CN111228246A - Application and preparation method of terpene phenol - Google Patents
Application and preparation method of terpene phenol Download PDFInfo
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- CN111228246A CN111228246A CN202010135275.1A CN202010135275A CN111228246A CN 111228246 A CN111228246 A CN 111228246A CN 202010135275 A CN202010135275 A CN 202010135275A CN 111228246 A CN111228246 A CN 111228246A
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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Abstract
The invention discloses an application and a preparation method of terpene phenol, wherein a hemp plant inflorescence is extracted to obtain a crude extract, and then the crude extract is separated to obtain the terpene phenol.
Description
Technical Field
The invention relates to the technical field of biomedicine, and particularly relates to application and a preparation method of terpene phenol.
Background
The hemp plant is often used in the adjuvant treatment of certain cancers, aids, for appetite stimulation, pain relief, for relief of neurological symptoms such as glaucoma and epilepsy, migraine, and bipolar mood swings, for relief of nausea in chemotherapy patients. The biological activity of the genus cannabis is well known and with the discovery of the cannabinoids receptors, the relaxation of the laws governing the use of cannabis has led to the opportunity to explore the cannabis as a source of new therapeutic agents. There are also an increasing number of patients suffering from severe diseases such as cancer who seek natural drugs as an alternative or complementary therapy, and there is a continuing need for new treatments for cancer or other symptoms.
The incidence rate of cancer is gradually high due to different living habits, environmental factors and other reasons, the malignant tumor is a disease which is difficult to cure once being discovered in a late stage, and the cancer incidence rate is high and the cancer is difficult to cure at present, so the method has important significance for separating active ingredients in the hemp plants. Advances in the understanding of the "endogenous leprosy" system in the body have led to the potential that leprosy-based drugs may have the potential to treat diseases with advanced cancer.
At present, a terpene phenol can reduce inflammatory factors in inflammatory bowel disease; synoviocytes and chondrocytes apoptosis in rheumatoid arthritis; improving psoriasis and healing skin wound, etc. Among the widely used tumor cell inhibitors are cisplatin, paclitaxel, and gemcitabine.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide a novel application of terpene phenol, which has good anti-tumor cell proliferation activity and molecular formula of C21H32O2Molecular weight of 316.49, and its structural formula is:
the invention provides application of terpene phenol in formula (I) in preparing a tumor cell proliferation inhibitor.
The invention also provides a tumor cell proliferation inhibitor drug which comprises an active ingredient and pharmaceutically acceptable auxiliary materials, wherein the active ingredient comprises a compound shown in the formula (I).
The invention also provides the application of the terpene phenol in the formula (I) in preparing the medicine for treating the tumor diseases.
The invention also provides an anti-tumor medicament which comprises an active ingredient and pharmaceutically acceptable auxiliary materials, wherein the active ingredient comprises a compound shown in a formula (I).
Preferably, the tumor disease is liver cancer or lung cancer.
Preferably, the medicament comprises an effective dose of the compound shown in the formula (I).
Preferably, the medicine is an oral preparation or an injection preparation, and the oral preparation is one of dripping pills, tablets, capsules, granules or oral liquid; the injection preparation is selected from injection or powder injection.
The invention also provides a preparation method of the terpene phenol, which comprises the following steps:
(1) sequentially performing carbon dioxide supercritical extraction and ethanol extraction on the hemp plant inflorescence to obtain a crude extract;
(2) dissolving the crude extract, and separating by normal phase silica gel column chromatography, first reverse phase silica gel column chromatography, and second reverse phase silica gel column chromatography to obtain terpene phenol.
Preferably, the carbon dioxide supercritical extraction conditions are: pExtraction kettle＝20-30MPa，TExtraction kettle＝35-60℃；PSeparation kettle I＝8-11MPa，TSeparation kettle I＝35-65℃；PSeparation kettle II＝3-6MPa，TSeparation kettle II30-40 ℃; the usage amount of ethanol in the ethanol extraction is 15-25% of the weight of the hemp plant inflorescence, and the extraction time is 30-60 min.
Preferably, the crude extract is fully dissolved by petroleum ether; the normal phase silica gel column chromatography is prepared by mixing 100% of petroleum ether, petroleum ether: ethyl acetate 100: 1. petroleum ether: ethyl acetate 10: 1. performing gradient elution by using 100% of ethyl acetate as an eluent; performing gradient elution with 50-100% (v/v) methanol/water solution as eluent by the first-stage reverse phase silica gel column chromatography; the second-stage reverse phase silica gel column chromatography is carried out with gradient elution by using 60-80% (v/v) methanol/water solution as eluent.
The invention has the beneficial effects that: the terpene phenol prepared by the method has high purity, good stability and good biological activity, and cell experiments show that the terpene phenol has good anti-tumor cell proliferation activity, and particularly has obvious effect of inhibiting cell proliferation in liver cancer cells and lung cancer cells.
Drawings
FIG. 1 is a graph showing the effect of compound CBG on the survival rate of human hepatoma cells (HepG2) by MTT assay;
FIG. 2 shows the effect of compound CBG on the survival of human lung cancer cells (A549) by MTT method;
FIG. 3 shows the effect of compound CBG on the survival rate of human hepatoma cells (HepG2) by CCK8 method;
FIG. 4 shows the effect of CCK8 compound CBG on human lung cancer cell (A549) survival;
FIG. 5 shows a microscopic image of the cell colonies after treatment of human hepatoma cells (HepG2) with compound CBG;
FIG. 6 shows the effect of compound CBG on colony formation of human hepatoma cells (HepG 2);
FIG. 7 shows a microscopic image of cell colonies after treatment of human lung cancer cells (A549) with compound CBG;
FIG. 8 shows the effect of compound CBG on colony formation of human lung cancer cells (A549).
Detailed Description
To explain technical contents, structural features, and objects and effects of the technical solutions in detail, the following detailed description is given with reference to the accompanying drawings in conjunction with the embodiments.
Example 1
A preparation method of terpene phenol comprises the following steps:
(1) taking a hemp plant inflorescence as a raw material, crushing a dried sample, and extracting 500g of the crushed sample by using carbon dioxide supercritical extraction. The extraction conditions were: pExtraction kettle＝30MPa，TExtraction kettle＝45℃；PSeparation kettle I＝8MPa，TSeparation kettle I＝45℃；PSeparation kettle II＝6MPa，TSeparation kettle IIThe temperature is 35 ℃; adding 20 wt% ethanol as carrier, and extracting for 45 min. Extracting to obtain 100.533g of crude extract.
(2) Taking 50g of crude extract, fully dissolving the crude extract by using petroleum ether, carrying out normal phase silica gel column chromatography by using a Changzhou tritai medium-pressure rapid preparation chromatograph, and eluting 4 column volumes by using the petroleum ether with 100 percent, wherein the petroleum ether comprises the following components: ethyl acetate 100: 1 elute 20 column volumes, petroleum ether: ethyl acetate 10: eluting 10 column volumes with 1, eluting 100% ethyl acetate until the peak value of on-line detection is lower than 100mAU, and the flow rate is 80 mL/min. According to the thin layer tracing, merging part of ethyl acetate 100% elution parts, namely the eluent containing the target component to obtain a first-grade component containing the target compound; subjecting 5.6g of the first-stage component to self-filling reverse phase silica gel column chromatography, and gradient eluting with 50-100% (v/v) methanol/water solution as eluent at flow rate of 80 drops/min. According to the thin layer tracing, combining 70% and 80% of methanol elution parts, namely the eluent containing the target component, to obtain a secondary component containing the target compound; subjecting 1.3g of the second-stage component to self-filling reverse phase silica gel column chromatography, and gradient eluting with 60-80% (v/v) methanol/water solution as eluent at flow rate of 80 drops/min. According to the thin layer tracing, 70% of the elution part and 75% of the elution part of methanol, namely the elution liquid containing the target component, are merged to obtain a terpene phenol CBG 273 mg.
Example 2
Identification of antitumor activity of terpene phenol
Medicine preparation: a terpene phenol prepared in example 1.
(1) MTT colorimetric method for detecting influence of terpene phenol on tumor cell survival performance
Taking human liver cancer cells (HepG2) in a logarithmic growth phase, adjusting the number of the cells to 7000 per well by using a high-sugar medium (DMEM) culture medium, inoculating 100 mu L of each well into a 96-well plate, culturing in an incubator until the cells adhere to the wall, respectively preparing terpene phenol solutions with the concentrations of 20ug/ml and 40ug/ml by using DMSO as solvents, respectively adding 100 mu L of terpene phenol with the concentrations of 20ug/ml and 40ug/ml into experimental groups for treatment, adding DMSO with the same volume into blank groups, and acting for 24 hours under the culture medium; detecting cell survival rate with MTT reagent by using 20ug/ml antitumor drug cisplatin (DDP) as control, repeating for 3 times, and averaging;
as shown in FIG. 1, the survival rate of human hepatoma cells (HepG2) was lower with increasing concentration, i.e., the inhibition of the survival of human hepatoma cells (HepG2) by a terpene phenol was stronger; when the concentration is 40ug/ml, the inhibition effect is stronger than that of the antineoplastic drug cisplatin (DDP) with the dosage of 20 ug/ml.
Taking human lung cancer cells (A549) in logarithmic growth phase, using a DMEM culture medium, adjusting the cell concentration to 7000 cells per well, inoculating 100 mu L of each well into a 96-well plate, culturing in an incubator until the cells adhere to the wall, using 100 mu L of DMSO as a solvent to respectively prepare terpene phenol solutions with the concentrations of 20ug/ml and 40ug/ml, respectively adding the terpene phenol solutions with the prepared concentrations of 20ug/ml and 40ug/ml into experimental groups for treatment, adding 100 mu L of DMSO into blank groups, and acting for 24 hours under the culture medium; detecting cell survival rate with MTT reagent by using 20ug/ml antitumor drug cisplatin (DDP) as control, repeating for 3 times, and averaging;
as shown in fig. 2, the survival rate of the human lung cancer cell (a549) was lower as the concentration was increased, i.e., the inhibition effect of one terpene phenol on the survival of the human lung cancer cell (a549) was stronger; when the concentration is 40ug/ml, the inhibition effect is stronger than that of the antineoplastic drug cisplatin (DDP) with the dosage of 20 ug/ml.
(2) CKK8 cell proliferation toxicity detection method for detecting influence of terpene phenol on tumor cell survival performance
Taking human liver cancer cells (HepG2) in a logarithmic growth phase, adjusting the cell concentration to 7000 cells per well by using a DMEM culture medium, inoculating 100 mu L of each well into a 96-well plate in an incubator, culturing in the incubator at 37 ℃ until the cells adhere to the wall, respectively preparing terpene phenol solutions with the concentrations of 20ug/ml and 40ug/ml by using 100 mu L of DMSO as a solvent, respectively adding the terpene phenol with the prepared concentrations of 20ug/ml and 40ug/ml into an experimental group for treatment, adding 100 mu L of DMSO into a blank group, and acting for 24 hours under the culture medium; detecting cell survival rate with CCK8 kit with 20ug/ml antitumor drug cisplatin (DDP) as control, repeating for 3 times, and averaging;
as shown in FIG. 3, the survival rate of human hepatoma cells (HepG2) was lower with increasing concentration, i.e., the inhibition of the survival of human hepatoma cells (HepG2) by a terpene phenol was stronger; when the concentration is 40ug/ml, the inhibition effect is equivalent to that of the antitumor drug cisplatin (DDP) with the dose of 20 ug/ml.
Taking human lung cancer cells (A549) in logarithmic growth phase, using a DMEM culture medium, adjusting the cell concentration to 7000 cells per well, inoculating 100 mu L of each well into a 96-well plate, culturing in an incubator until the cells adhere to the wall, using 100 mu L of DMSO as a solvent to respectively prepare terpene phenol solutions with the concentrations of 20ug/ml and 40ug/ml, respectively adding the terpene phenol solutions with the prepared concentrations of 20ug/ml and 40ug/ml into experimental groups for treatment, adding 100 mu L of DMSO into blank groups, and acting for 24 hours under the culture medium; detecting cell survival rate with CCK8 kit with 20ug/ml antitumor drug cisplatin (DDP) as control, repeating for 3 times, and averaging;
as shown in fig. 4, the survival rate of the human lung cancer cell (a549) was lower as the concentration was increased, i.e., the inhibition effect of one terpene phenol on the survival of the human lung cancer cell (a549) was stronger; when the concentration is 40ug/ml, the inhibition effect is stronger than that of the antineoplastic drug cisplatin (DDP) with the dosage of 20 ug/ml.
(3) Cell clone colony forming method for detecting influence of terpene phenol on proliferation performance of tumor cells
Taking human liver cancer cells (HepG2) in a logarithmic growth phase, digesting the cells into single cells, inoculating the single cells to a 6-well plate, adding 350 cells in each well, adding a human 3ML DMEM culture medium, culturing the cells to an adherent state in an incubator, respectively preparing terpene phenol solutions with the concentrations of 20ug/ML and 40ug/ML by taking 100 mu L DMSO as a solvent, respectively adding the terpene phenol solutions with the concentrations of 20ug/ML and 40ug/ML into an experimental group, respectively treating the experimental group by adding the terpene phenol with the concentrations of 20ug/ML and 40ug/ML, adding 100 mu L DMSO into a blank group, replacing fresh culture medium and medicaments every 2-3 days, and continuously culturing for one week until macroscopic clones are formed; after each well is treated, a proper amount of 0.1% crystal violet is added for staining, then the staining solution is slowly washed away by running water, the cell is dried in the air, the clone number of the cell is counted, and the cell colony forming rate is calculated by taking a picture under a microscope (shown in figure 5). As shown in FIG. 6, the lower the colony formation rate of human hepatoma cells (HepG2) with increasing concentration, i.e., the stronger the inhibitory effect of a terpene phenol on the proliferation of human hepatoma cells (HepG 2).
Taking human lung cancer cells (A549) in logarithmic growth phase, digesting into single cells, inoculating the single cells to a 6-well plate, culturing the single cells to an adherent surface in an incubator by adding human 3ML DMEM culture medium, respectively preparing terpene phenol solutions with the concentrations of 20ug/ML and 40ug/ML by taking 100 mu L DMSO as a solvent, respectively adding the terpene phenol solutions with the concentrations of 20ug/ML and 40ug/ML into experimental groups for treatment, adding 100 mu L DMSO into blank groups, replacing fresh culture medium and medicament every 2-3 days, and continuously culturing for one week until macroscopic clones are formed; after each well is treated, a proper amount of 0.1% crystal violet is added for staining, then the staining solution is slowly washed away by running water, the cell is dried in the air, the clone number of the cell is counted, and the cell colony forming rate is calculated by taking a picture under a microscope (shown in figure 7). As shown in fig. 8, the lower the colony formation rate of human lung cancer cell (a549) with increasing concentration, i.e., the stronger the inhibitory effect of a terpene phenol on the proliferation performance of human lung cancer cell (a 549).
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or terminal that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or terminal. Without further limitation, an element defined by the phrases "comprising … …" or "comprising … …" does not exclude the presence of additional elements in a process, method, article, or terminal that comprises the element. Further, herein, "greater than," "less than," "more than," and the like are understood to exclude the present numbers; the terms "above", "below", "within" and the like are to be understood as including the number.
Although the embodiments have been described, once the basic inventive concept is obtained, other variations and modifications of these embodiments can be made by those skilled in the art, so that the above embodiments are only examples of the present invention, and not intended to limit the scope of the present invention, and all equivalent structures or equivalent processes using the contents of the present specification and drawings, or any other related technical fields, which are directly or indirectly applied thereto, are included in the scope of the present invention.
Claims (10)
1. An application of terpene phenol in preparing tumor cell proliferation inhibitor has a chemical structure shown in formula (I):
2. the tumor cell proliferation inhibitor medicine is characterized by comprising an active ingredient and pharmaceutically acceptable auxiliary materials, wherein the active ingredient comprises a compound shown in a formula (I).
3. The application of terpene phenol in preparing medicine for treating tumor diseases is shown in the formula (I):
4. an antitumor drug is characterized by comprising an active ingredient and pharmaceutically acceptable auxiliary materials, wherein the active ingredient comprises a compound shown as a formula (I).
5. The use according to claim 1 or 3, wherein the neoplastic disease is liver cancer or lung cancer.
6. The medicament of claim 2 or 4, wherein the medicament comprises an effective amount of the compound of formula (I).
7. The medicine according to claim 2 or 4, wherein the medicine is an oral preparation or an injection preparation, and the oral preparation is one of dripping pills, tablets, capsules, granules or oral liquid; the injection preparation is selected from injection or powder injection.
8. A preparation method of terpene phenol is characterized by comprising the following steps:
(1) sequentially performing carbon dioxide supercritical extraction and ethanol extraction on the hemp plant inflorescence to obtain a crude extract;
(2) dissolving the crude extract, and separating by normal phase silica gel column chromatography, first reverse phase silica gel column chromatography, and second reverse phase silica gel column chromatography to obtain terpene phenol.
9. The method of claim 8, wherein the supercritical carbon dioxide extraction conditions are: pExtraction kettle＝20-30MPa，TExtraction kettle＝35-60℃；PSeparation kettle I＝8-11MPa，TSeparation kettle I＝35-65℃；PSeparation kettle II＝3-6MPa，TSeparation kettle II30-40 ℃; the usage amount of ethanol in the ethanol extraction is 15-25% of the weight of the hemp plant inflorescence, and the extraction time is 30-60 min.
10. A process according to claim 8 or 9, comprising any one or more of the following features: fully dissolving the crude extract by using petroleum ether; secondly, the normal phase silica gel column chromatography is performed according to the following steps that 100% of petroleum ether, petroleum ether: ethyl acetate 100: 1. petroleum ether: ethyl acetate 10: 1. performing gradient elution by using 100% of ethyl acetate as an eluent; thirdly, performing gradient elution by using methanol/water solution as an eluent by the first-stage reverse phase silica gel column chromatography, preferably 50-100% (v/v) methanol/water solution; and fourthly, performing gradient elution by using methanol/water solution as an eluent by the two-stage reverse phase silica gel column chromatography, and preferably 60-80% (v/v) methanol/water solution.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574531A (en) * | 2020-05-15 | 2020-08-25 | 福建省中科生物股份有限公司 | Terpene phenolic compound NO85, and preparation method and application thereof |
| CN113149897A (en) * | 2021-03-24 | 2021-07-23 | 福建省中科生物股份有限公司 | 2, 6-substituted-4-oxyterpene phenol pyridine compound and preparation method and application thereof |
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| US20170143642A1 (en) * | 2014-06-27 | 2017-05-25 | Gw Pharma Limited | Active pharmaceutical ingredient (api) comprising cannabinoids for use in the treatment of cancer |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20170143642A1 (en) * | 2014-06-27 | 2017-05-25 | Gw Pharma Limited | Active pharmaceutical ingredient (api) comprising cannabinoids for use in the treatment of cancer |
Non-Patent Citations (1)
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| ENRICO D"ANIELLO等: "Identification and characterization of phytocannabinoids as novel dual PPARα/γ agonists by a computational and in vitro experimental approach", 《BBA - GENERAL SUBJECTS 》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574531A (en) * | 2020-05-15 | 2020-08-25 | 福建省中科生物股份有限公司 | Terpene phenolic compound NO85, and preparation method and application thereof |
| CN113149897A (en) * | 2021-03-24 | 2021-07-23 | 福建省中科生物股份有限公司 | 2, 6-substituted-4-oxyterpene phenol pyridine compound and preparation method and application thereof |
| CN113149897B (en) * | 2021-03-24 | 2023-10-31 | 福建省中科生物股份有限公司 | 2, 6-substituted-4-oxyterpene phenolic pyridine compound and preparation method and application thereof |
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