CN102219686A - Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses - Google Patents
Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses Download PDFInfo
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- CN102219686A CN102219686A CN2011101016198A CN201110101619A CN102219686A CN 102219686 A CN102219686 A CN 102219686A CN 2011101016198 A CN2011101016198 A CN 2011101016198A CN 201110101619 A CN201110101619 A CN 201110101619A CN 102219686 A CN102219686 A CN 102219686A
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Abstract
The invention discloses a coffeeoyl derivative, a preparation method and a use thereof. The caffeeoyl derivative is 1alpha, 2beta-O-dicaffeoylcyclopentan-3beta-ol having a structure represented by a formula (I), and can be extracted and separated from a traditional Chinese medicine of scabrous elephantfoot herb. The coffeeoyl derivative can be provided for preparing drugs for preventing and treating respiratory syncytial viruses (RSV). In vitro antiviral experiments reveal that: compared to a general clinical antiviral drug of ribavirin, the 1alpha, 2beta-O- dicaffeoylcyclopentan-3beta-ol has stronger anti-RSV activity and lower toxicity on host cells; when the 1alpha, 2beta-O- dicaffeoylcyclopentan-3beta-ol is combined with the ribavirin, a synergistic interaction is provided. Therefore, the 1alpha, 2beta-O-dicaffeoylcyclopentan-3beta-ol has high-performance, low toxic anti-RSV activity with novel mechanism of action, and has good application prospect.
Description
Technical field
The invention belongs to medical technical field, particularly a kind of caffeoyl derivative and preparation method thereof and the purposes in preparation anti respiratory syncytial virus infection medicine.
Background technology
Elephantopus scaber L. (Elephantopus scaber) is that composite family (Compositae) Elephantopus scaber L. belongs to (Elephantopus) plant, also be Scabrous Elephantfoot Herb, Scabrous Elephantfoot Herb, God in charge of the Earth's English, mainly be distributed in the south China and the southwest of China, the effect of tool heat-clearing, cool blood, dampness removing, the diseases such as tonsillitis, pharyngitis, flu, urinary tract infections, dermatitis and hepatitis that are used for the treatment of among the people are included in version " Chinese pharmacopoeia in 1977.Main chemical ingredients has sesquiterpenoids, flavonoid and caffeoyl quinic acid compounds in the Elephantopus scaber L..Modern pharmacological research shows, the crude extract of Elephantopus scaber L. has effects such as antiviral, antibacterial, antitumor and analgesic, wherein, there is research report Elephantopus scaber L. aqueous extract to have anti respiratory syncytial virus (RSV) activity preferably, but, antiviral activity research to Elephantopus scaber L. only rests on the crude extract, and its activeconstituents is not studied report.Result for retrieval at State Intellectual Property Office's coordinate indexing and CNKI, Scifinder Scholar shows, do not find new caffeoyl alcohol derivate and preparation method thereof in the Elephantopus scaber L. and as the patent and the document of the purposes of the medicine of preparation anti respiratory syncytial virus.
Respiratory virus infection is one of communicable disease of serious harm human health.Respiratory syncytial virus (respiratory syncytial virus, RSV) belong to the Paramyxoviridae Pneumovirus, its caused respiratory tract infection, laryngitis, trachitis, bronchitis and pneumonia etc. are common disease and frequently-occurring diseases clinically, and Susceptible population is child and old man.The serology statistics shows, all infects RSV before 100% children grow up.Up to now, rsv infection is not still had effective specificity prophylactico-therapeutic measures, nucleoside medicine virazole (ribavirin) is unique by the chemicals of FDA approval treatment rsv infection, but because its curative effect is limited, toxic side effect is big, clinical application effect is unsatisfactory.In addition, though curative effect is better, life cycle is long, expense is high, is not widely used in clinical as yet for RSV antibody class medicine (as RSV monoclonal antibody Synagis).Therefore, need badly and seek and develop efficient anti-rsv infection medicine safe in utilization, high specificity.
Summary of the invention
In order to solve above-mentioned the deficiencies in the prior art part, primary and foremost purpose of the present invention is to provide a kind of caffeoyl derivative.
Another object of the present invention is to provide the preparation method of above-mentioned caffeoyl derivative.
A further object of the present invention is to provide the purposes of above-mentioned caffeoyl derivative in the preparation antiviral.
Purpose of the present invention is achieved through the following technical solutions: a kind of caffeoyl derivative, this caffeoyl derivative have suc as formula structure shown in (I), called after 1 α, and 2 β-O-two caffeoyl rings penta-3 β-alcohol:
The preparation method of above-mentioned caffeoyl derivative, comprise following operation steps: the dry root of Elephantopus scaber L. (Elephantopus scaber) is pulverized, ethanolic soln diacolation with mass percent concentration 95% extracts, extracting solution is evaporated to nothing alcohol flavor with Rotary Evaporators and obtains total medicinal extract, with total medicinal extract distilled water suspendible, use sherwood oil, ethyl acetate and n-butanol extraction more successively, obtain petroleum ether part, ethyl acetate extract and n-butanol portion respectively behind the recovery solvent; N-butanol portion is adopted the macroporous adsorptive resins segmentation, with mass percent concentration is that 0～95% aqueous ethanolic solution carries out gradient elution, the collection mass percent concentration is 20～60% ethanolic soln wash-out gained elutriant, obtains efficient part behind the decompression and solvent recovery; Obtain the pure product of above-mentioned caffeoyl derivative behind efficient part process silica gel column chromatography, Sephadex LH-20 column chromatography and preparative high-performance liquid chromatographic (HPLC) column chromatography for separation, the purifying.
Described Elephantopus scaber L. is a composite family Elephantopus scaber L. platymiscium.
The purposes of above-mentioned caffeoyl derivative in the medicine of preparation anti respiratory syncytial virus.
The medicine of described anti respiratory syncytial virus contains 1 α that treats significant quantity, 2 β-O-two caffeoyl rings penta-3 β-pure and mild pharmaceutically acceptable carrier.
The medicine of described anti respiratory syncytial virus contains 1 α that treats significant quantity, 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole.
Described 1 α, the mass ratio between 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole be preferably 2: 1～and 1: 2.
The medicine of described anti respiratory syncytial virus is made powder, pill, tablet, capsule, oral liquid, aerosol or injection.
The present invention has following advantage and beneficial effect with respect to prior art: the present invention is directed to present Respirovirus treatment field urgent problem, seek the preventing respiratory viruses medicine of make new advances efficient, low toxicity.1 α provided by the invention, 2 β-O-two caffeoyl rings penta-3 β-alcohol is the new compound of natural origin, the medicine virazole that its anti respiratory syncytial virus specific activity is used always clinically is strong, and more much smaller than virazole to the toxicity of host cell.In addition, the extracorporeal antivirus effect experiment shows, 1 α, and when 2 β-O-two caffeoyl rings penta-3 β-alcohol and virazole combined utilization, the tool synergistic function.Therefore, 1 α, the antiviral activity of 2 β-O-two caffeoyl rings penta-3 β-alcohol has efficiently, low toxicity, mechanism of action novel features, and good application prospects is arranged.
Description of drawings
Fig. 1 is 1 α; the active photo figure of anti respiratory syncytial virus (RSV) during 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole combined utilization; wherein a is normal laryngocarcinoma (Hep-2) cell photo; b is the Hep-2 cell photo of rsv infection; c is for adding 1 α of 0.31 μ g/mL; the Hep-2 cell photo of the rsv infection behind 2 β-O-two caffeoyl rings penta-3 β-alcohol; d is for adding 1 α of 0.31 μ g/mL, the Hep-2 cell photo of the rsv infection behind 2 β-O-two caffeoyl rings penta-3 β-pure and mild 0.63 μ g/mL virazole mixture.
Embodiment
The present invention is described in further detail below in conjunction with embodiment and accompanying drawing, but embodiments of the present invention are not limited thereto.
Embodiment 1:
Elephantopus scaber L. (is picked up from Guangdong, identify by the Guangzhou medicinal material senior engineer officer of the company wheat ball that shakes) dry root pulverize, with the mass percent concentration of 12 times of quality of Elephantopus scaber L. is that 95% aqueous ethanolic solution diacolation extracts, extracting solution is evaporated to nothing alcohol flavor with Rotary Evaporators and obtains total medicinal extract, the distilled water suspendible that total medicinal extract is added 2 times of volumes, use sherwood oil, ethyl acetate and n-butanol extraction successively, obtain petroleum ether part, ethyl acetate extract and n-butanol portion behind the decompression and solvent recovery respectively; N-butanol portion is adopted the segmentation of D101 macroporous adsorptive resins, with mass percent concentration is that 0～95% aqueous ethanolic solution carries out gradient elution, the collection mass percent concentration is 20～60% aqueous ethanolic solution wash-out gained elutriant, and decompression and solvent recovery obtains efficient part; Efficient part is crossed silica gel column chromatography earlier separate,, use Sephadex LH-20 column chromatography for separation again with chloroform and methanol solvate system gradient elution, employing methyl alcohol and water volume ratio are 1: 1 solvent systems wash-out, elutriant silica gel thin-layer plate analysis merges, and obtains caffeoyl derivative crude product; With caffeoyl derivative crude product preparative high-performance liquid chromatographic purifying, methyl alcohol and water volume ratio are 6: 4 solvent systems wash-out, and rotatory evaporator evaporated under reduced pressure solvent obtains the pure product of caffeoyl derivative (purity＞95%).
The pure product of gained caffeoyl derivative are yellow powder, specific rotation: [α]
20 D=-251.6 ° (c 0.50, MeOH).The structure of this compound by analyze UV spectrum (UV), infrared spectra (IR), proton nmr spectra (
1H NMR), carbon spectrum (
13C NMR), two dimensional NMR spectrum (H-HCOSY, HMQC, HMBC, NOESY) and high resolution mass spectrum (HRMS) supposition obtain.
Use positive ion mass spectrum ESR-MS:m/z=443[M+H]
+, show that molecular weight is 442.
Measure [M+Na] with high resolution mass spectrum HRESI-MS:m/z
+Be 465.1152, the demonstration molecular formula is C
23H
22O
9Na (theoretical value: 465.1156).
UV spectrum UV (MeOH) λ
Max(log ε): 217,243,300,326nm shows coffee acyl.
There is hydroxyl (3383cm in the data presentation of infrared spectra
-1), carbonyl (1684cm
-1) and phenyl ring (1597,1521cm
-1).
Proton nmr spectra (
1H NMR) and carbon spectrum (
13C NMR) data based two-dimensional spectrum
1H-
1The data of H COSY, HSQC and HM C belong to, and the results are shown in Table 1.
Table 1 caffeoyl derivative
1H NMR and
13C NMR data (δ in ppm, J in Hz, in MeOD)
Hydrogen spectrum data presentation: 2 trans double bond [δ
H7.59,6.27,7.50 and 6.18 (each 1H, d, J=16.0Hz)], the hydrogen atom [δ on 6 phenyl ring
H7.00 and 6.98 (each 1H, d, J=2.0Hz), 6.72 and 6.87 (each 2H, dd, J=8.0,2.0Hz)] and 3 oxygen methyne [δ of company
H5.65 (1H, m), 5.12 (1H, dd, J=8.3,2.8Hz) and 4.37 (1H, m)].Carbon spectrum data presentation: 2 carbonyl (δ
C168.4,168.6), 2 two key (δ
C147.7,147.5,115.2,115.2) and 3 oxygen methyne (δ of company
C76.2,69.8,69.1) and 2 phenyl ring.Can infer that from above data this compound is the derivative of two caffeoyl.
From the visible δ 5.65 of H-H COSY (H-1)
5.12 (H-2)
4.37 (H-3)
2.29 (H-4)
2.12 (H-5)
5.65 Fourier Series expansion technique (H-1), HMBC composes visible δ 5.62 (H-1), and (C-9 ") is relevant, and the two dimensional structure that can determine this compound is 1,2-O-two caffeoyl rings penta-3-alcohol with δ 168.4 with δ 168.6 (C-9 '), δ 5.10 (H-2).It is all relevant with H-5 with H-3 to compose visible H-2 from NOESY, and it is relevant with H-3 to lose H-1, so this compound structure is defined as 1 α, 2 β-O-two caffeoyl rings penta-3 β-alcohol, and structural formula is as follows.
Embodiment 2:1 α, the external anti respiratory syncytial virus activity of 2 β-O-two caffeoyl rings penta-3 β-alcohol
(1) cell, virus and experiment material: respiratory syncytial virus (RSV, Long strain), host cell are laryngeal cancer cell (Hep-2 cell); Positive control drug is virazole (ribavirin); Cell is grown in the MEM substratum that mass percent concentration is 10% calf serum (FBS); Keeping liquid is the MEM substratum that contains the FBS of mass percent concentration 1%.
(2) preparation of sample solution: respectively with embodiment 1 gained 1 α; 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole is made into the solution that concentration is 40mg/mL with dimethyl sulfoxide (DMSO) (DMSO); with keeping the sample solution that liquid is made sample ligand 200 μ g/mL and 10 μ g/mL respectively, be used separately as the experiment of cytotoxicity and antiviral activity again.
(3) cytotoxicity of usefulness tetrazolium salts (MTT) colorimetric method for determining compound:
With the Hep-2 cell cultures in 96 well culture plates, wait monolayer cell grow good after, add with series concentration (concentration is 200～6.25 μ g/mL) sample solution of keeping the dilution of liquid sesquialter, at 37 ℃, 5%CO
2Cultivated 3 days in the incubator; Add 10 μ L MTT solution (5mg/mL disposes with buffered soln), continue to cultivate 4 hours.The sucking-off sample solution adds methyl-sulphoxide, under the room temperature, 96 orifice plates is placed microwell plate vibrator vibration 10 minutes.Measure the OD value in each hole with microplate reader, the measurement wavelength is 570nm, and reference wavelength is 630nm, the half lethal toxicity concentration (CC of calculation sample pair cell
50).Establish 4 equalizing ports for every group, every group of experiment repeats 3 times.Calculation result, the curve that draws is obtained half toxic concentration (CC
50).
(4) measure antiviral activity by the inhibition degree (cytopathic effect reduction assay) of observation sample pair cell pathology effect:
With the Hep-2 cell cultures in 96 well culture plates, wait monolayer cell grow good after, add with keeping liquid and dilute 100 good sesquialters and count infective dose (100TCID
50) viral liquid, add again with series concentration (concentration is 10～0.31 μ g/mL) sample solution of keeping the dilution of liquid sesquialter, at 37 ℃, 5%CO
2Cultivated in the incubator 3～4 days.Every day observation of cell pathology effect (CPE) under inverted microscope degree, and record: the no CPE of-expression; + expression 0～25% cell has CPE; 2+ represents that 25～50% cells have CPE; 3+ represents that 50～70% cells have CPE; 4+ represents that 75～100% cells have CPE.Estimate half-inhibition concentration (IC at last
50).Selectivity index (SI)=CC
50/ IC
50
Experimental result:
1 α, the IC of 2 β-O-two caffeoyl rings penta-3 β-pure vitro inhibition respiratory syncytial virus
50=0.63 μ g/mL, CC
50＞200 μ g/mL, SI＞318.65.
The IC of virazole vitro inhibition respiratory syncytial virus
50=1.50 μ g/mL, CC
50=62.50 μ g/mL, SI=41.67.
As seen, 1 α, 2 β-O-two caffeoyl rings penta-3 β-alcohol suppresses the IC of RSV
50Value is lower than the positive control drug virazole, and its SI value (SI=CC
50/ IC
50) be much higher than virazole, 1 α is described, the antiviral activity of 2 β-O-two caffeoyl rings penta-3 β-alcohol has efficiently, the characteristics of low toxicity.
Embodiment 3:1 α, the external anti respiratory syncytial virus determination of activity of 2 β-O-two caffeoyl rings penta-3 β-alcohol and virazole drug combination
(1) cell, virus and experiment material: respiratory syncytial virus (RSV, Long strain), host cell are laryngeal cancer cell (Hep-2 cell); Positive control drug is virazole (ribavirin); Cell is grown in the MEM substratum that mass percent concentration is 10% calf serum (FBS); Keep liquid and be mass percent concentration and be the MEM substratum of 1% FBS.
(2) preparation of sample solution: respectively with embodiment 1 gained 1 α; 2 β-O-two caffeoyl rings penta-3 β-pure sample and virazole sample are made into the solution that concentration is 40mg/mL with dimethyl sulfoxide (DMSO) (DMSO); with keeping liquid respectively with 1 α; 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole is mixed with the solution of 0.31 μ g/mL and 0.62 μ g/mL, again both was mixed into testing sample solution in 1: 1 by volume.
(3) adopt cytopathic-effect inhibition assay (cytopathic effect reduction assay) to measure 1 α, the antiviral activity of 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole combined utilization:
With the Hep-2 cell cultures in 96 well culture plates, wait monolayer cell grow good after, add with keeping liquid and dilute 100 good sesquialters and count infective dose (100TCID
50) viral liquid, add testing sample solution again, at 37 ℃, cultivated in the 5%CO2 incubator 3～4 days.Every day observation of cell pathology effect (CPE) under inverted microscope degree, and record: the no CPE of-expression; + expression 0～25% cell has CPE; 2+ represents that 25～50% cells have CPE; 3+ represents that 50～70% cells have CPE; 4+ represents that 75～100% cells have CPE.Take a picture with digital camera at last.
Experimental result as shown in Figure 1,1 α, 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole is being lower than their half-inhibition concentration (IC
50Be respectively 0.63 μ g/mL and 1.50 μ g/mL) time, The combined is used energy 100% inhibition by the cytopathy that RSV causes, illustrates that both have synergy.
Embodiment 4:1 α, the preparation of 2 β-O-two caffeoyl rings penta-3 β-pure tablet
Get embodiment 1 gained 1 α, 2 β-O-two caffeoyl rings penta-3 β-pure 1g mixes with Microcrystalline Cellulose 27g and Magnesium Stearate 2g, and mixture breaks into diameter 6mm with Singlepunchtabletpress, the sheet of weight 300mg.Every contains 1 α in this tablet, 2 β-O-two caffeoyl rings penta-3 β-pure 10mg.
Embodiment 5:1 α, the preparation of 2 β-O-two caffeoyl rings penta-3 β-pure capsule
Get embodiment 1 gained 1 α, 2 β-O-two caffeoyl rings penta-3 β-pure 1g mixes with lactose 27g, Magnesium Stearate 2g, with every 300mg filled capsules.In this capsule, each capsule contains 1 α, 2 β-O-two caffeoyl rings penta-3 β-pure 10mg.
Embodiment 6:1 α, the preparation of 2 β-O-two caffeoyl rings penta-3 β-pure powder
Get embodiment 1 gained 1 α, 2 β-O-two caffeoyl rings penta-3 β-pure 5g mixes with starch 25g, adds water and makes softwood, crosses 12 mesh sieves and carries out granulation, obtains powder after the drying.In this powder, contain 1 α among every 300mg, 2 β-O-two caffeoyl rings penta-3 β-pure 50mg.
The foregoing description is a preferred implementation of the present invention; but embodiments of the present invention are not restricted to the described embodiments; other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (8)
1. caffeoyl derivative, it is characterized in that: this caffeoyl derivative has suc as formula structure shown in (I):
2. the preparation method of a kind of caffeoyl derivative according to claim 1, it is characterized in that comprising following operation steps: the dry root of Elephantopus scaber L. is pulverized, ethanolic soln diacolation with mass percent concentration 95% extracts, extracting solution is evaporated to nothing alcohol flavor with Rotary Evaporators and obtains total medicinal extract, with total medicinal extract distilled water suspendible, use sherwood oil, ethyl acetate and n-butanol extraction more successively, obtain petroleum ether part, ethyl acetate extract and n-butanol portion respectively behind the recovery solvent; N-butanol portion is adopted the macroporous adsorptive resins segmentation, with mass percent concentration is that 0～95% aqueous ethanolic solution carries out gradient elution, the collection mass percent concentration is 20～60% ethanolic soln wash-out gained elutriant, obtains efficient part behind the decompression and solvent recovery; Efficient part is through obtaining the caffeoyl derivative of purity＞95% behind silica gel column chromatography, Sephadex LH-20 column chromatography and the preparative high-performance liquid chromatographic column chromatographic isolation and purification.
3. preparation method according to claim 1 is characterized in that: described Elephantopus scaber L. is a composite family Elephantopus scaber L. platymiscium.
4. the purposes of caffeoyl derivative according to claim 1 in the medicine of preparation anti respiratory syncytial virus.
5. purposes according to claim 4 is characterized in that: the medicine of described anti respiratory syncytial virus contains 1 α that treats significant quantity, 2 β-O-two caffeoyl rings penta-3 β-pure and mild pharmaceutically acceptable carrier.
6. purposes according to claim 4 is characterized in that: the medicine of described anti respiratory syncytial virus contains 1 α that treats significant quantity, 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole.
7. purposes according to claim 6 is characterized in that: described 1 α, the mass ratio of 2 β-O-two caffeoyl rings penta-3 β-pure and mild virazole is 2: 1～1: 2.
8. purposes according to claim 4 is characterized in that: the medicine of described anti respiratory syncytial virus is made powder, pill, tablet, capsule, oral liquid, aerosol or injection.
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| CN102988346A (en) * | 2012-11-19 | 2013-03-27 | 何晓涛 | Application of Aphanamixoid A in respiratory syncytial virus (RSV) resistant medicine |
| CN104490909A (en) * | 2014-12-03 | 2015-04-08 | 暨南大学 | Application of derivative of caffeic acid in preparation of medicine for resisting RSV (respiratory syncytial virus) |
| CN104644711A (en) * | 2014-11-21 | 2015-05-27 | 暨南大学 | Extract of plant in blumea genus as well as preparation method and application thereof |
| CN110156628A (en) * | 2019-06-19 | 2019-08-23 | 暨南大学 | A kind of ring triol derivates and the preparation method and application thereof |
| CN112933080A (en) * | 2021-01-20 | 2021-06-11 | 暨南大学 | Application of elephantopin lactone compounds in preparation of medicines with respiratory syncytial virus resisting effect |
| CN114105807A (en) * | 2021-11-18 | 2022-03-01 | 暨南大学 | Hydroxycyclohexane diamide compound and preparation method and application thereof |
| CN117069685A (en) * | 2023-10-13 | 2023-11-17 | 暨南大学 | Cinnamoyl alkyl polyketone compound, preparation method and application thereof |
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| CN102988346A (en) * | 2012-11-19 | 2013-03-27 | 何晓涛 | Application of Aphanamixoid A in respiratory syncytial virus (RSV) resistant medicine |
| CN104644711A (en) * | 2014-11-21 | 2015-05-27 | 暨南大学 | Extract of plant in blumea genus as well as preparation method and application thereof |
| CN104644711B (en) * | 2014-11-21 | 2018-05-22 | 暨南大学 | A kind of Blumea balsamifera genus plants extract and preparation method and application |
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| CN104490909B (en) * | 2014-12-03 | 2017-06-23 | 暨南大学 | A kind of application of caffeic acid derivative in the medicine with anti-RSV virus functions is prepared |
| CN110156628A (en) * | 2019-06-19 | 2019-08-23 | 暨南大学 | A kind of ring triol derivates and the preparation method and application thereof |
| CN110156628B (en) * | 2019-06-19 | 2022-05-17 | 暨南大学 | Cyclotriol derivative and preparation method and application thereof |
| CN112933080A (en) * | 2021-01-20 | 2021-06-11 | 暨南大学 | Application of elephantopin lactone compounds in preparation of medicines with respiratory syncytial virus resisting effect |
| CN114105807A (en) * | 2021-11-18 | 2022-03-01 | 暨南大学 | Hydroxycyclohexane diamide compound and preparation method and application thereof |
| CN114105807B (en) * | 2021-11-18 | 2023-08-18 | 暨南大学 | Hydroxycyclohexanamide compound and preparation method and application thereof |
| CN117069685A (en) * | 2023-10-13 | 2023-11-17 | 暨南大学 | Cinnamoyl alkyl polyketone compound, preparation method and application thereof |
| CN117069685B (en) * | 2023-10-13 | 2024-01-09 | 暨南大学 | Cinnamoyl alkyl polyketone compound, preparation method and application thereof |
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Application publication date: 20111019 |