CN105237378A - Method for separating germacrone from Curcuma wenyujin volatile oil - Google Patents
Method for separating germacrone from Curcuma wenyujin volatile oil Download PDFInfo
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- CN105237378A CN105237378A CN201510642696.2A CN201510642696A CN105237378A CN 105237378 A CN105237378 A CN 105237378A CN 201510642696 A CN201510642696 A CN 201510642696A CN 105237378 A CN105237378 A CN 105237378A
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- germacrone
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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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention discloses a method for separating germacrone from Curcuma wenyujin volatile oil. The method comprises the following steps: fully mixing an aqueous solution of methyl-beta-cyclodextrin with n-hexane according to a volume ratio of 1:0.5-2, standing, carrying out liquid separation to respectively obtain an upper phase which is a mobile phase and a lower phase which is the stationary phase of a high-speed countercurrent chromatograph; and weighing the Curcuma wenyujin volatile oil, dissolving the Curcuma wenyujin volatile oil in a mixture containing the upper phase and the lower phase according to a volume ratio of 1:1, introducing the above obtained sample, carrying out high-speed countercurrent chromatographic separation, detecting through an ultraviolet detector, collecting corresponding effluents corresponding to peaks in the spectrogram of the ultraviolet detector, concentrating germacrone-containing effluents, and drying to prepare pure germacrone. The method has the advantages of simple operation, less solvent consumption, high efficiency, fastness, strong purposefulness and good separation effect.
Description
(1) technical field
The invention belongs to field of traditional Chinese medicine pharmacy, relate to a kind of method being separated germacrone from the essential oil from Curcuma wenyujin being rich in germacrone.
(2) technical background
Germacrone is a kind of monocyclic sesquiterpene compounds be present in the essential oil from Curcuma wenyujin, for antiasthmatic effect, suppresses liver cancer BEL7402 cell proliferation.Germacrone, English germacrone, molecular formula C by name
15h
22o, molecular weight 218.33, molecular structure is as follows:
RADIX CURCUMAE has that promoting the circulation of qiization is tired, effect of heart fire-clearing upset-relieving, promoting the function of the gallbladder to alleviate jaundice, be mainly used in treatment through closing, dysmenorrhoea, abdominal distention and pain, shouting pain, pyreticosis, the diseases such as go mad in pain top, yellow subcutaneous ulcer urine is red.At present, the extraction of germacrone is mainly through silica gel column chromatography wash-out.General adverse current chromatogram separation method, obtain target compound germacrone length consuming time, cost is high.
(3) summary of the invention
Technical problem to be solved by this invention is just to provide a kind of method of sharp separation germacrone, and the present invention utilizes the Inclusion property of cyclodextrin and germacrone, is separated by germacrone fast from the essential oil from Curcuma wenyujin, has stronger purpose, quickness and high efficiency.
Technical scheme of the present invention is:
A kind of method being separated germacrone from the essential oil from Curcuma wenyujin, described method is: the methyl-B-cyclodextrin aqueous solution is fully mixed rear standing, separatory in 1:0.5 ~ 2 by volume with normal hexane, obtain upper and lower phase respectively, the lower stationary phase as high speed adverse current chromatogram, upper is moving phase mutually; Take the essential oil from Curcuma wenyujin, sample introduction after dissolving by the upper and lower phase of volume ratio 1:1, high speed adverse current chromatogram is separated, UV-detector detects, corresponding effluent liquid is collected according to the peak shape of UV-detector spectrogram, by the effluent liquid concentrate drying containing germacrone, obtained germacrone sterling.
The concentration of the described methyl-B-cyclodextrin aqueous solution is 0.05-0.2mol/L, preferably 0.05 ~ 0.1mol/L.
The volume ratio of the described methyl-B-cyclodextrin aqueous solution and normal hexane is 1:0.5 ~ 2, preferred 1:1.
The column temperature of described high speed adverse current chromatogram is 15 DEG C ~ 30 DEG C, preferably 20 DEG C.
Described method is preferably by following operation: the methyl-B-cyclodextrin aqueous solution of 0.05 ~ 0.2mol/L is fully mixed rear standing, separatory in 1:0.5 ~ 2 by volume with normal hexane, obtain upper and lower phase respectively, the lower stationary phase as high speed adverse current chromatogram, upper is moving phase mutually, first stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, setting high-speed counter current chromatograph, column temperature 15 DEG C ~ 30 DEG C (preferably 20 DEG C), be rotated counterclockwise under 500 ~ 1000r/min rotating speed (preferred 800r/min rotating speed), moving phase is injected with the flow velocity of 0.5 ~ 5ml/min (preferred 2ml/min), detect with the UV-detector of wavelength 200-300nm (preferably 210 ~ 254nm), when post tail end obviously has moving phase to flow out, take the essential oil from Curcuma wenyujin, sample introduction after dissolving by the upper and lower phase of volume ratio 1:1, corresponding effluent liquid is collected according to the peak shape of UV-detector spectrogram, by the effluent liquid concentrate drying containing germacrone, obtained germacrone sterling.
Further, described method is more preferably by following operation: by the methyl-B-cyclodextrin aqueous solution of 0.05 ~ 0.1mol/L and normal hexane by volume 1:1 fully mix to leave standstill afterwards, separatory, obtain upper and lower phase respectively, the lower stationary phase as high speed adverse current chromatogram, upper is moving phase mutually; First stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, setting high-speed counter current chromatograph, column temperature 20 DEG C, be rotated counterclockwise under 800 ~ 1000r/min rotating speed, moving phase is injected with the flow velocity of 2ml/min, detect with the UV-detector of wavelength 210 ~ 254nm, when post tail end obviously has moving phase to flow out, take the essential oil from Curcuma wenyujin, sample introduction after dissolving by the upper and lower phase of volume ratio 1:1, corresponding effluent liquid is collected according to the peak shape of UV-detector spectrogram, by the effluent liquid concentrate drying containing germacrone, obtained germacrone sterling.
Generally the upper and lower phase mixed solvent of the essential oil from Curcuma wenyujin of 100-1000mg with the volume ratio 1:1 of 15 ~ 20mL is dissolved, then sample introduction.
Compared with the prior art, the advantage that the present invention has is: the present invention is easy and simple to handle, efficient quick, and solvent consumption is few; Methyl-B-cyclodextrin has exclusive Inclusion property to germacrone, and purpose is strong, and separating effect is outstanding.
(4) accompanying drawing explanation
High speed adverse current chromatogram (HSCCC) figure of Fig. 1 embodiment 1.
High speed adverse current chromatogram (HSCCC) figure of Fig. 2 embodiment 2.
High speed adverse current chromatogram (HSCCC) figure of Fig. 3 embodiment 3.
The nucleus magnetic hydrogen spectrum figure of Fig. 4 germacrone.
In Fig. 1 ~ Fig. 3, No. 2 peaks represent germacrone.
(5) embodiment
With specific embodiment, technical scheme of the present invention is described further below, but protection scope of the present invention is not limited thereto.In following embodiment, the high speed adverse current chromatogram model of employing is: HSCCC-TBE200V
Embodiment 1:
The preparation 0.1mol/L methyl-B-cyclodextrin aqueous solution and normal hexane by volume 1:1 mix in separating funnel, fully vibrate, static, layering before use, elect stationary phase as mutually down, above elect moving phase as mutually; Column temperature is set as 20 DEG C, first with the lower polytetrafluoroethylhelix helix tube of mutually squeezing into HSCCC of constant flow pump by solvent system, until fill whole pipe, then HSCCC is opened, be rotated counterclockwise, rotating speed is 803.6prm, moving phase is pumped into HSCCC separator column with 2.0ml/min flow velocity from the head end of post simultaneously; By the time, when post tail end flows out moving phase, show that in HSCCC, two-phase reaches balance, by six-way valve, sample is injected HSCCC (phase solvent up and down that 536.4mg the essential oil from Curcuma wenyujin sample dissolution mixes in 18ml equal-volume); Detect effluent liquid with the UV-detector of wavelength 254nm, according to UV-detector spectrogram, see Fig. 1, in Fig. 1, No. 2 peaks represent germacrone, automatically collect elutriant, are volatilized by the solvent of the elutriant at corresponding peak, obtain germacrone crystal 11mg.The nucleus magnetic hydrogen spectrum figure of germacrone is shown in Fig. 4.
Embodiment 2:
The preparation 0.1mol/L methyl-B-cyclodextrin aqueous solution and normal hexane by volume 1:1 mix in separating funnel, fully vibrate, static, layering before use, elect stationary phase as mutually down, above elect moving phase as mutually; Column temperature is set as 20 DEG C, first with the lower polytetrafluoroethylhelix helix tube of mutually squeezing into HSCCC of constant flow pump by solvent system, until fill whole pipe, then HSCCC is opened, be rotated counterclockwise, rotating speed is 803.6prm, moving phase is pumped into HSCCC separator column with 2.0ml/min flow velocity from the head end of post simultaneously; By the time, when post tail end flows out moving phase, show that in HSCCC, two-phase reaches balance, by six-way valve, sample is injected HSCCC (phase solvent up and down that 905.5mg the essential oil from Curcuma wenyujin sample dissolution mixes in 18ml equal-volume); Detect effluent liquid with the UV-detector of wavelength 254nm, according to UV-detector spectrogram, see Fig. 2, in Fig. 2, No. 2 peaks represent germacrone, automatically collect elutriant, are volatilized by the solvent of the elutriant at corresponding peak, obtain germacrone crystal 21mg.
Embodiment 3:
The preparation 0.05mol/L methyl-B-cyclodextrin aqueous solution and normal hexane by volume 1:1 mix in separating funnel, fully vibrate, static, layering before use, elect stationary phase as mutually down, above elect moving phase as mutually; Column temperature is set as 20 DEG C, first with the lower polytetrafluoroethylhelix helix tube of mutually squeezing into HSCCC of constant flow pump by solvent system, until fill whole pipe, then HSCCC is opened, be rotated counterclockwise, rotating speed is 802.5prm, moving phase is pumped into HSCCC separator column with 2.0ml/min flow velocity from the head end of post simultaneously; By the time, when post tail end flows out moving phase, show that in HSCCC, two-phase reaches balance, by six-way valve, sample is injected HSCCC (phase solvent up and down that 429.8mg the essential oil from Curcuma wenyujin sample dissolution mixes in 18ml equal-volume); In Fig. 3, No. 2 peaks represent germacrone, automatically collect elutriant, are volatilized by the solvent of the elutriant at corresponding peak, obtain germacrone crystal 9mg.
Claims (7)
1. one kind is separated the method for germacrone from the essential oil from Curcuma wenyujin, it is characterized in that described method is: the methyl-B-cyclodextrin aqueous solution is fully mixed rear standing, separatory in 1:0.5 ~ 2 by volume with normal hexane, obtain upper and lower phase respectively, the lower stationary phase as high speed adverse current chromatogram, upper is moving phase mutually; Take the essential oil from Curcuma wenyujin, sample introduction after dissolving by the upper and lower phase of volume ratio 1:1, high speed adverse current chromatogram is separated, UV-detector detects, corresponding effluent liquid is collected according to the peak shape of UV-detector spectrogram, by the effluent liquid concentrate drying containing germacrone, obtained germacrone sterling.
2. the method for claim 1, is characterized in that the concentration of the described methyl-B-cyclodextrin aqueous solution is 0.05-0.2mol/L.
3. the method for claim 1, is characterized in that the volume ratio of the described methyl-B-cyclodextrin aqueous solution and normal hexane is 1:1.
4. method as claimed in claim 2, is characterized in that the concentration of the described methyl-B-cyclodextrin aqueous solution is 0.05 ~ 0.1mol/L.
5. the method for claim 1, is characterized in that the column temperature of described high speed adverse current chromatogram is 15 DEG C ~ 30 DEG C.
6. the method for claim 1, it is characterized in that method is by following operation: the methyl-B-cyclodextrin aqueous solution of 0.05 ~ 0.2mol/L is fully mixed rear standing, separatory in 1:0.5 ~ 2 by volume with normal hexane, obtain upper and lower phase respectively, the lower stationary phase as high speed adverse current chromatogram, upper is moving phase mutually, first stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, setting high-speed counter current chromatograph, column temperature 15 DEG C ~ 30 DEG C, be rotated counterclockwise under 500 ~ 1000r/min rotating speed, moving phase is injected with the flow velocity of 0.5 ~ 5ml/min, detect with the UV-detector of wavelength 200-300nm, when post tail end obviously has moving phase to flow out, take the essential oil from Curcuma wenyujin, sample introduction after dissolving by the upper and lower phase of volume ratio 1:1, corresponding effluent liquid is collected according to the peak shape of UV-detector spectrogram, by the effluent liquid concentrate drying containing germacrone, obtained germacrone sterling.
7. method as claimed in claim 6, it is characterized in that method is by following operation: by the methyl-B-cyclodextrin aqueous solution of 0.05 ~ 0.1mol/L and normal hexane by volume 1:1 fully mix to leave standstill afterwards, separatory, obtain upper and lower phase respectively, the lower stationary phase as high speed adverse current chromatogram, upper is moving phase mutually; First stationary phase is full of the multilayer coil separator column of high-speed counter-current chromatograph, setting high-speed counter current chromatograph, column temperature 20 DEG C, be rotated counterclockwise under 800 ~ 1000r/min rotating speed, moving phase is injected with the flow velocity of 2ml/min, detect with the UV-detector of wavelength 210 ~ 254nm, when post tail end obviously has moving phase to flow out, take the essential oil from Curcuma wenyujin, sample introduction after dissolving by the upper and lower phase of volume ratio 1:1, corresponding effluent liquid is collected according to the peak shape of UV-detector spectrogram, by the effluent liquid concentrate drying containing germacrone, obtained germacrone sterling.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108714117A (en) * | 2018-07-06 | 2018-10-30 | 山东煜煌信息咨询有限公司 | A kind of long-acting perfume and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973861A (en) * | 2010-07-26 | 2011-02-16 | 南京泽朗医药科技有限公司 | Method for preparing germacrone |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101973861A (en) * | 2010-07-26 | 2011-02-16 | 南京泽朗医药科技有限公司 | Method for preparing germacrone |
Non-Patent Citations (3)
| Title |
|---|
| JIZHONG YAN ET AL.: "Preparative isolation and purification of germacrone and curdione from the essential oil of the rhizomes of Curcuma wenyujin by high-speed counter-current chromatography", 《JOURNAL OF CHROMATOGRAPHY A》 * |
| SHENGQIANG TONGA ET AL.: "Selective isolation of components from natural volatile oil by countercurrent chromatography with cyclodextrins as selective reagent", 《JOURNAL OF CHROMATOGRAPHY A》 * |
| YUAN-YE DANG ET AL.: "Preparative isolation and purification of six volatile compounds from essential oil of Curcuma wenyujin using high-performance centrifugal partition chromatography", 《J. SEP. SCI.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108714117A (en) * | 2018-07-06 | 2018-10-30 | 山东煜煌信息咨询有限公司 | A kind of long-acting perfume and preparation method thereof |
| CN108714117B (en) * | 2018-07-06 | 2021-04-27 | 浙江丽芙秀化妆品有限公司 | Long-acting perfume and preparation method thereof |
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