CN114573648A - Cannabinoid glycosides and methods of making the same - Google Patents

Cannabinoid glycosides and methods of making the same Download PDF

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CN114573648A
CN114573648A CN202011379107.3A CN202011379107A CN114573648A CN 114573648 A CN114573648 A CN 114573648A CN 202011379107 A CN202011379107 A CN 202011379107A CN 114573648 A CN114573648 A CN 114573648A
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cannabinoid
glycoside
group
reducing sugar
structural formula
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李慧龙
柳旭
孟世英
赵丽梅
高伟博
常坦然
李如彥
李庆中
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Yunnan Hanmeng Pharmaceutical Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/06—Benzopyran radicals

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Abstract

The invention provides a cannabinoid glycoside, which has a structural formula shown in the following formula (I), wherein G is glycosyl, and L is cannabinoid aglycone. The cannabinoid glycoside of the present invention is effective in improving water solubility, and the sugar group enhances cannabinoid absorption, resulting in a higher bioavailability of the cannabinoid glycoside and easier determination of G-L (I) for safety and pharmacological activity.

Description

Cannabinoid glycosides and methods of making the same
Technical Field
The invention relates to the field of drug synthesis, in particular to cannabinoid glycoside and a preparation method thereof.
Background
Cannabinoids are a characteristic component of cannabis in the plant industry, and phytocannabinoids have been used as therapeutic agents for various diseases and play similar roles in defense mechanisms of plants against pathogenic factors, such as Cannabidiol (CBD), one of the most important non-addictive components in plants, which has pharmacological activities of antispasmodic, antirheumatic arthritis, anxiolytic, etc., and can block adverse effects of Tetrahydrocannabinol (THC) on the human nervous system, and become a hot spot in drug development, and Epidiolex, the first active substance of which is cannabidiol, was approved by the U.S. Food and Drug Administration (FDA) in 2018. Cannabigerol (CBG) is a high affinity alpha2-an adrenergic receptor agonist and a medium affinity 5-HT1A receptor antagonist, CBG being a low affinity CB1 receptor antagonist and having antidepressant activity. Cannabichromene (CBC) has anti-inflammatory, antifungal and antiviral properties. Although cannabinoids have the above known beneficial effects, cannabinoids are highly hydrophobic, poorly water soluble and poorly bioavailable, which complicates their use in pharmaceutical formulations and thus limits their use.
To improve the water solubility of cannabinoids and thus increase the bioavailability, chinese patent application CN108136208A discloses cannabinoid glycoside prodrugs and methods of synthesis thereof, which prepare cannabinoid glycoside prodrugs by glycosyltransferase mediated glycosylation of cannabinoid molecules. However, according to the disclosure of the chinese patent application CN108136208A, the sugar group varies from one sugar to a plurality of sugars and the position cannot be controlled by the enzymatically synthesized cannabinoid glycoside.
The preparation of cannabinoids into water soluble cannabinoid products is another approach to improve the water solubility of cannabinoids and chinese patent application CN111135144A discloses water soluble cannabinoid products and methods of making the same by preparing cannabinoids into cannabinoid nanoemulsions to improve the water solubility of cannabinoids. However, according to the disclosure of the chinese patent application CN111135144A, the content of cannabinoid in water-soluble cannabinoid products is much lower than that of cannabinoid glycoside, and more encapsulating raw material is added, and the ingredients are relatively complex, which may present a risk of food safety.
In view of the shortcomings of the prior art cannabinoid products, there is a need to provide a single component cannabinoid product that can improve water solubility while ensuring cannabinoid content, and a method for preparing the same.
Disclosure of Invention
The invention aims to provide a cannabinoid glycoside which has precise quantity and position of glycosyl on the cannabinoid glycoside, single component and convenient safety investigation, and can effectively improve water solubility, thereby enhancing absorption and improving bioavailability.
The structural formula of the cannabinoid glycoside of the present invention is shown in formula (I) below:
G-L
(I)
wherein G is a glycosyl group and L is a cannabinoid aglycone.
In some embodiments, the glycosyl group of the invention can be a reducing glycosyl group, for example, the reducing glycosyl group can be a glucosyl group or a fructosyl group, and the like.
In some embodiments, the glycosyl groups of the invention have the structure:
Figure BDA0002807992940000021
in some embodiments, the cannabinoid aglycone of the invention may be Cannabidiol (CBD), Cannabidivarin (CBDV), Cannabiterpene (CBG), cannabidivarin terpene (CBGV), cannabichromene (CBC), cannabichromene (CBCV), Cannabinol (CBN), Cannabisubol (CBNV), 11-hydroxytetrahydrocannabinol (11-OH-THC), 11-hydroxytetrahydrocannabinol (11-OH-THCV) aglycone, having the following structure:
Figure BDA0002807992940000022
Figure BDA0002807992940000031
in some embodiments, the cannabinoid glycoside of the present invention can be a cannabinoid fructose glycoside, having the structural formula shown below in formula (II):
Figure BDA0002807992940000032
wherein L is a cannabinoid aglycone, for example, CBD, CBDV, CBG, CBGV, CBC, CBCV, CBN, CBNV, 11-OH-THC, 11-OH-THCV aglycone as described above.
In some embodiments, the cannabinoid glycoside of the present invention can be a cannabinoid glucose glycoside having a structural formula as shown in formula (III) below:
Figure BDA0002807992940000041
wherein L is a cannabinoid aglycone, for example, CBD, CBDV, CBG, CBGV, CBC, CBCV, CBN, CBNV, 11-OH-THC, 11-OH-THCV aglycone as described above.
In some embodiments, the cannabinoid glycoside of the present invention can be a glycoside having the following structural formula
Figure BDA0002807992940000042
It is another object of the present invention to provide a process for the preparation of cannabinoid glycosides comprising the steps of:
adding cannabinoid, reducing sugar or its derivative, and catalyst into reaction solvent, reacting under stirring, and performing column chromatography to obtain cannabinoid glycoside.
In some embodiments, the molar ratio of cannabinoid to reducing sugar or derivative thereof in the preparation process of the invention is 1:0.8 to 1:2.2, preferably 1:0.9 to 1:2.
In some embodiments, the mass to volume ratio (g: mL) of cannabinoid to reaction solvent in the preparation methods of the invention is from 1:3 to 1:10, preferably from 1:5 to 1: 8.
In some embodiments, the reducing sugar in the preparation method of the present invention may be glucose, fructose, or the like, and the derivative of the reducing sugar may be acetylglucose, acetylfructose, or the like.
In some embodiments, the reaction solvent in the preparation method of the present invention may be DMF, DMSO, dichloromethane, or the like.
In some embodiments, the catalyst in the preparation method of the present invention may be a lewis acid, for example, p-toluenesulfonic acid, boron trifluoride etherate, zinc chloride, ferric chloride, and the like.
In some embodiments, the solvent used for column chromatography in the preparation methods of the present invention is ethyl acetate: methanol 10:1 to 4:1(V: V), or ethyl acetate: ethanol is 10:1 to 3:1(V: V).
In some embodiments, the preparation method of the present invention is to subject the reaction to an oxygen removal operation with a solvent and a reagent before the reaction.
In some embodiments, the preparation method of the present invention comprises the steps of:
adding cannabinoid, reducing sugar and catalyst into reaction solvent, stirring until the solid is completely dissolved, heating to 100 deg.C-140 deg.C (preferably 110 deg.C-130 deg.C, more preferably 120 deg.C), maintaining the temperature, stirring, reacting for 8 hr-12 hr, directly lyophilizing to remove reaction solvent to obtain oily substance, dissolving with ethyl acetate or mixed solvent of ethyl acetate and alcohol, and performing column chromatography to obtain cannabinoid glycoside.
In some embodiments, the preparation method of the present invention comprises the steps of:
adding cannabinoid and reducing sugar derivatives into a reaction solvent under the protection of nitrogen, stirring until the solid is completely dissolved, cooling to-30 ℃ to-10 ℃ (preferably-20 ℃), adding a catalyst, keeping the nitrogen environment at a constant temperature, stirring for reaction for 0.5 hour to 2 hours, transferring a reaction solution into ice water after the reaction is finished, stirring until ice is completely melted, separating liquid, concentrating an organic phase, adding into a strong alkaline solution, refluxing for 3 hours to 12 hours, concentrating, adjusting the pH to be neutral, extracting, concentrating the organic phase, and performing column chromatography to obtain the cannabinoid glycoside.
The preparation method of the cannabinoid glucoside is simple to operate, high in practicability and good in industrial application condition, and provides a better way for utilization of the cannabinoid compound. The cannabinoid glycoside prepared by the method can effectively improve water solubility, and glycosyl can enhance the absorption of cannabinoid, so that the bioavailability of the cannabinoid glycoside is higher, and the safety and the pharmacological activity are easier to measure. In addition, compared with water-soluble cannabinoids, the cannabinoid glycoside of the invention has high content of cannabinoids, and has no food safety risk; compared with enzymatic synthesis of cannabinoid glycoside, the method has the advantages of precise quantity and position of glycosyl on the cannabinoid glycoside, single component, reduction of difficulty in post-treatment and purification, and convenience in safety investigation.
Drawings
FIG. 1 shows CBD glucoside prepared in example 1 of the present invention1HNMR spectrogram.
FIG. 2 is a liquid phase diagram of CBD.
FIG. 3 is a liquid phase diagram of p-toluenesulfonic acid.
FIG. 4 is a liquid phase diagram of CBD glucoside prepared in example 1 of the present invention.
Detailed Description
The following examples further illustrate the invention, but they are not to be construed as limiting or restricting the scope of the invention.
Reagent information:
Figure BDA0002807992940000061
other reagents used in the examples of the present invention were commercially available conventional reagents.
Experimental instrument information:
1. the invention uses a high performance liquid chromatograph Agilent 1260Infinity II to carry out purity determination, and the determination conditions are as follows:
taking an amino column as a chromatographic column; acetonitrile is used as a mobile phase A, water is used as a mobile phase B, and the ratio of A (%): b (%) (90: 10) isocratic elution; the detection wavelength was 210 nm.
Preparation of control solutions: accurately weighing CBD reference substance, adding ethanol (1:1) to obtain reference substance solution containing 0.1 mg/l ml.
Preparing a test solution: taking about 30mg of CBD glucoside sample, precisely weighing, placing in a 25ml measuring flask, adding 20ml of acetonitrile-water (1:1), carrying out ultrasonic treatment for 10 minutes, adding acetonitrile-water (1:1) to dilute to a scale, shaking, filtering by using a microporous filter membrane (0.45pm), and taking a subsequent filtrate.
The determination method comprises the following steps: respectively sucking 10 μ l of each of the reference solution and the sample solution, injecting into high performance phase chromatograph, and measuring.
2. The invention uses nuclear magnetic resonance apparatus to confirm the structure, and the measuring conditions are as follows:
DMSO-D6as deuterated solvent, Bruker AVANCE III HD 400HZ was used.
Example (b):
EXAMPLE 1 preparation of CBD glucoside
Figure BDA0002807992940000071
Under the protection of nitrogen, adding 25mL of DMSO, 5g of CBD, 3.15g of glucose and 0.5g of p-toluenesulfonic acid into a 100mL three-necked flask in sequence, stirring until all solids are dissolved, heating to 120 ℃, keeping the temperature for 10 hours, cooling to room temperature, directly freeze-drying the reaction solution to generate an oily substance, dissolving the oily substance with ethyl acetate, and then performing column chromatography (ethyl acetate: methanol is 10: 1-4: 1) to obtain yellow viscous CBD glucoside, wherein the yield is about 67%, the liquid-phase retention time of the CBD glucoside at room temperature is 5.1min, and a liquid-phase diagram is shown in figure 4,1the HNMR spectrum is shown in FIG. 1.
EXAMPLE 2 preparation of CBD fructosyl glycosides
Figure BDA0002807992940000072
Under the protection of nitrogen, 40mL of DMF, 5g of CBD, 5.7g of D-fructose and 0.5g of boron trifluoride ether are sequentially added into a 100mL three-necked flask, the mixture is stirred until all solids are dissolved, the temperature is raised to 120 ℃, the reaction is kept for 10 hours, the temperature is reduced to room temperature, the reaction solution is freeze-dried, an oily substance is generated, and the oily substance is dissolved by a mixed solution of ethyl acetate and methanol and then subjected to column chromatography (ethyl acetate: methanol is 10: 1-4: 1) to obtain light yellow viscous CBD fructosyl glucoside, wherein the yield is about 62%.
EXAMPLE 3 preparation of CBD glucoside
Figure BDA0002807992940000081
Under the protection of nitrogen, 50mL of dichloromethane, 5g of CBD and 5.6g of pentaacetylglucose are sequentially added into a 100mL three-necked flask, stirred until all solids are dissolved, cooled to-20 ℃, 2mL of boron trifluoride ether is added, the temperature is kept for 1 hour, the reaction solution is transferred into ice water (10g), stirred until all ice is melted, liquid is separated, and the organic phase is washed once again by saturated saline solution. Then concentrating, adding 20mL of 15% sodium methoxide methanol solution into the concentrate, refluxing for 4 hours, adjusting the pH to be neutral by using 10% hydrochloric acid, adding n-heptane for extraction for three times, concentrating an organic phase, performing column chromatography (ethyl acetate: methanol is 10: 1-4: 1) to obtain yellow viscous CBD glucoside, wherein the yield is about 52%, and a liquid-phase diagram is consistent with that in figure 4,1the HNMR spectra are consistent with FIG. 1.
Example 4 preparation of CBD fructosyl glycosides
Figure BDA0002807992940000091
Under the protection of nitrogen, 15mL of dichloromethane, 5g of CBD and 12g of penta-acetylfructose are sequentially added into a 100mL three-necked bottle, the mixture is stirred until all solids are dissolved, then the temperature is reduced to-20 ℃, 2mL of boron trifluoride ethyl ether is added, the mixture is subjected to heat preservation reaction for 1 hour, the reaction solution is transferred into ice water (10g), the mixture is stirred until all ice is melted, liquid is separated, and the organic phase is washed once again by saturated salt water. Then, the mixture was concentrated, and 20mL of a 15% sodium methoxide methanol solution was added to the concentrate, the mixture was refluxed for 4 hours, the pH of the mixture was adjusted to neutral with 10% hydrochloric acid, n-heptane was added to the mixture to extract the mixture three times, and the organic phase was concentrated and then subjected to column chromatography (ethyl acetate: methanol: 10:1 to 4:1) to obtain yellow viscous CBD fructosyl glycoside with a yield of about 42%.
EXAMPLE 5 preparation of CBDV glucoside
Figure BDA0002807992940000092
Under the protection of nitrogen, 35mL of DMSO, 4.55g of CBDV, 2.6g of glucose and 0.5g of p-toluenesulfonic acid are sequentially added into a 100mL three-necked bottle, the mixture is stirred until all solids are dissolved, the temperature is raised to 120 ℃, the reaction is kept for 10 hours, the temperature is reduced to room temperature, the reaction solution is directly freeze-dried, an oily substance is generated, and the oily substance is dissolved by ethyl acetate and then subjected to column chromatography (ethyl acetate: ethanol: 10: 1-3: 1) to obtain light yellow viscous CBDV glucoside, wherein the yield is about 70%.
EXAMPLE 6 preparation of CBG glucoside
Figure BDA0002807992940000101
Under the protection of nitrogen, sequentially adding 20mL of DMSO, 5g of CBG, 3.2g of glucose and 0.5g of p-toluenesulfonic acid into a 100mL three-necked flask, stirring until all solids are dissolved, heating to 120 ℃, carrying out heat preservation reaction for 10 hours, cooling to room temperature, directly freeze-drying the reaction solution to obtain an oily substance, dissolving the oily substance with ethyl acetate, and carrying out column chromatography (ethyl acetate: methanol: 10: 1-4: 1) to obtain light yellow oily CBG glucoside, wherein the yield is about 65%.
Example 7 preparation of CBC glucoside
Figure BDA0002807992940000102
Under the protection of nitrogen, 30mL of DMSO, 5g of CBC, 2.8g of glucose and 0.5g of p-toluenesulfonic acid are sequentially added into a 100mL three-necked bottle, the mixture is stirred until all solids are dissolved, the temperature is raised to 120 ℃, the reaction is kept for 10 hours, the temperature is reduced to room temperature, the reaction solution is directly freeze-dried, an oily substance is generated, the oily substance is dissolved by ethyl acetate, and then column chromatography is carried out (ethyl acetate: ethanol is 10: 1-3: 1) to obtain the CBC glucoside in an orange oily state, wherein the yield is about 60%.
EXAMPLE 8 preparation of CBN glucoside
Figure BDA0002807992940000111
Under the protection of nitrogen, adding 40mL of DMSO, 5g of CBN, 2.6g of glucose and 0.5g of p-toluenesulfonic acid into a 100mL three-neck flask in sequence, stirring until all solids are dissolved, heating to 120 ℃, carrying out heat preservation reaction for 10 hours, cooling to room temperature, directly freeze-drying the reaction solution to generate an oily substance, dissolving the oily substance with ethyl acetate, and carrying out column chromatography (ethyl acetate: methanol: 10: 1-4: 1) to obtain brown-yellow oily CBN glucose glucoside, wherein the yield is about 75%.

Claims (10)

1. A cannabinoid glycoside having the structural formula (I):
G-L
(I)
wherein G is a glycosyl group and L is a cannabinoid aglycone, wherein said glycosyl group is a reducing glycosyl group.
2. The cannabinoid glycoside according to claim 1, wherein the reducing sugar group is a glucose group or a fructose group.
3. The cannabinoid glycoside according to claim 1, wherein the sugar group has the structure:
Figure FDA0002807992930000011
4. the cannabinoid glycoside according to claim 1, wherein the cannabinoid aglycone has the structure:
Figure FDA0002807992930000012
Figure FDA0002807992930000021
5. the cannabinoid glycoside according to any of claims 1 to 4, wherein the cannabinoid glycoside is a cannabinoid fructose glycoside having the structural formula shown below in formula (II):
Figure FDA0002807992930000022
6. the cannabinoid glycoside according to any of claims 1 to 4, wherein the cannabinoid glycoside is a cannabinoid glucose glycoside having the structural formula shown in formula (III) below:
Figure FDA0002807992930000023
7. the cannabinoid glycoside according to claim 1, wherein the cannabinoid glycoside is a glycoside having the structural formula
Figure FDA0002807992930000031
8. A process for the preparation of a cannabinoid glycoside comprising the steps of:
adding cannabinoid, reducing sugar or its derivative, and catalyst into reaction solvent, reacting under stirring, and performing column chromatography to obtain cannabinoid glycoside.
9. The method according to claim 8, wherein the molar ratio of cannabinoid to reducing sugar or derivative thereof is 1: 0.8-1: 2.2, preferably 1: 0.9-1: 2; the mass volume ratio of the cannabinoid to the reaction solvent is 1: 3-1: 10, preferably 1: 5-1: 8.
10. The method of claim 8, wherein the reducing sugar is glucose or fructose, the derivative of the reducing sugar is acetylglucose or acetylfructose; the reaction solvent is DMF, DMSO or dichloromethane; the catalyst is a lewis acid, for example, p-toluenesulfonic acid, boron trifluoride etherate, zinc chloride.
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108136208A (en) * 2015-09-22 2018-06-08 活力生物制药有限公司 Cannboid glucosides prodrug and synthetic method

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108136208A (en) * 2015-09-22 2018-06-08 活力生物制药有限公司 Cannboid glucosides prodrug and synthetic method

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JINHUA WEI等: "Glycosynthase with Broad Substrate Specificity–an Efficient Biocatalyst for the Construction of Oligosaccharide Library", EUR.J.ORG.CHEM., pages 2414 *

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