CN109320409A - A kind of preparation method and applications with antimycotic and anti-tumor activity anthraquinone dimer class compound - Google Patents
A kind of preparation method and applications with antimycotic and anti-tumor activity anthraquinone dimer class compound Download PDFInfo
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- CN109320409A CN109320409A CN201811346035.5A CN201811346035A CN109320409A CN 109320409 A CN109320409 A CN 109320409A CN 201811346035 A CN201811346035 A CN 201811346035A CN 109320409 A CN109320409 A CN 109320409A
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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
- C07C50/36—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having four or more rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
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Abstract
The present invention relates to antimycotic and the anthraquinone dimer class compound of anti-tumor activity preparation method and applications, preparation, which can effectively be solved, has antimycotic and anti-tumor activity anthraquinone dimer class compound, the problem of realization prepares antimycotic and anti-tumor drug, its solve technical solution be, pass through anthraquinone dimer Solanrubiellin A isolated from bittersweet, external antimycotic and antitumor activity shows, anthraquinone dimer Solanrubiellin A of the invention is to a variety of pathomycetes, including staphylococcus aureus, staphylococcus epidermis and enterococcus faecalis significantly inhibit, simultaneously to adenocarcinoma of lung, colon cancer, cervical carcinoma, the kinds of tumors such as liver cancer and acute promyelocytic leukemic have apparent inhibitory activity, and it can conveniently be prepared into a variety of drugs Dosage form facilitates clinical use.
Description
Technical field
It is especially a kind of with antimycotic and anti-tumor activity anthraquinone dimer class chemical combination the present invention relates to field of medicaments
The preparation method and applications of object.
Background technique
Malignant tumour is to seriously endanger one of human health and the principal disease of life.Recently as living standard of urban and rural population
The multifactor impacts such as the change of habit and dietary structure, the disease incidence of the digestive system tumors such as gastric cancer and colon cancer is in China in not
Disconnected ascendant trend.It is at present operative treatment to the more effective treatment method of primary gastric cancer and colon cancer, since patient is in hand
Resistance declines in art therapeutic process, while store period is more in surgical procedure, is easy to be seriously affected by fungal infection
The postoperative wound healing of patient and rehabilitation process, therefore research and development has both effective medicine of antitumor and antimycotic double action
Object is of great significance.
Bittersweet (Solanum lyratum), it is alias solanum lyratum, Mao Fengteng, bittersweet, be Solanaceae (Solanaceae)
Bittersweet category herbaceos perennial.First recorded in Shennong's Herbal, with more than 2000 years medicinal histories, have clearing heat and promoting diuresis,
Removing toxicity for detumescence, anticancer and other effects.Clinically for treating various cancers, to gastric cancer, lung cancer, cervical carcinoma, liver cancer, cancer of the esophagus and knot
The tools such as intestinal cancer have a better effect.Modern pharmacological studies have shown that bittersweet antitumor, antiallergy, improve immunity of organisms, it is antibacterial,
Anti-inflammatory, liver protection etc. all has preferable pharmacological activity.Since the 1990s, chemistry of the domestic and foreign scholars to bittersweet
Ingredient has carried out extensive research, it was found that a variety of chemical components, but focus mostly in its water soluble ingredient, wherein with steroid alkaloid
Class content is larger, and document report is more, and reports less, compound of the present invention to the research of its liposoluble constituent
Solanrubiellin A is a new anthraquinone dimer class compound isolated from the fat-soluble extraction position of bittersweet, is closed
In preparation method and antimycotic and antitumor activity research there is not yet document report.
Summary of the invention
For above situation, for the defect for solving the prior art, the purpose of the present invention is just to provide a kind of with antimycotic
With the preparation method and applications of the anthraquinone dimer class compound of anti-tumor activity, can effectively solve preparation have it is antimycotic and
The problem of anthraquinone dimer class compound of anti-tumor activity, realization prepares antimycotic and anti-tumor drug.
The technical solution that the present invention solves is that such compound is isolated Solanrubiellin from bittersweet
A, chemical structural formula are as follows:
Preparation method is, comprising the following steps:
1) dry bittersweet herb is ground into coarse powder, the ethyl alcohol that the volumetric concentration of 6 times of bittersweet herb amounts is 95% is added
In solution, refluxing extraction 3 times, Extracting temperature is 95 DEG C, extraction time 2h, combined extract, filtering, and filtrate decompression is concentrated into
Without alcohol taste, concentrate is obtained；Distilled water is added in concentrate to be suspended, obtains the suspension that concentrate relative density is 1.1, then
Successively with the petroleum ether isometric with suspension, methylene chloride, ethyl acetate and extracting n-butyl alcohol, dichloromethane extract is taken,
Solvent is recovered under reduced pressure, obtains dichloromethane extract；
2) dichloromethane extract for taking step 1) to obtain is successively 30 with volume ratio through silica gel column chromatography initial gross separation:
1, the petroleum ether-ethyl acetate system of 20:1,10:1,5:1,1:1,0:1 carry out gradient elution, eluent are collected, through thin layer color
Spectrum (TLC) is analyzed and merges similar fraction, obtains 12 mainstream part Fr.1~Fr.12, wherein fraction Fr.8 (petroleum ether-acetic acid
Ethyl ester 5:1 elution fraction) silica gel column chromatography is continued on through, be 10:1,7:1,5:1,3 according to petroleum ether and ethyl acetate volume ratio:
1, the gradient of 2:1,0:1 are eluted, and obtain 6 Arius part Fr.8A~Fr.8F；
3) the Arius part Fr.8D (petroleum ether-ethyl acetate 3:1 elution fraction) obtained to step 2) is through Sephadex LH-
20 column chromatographys, using pure methanol as eluent, flow velocity 0.5mL/min collects yellow colour band fraction, and pressurization concentration obtains
Crude product containing Solanrubiellin A；
4) the Solanrubiellin A crude product for taking step 3) to obtain is dissolved with methanol, then with Reverse phase preparative HPLC points
From purifying, using volume ratio for 65:35 methanol-water as eluant, eluent, flow velocity is that 3mL/min is eluted, and is obtained
Solanrubiellin A。
Preparation process of the present invention is simple, reliable and stable, and the purity is high (98% or more) of compound is easy to industrialization promotion,
The compound has antimycotic and anti-tumor activity through test, opens new way for antimycotic and anti-tumor drug research and development
Diameter has actual clinical meaning.
Specific embodiment
Specific embodiments of the present invention will be described in further detail with reference to embodiments.
Embodiment 1
The extraction separation of compound and Structural Identification:
1) dry bittersweet herb 20kg is taken, coarse powder is ground into, is added in the ethanol solution of the volumetric concentration 95% of its 6 times amounts
Refluxing extraction 3 times, Extracting temperature is 95 DEG C, extraction time 2h, combined extract, filtering, and filtrate decompression is concentrated into no alcohol taste,
Obtain concentrate；Distilled water is added in concentrate to be suspended, obtains concentrate relative density and is 1.1 suspension, then successively use
Isometric petroleum ether, methylene chloride, ethyl acetate and extracting n-butyl alcohol, take dichloromethane extract, depressurize back with suspension
Solvent is received, dichloromethane extract 68g is obtained；
2) dichloromethane extract for taking step 1) to obtain is successively 30 with volume ratio through silica gel column chromatography initial gross separation:
1, the petroleum ether-ethyl acetate system of 20:1,10:1,5:1,1:1,0:1 carry out gradient elution, eluent are collected, through thin layer color
Spectrum (TLC) is analyzed and merges similar fraction, and 12 mainstream part Fr.1~Fr.12 are obtained.Wherein fraction Fr.8 (petroleum ether-acetic acid
Ethyl ester 5:1 elution fraction, 4.7g) silica gel column chromatography is continued on through, be 10:1,7:1,5 according to petroleum ether and ethyl acetate volume ratio:
1, the gradient of 3:1,2:1,0:1 are eluted, and obtain 6 Arius part Fr.8A~Fr.8F；
3) Arius part Fr.8D (petroleum ether-ethyl acetate 3:1 elution fraction, 128mg) that step 2) obtains is passed through
Sephadex LH-20 column chromatography, using pure methanol as eluent, flow velocity 0.5mL/min collects yellow colour band fraction, adds
Pressure concentration, obtains the crude product containing compound 1；
4) crude product for taking step 3) to obtain is dissolved with methanol, is then isolated and purified with Reverse phase preparative HPLC, with volume ratio
Methanol-water for 65:35 is eluant, eluent, and flow velocity is that 3mL/min is eluted, and obtains compound 1 (20.8mg), chemical structure
And number is as follows:
The compound 1 that the present invention is prepared is Yellow amorphous powder, and high resolution mass spectrum measures the compound molecular weight
For 567.1637 [M+Na]+, calculate that its molecular formula is C31H28O9.Ultraviolet spectra is shown in 203,227,252,289 and 440nm
The characteristic absorption peak of quinones；Infrared spectroscopy is in 3479cm-1There is the absorption peak of hydroxyl, 1670cm in place-1And 1623cm-1
For the characteristic absorption peak of two carbonyls；1H H NMR spectroscopy (500MHz, DMSO-d6) data are as follows: 12.50 (1H, s, 1-OH) and
12.0 (1H, s, 8-OH), 7.82 (1H, t, J=8.5Hz, H-6), 7.73 (1H, d, J=8.5Hz, H-5), 7.36 (1H, d, J=
8.5Hz, H-7), 7.18 (1H, s, H-2), 6.75 (1H, brs, H-2 '), 6.54 (1H, brs, H-4 '), 5.19 (1H, d, J=
10.0Hz, 10 '-OH), 5.09 (1H, d, J=4.5Hz, H-9 '), 5.02 (a-OH of 1H, s, 8 '), 4.98 (1H, d, J=4.0Hz,
8 '-OH), the 4.68 (- OH of 1H, d, J=4.5Hz, 9 '), 4.48 (1H, dd, J=12.0,5.5Hz, H-5 '), 3.95 (1H, brs,
H-8 '), 3.89 (1H, d, J=17.5Hz, H-11a), the 3.82 (- OCH of 3H, s, 1 '3), 3.50 (1H, d, J=10.0Hz, H-
10 '), 2.22 (3H, s, H-11 '), 2.16 (1H, m, H-7 ' a), 1.99 (1H, d, J=17.5Hz, H-11b), 1.99 (1H, m,
H-6′a),1.58(1H,m,H-7′b),1.42(1H,m,H-6′b)。
13C H NMR spectroscopy (125MHz, DMSO-d6) data are as follows: 162.0 (C-1), 121.3 (C-2), 155.9 (C-3),
143.6(C-4),127.6(C-4a),119.2(C-5),137.3(C-6),123.8(C-7),161.1(C-8),115.8(C-
8a),191.7(C-9),113.8(C-9a),182.5(C-10),133.9(C-10a),35.7(C-11),158.5(C-1′),
111.1(C-2′),137.5(C-3′),123.5(C-4′),138.6(C-4′a),42.5(C-5′),20.9(C-6′),26.9
(C-7′),66.8(C-8′),74.7(C-8′a),64.2(C-9′),122.2(C-9′a),73.3(C-10′),49.4(C-10′
a),21.0(C-11′),55.5(1′-OCH3)。
The foregoing is merely the optimal embodiments of the present invention, and for those skilled in the art, the present invention can have
Various modifications and variations.All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on, should all
It is included within protection scope of the present invention.
Anthraquinone dimer class compound prepared by the present invention is tested, and has antimycotic and anti-tumor activity, related experiment
Data is as follows:
One, the purity detecting of compound
Using the purity of high performance liquid chromatography detection noval chemical compound.Chromatographic condition is as follows, chromatographic column: Kromasil 100-
5, C-18 (250 × 4.6mm, 5 μm)；Mobile phase: acetonitrile/water gradient (5% → 95%)；Time: 65min；Flow velocity: 1ml/min；
Detection wavelength: 210nm；254nm；Column temperature: 25 DEG C；Sample introduction: 10 μ l.It is measured through area normalization method, Solanrubiellin A
Purity be 98.48%.
Two, antifungal activity is tested
Staphylococcus aureus S.epidermidis ATCC 29213, staphylococcus epidermis S.epidermidis ATCC
12228, enterococcus faecalis E.faecalis ATCC700221, escherichia coli E.coli ATCC 25922, Pseudomonas aeruginosa
P.aeruginosaATCC 27853, the above bacterial strain are all from institute of Materia Medica,Chinese Academy of Medical Sciences.
Using the micro doubling dilution of meat soup, the minimal inhibitory concentration (MIC) of Compound ira vitro bacteriostasis, summary are measured
It is as follows: with pancreas junket trunk soybean broth (TSB) culture experiment bacterium, in 37 DEG C of cultures (about 16-20h) overnight to about 0.5
Mcfarland concentration (1 × 108It is spare when CFU).First test sample is dissolved into higher concentration in ethanol, uses Cation-
Adjusted Mueller Hinton (CAMH) meat soup, which carries out doubling dilution, makes sample concentration range from 256 μ g/mL to 0.25 μ
g/mL.In addition, preparing certain density rifampin and lavo-ofloxacin as positive control using identical culture solution.In 96 holes
The drug containing culture solution of 100 μ L various concentrations of every hole addition and 100 μ L are appropriate diluted containing bacteria culture fluid through CAMH on plate, make final
Bacteria concentration is 5 × 108CFU/mL.Adding bacterium solution as negative control using the CAMH meat soup of not drug containing, (CAMH culture medium, bacterium solution are each
100 μ L), the CAMH broth bouillon of bacterium solution is not added as blank control (200 μ L of CAMH culture medium).After 96 pore plate by sealing
It is placed in 35 DEG C of insulating boxs, is incubated for for 24 hours.It is obviously grown to precondition with bacterium in negative control hole, is observed by the naked eye, with
Bacterium is the MIC (μ g/mL) of the drug without the drug minimum concentration obviously grown in dosing metapore, and experiment is parallel in triplicate.
It the results are shown in Table 1.
Inhibiting effect (MIC, μ g/mL) of the table 1Solanrubiellin A to various bacteria
The results show that compound Solanrubiellin A is to staphylococcus aureus, staphylococcus epidermis and excrement intestines ball
Bacterium shows significant bacteriostatic activity, and MIC value is 1.08-5.44 μ g/mL, wherein the inhibitory activity to staphylococcus epidermis is aobvious
It writes and is better than positive control drug rifampin, this using such compound as novel antibacterial medicament research and development for being of great significance.
Three, anti-tumor activity is tested
Experiment cell strain used is international tumor cell line, i.e. A549 (adenocarcinoma of lung), HT-29 (colon cancer),
HeLa (cervical carcinoma), HepG2 (liver cancer), HL-60 (acute promyelocytic leukemic).
Experimental method is international mtt assay: according to cell growth rate, will be in the tumour cell of logarithmic growth phase
96 well culture plates are inoculated in 100 holes μ L/, 100 hole μ L/ of dosing again of adherent growth 24 hours.Each concentration sets three multiple holes.And
If negative control group, solvent control group, positive controls (adriamycin)；Tumour cell cultivates 72 at 37 DEG C under the conditions of 5%CO2
Hour, then incline culture solution, and 20 μ L MTT (5mg/mL) are added in every hole, continues culture 4 hours in incubator；Discard culture
150 μ L DMSO dissolution is added in base, every hole, and shaking table mixes gently 10 minutes；OD value is measured under microplate reader 490nm wavelength.Experiment knot
Fruit is shown in Table 2.
Inhibiting effect (inhibiting rate) of the table 2Solanrubiellin A to kinds of tumor cells
| A549 | HT-29 | HeLa | HepG2 | HL-60 | |
| Solanrubiellin A | 78.46% | 69.10% | 82.42% | 57.13% | 60.17% |
Above-mentioned table 2 the experimental results showed that, Solanrubiellin A all shows five kinds of different tumor cell lines
Apparent inhibiting effect, wherein being more than to the inhibiting rate of A549 (adenocarcinoma of lung) and HeLa (cervical carcinoma) two kinds of tumor cell lines
70%, show preferable antitumous effect.
Four, conclusion
1, the present invention extracts the new anthraquinone dimer class compound of isolated one kind, experiment card from studies of Solanum lyratum Thunb
Bright, which has significant inhibit to staphylococcus epidermis, staphylococcus aureus and enterococcus faecalis
Effect, wherein the inhibitory activity to staphylococcus epidermis is better than positive control drug rifampin, while to source of people stomach cancer cell line
(A549) and source of people colon cancer cell line (HT-29) has stronger inhibitory activity, and can conveniently be prepared into a variety of pharmaceutical dosage forms,
Clinic is facilitated to take.The new antimycotic and anti-tumor drug of development that is found to be of the new anthraquinone dimer compound of the present invention provides
New lead compound has good development and application prospect.
2, preparation process of the present invention is simple, reliable and stable, the purity is high (98% or more) of compound, is easy to industrialization and pushes away
Extensively, new approach is opened for antimycotic and anti-tumor drug research and development, there is actual clinical meaning.
Claims (7)
1. a kind of with antimycotic and anti-tumor activity anthraquinone dimer class compound, which is characterized in that the compound be from
Isolated Solanrubiellin A, chemical structural formula in bittersweet are as follows:
2. the preparation method described in claim 1 with antimycotic and anti-tumor activity anthraquinone dimer class compound,
It is characterized in that, comprising the following steps:
1) dry bittersweet herb is ground into coarse powder, the ethanol solution that the volumetric concentration of 6 times of bittersweet herb amounts is 95% is added
In, refluxing extraction 3 times, Extracting temperature is 95 DEG C, extraction time 2h, combined extract, filtering, and filtrate decompression is concentrated into no alcohol
Taste obtains concentrate；Distilled water is added in concentrate to be suspended, obtains the suspension that concentrate relative density is 1.1, then successively
With the petroleum ether isometric with suspension, methylene chloride, ethyl acetate and extracting n-butyl alcohol, dichloromethane extract is taken, is depressurized
Recycling design obtains dichloromethane extract；
2) dichloromethane extract for taking step 1) to obtain is successively 30:1,20 with volume ratio through silica gel column chromatography initial gross separation:
1, the petroleum ether-ethyl acetate system of 10:1,5:1,1:1,0:1 carry out gradient elution, eluent are collected, through thin-layer chromatographic analysis
And merge similar fraction, 12 mainstream part Fr.1~Fr.12 are obtained, wherein fraction Fr.8 continues on through silica gel column chromatography, according to stone
Oily ether and ethyl acetate volume ratio are that the gradient of 10:1,7:1,5:1,3:1,2:1,0:1 are eluted, and obtain 6 Arius
Part Fr.8A~Fr.8F；
3) the Arius part Fr.8D obtained to step 2) is through Sephadex LH-20 column chromatography, using pure methanol as eluent, stream
Speed is 0.5mL/min, collects yellow colour band fraction, and pressurization concentration obtains the crude product containing Solanrubiellin A；
4) the Solanrubiellin A crude product for taking step 3) to obtain is dissolved with methanol, is then separated with Reverse phase preparative HPLC pure
Change, using volume ratio for 65:35 methanol-water as eluant, eluent, flow velocity be 3mL/min eluted, obtain Solanrubiellin
A。
3. described in claim 1 there is antimycotic and anti-tumor activity anthraquinone dimer class compound to prepare antifungal
Application in object.
4. according to right 3 there is antimycotic and anti-tumor activity anthraquinone dimer class compound to prepare antifungal
Application in object, which is characterized in that the fungi is staphylococcus aureus, staphylococcus epidermis and enterococcus faecalis.
5. described in claim 1 there is antimycotic and anti-tumor activity anthraquinone dimer class compound to prepare antineoplastic
Application in object.
6. according to claim 5 anti-swollen in preparation with antimycotic and anti-tumor activity anthraquinone dimer class compound
Application in tumor medicine, which is characterized in that the tumour is that adenocarcinoma of lung, colon cancer, cervical carcinoma, liver cancer and acute early young grain are white
Blood disease.
7. according to claim 1 have antimycotic and anti-tumor activity anthraquinone dimer class compound, feature exists
In compound and pharmaceutically acceptable carrier are prepared into tablet, capsule, injection, powder-injection, granule, Fat Emulsion
Agent, micro-capsule, dripping pill, ointment or skin-permeable and control-released plaster dosage form drug.
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| CN114230538B (en) * | 2021-12-21 | 2023-11-17 | 蚌埠医学院 | Cyclic anthraquinone compound and preparation method and application thereof |
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