CN105837651A - 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid and extraction method thereof - Google Patents
3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid and extraction method thereof Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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Abstract
The invention discloses 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid. The 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid has a structural formula shown in the description. An extraction method of the 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid comprises 1, carrying out percolation extraction on Sauropus rostratus Miq. crude powder as a raw material in an ethanol solvent and evaporating the ethanol solvent so that first extract is obtained, 2, adding water into the first extract to obtain a fluid suspension, adding petroleum ether and ethyl acetate into the fluid suspension, carrying out extraction to obtain extract and evaporating to remove the ethanol solvent in the extract so that second extract is obtained, and 3, taking the second extract, carrying out gradient elution through chloroform and methanol as eluants and carrying out chloroform-methanol flow separation to obtain white powder which is 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid. The method realizes extraction of 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid in Sauropus rostratus Miq., is simple and easy and has a high extraction rate. The 3 beta-hydroxy-26 alpha, 27 beta-arbor-13(18)-ene-24-carboxylic acid has good anti-inflammatory effects.
Description
Technical field
The present invention relates to a kind of compound and extracting method thereof.It is more particularly related to dragon folic acid and carrying
Access method.
Background technology
Dragon leaf Sauropus rostratus Miq. be Euphorbiaceae Sauropus plant, abound with in Indonesia, Vietnam and
The ground such as the Yunnan of China, Guangxi, Fujian.In the middle of among the people use as dietetic therapy medical material using area, Guangdong and Guangxi Provinces, relatively conventional in herbal tea,
There is effect of clearing heat and moistening lung, preventing phlegm from forming and stopping coughing.Dragon leaf has many pharmacologically actives such as antiallergic, antibacterial, anti-inflammatory and antalgic；
Mesh is many clinically to be usually used in treating the respiratory system disease such as pneumonia, bronchitis, such as qianlong.com with the dragon leaf prescription as principal agent
The pneumonia that Diplococcus pneumoniae is caused by mixture (Semen Oroxyli, Long Ye, Radix Pseudostellariae, Radix Ophiopogonis, the Radix Paeoniae Alba, Herba Dendrobii etc.) has prevention and treatment
Effect, qianlong.com's soup (Semen Oroxyli, Herba Houttuyniae, Long Ye, Semen Coicis, the Rhizoma Anemarrhenae etc.) is used for treating interstitial pneumonia, and Gekko Swinhonis tea is (blue or green
Radix Semiaquilegiae, Long Ye, Flos Farfarae, Ba Ji etc.) it is used for treating acute bronchitis.
At present, the material base research to the dragon effect such as leaf active component and antiinflammatory is little both at home and abroad, and its effect
Mechanism and effective substance are still not clear, and strongly limit application and the exploitation of Related product of dragon leaf.We are right
Finding in the pharmacological evaluation of dragon leaf extract, it has certain antiinflammatory action, it is therefore necessary to enter its anti-inflammatory active ingredient
Row further investigation, provides more scientific basis for furtheing investigate its mechanism of action etc., and base is established in the exploitation for dragon leaf
Plinth.
Summary of the invention
It is an object of the invention to solve at least the above, and the advantage that at least will be described later is provided.
It is a still further object of the present invention to provide dragon folic acid, it is extracted from natural plants dragon leaf, has the most anti-
Scorching effect.
In order to realize according to object of the present invention and further advantage, it is provided that a kind of dragon folic acid, its structural formula is such as
Shown in lower:
Additionally provide the extracting method of dragon folic acid, comprise the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then with volume ratio be 60～
The chloroform-methanol flow point of 90:1, obtains white powder, is dragon folic acid.
Preferably, the extracting method of described imperial folic acid, step 1) in, the volume fraction of ethanol is 60～80%,
The usage amount of described alcohol solvent is 8～12 times of dragon leaf coarse powder weight.
Preferably, the extracting method of described imperial folic acid, described step 2) in, the addition petroleum ether in suspension
The extraction temperature of extraction is 60～90 DEG C.
Preferably, the extracting method of described imperial folic acid, described step 3) in, with chloroform and methanol as eluant,
Carrying out gradient elution, be specifically divided into 12 gradients and carry out eluting, the volume ratio of chloroform and methanol is respectively as follows: 100:0,70～90:
1,40～60:1,20～40:1,10～30:1,5～15:1,6～10:1,4～7:1,1～5:1,1～3:1,0.5～2:1,0:
100。
The present invention at least includes following beneficial effect: the present invention extracts dragon folic acid, simple and convenient extraction from Long Yezhong
Easy, extraction ratio is higher, and this compound has good antiinflammatory action.
Part is embodied by the further advantage of the present invention, target and feature by description below, and part also will be by this
Invention research and practice and be understood by the person skilled in the art.
Accompanying drawing explanation
Fig. 1 is dragon folic acid of the present invention13C NMR spectra；
Fig. 2 is dragon folic acid of the present invention1H-NMR collection of illustrative plates.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail, to make those skilled in the art with reference to description
Word can be implemented according to this.
Should be appreciated that used herein such as " have ", " comprising " and " including " term do not allot one or many
Other element individual or the existence of a combination thereof or interpolation.
A kind of dragon folic acid, also known as 3 beta-hydroxy-23,25 β, 26 α, 27 β, 28 β-tetramethyl-21-isopropyl-13
(18)-steroid alkene-24-acid, 3 β-hydroxy-26 α, 27 β-arbor-13 (18)-ene-24-carboxylic acid (9), its
Structural formula is as follows:
The molecular formula of described compound is: C30H48O3；
The relative molecular weight of described compound is: 456.36.
Its mass spectrometric data data of this compound, EI-MS (m/z): 456 [M]+, 457 [M+H]+, 441 [M-CH3]+, 439
[M-OH]+, 439 [M+H-H2O]+, 395 [M+H-H2O-CH3-CHO]+；
This compound13C-NMR spectrogram as it is shown in figure 1, its1H-NMR composes as shown in Figure 2；
This compound13C-NMR spectrum and1H-NMR composes related data, as shown in the table:
Embodiment 1
The extracting method of dragon folic acid, comprises the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 60:1's by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product 3 beta-hydroxy-23,25 β, 26 α, and 27 β, 28 β-tetramethyl-21-is different
Propyl group-13 (18)-steroid alkene-24-acid.
Embodiment 2
The extracting method of dragon folic acid, comprises the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 80:1's by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product 3 beta-hydroxy-23,25 β, 26 α, and 27 β, 28 β-tetramethyl-21-is different
Propyl group-13 (18)-steroid alkene-24-acid.
Embodiment 3
The extracting method of dragon folic acid, comprises the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 90:1's by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product 3 beta-hydroxy-23,25 β, 26 α, and 27 β, 28 β-tetramethyl-21-is different
Propyl group-13 (18)-steroid alkene-24-acid.
Embodiment 4
The extracting method of dragon folic acid, comprises the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 60:1's by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product 3 beta-hydroxy-23,25 β, 26 α, and 27 β, 28 β-tetramethyl-21-is different
Propyl group-13 (18)-steroid alkene-24-acid.
The extracting method of described imperial folic acid, step 1) in, the volume fraction of ethanol is 60%, described alcohol solvent
Usage amount is 8 times of dragon leaf coarse powder weight.
The extracting method of described imperial folic acid, described step 2) in, the extraction adding petroleum ether extraction in suspension
Taking temperature is 60 DEG C.
The extracting method of described imperial folic acid, described step 3) in, with chloroform and methanol as eluant, carry out gradient and wash
De-, be specifically divided into 12 gradients and carry out eluting, the volume ratio of chloroform and methanol be respectively as follows: 80:0,70:1,40:1,20:1,10:
1、5:1、6:1、4:1、1:1、1:1、0.5:1、0:100。
Embodiment 5
The extracting method of dragon folic acid, comprises the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 80:1's by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product 3 beta-hydroxy-23,25 β, 26 α, and 27 β, 28 β-tetramethyl-21-is different
Propyl group-13 (18)-steroid alkene-24-acid.
The extracting method of described imperial folic acid, step 1) in, the volume fraction of ethanol is 70%, described alcohol solvent
Usage amount is 10 times of dragon leaf coarse powder weight.
The extracting method of described imperial folic acid, described step 2) in, the extraction adding petroleum ether extraction in suspension
Taking temperature is 80 DEG C.
The extracting method of described imperial folic acid, described step 3) in, with chloroform and methanol as eluant, carry out gradient and wash
De-, be specifically divided into 12 gradients and carry out eluting, the volume ratio of chloroform and methanol be respectively as follows: 90:0,80:1,50:1,30:1,20:
1、10:1、8:1、5:1、3:1、2:1、1:1、0:100。
Embodiment 6
The extracting method of dragon folic acid, comprises the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains after ethanol evaporation solvent
First extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction
Take, obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 90:1's by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product 3 beta-hydroxy-23,25 β, 26 α, and 27 β, 28 β-tetramethyl-21-is different
Propyl group-13 (18)-steroid alkene-24-acid.
The extracting method of described imperial folic acid, step 1) in, the volume fraction of ethanol is 80%, described alcohol solvent
Usage amount is 12 times of dragon leaf coarse powder weight.
The extracting method of described imperial folic acid, described step 2) in, the extraction adding petroleum ether extraction in suspension
Taking temperature is 90 DEG C.
The extracting method of described imperial folic acid, described step 3) in, with chloroform and methanol as eluant, carry out gradient and wash
De-, be specifically divided into 12 gradients and carry out eluting, the volume ratio of chloroform and methanol be respectively as follows: 100:0,90:1,60:1,40:1,30:
1、15:1、10:1、7:1、5:1、3:1、2:1、0:100。
In order to the anti-inflammatory activity of the compounds of this invention is described, using antibiotic medicine-amoxicillin on the market as to as directed
The excellent antiphlogistic effects of the compounds of this invention.
Experiment material:
Choose the female mice that 60 body weight are 30～32 grams；
(1) all of mice is arbitrarily grouped
Blank group: 20 mices；
Amoxicillin group: 20 mices
Test medicine group group: 20 mices: (the compound dragon folic acid of embodiment 4 preparation that this test medicine uses, adds
With pharmaceutical adjuvant, make lamellar medicament or encapsulated pharmaceuticals)
One, ear swelling experiment of mice
To the mice of different groups respectively to should give following process:
Blank group, by 2.5mg kg-1 normal saline gavage, continuous 5 days, 1h after the 5th day gavage, every mice
Before and after auris dextra, two sides is uniformly coated with dimethylbenzene 0.02mL, prepares auricle inflammatory model.After 2h, collare dislocation puts to death mice, along auricle base
Two ears cut by line, lay round auricle at the same position of two ears respectively with diameter 8mm card punch, claim respectively with electronic balance immediately
Quality, of poor quality as swelling using left and right two ear, weigh and be accurate to 0.0001g；
Amoxicillin group: by 2.5mg kg-1 to mouse stomach amoxicillin, continuous 5 days, 1h after the 5th day gavage, often
Before and after mouse right ear, two sides is uniformly coated with dimethylbenzene 0.02mL, prepares auricle inflammatory model.After 2h, mice, edge are put to death in collare dislocation
Auricle baseline cuts two ears, lays round auricle at the same position of two ears respectively with diameter 8mm card punch, uses electronic balance immediately
Claim quality respectively, of poor quality as swelling using left and right two ear, weigh and be accurate to 0.0001g；
Test medicine group: the compound prepared to mouse stomach embodiment 4 by 2.5mg kg-1, continuous 5 days, fills on the 5th day
1h after stomach, before and after every mouse right ear, two sides is uniformly coated with dimethylbenzene 0.02mL, prepares auricle inflammatory model.Collare dislocation after 2h
Put to death mice, cut two ears along auricle baseline, lay round auricle at the same position of two ears respectively with diameter 8mm card punch, vertical
Quality is i.e. claimed respectively with electronic balance, of poor quality as swelling using left and right two ear, weigh and be accurate to 0.0001g；
Swelling=auris dextra tablet weight left auricle weight
Suppression ratio=(blank group average swelling-average swelling of administration group)/average swelling × 100% of blank group
After causing inflammation, each group mouse right ear occurs highly red and swollen phenomenon at once.Test medicine group and test medicine group are to diformazan
Mice ear caused by benzene all significantly inhibits effect, the results are shown in Table 1.
Table 1 ear swelling experiment of mice result
| Group | Dosage (mg kg-1) | Evaluate swelling (mg) |
| Blank group | 2.5 | 18.6 |
| Amoxicillin group | 2.5 | 6.8 |
| Test medicine group | 2.5 | 7.1 |
As table 1 result understands, after causing inflammation, each group mouse right ear occurs highly red and swollen phenomenon at once.With blank group phase
Ratio, the swelling degree of the mice of amoxicillin group and test medicine group has declined, and shows amoxicillin group and test medicine
Group mice ear caused by xylol all significantly inhibits effect, it was demonstrated that, compound dragon folic acid, namely 3 beta-hydroxies-
23,25 β, 26 α, 27 β, 28 β-tetramethyl-21-isopropyl-13 (18)-steroid alkene-24-acid, there is good anti-inflammatory.
Although embodiment of the present invention are disclosed as above, but it is not restricted in description and embodiment listed
Using, it can be applied to various applicable the field of the invention completely, for those skilled in the art, and can be easily
Realizing other amendment, therefore under the general concept limited without departing substantially from claim and equivalency range, the present invention does not limit
In specific details with shown here as the embodiment with description.
Claims (5)
1. an imperial folic acid, its structural formula is as follows:
2. the extracting method of dragon folic acid as claimed in claim 1, it is characterised in that comprise the following steps:
1) with dragon leaf coarse powder as raw material, ethanol is solvent, uses percolation to extract, obtains first after ethanol evaporation solvent
Extractum；
2) add water in described first extractum, form suspension, in suspension, then add petroleum ether, ethyl acetate extraction,
Obtain extract, the alcohol solvent in evaporative removal extract, obtain the second extractum；
3) take described second extractum, with chloroform and methanol as eluant, carry out gradient elution, then be 60～90:1 by volume ratio
Chloroform-methanol flow point, obtains white powder, is target product dragon folic acid.
3. the extracting method of dragon folic acid as claimed in claim 2, it is characterised in that step 1) in, the volume fraction of ethanol
Being 60～80%, the usage amount of described alcohol solvent is 8～12 times of dragon leaf coarse powder weight.
4. the extracting method of dragon folic acid as claimed in claim 2, it is characterised in that described step 2) in, in suspension
Add petroleum ether extraction extraction temperature be 60～90 DEG C.
5. the extracting method of dragon folic acid as claimed in claim 2, it is characterised in that described step 3) in, with chloroform and first
Alcohol is eluant, carries out gradient elution, is specifically divided into 12 gradients and carries out eluting, and chloroform is respectively as follows: with the volume ratio of methanol
100:0,70～90:1,40～60:1,20～40:1,10～30:1,5～15:1,6～10:1,4～7:1,1～5:1,1～3:
1,0.5～2:1,0:100.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110251552A (en) * | 2019-06-19 | 2019-09-20 | 苏州大学 | A kind of preparation method of Folium Sauropi general flavone |
-
2016
- 2016-03-30 CN CN201610190328.3A patent/CN105837651B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| 丘琴等: "龙脷叶乙酸乙酯、正丁醇部位化学成分研究", 《中药材》 * |
| 黄燕等: "龙脷叶提取物体外抑菌活性初步研究", 《大众科技》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110251552A (en) * | 2019-06-19 | 2019-09-20 | 苏州大学 | A kind of preparation method of Folium Sauropi general flavone |
| CN110251552B (en) * | 2019-06-19 | 2021-06-15 | 苏州大学 | Preparation method of total flavonoids of sauropus spatulifolius |
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