CN113956193A - Preparation method of arecoline extract - Google Patents
Preparation method of arecoline extract Download PDFInfo
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- CN113956193A CN113956193A CN202010535638.0A CN202010535638A CN113956193A CN 113956193 A CN113956193 A CN 113956193A CN 202010535638 A CN202010535638 A CN 202010535638A CN 113956193 A CN113956193 A CN 113956193A
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- China
- Prior art keywords
- arecoline
- deep eutectic
- extract
- eutectic solvent
- glycerol
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 239000000284 extract Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 230000005496 eutectics Effects 0.000 claims abstract description 26
- 244000080767 Areca catechu Species 0.000 claims abstract description 23
- 239000000843 powder Substances 0.000 claims abstract description 18
- 235000006226 Areca catechu Nutrition 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000001257 hydrogen Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Chemical group 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 12
- 150000008040 ionic compounds Chemical group 0.000 claims abstract description 10
- 238000002386 leaching Methods 0.000 claims abstract description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 48
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 16
- 235000019743 Choline chloride Nutrition 0.000 claims description 16
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 16
- 229960003178 choline chloride Drugs 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000002137 ultrasound extraction Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000006228 supernatant Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 3
- 229930091371 Fructose Natural products 0.000 claims description 3
- 239000005715 Fructose Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 3
- 229960003237 betaine Drugs 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 229940040102 levulinic acid Drugs 0.000 claims description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 3
- 229960004063 propylene glycol Drugs 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 12
- 230000000052 comparative effect Effects 0.000 description 9
- 238000007873 sieving Methods 0.000 description 6
- 210000000582 semen Anatomy 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 4
- 239000002608 ionic liquid Substances 0.000 description 4
- 238000010298 pulverizing process Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 2
- 238000000643 oven drying Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000010829 isocratic elution Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Abstract
The application provides a preparation method of an arecoline extract, which comprises the following steps: a. preparing areca powder; b. preparing a deep eutectic solvent; wherein the deep eutectic solvent comprises an ionic compound and a hydrogen bond donor; c. mixing the areca catechu powder with the deep eutectic solvent, and leaching to prepare an arecoline extract. The method utilizes the deep eutectic solvent to extract the arecoline in the areca, and realizes green, safe and efficient extraction of the arecoline.
Description
Technical Field
The application relates to the technical field of natural substance extraction, in particular to a preparation method of an arecoline extract.
Background
DESs (Deep Eutectic solvents), which is the first reported in 2003 by Abbott et al, university of Leicester, uk, refers to two-or three-component Deep Eutectic mixtures of hydrogen bond acceptors (e.g., quaternary ammonium salts) and hydrogen bond donors (e.g., amides, carboxylic acids, and polyols) in a stoichiometric ratio that have freezing points significantly below the melting points of the pure materials of each component.
DESs have very similar physicochemical properties to ionic liquids, and therefore have also been classified as a new class of ionic liquids or ionic liquid analogues. Compared with ionic liquid, the DESs have the advantages of low price of raw materials, easy biodegradation, no waste generated in the preparation process and better environmental compatibility. As a novel green solvent, DESS is applied to various fields such as organic synthesis, electrochemistry, material chemistry, biocatalysis and the like. At present, the application of DESS in separation and extraction mainly focuses on polyphenols, aromatic hydrocarbons and terpenes, and the extraction of related alkaloid components is hardly reported.
Disclosure of Invention
The application provides a preparation method of an arecoline extract, aiming at extracting arecoline in areca by using DESS and realizing green, safe and efficient extraction of the arecoline.
The application provides a preparation method of an arecoline extract, which comprises the following steps:
a. preparing areca powder;
b. preparing a deep eutectic solvent; wherein the deep eutectic solvent comprises an ionic compound and a hydrogen bond donor;
c. mixing the areca catechu powder with the deep eutectic solvent, and leaching to prepare an arecoline extract.
In some embodiments, the ionic compound comprises choline chloride, betaine; preferably, the ionic compound is choline chloride.
In some embodiments, the hydrogen bond donor is selected from at least one of glycerol, urea, 1, 2-propanediol, glucose, fructose, malonic acid, levulinic acid, proline; preferably, the hydrogen bond donor is glycerol.
In some aspects, the deep eutectic solvent further comprises water.
In some embodiments, the molar ratio of choline chloride to glycerol is 1: 1.5-2.5.
In some embodiments, the ratio of the total volume of the choline chloride and the glycerol to the volume of the water is 7: 2 to 4.
In some embodiments, the deep eutectic solvent is obtained by mixing the choline chloride and the glycerol under stirring to obtain an organic solvent, and then mixing the organic solvent with water.
In some schemes, the stirring temperature is 70-90 ℃, and the stirring speed is 200-400 r/min.
In some embodiments, the material-to-liquid ratio of the betel nut powder to the deep eutectic solvent is 1 g: 15ml to 25 ml.
In some embodiments, the areca nut powder is obtained by pulverizing, sieving, and drying an areca nut raw material.
In some schemes, the number of the sieving meshes is 30-50, and the drying temperature is 30-50 ℃.
In some embodiments, the leaching is performed under sonication conditions.
In some schemes, the temperature of ultrasonic extraction is 50-80 ℃, the frequency of ultrasonic extraction is 30-80 kHz, and the time of ultrasonic extraction is 20-40 min.
In some embodiments, the method further comprises centrifuging, and concentrating the supernatant after centrifuging to obtain the arecoline extract.
In some schemes, the rotating speed of the centrifugal separation is 8000 r/min-12000 r/min, and the time of the centrifugal separation is 5 min-15 min.
According to the preparation method of the arecoline extract, the arecoline in the areca is extracted by using the deep eutectic solvent, so that green, safe and efficient extraction of the arecoline is realized.
Drawings
FIG. 1 is a schematic liquid chromatogram of arecoline extract prepared in the first embodiment of the present application;
FIG. 2 is a liquid chromatogram of arecoline extract prepared in comparative example I of the present application.
Detailed Description
The present application will be further described in conjunction with the following examples.
The embodiment of the application provides a preparation method of an arecoline extract, which comprises the following steps:
a. preparing areca powder;
b. preparing a deep eutectic solvent; wherein the deep eutectic solvent comprises an ionic compound and a hydrogen bond donor;
c. mixing the areca catechu powder with the deep eutectic solvent, and leaching to prepare an arecoline extract.
It should be noted that, the order of step a and step b is not sequential.
In some embodiments, the ionic compound comprises choline chloride, betaine; preferably, the ionic compound is choline chloride.
In some embodiments, the hydrogen bond donor is selected from at least one of glycerol, urea, 1, 2-propanediol, glucose, fructose, malonic acid, levulinic acid, proline; preferably, the hydrogen bond donor is glycerol.
In some aspects, the deep eutectic solvent further comprises water.
In some embodiments, the molar ratio of choline chloride to glycerol is 1: 1.5-2.5.
In some embodiments, the ratio of the total volume of the choline chloride and the glycerol to the volume of the water is 7: 2 to 4.
In some embodiments, the deep eutectic solvent is obtained by mixing the choline chloride and the glycerol under stirring to obtain an organic solvent, and then mixing the organic solvent with water.
In some schemes, the stirring temperature is 70-90 ℃, and the stirring speed is 200-400 r/min.
In some embodiments, the material-to-liquid ratio of the betel nut powder to the deep eutectic solvent is 1 g: 15ml to 25 ml.
In some embodiments, the areca nut powder is obtained by pulverizing, sieving, and drying an areca nut raw material.
In this embodiment, the raw material of betel nut includes, but is not limited to, fruit, nut shell, kernel, petiole, flower, leaf, bark, resin, root, etc. of betel nut plant, plant extract containing arecoline other than betel nut, etc.
In some schemes, the number of the sieving meshes is 30-50, and the drying temperature is 30-50 ℃.
In some embodiments, the leaching is performed under sonication conditions.
In some schemes, the temperature of ultrasonic extraction is 50-80 ℃, the frequency of ultrasonic extraction is 30-80 kHz, and the time of ultrasonic extraction is 20-40 min.
In some embodiments, the method further comprises centrifuging, and concentrating the supernatant after centrifuging to obtain the arecoline extract.
In some schemes, the rotating speed of the centrifugal separation is 8000 r/min-12000 r/min, and the time of the centrifugal separation is 5 min-15 min.
The first embodiment is as follows:
pulverizing Arecae semen fruit, sieving with 40 mesh sieve, oven drying at 40 deg.C to constant mass to obtain Arecae semen powder, and storing in 4 deg.C refrigerator;
140g (1mol) of choline chloride and 184g (2mol) of glycerol are mixed and stirred (85 ℃, 300r/min) to obtain colorless transparent liquid; then adding water according to the volume ratio of 7:3, and continuously stirring to obtain a deep eutectic solvent;
mixing 20g of areca nut powder with 400ml of deep eutectic solvent, and carrying out ultrasonic treatment for 30min at the temperature of 70 ℃ and the frequency of 50 kHz;
centrifuging the ultrasonic extractive solution for 10min at 10000r/min, collecting supernatant, and concentrating to obtain arecoline extract.
Comparative example one:
pulverizing Arecae semen fruit, sieving with 40 mesh sieve, oven drying at 40 deg.C to constant mass to obtain Arecae semen powder, and storing in 4 deg.C refrigerator;
mixing 20g of Arecae semen powder with 400ml of water, and performing ultrasonic treatment at 70 deg.C and 50kHz for 30 min;
centrifuging the ultrasonic extractive solution for 10min at 10000r/min, collecting supernatant, and concentrating to obtain arecoline extract.
Experimental test methods and results:
1. the arecoline extraction rates of example one and comparative example one were calculated according to the following formula: arecoline extraction rate (arecoline mass/areca powder mass) x 100%;
the arecoline extraction rates of the first example and the first comparative example obtained by the above calculation method are shown in the following table:
| name (R) | Extract character | Arecoline extraction rate |
| Example one | Dark brown oil | 0.192％ |
| Comparative example 1 | Brown oil | 0.123％ |
As can be seen from the table, the arecoline extraction rate of the arecoline extract prepared in the first example is obviously higher than that of the first comparative example, and the efficient extraction of the arecoline is realized.
2. The quality of the arecoline extracts of example one and comparative example one was tested using the following test conditions:
| name (R) | Parameter(s) |
| Chromatographic column | InertSustain C18,4.6x250mm,3.5um |
| Mobile phase | Acetonitrile-0.1% triethylamine aqueous solution (20:80) isocratic elution |
| Wavelength of light | 215nm |
| Flow rate of flow | 1.0ml/min |
| Column temperature | 40℃ |
With the test conditions, a schematic liquid chromatogram of the arecoline extract of example one is obtained, which can be referred to as fig. 1; the liquid chromatogram of the arecoline extract obtained in comparative example I is shown in FIG. 2.
As can be seen from fig. 1 and 2, the arecoline content of the arecoline extract prepared in example one is significantly higher than that of comparative example one.
This written description uses examples to disclose the invention, including the best mode, and also to enable any person skilled in the art to make and use the application. The patentable scope of the application is defined by the claims, and may include other examples that occur to those skilled in the art. Such other examples are intended to be within the scope of the claims if they have structural elements that do not differ from the literal language of the claims, or if they include equivalent structural elements with insubstantial differences from the literal languages of the claims. All citations referred to herein are incorporated herein by reference to the extent that no inconsistency is made.
Claims (10)
1. A method for preparing arecoline extract comprises the following steps:
a. preparing areca powder;
b. preparing a deep eutectic solvent; wherein the deep eutectic solvent comprises an ionic compound and a hydrogen bond donor;
c. mixing the areca catechu powder with the deep eutectic solvent, and leaching to prepare an arecoline extract.
2. The method of claim 1, wherein the ionic compound comprises choline chloride, betaine; preferably, the ionic compound is choline chloride.
3. The method according to any of claims 1 or 2, characterized in that the hydrogen bond donor is selected from at least one of glycerol, urea, 1, 2-propanediol, glucose, fructose, malonic acid, levulinic acid, proline; preferably, the hydrogen bond donor is glycerol.
4. The method of any one of claims 1-3, wherein the deep eutectic solvent further comprises water.
5. A process according to any one of claims 2 to 4, wherein the molar ratio of choline chloride to glycerol is from 1: 1.5-2.5.
6. A process according to claim 4 or 5, characterized in that the ratio of the total volume of choline chloride and glycerol to the volume of water is 7: 2 to 4.
7. The method according to any one of claims 4 to 6, wherein the deep eutectic solvent is obtained by mixing the choline chloride and the glycerol under stirring to obtain an organic solvent, and then mixing the organic solvent with water.
8. The method according to any one of claims 1 to 7, wherein the material-to-liquid ratio of the betel nut powder to the deep eutectic solvent is 1 g: 15ml to 25 ml.
9. A process according to any one of claims 1 to 8, wherein the leaching is carried out under ultrasonic conditions; furthermore, the temperature of ultrasonic extraction is 50-80 ℃, the frequency of ultrasonic extraction is 30-80 kHz, and the time of ultrasonic extraction is 20-40 min.
10. The method of claim 9, further comprising centrifuging, and concentrating the supernatant after centrifugation to produce the arecoline extract.
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Cited By (1)
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2020
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