CN114805382B - Sesquiterpene chromone compound, separation thereof and application thereof in preparation of pancreatic cancer resisting drugs - Google Patents
Sesquiterpene chromone compound, separation thereof and application thereof in preparation of pancreatic cancer resisting drugs Download PDFInfo
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Abstract
The invention discloses a structure and a separation method of sesquiterpene chromone compounds, and discovers that the sesquiterpene chromone compounds separated from Xinjiang asafetida have good pancreatic cancer resisting activity through an MTT (methyl thiazolyl tetrazolium) experiment, and can be used as an active ingredient for preparing medicines for treating pancreatic cancer. The structural formula of the sesquiterpene chromone compound is as follows:
Description
Technical Field
The invention relates to a natural sesquiterpene chromone compound and a separation method thereof, and also relates to the biological activity of the natural sesquiterpene chromone compound for resisting pancreatic cancer and application of the natural sesquiterpene chromone compound as an active substance for preparing an anti-pancreatic cancer drug, belonging to the field of natural pharmaceutical chemistry.
Background
Pancreatic cancer (Pancreatic cancer, PC) is highly invasive and fatal, and is one of the worst malignant tumors known to date. In recent years, the incidence rate of pancreatic cancer in China is in an ascending trend, the death rate of the pancreatic cancer is the first 10 of malignant tumors, and the survival rate of the pancreatic cancer in 5 years is only 10 percent. About 80% -85% of patients with pancreatic cancer cannot be surgically resected or have metastasized, and even patients with partial surgical resection still have poor prognosis, with only 10% -15% of patients being surgically controlled. Drug therapy is one of the main means of pancreatic cancer treatment, but the overall effective rate of the drug is less than 20% due to drug resistance and lack of drug specificity. In order to prolong the survival time of pancreatic cancer patients, development and search of safer and more effective pancreatic cancer chemotherapeutics are urgently needed.
Natural products are important sources of pharmaceuticals and play an important role in the discovery and development of new drugs. More than 60% of antitumor drugs are closely related to natural products. Although small molecule targeted drugs are dominant in cancer treatment. Therefore, natural active compounds are searched for, and novel anti-pancreatic cancer drugs are found, so that the search for efficient anti-pancreatic cancer drugs is facilitated. Xinjiang Ferula (Ferula sinica)Ferula sinkiangensisK.M. Shen) is herb of Ferula genus of Umbelliferae, and has a height of 0.5-1.5 m, and a strong odor of herba Alii Fistulosi and Bulbus Allii. The root is spindle-shaped or conical, thick and strong, and withered leaf sheath fibers remain on the root neck. Special shallot secreted by Ferula sinkiangensisThe oily gel resin with garlic-like odor is loaded by the traditional Chinese medicine of the past generation and pharmacopoeia of the people's republic of China, has the effects of removing food retention, relieving stuffiness and fullness and killing parasites, and can be used for treating diseases such as stomach diseases, dyspepsia, abdominal pain due to insect retention and the like.
Disclosure of Invention
The invention aims to provide a sesquiterpene chromone compound and a separation method thereof;
it is another object of the present invention to investigate the anti-pancreatic cancer activity of the above isolated sesquiterpene chromones for the preparation of a medicament for the treatment of anti-pancreatic cancer.
1. Separation of sesquiterpene chromones
The separation of the sesquiterpene chromone compound comprises the following steps:
(1) Extracting dried Ferula sinica root with methanol at room temperature for 3 times each for 7 days, mixing extractive solutions, and evaporating and concentrating until no alcohol smell exists to obtain total extractive solution;
(2) Dispersing the total extract with water, and extracting with petroleum ether (60-90 ℃), dichloromethane, ethyl acetate and n-butanol to obtain petroleum ether phase, dichloromethane phase, ethyl acetate phase, n-butanol phase and water phase;
(3) And (3) performing silica gel chromatographic separation on the ethyl acetate phase, eluting with petroleum ether-ethyl acetate (40:1-1:1), and sequentially obtaining 12 components FA-FL.
Subjecting component FH to silica gel column chromatography, eluting with dichloromethane-ethyl acetate (50:1) to obtain five components FH-1 to FH-5;
the fraction FH-1 was subjected to silica gel column chromatography and eluted with petroleum ether-ethyl acetate (10:1) to give 12 fractions FH-1-1 to FH-1-12.
Eluting components FH-1-7 with dichloromethane-ethyl acetate (60:1) to obtain eight components FH-1-7-1 to FH-1-7-8;
the components FH-1-7-5 were treated with methylene chloride-ethyl acetate (40:1) to give four components FH-1-7-5-1 to FH-1-7-5-4;
(4) HPLC (C) was used for component FH-1-7-5-1 18 ，MeOH/H 2 O=76/24, flow rate=4 ml/min) pureCarrying out chemical reaction to obtain a compound 1;
(5) Compound 1 was purified by Chiral HPLC (Chiral CD-Ph, petroleum ether: ethyl acetate=84/16, flow rate=3 ml/min) to give compound (+) -1, compound (-) -1 in sequence.
By optical rotation, UV spectrum, circular dichroism spectrum C, spectrum IR, infrared (KBr), hydrogen spectrum 1 H and carbon spectra 13 C. The compound (+) -1 and the compound (-) -1 separated by the above are analyzed by NMR high resolution mass spectrum HRESIMS, and 1H (400 MHz) and 13C (100 MHz) NMR data are shown in Table 1, and the structural formula is determined as follows:
compound (+) -1 and compound (-) -1 are colorless oils with the formula C 24 H 30 O 5 Mass spectral data(m/z399.2158, [M + H] + 399.2158 5 unsaturations can be deduced. 3424 -1 And 1723.9 cm -1 The strong infrared absorption at this point indicates the presence of hydroxyl and carbonyl groups. 1D NMR data indicated a 5,6, 8-trisubstituted benzene ring [ δH7.77 (D, J=8.5 Hz, H-5), 6.50 (dd, J=8.5, 2.16Hz, H-6), 6.37 (D, J=2.04 Hz, H-8) and δC129.5 (C-5), 110.3 (C-6), 162.4 (C-7), 103.6 (C-8), 114.39C-9), 160.69C-10]And two trisubstituted olefinic bonds [5.11 (d, j=9.76 hz, h-2, h-6') and δ C 126.1(C-2'), 129.3(C-6')]. Two H protons [ δH2 3.14 (d, J=10.5 Hz, H-3), 3.14 (d, J=10.52 Hz, H-10 ') and δC55.0 (C-3), 83.7 (C-10')]. The 1D NMR data also showed 24 carbon signals, including one carbonyl δC 191.34 (C-4), four methyl [ δH 1.19 (s, H3-13 '), 1.29 (s, H3-12'), 1.51 (s, H3-14 '), and 1.53 (s, H3-15')]。
The planar structures of compound (+) -1 and compound (-) -1 are further elucidated by comprehensive interpretation of 2D NMR spectra. For a pair of 1 H- 1 H COSYAnalysis of the spectrum indicated the presence of four related systems, namely CH (10 ') -CH (8'), CH (5) -CH (6), CH (9 ') -CH (1'), CH (6 ') -CH (5'). The correlation of HMBC data at H-5/C-4/C-7/C-9 and H-6/C-8/C-10, and H-8/C-6/C-10 indicates the presence of the A ring (as shown in FIG. 1), at H-3/C-/C-2'/C-2/C-1', H-2 '/C-4 '/C-15', H 3 -15'/C-3'/C-2'/C-4'、H 3 -14'/C-7'/C-8'、H-6'/C-14'/C-8'、H-4'/C-6'、H-10'/C-11'/C-8'、H 3 The correlation of-13 '/C-10'/C-11'/C-12' and H-12'/C-13'/C-11' indicates the presence of a B, C, D loop (as shown in FIG. 1). The absolute configuration was determined by ECD calculation (FIGS. 2-7).
2. Anti-pancreatic cancer activity of sesquiterpene chromones
The experiment was performed using human pancreatic cancer cells SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells, and the logarithmic growth phase of SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells were inoculated into 96-well plates (1X 10 per well) 4 Individual cells), after the cells adhere, respectively adding the compounds to be tested with the concentration range of 0.1-100 mu M gradient, culturing 72 h, and then adding 10 per holeµThe L CCK-8 solution was further cultured for 4 hours, the shaking was performed for 10 minutes, the absorbance value was measured by using an ELISA reader 450 nm, the proliferation inhibition effect of (+) -1 and (-) -1 of Sinkiang ferulic sesquiterpene chromones on SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells was detected by using an MTT method (FIG. 6), the cell viability was calculated based on the absorbance value, and the test compound IC was calculated 50 Values. Wherein paclitaxel (Taxol) is used as a positive control drug.
Table 2 shows the inhibition of pancreatic cancer SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells by the compounds (+) -1 and (-) -1. Wherein the compound (+) -1 inhibits the IC of SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells 50 The value is 11.77+ -1.83µM、6.12±0.52 µM、8.57±0.59 µM、2.24±0.83 µIC of M, compound (-) -1 inhibiting SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells 50 The value is 15.67+/-1.53µM、19.13±2.99 µM、14.57±0.65 µM、0.70±0.47 µM; the results show that the compoundsThe (+) -1 and the (-) -1 have remarkable proliferation inhibition effects on pancreatic cancer SW1990 cells, CFPAC-1 cells, capan-2 cells and PANC-1 cells, and the compounds (+) -1 and (-) -1 can obviously inhibit proliferation of pancreatic cancer cells, have potential effect on resisting pancreatic cancer, have potential of developing pancreatic cancer therapeutic drugs, and can be used as active ingredients for preparing the pancreatic cancer resisting drugs. The preparation method comprises the steps of taking the ferula sinkiangensis sesquiterpene chromone compound as an active component, and preparing the ferula sinkiangensis sesquiterpene chromone compound into an oral preparation or an injection by using pharmaceutically or physiologically acceptable auxiliary materials and a conventional preparation process. The oral preparation is powder, granule, capsule, soft capsule, powder, pill, tablet, and oral liquid.
Drawings
FIG. 1 shows the compound (+) -1, compound (-) -1 1 H -1 H COSY (black bolded) and HMBC (black arrow).
FIG. 2 shows the absolute configuration of compound (+) -1.
FIG. 3 is an ECD spectrum of compound (-) -1.
FIG. 4 is a CD spectrum of compound (-) -1.
FIG. 5 shows the absolute configuration of compound (+) -1.
FIG. 6 is an ECD spectrum of compound (+) -1.
FIG. 7 is a CD spectrum of compound (+) -1.
FIG. 8 shows that compounds (+) -1 and (-) -1 inhibit pancreatic cancer cell viability.
Detailed Description
(1) Extracting dried Ferula sinica root with methanol at room temperature for 3 times each for 7 days, mixing extractive solutions, and evaporating and concentrating until no alcohol smell exists to obtain total extract;
(2) Dispersing and dissolving the total extract with water, and extracting with petroleum ether, dimethyl chloride, ethyl acetate and n-butanol to obtain petroleum ether phase, dichloromethane phase, ethyl acetate phase, n-butanol phase and water phase;
(3) The ethyl acetate phase (260 g) is chromatographed on a silica gel column, eluting with petroleum ether to ethyl acetate (petroleum ether to ethyl acetate volume ratio is 40:1, 30:1, 20:1, 10:1, 8:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1) in sequence to obtain 12 components FA-FL in sequence;
subjecting component FH (61.3 g) to silica gel column chromatography, eluting with dichloromethane: ethyl acetate (50:1), to sequentially obtain five components FH-1 to FH-5;
subjecting component FH-1 (14.05 g) to silica gel column chromatography, eluting with petroleum ether and ethyl acetate (10:1) to obtain 12 components FH-1-1 to FH-1-12 in sequence;
eluting component FH-1-7 (393.6 mg) with dichloromethane to ethyl acetate (60:1) to obtain eight components FH-1-7-1 to FH-1-7-8;
the four components FH-1-7-5-1 to FH-1-7-5-4 were obtained from the components FH-1-7-5 (67 mg) with methylene chloride and ethyl acetate (40:1);
(4) HPLC (C) was used for component FH-1-7-5-1 (24 mg) 18 ，MeOH/H 2 O=76/24, flow rate=4 ml/min) to give compound 1 (4 mg, t R = 65.052 min）；
(5) Purification of compound 1 using Chiral HPLC (Chiral CD-Ph, petroleum ether: ethyl acetate=84/16, flow rate=3 ml/min) gave compound (+) -1 (1 mg, t R = 26.180 min) and compound (-) -1 (0.9 mg, t R =31.917 min)。
Compound [ (±) -1]: white oil; mp 218-221℃, UV (CH) 3 CN) λmax (log ε) 204(3.131)nm, 274(2.356) nm; IR (KBr) ν max = 3424, 2926.9, 1723.9, 1612.2, 1463.6, 1272.3, 1272.3, 1111.5, 1022.5, 1000.8, 972.0, 973.7 cm −1 ; 1 H NMR 13 The C NMR data are shown in Table 1, compound [ (. + -.) -1]Mass spectrum M/z 399.2158 [ M+H ]] + (C 24 H 30 O 5 , 399.2158)。
(+) -1: white oil;
+52.381° (c 0.1, CH 3 OH); ECD (CH 3 OH) λmax (Δε): 207(Δε -38.385), 257 (Δε -2.98), 268 (Δε -4.96), 301 (Δε 6.35), 328 (Δε -1.44) nm。
(-) -1: white oil;
-48.531° (c 0.1, CH 3 OH); ECD (CH 3 OH)λmax (Δε): 208 (Δε 33.67), 249 (Δε 0.77), 271 (Δε 3.67), 300 (Δε -5.54), 327(Δε 0.96) nm。
Claims (10)
1. a sesquiterpene chromone compound has the structural formula as follows:
2. the method for separating sesquiterpene chromone compounds according to claim 1, comprising the steps of:
(1) Extracting dried Ferula sinica root with methanol at room temperature for 3 times each for 7 days, mixing extractive solutions, and evaporating and concentrating until no alcohol smell exists to obtain total extractive solution;
(2) Dispersing the total extract with water, and extracting with petroleum ether, dichloromethane, ethyl acetate and n-butanol at 60-90 ℃ to obtain petroleum ether phase, dichloromethane phase, ethyl acetate phase, n-butanol phase and water phase;
(3) Separating ethyl acetate phase by silica gel chromatography, eluting with petroleum ether-ethyl acetate, and sequentially obtaining 12 components FA-FL;
subjecting component FH to silica gel column chromatography, eluting with dichloromethane-ethyl acetate to obtain five components FH-1 to FH-5;
subjecting component FH-1 to silica gel column chromatography, eluting with petroleum ether-ethyl acetate to obtain 12 components FH-1-1 to FH-1-12;
eluting the components FH-1-7 with dichloromethane-ethyl acetate to obtain eight components FH-1-7-1 to FH-1-7-8;
the components FH-1-7-5 were treated with methylene chloride-ethyl acetate to give four components FH-1-7-5-1 to FH-1-7-5-4;
(4) Purification of component FH-1-7-5-1 by HPLC gave Compound 1; HPLC purification conditions: c (C) 18 ，MeOH/H 2 O=76/24, flow rate=4 ml/min;
(5) Purifying the compound 1 by chiral HPLC to obtain a compound (+) -1 and a compound (-) -1 in sequence; chiral HPLC purification conditions: chiral CD-Ph, petroleum ether ethyl acetate=84/16, flow rate=3 ml/min.
3. The method for separating sesquiterpene chromone compounds according to claim 2, wherein: in the eluent petroleum ether-ethyl acetate of the ethyl acetate phase in the step (3), the volume ratio of petroleum ether to ethyl acetate is 40:1-1:1.
4. The method for separating sesquiterpene chromone compounds according to claim 2, wherein: in the eluent dichloromethane-ethyl acetate of the component FH in the step (3), the volume ratio of dichloromethane to ethyl acetate is 50:1.
5. The method for separating a hemiterpene chromone compound according to claim 2, wherein: in the eluent petroleum ether-ethyl acetate of the FH-1 component in the step (3), the volume ratio of petroleum ether to ethyl acetate is 10:1.
6. The method for separating sesquiterpene chromone compounds according to claim 2, wherein: in the eluent dichloromethane-ethyl acetate of the component FH-1-7 in the step (3), the volume ratio of dichloromethane to ethyl acetate is 60:1.
7. The method for separating sesquiterpene chromone compounds according to claim 2, wherein: in the eluent dichloromethane-ethyl acetate of the component FH-1-7-5 in the step (3), the volume ratio of dichloromethane to ethyl acetate is 40:1.
8. The use of a sesquiterpene chromone compound according to claim 1 for preparing an anti-pancreatic cancer medicament.
9. The use of the sesquiterpene chromones according to claim 8 for preparing an anti-pancreatic cancer drug, wherein: the sesquiterpene chromone compound is used as an active component, and is prepared into an oral preparation or an injection by using pharmaceutically or physiologically acceptable auxiliary materials and the preparation process of a conventional pharmaceutical preparation.
10. The use of the sesquiterpene chromones according to claim 9 for preparing an anti-pancreatic cancer drug, characterized in that: the oral preparation is powder, granule, capsule, soft capsule, powder, pill, tablet, and oral liquid.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009122447A1 (en) * | 2008-03-31 | 2009-10-08 | Council Of Scientific & Industrial Research | Semi-synthetic sesquiterpene lactone parthenin compound useful for cytotoxicity against cancer cell lines and anticander agent |
| CN104447655A (en) * | 2014-12-05 | 2015-03-25 | 沈阳药科大学 | Novel sesquiterpene coumarins in ferula sinkiangensis K.M.Shen as well as preparation methods and medical applications of novel sesquiterpene coumarins |
| CN114014759A (en) * | 2021-11-12 | 2022-02-08 | 中国科学院兰州化学物理研究所 | Triterpene compound with pancreatic cancer cell line proliferation inhibiting effect and preparation and application thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009122447A1 (en) * | 2008-03-31 | 2009-10-08 | Council Of Scientific & Industrial Research | Semi-synthetic sesquiterpene lactone parthenin compound useful for cytotoxicity against cancer cell lines and anticander agent |
| CN104447655A (en) * | 2014-12-05 | 2015-03-25 | 沈阳药科大学 | Novel sesquiterpene coumarins in ferula sinkiangensis K.M.Shen as well as preparation methods and medical applications of novel sesquiterpene coumarins |
| CN114014759A (en) * | 2021-11-12 | 2022-02-08 | 中国科学院兰州化学物理研究所 | Triterpene compound with pancreatic cancer cell line proliferation inhibiting effect and preparation and application thereof |
Non-Patent Citations (1)
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| Rearrangement-Driven Molecular Diversity: Synthesis of Functionalized Pyrones, Orthoesters, and Xanthones from Spiroketals;Maddali L. N. Rao et al.;Organic Letters;第23卷;8668-8672 * |
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