CN105949266B - Withanolide class compound and extracting method and application - Google Patents
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Abstract
The invention discloses withanolide class compound and extracting method and application, withanolide class compound has formula (I) structure：
Description
Technical field
The present invention relates to field of traditional Chinese medicine extraction, is related to a kind of withanolide class compound, extracting method and application.
Background technology
Bitter Zhi (Physalis angulata L.), also known as Chinese lantern, little groundcherry herb or fruit, Herba seu Fructus Physalis Minimae, Piao Piaocao, beat volume bubble etc.,
For Solanaceae (Solanaceae) Physalis (Physalis) annual herb plant.《Luchuan book on Chinese herbal medicine》With《Chinese book on Chinese herbal medicine》Dui Ku Zhi
Medicinal efficacy have detailed record, bitter Zhi has promoting the circulation of qi, dissipate-swelling, diuresis, controls abdominal distension, clearing heat and detoxicating, diuresis hemostasis, detumescence
Dissipating bind, available for treating abscess of throat, lung carbuncle, parotitis；The diseases such as difficult urination, blood urine swelling and aching of gum, pemphigus.It is among the people more
For treating the diseases such as blister sore, swelling and aching of gum, jaundice with damp-heat pathogen, red swelling and pain of throat, cough with lung heat.Domestic and foreign scholars pass through body
Interior, experiment in vitro confirms Ku Zhi anti-inflammatory (Choi, E.M.；et al.Investigations of anti-
inflammatory and antinociceptive activities of Piper cubeba,Physalis angulata
And Rosa hybrida.Journal of Ethnopharmacology 2003,89,171-175.), antitumor (He, H.；
et al.Physalin A induces apoptotic cell death and protective autophagy in
HT1080human fibrosarcoma cells.Journal of Natural Products,2013,76,880–888.)、
Antibacterial (Silva, M.T.G.；et al.Studies on antimicrobial activity,in vitro,of
Physalis angulata L.(Solanaceae)fraction and physalin B bringing out the
importance of assay determination.Memorias do Instituto Oswaldo Cruz 2005,
100,779-782.), anti-oxidant (Choi, E.M.；et al.Effect of some medicinal plants on
plasma antioxidant system and lipid levels in rats.Phytotherapy
The effect such as research.2005,19,382-386.).
But withanolide class compound, extracting method and application are extracted in Cong Ku Zhi, and there is not been reported.
The content of the invention
It is an object of the invention to provide withanolide class compound.
Second object of the present invention is to provide the extracting method of withanolide class compound.
Third object of the present invention is to provide the application of withanolide class compound.
Fourth object of the present invention is to provide the withanolide class compound Ku Zhi extractions comprising claim 1 and 2
Thing.
The 5th purpose of the present invention is to provide the application of Ku Zhi extracts.
The 6th purpose of the present invention is to provide the pharmaceutical composition of the compound of class containing withanolide.
The 7th purpose of the present invention is to provide the application of aforementioned pharmaceutical compositions.
Technical scheme is summarized as follows：
Withanolide class compound, there is the structure of formula (I)：
Wherein：
R1For OH or OCH3；
R2For OH or H；
R3For OH or OAc；
R4For H；R5For H or OH；Or R4And R5For
R6For H or OH.
Above-claimed cpd, preferable structural formula are：
The extracting method of above-claimed cpd, comprises the following steps：
(for 1) using Ku Zhi drying cauline leaf as raw material, the volume fraction for adding raw material 8-10 mass times is 60%-80% ethanol
The aqueous solution, refluxing extraction 2-3 times, extract every time 2-3 hours, merging obtains extract solution, and solvent is recovered under reduced pressure, and is obtained after concentration total
Medicinal extract；
(2) total medicinal extract is distributed in the water of 5-10 mass times, extracted successively with petroleum ether and ethyl acetate, acetic acid
Solvent is recovered under reduced pressure in ethyl ester extract, obtains ethyl acetate layer medicinal extract；
(3) ethyl acetate layer medicinal extract separates through silica gel column chromatography, is respectively 100 with volume ratio:1、50:1、30:1 and 15:1
Methylene chloride-methanol be eluent gradient elution, obtain cut Fr.1, Fr.2, Fr.3 and Fr.4；
(4) cut Fr.3 separates through silica gel column chromatography, is respectively 10 with volume ratio:1、8:1 and 6:1 petroleum ether-acetone
Eluted for eluent gradient, obtain cut Fr.3-1, Fr.3-2, Fr.3-3；
(5) cut Fr.3-3 is through Sephadex LH-20 pillar layer separations, using volume ratio as 1:1 methylene chloride-methanol
For eluant, eluent isocratic elution, cut Fr.3-3-1 and Fr.3-3-2 are obtained；
(6) cut Fr.3-3-2 is through ODS pillar layer separations, using volume ratio as 1:9、3:7、5:5 and 8:2 methanol-water is
Eluent gradient elutes, and obtains cut Fr.3-3-2-1, Fr.3-3-2-2, Fr.3-3-2-3 and Fr.3-3-2-4；
(7) cut Fr.3-3-2-4 separates through silica gel preparative thin layer chromatography, using volume ratio as 1:1 dichloromethane-acetone
Prepared for solvent, obtain compound 2；
(8) cut Fr.4 separates through silica gel column chromatography, using volume ratio as 80:1、40:1、20:1、10:1 and 5:1 chlorine
Imitative-acetone elutes for eluent gradient, obtains cut Fr.4-1, Fr.4-2, Fr.4-3, Fr.4-4 and Fr.4-5；
(9) cut Fr.4-2 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is purified,
Obtain compound 4；
(10) cut Fr.4-4 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is purified,
Obtain compound 5；
(11) cut Fr.4-5 is through ODS pillar layer separations, using volume ratio as 7:3 methanol-water is mobile phase, is carried out pure
Change, obtain cut Fr.4-5-1, Fr.4-5-2；
(12) cut Fr.4-5-2 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is carried out pure
Change, obtain compound 1 and compound 3.
Withanolide class compound is preparing the application in suppressing cell release NO medicines.
Include withanolide class Ku Zhi extracts.
Ku Zhi extracts are preparing the application in suppressing cell release NO medicines.
A kind of pharmaceutical composition, it is to include withanolide class compound or its pharmaceutically acceptable salt, and pharmaceutically may be used
The carrier and/or excipient of receiving.
Aforementioned pharmaceutical compositions are preparing the application in suppressing cell release NO medicines.
Advantages of the present invention：
The withanolide class compound of the present invention can effectively suppress nitric oxide (NO) release, prompt chemical combination of the present invention
Thing can be as the medicine of anti-inflammatory.
Embodiment
Technical scheme is described below in conjunction with specific embodiment, described embodiment is only this
Invention part of the embodiment, rather than whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art exist
The every other embodiment obtained under the premise of creative work is not made, belongs to the scope of protection of the invention.
Embodiment 1
The extracting method of withanolide class compound, comprises the following steps：
(1) Yi Ku Zhi (Physalis angulata L.) drying cauline leaf (9.5kg) is raw material, adds the mass of raw material 9
Volume fraction again is 75% ethanol water, and refluxing extraction 2 times, extraction 2 hours, merge and obtain extract solution, depressurize back every time
Solvent is received, total medicinal extract (1370g) is obtained after concentration；
(2) total medicinal extract is distributed in the water of 5 mass times, extracted successively with isometric petroleum ether and ethyl acetate,
Solvent is recovered under reduced pressure in acetic acid ethyl acetate extract, obtains ethyl acetate layer medicinal extract 116g；
(3) ethyl acetate layer medicinal extract separates through silica gel column chromatography, is respectively 100 with volume ratio:1、50:1、30:1 and 15:1
Methylene chloride-methanol be eluent gradient elution, obtain cut Fr.1, Fr.2, Fr.3 (35g) and Fr.4 (15g)；
(4) cut Fr.3 separates through silica gel column chromatography, is respectively 10 with volume ratio:1、8:1 and 6:1 petroleum ether-acetone
Eluted for eluent gradient, obtain cut Fr.3-1, Fr.3-2, Fr.3-3 (4.2g)；
(5) cut Fr.3-3 is through Sephadex LH-20 pillar layer separations, using volume ratio as 1:1 methylene chloride-methanol
For eluant, eluent isocratic elution, cut Fr.3-3-1 and Fr.3-3-2 (600mg) are obtained；
(6) cut Fr.3-3-2 is through ODS pillar layer separations, using volume ratio as 1:9、3:7、5:5 and 8:2 methanol-water is
Eluent gradient elutes, and obtains cut Fr.3-3-2-1, Fr.3-3-2-2, Fr.3-3-2-3 and Fr.3-3-2-4 (500mg)；
(7) cut Fr.3-3-2-4 separates through silica gel preparative thin layer chromatography, using volume ratio as 1:1 dichloromethane-acetone
Prepared for solvent, obtain compound 2 (8mg)；
(8) cut Fr.4 separates through silica gel column chromatography, using volume ratio as 80:1、40:1、20:1、10:1 and 5:1 chlorine
Imitative-acetone elutes for eluent gradient, obtains cut Fr.4-1, Fr.4-2 (2g), Fr.4-3, Fr.4-4 (1.5g) and Fr.4-
5(1.7g)；
(9) cut Fr.4-2 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is purified,
Obtain compound 4 (19mg)；
(10) cut Fr.4-4 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is purified,
Obtain compound 5 (4mg)；
(11) cut Fr.4-5 is through ODS pillar layer separations, using volume ratio as 7:3 methanol-water is mobile phase, is carried out pure
Change, obtain cut Fr.4-5-1, Fr.4-5-2 (800mg)；
(12) cut Fr.4-5-2 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is carried out pure
Change, obtain compound 1 (19mg) and compound 3 (6mg).
The physical chemistry and constant of each compound are as follows：
Compound 1：Unformed powder；UV(MeOH)λmax(logε)218(4.0)
nm；IR(KBr)νmax3396,2921,2851,1740,1711,1683,1647,1467,1384,1229cm-1；CD(MeOH)nm
(Δ ε) 254 (+1.7), 329 (- 0.9)；HRESIME m/z 581.2727[M+Na]+(calcd for C31H42O9Na,
581.2727) molecular formula for, determining compound 1 is C31H42O9；1H (400MHz, pyridine-d5) and13C-NMR (100MHz,
pyridine-d5) data are shown in Table 1 and 2.
Compound 2：Unformed powder；UV(MeOH)λmax(logε)226(3.7)
nm；IRνmax(KBr) 3395,2920,2849,1646,1469,1384,1121cm-1；CD (MeOH) nm (Δ ε) 255 (+1.5),
331(-0.1)；HRESIME m/z 583.2885[M+Na]+(calcd for C31H44O9Na, 583.2883), determine compound
2 molecular formula is C30H40O8；1H (400MHz, pyridine-d5) and13C-NMR (100MHz, pyridine-d5) data are shown in Table 1
With 2.
Compound 3：Unformed powder；UV(MeOH)λmax(logε)218(3.9)
nm；IR(KBr)νmax3398,2920,2850,1760,1655,1467,1385,1133cm-1；CD(MeOH)nm(Δε)252(+
1.7), 333 (- 1.0)；HRESIME m/z 525.2461[M+Na]+(calcd for C28H38O8Na, 525.2464), it is determined that
The molecular formula of compound 3 is C28H38O8；1H (400MHz, pyridine-d5) and13C-NMR (100MHz, pyridine-d5) number
According to being shown in Table 1 and 2.
Compound 4：Unformed powderUV(MeOH)λmax(logε)216(4.2)
nm；IR(KBr)νmax3398,2921,2850,1681,1647,1467,1384,1129cm-1；CD(MeOH)nm(Δε)252(+
4.0), 332 (- 1.9)；HRESIME m/z 537.2830[M+Na]+(calcd for C30H42O7Na, 537.2828), it is determined that
The molecular formula of compound 4 is C30H42O7；1H (400MHz, pyridine-d5) and13C-NMR (100MHz, pyridine-d5) number
According to being shown in Table 1 and 2.
Compound 5：Unformed powder；UV(MeOH)λmax(logε)224(3.7)
nm；
UV(MeOH)λmax(logε)224(4.0)nm；IR(KBr)νmax3395,2921,2850,1760,1647,1467,
1384,1133cm-1；CD (MeOH) nm (Δ ε) 256 (+1.4), 333 (- 0.4)；HRESIME m/z 511.2671
[M+Na]+(calcd for C28H40O7Na, 511.2672), the molecular formula for determining compound 5 is C30H40O8；1H (400MHz,
pyridine-d5) and13C-NMR (100MHz, pyridine-d5) data are shown in Table 1 and 2.
The compound 1-5 hydrogen modal datas of table 1
Note：A, 400MHz, pyridine-d5。
The compound 1-5 of table 2 carbon modal data
Note：A, 400MHz, pyridine-d5。
The structure of each compound is：
Embodiment 2
The extracting method of withanolide class compound, comprises the following steps：
(for 1) using Ku Zhi drying cauline leaf as raw material, the volume fraction for adding the mass times of raw material 8 is 80% ethanol water,
Refluxing extraction 3 times, every time extraction 2 hours, merging obtain extract solution, solvent are recovered under reduced pressure, total medicinal extract is obtained after concentration；
(2) total medicinal extract is distributed in the water of 5 mass times, extracted successively with isometric petroleum ether and ethyl acetate,
Solvent is recovered under reduced pressure in acetic acid ethyl acetate extract, obtains ethyl acetate layer medicinal extract；
(3)-(12) are the same as embodiment 1 (3)-(12).
Embodiment 3
The extracting method of withanolide class compound, comprises the following steps：
(for 1) using Ku Zhi drying cauline leaf as raw material, the volume fraction for adding the mass times of raw material 10 is 60% ethanol water,
Refluxing extraction 3 times, every time extraction 2 hours, merging obtain extract solution, solvent are recovered under reduced pressure, total medicinal extract is obtained after concentration；
(2) total medicinal extract is distributed in the water of 10 mass times, extracted successively with isometric petroleum ether and ethyl acetate,
Solvent is recovered under reduced pressure in acetic acid ethyl acetate extract, obtains ethyl acetate layer medicinal extract；
(3)-(12) are the same as embodiment 1 (3)-(12).
Embodiment 4
The active testing that withanolide class compound suppresses the release nitric oxides of mouse macrophage RAW 264.7 (NO) is small
Mouse macrophage RAW 264.7 (ATCC) be incubated at 10% heat inactivation (56 DEG C, 30min) hyclone (Gibco, USA),
RPMI 1640 (Gibco, the USA) trainings of 100U/mL Benzylpenicillin sodium salts (Gibco, USA), 100 μ g/mL streptomysins (Gibco, USA)
In nutrient solution, 37 DEG C, 5%CO2Constant incubator in be incubated growth.Because NO is extremely unstable, in cell culture supernatant very
Nitrito- (NO is metabolized to soon2 -), therefore use NO in Griess method determination samples2 -The concentration index horizontal as NO is weighed.
Griess reagent As：0.1%N- naphthodiamides hydrochloride (naphthylethylene diamine dihydrochloride) is molten
Yu Shuizhong；Griess reagents B：1% P-aminobenzene-sulfonamide (sulphanilamide) is dissolved in 5%H3PO4In.Body is waited using preceding
Product mix reagent A and B.The cells of RAW 264.7 are diluted to 5 × 10 with RPMI 1640 culture mediums5Cells/mL concentration, inoculation
In 96 porocyte culture plates, 200100 μ L cell suspending liquids are added per hole.CO2After cultivating 1h in incubator, fat is added per hole
The survey of polysaccharide (lipopolysaccharide, LPS) (Sigma, JPN) (the μ g/mL of final concentration 1) and the various concentrations of DMSO dissolvings
0%) and blank the μ L of test agent 0.4, while set LPS groups and (add LPS, but be added without test sample, to the inhibiting rates of NO releases for
Control group (is added without LPS and test sample, only adds 0.4 μ L DMSO, the inhibiting rate to NO releases is 100%) each sample
If 4 parallel holes.At 37 DEG C, 5%CO2Constant incubator in cultivate 24h, draw 100 μ L nutrient solution supernatants into ELISA Plate,
Centrifugation (1000 × g, 4 DEG C, 3min), 100 μ L Griess reagents are added, room temperature lucifuge reaction 10min, it are determined in ELIASA
Light absorption value at 540nm.It is respectively 1,5,10,50 μm of ol/L NaNO with concentration2Standard curve is drawn, according to NaNO2Standard curve
NO in cell culture supernatant2 -Concentration so that calculate the inhibiting rate that is discharged to NO of test sample.
The suppression NO releasing results of the compound of table 3
The anti-inflammatory drug of composition containing compound of the present invention can be to apply shape suitable for oral or injection etc.
Formula, for example, routinely technology, adds pharmaceutically acceptable carrier and/or excipient and tablet, capsule, pulvis, syrup is made
Agent, injection etc..
Compound has pharmacological activity, and therefore, the composition containing the compound also has pharmacological activity.
The explanation of above example is only intended to help the method and its central idea for understanding the present invention.It should be pointed out that pair
For one of ordinary skill in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out some
Improve and modify, these are improved and modification also falls into the protection of the claims in the present invention.
The withanolide class compound of the present invention, extract, the chemical combination of class containing withanolide of the compound of class containing withanolide
The composition of thing can prepare the medicine for the treatment of metabolism of nitric oxide exception associated diseases.
Its associated disease includes：Systemic inflammatory response syndrome, hypertension, cerebral thrombus, heart failure, hepatic sclerosis,
Rheumatoid arthritis, osteoarthritis, joint of vertebral column inflammation, inflammatory bowel disease, acute pancreatitis, peritonitis, cholecystitis, appendicitis,
Diabetes, systemic loupus erythematosus, dermatitis flesh, psoriasis, acute myeloid leukaemia, parkinsonism, alzheimer's disease, depression
Disease, septicemia, chronic obstructive pneumonia, asthma, acute pancreatitis, central nervous system injury etc..Secondly, NO metabolic disorders also with cancer
Become and the hyperplasia of cancerous tissue be relevant, the NO of high concentration also can modificator gene mutation and tumour, above-claimed cpd, which can suppress NO, to be released
Put, so as to play antineoplastic action.Applicable tumour example includes but is not limited to：Various entity tumors and leukaemia, such as lung
Cancer, liver cancer, cancer of pancreas, stomach cancer, osteocarcinoma, cancer of the esophagus, prostate cancer, colon cancer, oophoroma, carcinoma of urinary bladder, cervix cancer, melanin
Knurl, carcinoma of testis, bronchiolar carcinoma, clear-cell carcinoma, cholangiocarcinoma, choriocarcinoma, spongiocytoma, neurofibroma, fibrosarcoma, leaching
Hand shaft knurl etc..
Claims (5)
1. withanolide class compound, it is characterized in that the structure with formula (1) or formula (2)：
2. the extracting method of compound described in claim 1, it is characterised in that comprise the following steps：
(1) using bitter Zhi drying cauline leaf as raw material, the volume fraction for adding raw material 8-10 mass times is water-soluble for 60%-80% ethanol
Liquid, refluxing extraction 2-3 times, extract every time 2-3 hours, merging obtains extract solution, and solvent is recovered under reduced pressure, is always soaked after concentration
Cream；
(2) total medicinal extract is distributed in the water of 5-10 mass times, extracted successively with petroleum ether and ethyl acetate, ethyl acetate
Solvent is recovered under reduced pressure in extract, obtains ethyl acetate layer medicinal extract；
(3) ethyl acetate layer medicinal extract separates through silica gel column chromatography, is respectively 100 with volume ratio:1、50:1、30:1 and 15:The two of 1
Chloromethanes-methanol elutes for eluent gradient, obtains cut Fr.1, Fr.2, Fr.3 and Fr.4；
(4) cut Fr.3 separates through silica gel column chromatography, is respectively 10 with volume ratio:1、8:1 and 6:1 petroleum ether-acetone is to wash
De- agent gradient elution, obtains cut Fr.3-1, Fr.3-2, Fr.3-3；
(5) cut Fr.3-3 is through Sephadex LH-20 pillar layer separations, using volume ratio as 1:1 methylene chloride-methanol is to wash
De- agent isocratic elution, obtains cut Fr.3-3-1 and Fr.3-3-2；
(6) cut Fr.3-3-2 is through ODS pillar layer separations, using volume ratio as 1:9、3:7、5:5 and 8:2 methanol-water is elution
Agent gradient elution, obtain cut Fr.3-3-2-1, Fr.3-3-2-2, Fr.3-3-2-3 and Fr.3-3-2-4；
(7) cut Fr.3-3-2-4 separates through silica gel preparative thin layer chromatography, using volume ratio as 1:1 dichloromethane-acetone is exhibition
Open agent to be prepared, obtain compound 2；
(8) cut Fr.4 separates through silica gel column chromatography, using volume ratio as 80:1、40:1、20:1、10:1 and 5:1 chloroform-the third
Ketone elutes for eluent gradient, obtains cut Fr.4-1, Fr.4-2, Fr.4-3, Fr.4-4 and Fr.4-5；
(9) cut Fr.4-5 is through ODS pillar layer separations, using volume ratio as 7:3 methanol-water is mobile phase, is purified, obtained
Cut Fr.4-5-1, Fr.4-5-2；
(10) cut Fr.4-5-2 is through preparing HPLC chromatogram, using volume ratio as 7:3 methanol-water is mobile phase, is purified, obtained
To compound 1.
3. claim 1 withanolide class compound is preparing the application in suppressing cell release NO medicines.
4. a kind of pharmaceutical composition, it is characterized in that the withanolide class compound comprising claim 1 or its is pharmaceutically acceptable
Salt, and pharmaceutically acceptable carrier and/or excipient.
5. the pharmaceutical composition of claim 4 is preparing the application in suppressing cell release NO medicines.
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| CN101422467A (en) * | 2007-11-02 | 2009-05-06 | 华东理工大学 | Immunosuppressant containing Withanolide type compound |
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| Title |
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| Withanolides from physalis minima and their inhibitory effects on nitric oxide production;Yu-Zhou Guan et al.;《 Steroids》;20140127;第38-43页 * |
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| CN105949266A (en) | 2016-09-21 |
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