CN106565444B - The extracting method and application of Chinese yam aerial part phenanthrene class compound - Google Patents
The extracting method and application of Chinese yam aerial part phenanthrene class compound Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/36—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/34—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having three rings
Abstract
The invention discloses the extracting methods and application of a kind of Chinese yam aerial part phenanthrene class compound, belong to separation and the applied technical field of Chinese yam aerial part effective component.Technical solution of the present invention main points are as follows: Chinese yam aerial part coarse powder ethanol percolation is extracted and is concentrated, and extract is extracted with organic solvent, then obtains luxuriant and rich with fragrance class compound through column chromatography for separation such as macroporous absorbent resin, silica gel, glucan sugar gels.Four kinds of luxuriant and rich with fragrance class compounds that Chinese yam aerial part of the invention extracts have significant inhibitory activity to a- glucuroide, are better than the activity of hypoglycemic agent acarbose under the same conditions.
Description
Technical field
The invention belongs to the separation of Chinese yam aerial part effective component and applied technical fields, and in particular to a kind of Chinese yam
The extracting method and application of upper part phenanthrene class compound.
Background technique
Due to the raising of living standards of the people, the change of dietary structure and much few more dynamic life styles sat etc. it is many because
Element, global diabetes morbidity rapid development, diabetes have become the third-largest after tumour, cardiovascular pathological changes seriously threaten
The chronic disease of human health.The symptom occurred at first in the pathogenic process of diabetes is often postprandial hyperglycemia, i.e. diabetes
Early stage sign, especially Patients with NIDDM, postprandial hyperglycemia not only easily induce various complication, can also greatly mention
The death rate of high diabetes.So reducing postprandial blood sugar is prevention diabetes, reduces complication and reduce the important of the death rate and arrange
One of apply.Alpha-glucosidase is a kind of key enzyme of carbohydrate digestion process, it can become polysaccharide or disaccharides hydrolysis
Can be for the monosaccharide of absorption of human body, therefore inhibit active point that can delay carbohydrate in food of alpha-glucosidase
Solution reaches to reduce the intake of glucose and inhibits the raised purpose of postprandial blood sugar.Such drug clinically has Ah card at present
Wave sugar, voglibose and Miglitol.Existing alpha-glucosidase restrainer type is less, and with enteron aisle side effect,
Therefore people are still constantly dedicated to developing novel alpha-glucosidase restrainer.
Chinese yam (Disocorea oppositaThunb. it is) dry rhizome of Dioscoreaceae Chinese yam, there is tonifying spleen to support lung, Gu
The effect of kidney strengthening the essence, is clinically widely used in the symptoms such as treatment diabetes, chronic diarrhea and cough due to consumptive disease, is the traditional medicine in China
One of homologous Chinese medicine is eaten, tunnel the most is produced with Henan Jiaozuo (mansion Gu Huaiqing) from ancient times, therefore claims " RHIIZOMA DIOSCOREAE from Henan of China ", is famous " four
One of Huai medicine ".Henan Province in 2006, the planting base granted Chinese yam GAP, Wuzhi County, solves wild yam shortage of resources, resource
The problems such as sustainable use develops.Chinese yam is used as medicine with underground rhizome, and aerial part leads to resource frequently as waste abandoned
Significant wastage.The research of underground rhizome (medicinal part) is focused primarily upon for the research of Chinese yam at present, pharmacological research shows it
With hypoglycemic, reducing blood lipid, anti-oxidant and antitumor isoreactivity.However it is considerably less for the research of Chinese yam aerial part, it has no
It is reported in the research of hypoglycemic aspect.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of extracting method of Chinese yam aerial part phenanthrene class compound and answer
With.
The present invention adopts the following technical scheme that solve above-mentioned technical problem, the extraction of Chinese yam aerial part phenanthrene class compound
Method, it is characterised in that specific steps are as follows:
(1) it after crushing the Chinese yam aerial part to dry in the shade, is extracted, is merged with the ethanol percolation that volume fraction is 90%-95%
Extracting solution is concentrated under reduced pressure to give Chinese yam aerial part ethanol extract, then the ethanol extract is suspended in distilled water, successively
It is extracted with petroleum ether and ethyl acetate, collect acetic acid ethyl acetate extract and is concentrated under reduced pressure to give acetic acid ethyl ester extract, by acetic acid
Ethyl ester extract is through macroporous adsorbent resin column chromatography, ethyl alcohol that the ethyl alcohol for being successively 60% with volume fraction, volume fraction are 80%
The ethanol elution for being 95% with volume fraction, the ethyl alcohol that the ethanol eluate and volume fraction that collected volume score is 80% are 95%
Eluent is concentrated under reduced pressure to give 80% ethanol elution product and 95% ethanol elution product respectively；
(2) by 80% ethanol elution product through normal pressure silica gel column chromatography, it is in volume ratio with petroleum ether-acetone solvent system
In the range of 5:1-1:1 and methylene chloride-methanol solvent system volume ratio be 2:1-1:1 in the range of gradient elution, warp
TLC identification merges same composition and obtains initial target component, by initial target component through normal pressure silica gel column chromatography, with two
Chloromethanes-acetone solvent system gradient elution in the range of volume ratio is 50:1-10:1 respectively obtains compound 1, changes
Object 4 and intermediate objective component are closed, then intermediate objective component is recrystallized to give compound 2, wherein the structural formula of compound 1 is, the structural formula of compound 2 is, the knot of compound 4
Structure formula is；
(3) by 95% ethanol elution product through normal pressure silica gel column chromatography, it is in volume ratio with petroleum ether-acetone solvent system
In the range of 5:1-1:1 and methylene chloride-methanol solvent system volume ratio be 2:1-1:1 in the range of gradient elution, through TLC
Identification merges same composition and obtains initial target component, by initial target component through normal pressure silica gel column chromatography, with methylene chloride-the third
Solvent system gradient elution in the range of volume ratio is 100:0-20:1 identifies that merging same composition obtains centre through TLC
Target components, intermediate objective group lease making dextran gel column chromatography and half preparation HPLC purify to obtain compound 3, the compound 3
Structural formula be, wherein the eluent of dextran gel column chromatography is methanol, and half prepares
The mobile phase of HPLC is the methanol-water mixed solution of volume ratio 75:25.
Further preferably, the macroporous absorbent resin is Diaion HP-20 type macroporous absorbent resin, sephadex
For Sephadex LH-20 type sephadex.
The Chinese yam aerial part phenanthrene class compound extracted according to the above method is in preparing hypoglycemic drug or health care product
Using.
Alpha-glucosidase inhibitor medicine is being prepared according to the Chinese yam aerial part phenanthrene class compound that the above method extracts
Application in object or health care product.
The compound 4 extracted according to the above method is preparing answering in alpha-glucosidase inhibitor medicine or health care product
With.
The present invention studies four kinds of luxuriant and rich with fragrance classes that discovery Chinese yam aerial part extracts by external alpha-glucosaccharase enzyme inhibition activity
Compound has significant inhibiting effect, IC to alpha-glucosidase50Respectively 3.04 ± 0.25mM, 0.49 ± 0.034mM,
4.13 ± 0.023mM and 0.07 ± 0.0031mM, hence it is evident that be better than the activity (IC of positive control drug acarbose50For 61.57 ±
It 1.40mM), and to the inhibiting rate of alpha-glucosidase is in dose dependent.
Detailed description of the invention
Fig. 1 is change curve of the compound 1 of the extraction of embodiment 1 to alpha-glucosaccharase enzyme inhibition rate with drug concentration；
Fig. 2 is change curve of the compound 2 of the extraction of embodiment 2 to alpha-glucosaccharase enzyme inhibition rate with drug concentration；
Fig. 3 is change curve of the compound 3 of the extraction of embodiment 3 to alpha-glucosaccharase enzyme inhibition rate with drug concentration；
Fig. 4 is change curve of the compound 4 of the extraction of embodiment 1 to alpha-glucosaccharase enzyme inhibition rate with drug concentration.
Specific embodiment
Above content of the invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on above content of the present invention belong to this hair
Bright range.
Embodiment 1
The Chinese yam aerial part 8.5kg to dry in the shade after crushing, is extracted with the ethanol percolation that volume fraction is 95%, is merged and extract
Liquid is concentrated under reduced pressure to obtain total medicinal extract 871.5g, medicinal extract is suspended in 2 times of amount water, the petroleum ether and ethyl acetate successively measured with 5 times
Extraction is collected acetic acid ethyl acetate extract and is concentrated under reduced pressure, obtains acetic acid ethyl ester extract 100.2g.Acetic acid ethyl ester extract is passed through
Diaion HP-20 type macroporous adsorbent resin column chromatography, the second that the ethyl alcohol and volume fraction for being successively 60% with volume fraction are 80%
Alcohol elution, ethanol eluate and reduced pressure of the collected volume score for 80%, obtains 80% ethanol elution product 45.7g.80% second
Alcohol eluted product is through normal pressure silica gel column chromatography, with petroleum ether-acetone (volume ratio is respectively 5:1,3:1,2:1 and 1:1) and dichloro
The elution of methane-methanol (volume ratio is respectively 2:1 and 1:1) solvent system identifies that merging same composition obtains 10 components through TLC
(Fr.1-Fr.10).Fr.4 is through normal pressure silica gel column chromatography, and with dichloromethane-acetone, (volume ratio is respectively 50:1,30:1,20:1
And 10:1) solvent system elution, respectively obtain compound 1(2.6mg) and compound 4(2.1mg).
The spectral data of compound 1 and 4:7-hydroxy-2,6-dimethoxy-1,4-phenanthrenedione
(1): Red amorphous powder, ESI-MSm/z307 [M+Na]+。1H-NMR (400 MHz, DMSO-d 6) δ: 10.35
(1H, s, 7-OH), 9.01 (1H, s, H-5), 8.03 (1H, d, J = 8.5 Hz, H-10), 7.87 (1H,
d, J = 8.5 Hz, H-9), 7.26 (1H, s, H-8), 6.24 (1H, s, H-3), 3.96 (3H, s, 6-
OCH3), 3.86 (3H, s, 2-OCH3); 13C-NMR (400 MHz, DMSO-d 6) δ: 188.6 (C-4), 180.5
(C-1), 158.4 (C-2), 152.5 (C-6), 149.6 (C-7), 134.4 (C-8a), 131.7 (C-9),
128.7 (C-10a), 124.9 (C-4b), 124.8 (C-4a), 120.0 (C-10), 111.3 (C-3), 110.3
(C-8), 106.1 (C-5), 56.4 (2-OCH3), 55.5 (6-OCH3)。
volucrin(4): faint yellow amorphous powder, HRESI-MSm/z 561.1520 [M+Na]+ (calcd
for C32H26O8Na, 561.1525。1H-NMR (400 MHz, acetone-d 6) δ: 9.28 (2H, s, H-5, 5'),
7.29 (2H, d, J = 9.1 Hz, H-10, 10'), 6.99 (2H, d, J = 9.1 Hz, H-9, 9'), 6.92
(2H, d, J = 2.5 Hz, H-1, 1'), 6.81 (2H, d, J = 2.5 Hz, H-3, 3'), 4.16 (6H, s,
4,4¢-OCH3), 3.90 (6H, s, 2,2¢-OCH3)。
Embodiment 2
The Chinese yam aerial part 8.5kg to dry in the shade after crushing, is extracted with the ethanol percolation that volume fraction is 95%, is merged and extract
Liquid is concentrated under reduced pressure to obtain total medicinal extract 871.5g, medicinal extract is suspended in 2 times of amount water, the petroleum ether and ethyl acetate successively measured with 5 times
Extraction is collected acetic acid ethyl acetate extract and is concentrated under reduced pressure, obtains acetic acid ethyl ester extract 100.2g.Acetic acid ethyl ester extract is passed through
Diaion HP-20 type macroporous adsorbent resin column chromatography, the second that the ethyl alcohol and volume fraction for being successively 60% with volume fraction are 80%
Alcohol elution, ethanol eluate and reduced pressure of the collected volume score for 80%, obtains 80% ethanol elution product 45.7g.80% second
Alcohol eluted product is through normal pressure silica gel column chromatography, with petroleum ether-acetone (volume ratio is respectively 5:1,3:1,2:1 and 1:1) and dichloro
The elution of methane-methanol (volume ratio is respectively 2:1 and 1:1) solvent system identifies that merging same composition obtains 10 components through TLC
(Fr.1-Fr.10).Fr.8 is recrystallized to give compound 2(7.0mg).
The spectral data of compound 2:6,7-dihydroxy-2-methoxy-1,4-phenanthrenedione(2):
Red amorphous powder, ESI-MSm/z 293 [M+Na]+。1H-NMR (400 MHz, DMSO-d 6) δ: 8.93 (1H,
s, H-5), 7.95 (1H, d, J = 8.4Hz, H-9), 7.78 (1H, d, J = 8.4Hz, H-10), 7.20
(1H, s, H-8), 6.21 (1H, s, H-3), 3.84 (3H, s, 2-OCH3)。
Embodiment 3
The Chinese yam aerial part 8.5kg to dry in the shade after crushing, is extracted with the ethanol percolation that volume fraction is 95%, is merged and extract
Liquid is concentrated under reduced pressure to obtain total medicinal extract 871.5g, medicinal extract is suspended in 2 times of amount water, the petroleum ether and ethyl acetate successively measured with 5 times
Extraction is collected acetic acid ethyl acetate extract and is concentrated under reduced pressure, obtains acetic acid ethyl ester extract 100.2g.Acetic acid ethyl ester extract is passed through
Diaion HP-20 type macroporous adsorbent resin column chromatography, the second that the ethyl alcohol and volume fraction for being successively 80% with volume fraction are 95%
Alcohol elution, ethanol eluate and reduced pressure of the collected volume score for 95%, obtains 95% ethanol elution product 25.0g.95% second
Alcohol eluted product is through normal pressure silica gel column chromatography, with petroleum ether-acetone (volume ratio is respectively 5:1,3:1,2:1 and 1:1) and dichloro
The elution of methane-methanol (volume ratio is respectively 2:1 and 1:1) solvent system identifies that merging same composition obtains 7 components through TLC
(Fr.1-Fr.7).Fr.2 through normal pressure silica gel column chromatography, with dichloromethane-acetone (volume ratio is respectively 100:0,50:1 and 20:
1) solvent system elutes, and identifies that merging same composition obtains 6 components (Fr.2.1-Fr.2.6), Fr.2.6 warp through TLC
Sephadex LH-20 dextran gel column chromatography (methanol elution) and half preparation HPLC(mobile phase: methanol-water, volume ratio 75:
25) purifying obtains compound 3(2.4mg).
The spectral data of compound 3:7-hydroxy-2,4,6-trimethoxyphenanthrene(3): white powder
End, ESI-MSm/z307 [M+Na]+。1H-NMR (400 MHz, acetone-d 6) δ: 9.04 (1H, s, H-5),
7.66 (1H, d, J = 8.8 Hz, H-9), 7.52 (1H, d, J = 8.8 Hz, H-10), 7.37 (1H, s,
H-8), 6.98 (1H, d, J = 2.5 Hz, H-1), 6.78 (1H, d, J = 2.5 Hz, H-3), 4.11 (3H,
s, 2-OCH3), 3.99 (3H, s, 6-OCH3), 3.92 (3H, s, 4-OCH3); 13C-NMR (100 MHz,
acetone-d 6) δ: 160.4 (C-2), 158.7 (C-4), 147.6 (C-6), 147.3 (C-7), 135.9 (C-
10a), 128.6 (C-9), 127.7 (C-4b), 126.5 (C-8a), 125.2 (C-10), 116.2 (C-4a),
113.5 (C-8), 109.2 (C-5), 102.2 (C-1), 99.7 (C-3), 56.1 (6, 4-OCH3), 55.7 (2-
OCH3)。
Embodiment 4
The present embodiment is that the compound 1-4 that above-described embodiment extracts tests the inhibitory activity of alpha-glucosidase.
Method: Microdilution plate method.
Instrument: microplate reader, constant incubator, assay balance, various model liquid-transfering guns.
Reagent: alpha-glucosidase, 4- nitrobenzene-α-D- glucopyranoside, acarbose, phosphate buffer and two
Methyl sulfoxide.
Test method: taking 96 orifice plates, and PNPG solution (PBS dissolution) 80 μ L of 2.0mmol/L are added in every hole, then are separately added into
10 μ L various concentration sample solutions (DMSO dissolution), using DMSO as blank control group, every group sets 3 parallel holes, in microplate reader
Background group absorbance (A value) is measured under 400nm.Then adding 10 μ L 1.62U/mL alpha-glucosaccharase enzyme solutions, (PBS is molten
Solution), it is placed in constant incubator, the constant-temperature incubation 30min at 37 DEG C, measures test group absorbance (A value).Inhibiting rate (%) is used
Following formula calculates:
Inhibiting rate (%)=(Δ ABlank-ΔASample)/ΔABlank×100%
ΔABlankFor A value-background A value after the reaction of blank group enzyme-to-substrate；
ΔASampleFor A value-background A value after the reaction of sample sets enzyme-to-substrate.
Compound 1-4 is following (table 1) to the inhibitory activity result of alpha-glucosidase:
Inhibitory activity of the 1 compound 1-4 of table to alpha-glucosidase
| Compound | IC50(mM) |
| 1 | 3.04± 0.25 |
| 2 | 0.49± 0.034 |
| 3 | 4.13± 0.023 |
| 4 | 0.07± 0.0031 |
| Acarbose | 61.57±1.40 |
As it can be seen from table 1 the compound 1-4 that embodiment 1-3 is extracted is better than the inhibitory activity of alpha-glucosidase
The activity of positive control drug acarbose, wherein the activity of compound 4 is most strong, is much better than the work of positive control drug acarbose
Property.
Embodiment above describes basic principles and main features of the invention and advantage, the technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe originals of the invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (2)
1. the extracting method of Chinese yam aerial part phenanthrene class compound, it is characterised in that specific steps are as follows:
(1) it after crushing the Chinese yam aerial part to dry in the shade, is extracted with the ethanol percolation that volume fraction is 90%-95%, merges and extract
Liquid is concentrated under reduced pressure to give Chinese yam aerial part ethanol extract, then the ethanol extract is suspended in distilled water, successively uses stone
Oily ether and ethyl acetate extraction, collect acetic acid ethyl acetate extract and are concentrated under reduced pressure to give acetic acid ethyl ester extract, by ethyl acetate
Extract is through macroporous adsorbent resin column chromatography, ethyl alcohol and body that the ethyl alcohol for being successively 60% with volume fraction, volume fraction are 80%
The ethanol elution that fraction is 95%, the ethanol elution that the ethanol eluate and volume fraction that collected volume score is 80% are 95%
Liquid is concentrated under reduced pressure to give 80% ethanol elution product and 95% ethanol elution product respectively；
(2) in volume ratio it is 5:1-1 with petroleum ether-acetone solvent system by 80% ethanol elution product through normal pressure silica gel column chromatography:
In the range of 1 and methylene chloride-methanol solvent system volume ratio be 2:1-1:1 in the range of gradient elution, reflect through TLC
Surely merge same composition and obtain initial target component, by initial target component through normal pressure silica gel column chromatography, use dichloro
Methane-acetone solvent system gradient elution in the range of volume ratio is 50:1-10:1 respectively obtains compound 1, chemical combination
Object 4 and intermediate objective component, then intermediate objective component is recrystallized to give compound 2, wherein the structural formula of compound 1 is, the structural formula of compound 2 is, the structure of compound 4
Formula is；
It (3) in volume ratio is 5:1- with petroleum ether-acetone solvent system by 95% ethanol elution product through normal pressure silica gel column chromatography
In the range of 1:1 and methylene chloride-methanol solvent system volume ratio be 2:1-1:1 in the range of gradient elution, identified through TLC
Merge same composition and obtains initial target component, it is molten with dichloromethane-acetone by initial target component through normal pressure silica gel column chromatography
Agent system gradient elution in the range of volume ratio is 100:0-20:1 identifies that merging same composition obtains intermediate objective through TLC
Component, intermediate objective group lease making dextran gel column chromatography and half preparation HPLC purify to obtain compound 3, the knot of the compound 3
Structure formula is, wherein the eluent of dextran gel column chromatography is methanol, and half prepares HPLC
Mobile phase be volume ratio 75:25 methanol-water mixed solution.
2. the extracting method of Chinese yam aerial part phenanthrene class compound according to claim 1, it is characterised in that: described is big
Macroporous adsorbent resin is Diaion HP-20 type macroporous absorbent resin, and sephadex is solidifying for Sephadex LH-20 type glucan
Glue.
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| a-Glucosidase inhibitors from Chinese Yam (Dioscorea opposita Thunb.);Lin Zhang等;《Food Chemistry》;20111231(第126期);第203-206页 |
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