CN100999536A - Process of simultaneously extracting and detecting cornus cyclic olefine ether terpinyl side like extractive - Google Patents
Process of simultaneously extracting and detecting cornus cyclic olefine ether terpinyl side like extractive Download PDFInfo
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Abstract
The present invention relates to simultaneous extraction and measurement of iridoid glycosides from dogwood, and is especially process of simultaneously extracting and measuring six kinds of iridoid glycoside compound. Compared with available technology, the present invention has the advantages of simple extraction process, high efficiency, low cost, fast and effective detection, etc.
Description
Technical field
The present invention relates to a kind of cornus cyclic olefine ether terpinyl side like extractive and extract simultaneously and detection method, belong to technical field of traditional Chinese medicines.
Technical background
Skunk bush (Cornus officinalis Sieb.et Zucc.), another name another name for Sichuan Province jujube, mouse arrow, chicken foot, Fructus Corni, real jujube, fructus corni and cornus etc., all there are distribution and cultivation in ground such as China Zhejiang, Henan, Shandong, Anhui, Jiangsu, Shanxi, Shaanxi, Sichuan.Its flavor acid of skunk bush, puckery, slightly warm in nature is returned the liver kidney channel, have tonify the liver and kidney, effect that puckery essence is taken off admittedly.Cure mainly under dizzy tinnitus, soreness of waist and knee joint, impotence and seminal emission, enuresis frequent micturition, the uterine bleeding band, profuse sweating collapse, interior heat quench one's thirst.Have tonify the liver and kidney, effect that puckery essence is taken off admittedly, be one of tcm clinical practice famous and precious traditional medicinal material commonly used.
China just has skunk bush to be applied to the record of diabetes (traditional Chinese medical science is called " diabetes ") treatment from ancient times.Chinese scholars is studied its composition, and modern pharmacology studies show that skunk bush iridoid glycosides material is the main reactive site of hypoglycemic.Xu Huiqin etc. (Nanjing University of Traditional Chinese Medicine's journal, Vol.19 (6), 2003, P342～344) have studied the provide protection that the skunk bush iridoid glycoside becomes the artificial diabetes ephrosis; Pi Wenxia etc. (new Chinese medicine and clinical pharmacology, Vol.14 (1), 2003, P23～24) have reported the influence of skunk bush iridoid glycoside to diabetic vascular complications rat model SOD in serum.
There is report to think, the iridoid glycoside compounds has 10 in the known skunk bush, what content was the highest is loganin (loganin), morroniside (morroniside), other contains sweroside (sweroside), 7-Methylmorroniside (doubt and be the secondary metabolite in the leaching process), 7-oxyethyl group morroniside (may be because alcoholic acid extraction, the also secondary pollutant that may produce because of the process of preparing Chinese medicine of wine).Dehydration Monot aglycon, 7-dehydrogenation loganin (7-dehydrologanin), cornin (comin, i.e. verbenaloside verbenalin), the new glycosides I of skunk bush, II (comuside I, II) (Pan Yang etc., Nanjing University of Traditional Chinese Medicine's journal: Vol.14 (1), 1998, P61).Separated first from skunk bush by Tohru Endo etc. in 1973 and obtain iridoid glycosides monomeric compound-morroniside (Japan " pharmaceutical journal " Vol.93, P30～32).Method in the literary composition is to go up activated carbon column behind the methanol extraction, and through silica gel column chromatography, the chloroform-methanol gradient elution obtains morroniside.Chen Yu forces in 1992 etc. are also separated from dogwood meat processed and have been obtained morroniside (China-Japan Friendship Hospital's journal, Vol.6, P231～234).Method in the literary composition is to go up macroporous adsorptive resins behind the water extraction, through silica gel column chromatography, obtains morroniside.Chinese patent 200410014771.2 discloses the preparation method and the purposes of Fructus Corni extract morroniside.But existing these separating steps are loaded down with trivial details, in leaching process loss bigger, and can only obtain part iridoid glycosides monomeric substance, can not represent the effective substance of curing the disease.Up to now, do not see as yet when skunk bush iridoid glycosides material is arranged yet and to extract and the report of detection method.
Summary of the invention
The objective of the invention is to overcome pretreatment operation complexity in the prior art, can not extract and detect the defective of several iridoid glucosides compounds simultaneously, provide a kind of cornus cyclic olefine ether terpinyl side like extractive to extract simultaneously and detection method.
1, a kind of cornus cyclic olefine ether terpinyl side like extractive of the present invention extracts and detection method simultaneously, obtains by following step:
(1) the skunk bush medicinal material is made only, promptly removed impurity and residual fruit stone, carpopodium, obtain clean skunk bush.
(2) clean skunk bush being added concentration of volume percent is 20%～90% ethanol, after 8～30 times of amounts are soaked, and refluxing extraction 2～4 times, with little degree of being that boils, each return time is 0.5～1 hour, filters.
(3) merging filtrate is evaporated to nothing alcohol flavor with Rotary Evaporators, gets concentrated solution.
(4) concentrated solution is added ethanol and transfer to and make that to contain the amount of alcohol concentration expressed in percentage by volume be 50%～90, refrigeration was left standstill 12～48 hours.
(5) will leave standstill back solution and filter, filtrate to there not being the alcohol flavor, obtains cornus cyclic olefine ether terpinyl side like extractive with the Rotary Evaporators decompression recycling ethanol;
Described cornus cyclic olefine ether terpinyl side like extractive is six kinds of skunk bush iridoid glycoside compounds, and its molecular weight and molecular structural formula are as follows:
Morroniside (Morroniside) loganin (Loganin)
MW＝406 MW＝390
The new glycosides II of Herba Swertiae bimaculatae glycosides (Sweroside) skunk bush (Comuside II)
MW＝358 MW＝778
The new glycosides I of 7-O-ethylmorroniside skunk bush
(7-0-ethylmorroniside) (Cornuside?I)
MW＝434 MW＝542
In above-mentioned preparation method, can adopt decocting method, pickling process, percolation and ultrasonic method to extract with extraction using alcohol.Also can be with the extract that other organic solvent extraction obtained.
The said skunk bush of the present invention is the mature sarcocarp of Macrocarpium plant skunk bush Cornus officinalis Sieb.etZucc., comprises the product of giving birth to and processed product.
2, detection method comprises following two aspects cornus cyclic olefine ether terpinyl side like extractive of the present invention the time:
(1) liquid phase separation:
Moving phase: be made up of A and B, wherein A is: acetonitrile or methyl alcohol B refer to ultrapure water, flow velocity: 0.5～1.2ml/min.
Chromatographic column: adopt silica gel bonded phase filling liquid-phase chromatographic column to be: C18 post, C8 post.Column temperature: 20～35 ℃.
Detect wavelength: 240nm.
Elution process: adopt gradient elution method.The composition of moving phase is counted A:60%～10%, B:40%～90% with volume percent; Gradient designs and adjusts according to different bonded chromatographic posts, for C18 bonded chromatographic post, when A be acetonitrile, when B is water, elution process is as follows: gradient (calculating with volume percent): 0～2.0min, A:10%, B:90%;
2.0～10.0min，A：10～15％、B：90～85％；
10.0～40.0min，A：15～30％、B：85～70％；
40.0～45.0min，A：30～40％、B：70～60％.
(2) mass spectrometric detection:
The mass spectrum condition is: adopt electric spray ion source, negative ion mode, ion injection electric 4～5KV; 180～300 ℃ of capillary temperatures; Capillary voltage-25V; Sheath gas (N
2) 35 units of flow velocity; Sweep limit m/z 50～1000. confirms each iridoid glycoside compounds by molecular weight and mass spectrum behavior.
3, methodological study of the inventive method and density calculating method:
Carry out the methodological study of the inventive method with the standard substance loganin, the detection that obtains the inventive method is limited to 0.5～10ng/ml (signal to noise ratio 〉=3); Linearity range is 10～2000ng/ml; Relation conefficient is more than 0.9990; In a few days reach day to day precision, circulation ratio relative standard deviation RSD≤5%; Average recovery is 90～110%.
Calculate the content of loganin in the sample by external standard method, calculate the content of other five kinds of iridoid glycoside compounds in the sample again by marker method with peak area or peak height method.
Beneficial effect of the present invention is as follows:
1), preparation method of the present invention can simply directly obtain skunk bush iridoid glycoside compounds extract, need not further processing.
2), the present invention is strong to detection sensitivity height, the specificity of Fructus Corni extract, and is easy and simple to handle reliable, the whole bag of tricks is learned the needs that index all can satisfy iridoid glycosides material in the detection skunk bush reliably.
Embodiment
Extract embodiment 1
Skunk bush is given birth to product medicinal material 50g 80% alcohol reflux, extracts 2 times, and alcohol adding amount is 20 times of medicinal material weight, 2 hours extraction times.United extraction liquid filters and is evaporated to 1/10 volume, adds 95% ethanol in concentrated solution, makes that to contain alcohol amount be 80%, and alcohol is analysed post precipitation refrigeration and left standstill 24 hours, filters, and decompression recycling ethanol obtains skunk bush and gives birth to product refluxing extraction thing.
Extract embodiment 2
Skunk bush processed product medicinal material 50g 80% alcohol reflux extracts 2 times, and alcohol adding amount is 20 times of medicinal material weight, 2 hours extraction times.United extraction liquid filters and concentrating under reduced pressure, concentrated solution is added 4 times of water gaging post precipitation refrigerations left standstill 24 hours, filters, and decompression recycling ethanol obtains skunk bush processed product refluxing extraction thing.
Extract embodiment 3
Skunk bush processed product medicinal material 50g is with 80% ethanol ultrasonic extraction 2 times, each 20min, and alcohol adding amount is 20 times of medicinal material weight.United extraction liquid, filtering and being evaporated to does not have the alcohol flavor, adds 95% ethanol in concentrated solution, makes that to contain the alcohol amount be 80%, and alcohol is analysed post precipitation refrigeration and was left standstill 24 hours, filters, and decompression recycling ethanol obtains skunk bush processed product sonicated extract.
Extract embodiment 4
Skunk bush processed product medicinal material 100g pulverizes the back and crosses 40 mesh sieves, and with the diacolation extraction after 36 hours of 40% alcohol dipping, flow velocity 4～5 ml/min, percolation ration is 10 times of medicinal material weight.United extraction liquid filters and concentrating under reduced pressure, concentrated solution is added 4 times of water gaging post precipitation refrigerations left standstill 12 hours, filters, and decompression recycling ethanol obtains skunk bush processed product percolation extract.
Extract embodiment 5
Skunk bush processed product medicinal material 50g decocts 2 times with 70% ethanol, and alcohol adding amount is 10 times of medicinal material weight, decocts little back of boiling and extracts each 1h.Merge decoction liquor, filter, decompression recycling ethanol gets the skunk bush processed product and decocts extract.
Detect embodiment 1
1 material
1.1 instrument
Liquid chromatograph-mass spectrometer: Waters 2690series LC/LCQ trap:ESI source.
Chromatographic column: SHISEIDO CAPCELL PAK C18 post (MG 5 μ m, 250mm * 4.6mm (i.d.)).
1.2 medicine and reagent
The loganin standard substance are purchased in Nat'l Pharmaceutical ﹠ Biological Products Control Institute.
Methyl alcohol, acetonitrile are chromatographically pure, available from Fisher company; Water is ultrapure water (18.2M Ω cm) 0.45 μ m filter membrane (U.S. Agilent company).
2 instrument conditions
2.1 liquid phase chromatogram condition
Moving phase: A: acetonitrile; B: ultrapure water; Flow velocity: 0.6ml/min.
Sample size 10 μ l.
Column temperature: 35 ℃.
Detect wavelength: 240nm.
Gradient elution (calculating) with volume percent:
0～2.0min，A：10％、B：90％；
2.0～10.0min，A：10～15％、B：90～85％；
10.0～40.0min，A：15～30％、B：85～70％；
40.0～45.0min，A：30～40％、B：70～60％.
2.2 mass spectrum condition
Adopt electric spray ion source, negative ion mode.Injection electric 4.5kV; Capillary voltage-25V; 200 ℃ of capillary temperatures; Sheath gas (N
2) 35 units of flow velocity; Sweep limit m/z 50～1000.
2.3 methodological study
Measure precision, stability and circulation ratio respectively, require relative standard deviation RSD≤5%, detectability requires signal to noise ratio (S/N) 〉=3, and the detection that obtains the inventive method is limited to 0.5～10ng/ml; Linearity range is 10～2000ng/ml; Relation conefficient is more than 0.9990; In a few days reach day to day precision, circulation ratio relative standard deviation RSD≤5%; Average recovery is 90～110%.
2.4 detected result
Through confirming that the retention time of six kinds of iridoid glycoside compounds is respectively in the skunk bush: morroniside (m/z 405) 12.35min; Loganin (m/z 389) 17.06min; Herba Swertiae bimaculatae glycosides (m/z 357) 17.89min; The new glycosides II of skunk bush (m/z 777) 28.02min; 7-oxyethyl group morroniside (m/z 433) 31.25min; The new glycosides I of skunk bush (m/z 541) 32.7min.
Claims (2)
1, extracting method a kind of cornus cyclic olefine ether terpinyl side like extractive the time is characterized in that step and condition are as follows:
(1) the skunk bush medicinal material is made only, promptly removed impurity and residual fruit stone, carpopodium, obtain clean skunk bush;
(2) clean skunk bush being added concentration of volume percent is 20%～90% ethanol, after 8～30 times of amounts are soaked, and refluxing extraction 2～4 times, with little degree of being that boils, each return time is 0.5～1 hour, filters;
(3) merging filtrate is evaporated to nothing alcohol flavor with Rotary Evaporators, gets concentrated solution;
(4) concentrated solution is added ethanol and transfer to and make that to contain the amount of alcohol concentration expressed in percentage by volume be 50%～90, refrigeration was left standstill 12～48 hours;
(5) will leave standstill back solution and filter, filtrate to there not being the alcohol flavor, obtains cornus cyclic olefine ether terpinyl side like extractive with the Rotary Evaporators decompression recycling ethanol;
Described cornus cyclic olefine ether terpinyl side like extractive is six kinds of skunk bush iridoid glycoside compounds, and its molecular weight and molecular structural formula are as follows:
Morroniside (Morroniside) loganin (Loganin)
MW＝406 MW＝390
The new glycosides II of Herba Swertiae bimaculatae glycosides (Sweroside) skunk bush (Cornuside II)
MW＝358 MW＝778
The new glycosides I of 7-O-ethylmorroniside skunk bush
(7-O-ethylmorroniside) (Cornuside?I)
MW＝434 MW＝542。
2, the detection method of six kinds of skunk bush iridoid glycoside compounds that extracting method is extracted a kind of cornus cyclic olefine ether terpinyl side like extractive as claimed in claim 1 the time is characterized in that step and condition are as follows:
(1) liquid phase separation:
Moving phase: be made up of A and B, wherein A is: acetonitrile or methyl alcohol B refer to ultrapure water, flow velocity: 0.5～1.2ml/min;
Chromatographic column: adopt silica gel bonded phase filling liquid-phase chromatographic column to be: C18 post, C8 post; Column temperature: 20～35 ℃:
Detect wavelength: 240nm;
Elution process: adopt gradient elution method, the composition of moving phase is counted A:60%～10%, B:40%～90% with volume percent; Gradient designs and adjusts according to different bonded chromatographic posts, for C18 bonded chromatographic post, when A be acetonitrile, when B is water, elution process is as follows:
Gradient (calculating): 0～2.0min, A:10%, B:90% with volume percent;
2.0～10.0min，A：10～15％、B：90～85％；
10.0～40.0min，A：15～30％、B：85～70％；
40.0～45.0min，A：30～40％、B：70～60％.
(2) mass spectrometric detection:
The mass spectrum condition is: adopt electric spray ion source, negative ion mode, ion injection electric 4～5KV; 180～300 ℃ of capillary temperatures; Capillary voltage-25V; Sheath gas (N
2) 35 units of flow velocity; Sweep limit m/z 50～1000. confirms each iridoid glycoside compounds by molecular weight and mass spectrum behavior.
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| CN101696382B (en) * | 2009-10-22 | 2012-10-17 | 安徽省科学技术研究院 | Method for preparing fructus corni wine |
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| CN104784195A (en) * | 2015-03-24 | 2015-07-22 | 陕西师范大学 | Antidiabetic application of dogwood iridoid glycoside |
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| WO2018029667A1 (en) * | 2016-08-08 | 2018-02-15 | Yeda Research And Development Co. Ltd | Biocontrol enhancers |
| CN106680399B (en) * | 2017-01-20 | 2019-01-22 | 天津市第一中心医院 | Method that is a kind of while measuring the new glycosides of morroniside, loganin, Fructus Corni, oleanolic acid and ursolic acid content |
| CN106680399A (en) * | 2017-01-20 | 2017-05-17 | 天津市第中心医院 | Method for simultaneously determining content of morroniside, loganin, cor-nuside, oleanolic acid and ursolic acid |
| CN111175416A (en) * | 2020-01-17 | 2020-05-19 | 陕西师范大学 | Method for simultaneously detecting 7 components in dogwood |
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| CN113480585A (en) * | 2021-08-10 | 2021-10-08 | 北京中医药大学 | Preparation method of cornuside raw material medicine |
| CN113480585B (en) * | 2021-08-10 | 2023-10-10 | 北京中医药大学 | Preparation method of cornus officinalis new glycoside bulk drug |
| CN114989234A (en) * | 2022-07-15 | 2022-09-02 | 河南中医药大学 | Preparation method and application of iridoid glycoside compound C in dogwood |
| CN115197288A (en) * | 2022-07-15 | 2022-10-18 | 河南中医药大学 | Preparation method and application of iridoid glycoside compound A in dogwood |
| CN115197288B (en) * | 2022-07-15 | 2023-12-19 | 河南中医药大学 | Preparation method and application of iridoid glycoside compound A in dogwood |
| CN114989234B (en) * | 2022-07-15 | 2024-02-02 | 河南中医药大学 | Preparation method and application of iridoid glycoside compound C in dogwood |
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Assignee: Anhui yiyuan Biological Engineering Co., Ltd. Assignor: Changchun Institue of Applied Chemistry, Chinese Academy of Sciences Contract record no.: 2010340000149 Denomination of invention: Process of simultaneously extracting and detecting cornus cyclic olefine ether terpinyl side like extractive Granted publication date: 20090610 License type: Exclusive License Open date: 20070718 Record date: 20100811 |
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