CN114031579A - Preparation and application of daphnane diterpenoid compounds in lilac daphne flower buds - Google Patents
Preparation and application of daphnane diterpenoid compounds in lilac daphne flower buds Download PDFInfo
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Abstract
Preparation and application of daphnane diterpenoid compounds in daphnia genkwa buds, belongs to the technical field of medicine, and particularly relates to two new daphnane diterpenoid compounds yuanhuaakine A and D extracted and separated from daphnia genkwa buds of daphnia in daphnia. The compound is obtained by adopting chromatographic methods such as silica gel, HP20 column chromatography, ODS column chromatography, HPLC and the like. The invention also relates to the application of the compound 1-2 in preparing anti-tumor cell active drugs. The preparation method is simpleThe obtained compound has high purity, and the obtained compound has good tumor cell inhibiting activity of A549, Hep3B and MCF-7 cell line.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to 2 daphnane diterpenoid compounds extracted and separated from lilac daphne flower buds and application thereof in preparation of antitumor biological activity.
Background
Tumors are one of the major diseases that are seriously threatening to human health and life. With the change of living environment, the pressure of life of people is increased, the onset age of malignant tumor is gradually younger, and the research and development of antitumor drugs are further accelerated. Wherein, searching active ingredients from natural products is also an important development direction in the research and development of antitumor drugs.
The Daphne genkwa Sieb. et Zucc. has been reported in the literature to have various chemical components, wherein the Daphne diterpenoid has better anti-tumor cell activity. The daphnane diterpenoid compound is obtained by extracting flower buds of lilac daphne and has better anti-tumor cell line activity. The compounds and the activities thereof related to the present invention have not been reported in patents or literatures so far.
Disclosure of Invention
The invention firstly aims to provide 2 daphnane diterpenoid compounds and a preparation method thereof;
the invention also provides application of the daphnane diterpenoid compound in preparing a medicament with anti-tumor activity.
The 2 daphnane diterpenoid compounds extracted and separated from daphnane plant lilac daphne of daphniaceae have the following structures:
the preparation technical scheme of the invention comprises the following steps:
(1) reflux-extracting dried flos genkwa buds with 70% industrial ethanol, mixing extractive solutions, concentrating to obtain extract, sequentially extracting the extract with dichloromethane and ethyl acetate, subjecting the concentrated extract to silica gel column chromatography, performing gradient elution with dichloromethane-methanol system, and collecting 4 fractions (Fr.A-Fr.D).
(2) And separating the fraction Fr.C by HP20 column chromatography, eluting with ethanol water gradient, and collecting 4 fractions (Fr.C-1-Fr.C-4).
(3) The fractions Fr.C-1, Fr.C-2, Fr.C-3 and Fr.C-4 are separated by ODS column, cross-combined, and eluted with ethanol water gradient, and collected to obtain new 4 fractions (Fr.C-I, Fr.C-II, Fr.C-III, Fr.C-IV).
(4) Passing the fractions Fr.C-II and Fr.C-IV through silica gel column respectively, and gradient eluting with petroleum ether/ethyl acetate; wherein, the fraction Fr.C-II-3 obtained by elution of the fraction Fr.C-II is eluted by preparative HPLC with methanol/water to obtain 10 fractions (Fr.C-II-3-1 to Fr.C-II-3-10), wherein the fraction Fr.C-II-3-4 is subjected to semi-preparative HPLC chromatography, eluted by acetonitrile/water, and separated and purified to obtain a compound 1; and (3) eluting the fraction Fr.C-IV-4 obtained by eluting the fraction Fr.C-IV with preparative HPLC (high performance liquid chromatography) and methanol/water to obtain 14 fractions (Fr.C-IV-4-1-Fr.C-IV-4-14), and eluting the fraction Fr.C-IV-4-10 with acetonitrile/water by semi-preparative HPLC chromatography to obtain the compound 2.
The above preparation method, wherein:
the gradient of dichloromethane-methanol in the step (1) is as follows: 100:1 to 1:1 (v/v).
The gradient elution concentration of the ethanol water in the step (2) is as follows: 20%, 40%, 60%, 90%.
The gradient elution concentration of the ethanol water in the step (3) is as follows: 20%, 40%, 60%, 80%, 90%.
In the step (4), the petroleum ether/ethyl acetate is 100: 1-1: 2(v/v), the ratio of the prepared liquid phase methanol/water is 85:15(v/v), and the ratio of the semi-prepared liquid phase acetonitrile/water is 70:30 (v/v).
The obtained compounds 1 and 2 were subjected to system structure identification, and the results are shown in FIGS. 1-17 and as follows:
1H NMR(600MHz,CDCl3) The presence of ten aromatic proton signals δ 8.01(1H, m),7.92(2H, m),7.55(1H, m),7.49(1H, m),7.43(2H, t, J ═ 7.8Hz),7.38(2H, t, J ═ 7.8Hz) in the low field of the spectrum suggests that there are two mono-substituted benzene rings for this compound; proton signals on one set of terminal double bonds δ 5.16(1H, s),5.17(1H, s); 4 vicinal oxymethylene proton signals δ 6.02(1H, dd, J ═ 3.0Hz),4.57(1H, d, J ═ 5.1Hz),4.09(1H, dd, J ═ 9.9,2.1Hz),3.56(1H, s); the signals for the hydroxymethyl protons attached to the quaternary carbon are 4.74(1H, d, J ═ 12.7Hz), δ 4.31(1H, d, J ═ 12.7 Hz). The high field region contains 1 methyl group δ 1.88(3H, s) attached to the quaternary carbon, 2 methyl groups δ 1.01(3H, d, J ═ 6.5Hz) attached to the tertiary carbon, and 0.95(3H, d, J ═ 7.2 Hz).13C NMR(150MHz,CDCl3) The spectrum shows a 34 carbon signal, with the carbonyl carbon signals on the two benzoyloxy groups being δ 167.1,166.4; a pair of terminal double-bonded carbon signals δ 145.1,114.2; the carbon signals delta 0133.4,133.2,130.0X 3,129.9X 2,129.5,128.6X 2,128.5X 2 on two groups of monosubstituted benzene rings. Meanwhile, the characteristic quaternary carbon signal of daphnane diterpene ortho ester delta 1117 disappears, which indicates that the oxygen ring of the ortho ester of the compound is cracked. In the high field region, there are 3 methyl carbon signals δ 19.2,15.6, 15.8. The compound is judged to be a daphnane diterpenoid compound with two benzoyl substitutions through the nuclear magnetic data. According to the presence of delta 6.02(H-14) to delta 167.1(C-1') and delta 4.74 and 4.31 (H-1') in the HMBC spectra of the compounds2Correlation of-20) to δ 167.1(C-1') identifies the attachment of two benzoyl groups at the C-14 and C-20 positions of the compound, respectively. The planar structure of the compound can be determined by the analysis.
In the NOESY spectra, the correlation of H-10/H-2, H-10/H-3 and H-10/H-5 indicates that H-2, H-3, H-5 and H-10 are in the beta plane, while the correlation of H-7 and H-20 also indicates that H-7 is also in the beta plane. Furthermore, the correlation of H-16a/H-8 and H-16b/H-14 confirms that H-8 and H-14 are also located on the beta plane. The relative configuration of compound 1 was thus determined. The absolute configuration of compound 1 was determined by calculation and comparison with observed ECD. It is finally determined as 2S,3S,4R,5S,6R,7S,8S,9R,10S,11R,13R, 14R. Compound 1 was simultaneously single crystal grown and the absolute configuration of 1 was further confirmed by X single crystal diffraction. After the search of the sciflinder database, the compound 1 is a novel compound which is not reported and is named as yuanhuakene A.
Correlation of H-10 with H-2, H-3, and H-5 and H-7 with H-8, H, as shown in the NOESY spectra2Correlation of-20 with H-14, defines the relative configuration of Compound 2. Meanwhile, the absolute configuration of compound 2 was determined to be 2S,3S,4S,5R,6R,7R,8S,9R,10S,11R,13R,14R by comparing the calculated and measured ECD data. After the search of the sciflinder database, the compound 2 is a new compound which is not reported and is named as yuanhuakened D.
TABLE 1 Nuclear magnetic data for Compound 1
TABLE 2 NMR data for Compound 2
The 2 daphnane diterpenoid compounds 1 and 2 related to the invention are evaluated for the activity of inhibiting the growth of tumor cell lines. The results show that compounds 1 and 2 show tumor cell inhibitory activity against a549, Hep3B, and MCF-7 cell lines similar to the positive drugs. Therefore, the daphnane diterpenoid compounds 1 and 2 have the potential of serving as anti-tumor cell medicines.
The invention also provides a pharmaceutical composition which comprises the daphnane diterpenoid compounds 1 and/or 2 in the lilac daphne flower bud and a pharmaceutically acceptable carrier or excipient.
The invention has the advantages that the compounds 1 and 2 are both new compounds, are both optical pure compounds with determined spatial configuration, have better anti-tumor cell growth activity and have further development value.
Drawings
FIG. 1 Structure of Compounds 1 and 2;
figure 2 mass spectrum of compound 1;
FIG. 3 preparation of Compound 11H-NMR Spectroscopy (600MHz, CDCl)3);
FIG. 4 preparation of Compound 113C-NMR Spectroscopy (150MHz, CDCl)3);
FIG. 5 HSQC spectra of Compound 1 (60)0MHz,CDCl3);
FIG. 6 HMBC spectra (600MHz, CDCl) of Compound 13);
FIG. 7 preparation of Compound 11H-1H COSY spectrum;
FIG. 8 NOESY spectrum (600MHz, CDCl) of Compound 13);
FIG. 9 is a single crystal diagram of Compound 1;
figure 10 mass spectrum of compound 2;
FIG. 11 preparation of Compound 21H-NMR Spectroscopy (600MHz, CDCl)3);
FIG. 12 preparation of Compound 213C-NMR Spectroscopy (150MHz, CDCl)3);
FIG. 13 HSQC spectra (600MHz, CDCl) of Compound 23);
FIG. 14 HMBC spectra (600MHz, CDCl) of Compound 23);
FIG. 15 preparation of Compound 21H-1H COSY spectrum;
FIG. 16 NOESY spectrum (600MHz, CDCl) of Compound 23);
Figure 17 experimental and calculated ECD spectra for compounds 1 and 2;
FIG. 18 tumor cell inhibitory activity of compounds 1 and 2 on A549, Hep3B, and MCF-7 cell lines; all data are expressed as means ± SD (three independent experiments); cissplatina, sorafenib, doxorubicina were positive drugs.
Detailed Description
The examples set out below are intended to assist the person skilled in the art in a better understanding of the invention, but do not limit it in any way.
Example 1
The preparation method of daphnane diterpenoid compounds 1-2 in lilac daphne flower buds specifically comprises the following operations:
(1) reflux-extracting dried flos Genkwa (60kg) of Thymelaeaceae with 70% industrial ethanol for 3 times, mixing extractive solutions, and concentrating to obtain extract. The obtained extract is extracted by dichloromethane and ethyl acetate successively. The dichloromethanol layer portion (2400g) and the ethyl acetate layer portion (1300g) were subjected to reduced pressure silica gel column chromatography, and gradient elution was performed using a methylene chloride-methanol system (100:1, 50:1, 30:1, 20:1, 10:1, 5:1,3:1,1: 1), thereby collecting 4 fractions (fr.a to fr.d).
(2) Fraction Fr.C (230g) was subjected to HP20 column chromatography eluting with a gradient of ethanol in water (20%, 40%, 60%, 90%) and a total of 4 fractions (Fr.C-1 to Fr.C-4) were collected.
(3) The 4 fractions Fr.C-1(25g), Fr.C-2(32g), Fr.C-3(35g) and Fr.C-4(43g) were subjected to ODS column chromatography, combined with cross-over, and eluted with an ethanol-water gradient (20%, 40%, 60%, 80%, 90%), to collect 4 new fractions (Fr.C-I, Fr.C-II, Fr.C-III, Fr.C-IV).
(4) Fractions Fr.C-II (15.5g) and Fr.C-IV (18.2g) were passed through silica gel columns and eluted with a petroleum ether/ethyl acetate gradient (100:1, 50:1, 30:1, 20:1, 10:1, 5:1,3:1,1:1,1: 2); wherein, the fraction Fr.C-II-3 obtained by elution of the fraction Fr.C-II is eluted by preparative HPLC with methanol/water volume ratio (85:15) to obtain 10 fractions (Fr.C-II-3-1 to Fr.C-II-3-10), the fraction Fr.C-II-3-4 is subjected to semi-preparative HPLC chromatography with acetonitrile/water volume ratio (70:30) for separation and purification to obtain a compound 1(38.1 mg); and (3) carrying out preparative HPLC on a fraction Fr.C-IV-4 obtained by eluting the fraction Fr.C-IV by using a methanol/water volume ratio (85:15) to obtain 14 fractions (Fr.C-IV-4-1-Fr.C-IV-4-14), carrying out semi-preparative HPLC chromatography on the Fr.C-IV-4-10 by using an acetonitrile/water volume ratio (70:30), and respectively separating and purifying to obtain a compound 2(2.5 mg).
Example 2
Detecting the activity of daphnane diterpenoid compounds 1-2 in lilac daphne flower bud.
The growth inhibitory activity of the compounds 1-2 prepared in example 1 on tumor cell lines A549, Hep3B, and MCF-7 was tested using the MTT method. Cells grown logarithmically at 6X 104M L, 100. mu.L/well in 96-well plates, 3 multiple wells set and placed at 37 ℃ in 5% CO2Incubate in incubator for 24 h. Different concentrations of test compounds 1 and 2(0.1,1,10,50 μ M) were then dosed for 48 h.
After 48h of drug action, cells were incubated with MTT solution (0.5mg/mL) for an additional 4h at 37 ℃. After the culture solution was aspirated, DMSO was added to each well to completely dissolve the culture solution, and the absorbance was measured at 490nm using a microplate reader. All experiments were performed in parallel and repeated three times, and the results of setting the blank and the positive control are shown in fig. 18. The two compounds 1 and 2 described in the invention show better inhibitory activity to A549, Hep3B and MCF-7 cell lines.
Claims (10)
2. the daphnane diterpenoid compound in lilac daphne flower bud according to claim 1, wherein the daphnane diterpenoid compound is extracted and separated from lilac daphne flower bud of daphnia of Thymelaeaceae.
3. A method for preparing daphnane diterpenoid compounds in lilac daphne flower buds as claimed in claim 1 or 2, which is characterized by comprising the following steps:
(1) reflux-extracting dried lilac daphne flower buds with industrial ethanol, mixing extracting solutions, concentrating to obtain an extract, sequentially extracting the extract with dichloromethane and ethyl acetate, concentrating the extract, performing gradient elution by a dichloromethane-methanol system through silica gel column chromatography, and collecting 4 fractions (Fr.A-Fr.D);
(2) separating the fraction Fr.C by HP20 column chromatography, eluting with ethanol water gradient, and collecting 4 fractions (Fr.C-1-Fr.C-4);
(3) separating the fractions Fr.C-1, Fr.C-2, Fr.C-3 and Fr.C-4 with ODS column, cross-mixing, eluting with ethanol water gradient, and collecting to obtain new 4 fractions (Fr.C-I, Fr.C-II, Fr.C-III, Fr.C-IV);
(4) passing the fractions Fr.C-II and Fr.C-IV through silica gel column respectively, and gradient eluting with petroleum ether/ethyl acetate; wherein, the fraction Fr.C-II-3 obtained by elution of the fraction Fr.C-II is eluted by preparative HPLC with methanol/water to obtain 10 fractions (Fr.C-II-3-1 to Fr.C-II-3-10), wherein the fraction Fr.C-II-3-4 is subjected to semi-preparative HPLC chromatography, eluted by acetonitrile/water, and separated and purified to obtain a compound 1; and (3) eluting the fraction Fr.C-IV-4 obtained by eluting the fraction Fr.C-IV with preparative HPLC (high performance liquid chromatography) and methanol/water to obtain 14 fractions (Fr.C-IV-4-1-Fr.C-IV-4-14), and eluting the fraction Fr.C-IV-4-10 with acetonitrile/water by semi-preparative HPLC chromatography to obtain the compound 2.
4. The method for preparing daphnane diterpenoid compounds in lilac daphne flower buds as claimed in claim 3, wherein the gradient of dichloromethane-methanol in the step (1) is as follows: 100: 1-1: 1.
5. The method for preparing daphnane diterpenoid compounds in lilac daphne flower buds according to claim 3, wherein the gradient elution concentration of ethanol water in the step (2) is as follows: 20%, 40%, 60%, 90%.
6. The method for preparing daphnane diterpenoid compounds in lilac daphne flower buds according to claim 3, wherein the gradient elution concentration of ethanol water in the step (3) is as follows: 20%, 40%, 60%, 80%, 90%.
7. The method for preparing daphnane diterpenoid compounds in lilac daphne flower buds as claimed in claim 3, wherein the gradient of petroleum ether/ethyl acetate in the step (4) is 100: 1-1: 2, the ratio of prepared liquid-phase methanol/water is 85:15, and the ratio of semi-prepared liquid-phase acetonitrile/water is 70: 30.
8. A pharmaceutical composition comprising the daphnane diterpenoid compounds of lilac daphne buds of claim 1 or 2 and a pharmaceutically acceptable carrier or excipient.
9. The application of daphnane diterpenoid compounds in lilac daphne flower buds as defined in claim 1 or 2 or the pharmaceutical composition as defined in claim 8 is characterized by being applied to the preparation of drugs with antitumor cell activity.
10. The use of claim 9, wherein the tumor cells comprise tumor cells of the a549, Hep3B, and MCF-7 cell lines.
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CN115160337A (en) * | 2022-08-19 | 2022-10-11 | 沈阳药科大学 | 1 alpha-alkyl daphnane diterpenoid compounds, and preparation method and application thereof |
CN115160337B (en) * | 2022-08-19 | 2023-11-10 | 沈阳药科大学 | 1 alpha-alkyl daphnane diterpenoid compound, and preparation method and application thereof |
CN115677520A (en) * | 2022-11-18 | 2023-02-03 | 扬州大学 | Diterpene compound and preparation method and application thereof |
CN115677520B (en) * | 2022-11-18 | 2024-04-02 | 扬州大学 | Diterpene compound and preparation method and application thereof |
CN116440211A (en) * | 2023-04-24 | 2023-07-18 | 广东奇灵制药有限公司 | Antibacterial and anti-inflammatory capsule and preparation method thereof |
CN116854704A (en) * | 2023-07-06 | 2023-10-10 | 沈阳药科大学 | Daphnane diterpenoid derivative with anti-liver cancer activity and preparation method and application thereof |
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