CN103450310A - Stigmasterol derivative and application thereof in preparation of anti-cancer drug - Google Patents
Stigmasterol derivative and application thereof in preparation of anti-cancer drug Download PDFInfo
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- CN103450310A CN103450310A CN2013103607948A CN201310360794A CN103450310A CN 103450310 A CN103450310 A CN 103450310A CN 2013103607948 A CN2013103607948 A CN 2013103607948A CN 201310360794 A CN201310360794 A CN 201310360794A CN 103450310 A CN103450310 A CN 103450310A
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Abstract
The invention discloses a stigmasterol derivative and application thereof in preparation of an anti-cancer drug. The stigmasterol derivative is shown in formula I or II, wherein R in the formula I is SO2C6H5, COCH3, COCH2Cl, COC6H5, CH2CH3, or NO2. The stigmasterol derivative disclosed by the invention has a significant inhibiting effect on a plurality of tumour cells, such as human liver epithelial cells, human gastric carcinoma cells, human breast cancer cells and human ovarian neoplasm, has low toxicity on normal cells, and can be used for preparing the drug for treating cancers.
Description
Technical field
The present invention relates to Stigmasterol derivative and the application in preparing cancer therapy drug thereof.
Background technology
Cancer has become one of disease of the maximum that threatens human health and quality of life at present, utilize the natural resources of China's abundant, effective monomer before therefrom finding, and by modifications transform acquisition efficiently, the cancer therapy drug of highly selective, low toxicity is the main direction of studying of current cancer therapy drug.
The chemoprophylaxis of tumour is to reduce one of the most direct method of cancer morbidity.For the disease of the serious harm HUMAN HEALTH such as beat cancer, people constantly find new medicine from plant.In recent years, the antitumous effect of mangostin is confirmed by people gradually.At present, for cancer occurred frequently, as lung cancer, cancer of the stomach, liver cancer, mammary cancer and colorectal carcinoma etc., studied, mangostin all embodies good anticancer effect, and progressively is deep into the anticancer mechanism of mangostin.
The activeconstituents of take in natural product is parent compound, the principle of learning according to drug molecule is carried out structural modification, design the semi-synthetic compound that may there is high reactivity, hang down toxic side effect, thereby find to be applied to a kind of important means that clinical recruit's entity is current new drug development.
Summary of the invention
The purpose of this invention is to provide a kind of mangostin derivative through chemically modified, and in the application of the medicine that is used for the treatment of cancer.
Stigmasterol derivative of the present invention is with shown in following formula I or II:
The formula I
The group of the R representative in the formula I is: SO
2c
6h
5, COCH
3, COCH
2cl, COC
6h
5, CH
2cH
3or NO
2.
Formula II.
Stigmasterol derivative of the present invention, be to extract from soybean plants, the compound that the Stigmasterol obtained through separation and purification obtains through chemically modified.
Prepare the reaction of Stigmasterol derivative of the present invention as shown in following reaction formula:
3-Phenylsulfonic acid base-5, the synthetic route chart of 22-diene-24-ethyl-courage steroid (AB-1)
3-acetoxyl group-5, the synthetic route chart of 22-diene-24-ethyl-courage steroid (AB-2)
3-chloroethene acyloxy-5, the synthetic route chart of 22-diene-24-ethyl-courage steroid (AB-3)
3-benzoyl-5, the synthetic route chart of 22-diene-24-ethyl-courage steroid (AB-4)
3-hydroxyl-5,6,22, the synthetic route chart of 23-tetrabromobisphenol 4-ethyl-courage steroid (AB-5)
3-oxyethyl group-5, the synthetic route chart of 22-diene-24-ethyl-courage steroid (AB-6)
3-nitro-5, the synthetic route chart of 22-diene-24-ethyl-courage steroid (AB-7)
By the cancer cell in vitro inhibition test, show, Stigmasterol derivative of the present invention has significant restraining effect to kinds of tumor cells such as people's liver cancer epithelial cell (HEPG-2), gastric carcinoma cells (MKN45), human breast cancer cell (MDA-MB-231), Proliferation of Human Ovarian Cell (SKOV3), and lower to normal cytotoxicity.The part derivative is all stronger than corresponding Stigmasterol and ADM to the restraining effect of HEPG-2, MDA-MB-231 and SKOV3 tumour cell, and therefore the part mangostin derivative of invention can be used for the medicine of preparation treatment cancer.
Embodiment
The present invention will be described further by following examples.
Embodiment 1.3-Phenylsulfonic acid base-5,22-diene-24-ethyl-courage steroid (AB-1) synthetic.
Get Stigmasterol 0.5g(1.21mmol) in the 50mL of nitrogen protection there-necked flask; add dry chloroform 20mL; add the about 4.3mmol of dry triethylamine 0.6 mL(); control temperature at 60 ℃; slowly drip the mixed solution of 1ml benzene sulfonyl chloride (6.0mmol) and 3 mL chloroforms, dropwise half an hour, then continue to stir; thin-layer chromatography is followed the tracks of reaction process, termination reaction after 7 hours.Filter, filtrate is washed 3 times with saturated nacl aqueous solution, and organic phase is spent the night with anhydrous sodium sulfate drying, again filters evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate=20:1) purifying, obtain white solid powder 0.523g, productive rate 78.2%; M.p.103.8 ~ 105.2 ℃;
1hNMR (CDCl
3) δ (ppm): 0.686 (s, 3H), 0.788 ~ 0.799 (m, 6H), 0.845 (d,
j=6.6Hz, 3H), 1.010 ~ 1.135 (m, 7H), 1.151 ~ 1.162 (m, 1H), 1.170 ~ 1.253 (m, 3H), 1.429 ~ 1.441 (m, 2H), 1.450 ~ 1.469 (m, 4H), 1.510 ~ 1.519 (m, 2H), 1.528 ~ 1.543 (m, 2H), 1.555 ~ 1.603 (m, 2H), 1.893 ~ 1.910 (m, 1H), 1.967 ~ 2.094 (m, 3H), 2.495 (d
j=7.8Hz, 1H), 4.196 ~ 4.229 (m, 1H), 5.013 ~ 5.041 (m; 1H), 5.125 ~ 5.165 (m, 1H), 5.399 ~ 5.414 (m, 1H); 7.527 ~ 7.545 (m, 3H), 7.718 ~ 7.734 (m, 2H); ESI-MS m/z 544.38 ([M+H]
+, 80%). Anal.Calcd for C
35h
52o
3s:C, 76.04; H, 9.48. Found:C, 75.99; H, 9.50.
Embodiment 2.3-acetoxyl group-5,22-diene-24-ethyl-courage steroid (AB-2) synthetic.
Get Stigmasterol 0.5 g(1.21 mmol) in 50 mL there-necked flasks of nitrogen protection; add dry pyridine 18 mL; control temperature at 60 ℃; slowly drip the mixed solution of 0.6ml acetic anhydride (6.0 mmol) and 3 mL chloroforms; dropwise half an hour; continue to stir, thin-layer chromatography is followed the tracks of reaction process, termination reaction after 10 hours again.Be cooled to room temperature, with 1.0 N HCl, regulate pH to 2.Filter, filtrate is extracted with ethyl acetate 3 times, and organic phase is spent the night with anhydrous sodium sulfate drying, again filters evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate=20:1) purifying, obtain white solid powder 0.473g, productive rate 86.1%; M.p.140.9 ~ 142.4 ℃;
1hNMR (CDCl
3) δ (ppm): 0.696 (s, 3H), 0.790 ~ 0.800 (m, 6H), 0.846 (d,
j=6.0Hz, 3H), 0.911 ~ 0.974 (m, 1H), 1.016 ~ 1.127 (m, 7H), 1.129 ~ 1.137 (m, 1H), 1.142 ~ 1.191 (m, 4H), 1.225 ~ 1.248 (m, 1H), 1.469 ~ 1.510 (m, 9H), 1.520 ~ 1.529 (m, 1H), 1.853 ~ 1.873 (m, 2H), 1.978 ~ 2.035 (m, 6H), 2.300 ~ 2.347 (m, 2H), 4.603 ~ 4.612 (m, 1H), 4.992 ~ 5.032 (m, 1H), 5.130 ~ 5.169 (m, 1H), 5.374 (t
j=2.4Hz, 1H); ESI-MS m/z 456 ([M+H]
+, 20%). Anal.Calcd for C
31h
50o
2: C, 81.88; H, 11.08. Found:C, 81.90; H, 11.07.
Embodiment 3.3-chloroethene acyloxy-5,22-diene-24-ethyl-courage steroid (AB-3) synthetic.
Get Stigmasterol 0.5 g(1.21 mmol) in 50 mL there-necked flasks of nitrogen protection; add dry chloroform 20 mL; add the about 4.3mmol of dry triethylamine 0.6 mL(); slowly drip the mixed solution of 0.6 ml chloroacetyl chloride (6.0 mmol) and 3 mL chloroforms under room temperature; dropwise half an hour; continue to stir, thin-layer chromatography is followed the tracks of reaction process, termination reaction after 2 hours again.Filter evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate=25:1) purifying, obtain white solid powder 0.544g, productive rate 92.0%; M.p.175.1 ~ 176.9 ℃;
1hNMR (CDCl
3) δ (ppm): 0.696 (s, 3H), 0.789 ~ 0.816 (m, 6H), 0.846 (d,
j=6.6Hz, 3H), 0.912 ~ 0.977 (m, 1H), 1.016 ~ 1.094 (m, 7H), 1.127 ~ 1.136 (m, 1H), 1.144 ~ 1.296 (m, 6H), 1.375 ~ 1.455 (m, 2H), 1.494 ~ 1.571 (m, 5H), 1.611 ~ 1.624 (m, 1H), 1.693 ~ 1.721 (m, 1H), 1.821 ~ 1.891 (m, 2H), 1.932 ~ 2.002 (m, 3H), 2.353 ~ 2.365 (m, 2H), 4.040 (s, 2H), 4.684 ~ 4.723 (m, 1H), 4.964 ~ 5.033 (m, 1H), 5.129 ~ 5.169 (m, 1H), 5.389 (t
j=1.8 Hz, 1H), ESI-MS m/z 490 ([M+H]
+, 10%). Anal.Calcd for C
31h
49o
2cl:C, 76.11, H, 10.10. Found:C, 76.10, H, 10.09.
Embodiment 4.3-benzoyl-5,22-diene-24-ethyl-courage steroid (AB-4) synthetic.
Get Stigmasterol 0.5 g(1.21 mmol) in 50 mL there-necked flasks of nitrogen protection, add dry chloroform 20 mL, add Anhydrous potassium carbonate 0.4 g(2.7 mmol).Control temperature at 80 ℃, slowly drip the mixed solution of 0.7 ml Benzoyl chloride (6.0 mmol) and 3 mL chloroforms, dropwise half an hour, then continue to stir, and thin-layer chromatography is followed the tracks of reaction process, termination reaction after 2 hours.Filter, filtrate is washed 3 times with saturated nacl aqueous solution, and organic phase is spent the night with anhydrous sodium sulfate drying, again filters evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate=25:1) purifying, obtain white solid powder 0.415g, productive rate 66.4%; M.p.156.4 ~ 157.7 ℃;
1hNMR (CDCl
3) δ (ppm): 0.712 (s, 3H), 0.797 ~ 0.811 (m, 6H), 0.852 (d,
j=6.0Hz, 3H), 0.954 ~ 1.117 (m, 9H), 1.145 ~ 1.348 (m, 5H), 1.395 ~ 1.677 (m, 8H), 1.690 ~ 1.726 (m, 2H), 1.909 ~ 1.931 (m, 1H), 1.989 ~ 2.099 (m, 4H), 2.461 ~ 2.474 (m, 2H), 4.821 ~ 4.899 (m, 1H), 5.031 ~ 5.045 (m, 1H), 5.144 ~ 5.169 (m, 1H), 5.420 (t
j=2.4 Hz, 1H), 7.429 (t,
j=7.8 Hz, 2H), 7.540 (t,
j=7.8 Hz, 1H), 8.043 (d,
j=7.8 Hz, 2H); ESI-MS m/z 518 ([M+H]
+, 10%). Anal.Calcd for C
36h
52o
2: C, 83.67; H, 10.14. Found:C, 83.65; H, 10.13.
Embodiment 5.3-hydroxyl-5,6,22,23-tetrabromobisphenol 4-ethyl-courage steroid (AB-5) synthetic.
Get Stigmasterol 0.5 g(1.21 mmol) in 50 mL there-necked flasks of nitrogen protection; add dry chloroform 20 mL; under room temperature; slowly drip the mixed solution of 2 ml Benzoyl chlorides (12.1 mmol) and 3 mL chloroforms; dropwise half an hour; continue to stir, thin-layer chromatography is followed the tracks of reaction process, termination reaction after 3.5 hours again.Filter, filtrate is washed 3 times with saturated sodium bicarbonate solution, and organic phase is spent the night with anhydrous sodium sulfate drying, again filters evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate/methyl alcohol=5:1:0.05) purifying, obtain reddish-brown pressed powder 0.377g, productive rate 42.6%; M.p.101.9 ~ 103.8 ℃;
1hNMR (CDCl
3) δ (ppm): 0.713 (s, 1H), 0.732 (s, 2H), 0.896 ~ 1.191 (m, 7H), 1.199 ~ 1.397 (m, 8H), 1.401 ~ 1.810 (m, 18H), 1.839 ~ 1.924 (m, 2H), 1.940 ~ 2.012 (m, 2H), 2.197 ~ 2.225 (m, 1H), 2.289 ~ 2.345 (m, 1H), 2.486 ~ 2.511 (m, 1H), 2.813 ~ 2.841 (m, 1H), 4.190 ~ 4.198 (m, 1H), 4.394 ~ 4.416 (m, 1H), 4.480 ~ 4.534 (m, 1H), 4.842 ~ 4.871 (m, 1H), ESI-MS m/z 733 ([M+H]
+, 60%). Anal.Calcd for C
29h
48brO:C, 47.56, H, 6.61. Found:C, 47.60, H, 6.60.
Embodiment 6.3-oxyethyl group-5,22-diene-24-ethyl-courage steroid (AB-6) synthetic.
Get chloro Stigmasterol 0.5 g(1.21 mmol) in 50 mL there-necked flasks of nitrogen protection, add dehydrated alcohol 20 mL.Control temperature at 60 ℃, stir, thin-layer chromatography is followed the tracks of reaction process, termination reaction after 5 hours.Filter evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate=20:1) purifying, obtain white solid powder 0.174g, productive rate 32.7%; M.p.132.5 ~ 133.9 ℃;
1hNMR (CDCl
3) δ (ppm): 0.696 (s, 3H), 0.790 ~ 0.824 (m, 6H), 0.845 (d,
j=6.6Hz, 3H), 0.897 ~ 0.945 (m, 1H), 0.986 ~ 1.094 (m, 9H), 1.187 ~ 1.213 (m, 6H), 1.292 ~ 1.342 (m, 1H), 1.345 ~ 1.601 (m, 8H), 1.645 ~ 1.723 (m, 1H), 1.847 ~ 1.979 (m, 2H), 1.998 ~ 2.104 (m, 3H), 2.178 ~ 2.224 (m, 1H), 2.347 ~ 2.392 (m, 1H), 3.152 ~ 3.199 (m, 1H), 3.516 ~ 3.534 (m, 2H), 5.023 ~ 5.038 (m, 1H), 5.133 ~ 5.172 (m, 2H), 5.342 (t
j=3Hz, 1H), Cl, 8.22. ESI-MS m/z 442 ([M+H]
+, 30%). Anal.Calcd for C
31h
52o:C, 84.48, H, 11.89. Found:C, 84.49, H, 11.87.
Embodiment 7.3-nitro-5,22-diene-24-ethyl-courage steroid (AB-7) synthetic.
Get chloro Stigmasterol 0.5 g(1.21 mmol) in 50 mL there-necked flasks of nitrogen protection, add dehydrated alcohol 20 mL.Under room temperature, slowly drip the ethanolic soln (6.0 mmol) of 1.0 ml Silver Nitrates, half hour, dropwise, and continues to stir, and thin-layer chromatography is followed the tracks of reaction process, termination reaction after 2 hours.Filter evaporate to dryness filtrate, silica gel column chromatography (silica gel, 200-300 order; Eluent, petrol ether/ethyl acetate=3:1) purifying, obtain white solid powder 0.266g, productive rate 48.1%; M.p.90.1 ~ 92.0 ℃;
1hNMR (CDCl
3) δ (ppm): 0.702 (s, 3H), 0.792 ~ 0.807 (m, 6H), 0.848 (d,
j=6.0Hz, 3H), 0.901 ~ 1.103 (m, 9H), 1.145 ~ 1.211 (m, 3H), 1.265 ~ 1.293 (m, 1H), 1.402 ~ 1.599 (m, 10H), 1.623 ~ 1.745 (m, 2H), 2.004 ~ 2.099 (m, 4H), 2.435 ~ 2.448 (m, 2H), 4.746 ~ 4.801 (m, 1H), 5.028 ~ 5.043 (m, 1H), 5.135 ~ 5.174 (m, 1H), 5.440 (t
j=3Hz, 1H); ESI-MS m/z 458 ([M+H]
+, 10%). Anal.Calcd for C
29h
47nO
3: C, 76.10; H, 10.35; N 3.06. Found:C, 76.07; H, 10.36, N 3.07.
Embodiment 8.Stigmasterol and derivative thereof the restraining effect to the tumor cell line growth.
Select derivative of the present invention and the natural Stigmasterol cytotoxicity to liver cancer epithelial cell (HEPG-2), gastric carcinoma cells (MKN45), human breast cancer cell (MDA-MB-231), Proliferation of Human Ovarian Cell (SKOV3).Adopt mtt assay, measure its absorbancy, compound concentration when calculating respectively cell growth inhibiting and reaching 50%, with IC
50mean.Experimental result sees the following form.
The different samples of table 1 are to suppressing the IC of NKM45 cell proliferation
50
The different samples of table 2 are to suppressing the IC of SKOV3 cell proliferation
50
The different samples of table 3 are to suppressing the IC of HEPG-2 cell proliferation
50
The different samples of table 4 are to suppressing the IC of MDA-MB-231 cell proliferation
50
Claims (4)
1. a Stigmasterol derivative is characterized in that having as shown in the formula structure shown in I or formula II:
The formula I
The group of the R representative in the formula I is: SO
2c
6h
5, COCH
3, COCH
2cl, COC
6h
5, CH
2cH
3, NO
2;
The formula II.
2. the application of Stigmasterol derivative claimed in claim 1 in the medicine of preparation treatment cancer.
3. a medicine that is used for the treatment of cancer, is characterized in that containing Stigmasterol derivative claimed in claim 1 and pharmaceutically acceptable auxiliary.
4. medicine according to claim 3, is characterized in that this medicine is injection, tablet, pill, capsule, suspension agent or emulsion.
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|---|---|---|---|
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ID=49733188
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Cited By (4)
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|---|---|---|---|---|
| CN106008648A (en) * | 2016-05-24 | 2016-10-12 | 贵州省中国科学院天然产物化学重点实验室 | Jiajiami'ning (C-21 steroid saponin) derivative as well as preparation method and application thereof |
| WO2018059241A1 (en) * | 2016-09-27 | 2018-04-05 | 广西久福生物科技有限公司 | Extract with detoxification pharmaceutical effect and preparation method therefor |
| CN110051674A (en) * | 2018-07-26 | 2019-07-26 | 中国人民解放军空军军医大学第一附属医院 | Purposes of the stigmasterol in the drug of preparation treatment gastric cancer |
| KR20220160900A (en) * | 2021-05-28 | 2022-12-06 | 국민대학교산학협력단 | Composition for preventing or treating ovarian cancer comprising stigmasterol |
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Application publication date: 20131218 |