as shown in Table 1:

Table 1. Pyrolysis products of different raw materials under different conditions

In addition, there are aglycon lysates such as phenolic compounds and polyacetylenic compounds, the amount of which increases with increasing acidity, temperature, and time during pyrolysis.

In the method provided by the present invention, the conversion rate of the raw ginsenoside is 96%, and the total yield of the main product is 90%.

In the method provided by the present invention, the prepared product can be used in the form of a low-polar ginsenoside mixture and dried in a conventional method, and can be directly used in the fields of medicines, cosmetics, and health functional foods. It can also be combined with separation and purification technologies. Preparation of various low-polar ginseng soaps according to claim 2 in batches 5

6

Glycomonomer. The purified low-polar ginsenoside monomer or a mixture thereof can be prepared into various dosage forms by combining with various legal pharmaceutical or food excipients and complexing agents, and used in the fields of medicine, cosmetics and health functional foods; It can also be used as a raw material for the synthesis of other biologically active compounds.

In the method provided by the present invention, the method is also applicable to triterpenoid saponins other than ginsenosides such as Notoginsenosides, Gypenosides, Vietnamese ginsenosides, and betene tetraol. (Betulafolientetraol)> Betulafolientetraol A, Betulafolienpentaol, Dammarenediol, Dama-24-ene-3 β, 20-diol-3- Acetate (Dammar-24-ene-3 β, 20-diol-3-acetate). Hydroxyldammarenone Octillone, Kapurol, Borneol Kapurone, Dryobalanone, Dryobalanonoloic acid, etc. From these triterpenoid saponins or plants containing these triterpenoid saponins (including any part of the plant and any existing forms such as tissue blocks, powders or extracts thereof, etc.) or plant cultures containing these triterpenoid saponins as starting materials, The corresponding low-polar triterpenoid saponins or aglycones of triterpenoid saponins are prepared.

The invention clarifies the catalyst required for the high-temperature pyrolysis of ginsenosides, solves the necessary or necessary conditions for the high-temperature pyrolysis conversion of red ginseng to produce natural ginsenosides, and provides a simple and efficient method for the large-scale preparation of low-polar ginsenosides. The method provided by the present invention is used to prepare low-polar ginsenosides and derivatives thereof. The process is simple, the quality is controllable, the aglycon conversion rate of the raw material is high (96%), and the total yield of the main product aglycon is high (90%). low cost. Based on the combined separation and purification technology, various low-polarity ginsenoside monomers can be prepared in large quantities.

detailed description:

Example 1

Glycol ginsenoside (25g) and 45% malonic acid aqueous solution (5ml) were soaked and mixed, put in an autoclave, and pyrolyzed at 120 ° C for 5 hours. Pyrolysis products (HPLC analysis showed that the pyrolysis conversion rate was 96%, the main products were 20- (R) -Rg ₃ , 20- (S) -Rg ₃ , Rg ₅ and 1¾), and 100 mL of water was added The solution formed a suspension, which was extracted three times with methylene chloride. After dichloromethane was removed from the aqueous phase under reduced pressure, 30 ml of ethanol (1000 ml) was added thereto. The dissolved solution was subjected to adsorption resin column chromatography, and 30% ethanol After elution and impurity removal, low-polar saponin was recovered by elution with 90% ethanol. Concentrated under reduced pressure, a large amount of precipitate was precipitated, and 20- (R) -Rg ₃ (2.05g) was obtained after filtration; 1/5 parts of acetone was added to the filtrate, and after standing for 12 hours, a white precipitate was deposited, and separated on a reverse-phase preparation column for separation (Mobile phase is 65% ethanol) 20- (S) -Rg ₃ (2.3g), Rg ₅ (1.8g) and R¾ (1.4g

Example 2

The triol-type ginsenoside (25g) was mixed with a 45% aspartic acid aqueous solution (5ml), mixed and placed in an autoclave, and pyrolyzed at 120 ° C for 5 hours. Pyrolysis products (HPLC analysis shows that the pyrolysis conversion rate is 96%, and the main products are 20 (R) -Rg ₂ , 20 (S) -Rg ₂ , Rg ₆ , F ₄ , 20- (R) -Rh ^ 20- (S) -Rh !, Rh ₄ and Rk ₃ ), adding 100 mL of an aqueous solution to form a suspension, extracting three times with dichloromethane, removing the dichloromethane from the aqueous phase under reduced pressure, and then adding 30% to it 1000 ml of ethanol, and the dissolved solution was subjected to adsorption resin column chromatography. After 30% ethanol was used to remove impurities, eluted with 90% ethanol to recover low-polar saponins. The ethanol solution was concentrated under reduced pressure to obtain a white powder (9 g); the precipitate was prepared by reversed phase (65% ethanol in mobile phase) and normal phase (chloroform / methanol / water = 7/3/1 lower mobile phase) preparative column After separation, 20 (R) -Rg ₂ (0.8 g), 20 (S) -Rg ₂ (0.83g), Rg ₆ (1.14g), F ₄ (1.10g), 20 (R) -R! (0.5 g), 20 (S) -R ! (0.55g), R 4 (1.3g) and Rk ₃ (1.23g).

Example 3

Glycol ginsenoside (25g) was soaked with 9mol / L sulfuric acid (5ml), mixed, placed in an autoclave, and pyrolyzed at 120 ° C for 5 hours. Pyrolysis products (HPLC analysis shows that the pyrolysis conversion rate is 96%, and the products are side chain cyclic panaxadiol PD and a small amount of 20 (R) -Rh ₂ , 20 (S) -Rh ₂ , Rh ₃ and Rk ₂ ), Add 1,000 mL of water to dissolve, perform adsorption resin column chromatography to elute 30% ethanol to remove impurities, and then elute with 90% ethanol to recover low-polar saponins. The ethanol was removed under reduced pressure, and a large amount of precipitate (6.4 g) was precipitated. This precipitate was separated on a reversed-phase preparative column (65% ethanol in mobile phase) to obtain PD (2.3g), Δ ^{20 (22)} -PPD (0.4g), 20- (R) -Rh ₂ (0.38g), 20- (S) -Rh ₂ (0.34 g), R ₃ (0.44 g) and Rk ₂ (0.51 g). Example 4

Glycol ginsenoside (25g) was soaked in 50% formic acid aqueous solution (5mL), placed in an autoclave, and pyrolyzed at 120 ° C for 5 hours. HPLC analysis of the pyrolysis products showed that the pyrolysis conversion was ^ 96%, and the products were mainly 20 (R) -Rh ₂ , 20 (S) -Rh ₂ , Rh ₃ , Rk ₂ and PD. After adding 1000 mL of water to dissolve it, it was subjected to adsorption resin column chromatography to elute 30% ethanol to remove impurities, and then eluted with 90% ethanol to recover low-polar saponin. The ethanol in the collected solution was removed under reduced pressure, and a large amount of a precipitate (8.9 g) was deposited. This precipitate was separated on a reversed-phase preparative column (65% ethanol in mobile phase) to obtain 20 (R) -Rh ₂ (1.8g), 20 (S) -Rh ₂ (1.4g), and Rh ₃ (1.7g). , Rl¾ (1.9g) and panaxadiol (1.3g).

Example 5

Ginsenoside CK (5.0g) was wet-mixed with 45% glucuronic acid (5 mL), placed in an autoclave, and pyrolyzed at 120 ° C for 5 hours. HPLC analysis of the pyrolysis product showed that the conversion rate was 96% The products are mainly 20- (R) -PPD, 20- (S) -PPD, A ²⁰ ( ²¹ ) -PPD and ( ²² ) -PPD. In the latter, 1000 mL of 40% ethanol was added to dissolve it, and adsorption resin column chromatography was performed (after 40% ethanol eluting and removing impurities, eluting with 90% ethanol to recover low-polar saponin). The ethanol in the collected solution was removed under reduced pressure, and a large amount of a precipitate (6.4 g) was precipitated. The precipitate was separated and purified by silica gel chromatography (eluent: petroleum ether / ethyl acetate = 8/1) to obtain 20- (R) -PPD (0.74g), 20- (S) -PPD (0.64g), ^{20 (21)} -PPD (0.54g) and ²⁰ ( ²² ) _PPD (0.71g) _o

Example 6

Ginsenoside (5.0g) was wet-mixed with 68% glycine (5 mL), placed in an autoclave, and pyrolyzed at 120 ° C for 5 hours. HPLC analysis of the pyrolysis product showed that the conversion rate was 96%, and the product was mainly 20- (R) -PPT, 20- ( S) -PPT, Δ 20 (21) -PPT and ^{2 ⁽²²⁾ -PPT} (). The latter was dissolved by adding 1000 mL of water, and subjected to adsorption resin column chromatography. After 30% ethanol was used to remove impurities, eluted with 90% ethanol to recover low-polar saponins. The ethanol in the collected solution was removed under reduced pressure, and a large amount of precipitate (6.4 g) was precipitated. The precipitate was chromatographed on silica gel (eluent: petroleum ether / ethyl acetate = 8/1), respectively 20- (R) -PPD (0.71g), 20- (S) -PPD (0.66g), ^{20 ( 21)} -PPD (0.52g) and l20 ( ²²⁾ -PPD (0.73g).

Claims

Rights request

1. A method for preparing low-polar ginsenosides and aglycones by catalytic pyrolysis, characterized in that the raw ginsenosides are acid-catalyzed and steamed at a high temperature of 110 to 180 ° C for 0.5 to 10 hours.

2. The method for preparing low-polar ginsenosides and their aglycones by catalytic pyrolysis according to claim 1, characterized in that: the molar ratio of ginsenosides to the catalyst is 1: 0.01 to 1: 1; the method of using the catalyst is to The catalyst prepared as an aqueous solution is infiltrated and mixed with raw materials and then steamed.

3. The method for preparing low-polar ginsenosides and their aglycones by catalytic pyrolysis according to claim 1, characterized in that the catalyst used is one of the following acids or two or more mixed acids:

(1) Polybasic organic acids such as oxalic acid, malonic acid, succinic acid, succinic acid, tartaric acid, malic acid, citric acid, adipic acid, phthalic acid, aspartic acid, glutamic acid, etc .;

(2) -Methyl organic acids such as amino acid, uronic acid, formic acid, glacial acetic acid, lactic acid, propionic acid, butyric acid, valeric acid, benzoic acid, salicylic acid, sulfosalicylic acid, benzenesulfonic acid, monofluoroacetic acid , Difluoroacetic acid, trifluoroacetic acid, monochloroacetic acid, dichloroacetic acid, trichloroacetic acid, etc .;

(3) Inorganic acids such as boric acid, hydrochloric acid, sulfuric acid, and phosphoric acid.

4. The method for preparing low-polar ginsenosides and their aglycones by catalytic pyrolysis according to claim 1, characterized in that the raw materials used are any plants and tissue cultures containing ginsenosides, including any part of the plant and any Existing form, or monomer ginsenoside or a mixture of two or more monomer ginsenosides of any of the following purity:

Natural ginsenosides: Rt ^ Rb ₂ , Rb ₃ , Rc, Rd, Rg ^ Re and Rf;

Glycol type ginsenosides with 3 hydroxyl groups free: 20-O-β-D-glucose-20 (S) -protopanaxadiol [20-O-β-D-glucopyranosyl-20 (S) -protopanaxadiol, referred to as CK ], 20-O- -L- arabinose (1-6)-β-D-glucose-20 (S) -protopanaxadiol [20-〇- -L-arabinopyranosyl (1 → 6)-β -D -glucopyranosyl 20 (S) -protopanaxadiol, CY for short, 20-O-ct-L-arabinose (1 → 6)-β-D-glucose-20 (S) -protopanaxadiol [20-O- a -L-arabinoforanosyl (1-6)-β-D-glucopyranosyl 20 (S) -protopanaxadiol (Mc for short), 20-O- β -D-xylose- β-D-glucose-20 (S) -protopanaxadiol [20-O- β-D -xylopyranosyl (l-6)-β-D-glucopyranosyl- 20 (S) -protopanaxadiol, referred to as Mx];

Triol-type ginsenosides with a free hydroxyl group at the 6-position: 20-O-β-D-glucose -20 (S) -protopanaxadiol [20-Ο-β-D-glucopyranosyl-20 (S) -protopanaxatriol, abbreviated as.

5. The method for preparing low-polar ginsenosides and their aglycones by catalytic pyrolysis according to claim 1, wherein the low-polar ginsenosides and their aglycones are:

(1) Glycol type ginsenoside with free hydroxyl group at position 20:

Ginsenosides 20- (R) -Rg ₃ , 20- (S) -Rg ₃ , 20- (R) -R ₂ and 20- (S) -Rh ₂ ;

(2) Triol-type ginsenosides 20- (R) -Rg ₂ , 20- (S) -Rg ₂ , 20- (R) -Rh n 20- (S) -Rh ₁ free at the hydroxyl group at position 20 _;

(3) Glycol type ginsenoside with ethylenic bond at position 20:

^ 0 ( ₂₁ ) -diol type ginsenoside: _ι , ₂ , _Rs5 .

Z ^2G ( ² -diol type ginsenosides: Rg ₅ , Rh ₃ , Rs ₄ ;

(4) Triol type ginsenosides with ethylenic bond at position 20:

2 ^Q ( ²¹ ) -triol type ginsenoside: Rg ₆ , Rk ₃ , Rs _7;

Δ ^{20 (22)} -triol type ginsenosides: F ₄ , R ₄ , Rs _6;

(5) Glycol ginsenosides

Protopanaxadiol (PPD);

(6) Triol type ginsenoside

Protopanaxatriol (PPT);

(7) Glycol ginsenoside derivatives

3 β, 12 β -dihydroxy-20 (21), 24 (25) -diene-dammarane [dammar-3 β, 12 β -dihydroxyl-20 (21), 24 (25) -diene _{5 for} short ^{2 (21)} -PPD],

3 β, 12 β -dihydroxyl-20 (22), 24 (25) -diene-dammar [dammar-3 β, 12 β -dihydroxyl-20 (22), 24 (25) -diene, abbreviated ² ° ( ²² ) -PPD];

(8) Triol type ginsenoside derivatives: 3 β, 6 α, 12 β -trihydroxyl-20 (21), 24 (25) -diene-dammarane [dammar-3 β, 6 α, Ι2 β -trihydroxyl-20 (21), 24 (25 ) -diene, referred to as ^{20 (21)} -PPT],

3 β, 6 α, 12 β -trihydroxyl-20 (22), 24 (25) -diene-dammar [dammar-3 β, 6 α, 12 β-trihydroxyl-20 (22), 24 (25 ) -diene _{5 is} referred to as \ ^{20 (22)} -PPT].

6. The method for preparing low-polar ginsenosides and their aglycones by catalytic pyrolysis according to claim 1, characterized in that: the method is also applicable to triterpenoid saponins other than ginsenosides such as notoginsenosides , Gypenosides, Vietnamese ginsenosides, Betulafoiientetraol, Betulin tetraol A

(Betulafolientetraol A), Betolafolienpentaol, Dammarenediol. Dammar-24-ene-3 β, 20-diol-3-acetate (Dammar-24-ene- 3 β, 20-diol-3-acetate) Hydroxyldammarenone, Octillone, Kapurol, Kapurone, Dragon Dryobalanone, Dry obalanonoloic acid; from these triterpenoid saponins or plants containing these triterpenoid saponins including any part of the plant and any existing form such as tissue mass, powder or extract thereof Or a plant culture containing these triterpenoid saponins as starting materials to prepare corresponding low-polar terpenoid saponins or aglycones of triterpenoid saponins.

7. The method for preparing low-polar ginsenosides and their aglycones by catalytic pyrolysis according to claim 1, characterized in that the prepared product is directly dried for use in the form of a low-polar ginsenoside mixture and dried by a conventional method. Pharmaceuticals, cosmetics and health functional foods; or,

In combination with the separation and purification technology, the various low-polar ginsenoside monomers according to claim 5 are prepared in large quantities, or further mixed with various legal pharmaceutical or food excipients and complexing agents to prepare various dosage forms. It is used in the fields of pharmaceuticals, cosmetics and health functional foods; or as a raw material for synthesizing other biologically active compounds.