AU2020102074A4 - A method for extracting phenolic compounds from Lepidium latifolium L. and the extracted phenolic compounds - Google Patents
A method for extracting phenolic compounds from Lepidium latifolium L. and the extracted phenolic compounds Download PDFInfo
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- AU2020102074A4 AU2020102074A4 AU2020102074A AU2020102074A AU2020102074A4 AU 2020102074 A4 AU2020102074 A4 AU 2020102074A4 AU 2020102074 A AU2020102074 A AU 2020102074A AU 2020102074 A AU2020102074 A AU 2020102074A AU 2020102074 A4 AU2020102074 A4 AU 2020102074A4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
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- C07C63/04—Monocyclic monocarboxylic acids
- C07C63/06—Benzoic acid
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Abstract
The invention belongs to the technical field of compound extraction, specifically involving a
method for extracting phenolic compounds from Lepidium latifolium L. and the extracted
phenolic compounds. The extraction method is shown in formula (I). First extracting the dried
whole Lepidium latifolium L. coarse powder by alcohol, then carrying out pressure reduction
condensation to get extraction, and eluting the obtained extraction with silica gel column
chromatography, finally eluting again with MCI column chromatography to extract phenolic
compound from Lepidium latifolium L.. This method has solved the problem that there is no
specific method to extract phenolic compounds from Lepidium latifolium L. in the existing
technology which seriously limits the utilization and research of Lepidium latifolium L..
Description
A method for extracting phenolic compounds from Lepidium latifolium L. and the extracted phenolic compounds
[01] The invention belongs to the technical field of compound extraction, specifically involving a method for extracting phenolic compounds from Lepidium latifolium L. and the extracted phenolic compounds.
[02] Belonging to Brassicaceae Lepidium, Lepidium latifolium L. is distributed all over the country, besides, it can treat visceral congestion, bone disease, rheumatoid arthritis as well as edema, hypertension and other diseases. There are rich phenolic compounds in Lepidium latifolium L., which have good functions of antioxidant, antiplatelet activity, anti atherosclerosis, antibacterial, anti-tumor, liver protection and the like.
[03] At present, there is still no specific method for extracting phenolic compounds from Lepidium latifolium L., which seriously limits the utilization and research of Lepidium latifolium L..
[04] In order to solve the technical problem mentioned in background, the invention provides a method for extracting phenolic compounds from Lepidium latifolium L. and its extracted phenolic compounds.
[05] The adopted technical scheme is to provide a method for extracting phenolic compounds from Lepidium latifolium L including the following steps.
[06] Si. Dry Lepidium latifolium L. at 55 to 65C for 4 to 6 days, and then grind
it to get coarse powder of 20 to 80 mesh.
[07] S2. Extract the coarse with solvent under ultrasonic waves for 1 to3 times to get extracting solution and then mix the extracting solution for pressure reduction condensation to obtain extracum.
[08] S3. Add water into the extracum from step S2 for dispersion, and then add phenolic extractant for extraction to obtain the extract.
[09] S4. After pressure reduction condensation and silica gel column chromatography, the extract obtained in step S3 is eluted with silica gel column eluent, and then eluted again with gradient eluent of micro-porous resin column after micro-porous resin column chromatography. Finally, analyzing it with Dubhe C18 column and Megress C18 column successively, and eluting to obtain phenolic compounds.
[010] The beneficial effect of the extraction method is that the used reagents and materials are easy to prepared in batches because of their wide distribution and large resources. There is no specific method to extract phenolic compounds from Lepidium latifolium L. in the existing technology which seriously limits the utilization and research of Lepidium latifolium L.. While, companied with simple operation, good repeatability and stable and controllable quality, the invention can purify and extract phenolic compounds quickly and easily from Lepidium latifolium L., which solves above technical problem.
[011] Based on the above technical scheme, following improvements can be made.
[012] Further, adopting ethanol as solvent and the extraction is performed for 1 to 2 hours under ultrasonic conditions of 40KHz and 600W in step 2. Moreover, the dosage ratio of the ethanol and the coarse powder is (5-15L) : lkg.
[013] The beneficial effect of the above-mentioned further scheme is that ethanol is in a low price and easy to produce in large scale. The above ultrasonic extraction conditions can improve the purity of phenolic compounds.
[014] Specifically, the dosage ratio of ethanol to the coarse powder is further 1OL: 1kg, which brings the beneficial effect that a determinate ratio can greatly improve the quality and purity of phenolic compounds extracted and obtained.
[015] Further, the pressure reduction condensation temperature is 60-85°C, the pressure is 100-300hpa and the time is 1030 minutes.
[016] The beneficial effect of adopting the above further scheme is that the above pressure reduction condensation conditions can lead to better extracum, which is conducive to the production of the final product.
[017] In step 3, further the phenolic extractant is any one of petroleum ether, ethyl acetate and n-butanol, and the volume ratio of the phenolic extractant to water is 0.5: (10 ~1).
[018] The beneficial effect of above schemes is that certain phenolic compounds can be obtained from certain phenolic extractants. And suitable phenolic extractant can be mixed with water to get phenolic compounds with better purity.
[019] Further, the volume ratio of the phenolic extractant to water is 1: 1.
[020] The beneficial effect of using the further scheme mentioned above is that the volume ratio of the phenolic extractants to water yields the phenolic compounds with the highest purity.
[021] Further, in step 4, the eluent is a mixture of dichloromethane, methanol and water in a volume ratio of 7:3:0.5.
[022] The gradient eluent of the microporous resin column is methanol and water, and the gradient elution is carried out according to the volume ratio of methanol to water of 3:7, 6:4 and 9:1.
[023] The eluent of Dubhe C18 column and Megres C18 column is both acetonitrile and formic acid aqueous solution, wherein, the mass concentration of the formic acid is 0.2%. The gradient elution procedure of Dubhe C18 column is using
acetonitrile with lOwt%-10wt%-20wt%-30wt%-50wt% for 0-30-50-60-80 min
successively, and of Megres C18 column is using acetonitrile with 15wt%-15wt% for
-50 min successively.
[024] The beneficial effect of using the further schemes described above is that a certain elution procedure can filter out other impurities and get definite phenolic compounds.
[025] Further, the micro-porous resin column is MCI resin, with a better separation effect of definite resin.
[026] In the other hand, the invention also provides a phenolic compound obtained by using above extraction method with a general structural formula as the following chemical formula (I).
R2
R1 R3
[027] 0H chemical formula (I)
[028] Adopting the above preparation method can botain a phenolic compound as formula(I) , which solves that problem that there is still no specific method for extracting phenolic compounds from Lepidium latifolium L. at present causing seriously limit on the utilization and research of Lepidium latifolium L.. In addition, it can fill the production of phenolic compounds.
[029] Based on the above technical schemes, the invention also can make improvement as follows, that is, the phenolic compound is any one of the followings further.
[030] 4-Hydroxybenzoic acid syringate p-Hydroxy-cinnamic acid
OH OCRH oca0 )c OH OH 0
[031] vanillin vanillic acid p-Hydroxy phenylacetylene OH OH 0 OH 0
I 0
[032] The beneficial effect of the further scheme mentioned above is that if the phenolic extractant is petroleum ether, 4-Hydroxybenzoic acid is obtained. If the phenolic extractant is n-butanol, p-Hydroxy-cinnamic acid is obtained and if the phenolic extractant is ethyl acetate, syringate, vanillin, vanillic acid and 3 -Hydroxy
phenylacetylene are obtained.
[033] The principles and features of the invention are described below. The embodiments are only used to explain the invention, not to limit the scope of the invention.
[034] Embodiment 1
[035] A method for extracting phenolic compounds from Lepidium latifolium L. including steps as follows.
[036] Si. Dry Lepidium latifolium L. of 20kg at 55°C for 4 days, and then grind it to get coarse powder of 40 mesh.
[037] S2. Extract the coarse with ethanol of 95wt% under ultrasonic conditions of 40KHz and 600W for 3 times, each for 1 hour to get extracting solution and then mix the extracting solution for pressure reduction condensation with temperature of 65°C and pressure of 150hpa for 20 minutes to obtain extracum of 1.8kg.
[038] S3. Add water of 100kg into the extracum from step S2 for dispersion, and then add phenolic extractant of 100kg for extraction to obtain the extract of 72.6kg.
[039] S4. Subject the extract obtained in step3 into pressure reduction condensation with 65°C and 150hpa for 20 minutes to obtain extract of 35g. After silica gel column chromatography, it is eluted with silica gel column eluent which is a mixture of dichloromethane, methanol and water in a volume ratio of 7:3:0.5.
[040] And then performing MIC column chromatography on the extract, and eluting it again with gradient eluent of micro-porous resin column, which is methanol and water, meanwhile the gradient elution is carried out according to the volume ratio of methanol to water of 3:7, 6:4 and 9:1, successively. Finally, analyzing it with Dubhe C18 column and Megress C18 column successively, and eluting to obtain phenolic compounds 4-Hydroxybenzoic acid, wherein, the gradient elution procedure of Dubhe C18 column is using acetonitrile with 0wt%-10wt%-20wt%-30wt%-50wt% for 0-30 -60-80 min successively, and of Megres C18 column is using acetonitrile with wt%-15wt% for 0-50 minutes successively.
[041] The structure of the obtained 4-Hydroxybenzoic acid is elucidated, and the results are as follows.
[042] By spectral analysis, 4-Hydroxybenzoic acid is white powder, with molecular formulaof C7H603, 'H NMR (600 MHz, MEOD) 6: 7.88 (2H,d,J=14 Hz,H 2,H-6), 6.83(2H,d,J=14 Hz,H-3,H-5); 13C-NMR(600 MHz, MEOD) 6:168.7(s,C-7), 162.0(s,C-4), 131.6(s,C-2,C-6), 121.4(s, C-1), 114.6(s,C-3,C-5).
[043] Embodiment 2
[044] The difference from embodiment 1 is that in step 3, 100kg ethyl acetate is added for extraction, instead of 100kg petroleum ether, to obtain syringate.
[045] The structure of the obtained syringate is elucidated, and the results are as follows.
[046] By spectral analysis, syringate is white powder, with molecular formula of C9Hi005, 1H NMR(600 MHz, MEOD) 6:7.33(2H,s, H-2,H-6), 3.88(6H,s,3,5-OCH3); 13 C-NMR (600 MHz, MEOD) 6: 168.7 (s, C-7), 147.4 (s, C-3, C-5), 140.3 (s, C-4), 120.7 (s, C-1), 106.9 (s, C-2, C-6), 55.4 (s, 3,5-OCH3).
[047] Embodiment 3
[048] The difference from mbodiment 1 is that in step 3, 100kg n-butanol is added for extraction, instead of 100kg petroleum ether, to obtain p-Hydroxy-cinnamic acid.
[049] The structure of the obtained p-Hydroxy-cinnamic acid is elucidated, and the results are as follows.
[050] By spectral analysis, p-Hydroxy-cinnamic acid is white crystal, with molecular formula of C9H803, 1H NMR (600 MHz, MEOD) 6: 7.60 (1H, d, J =15.9 Hz, H-7), 7.45 (2H, d, J =8.6 Hz, H-3,5), 6.80 (2H, d, J =8.6 Hz, H-2,6), 6.28 (1H, d, J =15.9 Hz, H-8); 13 C-NMR (600 MHz, MEOD) 6: 169.6 (s, C-9),159.8 (s, C-1), 145.2
(s, C-7), 129.7 (s, C-3,5), 125.8 (s, C-4), 115.4 (s, C-2,6), 114.2 (s, C-8).
[051] Embodiment 4
[052] The difference from embodiment 1 is that in step 3, 100kg ethyl acetate is added for extraction, instead of 100kg petroleum ether, to obtain vanillin.
[053] The structure of the obtained vanillin is elucidated, and the results are as follows.
[054] By spectral analysis, vanillin is white solid, 1 H NMR (600 MHz, CD30D) 6: 9.74 (1H, s, -CHO), 7.43 (1H, s, H-2), 7.41 (1H, d, J =7.9 Hz , H-6), 6.93 (1H, d, J =7.9Hz), 3.92 (3H, s, -OCH3); 13C NMR (150 MHz, CD30D) 6:191.48 (s, C-7),153.3 (s, C-4), 148.29 (s, C-3), 129.29 (s, C-1), 126.50 (s, C-6), 114.92 (s, C-5), 109.93 (s,C 2), 54.98 (s, -OCH3).
[055] Embodiment 5
[056] The difference from embodiment 1 is that in step 3, 100kg ethyl acetate is added for extraction, instead of 100kg petroleum ether, to obtain vanillic acid.
[057] The structure of the obtained vanillic acid is elucidated, and the results are as follows.
[058] By spectral analysis, vanillic acid is white powder, with molecular formula of C8H804, ESI-MS m/z: 167 [M-H]-. 1H NMR (600 MHz, CD30D) 6: 7.59 (1H, dd, J =8.0, 1.6 Hz, H-6), 7.57 (1H, d, J =1.6 Hz , H-2), 6.86 (1H, d, J =8.0 Hz , H-5), 3.90
(3H, s, -OCH3) 13C NMR (150 MHz, CD30D) 6: 168.74 (s, C-7), 151.23 (s, C-4),
147.23 (s, C-3), 123.93 (s, C-6), 121.67 (s, C-1), 114.47 (s, C-2), 112.40 (s,C-5), 55.02 (s, -OCH3).
[059] Embodiment 6
[060] The difference from embodiment 1 is that in step 3, 100kg ethyl acetate is added for extraction, instead of 100kg petroleum ether, to obtain p-Hydroxy phenylacetylene.
[061] The structure of the obtained p-Hydroxy phenylacetylene is elucidated, and the results are as follows.
[062] By spectral analysis,j-Hydroxy phenylacetylene is white amorphous powder, with molecular formula of C1oH1204, ESI-MS m/z: 195[M-H]-. 1 H NMR (600 MHz, CD30D) 6: 7.57 (1H, dd, J =8.2, 2.0 Hz, H-6'), 7.54 (1H, d, J =2.0 Hz , H-2'), 6.86 (1H, d, J =8.2 Hz , H-5'), 3.94 (2H, t, J=6.1 Hz H-3), 3.90 (3H, s, 3-OCH3),3.16 (2H, t, J =6,1 Hz, H-2); 13 C NMR (150 MHz, CD30D) 6: 198.30 (s, C-1), 151.94 (s, C 3'), 147.67 (s, C-4'), 129.24 (s, C-i'), 123.33 (s, C-6'), 114.40 (s, C-5'), 110.49 (s,C-2'), 57.53 (s, C-3), 54.99 (s, 3-OCH3), 40.26 (s, C-2).
[063] In the description of this specification, the terms "an embodiment", "some embodiments", "concrete embodiments", etc., mean that the specific features, structures, materials or characteristics described by the embodiment or example are included in at least one embodiment or example of the invention. In this specification, a schematic representation of the term does not necessarily refer to the same embodiment or instance. Furthermore, the specific features, structures, materials or characteristics described can be combined in an appropriate manner in any one or more embodiments or examples.
[064] Although the invention has been described with reference to specific examples, it will be appreciated by those skilled in the art that the invention may be embodied in many other forms, in keeping with the broad principles and the spirit of the invention described herein.
[065] The present invention and the described embodiments specifically include the best method known to the applicant of performing the invention. The present invention and the described preferred embodiments specifically include at least one feature that is industrially applicable
Claims (10)
1. A method for extracting phenolic compounds from Lepidium latifolium L. is characterized by comprising the following steps.
Si. Dry Lepidium latifolium L. at 55 to 65°C for 4 to 6 days, and then grind it to get coarse powder of 20 to 80 mesh.
S2. Extract the coarse with solvent under ultrasonic waves for 1 to3 times to get extracting solution and then mix the extracting solution for pressure reduction condensation to obtain extracum.
S3. Add water into the extracum from step S2 for dispersion, and then add phenolic extractant for extraction to obtain the extract.
S4. After pressure reduction condensation and silica gel column chromatography, the extract obtained in step S3 is eluted with silica gel column eluent, and then eluted again with gradient eluent of micro-porous resin column after micro-porous resin column chromatography. Finally, analyzing it with Dubhe C18 column and Megress C18 column successively, and eluting to obtain phenol compounds.
2. The extraction method according to claim 1 is characterized in that adopting ethanol as solvent and the extraction is performed for 1 to 2 hours under ultrasonic conditions of 40KHz and 600W in step 2. Moreover, the dosage ratio of the ethanol and the coarse powder is (5~15L) : lkg.
3. The extraction method according to claim 2 is characterized in that the dosage ratio of ethanol to the coarse powder is specifically 1OL: lkg.
4. The extraction method according to claim 1 is characterized in that in steps 2 and 3, the pressure reduction condensation temperature is 60-85°C, the pressure is 100-300hpa and the time is 1030 minutes.
5. The extraction method according to claim 1 is characterized in that in step 3, the phenolic extractant is any one of petroleum ether, ethyl acetate and n-butanol, and the volume ratio of the phenolic extractant to water is 0.5: (10 ~ 1).
6. The extraction method according to claim 5 is characterized in that the volume ratio of the phenolic extractant to water is 1: 1.
7. The extraction method according to any one of claims 1 to 6 is characterized in that in step 4, the eluent is a mixture of dichloromethane, methanol and water in a volume ratio of 7:3:0.5.
The gradient eluent of the microporous resin column is methanol and water, and the gradient elution is carried out according to the volume ratio of methanol to water of 3:7, 6:4 and 9:1.
The eluent of Dubhe C18 column and Megres C18 colum is both acetonitrile and formic acid aqueous solution, wherein, the mass concentration of the formic acid is 0.2%. The gradient elution procedure of Dubhe C18 column is using acetonitrile with l0wt% - l0wt% - 20wt% - 30wt% - 50wt% for 0-30-50-60-80 min successively, and of Megres C18 column is using acetonitrile with 15wt% - 15wt% for 0-50 min successively.
8. The extraction method according to claim 7 is characterized in that the micro porous resin column is MCI resin.
9. The phenolic acid compound obtained by using the extraction method in any one of claims 1 to 8, is characterized by its general structural formula shown as the following chemical formula (I).
R2
R1 R3 chemical formula (I) OH
10. The phenolic compound according to claim 9 is characterized in that its phenolic compound is any one of the followings.
OH O OH 0 OH
o o
OH OH OH
4-Hydroxybenzoic acid syringate p-Hydroxy-cinnamic acid CHO COOH
Ho
OCH3 oca Oc
oH oH
vanillin vanillic acid p-Hydroxy phenylacetylene
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115368359A (en) * | 2022-09-15 | 2022-11-22 | 中国科学院西北高原生物研究所 | Alkaloid antioxidant and preparation method and application thereof |
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2020
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115368359A (en) * | 2022-09-15 | 2022-11-22 | 中国科学院西北高原生物研究所 | Alkaloid antioxidant and preparation method and application thereof |
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