CN113244410A - Preparation method of clathrate compound based on porous starch and used for increasing cannabidiol water solubility - Google Patents
Preparation method of clathrate compound based on porous starch and used for increasing cannabidiol water solubility Download PDFInfo
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- CN113244410A CN113244410A CN202110591756.8A CN202110591756A CN113244410A CN 113244410 A CN113244410 A CN 113244410A CN 202110591756 A CN202110591756 A CN 202110591756A CN 113244410 A CN113244410 A CN 113244410A
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- 229950011318 cannabidiol Drugs 0.000 title claims abstract description 82
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 title claims abstract description 67
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 title claims abstract description 67
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 title claims abstract description 67
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 title claims abstract description 57
- 229920002472 Starch Polymers 0.000 title claims abstract description 41
- 239000008107 starch Substances 0.000 title claims abstract description 41
- 235000019698 starch Nutrition 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
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- 238000010438 heat treatment Methods 0.000 claims abstract description 8
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- 238000009210 therapy by ultrasound Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003995 emulsifying agent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 5
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 5
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 5
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims 1
- 239000008347 soybean phospholipid Substances 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 abstract description 7
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 abstract description 7
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 abstract description 7
- 235000009120 camo Nutrition 0.000 abstract description 7
- 235000005607 chanvre indien Nutrition 0.000 abstract description 7
- 239000011487 hemp Substances 0.000 abstract description 7
- 229930014626 natural product Natural products 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 17
- 239000003814 drug Substances 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000218236 Cannabis Species 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
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- 230000000694 effects Effects 0.000 description 2
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- 239000011148 porous material Substances 0.000 description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 244000292604 Salvia columbariae Species 0.000 description 1
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- -1 agriculture Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 235000014167 chia Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
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- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
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- 230000004112 neuroprotection Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Abstract
The invention discloses a preparation method of a clathrate compound for increasing cannabidiol water solubility based on porous starch, which comprises the following steps: step 1, preparing a CBD nano system; step 2, preparing a porous starch-CBD system; step 3, placing the porous starch-CBD system prepared in the step 2 in a constant-temperature water bath magnetic stirrer for heating and stirring; and 4, centrifuging the solution system prepared in the step 3, and obtaining a precipitate which is the CBD clathrate compound based on the porous starch. The invention adopts the natural product CBD extracted from the low-price hemp and the inclusion compound prepared from the low-price and easy-to-prepare porous starch, thereby not only improving the utilization rate, but also controlling the low cost. Compared with original CBD, the water solubility of the clathrate compound prepared by the invention is obviously improved.
Description
Technical Field
The invention relates to a method for improving water solubility of a water-insoluble medicine, in particular to a preparation method of a clathrate compound for improving water solubility of Cannabidiol (CBD) based on porous starch.
Background
Cannabis may be considered the most controversial plant in society: it has important medical application and is a drug prohibited from being taken. Hemp, a species of cannabis, is an annual herb of the family morganiaceae, genus cannabis, originates in chia and has been a source of food and fiber for over three thousand years. Cannabidiol is a main active ingredient in hemp, and has been a research hotspot in the fields of food, medicine and health care products in recent years, but because cannabidiol is hardly dissolved in water and has low availability, the increase of the water solubility of CBD is more important for scholars at home and abroad in view of the background. Compared with common starch, the surface of the porous starch has a plurality of micropores, the medicine can be embedded in the porous starch through the adsorption effect, and the adsorption is very firm, so that the medicine is not easy to separate. The excellent adsorption capacity of the porous starch enables the porous starch to be widely applied to the industries of food, medicine, agriculture, cosmetics and the like.
Disclosure of Invention
In order to solve the main problem of low water solubility of cannabidiol in biological utilization at present, the invention provides a preparation method of a clathrate compound for increasing the water solubility of cannabidiol based on porous starch. The method adopts low-cost porous starch to prepare the CBD clathrate compound, so that the water solubility of the CBD clathrate compound can be improved, and the utilization rate and the commercial value of the CBD clathrate compound can also be improved.
The purpose of the invention is realized by the following technical scheme:
a preparation method of a clathrate compound based on porous starch and used for increasing cannabidiol water solubility comprises the following steps:
step 1, preparing a CBD nano system:
adding CBD into the solution for dissolving, then adding an emulsifier, and placing the mixture into a cell disruptor for ultrasonic treatment to obtain a CBD nano system, wherein: the solution is one of methanol, ethanol and acetone, and can completely dissolve CBD; the emulsifier is one of hydroxypropyl methyl cellulose, polyvinyl alcohol and soybean lecithin, so that the stability of a solution system is improved, and the embedding effect is improved; the ultrasonic treatment temperature is 20-30 ℃, and the ultrasonic treatment time is 30-60 min; in the CBD nano system, the content of CBD is 5-20 wt%, and the content of emulsifier is 5-10 wt%;
step 2, preparing a porous starch-CBD system:
adding porous starch into the CBD nano system obtained in the step 1, and carrying out ultrasonic treatment to obtain a porous starch-CBD system, wherein: the ultrasonic treatment time is 1-5 min; in the porous starch-CBD system, the content of porous starch is 20-90 wt%;
and 3, placing the porous starch-CBD system prepared in the step 2 in a constant-temperature water bath magnetic stirrer for heating and stirring, wherein: the stirring speed is 500-1000 r/min, the stirring time is 20-240 min, and the heating temperature is 20-50 ℃;
and 4, centrifuging the solution system prepared in the step 3 to obtain a precipitate, namely the CBD clathrate compound based on the porous starch, wherein: the centrifugal speed is 5000-10000 r/min.
Compared with the prior art, the invention has the following advantages:
1. the hemp is used as a high-yield, sustainable and environment-friendly crop, has strong vitality, has the characteristics of higher specific strength and specific modulus, high tensile strength, high modulus, low density and the like, and is compounded with the degradable polyester, so that the mechanical property of the degradable polyester is enhanced.
2. The CBD has no mental activity as a natural beneficial component in the hemp, has a series of characteristics of neuroprotection, pain relief, inflammation diminishing, cancer resistance and the like, and the porous starch has good adsorption performance and excellent biodegradability, has rich pores or cavities to fill the surface and the interior of the porous starch, can be prepared into an inclusion compound by embedding the medicine into the pores through adsorption by a stirring method, and enhances the water solubility and the bioavailability of the CBD.
3. The invention adopts the cheap and light biodegradable hemp fiber reinforced degradable polyester to prepare the completely degradable green composite material, thereby not only changing waste into valuable, but also reducing the cost and lightening the environmental pollution. The mechanical properties of the composite material prepared by the method are obviously improved compared with those of the degradable polyester.
4. The invention adopts the natural product CBD extracted from the low-price hemp and the inclusion compound prepared from the low-price and easy-to-prepare porous starch, thereby not only improving the utilization rate, but also controlling the low cost. Compared with original CBD, the water solubility of the clathrate compound prepared by the invention is obviously improved.
Detailed Description
The technical solutions of the present invention are further described below with reference to the following examples, but the present invention is not limited thereto, and any modifications or equivalent substitutions may be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Example 1:
in this example, a clathrate compound based on porous starch to increase cannabidiol water solubility was prepared as follows:
step 1, preparing a CBD nano system: CBD → solution dissolution → addition of emulsifier → ultrasonic treatment of a cell disruption instrument to obtain a CBD nano system. The concrete conditions are as follows: CBD5wt%, emulsifier 5wt%, ultrasonic temperature of 20 deg.C, ultrasonic time of 30 min. In the ultrasonic process, the added emulsifier is hydroxypropyl methyl cellulose, and the CBD dissolving solvent is methanol.
Step 2, preparing a porous starch-CBD system: and placing the porous starch in a CBD solution system, and performing ultrasonic treatment for 1min to obtain a porous starch-CBD system with the porous starch content of 45 wt%.
And 3, placing the system prepared in the step 2 in a constant-temperature water bath magnetic stirrer, and stirring for a certain time at a fixed revolution, wherein: the stirring speed is 500r/min, the stirring time is 60min, and the heating temperature is 20 ℃.
And 4, centrifuging the solution system prepared in the step 3 at 10000r/min, detecting the concentration of CBD in the supernatant to be the non-inclusion concentration, and drying the obtained precipitate to obtain the CBD inclusion compound based on the porous starch.
Example 2:
in this example, a clathrate compound based on porous starch to increase cannabidiol water solubility was prepared as follows:
step 1, preparing a CBD nano system: CBD → solution dissolution → addition of emulsifier → ultrasonic treatment of a cell disruption instrument to obtain a CBD nano system. The concrete conditions are as follows: 10% of CBD10wt%, 7% of emulsifier by weight, wherein the ultrasonic temperature is 20 ℃ and the ultrasonic time is 30 min. In the ultrasonic process, the added emulsifier is hydroxypropyl methyl cellulose, and the CBD dissolving solvent is methanol.
Step 2, preparing a porous starch-CBD system: and placing the porous starch in a CBD solution system, and performing ultrasonic treatment for 1min to obtain a porous starch-CBD system with the porous starch content of 60 wt%.
And 3, placing the system prepared in the step 2 in a constant-temperature water bath magnetic stirrer, and stirring for a certain time at a fixed revolution, wherein: the stirring speed is 500r/min, the stirring time is 120min, and the heating temperature is 25 ℃.
And 4, centrifuging the solution system prepared in the step 3 at 10000r/min, detecting the concentration of CBD in the supernatant to be the non-inclusion concentration, and drying the obtained precipitate to obtain the CBD inclusion compound based on the porous starch.
Example 3:
in this example, a clathrate compound based on porous starch to increase cannabidiol water solubility was prepared as follows:
step 1, preparing a CBD nano system: CBD → solution dissolution → addition of emulsifier → ultrasonic treatment of a cell disruption instrument to obtain a CBD nano system. The concrete conditions are as follows: 15% of CBD15wt%, 10% of emulsifier by weight, the ultrasonic temperature is 35 ℃, and the ultrasonic time is 30 min. In the ultrasonic process, the added emulsifier is hydroxypropyl methyl cellulose, and the CBD dissolving solvent is methanol.
Step 2, preparing a porous starch-CBD system: and placing the porous starch in a CBD solution system, and performing ultrasonic treatment for 1min to obtain a porous starch-CBD system with the porous starch content of 60 wt%.
And 3, placing the system prepared in the step 2 in a constant-temperature water bath magnetic stirrer, and stirring for a certain time at a fixed revolution, wherein: the stirring speed is 500r/min, the stirring time is 240min, and the heating temperature is 30 ℃.
And 4, centrifuging the solution system prepared in the step 3 at 10000r/min, detecting the concentration of CBD in the supernatant to be the non-inclusion concentration, and drying the obtained precipitate to obtain the CBD inclusion compound based on the porous starch.
Detecting the CBD inclusion compound based on the porous starch prepared in the embodiment 1-3, wherein a liquid chromatographic column used for detection is a reversed phase C18 column (250 mmx4.6mm, 5 mu m), and the column temperature is 30 ℃; the mobile phase is acetonitrile and 0.1% acetic acid water solution, the volume ratio is 75:25, the flow rate is 1.0mL/min, the detection wavelength is 210nm, and the injection volume is 10 muL in each detection. The results are shown in Table 1.
TABLE 1
As can be seen from Table 1, the water solubility of the clathrate compound prepared by the invention is obviously improved compared with that of original CBD.
Claims (7)
1. A preparation method of a clathrate compound based on porous starch for increasing cannabidiol water solubility is characterized by comprising the following steps:
step 1, preparing a CBD nano system:
adding CBD into the solution for dissolving, then adding an emulsifier, and placing the mixture into a cell disruption instrument for ultrasonic treatment to obtain a CBD nano system with the CBD content of 5-20 wt% and the emulsifier content of 5-10 wt%;
step 2, preparing a porous starch-CBD system:
adding porous starch into the CBD nano system obtained in the step (1), and performing ultrasonic treatment to obtain a porous starch-CBD system with the porous starch content of 20-90 wt%;
step 3, placing the porous starch-CBD system prepared in the step 2 in a constant-temperature water bath magnetic stirrer for heating and stirring;
and 4, centrifuging the solution system prepared in the step 3, and obtaining a precipitate which is the CBD clathrate compound based on the porous starch.
2. The method of claim 1, wherein the first step is performed by using one of methanol, ethanol and acetone as the solution.
3. The method of claim 1, wherein the emulsifier is one of hydroxypropyl methylcellulose, polyvinyl alcohol, and soybean phospholipids.
4. The preparation method of the clathrate compound based on porous starch for increasing cannabidiol water solubility, as claimed in claim 1, wherein in the first step, the ultrasonic treatment temperature is 20-30 ℃, and the ultrasonic treatment time is 30-60 min.
5. The method for preparing the clathrate compound based on porous starch and used for increasing the water solubility of cannabidiol as claimed in claim 1, wherein in the second step, the ultrasonic treatment time is 1-5 min.
6. The preparation method of the clathrate compound based on porous starch for increasing cannabidiol water solubility, as claimed in claim 1, wherein in the third step, the stirring speed is 500-1000 r/min, the stirring time is 20-240 min, and the heating temperature is 20-50 ℃.
7. The method for preparing a clathrate compound with increased cannabidiol water solubility based on porous starch as claimed in claim 1, characterised in that in step four the centrifugation speed is 5000-10000 r/min.
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