CN104478686A - Preparation method of ar-turmerone reference substance in turmeric volatile oil - Google Patents
Preparation method of ar-turmerone reference substance in turmeric volatile oil Download PDFInfo
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- CN104478686A CN104478686A CN201410103616.1A CN201410103616A CN104478686A CN 104478686 A CN104478686 A CN 104478686A CN 201410103616 A CN201410103616 A CN 201410103616A CN 104478686 A CN104478686 A CN 104478686A
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- ethyl acetate
- reference substance
- petroleum ether
- turmerone
- volatile oil
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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
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Abstract
The invention discloses a preparation method of an ar-turmerone reference substance in turmeric volatile oil. According to the invention, turmeric volatile oil is used as a raw material, silica gel column chromatography and preparative high performance liquid chromatography are used as separation methods, and petroleum ether-ethyl acetate and methanol-water are proportionally used as an elution system. It is determined that the prepared ar-turmerone pure product has a main chromatographic peak at different chromatographic columns and mobile phases through HPLC detection, and no anomaly peak appears when chromatographic columns and mobile phases are changed. By an area normalization method, purity of the reference substance is greater than 99%, thus meeting requirements of a traditional Chinese medicinal chemical reference substance in content determination.
Description
Technical field
The present invention relates to a kind of separating and purifying technology, the preparation method of aryl turmerone reference substance in especially a kind of Rhizoma Curcumae Longae volatile oil.
Background technology
Turmeric is the dry rhizome of Zingiber turmeric (Curcuma) plant turmeric.Turmeric is as traditional Chinese medicine, and begin to be loaded in Tang Materia Medica, have broken blood gas, inducing meastruation to relieve menalgia function, modern medicine study shows, turmeric has anti-inflammatory, anti-oxidant, scavenging free radicals, antimicrobial and antitumor action.It is used to treatment hyperlipidemia and has anti-liver toxicity in recent years.
Aryl turmerone is as a kind of important component of turmeric, belong to terpene compound, research in medical science relates to the effect such as inducing apoptosis of tumour cell, resisting gram-positive bacteria and Gram-negative bacteria, antimycotic, antifertility, antisnake venom, all holds out broad prospects to clinical development treatment leukemia, malignant lymphoma, bacterial inflammation, fungi inflammation, the even aspect such as the Metabolic syndrome such as diabetes, obesity disease and birth control.
The effective constituent of eliminating acne turmeric liniment is Rhizoma Curcumae Longae volatile oil, and volatilization main body of oil is aryl turmerone.Measuring eliminating acne turmeric liniment quality control system using aryl turmerone as its functional attributes to ensureing curative effect further, strengthening quality controllability significant.From Rhizoma Curcumae Longae volatile oil, how to obtain highly purified aryl turmerone reference substance, be need to solve.
Summary of the invention
Technical problem to be solved by this invention is to provide the preparation method of aryl turmerone reference substance in a kind of Rhizoma Curcumae Longae volatile oil, and it can be separated the aryl turmerone obtaining very high purity from Rhizoma Curcumae Longae volatile oil.
The present invention is achieved in that the preparation method of aryl turmerone reference substance in Rhizoma Curcumae Longae volatile oil, take Rhizoma Curcumae Longae volatile oil as raw material, comprises following processing step:
(1) pressurization normal phase silicagel column roughing out: mass ratio raw material and silica gel being pressed 1:10-1:15, be that the petroleum ether-ethyl acetate of 30:1-15:1 carries out gradient elution for eluent with volume ratio, pressurized column chromatography, by a thin layer plate, launch with petroleum ether-ethyl acetate, the volume ratio of sherwood oil and ethyl acetate is 15:1-25:1, observes under ultraviolet, the mixture of collector similar temperament, is separated and obtains roughing out thing;
(2) pressurize normal phase silicagel column segmentation from: roughing out thing is added silica gel, the raw material added first and segmentation from the mass ratio of silica gel be 1:10-1:15, be that the petroleum ether-ethyl acetate of 100:1-50:1 carries out gradient elution for eluent with volume ratio, pressurized column chromatography, by a thin layer plate, launches with petroleum ether-ethyl acetate, the volume ratio of sherwood oil and ethyl acetate is 25:1-15:1, observe under ultraviolet, collect polarity mixture closely, be separated and obtain thin isolate;
(3) preparative high-performance liquid chromatographic is separated and obtains aryl turmerone reference substance: add acetone by thin isolate, the volume ratio of thin isolate and acetone is 1: 5-1:10, with first alcohol and water for moving phase, the volume of methyl alcohol and water is 60:40-90:10, flow velocity is 5-10 mL/min, within 15-17 minute, go out peak, 20-22 minute terminates, and collects and obtains the aryl turmerone sterling that purity is more than 99%.
In order to verify technique effect of the present invention further, carry out following experiment:
The separation of aryl turmerone monomeric compound
1.1 silica gel column chromatography roughing out
Take Rhizoma Curcumae Longae volatile oil 10 g, with petroleum ether dissolution in evaporating dish, with 12 g silica gel mixed samples, volatilize solvent, for subsequent use; By 1:10 with 100 g silica gel (300-400 order), with petroleum ether-ethyl acetate (15:1) wet method upper prop; Loading again after layer of silica gel in post no longer moves down, and carry out pressurization wash-out, by a thin layer plate with petroleum ether-ethyl acetate (15:1), launch with petroleum ether-ethyl acetate (15:1), observe under 254nm, collect the mixture that Rf 0.7 place polarity is close, obtain 7.3g.
1.2 silica gel column chromatographies segmentation from
Take mixture 7.3 g that roughing out obtains, with petroleum ether dissolution in evaporating dish, with 10 g silica gel mixed samples, volatilize solvent, for subsequent use; With 110 g silica gel (300-400 order), with petroleum ether-ethyl acetate (50:1) wet method upper prop; Loading again after layer of silica gel in post no longer moves down, and carry out pressurization wash-out, by a thin layer plate with petroleum ether-ethyl acetate (50:1), launch with petroleum ether-ethyl acetate (25:1), observe under 254 nm, collect Rf 0.5 place polarity mixture closely, obtain 5.2 g.
Detected by HPLC being separated the mixture obtained.HPLC condition is pillar Hedera C
18(200 mm), mobile phase methanol-water (90:10), column temperature 25 DEG C, determined wavelength 254 nm, sample size 15 μ L, measurement result as shown in Figure 2, finds that mixture is 3 components, is decided to be 1 respectively from left to right, 2,3.
1.3 preparative high performance liquid phase are separated
Prepared by liquid phase, with Agilent company Agilent ZORBAX SB-C from three components obtained by using Agilent 1260 type to silica gel column chromatography segmentation
18(21.2 × 250 mm, 5 μm) chromatographic column is separated, and gets silica gel column chromatography segmentation from mixture 1 mL obtained, be dissolved in 5 mL methyl alcohol and dilute, moving phase chooses methanol-water respectively: 95:5,90:10,85:75,80:20,75:25, flow velocity chooses 2 mL/min respectively, 5 mL/min, 8 mL/min, 10 mL/min, 12 mL/min, therefrom determine Optimum separation condition.Finally determine that Optimum separation condition moving phase is methanol-water (80:20), flow velocity 10 mL/min.Collect 3 components respectively, through Rotary Evaporators, solvent is spin-dried for, obtain purified product 1,2,3, through MS,
1h-NMR,
13c-NMR measures.
1.4 conclusion
By MS,
1h-NMR,
13c-NMR measures, and finally determines that 1 for aryl turmerone.MS measures, and is 98% with the aryl turmerone Data Matching rate in spectrum storehouse;
1h-NMR,
13it is correct that C-NMR measures structure,
1h NMR (CDCl
3, 400 MHz) δ: 1.17 (d,
j=7.2 Hz, 3H), 1.78 (d,
j=1.2 Hz, 3H), 2.03 (d,
j=0.8 Hz, 3H), 2.23 (s, 3H), 2.50-2.56 (m, 1H), 2.61-2.66 (m, 1H), 3.19-3.24 (m, 1H), 5.95 (t,
j=1.2 Hz, 1H), 7.03 (d,
j=1.2 Hz, 4H);
13c NMR (CDCl
3, 100 MHz) and δ: 20.72,20.99,22.00,27.65,35.30,52.70,124.11,126.68,129.12,135.56,143.71,155.10,199.89.Result is as shown in Fig. 3, Fig. 4 and Fig. 5.
2.1 high performance liquid chromatography-purity test
Adopt Agilent 1260 type high performance liquid chromatograph (quaternary pump, automatic sampler, column oven, DAD UV-detector, ChemStation chromatographic working station), with Han Bang company Hedera C
18(4.6 × 200 mm, 5 μm) chromatographic column, column temperature 25 DEG C, moving phase is methanol-water (80:20), it is 190 ~ 400 nm that DAD sets wavelength region, setting 204,220,254,280,310 nm five determined wavelength, and observe the detection case of other wavelength, to investigate the purity of aryl turmerone simultaneously.
Get aryl turmerone appropriate, the solution of every 1 mL containing 1 mg is made with methyl alcohol, as need testing solution, get blank solvent (methyl alcohol) and each 10 μ L of need testing solution, injection liquid chromatography respectively, after the chromatographic peak that result deduction blank solvent produces, the chromatographic peak area normalization method content of aryl turmerone is all greater than more than 99%, in table 1, Fig. 6 and Fig. 7 under each wavelength.
2.2 moving phases are investigated
Get aryl turmerone test liquid, acetonitrile-water (80:20), methanol-water (80:20), methyl alcohol-0.05% phosphate aqueous solution (80:20), methyl alcohol-0.1% phosphate aqueous solution (80:20), methyl alcohol-0.3% phosphate aqueous solution (80:20) is used to be moving phase respectively, obtain HPLC collection of illustrative plates, all there is not anomaly peak under showing each moving phase condition in result, measures the content of aryl turmerone under each moving phase condition be all greater than 99% with area normalization method.The results are shown in Table 2, Fig. 8-12.
The investigation of 2.3 pillars
Get aryl turmerone test liquid, use Hedera C respectively
18(4.6 × 200 mm, 5 μm) chromatographic column, Agilent C
8(4.6 × 150 mm, 5 μm) chromatographic column, Waters C
18(4.6 × 250 mm, 5 μm) chromatographic column, obtains HPLC collection of illustrative plates, and result shows that changing chromatographic column does not all occur anomaly peak, measures the content of aryl turmerone is all greater than 99% with area normalization method.The results are shown in Table 3, Figure 13-15.
Owing to have employed technique scheme, compared with prior art, the present invention take Rhizoma Curcumae Longae volatile oil as raw material, with silica gel column chromatography and preparative high performance liquid chromatography for separation means, with a certain proportion of petroleum ether-ethyl acetate, methanol-water is eluent system, the prepared aryl turmerone sterling obtained, detect through HPLC, a main chromatographic peak is in different chromatographic column and moving phase measurement result, change chromatographic column and moving phase measure and all do not occur anomaly peak, measure reference substance purity with area normalization method and be greater than 99%, meet the requirement of assay traditional Chinese chemical contrast.
Accompanying drawing explanation
Fig. 1 is the HPLC detected result of the product of embodiments of the invention;
Fig. 2 is that thin separating mixture HPLC of the present invention measures collection of illustrative plates;
Fig. 3 is aryl turmerone mass spectrum EI of the present invention;
Fig. 4 is aryl turmerone of the present invention
1h-NMR;
Fig. 5 is aryl turmerone of the present invention
13c-NMR;
Fig. 6 is the blank solvent HPLC collection of illustrative plates under 5 wavelength;
Fig. 7 is the HPLC collection of illustrative plates of the aryl turmerone measured under 5 wavelength;
Fig. 8 is the HPLC collection of illustrative plates of acetonitrile-water 80:20;
Fig. 9 is the HPLC collection of illustrative plates of methanol-water 80:20;
Figure 10 is the HPLC collection of illustrative plates of methyl alcohol-0.05% phosphate aqueous solution 80:20;
Figure 11 is the HPLC collection of illustrative plates of methyl alcohol-0.1% phosphate aqueous solution 80:20;
Figure 12 is the HPLC collection of illustrative plates of methyl alcohol-0.3% phosphate aqueous solution 80:20;
Figure 13 is Hedera C
18(4.6 × 200 mm, 5 μm) chromatographic column;
Figure 14 is Agilent C
8(4.6 × 150 mm, 5 μm) chromatographic column;
Figure 15 is Waters C
18(4.6 × 250 mm, 5 μm) chromatographic column.
Embodiment
Embodiments of the invention: the preparation method of aryl turmerone reference substance in Rhizoma Curcumae Longae volatile oil take Rhizoma Curcumae Longae volatile oil as raw material, comprises following processing step:
(1) pressurization normal phase silicagel column roughing out: 10g Rhizoma Curcumae Longae volatile oil is added 300-400 object silica gel 100g, take volume ratio as the petroleum ether-ethyl acetate of 15:1 be eluent, pressurized column chromatography, by a thin layer plate, launch with petroleum ether-ethyl acetate (15:1), observe under 254nm, collect the mixture that Rf 0.7 place polarity is close, i.e. roughing out thing is 7.3g;
(2) pressurize normal phase silicagel column segmentation from: 300-400 object silica gel 110g will be added in 7.3g roughing out thing, take volume ratio as the petroleum ether-ethyl acetate of 50:1 be eluent, pressurized column chromatography, by a thin layer plate, launch with petroleum ether-ethyl acetate (25:1), observe under 254 nm, collect Rf 0.5 place polarity mixture closely,, namely thin isolate, is 5.2g;
(3) preparative high-performance liquid chromatographic is separated and obtains aryl turmerone reference substance: add acetone by thin isolate, the thin isolate of every 1ml adds 5ml acetone and dilutes, each sample introduction 0.4 mL, with first alcohol and water for moving phase, the volume of methyl alcohol and water is 80:20, and flow velocity is 10 mL/min, within 16 minutes, goes out peak, 21 minutes terminate, and once obtain aryl turmerone sterling 30 mg.
By the aryl turmerone sterling obtained, detected by HPLC, with first alcohol and water for moving phase, the volume of methyl alcohol and water is 80:20, and column temperature is 25 DEG C, and flow velocity is 0.8ml/min, and determined wavelength is 242nm, and pillar is Hederac C
18200mm, detect and met as shown in Figure 1, purity is 99.95%.
Claims (1)
1. the preparation method of aryl turmerone reference substance in Rhizoma Curcumae Longae volatile oil, is characterized in that: be raw material with Rhizoma Curcumae Longae volatile oil, comprises following processing step:
(1) pressurization normal phase silicagel column roughing out: mass ratio raw material and silica gel being pressed 1:10-1:15, be that the petroleum ether-ethyl acetate of 30:1-15:1 carries out gradient elution for eluent with volume ratio, pressurized column chromatography, by a thin layer plate, launch with petroleum ether-ethyl acetate, the volume ratio of sherwood oil and ethyl acetate is 25:1-15:1, observes under ultraviolet, the mixture of collector similar temperament, is separated and obtains roughing out thing;
(2) pressurize normal phase silicagel column segmentation from: roughing out thing is added silica gel, the raw material added first and segmentation from the mass ratio of silica gel be 1:10-1:15, be that the petroleum ether-ethyl acetate of 100:1-50:1 carries out gradient elution for eluent with volume ratio, pressurized column chromatography, by a thin layer plate, launches with petroleum ether-ethyl acetate, the volume ratio of sherwood oil and ethyl acetate is 25:1-15:1, observe under ultraviolet, collect polarity mixture closely, be separated and obtain thin isolate;
(3) preparative high-performance liquid chromatographic is separated and obtains aryl turmerone reference substance: add acetone by thin isolate, the volume ratio of thin isolate and acetone is 1: 5-1:10, with first alcohol and water for moving phase, the volume of methyl alcohol and water is 60:40-90:10, flow velocity is 5-10 mL/min, collects and obtains the aryl turmerone sterling that purity is more than 99%.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107441071A (en) * | 2017-06-30 | 2017-12-08 | 广东工业大学 | A kind of application of ar-turmerone in treatment and/or prevention psoriasis is prepared |
| CN110051550A (en) * | 2019-05-30 | 2019-07-26 | 佛山市康伲爱伦生物技术有限公司 | A kind of ar-turmerone inclusion compound and preparation method thereof with sterilization anti-inflammatory effect |
| CN110724044A (en) * | 2019-10-28 | 2020-01-24 | 珠海安哲生物科技有限公司 | Preparation method of arylturmerone reference substance |
| CN111484403A (en) * | 2020-06-10 | 2020-08-04 | 珠海安哲生物科技有限公司 | Preparation method of arylturmerone reference substance |
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| CN102659549A (en) * | 2012-04-01 | 2012-09-12 | 贵州威门药业股份有限公司 | Method for extracting brevifolin from Relinqing granula raw material and method for preparation quality control |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107441071A (en) * | 2017-06-30 | 2017-12-08 | 广东工业大学 | A kind of application of ar-turmerone in treatment and/or prevention psoriasis is prepared |
| CN107441071B (en) * | 2017-06-30 | 2019-10-22 | 广东工业大学 | A kind of application of ar-turmerone in preparation treatment and/or prevention psoriasis |
| CN110051550A (en) * | 2019-05-30 | 2019-07-26 | 佛山市康伲爱伦生物技术有限公司 | A kind of ar-turmerone inclusion compound and preparation method thereof with sterilization anti-inflammatory effect |
| CN110724044A (en) * | 2019-10-28 | 2020-01-24 | 珠海安哲生物科技有限公司 | Preparation method of arylturmerone reference substance |
| CN111484403A (en) * | 2020-06-10 | 2020-08-04 | 珠海安哲生物科技有限公司 | Preparation method of arylturmerone reference substance |
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Inventor after: Wang Huijuan Inventor after: Zhou Ying Inventor after: Guo Donggui Inventor after: Pan Bowen Inventor after: Shi Yang Inventor after: Cui Kai Inventor after: Liu Xiongli Inventor before: Zhou Ying Inventor before: Pan Bowen Inventor before: Shi Yang Inventor before: Wang Huijuan Inventor before: Cui Kai Inventor before: Liu Xiongli |
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Effective date of registration: 20201109 Address after: 533000 Donghai Industrial Park, Tiandong County, Baise City, Guangxi Zhuang Autonomous Region Patentee after: Guangxi Mojiang biopharmaceutical Co., Ltd Address before: 550025 science and Technology Department, north campus, Guizhou University, Huaxi, Guizhou, China Patentee before: Guizhou University |