CN111122744A - Method for detecting content of one or more cannabinoids in industrial hemp extract by using HPLC - Google Patents
Method for detecting content of one or more cannabinoids in industrial hemp extract by using HPLC Download PDFInfo
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Abstract
The invention relates to the technical field of detection, in particular to a method for detecting the content of one or more cannabinoids in an industrial hemp extract by using HPLC (high performance liquid chromatography). The method uses methanol to extract cannabinoids from industrial hemp extract by ultrasonic wave, and High Performance Liquid Chromatography (HPLC) to detect. The content of one or more cannabinoids in the industrial hemp extract is obtained quantitatively by adopting retention time qualitative method and external standard method. The method is simple to operate and good in stability, and can be used for quickly and accurately quantifying various cannabinoids in the industrial hemp extract.
Description
Technical Field
The invention relates to the technical field of detection, in particular to a method for detecting the content of one or more cannabinoids in an industrial hemp extract by using HPLC (high performance liquid chromatography).
Background
Industrial Hemp (Hemp), which refers to Hemp with a THC (tetrahydrocannabinol) content of less than 0.3%, is becoming a global hotspot. The main active ingredients in industrial cannabis are cannabinoids including Cannabinol (CBN), Tetrahydrocannabinol (THC), Cannabidiol (CBD), sub-Cannabidiol (CBDV), etc., which can be mainly used for anti-epilepsy, anti-oxidation, anti-tumor, etc.
The CBD has no hallucinogenic effect, can reduce or offset the hallucinogenic and addictive properties of the other chemical component THC in the hemp, and has great application value in the aspects of reducing inflammation, pain, anxiety, mental diseases, epilepsy and the like. At present, CBD products are very popular in European and American countries and are popular health care nutriments. One of the most popular products is CBD oil, also known as CBD tincture. CBD oil contains high concentration of CBD, and is prepared by extracting CBD from leaves and stems of industrial hemp, and diluting with carrier oil (such as coconut oil or hemp seed oil), and is a thick plant extract. Whereas industrial cannabis full spectrum (broad spectrum) oils are extracts of industrial cannabis without further purification and isolation, and contain, in addition to CBD, other cannabinoids (such as CBN, CBG, CBDV, etc., sometimes with small amounts of THC), terpenes and aromatic compounds. Industrial hemp full spectrum (broad spectrum) oils are generally viscous, dark in color, and have the taste of hemp plants.
The content of various cannabinoids, especially CBD, in CBD oil or industrial cannabis full spectrum (broad spectrum) oil directly affects its product quality. The monitoring of the content of various cannabinoids in the industrial hemp extraction process is very important for the quality control of products, and relevant literature reports of a detection method of the content of cannabinoids in CBD oil or industrial hemp full spectrum (broad spectrum) oil are not seen at present, so that the establishment of a set of efficient, accurate and suitable method for the content of various cannabinoids in intermediate products and final products in the industrial hemp extraction process is necessary.
Disclosure of Invention
The content of one or more cannabinoids in the industrial hemp extract is extracted by methanol ultrasonic, the content is detected by a High Performance Liquid Chromatograph (HPLC), the retention time is qualitative, and the content is quantified by an external standard method, so that the content of one or more cannabinoids in the industrial hemp extract can be accurately and rapidly detected.
In order to achieve the purpose, the technical scheme of the invention is as follows:
the invention provides a method for detecting the content of one or more cannabinoids in an industrial cannabis extract by using HPLC (high performance liquid chromatography). The method comprises the following steps:
① preprocessing the sample by accurately weighing industrial hemp extract, adding organic solvent, ultrasonic extracting, standing, and filtering with membrane to obtain sample processing solution.
② Standard working solution preparation method comprises preparing standard reference solutions of cannabinoid with different concentration gradients.
③ High Performance Liquid Chromatography (HPLC) method comprises detecting standard working solution and sample treatment solution by HPLC, regression analyzing the corresponding concentration with the peak area of the standard working solution target substance to obtain standard curve, detecting the prepared sample treatment solution to determine whether the peak appears at the peak appearing time of the target substance, measuring the peak area of the detected target substance, substituting into the standard curve to obtain the concentration of the component to be detected in the sample, calculating to obtain the content, and detecting after dilution if the concentration of the sample treatment solution exceeds the concentration range of the standard working solution.
The High Performance Liquid Chromatography (HPLC) conditions were as follows: the mobile phase comprises acetonitrile and water, and the proportion of the acetonitrile to the water is 65%: 35 percent, isocratic elution with the flow rate of 1 mL/min; the sample injection amount is 10 uL; the column temperature is 30 ℃; the detector detection wavelength is 220 nm.
Further, the industrial hemp extract in step ① includes crude industrial hemp extract, CBD oil, and full spectrum (broad spectrum) industrial hemp oil.
The preparation method of the cannabis extract comprises the following steps:
① extracting, drying and crushing the leaves of industrial hemp, and extracting with supercritical carbon dioxide to obtain a crude extract, wherein the extraction temperature is 35-60 ℃, the extraction kettle pressure is 15-30 MPa, the extraction time is 0.5-3 hours, the analysis kettle temperature is 35-50 ℃, and the analysis pressure is 1-15 MPa.
② separating and purifying by filling silica gel into chromatographic column, loading sample (extract) by dry or wet method, eluting with mobile phase, separating out cannabinoids, collecting by stages, concentrating, and diluting with carrier oil to obtain final product.
The mesh number of the silica gel is 60-400 meshes, and the mobile phase can adopt n-hexane-ethyl acetate, petroleum ether-ethyl acetate, n-hexane-dichloromethane, petroleum ether-dichloromethane or a mixed solvent of a plurality of solvents; the chromatography mode can adopt normal pressure or pressurization; the elution mode can adopt isocratic elution or gradient elution; and concentrating the eluent by stages at the concentration temperature of 35-60 ℃.
Further, in step ①, the organic solvent is chromatographically pure methanol, the ratio of the hemp extract to the methanol volume is 1: 50, the ultrasonic time is 30min, the ultrasonic power is 250W, the working frequency is 40kHz, the standing time is 30min, and the filter membrane is a 0.22 μm organic needle filter membrane.
Further, in step ②, the cannabinoids include one or more of Cannabidivarin (CBDV), Cannabigerol (CBG), Cannabidiol (CBD), Cannabinol (CBN), Tetrahydrocannabinol (THC), and cannabichromene (CBC).
Further, the standard control working solution is prepared in step ② by diluting several cannabinoid standard controls purchased from Sigma company with chromatographically pure methanol to a series of standard working solutions having a concentration range of 1 μ g/mL to 100 μ g/mL, respectively.
Further, the brand model of the high performance liquid chromatograph is Agilent 1260; acetonitrile of a mobile phase is chromatographic pure, and water is deionized water; the chromatographic column is Agilent ZORBAX Eclipse Plus C18; the detector is a diode array detector (DAD detector for short).
The invention has the advantages that:
① the invention establishes a method for detecting the content of one or more cannabinoids in the industrial hemp flower and leaf extract by using HPLC, can carry out qualitative and quantitative analysis on one or more of CBDV, CBG, CBD, CBN, THC and CBC in the industrial hemp extract, and provides scientific basis for accurate judgment and rapid detection of the content and the content of the cannabinoids in the industrial hemp extract.
② the invention uses HPLC to detect one or more cannabinoid substances in the hemp flower and leaf extract, so that the qualitative and quantitative determination of one or more of CBDV, CBG, CBD, CBN, THC and CBC can be carried out rapidly and accurately under the same sample treatment.
Drawings
FIG. 1 HPLC profile of CBDV standard control.
FIG. 2 CBG Standard control HPLC profile.
FIG. 3 CBD Standard control HPLC profile.
FIG. 4 HPLC profile of CBN standard control.
FIG. 5 HPLC profile of THC standard control.
FIG. 6 CBC Standard control HPLC profile.
FIG. 7 HPLC chromatogram of sample treatment solution.
Detailed Description
The following examples are merely illustrative of the present invention and do not limit the scope of the present invention in any way. It will be apparent to those skilled in the art that equivalent embodiments or modifications without departing from the technical spirit of the present invention are within the scope of the present invention.
Examples detection of full spectrum (broad spectrum) oil from industrial cannabis
Extraction of industrial hemp full spectrum (broad spectrum) oil:
① drying and pulverizing industrial hemp flower and leaf, extracting with supercritical carbon dioxide to obtain crude extract, wherein the extraction temperature is 50 deg.C, the extraction kettle pressure is 20MPa, the extraction time is 2 hr, the desorption kettle temperature is 40 deg.C, and the desorption pressure is 10 MPa.
② separating and purifying, dissolving the crude extract with 3 times of n-hexane, adding 200 mesh silica gel according to the material ratio of 2:1, drying, loading by dry method, packing 200 mesh silica gel into column, eluting with n-hexane and ethyl acetate (8: 1), collecting mobile phase containing cannabinoid, and vacuum concentrating under reduced pressure to remove solvent to obtain industrial hemp full spectrum (broad spectrum) oil.
Pretreatment of a sample: accurately weighing 0.2g (accurate to 0.0001 g) of industrial hemp full spectrum (broad spectrum) oil, adding 10mL of methanol, ultrasonically extracting for 30min, standing for 30min, and filtering with 0.22 μm organic needle filter membrane to obtain sample treatment solution.
Preparation of standard working solution: CBDV, CBG, CBD, CBN, THC, CBC standard reference substances purchased from sigma company are respectively diluted by chromatographic grade methanol to a series of standard working solutions with the concentration ranging from 1 mug/mL to 100 mug/mL.
Determination by high performance liquid chromatography (HPLC method): detecting the standard working solution and the sample treatment solution by using HPLC (high performance liquid chromatography), wherein the determination method is to perform regression analysis on the corresponding concentration of a target object of the standard working solution by using the chromatographic peak area of the target object to obtain a standard curve; determining the prepared sample treatment solution, confirming whether a peak appears at the peak appearing time of the target object, measuring the chromatographic peak area of the detected target object, substituting the chromatographic peak area into a standard curve to obtain the concentration of the component to be detected in the sample, and further calculating the content of the component to be detected; and if the concentration of the sample treatment solution exceeds the concentration range of the standard working solution, diluting and detecting.
The High Performance Liquid Chromatography (HPLC) brand number is Agilent 1260 and the conditions are as follows: the mobile phase is acetonitrile and water, the acetonitrile is chromatographic pure, the water is deionized water, and the proportion of the acetonitrile to the water is 65%: 35 percent, isocratic elution with the flow rate of 1 mL/min; the sample injection amount is 10 uL; the chromatographic column is Agilent ZORBAX Eclipse Plus C18, and the column temperature is 30 ℃; the detector is a wavelength diode array detector (DAD detector for short) with a detection wavelength of 220 nm.
The peak time and standard curve for each standard were as follows:
CBDV peak time: 7.4min, standard curve: y =45.7738X +1.0055, R =0.99994, R2=0.99987。
CBG peak time: 13.2min, standard curve: y =44.9911X-4.9173, R =0.99951, R2=0.99902。
CBD peak time: 13.8min, standard curve: y =41.8399+5.0491, R =0.99989, R2=0.99978。
CBN peak-off time: 22.1min, standard curve: y =91.2243X-71.0329, R =0.99813, R2=0.99627。
THC peak time: 29.9min, standard curve: y =40.6303X +12.1413, R =0.99974, R2=0.99949。
CBC peak out time: 41.3min, standard curve: y =39.2107X +0.0623, R =0.99985, R2=0.99970。
The results of the sample tests are shown in Table 1.
TABLE 1 results of sample testing in examples
| Substance(s) | CBDV | CBG | CBD | CBN | THC | CBC |
| Content (%) | 25.3 | 2.18 | 47.8 | N.D | N.D | N.D |
Remarking: n.d indicates no detection.
Experimental example repeatability experiment
Pure CBD oil samples were prepared and processed as per the examples. The same sample was taken as 6 replicates, the procedure was run in parallel for three days and the relative standard deviation between the replicates was calculated. The results are shown in Table 2, and the intra-day RSD and the inter-day RSD of the peak area of the target CBD are both less than 2%, so that the requirement on repeatability can be met.
TABLE 2 results of the repeatability experiments
Claims (10)
1. A method for detecting the content of one or more cannabinoids in industrial cannabis extract by HPLC is characterized by comprising the following steps:
(1) pretreatment of a sample: accurately weighing industrial hemp flower and leaf extract, adding an organic solvent, carrying out ultrasonic extraction, standing, and filtering with a membrane to obtain a sample treatment solution;
(2) preparation of standard working solution: preparing standard reference solutions of various cannabinoids with different concentration gradients;
(3) determination by high performance liquid chromatography (HPLC method): detecting the standard working solution and the sample treatment solution by using HPLC (high performance liquid chromatography), wherein the determination method is to perform regression analysis on the corresponding concentration of a target object of the standard working solution by using the chromatographic peak area of the target object to obtain a standard curve; determining the prepared sample treatment solution, confirming whether a peak appears at the peak appearing time of the target object, measuring the chromatographic peak area of the detected target object, substituting the chromatographic peak area into a standard curve to obtain the concentration of the component to be detected in the sample, and further calculating the content of the component to be detected; if the concentration of the sample treatment solution exceeds the concentration range of the standard working solution, diluting and detecting;
the High Performance Liquid Chromatography (HPLC) conditions were as follows: the mobile phase is acetonitrile (chromatographic purity) and water (deionized water), and the proportion of the acetonitrile to the water is 65%: 35 percent, isocratic elution with the flow rate of 1 mL/min; the sample injection amount is 10 uL; the column temperature is 30 ℃; the detector detection wavelength is 220 nm.
2. The method for detecting the content of one or more cannabinoids in industrial hemp extracts by HPLC as claimed in claim 1, wherein the industrial hemp extract comprises crude industrial hemp extract, CBD oil, full spectrum (broad spectrum) oil of industrial hemp.
3. The method of claim 1, wherein the cannabis extract is prepared by the following steps:
(1) extraction: drying and crushing the flowers and leaves of industrial hemp, and extracting by using supercritical carbon dioxide to obtain a crude extract; the pressure of the extraction kettle is 15-30 MPa, the extraction temperature is 35-60 ℃, and the extraction time is 0.5-3 hours; the temperature of the resolution kettle is 35-50 ℃, and the resolution pressure is 1-15 MPa;
(2) separation and purification: loading silica gel into the chromatographic column, loading sample (i.e. extract) by dry method or wet method, eluting with mobile phase, separating out cannabinoids, collecting by stages, concentrating, and diluting with carrier oil to obtain final product; the mesh number of the silica gel is 60-400 meshes, and the mobile phase can adopt n-hexane-ethyl acetate, petroleum ether-ethyl acetate, n-hexane-dichloromethane, petroleum ether-dichloromethane or a mixed solvent of a plurality of solvents; the chromatography mode can adopt normal pressure or pressurization; the elution mode can adopt isocratic elution or gradient elution; and concentrating the eluent by stages at the concentration temperature of 35-60 ℃.
4. The method of claim 1, wherein the cannabinoid comprises one or more of cannabinoids selected from the group consisting of Cannabidivarin (CBDV), Cannabigerol (CBG), Cannabidiol (CBD), Cannabinol (CBN), Tetrahydrocannabinol (THC), and cannabichromene (CBC).
5. The method of claim 1, wherein the organic solvent is chromatographically pure methanol, and the ratio of the amount of cannabis extract to the volume of methanol is 1: 50.
6. the method for detecting the content of one or more cannabinoids in industrial cannabis extract by HPLC as claimed in claim 1, wherein the ultrasound time is 30min, the ultrasound power is 250W, and the working frequency is 40 kHz.
7. The method for detecting the content of one or more cannabinoids in industrial cannabis extract by HPLC as claimed in claim 1, wherein the standing time is 30 min.
8. The method for detecting the content of one or more cannabinoids in industrial cannabis extract by HPLC as claimed in claim 1, wherein the filter membrane is a 0.22 μm organic needle filter membrane.
9. The method for detecting the content of one or more cannabinoids in industrial cannabis extract by HPLC as claimed in claim 1, wherein the standard control working solution is prepared by the following method: several cannabinoid standard controls, purchased from Sigma, were each diluted with chromatographically pure methanol to a series of standard working solutions ranging in concentration from 1 μ g/mL to 100 μ g/mL.
10. The method for detecting the content of one or more cannabinoids in industrial cannabis extract by HPLC as claimed in claim 1, wherein the HPLC is under the brand name agilent 1260; the chromatographic column is AgilentZORBAX Eclipse Plus C18; the detector is a diode array detector (DAD detector for short).
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112034059A (en) * | 2020-08-21 | 2020-12-04 | 滇麻生物科技(曲靖)有限公司 | Method for detecting cannabinoids in industrial hemp flowers and leaves and extract thereof by high performance liquid chromatography |
| CN112285233A (en) * | 2020-10-22 | 2021-01-29 | 三明海关综合技术服务中心 | Pretreatment method for detecting cannabinoids new psychoactive substances in grease |
| KR102355482B1 (en) * | 2021-02-17 | 2022-02-08 | 바이오메디칼쓰리디프린팅 주식회사 | Cannabinoids Extractive Separation Method and Continuous Measurement Apparatus therefor |
| CN114062526A (en) * | 2020-08-05 | 2022-02-18 | 汉义生物科技（北京）有限公司 | Detection method for quantifying cannabinoids based on relative correction factor method |
| CN115407000A (en) * | 2022-10-17 | 2022-11-29 | 中国计量大学 | Detection method of cannabidiol and tetrahydrocannabinol in industrial cannabis sativa |
| WO2024085420A1 (en) * | 2022-10-20 | 2024-04-25 | 바이오메디칼쓰리디프린팅 주식회사 | Method for producing standard material for chromatographic analysis of low-concentration cannabis |
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2020
- 2020-01-20 CN CN202010066681.7A patent/CN111122744A/en not_active Withdrawn
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114062526A (en) * | 2020-08-05 | 2022-02-18 | 汉义生物科技（北京）有限公司 | Detection method for quantifying cannabinoids based on relative correction factor method |
| CN114062526B (en) * | 2020-08-05 | 2024-03-08 | 汉义生物科技（北京）有限公司 | Detection method for quantifying cannabinoid compounds based on relative correction factor method |
| CN112034059A (en) * | 2020-08-21 | 2020-12-04 | 滇麻生物科技(曲靖)有限公司 | Method for detecting cannabinoids in industrial hemp flowers and leaves and extract thereof by high performance liquid chromatography |
| CN112285233A (en) * | 2020-10-22 | 2021-01-29 | 三明海关综合技术服务中心 | Pretreatment method for detecting cannabinoids new psychoactive substances in grease |
| KR102355482B1 (en) * | 2021-02-17 | 2022-02-08 | 바이오메디칼쓰리디프린팅 주식회사 | Cannabinoids Extractive Separation Method and Continuous Measurement Apparatus therefor |
| CN115407000A (en) * | 2022-10-17 | 2022-11-29 | 中国计量大学 | Detection method of cannabidiol and tetrahydrocannabinol in industrial cannabis sativa |
| WO2024085420A1 (en) * | 2022-10-20 | 2024-04-25 | 바이오메디칼쓰리디프린팅 주식회사 | Method for producing standard material for chromatographic analysis of low-concentration cannabis |
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Application publication date: 20200508 |