CN107840822B - Euphorbia lathyris alcohol and preparation method and application thereof - Google Patents
Euphorbia lathyris alcohol and preparation method and application thereof Download PDFInfo
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- CN107840822B CN107840822B CN201711296697.1A CN201711296697A CN107840822B CN 107840822 B CN107840822 B CN 107840822B CN 201711296697 A CN201711296697 A CN 201711296697A CN 107840822 B CN107840822 B CN 107840822B
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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Abstract
The invention provides a novel compound shown as a formula (I) and a preparation method of the compound shown as the formula (I). The experimental result shows that the invention separates a brand new compound from euphorbia lathyris seeds; the compound has excellent inhibitory action on cancer cells, and can be used for preparing anti-tumor medicaments; the preparation method of the compound has the advantages of mild reaction conditions, low energy consumption, high efficiency, low cost, environmental protection and the like, and is very suitable for industrial application.
Description
Technical Field
The invention relates to the field of natural substance extraction, and particularly relates to euphorbia lathyris alcohol and a preparation method and application thereof.
Background
Malignant tumors have become one of the most serious diseases that endanger human health at present. According to the world health organization, about 500 million people die each year due to malignant tumor worldwide, and 1000 million newly discovered malignant tumor patients each year. The development of antitumor drugs is of great importance in the treatment of malignant tumors. More than 60% of clinically used anticancer drugs are reported to be derived from natural products. Therefore, prevention of cancer development by studying anticancer substances in natural products has become an important field of cancer prevention research.
Euphorbia lathyris L, also called Qianjin, is a species of Euphorbia of Euphorbiaceae. Biennial herbs, the whole plant has no hairs. The root is columnar, and the stem is upright. Leaves were reciprocally opposite, linear, needle-shaped, full margin. The inflorescence is single-born and nearly bell-shaped. Most male flowers, 1 female flower. The capsule is in a triangular spherical shape, and is smooth and unhairing. Seed columnar to ovoid, brown or taupe. The flowering period is 4-7 months, and the fruit period is 6-9 months. The whole herb is toxic. Has medical value. The seeds, stems, leaves and white milk in the stems of euphorbia lathyris can be used as the medicine and are traditional Chinese medicinal materials. The compendium of materia medica and so on records that the plant has the efficacies of expelling water and reducing swelling, breaking stasis and killing insects, and so on.
At present, studies have reported that euphorbiaceae plants have strong antitumor activity. However, the research on the chemical components and the biological activity of euphorbia lathyris seeds is still insufficient.
Disclosure of Invention
In order to solve the above problems, the present invention provides a method for extracting a compound represented by formula I from Euphorbia lathyris seeds.
The invention provides a compound represented by the formula (I):
the invention provides a method for preparing a compound shown as a formula (I), which comprises the following steps:
(1) extracting Euphorbiae Lathyridis semen with ethyl acetate to obtain Euphorbiae Lathyridis semen extract;
(2) dissolving the extract obtained in the step (1) in a mixed solution of petroleum ether and acetonitrile for extraction to obtain acetonitrile part concentrated extract;
(3) and (3) taking the concentrated paste obtained in the step (2), carrying out chromatographic separation on the concentrated paste by using a silica gel column, and sequentially carrying out reaction on the concentrated paste by using n-hexane: gradient elution is carried out by using ethyl acetate as an eluent, wherein the ethyl acetate is 20:1, 10:1, 15:1, 12:1, 10:1, 8:1, 6:1, 4:1, 3:1, 2:1 and 0:1 (v/v); taking n-hexane: the eluent fractions of ethyl acetate 2:1(v/v) were separated on a C18 column with methanol: gradient elution is carried out by using water as eluent, wherein the water is 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0 (v/v); taking methanol: water-80: 20(v/v) fractions of the eluent were separated on a C18 column with methanol: water 70:30, 75:25, 80:20(v/v) as mobile phase gradient elution; taking methanol: and (5) obtaining the compound shown in the formula (I) by using the eluent with the ratio of 75: 25.
Further, in the step (1), the volume fraction of ethyl acetate was 99.5%.
Further, in the step (1), the weight volume ratio of the euphorbia lathyris seeds to the ethyl acetate is 1: 6-10 g/ml; preferably 1:8 g/ml.
Further, in the step (2), the volume ratio of the petroleum ether to the acetonitrile in the mixed solution is 1: 1.
Further, in the step (2), the weight-volume ratio of the euphorbia lathyris seed extract to the petroleum ether-acetonitrile is 1: 10-30 g/ml; preferably 1:30 g/ml.
The invention provides application of the compound in preparing an anti-tumor medicament.
Furthermore, the tumor is breast cancer, liver cancer or kidney cancer.
The invention also provides an anti-tumor pharmaceutical composition, which is a preparation prepared by taking the compound shown in the formula (I) as an active ingredient and adding pharmaceutically acceptable auxiliary materials or auxiliary ingredients.
Furthermore, the tumor is breast cancer, liver cancer or kidney cancer.
Test results show that the invention separates brand new compounds from euphorbia lathyris seeds; the compound has excellent inhibitory action on cancer cells, and can be used for preparing anti-tumor medicaments; the preparation method of the compound has the advantages of mild reaction conditions, low energy consumption, high efficiency, low cost, environmental protection and the like, and is very suitable for industrial application.
Obviously, many modifications, substitutions, and variations are possible in light of the above teachings of the invention, without departing from the basic technical spirit of the invention, as defined by the following claims.
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Drawings
FIG. 1 is a mass spectrum of a compound of the present invention.
FIG. 2 is a drawing of a compound of the present invention1H-NMR spectrum chart.
FIG. 3 is a drawing of a compound of the present invention13C-NMR spectrum chart.
FIG. 4 is a DEPT spectrum of a compound of the present invention.
FIG. 5 shows NMR of the compounds of the invention1H-1H COSY spectrogram.
FIG. 6 shows the HMQC spectra of the compounds of the invention.
FIG. 7 is a nuclear magnetic resonance HMBC spectrum of a compound of the invention.
FIG. 8 is a NOESY chart of nuclear magnetic resonance of the compound of the present invention.
FIG. 9 shows the inhibition of four cancer cells by the compounds of the present invention.
Detailed Description
EXAMPLE 1 preparation of Compounds of the invention
(1) 10kg of euphorbia lathyris seeds are taken and crushed into powder, and 80L of ethyl acetate (the volume fraction is 99.5%) is soaked (the weight-volume ratio of euphorbia lathyris seeds to ethyl acetate is 1:8 g/ml). Filtering and extracting once every 5 days for 5 times; mixing the extractive solutions, and recovering solvent under reduced pressure to obtain Euphorbiae Lathyridis semen extract.
(2) Taking 420g of the extract, dissolving the extract in 12.6L of petroleum ether-acetonitrile (1:1) mixed solution (the weight-volume ratio of the euphorbia lathyris seed extract to the petroleum ether-acetonitrile is 1:30g/ml), and extracting for three times to obtain the lower acetonitrile part; recovering solvent from acetonitrile part of the extract under reduced pressure to obtain acetonitrile part of brown concentrated extract;
(3) 284g of the acetonitrile partially concentrated paste is mixed with the same volume of silica gel (60-80 meshes), and the mixture is subjected to silica gel column chromatography (60-80 meshes) with normal hexane: gradient elution with ethyl acetate 20:1, 10:1, 15:1, 12:1, 10:1, 8:1, 6:1, 4:1, 3:1, 2:1, 0:1(V/V), followed by elution with 100% methanol, and collection of each gradient eluate. Adding n-hexane: the ethyl acetate ═ 2:1(V/V) fractions of the eluent were concentrated under reduced pressure, and the concentrate was subjected to C18 (200-: gradient eluting with water at ratio of 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10, and 100:0(V/V), eluting with 100% methanol, and concentrating the eluate at ratio of 80:20 to obtain concentrated solution; purifying the concentrated solution with high performance preparative liquid chromatography, adopting octadecyl bonded silica gel chromatographic column with specification of 4.6 × 150mm × 5 μm, taking methanol: gradient elution with water at 70:30, 75:25, 80:20(V/V) as mobile phase; taking methanol: water 75:25, detection wavelength 265nm, flow rate 5ml/min, column temperature 25 ℃, proving that 5.5mg of the compound represented by formula (i) is finally obtained.
The compound shown in the formula (I) is white amorphous powder, is easy to dissolve in chloroform, has dark spots under the irradiation of ultraviolet 254nm, is negative in Libermann-Burchard reaction, and shows purple red after the heating of the sulfuric acid vanillin; HR-ESI-MS [ M + H ]]+：602.2766。
1H-NMR(600MHz，CDCl3) There are 5 methyl signals in the spectrum 2.15(3H, s, H-20), 1.32(3H, s, H-2 "), 1.22(3H, s, H-19), 2.15(3H, s, H-18), 1.08(3H, s, H-16); 3 consecutive O-methine signals 5.83(H, t, H-3), 5.45(H, d, H-5), 5.26(H, m, H-7). A benzene ring signal 8.06(2H, d, H-3 ' and H-5 '), 7.46(2H, t, H-4 ' and H-6 '), 7.58(H, t, H-5 '), a pyridine ring signal 9.35(2H, s, H-3 '), 8.75(H, s, H-4 '), 7.40(H, m, H-5 '), 8.42(H, d, H-6 ').
13C-NMR(600MHz，CDCl3) The spectra show 35 carbon signals, and in combination with the DEPT spectral data, compounds have 6 methyl carbon signals (28.5, 20.8, 15.6, 14.6, 14.1), 3 methylene carbon signals (113.5, 47.5, 30.2), 17 methine carbon signals (153.5, 151.7, 139.9, 137.6, 130.1, 129.8, 129.8, 128.6, 128.6, 123.5, 77.2, 73.8, 69.5, 52.0, 37.3, 32.0, 26.3), and 10 quaternary carbon signals (207.3, 169.6, 166.4, 164.8, 143.9, 138.4, 133.4, 126.6, 85.5, 24.3). One ketone signal 207.3 and one phenyl ring signal (133.4, 130.1, 129.8, 128.6).
Combined with mass spectrum,1H-NMR，13C-NMR and DEPT data, presuming that the compound may have a formula of C35H39NO8The molecular weight was 601 and the unsaturation degree was 17.
Combining the above data with HMQC and HMBC signals, the compounds were concluded to be euphorbiane-type diterpene compounds, and to contain one benzoyl group and one nicotinoyl group.
NOESY spectrum shows related signals H-3/H-5 beta, which shows that the benzoyl at the 3-position is determined to be alpha configuration when the H-3/H-5 beta is in alpha configuration on the same side as benzol-3 and acetyl-5. Finally determining the compound as 3 alpha-O-benzoyl-5-O-acetyl-7-O-nicotinoyl-15-hydroxy-retinyl alcohol with the name of 3 alpha-O-benzoyl-5-O-acetyl-7-O-
nicotinoyl-15-hydroxynaphthalene, having the following structural formula:
of the compounds of Table 11H-NMR、13C-NMR data attribution
Example 2 antitumor Activity of Compounds of the invention
(1) Experimental Material
Tumor cells: human breast cancer cell MCF-7, human liver cancer cell HepG2, human kidney cancer cell 786-0 and breast cancer cell MDA-MB-468; are all provided by cell banks of the Chinese academy of sciences.
Preparing a cisplatin solution: cisplatin (1.5 mg) was weighed out and dissolved in 50. mu.L DMSO to obtain a 100.0mM concentration of cisplatin solution. Then 10.0 mul of cisplatin solution with the concentration of 100.0mM is taken and added into 990.0 mul of DMEM culture medium to obtain cisplatin solution with the concentration of 1000.0 mul; then 100.0 mul of cisplatin solution with the concentration of 1000.0 mul is taken and added into 900.0 mul of DMEM culture medium to obtain the cisplatin solution with the concentration of 100.0 mul; adding 300.0 μ L of 100.0 μ L cisplatin solution into 700.0 μ L DMEM culture medium to obtain 30.0 μ M cisplatin solution; taking 100.0 mu L of cisplatin solution with the concentration of 100.0 mu M, and adding 900.0 mu L of DMEM culture medium to obtain cisplatin solution with the concentration of 10 mu M; taking 100.0 mu L of cisplatin solution with the concentration of 30.0 mu M, and adding 900.0 mu L of DMEM culture medium to obtain cisplatin solution with the concentration of 3 mu M; mu.L of cisplatin solution (100.0. mu.L) at a concentration of 10.0. mu.M was added to 900.0. mu.L of DMEM medium to obtain a cisplatin solution at a concentration of 1. mu.M.
Preparation of a test compound sample solution: 2.00mg of the compound represented by the formula (I) prepared in example 1 was weighed out and dissolved in 33.3. mu.L of DMSO to obtain a compound solution with a concentration of 100.0 mM. Adding 3.2 μ L of 100.0mM compound solution into 800.0 μ L DMEM medium to obtain 400.0 μ M compound solution; adding 400.0 μ L of compound solution with concentration of 400.0 μ M into 400.0 μ L of DMEM culture medium to obtain compound solution with concentration of 200.0 μ M; adding 400.0 μ L of 200.0 μ M compound solution into 400.0 μ L DMEM medium to obtain 100.0 μ M compound solution; adding 400.0 μ L of 100.0 μ M compound solution into 400.0 μ L DMEM medium to obtain 50.0 μ M compound solution; adding 400.0 μ L of compound solution with concentration of 50.0 μ M into 400.0 μ L of DMEM medium to obtain compound solution with concentration of 25 μ M; adding 400.0 μ L of 25.0 μ M compound solution into 400.0 μ L DMEM medium to obtain 12.5 μ M compound solution; adding 400.0 μ L of 12.5 μ M compound solution into 400.0 μ L DMEM medium to obtain 6.25 μ M compound solution; adding 400.0 μ L of 6.25 μ M compound solution into 400.0 μ L DMEM medium to obtain 3.13 μ M compound solution; 400.0. mu.L of the compound solution at a concentration of 3.13. mu.M was added to 400.0. mu.L of DMEM medium to obtain a compound solution at a concentration of 1.56. mu.M.
(2) Experimental methods
After the human breast cancer cells MCF-7, the human liver cancer cells HepG2, the human kidney cancer cells 786-0 and the breast cancer cells MDA-MB-468 in the logarithmic growth phase are digested and collected by pancreatin, the cells are inoculated into a 96-well plate at the density of 5 multiplied by 103 per well, 100 mu L of DMEM culture medium containing 10% fetal calf serum is added into each well, and the cells are incubated for 24 hours until the cells adhere to the wall for 80%. Test compound solutions were added to each well in a concentration gradient (1.56. mu.M, 3.13. mu.M, 6.25. mu.M, 12.50. mu.M, 25.00. mu.M, 50.00. mu.M, 100.00. mu.M, 200.00. mu.M, 400.00. mu.M) to give a final concentration of each test compound solution: 0.78. mu.M, 1.56. mu.M, 3.13. mu.M, 6.25. mu.M, 12.50. mu.M, 25.00. mu.M, 50.00. mu.M, 100.00. mu.M, 200.00. mu.M, with three parallel wells per set. Another 3 wells were supplemented with 100. mu.L of DMEM medium as a control. And (3) continuing incubation for 24h, taking out the 96-well plate, adding 20 mu l of 5mg/mL MTT solution under the condition of keeping out of the light, continuing incubation for 3h under the condition of keeping out of the light, measuring the absorbance value of each well at 490nm by using a microplate reader, recording the result, and calculating the inhibition rate of the cells according to the following formula as shown in FIG. 9 and Table 2:
cell inhibition (%) was 1- (absorbance of test group/absorbance of control group) × 100%
(3) Results of the experiment
TABLE 2 half inhibitory concentration of cells IC50+ SD (. mu.m)
As can be seen from FIG. 9, the compound of the present invention has inhibitory effect on four cancer cells, and the inhibitory rate is above 60%; wherein, the inhibition effect on human breast cancer cells MCF-7 is as high as 100%. As can be seen from Table 2, the compound of the invention has a remarkably stronger inhibition effect on MCF-7 than cisplatin, which shows that the compound of the invention has the best inhibition effect on human breast cancer cells MCF-7.
In conclusion, the invention separates a brand new compound from euphorbia lathyris seeds; the compound has excellent inhibitory action on cancer cells, and can be used for preparing anti-tumor medicaments; the preparation method of the compound has the advantages of mild reaction conditions, low energy consumption, high efficiency, low cost, environmental protection and the like, and is very suitable for industrial application.
Claims (15)
1. A compound of formula (I):
2. a process for preparing a compound of claim 1, wherein: the method comprises the following steps:
(1) extracting Euphorbiae Lathyridis semen with ethyl acetate to obtain Euphorbiae Lathyridis semen extract;
(2) dissolving the extract obtained in the step (1) in a mixed solution of petroleum ether and acetonitrile for extraction to obtain acetonitrile part concentrated extract;
(3) and (3) taking the concentrated paste obtained in the step (2), carrying out chromatographic separation on the concentrated paste by using a silica gel column, and sequentially carrying out reaction on the concentrated paste by using n-hexane: gradient elution is carried out by using ethyl acetate as an eluent, wherein the ethyl acetate is 20:1, 10:1, 15:1, 12:1, 10:1, 8:1, 6:1, 4:1, 3:1, 2:1 and 0:1 (v/v); taking n-hexane: the eluent fractions of ethyl acetate 2:1(v/v) were separated on a C18 column with methanol: gradient elution is carried out by using water as eluent, wherein the water is 30:70, 40:60, 50:50, 60:40, 70:30, 80:20, 90:10 and 100:0 (v/v); taking methanol: water-80: 20(v/v) fractions of the eluent were separated on a C18 column with methanol: gradient elution with water 70:30, 75:25(v/v) as mobile phase, methanol: and (5) obtaining the compound shown in the formula (I) by using the eluent with the ratio of 75: 25.
3. The method of claim 2, wherein: in the step (1), the volume fraction of ethyl acetate was 99.5%.
4. A method according to claim 2 or 3, characterized in that: in the step (1), the weight-volume ratio of the euphorbia lathyris seeds to the ethyl acetate is 1: 6-10 g/ml.
5. The method of claim 4, wherein: in the step (1), the weight-volume ratio of the euphorbia lathyris seeds to the ethyl acetate is 1:8 g/ml.
6. A method according to claim 2 or 3, characterized in that: in the step (2), the volume ratio of the petroleum ether to the acetonitrile in the mixed solution is 1: 1.
7. The method of claim 4, wherein: in the step (2), the volume ratio of the petroleum ether to the acetonitrile in the mixed solution is 1: 1.
8. The method according to any one of claims 2-3, 5, wherein: in the step (2), the weight-volume ratio of the euphorbia lathyris seed extract to the petroleum ether-acetonitrile is 1: 10-30 g/ml.
9. The method according to any one of claims 2-3, 5, wherein: in the step (2), the weight volume ratio of the euphorbia lathyris seed extract to the petroleum ether-acetonitrile is 1:30 g/ml.
10. The method of claim 4, wherein: in the step (2), the weight-volume ratio of the euphorbia lathyris seed extract to the petroleum ether-acetonitrile is 1: 10-30 g/ml.
11. The method of claim 4, wherein: in the step (2), the weight volume ratio of the euphorbia lathyris seed extract to the petroleum ether-acetonitrile is 1:30 g/ml.
12. Use of the compound of claim 1 in the preparation of an antitumor medicament.
13. Use according to claim 12, characterized in that: the tumor is breast cancer, liver cancer and kidney cancer.
14. An anti-tumor pharmaceutical composition, which is characterized in that: the compound is a preparation prepared by taking the compound shown as the formula (I) in claim 1 as an active ingredient and adding pharmaceutically acceptable auxiliary materials or auxiliary ingredients.
15. The pharmaceutical composition of claim 14, wherein: the tumor is breast cancer, liver cancer and kidney cancer.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1903848A (en) * | 2006-08-03 | 2007-01-31 | 西安皓天生物工程技术有限责任公司 | Extraction and separation method of moleplant seed sterol |
| JP2012121869A (en) * | 2010-12-10 | 2012-06-28 | Kao Corp | Bitter taste inhibitor |
| CN104447526A (en) * | 2014-11-28 | 2015-03-25 | 天津耀宇生物技术有限公司 | Preparation method of 5,15-O-diacetyl-3-O-nicotinoyl-lathyrol |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1903848A (en) * | 2006-08-03 | 2007-01-31 | 西安皓天生物工程技术有限责任公司 | Extraction and separation method of moleplant seed sterol |
| JP2012121869A (en) * | 2010-12-10 | 2012-06-28 | Kao Corp | Bitter taste inhibitor |
| CN104447526A (en) * | 2014-11-28 | 2015-03-25 | 天津耀宇生物技术有限公司 | Preparation method of 5,15-O-diacetyl-3-O-nicotinoyl-lathyrol |
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| Title |
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| 千金子中非萜类化学成分的研究;郑飞龙等;《热带亚热带植物学报》;20091231;第17卷(第3期);298-301 * |
| 千金子化学成分的研究;焦威等;《中草药》;20100228;第41卷(第2期);181-187 * |
| 续随子地上部分乙醇提取物的正己烷部分的抗肿瘤活性部位研究;张建业等;《中国中医药咨讯》;20110531;第3卷(第15期);8-9 * |
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