CN108892608A - The preparation method of zerumbone reference substance in Rhizoma Zingiberis zerumbet - Google Patents
The preparation method of zerumbone reference substance in Rhizoma Zingiberis zerumbet Download PDFInfo
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- CN108892608A CN108892608A CN201811107415.3A CN201811107415A CN108892608A CN 108892608 A CN108892608 A CN 108892608A CN 201811107415 A CN201811107415 A CN 201811107415A CN 108892608 A CN108892608 A CN 108892608A
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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- G01N30/02—Column chromatography
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Abstract
The invention discloses a kind of preparation methods of zerumbone reference substance in Rhizoma Zingiberis zerumbet, the present invention is using fresh Rhizoma Zingiberis zerumbet underground rhizome as raw material, extract volatile oil, zerumbone reference substance is prepared by recrystallization method, the zerumbone sterling of prepared acquisition, it is detected through HPLC, it is a mass-tone spectral peak in different mobile phases and chromatographic column measurement result, change mobile phase and chromatographic column measurement does not occur anomaly peak, it is greater than 99% with area normalization method measurement reference substance purity, meets the requirement of assay traditional Chinese chemical contrast.
Description
Technical field
The present invention relates to a kind of separating and purifying technologies, especially using fresh Rhizoma Zingiberis zerumbet underground rhizome as raw material, extract volatilization
Oil, the method that zerumbone reference substance is prepared by recrystallization.
Background technique
Rhizoma Zingiberis zerumbet (Zingiber zerumbet (L.) Smith) is Zingiber zingiber herbaceos perennial.It is i.e. pharmaceutically acceptable,
Again edible, underground rhizome can be used as appetizer and food dressing.According to《Guangxi plant register》It records, the rhizome of Rhizoma Zingiberis zerumbet
Detoxify with wind-dispelling, control collywobbles, the function of diarrhea, modern pharmacology research shows that Rhizoma Zingiberis zerumbet has antitumor, anti-inflammatory, antioxygen
The pharmacological actions such as change, antiallergy, antimicrobial, antihyperglycemic and analgesia.
Primary pharmacological activity ingredient of the zerumbone as Rhizoma Zingiberis zerumbet, belongs to sesquiterpenoids.Domestic and foreign literature report
Show zerumbone have anti-malignant tumor activity, anti-inflammatory activity, antibacterial activity, anti-osteoporosis activity and hepatoprotective effect,
Analgesic activity and improvement diabetes effect.Current study show that potential candidate of the zerumbone as anticancer drug, has wide
Application prospect.Therefore, the zerumbone reference substance of high-purity how is prepared, needs solve.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of preparation methods of zerumbone reference substance in Rhizoma Zingiberis zerumbet, with new
Fresh Rhizoma Zingiberis zerumbet underground rhizome is raw material, extracts volatile oil, prepares zerumbone reference substance by recrystallization, it can be from Rhizoma Zingiberis zerumbet
Separation obtains the zerumbone of very high purity.
The invention is realized in this way：Using fresh Rhizoma Zingiberis zerumbet underground rhizome as raw material, volatile oil is extracted, by recrystallization side
Method prepares zerumbone reference substance, comprises the technical steps that：
(1) extraction of Rhizoma Zingiberis zerumbet volatile oil：Fresh Rhizoma Zingiberis zerumbet underground rhizome is crushed, raw material and distilled water are pressed 1:2-1:
5 solid-liquid ratio, extracts 2h-6h in volatile oil extractor, through n-hexane extraction, filters after being removed water with anhydrous sodium sulfate, decompression
Concentration obtains Rhizoma Zingiberis zerumbet volatile oil after removing n-hexane；
(2) recrystallization isolates and purifies to obtain zerumbone reference substance：To be added n-hexane in Rhizoma Zingiberis zerumbet volatile oil, volatile oil with
The solid-liquid ratio of n-hexane is 2:1-1:2, after heating for dissolving, 5min-30min is recrystallized at -22 DEG C, filters to obtain zerumbone crystal
Crude product；N-hexane will be added in zerumbone crystal crude product again, the solid-liquid ratio of volatile oil and n-hexane is 2:1-1:2, it dissolves by heating
Afterwards, 5min-20min is recrystallized at -22 DEG C, is filtered, and the zerumbone sterling that purity is 99% or more is obtained.
In order to further verify technical effect of the invention, following experiment has been carried out：
The separation of 1 zerumbone monomeric compound
The extraction of 1.1 Rhizoma Zingiberis zerumbet volatile oil
Fresh Rhizoma Zingiberis zerumbet underground rhizome 500g is weighed, after crushing, is placed in 2L round-bottomed flask, several beades and steaming is added
Distilled water 1000mL after stirring evenly, is placed in electric jacket, connects volatile oil extractor.Distilled water is added from the upper end of condenser pipe, until
Distilled water is until overflow enters round-bottomed flask from determination of volatile oil pipe.Heating keeps slightly boiled 4h.By in extractor water and volatilization
It is oily to release, it is concentrated under reduced pressure after removing n-hexane with being filtered after the water removal of appropriate anhydrous sodium sulfate through appropriate n-hexane extraction and is obtained Rhizoma Zingiberis zerumbet
Volatile oil obtains volatile oil 0.51g.
The 1.2 isolated zerumbone reference substances of recrystallization
The n-hexane of 0.3mL is added in Rhizoma Zingiberis zerumbet volatile oil, shakes up dissolution in 40 DEG C of heating, is refrigerated at -22 DEG C
15min after precipitating crystal, filters to obtain zerumbone crystal crude product；0.2mL n-hexane will be added in zerumbone crystal crude product again,
40 DEG C of heating shake up dissolution, and 10min is refrigerated at -22 DEG C, filter, and obtain the zerumbone sterling 0.32g that purity is 99% or more.
Through MS,1H-NMR,13C-NMR is measured confirmation.
1.3 conclusion
By MS,1H-NMR,13C-NMR is measured, and is determined as zerumbone.EI-MS determination data shows and composes in library
Zerumbone Data Matching；1H-NMR,13C-NMR is consistent with document zerumbone data.EI-MS m/z (%)：218 [M+], 203,
189,175,163,150,135 (100), 121,107,96,79,67,53,41.1H-NMR(CDCl3, 400MHz), δ：5.96-
5.92 (1H, m, H-6), 5.89 (1H, d, J=16.4Hz, H-9), 5.78 (1H, d, J=16.4Hz, H-10), 5.18 (1H, bd,
J=15.1Hz, H-2), 2.43-2.30 (1H, m, H-5), 2.30-2.12 (4H, m, H-1, H-4, H-5), 1.88-1.75 (1H,
M, H-1), 1.72 (3H, s, H-13), 1.46 (3H, s, H-12), 1.13 (3H, s, H-14), 0.99 (3H, s, H-15)；13C-NMR
(CDCl3, 100MHz), δ：42.4 (C-1), 125.0 (C-2), 136.3 (C-3), 39.5 (C-4), 24.5 (C-5), 148.9 (C-
6), 137.9 (C-7), 204.3 (C-8), 127.2 (C-9), 160.7 (C-10), 37.9 (C-11), 15.3 (C-12), 11.8 (C-
13), 29.5 (C-14), 24.3 (C-15).As a result as shown in Fig. 3, Fig. 4 and Fig. 5.
The purity detecting of 2 zerumbone reference substances
2.1 high performance liquid chromatographies-purity test
Using Agilent 1260 type high performance liquid chromatograph (quaternary pump, column oven, autosampler, DAD ultraviolet detection
Device, ChemStation chromatographic work station), with Agilent company ZORBAX SB-C18 (4.6 × 250mm, 5 μm) chromatographic column, column
48 DEG C of temperature, mobile phase are -0.25% acetic acid (70 of acetonitrile:30), DAD sets wave-length coverage as 200~400nm, setting 240,
260,280, five 290,310nm Detection wavelengths, and the detection case of other wavelength is observed simultaneously, to investigate the pure of zerumbone
Degree.
Using acetonitrile as solvent, zerumbone is configured to the solution of every 1.5mg/mL, as test solution, takes blank solvent
Each 10 μ L of (acetonitrile) and test solution, is injected separately into liquid chromatograph, after as a result deducting the chromatographic peak that blank solvent generates, ball
The chromatographic peak area normalization content of zingiberone is all larger than 99% or more under each wavelength, is shown in Table 1, Fig. 6 and Fig. 7.
The measurement result of each wavelength of 1 zerumbone of table
2.2 mobile phases are investigated
Zerumbone test liquid is taken, uses -0.25% acetic acid (70 of acetonitrile respectively:30), -0.05% formic acid (80 of methanol:20), second
Nitrile-methanol-water (60:15:25), acetonitrile-water (80:20), methanol-water (80:20) it is mobile phase, obtains HPLC map, as a result
Show do not occur anomaly peak under the conditions of each mobile phase, remove solvent peak, under the conditions of each mobile phase of area normalization method measurement
The content of zerumbone is all larger than 99%.It the results are shown in Table 2, Fig. 8-12.
2 mobile phase result of study of table
The investigation of 2.3 pillars
Zerumbone test liquid is taken, uses Agilent company ZORBAX SB-C18 (4.6 × 250mm, 5 μm) chromatography respectively
Column, Shimadzu Corporation Wonda Cract ODS-2 (4.6 × 250mm, 5 μm) chromatographic column, Agilent company Eclipse XDB-C18
(4.6 × 250mm, 5 μm) chromatographic column, obtains HPLC map, the results showed that changes chromatographic column and does not occur anomaly peak, removes solvent
Peak, with area normalization method measure the content of ar-turmerone is all larger than 99%.It the results are shown in Table 3, Figure 13-15.
3 chromatographic column result of study of table
By adopting the above-described technical solution, the present invention is a kind of using fresh Rhizoma Zingiberis zerumbet underground rhizome as raw material, raw material is mentioned
After taking volatile oil, zerumbone reference substance is prepared by recrystallization method, the zerumbone sterling of prepared acquisition is detected through HPLC,
Be a mass-tone spectral peak in different chromatographic columns and mobile phase measurement result, change chromatographic column and mobile phase measurement do not occur it is different
Chang Feng removes solvent peak, is greater than 99% with area normalization method measurement reference substance purity, meets assay Chemistry for Chinese Traditional Medicine pair
According to the requirement of product.
Detailed description of the invention
Fig. 1 is the HPLC testing result of the product of the embodiment of the present invention；
Fig. 2 is the GC-MS result of dry and fresh Rhizoma Zingiberis zerumbet rhizome volatile oil；
Fig. 3 is zerumbone mass spectrum EI of the invention；
Fig. 4 is zerumbone of the invention1H-NMR；
Fig. 5 is zerumbone of the invention13C-NMR；
Fig. 6 is the blank solvent HPLC map under 5 wavelength；
Fig. 7 is the HPLC map of the zerumbone measured under 5 wavelength；
Fig. 8 is -0.25% acetic acid (70 of acetonitrile:30) the HPLC map of test solution and blank solvent；
Fig. 9 is -0.05% formic acid (80 of methanol:20) the HPLC map of test solution and blank solvent；
Figure 10 is acetonitrile-methanol-water (60:15:25) the HPLC map of test solution and blank solvent；
Figure 11 is acetonitrile-water (80:20) the HPLC map of test solution and blank solvent；
Figure 12 is methanol-water (80:20) the HPLC map of test solution and blank solvent；
Figure 13 is the HPLC map of Agilent ZORBAX SB-C18 (4.6 × 250mm, 5 μm) chromatographic column；
Figure 14 is the HPLC map of Shimadzu Wonda Cract ODS-2 (4.6 × 250mm, 5 μm) chromatographic column；
Figure 15 is the HPLC map of Agilent Eclipse XDB-C18 (4.6 × 250mm, 5 μm) chromatographic column.
Specific embodiment
The embodiment of the present invention：The preparation method of zerumbone reference substance in Rhizoma Zingiberis zerumbet is with fresh Rhizoma Zingiberis zerumbet underground rhizome
Raw material extracts volatile oil, prepares zerumbone reference substance by recrystallization method, comprise the technical steps that：
(1) extraction of Rhizoma Zingiberis zerumbet volatile oil：By fresh Rhizoma Zingiberis zerumbet underground rhizome 500g, after crushing, it is placed in 2L round-bottomed flask
In, by medicinal material and distilled water 1:Distilled water 1000mL is added in 2 solid-liquid ratio, volatile oil extractor is connected, in determination of volatile oil
Appropriate distilled water is added in pipe, and slightly boiled heating 4h collects the water and volatile oil in extractor, through n-hexane extraction, with appropriate anhydrous
It is filtered after sodium sulphate water removal, is concentrated under reduced pressure after removing n-hexane and obtains Rhizoma Zingiberis zerumbet volatile oil 0.51g.
(2) isolated zerumbone reference substance is recrystallized：In Rhizoma Zingiberis zerumbet volatile oil, the n-hexane of 0.3mL is added, 40
It is dissolved by heating in DEG C water-bath, is placed at 15min in -22 DEG C of refrigerators, after precipitating crystal, filters to obtain zerumbone crystal crude product；Again
0.2mL n-hexane is added in zingiberone crystal crude product, is dissolved by heating in 40 DEG C of water-baths, it is lower in -22 DEG C of refrigerators to stand
10min is filtered, and obtains the zerumbone sterling 0.32g that purity is 99% or more.
By the zerumbone sterling of acquisition, detected by HPLC, using acetonitrile and 0.25% acetic acid aqueous solution as mobile phase, acetonitrile
Volume with 0.25% acetic acid aqueous solution is 70:30, column temperature is 48 DEG C, flow velocity 1mL/min, Detection wavelength 280nm, chromatography
Column is Shimadzu Wonda Cract ODS-2 (4.6 × 250mm, 5 μm), and testing result is as shown in Figure 1, purity is 100.00%.
Currently, Rhizoma Zingiberis zerumbet underground rhizome is all after drying as Chinese medicine.But the present invention is with choosing fresh Rhizoma Zingiberis zerumbet
Lower rhizome is raw material, is because the content of zerumbone largely reduces after inventor's discovery Rhizoma Zingiberis zerumbet rhizome drying.Pass through GC-MS
Zerumbone content is measured in the volatile oil extracted to Rhizoma Zingiberis zerumbet rhizome, the results showed that：Fresh content is 70.23%, is done
Dry content is 37.39%.After Rhizoma Zingiberis zerumbet rhizome is dry, the content of zerumbone is largely reduced, and as a result sees Fig. 2.
Claims (2)
1. the preparation method of zerumbone reference substance in a kind of Rhizoma Zingiberis zerumbet, it is characterised in that：It is original with fresh Rhizoma Zingiberis zerumbet underground rhizome
Material extracts volatile oil, prepares zerumbone reference substance by recrystallization method.
2. the preparation method of zerumbone reference substance in Rhizoma Zingiberis zerumbet according to claim 1, it is characterised in that：Including following work
Skill step：
(1) extraction of Rhizoma Zingiberis zerumbet volatile oil：Fresh Rhizoma Zingiberis zerumbet underground rhizome is crushed, the raw material of crushing and distilled water are pressed 1:2-
1:5 solid-liquid ratio mixing, unit g/ml, after mixed material is extracted 2-6h in volatile oil extractor, volatile oil is through n-hexane
Extraction, is filtered after being removed water with anhydrous sodium sulfate, obtains Rhizoma Zingiberis zerumbet volatile oil after removing n-hexane using reduced pressure；
(2) recrystallization isolates and purifies to obtain zerumbone reference substance：To be added n-hexane in Rhizoma Zingiberis zerumbet volatile oil, volatile oil with just oneself
The volume ratio of alkane is 2:1-1:2, it is heated to after being completely dissolved, recrystallizes 5-30min at -30~-15 DEG C, filter to obtain zerumbone
Crystal crude product；N-hexane will be added in zerumbone crystal crude product again, the volume ratio of zerumbone crystal crude product and n-hexane is 2:1-
1:2, it is heated to after being completely dissolved, 5-20min is recrystallized at -30~-15 DEG C, filter, obtain the ball that purity is 99% or more
Zingiberone sterling.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002155001A (en) * | 2000-11-17 | 2002-05-28 | Japan Science & Technology Corp | Perfume substance comprising derivative of zerumbone |
| CN101068559A (en) * | 2004-07-23 | 2007-11-07 | 林忠宗 | Anti-hypersensitive inflammation and anti-allergy activities of zingiber zerumbet (L.) smith |
| US20090239953A1 (en) * | 2006-11-21 | 2009-09-24 | Adel Sharaf Al-Zubairi | Use of an anti-cancer compound |
| BRPI1003607A2 (en) * | 2010-09-23 | 2013-01-08 | Inst Nac De Pesquisas Da Amazonia Inpa | pharmaceutical composition comprising zingiber zerumbet extract and pain reduction process |
| WO2014123406A1 (en) * | 2013-02-06 | 2014-08-14 | Universiti Putra Malaysia | A composition for treating leukemia |
-
2018
- 2018-09-21 CN CN201811107415.3A patent/CN108892608A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002155001A (en) * | 2000-11-17 | 2002-05-28 | Japan Science & Technology Corp | Perfume substance comprising derivative of zerumbone |
| CN101068559A (en) * | 2004-07-23 | 2007-11-07 | 林忠宗 | Anti-hypersensitive inflammation and anti-allergy activities of zingiber zerumbet (L.) smith |
| US20090239953A1 (en) * | 2006-11-21 | 2009-09-24 | Adel Sharaf Al-Zubairi | Use of an anti-cancer compound |
| BRPI1003607A2 (en) * | 2010-09-23 | 2013-01-08 | Inst Nac De Pesquisas Da Amazonia Inpa | pharmaceutical composition comprising zingiber zerumbet extract and pain reduction process |
| WO2014123406A1 (en) * | 2013-02-06 | 2014-08-14 | Universiti Putra Malaysia | A composition for treating leukemia |
Non-Patent Citations (3)
| Title |
|---|
| M.R.SULAIMAN等: "Preliminary analysis of the antinociceptive activity of zerumbone", 《FITOTERAPIA》 * |
| NUR FARHANAH MOHAMAD NOOR等: "Isolation, characterization and modification of zerumbone from Zingiber zerumbet", 《EPROCEEDINGS CHEMISTRY》 * |
| WU YAN等: "Contact and Repellant Activities of Zerumbone and Its Analogues from the Essential Oil of Zingiber zerumbet (L.) Smith against Lasioderma serricorne", 《JOURNAL OF OLEO SCIENCE》 * |
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