CN115626948A - Novel spirostanin monomer and preparation method thereof - Google Patents
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Abstract
The invention discloses a novel spirostanin monomer, namely spirostan-5,25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside, and a preparation method thereof. Adsorbing the water extract of rhizoma Polygonati Odorati with macroporous adsorbent resin, eluting with ethanol, concentrating under reduced pressure to obtain rhizoma Polygonati Odorati extract, performing silica gel column chromatography and ODS column chromatography, and refining by preparative high performance liquid chromatography to obtain the new spirostanol saponin monomer. The obtained new spirostanol saponin monomer can be used for quality control of traditional Chinese medicinal materials polygonatum odoratum or fresh polygonatum odoratum of agricultural products.
Description
Technical Field
The invention relates to a new spirostanol saponin monomeric compound extracted and separated from polygonatum odoratum and a preparation method thereof, belonging to the field of natural medicinal chemistry research.
Background
Polygonatum odoratum (Mill.) Druce) is a perennial herb of Polygonatum (Polygonatum) of Liliaceae (Liliaceae), and is named as radix scrophulariae, rhizoma corydalis, bellam and fragrant solomonseal rhizome. Mainly distributed in east Asia and Europe, and widely planted in Hunan, jiangsu and Jilin provinces of China.
Rhizoma Polygonati Odorati is a typical medicinal and edible plant, and can be used as Chinese medicinal material after rhizome drying and slicing treatment, has effects of nourishing yin, moistening dryness, promoting fluid production, and quenching thirst, and can be used for treating diseases such as lung and stomach yin injury, dryness-heat cough, dry throat, thirst, internal heat, and diabetes.
The chemical components separated from rhizoma Polygonati Odorati mainly comprise steroid saponin, homoisoflavonoid, polysaccharide, triterpenes, anthraquinone, alkaloid and volatile oil, wherein the steroid saponin is one of the main components of rhizoma Polygonati Odorati with pharmacological activity. Research shows that the compound separated from the polygonatum has the functions of regulating immunity, resisting tumor, reducing blood sugar, resisting aging, resisting oxidation, resisting virus, losing weight and the like.
Disclosure of Invention
The invention provides a new spirostanin monomeric compound spirostan separated from rhizomes of polygonatum odoratum, namely 5,25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside (hereinafter referred to as compound A) and a preparation method thereof.
The new spirostanin monomer spirostan-5,25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside has a structural formula
The invention also provides a preparation method of a new spirostanin compound monomer, namely spirostan-5, 25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside, which comprises the following steps:
(1) Homogenizing rhizoma Polygonati Odorati with small amount of water by wall breaking machine, adding water, stirring for extraction or pulverizing dried rhizoma Polygonati Odorati, decocting in water, and centrifuging to obtain rhizoma Polygonati Odorati water extractive solution.
(2) Adsorbing the extracting solution obtained in the step (1) by macroporous adsorption resin, and eluting by using ethanol.
(3) And (3) concentrating the eluent obtained in the step (2) under reduced pressure, precipitating with 7 times of ethanol, and concentrating the supernatant to obtain the polygonatum odoratum total steroid saponins.
(4) And (4) mixing the polygonatum odoratum total steroid saponins obtained in the step (3) according to a volume ratio of 50:1:0.01 to 6:4.5:2, using ethyl acetate-ethanol-water mixed solvent as eluent to carry out silica gel column chromatography gradient elution, carrying out TLC (thin layer chromatography) inspection, and combining the components containing the compound A.
(5) And (5) decompressing the component containing the compound A obtained in the step (4) to recover the solvent, and mixing the solvent again according to the volume ratio of 9:2.7:0.1 to 15:10:2, taking a dichloromethane-methanol-water mixed solvent as an eluent to carry out silica gel column chromatography gradient elution, carrying out TLC (thin layer chromatography) inspection, and combining the components containing the compound A.
(6) And (3) decompressing the component containing the compound A obtained in the step (5) to recover the solvent, and performing solvent recovery again according to the volume ratio of 2:1 to 5: performing ODS column chromatography gradient elution with mixed solvent of methanol-water as eluent, performing TLC inspection, and mixing the component containing compound A.
(7) And (3) recovering the solvent from the component containing the compound A obtained in the step (6) under reduced pressure, carrying out isocratic elution by using a preparative high performance liquid chromatography (RID detector) and acetonitrile-water (43.
In the step (1), when the wall of the fresh polygonatum is broken and homogenized, the weight-volume ratio of the fresh polygonatum to the water is 1:2, centrifuging, weighing, adding water (weight volume ratio) which is 10 times of the weight of the residue, stirring and extracting at normal temperature for 3 times, wherein the stirring time is 5min, and combining the extracting solutions for 4 times for later use, wherein the extracted filter residue contains almost no steroidal saponin compounds.
The invention adopts wet column loading and dry sample loading, and the weight ratio of the sample used for sample mixing to the stationary phase is 1:2; the weight ratio of the silica gel column chromatography sample to the silica gel is 1:30 to 1:60, adding a solvent to the mixture; the weight ratio of the ODS column chromatography sample to the stationary phase is 1:100.
the silica gel column chromatography eluent solvent system used in the invention is ethyl acetate-ethanol-water, and the preferred volume ratio is 50:1:0.01 to 6;4.5:2 ethyl acetate-ethanol-water; another silica gel column chromatography eluent solvent system is dichloromethane-methanol-water, preferably in a volume ratio of 9:2.7:0.1 to 15:10:2 dichloromethane-methanol-water; the ODS column chromatography eluent solvent system is methanol-water, and the preferable volume ratio is 2:1 to 5:1 methanol-water; the eluent solvent system of the preparative high performance liquid chromatography is acetonitrile-water, and the preferable volume ratio is 43:57 acetonitrile-water.
The chromatographic column used in the purification process of the step (6) of the invention is Agilent eclipse XDB-C18 (10X 250mm,10 μm), the detector is a differential refraction detector, the column temperature is 25 ℃, and the flow rate is 2.0mL/min.
The chemical structure of the separated compound A is identified by means of NMR, MS and the like, and the structure identification process and data are as follows:
the compound A is white powder, is easily soluble in water and methanol, and is hardly soluble in ethyl acetate, petroleum ether, chloroform and the like. And (4) detecting by thin-layer chromatography, wherein the reagent A is yellow, and the reagent E is not. HR-ESI-MS gives a molecular ion peak of M/z897.4399[ M + H-H 2 O] + (calcd.897.4478forC 45 H 69 O 18 ) From this, it is known that the molecular formula is C 45 H 70 O 19 。 13 CNMR Spectroscopy (C) 5 D 5 N,150 MHz), giving a total of 45 carbons, and combining the DEPT90 ° and DEPT135 ° spectra, compound a contained 3 primary carbons, 14 secondary carbons, 22 tertiary carbons, 6 quaternary carbons. By 13 The CNMR and DEPT spectrograms show that 3 methyl signals appearing in the high field area are respectively delta C 15.4(C-21)，δ C 19.4(C-19)，δ C 20.1 (C-18) lacks a characteristic methyl peak of mother nucleus, and the low field region has delta except a pair of characteristic double bonds of 140.6 (C-5) and 122.4 (C-6) C 144.6 quaternary carbons, 108.8 Zhong Tanfeng, suggest that there may be a further pair of double bonds present and that one of the carbons is a terminal olefinic carbon, presumably forming a double bond at positions 25 and 27. In addition, the 13 Delta appears in the CNMR spectrum C 107.1,δ C 105.4，δ C 102.73 carbohydrate end group carbon signals, while delta can be observed C 60.5(CH 2 ),61.7(CH 2 ),63.3(CH 2 ) 86.5 (CH). These carbon spectrum data preliminarily indicate that compound a is a spirosteroid compound having a hydroxyl group attached to the spirosteroid nucleus at position 14, two double bonds, and three sugar groups.
In that 1 HNMR(C 5 D 5 N,600 MHz) and HSQC, low field region delta C 102.7 and delta H 4.77(1H,d,J＝7.8Hz)，δ C 105.3 and delta H 5.02(1H,d,J＝7.8Hz)，δ C 107.1 and delta H 5.11 (1H, D, J = 7.2Hz), ascribed to the terminal carbon, hydrogen signals of the sugars, further demonstrating the presence of 3 sugar groups and the β -D configuration of all three sugars, δ C122.4 (C-6) and δ C H 5.27 (1H, H-6) correlation,. Delta. C 108.82 (C-27) and alkene Hydrogen Signal δ H 4.67 (2H, H-27). High field region delta C 19.4 (C-19) and δ H 0.85 (3H, s) correlation,. Delta. C 20.1 (C-18) and δ H (0.95,3H,s)，δ C 15.4 (C-21) and δ H 1.02 (3H, d, J = 7.2Hz), assigned to the carbon, hydrogen signal of 3 methyl groups.
From HMBC,. Delta. H 4.67 (2H, H-27) and delta C 29.1(C-24),δ C 65.1 (C-26), there is a remote correlation. Delta H 0.85 (3H, s, H-19) is remotely related to C-5,C-9,C-10, C-1; delta H 0.95 (3H, s, H-18) is remotely related to C-12, C-13, C-14, C-17; delta. For the preparation of a coating H 1.02 (3H, d, H-21) is remotely related to C-17, C-20, C-22; galactose end group proton delta H 4.77 (1H, d, J = 7.2Hz) and the C-3 bit delta of the mother nucleus C 78.20 there is a remote correlation; glucose end group proton delta H 5.02 (1H, d, J =7.8 Hz) and galactose delta C 81.2 (C-4') remote correlation; delta H 5.11 (1H, d, J=7.8Hz) and glucose delta C 86.3 (C-2') remote correlation, thereby determining that the glycosyl sequence is glucose- (1 → 2) -glucose- (1 → 4) -galactose-. In conclusion, the analysis confirms that the compound A is spirosta-5, 25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside, and the compound is searched by the literature to be a novel compound which is not reported.
Of Compound A 13 CNMR (150 MHz) and 1 HNMR data (600 MHz) pyridine-d5
HPLC-ELSD chromatographic conditions for detecting the purity of compound A are as follows:
a chromatographic column: agilentSBC-18 (4.6X 250mm,5 μm)
Mobile phase: acetonitrile-water (34; flow rate: 1L/min; column temperature: 30 ℃; sample introduction amount: 15 μ L.
ELSD detector, drift tube temperature 100 deg.C; and (3) an impact state: and (5) closing.
Carrier gas pressure: 0.45Mpa; flow rate of the atomizer: 2.7L/min; magnification: 1.0 times.
Drawings
FIG. 1 Mass Spectroscopy of Compound A
FIG. 2 preparation of Compound A 13 CNMR spectrogram
FIG. 3 DEPT90 ℃ and DEPT135 ℃ spectra of Compound A
FIG. 4 preparation of Compound A 1 HNMR spectrogram
FIG. 5 HMBC spectrum of Compound A
FIG. 6 HSQC spectrum of Compound A
FIG. 7 preparation of Compound A 1 H- 1 HCOSY spectrum
Detailed Description
Example 1
(1) Taking 50Kg of fresh polygonatum odoratum rhizome, adding 100L of water, stirring and homogenizing for 5min by using a wall breaking machine, centrifuging, weighing filter residues, and mixing the filter residues and distilled water according to a weight-volume ratio of 1:10 adding water, stirring and extracting for 3 times for 10min, centrifuging, and mixing the 4 filtrates to obtain rhizoma Polygonati Odorati water extractive solution. At this time, steroid saponin component is not detected in the residue
(2) Adsorbing the extracting solution obtained in the step (1) by using D101 macroporous adsorption resin, and eluting by using 85% ethanol to obtain the extracting solution containing the steroid saponins of the bamboos.
(3) And (3) concentrating the eluent obtained in the step (2) under reduced pressure, precipitating with 7 times of ethanol, and concentrating the supernatant to obtain 210g of polygonatum odoratum total steroid saponins.
(4) Mixing 210g of the polygonatum odoratum total steroid saponins obtained in the step (3) with a mixed solvent of ethyl acetate-ethanol-water (50): 1:0.01 to 6:4.5: and 2, performing silica gel column chromatography gradient elution by using eluent as eluent, detecting by TLC, combining the components containing the compound A, and recovering the solvent under reduced pressure to obtain 120g of the component C containing the compound A.
(5) Dissolving 120g of the component C containing the compound A obtained in the step (4) by using 70% ethanol, and then adding a mixture of dichloro-methanol-water in a volume ratio of 9:2.7:0.1 to 15:10: and 2, performing silica gel column chromatography gradient elution by using eluent, detecting by TLC, combining the components containing the compound A, and recovering the solvent under reduced pressure to obtain the component C-a7g containing the compound A.
(6) And (3) mixing 7g of the component C containing the compound A obtained in the step (5) in a methanol-water volume ratio of 2:1 to 5: and 1, performing ODS reversed phase column chromatography gradient elution by using an eluent, detecting by TLC, collecting a component of the compound A, and recovering the solvent under reduced pressure to obtain a crude product of the compound A, wherein the crude product is 60mg.
(7) The crude compound a obtained in step (6) was purified by preparative high performance liquid chromatography (RID detector) using acetonitrile-water (43).
Example 2
(1) Chopping 20kg of fresh rhizoma Polygonati Odorati, soaking in 10 times (weight/volume ratio) of 70% ethanol for 3 times for 12 hr, filtering, and mixing filtrates to obtain rhizoma Polygonati Odorati ethanol extract.
(2) Concentrating the extracting solution obtained in the step (1) until no ethanol smell exists, adding distilled water with the volume 5 times of that of the extracting solution for dilution, adsorbing the extracting solution by using AB-8 macroporous adsorption resin, eluting the eluting solution by using 80% ethanol, concentrating the eluent under reduced pressure, precipitating the eluent by using ethanol with the volume 6 times of that of the eluting solution, and concentrating the supernatant to obtain 75g of the polygonatum total steroid saponin.
(3) Dissolving the polygonatum total steroid saponins obtained in the step (2) by using ethanol, wherein the volume ratio is 50:1:0.01 to 6:4.5:2, performing gradient elution by silica gel column chromatography by using an ethyl acetate-ethanol-water mixed solvent as an eluent, detecting by TLC, combining the components containing the compound A, and recovering the solvent under reduced pressure to obtain 40g of the component C containing the compound A.
(4) And (3) performing silica gel column chromatography again on the component C40g obtained in the step (3) in a volume ratio of 9:2.7:0.1 to 15:10:2, performing silica gel column chromatography gradient elution by taking dichloro-methanol-water as an eluent, detecting by TLC, combining the components containing the compound A, and recovering the solvent under reduced pressure to obtain 2g of the component C-a containing the compound A.
(5) C-a2g obtained in the step (4) is prepared by mixing the components in a volume ratio of 2:1 to 5: performing ODS reversed-phase column chromatography gradient elution with methanol-water as eluent, detecting by TLC, mixing the components containing compound A, and recovering solvent under reduced pressure to obtain crude compound A (55 mg).
(6) And (3) carrying out isocratic elution on 55mg of the crude compound A obtained in the step (5) by using semi-preparative high performance liquid chromatography and acetonitrile-water (43).
Example 3
(1) Pulverizing dried rhizoma Polygonati Odorati 15kg, extracting with 85% ethanol under reflux for 3 times (120L, 90L and 60L, respectively) for 90 min, 60 min and 45 min, filtering, and mixing filtrates to obtain rhizoma Polygonati Odorati extractive solution. At this time, the steroid saponin component was not substantially detected in the residue (TLC detection).
(2) Concentrating the extracting solution obtained in the step (1), adding distilled water with the volume 4 times of that of the extracting solution for dilution, adsorbing the diluted solution by using HP20 macroporous adsorption resin, and eluting the adsorbed solution by using 95% ethanol to obtain the steroid saponin compound-containing eluent.
(3) And (3) concentrating the eluent obtained in the step (2) under reduced pressure, precipitating with 8 times of ethanol, and concentrating the supernatant to obtain 180g of the polygonatum odoratum extract.
(4) Mixing 180g of the extract obtained in the step (3) with a mixture of 50:1:0.01 to 6:4.5:2, performing silica gel column chromatography gradient elution by taking an ethyl acetate-ethanol-water mixed solvent as an eluent, detecting by TLC, combining the components containing the compound A, and recovering the solvent under reduced pressure to obtain 102g of the component C containing the compound A.
(5) Mixing 102g of component C102g containing the compound A obtained in the step (4) in a volume ratio of 9:2.7:0.1 to 15:10:2, performing silica gel column chromatography gradient elution by taking dichloro-methanol-water as an eluent, detecting by TLC, combining the components containing the compound A, and recovering the solvent under reduced pressure to obtain 6g of the component C-a containing the compound A.
(6) And (6) g of the component C-a containing the compound A obtained in the step (5), wherein the volume ratio of the component C-a to the component C-a is 2:1 to 5: performing ODS reversed phase column chromatography gradient elution with methanol-water as eluent, detecting by TLC, mixing the components containing compound A, and recovering solvent under reduced pressure to obtain crude compound A (55 mg).
(7) And (3) isocratic elution is carried out on 55mg of the crude compound A obtained in the step (6) by utilizing semi-preparative high performance liquid chromatography and acetonitrile-water (43).
Claims (8)
1. A new spirostanin monomer, spirostane-5,25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside.
2. A novel preparation method of a spirostanin monomer is characterized in that polygonatum is used as a raw material, water is used for extraction, an extracting solution is absorbed by macroporous absorption resin, an aqueous solution of an organic solvent is eluted, the solvent is recovered under reduced pressure and dried to obtain total steroid saponin containing spirostan-5,25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside, the total steroid saponin is subjected to silica gel column chromatography, ODS column chromatography and preparative high performance liquid chromatography for separation and purification to obtain spirostan-5,25-diene-3 beta, 14 alpha-diol-3-O-beta-D-glucopyranosyl- (1 → 2) -beta-D-glucopyranosyl- (1 → 4) -beta-D-galactopyranoside.
3. The method according to claim 2, wherein the macroporous adsorbent resin is selected from one of AB-8, D101, D4042 and HP-20, or a mixture of two or more thereof.
4. The process according to claim 2, wherein the eluent is a mixed solution of an organic solvent and water in a volume ratio of 20 to 100%, and the organic solvent is selected from ethanol, methanol, acetone, or a mixed solvent of two or more thereof.
5. The process according to claim 2, wherein the mobile phase of the silica gel column chromatography is a mixture of a mobile phase obtained by subjecting the mixture to column chromatography and a solvent in a volume ratio of 50:1:0.01 to 6:4.5:2, the volume ratio of the ethyl acetate-ethanol-water mixed solution is 9:2.7:0.1 to 15:10:2 dichloromethane-methanol-water mixed solution.
6. The preparation method as claimed in claim 2, wherein the ODS column chromatography mobile phase is a mixture of 2:1 to 5:1 of methanol-water.
7. The method of claim 2, wherein the preparative high performance liquid chromatography mobile phase system is a liquid chromatography mobile phase system with a volume ratio of 43:57 acetonitrile-water mixed solution.
8. The method according to claim 2, wherein the polygonatum odoratum is a fresh rhizome of polygonatum odoratum.
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Citations (4)
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|---|---|---|---|---|
| CN1389469A (en) * | 2002-07-04 | 2003-01-08 | 中国科学院昆明植物研究所 | Separation and detection method of spironosaponin and furostsaponin |
| CN108047300A (en) * | 2017-11-30 | 2018-05-18 | 浙江大学 | Steroid saponin compound and preparation method and application |
| WO2021258059A1 (en) * | 2020-06-19 | 2021-12-23 | Kimberly-Clark Worldwide, Inc. | Animal feed composition for reducing ammonia production |
| WO2021258056A1 (en) * | 2020-06-19 | 2021-12-23 | Kimberly-Clark Worldwide, Inc. | Saponin containing extracts prepared from hesperaloe useful in the treatment of non-human animals |
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2022
- 2022-10-12 CN CN202211250304.4A patent/CN115626948A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1389469A (en) * | 2002-07-04 | 2003-01-08 | 中国科学院昆明植物研究所 | Separation and detection method of spironosaponin and furostsaponin |
| CN108047300A (en) * | 2017-11-30 | 2018-05-18 | 浙江大学 | Steroid saponin compound and preparation method and application |
| WO2021258059A1 (en) * | 2020-06-19 | 2021-12-23 | Kimberly-Clark Worldwide, Inc. | Animal feed composition for reducing ammonia production |
| WO2021258056A1 (en) * | 2020-06-19 | 2021-12-23 | Kimberly-Clark Worldwide, Inc. | Saponin containing extracts prepared from hesperaloe useful in the treatment of non-human animals |
| WO2021258055A1 (en) * | 2020-06-19 | 2021-12-23 | Kimberly-Clark Worldwide, Inc. | Saponin containing extracts prepared from hesperaloe useful in the treatment of non-human animals |
Non-Patent Citations (3)
| Title |
|---|
| HONG ZHANG等: "Steroidal sapogenins and glycosides from the fibrous roots of Polygonatum odoratum with inhibitory effect on tissue factor (TF) procoagulant activity", 《STEROIDS》, vol. 89, pages 1 - 10 * |
| TONG JIANG等: "Research on Processing-Induced Chemical Variations in Polygonatum Cyrtonema Rhizome by Integrating Metabolomics and Glycomics", 《MOLECULES》, vol. 27, pages 1 - 21 * |
| 郭焕杰: "玉竹甾体皂苷成分及其活性研究", 《全国硕士论文医药卫生科技辑》, pages 1 - 92 * |
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