CN106496034A - A kind of while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L. - Google Patents
A kind of while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L. Download PDFInfo
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- CN106496034A CN106496034A CN201610914573.4A CN201610914573A CN106496034A CN 106496034 A CN106496034 A CN 106496034A CN 201610914573 A CN201610914573 A CN 201610914573A CN 106496034 A CN106496034 A CN 106496034A
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- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
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Abstract
The invention discloses a kind of while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L..The Nicotiana tabacum L. powder sample 200g of 60 mesh sieves was weighed, with solid-liquid ratio 1:20 are dissolved in the water, temperature 50 C, and 120min is extracted in stirring.Filtrate is collected with petroleum ether extraction except oil-soluble impuritieses, chlorogenic acid, rutin extracting solution is obtained final product.Extracting solution upper prop carries out the column chromatography for separation of chlorogenic acid and rutin, first with the water elution of 5 times of extracting liquid volumes, until sugar-free is detected in eluent.After washing with water, ethanol gradient elution of the eluent for variable concentrations is changed.The ethanol elution of the ethanol elution and 30 40% concentration of collecting 10 15% concentration respectively obtains solution of chlorogenic acid and rutin solution.Raw material and reagent is this method saved, development cost is reduced, good separating effect is reached.
Description
Technical field
The invention belongs to effective ingredients in plant extractive technique field, is related to a kind of while extracting and separate tobacco from Nicotiana tabacum L.
Chlorogenic acid, the method for rutin.
Background technology
China's tobacco planting area and yield occupy first place in the world, and annual production Nicotiana tabacum L. is more than 200 ten thousand tons.According to statistics,
To more than 7,000 hundred million yuan of the national turnover of profit and tax, therefore, tobacco leaf production and Cigarette processing occupy ten in Chinese national economy within 2013
Divide consequence.But, taken place frequently " Nicotiana tabacum L. in recent years that advocate with World Health Organization (WHO) by Global climate change, natural disaster
There is Nicotiana tabacum L. and harvest and store excess in the impact of control framework pact ", tobacco enterprise, and the discarded tobacco leaf that there are about 30% is not used to Medicated cigarette life
Produce.According to statistics, current Nicotiana tabacum L. inventory level has reached 37.2 months, and occupied fund reaches 350,000,000,000 or so, and many Nicotiana tabacum Lves are big
The big optimal period for exceeding natural alcoholization.However, it is adaptable to which still supply falls short of demand for the high-quality characteristic tobacco of high-grade cigarette brand,
For maintaining the interests of cigarette district leaf tobacco production and protection tobacco grower, annual enterprise maintain certain Nicotiana tabacum L. amount of purchase.Therefore, such as
What neutralizing leaf tobacco production, the contradiction between stock and inapplicable Nicotiana tabacum L. have become tobacco enterprise problem demanding prompt solution.
Nicotiana tabacum L. belongs to state monopoly commodity, this mean that tobacco enterprise must find one kind discarded tobacco leaf is transformed into non-
The approach of tobacco product, can just deal carefully with these inapplicable Nicotiana tabacum Lves.Nicotiana tabacum L. imbalance between supply and demand can be coordinated in order to explore, can be reduced again
Tobacco enterprise stores up cost, increases the effective way of discarded tobacco leaf added value.This project is intended according to result of study for many years, using existing
For biochemistry separating and purifying technology, to content in discarded tobacco leaf more than milligram, it has proved that with treatment disease effects
Secondary metabolite chlorogenic acid and rutin are isolated and purified and chemical modification, develop the higher health product of added value and shield
Skin product.The series of products researched and developed by project not only can be widely applied to medicine, health product and cosmetics and skincare product field, lift low order
The added value of Nicotiana tabacum L., and considerable economic benefit and social benefit will be created for tobacco enterprise.
Chlorogenic acid is widely distributed phenylpropanoids, and scientific name is caffeoyl guinic acid, sees formula 1, because caffeic acid can
With 3,4,5 hydroxyls of quinic acid into ester bond so there are the different isomers such as mono-/bis -/tri- caffeoyl guinic acid, green original is all referred to as
Acid.Leading composition is accounted for 3 caffeoyl guinic acids in Nicotiana tabacum L..3 caffeoyl guinic acids (hereinafter referred to as chlorogenic acid) have a lot
Physiological function.Suppress inflammation, hypoglycemic the liver protecting function etc. including antibacterial.
Rutin is flavonoid compound, falls within Polyphenols also known as rutin, sees formula 2, and in Nicotiana tabacum L., content also reaches
Content to 10mg/g or so.It is a kind of biological activity very strong, extensive Chinese medicine of clinical practice.There are anti-oxidizing activities, resist
The pharmacological actions such as lipid peroxidation, antiviral, anti-acute pancreatitis, can be used for the treatment of multiple chronic diseases.
Existing goods chlorogenic acid is all extracted from Flos Lonicerae and the Cortex Eucommiae；Rutin is extracted from Flos Sophorae.Also have from some other plant
The report of barosmin is extracted in thing.The technique that takes typically changes the parameters such as temperature, solvent, solid-liquid ratio and improves extraction ratio.Pass through
CO2Extraction, the technique such as macroporous resin excessively carry chlorogenic acid and rutin respectively.Due to complicated component in Nicotiana tabacum L., containing substantial amounts of sugar, fat
With other organic substances, in extraction process, substantial amounts of reducing sugar produces Maillard reaction with amino-compound, defines dark brown
Pigment, have a strong impact on chlorogenic acid and Extraction of rutin effect.So extract separating chlorogenic acid and Folium Symplocoris Caudatae from discarded tobacco leaf simultaneously
Glycosides will complexity from chlorogenic acid extracting in Flos Lonicerae (rich in chlorogenic acid) and Flos Sophorae (rich in rutin) and rutin more than list.Patent
104086425A is reported from Nicotiana tabacum L. while extract the report of separating chlorogenic acid, rutin, Salanesol and nicotine, we according to
The patent embodiment repeats, and unrealized chlorogenic acid and rutin are efficiently separated, and pigment, in dark brown, separating effect does not reach
To the effect described in this patent.So far, we yet there are no and concurrently separate chlorogenic acid and rutin on the basis of desaccharide and pigment
Technique is reported.
Content of the invention
The present invention is carried to concurrently separating two kinds of compounds of chlorogenic acid and rutin from discarded tobacco leaf for present Research
Taking technique is studied, in order to provide a kind of effective ways that can concurrently separate chlorogenic acid and rutin.The method
Raw material and reagent is saved, development cost is reduced, good separating effect is reached.
A kind of while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L.：Comprise the following steps：
1) tobacco material is once extracted with water as solvent after crushing, and obtains Tobacco Chlorogenic Acid, the crude extract of rutin；
2) crude extract is extracted with organic solvent, obtain the extracting solution of degreasing；
3) extracting solution upper prop carries out the column chromatography for separation of chlorogenic acid and rutin.
Step 1) in by tobacco material crushing 60 mesh sieve.
Step 1) middle 50-60 DEG C of Extracting temperature of setting, feed liquid mass volume ratio 1:Under the conditions of 20-25 (W/V, g/mL), use
Water extraction 90-150min；50 DEG C of preferable temperature, feed liquid mass volume ratio 1:20 (W/V, g/mL), use water extraction 120min.
Step 2) according to crude extract and petroleum ether volume ratio 1:1-1.2 is extracted, preferred volume ratio 1:1, obtain degreasing
Extracting solution.
Step 3) middle selection AB-8 or HPD-100 model resins.
Step 3) first with the water elution of 5 times of extracting liquid volumes, until sugar-free is detected in eluent.
Step 3) wash with water after, change eluent for variable concentrations ethanol gradient elution.
Step 3) respectively collect 10-15% concentration ethanol elution and 30-40% concentration ethanol elution obtain green
Raw aqueous acid and rutin solution.Specifically with the elution speed of 2 times of resin volumes of eluting per hour, using 10%, 13%,
The ethanol gradient elution of 15% concentration is collected and obtains solution of chlorogenic acid；Ethanol ladder using 30%, 33%, 36%, 40% concentration
Degree eluting collects rutin solution.The solution of chlorogenic acid and rutin solution that eluting is collected carries out lyophilization after concentrating respectively,
Crude powder is obtained, dissolved powders are crystallized.
The advantage of the present invention：
1st, the present invention is directly disposably extracted using water, greatly reduces extraction cost, the Tobacco Chlorogenic Acid that obtains,
The crude extract of rutin, Tobacco Chlorogenic Acid, the extraction ratio of rutin respectively reach 84%, and 99% (tests number according to the response rate
According to).The content of chlorogenic acid and rutin in extracting solution respectively reaches 21.7mg/g, 16.5mg/g.
2nd, after present invention extraction, extracting solution does not heat concentration, directly crosses macroporous resin, washes water-soluble sugar with water, it is to avoid
The Maillard reaction that soluble sugar is participated in, reduces chromogenesis.
3rd, macroporous resin adjustment water and alcohol eluting ratio in the present invention, effectively remove depigmentation on macroporous resin.
4th, the 10-15% ethanol elution Content of Chlorogenic Acid that the present invention is collected is 20.2mg/g, and extraction ratio is 93.1%
(in the chlorogenic acid separating liquid for obtaining, rutin content be 3mg/g, HPLC methods),；In 30-40% ethanol elution, rutin contains
Measure as 11.5mg/g, extraction ratio 75.2%, (in the rutin extracting solution for obtaining, chlorogenic acid content is 0.8mg/g, HPLC methods).
By three above step, chlorogenic acid and rutin are almost kept completely separate, and final extraction ratio can be 81.9% He respectively
61%.
We (add 1% chitosan solution, remove impurity and sink according to existing patent (104086425A) processing step 2
Form sediment, adjust pH to 2, overnight, obtain rutin precipitation, with hot water dissolving after Refrigerator store, crystallization；Survey in remaining extracting solution
Chlorogenic acid 16.4mg/g, rutin 11.2mg/g) chlorogenic acid and rutin are separated, the result for actually obtaining is green original
Sour extraction ratio is 60%, the extraction ratio 56.2% of rutin, and according to (104086425A) process, chlorogenic acid is not had with rutin
Separated.
In a word, the present invention achieves discarded tobacco leaf Content of Chlorogenic Acid and Folium Symplocoris Caudatae by the cheap solvent of simple technique and safety
Be completely separated while glycosides functional component, operate extremely simple, save energy, Environmental Safety, be realize industrial effectively
Technique.
Description of the drawings
Fig. 1 is present invention process flow chart.
Specific embodiment
The present invention, rather than limitation of the present invention are intended to further illustrate with reference to embodiments.
Embodiment 1：
First, extract while Tobacco Chlorogenic Acid, rutin
The Nicotiana tabacum L. powder sample 200g of 60 mesh sieves was weighed, with solid-liquid ratio 1:20 are dissolved in 4000ml water, pour stirring into
Extractor simultaneously sets 50 DEG C of Extracting temperature, and stirring extraction time 120min is extracted.The extracting solution for obtaining is carried out sucking filtration,
Residue is filtered off, filtrate is collected.In filtrate, Tobacco Chlorogenic Acid, the extraction ratio of rutin respectively reach 84%, and 99% (according to the response rate
Experimental data).The content of chlorogenic acid and rutin in filtrate respectively reaches 21.7mg/g, 16.5mg/g.Filtrate is pressed 1:1 body
The consumption petroleum ether extraction remove impurity of product ratio, reclaims upper organic phase, merges lower floor's water phase, obtains final product chlorogenic acid, rutin and carry
Take liquid.Now measure green former rue, fragrant glycosides content and be respectively 20.9mg/g, 15.3mg/g.
2nd, the separation of Tobacco Chlorogenic Acid, rutin
1. separating chlorogenic acid
8 model macroporous resins of AB through pretreatment are loaded chromatographic column, makes cylinder smooth, without inclination, depletion of QI in post bed
Bubble, not stratified.It is 3 that extracting solution pH is adjusted with hydrochloric acid solution, weighs and the extracting solution of macroporous resin same volume is poured slowly into chromatography
In post, flow out extracting solution with the elution speed of 2BV/h (2 times of resin volumes of eluting per hour), finish rear closure piston, stand
30min makes material fully adsorb.The distilled water of 5 times of resin volumes is weighed, with the sugar that the flow velocity eluting of 2BV/h adsorbs in filler
Point.10%, 13%, 15% ethanol solution is prepared, is poured into successively, consumption ibid, merges eluent
Solution of chlorogenic acid can be obtained.10-15% ethanol elution Content of Chlorogenic Acid is 20.2mg/g, and extraction ratio is 93.1%, wherein, rue
Fragrant glycosides content be 3mg/g, HPLC methods.By solution of chlorogenic acid concentrating under reduced pressure, vacuum drying treatment is carried out, chlorogenic acid crude product can be obtained.
Crude product obtains chlorogenic acid pure product after the methods such as extraction, crystallization are processed.
2. rutin is separated
30%, 33%, 36%, 40% ethanol solution is prepared, being poured in same chromatographic column successively carries out eluting, consumption
Ibid, merge eluent and can obtain rutin solution.In 30-40% ethanol elution rutin content be 11.5mg/g, extraction ratio
75.2%, wherein, chlorogenic acid content is 0.8mg/g, HPLC methods.Rutin solution decompression is concentrated, vacuum drying treatment is carried out,
Rutin crude product can be obtained.Crude product obtains rutin sterling after the methods such as extraction, crystallization are processed.
Chlorogenic acid and rutin are almost kept completely separate, and final extraction ratio can be 81.9% and 61% respectively.
Embodiment 2：
First, extract while Tobacco Chlorogenic Acid, rutin
The Nicotiana tabacum L. powder sample 200g of 60 mesh sieves was weighed, with solid-liquid ratio 1:25 are dissolved in 5000ml water, pour stirring into
Extractor simultaneously sets 50 DEG C of Extracting temperature, and stirring extraction time 120min is extracted.The extracting solution for obtaining is carried out sucking filtration,
Residue is filtered off, filtrate is collected.Filtrate is pressed volume 1:The petroleum ether extraction remove impurity of the consumption of 1 ratio, reclaims upper organic phase, closes
And lower floor's water phase, obtain final product chlorogenic acid, rutin extracting solution.
2nd, the separation of Tobacco Chlorogenic Acid, rutin
1. separating chlorogenic acid
100 model macroporous resins of HPD through pretreatment are loaded chromatographic column, makes cylinder smooth, without inclination, in post bed
Bubble-free, not stratified.It is 3 that extracting solution pH is adjusted with hydrochloric acid solution, and weighing is poured slowly into the extracting solution of macroporous resin same volume
In chromatographic column, flow out extracting solution with the elution speed of 2BV/h (2 times of resin volumes of eluting per hour), finish rear closure piston,
Standing 30min makes material fully adsorb.The distilled water of 5 times of resin volumes is weighed, is adsorbed in filler with the flow velocity eluting of 2BV/h
Sugar.10%, 13%, 15% ethanol solution is prepared, is poured into successively, consumption ibid, wash by merging
De- liquid can obtain solution of chlorogenic acid.Through high performance liquid chromatography detection, resulting solution Content of Chlorogenic Acid accounts for extracting solution before separating
More than 84%.By solution of chlorogenic acid concentrating under reduced pressure, vacuum drying treatment is carried out, chlorogenic acid crude product can be obtained.Crude product is through extraction, knot
After the process of the methods such as crystalline substance, chlorogenic acid pure product is obtained.
2. rutin is separated
30%, 33%, 36%, 40% ethanol solution is prepared, being poured in same chromatographic column successively carries out eluting, consumption
Ibid, merge eluent and can obtain rutin solution.Through high performance liquid chromatography detection, before in resulting solution, rutin content accounts for separation
More than the 64% of extracting solution.Rutin solution decompression is concentrated, vacuum drying treatment is carried out, rutin crude product can be obtained.Crude product is passed through
After crossing the process of the methods such as extraction, crystallization, rutin sterling is obtained.
In the range of operating condition of the present invention, the present invention is attained by the promising result better than prior art, on
State embodiment 1 and 2 to have better effect.
Claims (10)
1. a kind of while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：Comprise the following steps：
1) tobacco material is once extracted with water as solvent after crushing, and obtains Tobacco Chlorogenic Acid, the crude extract of rutin；
2) crude extract is extracted with organic solvent, obtain the extracting solution of degreasing；
3) extracting solution upper prop carries out the column chromatography for separation of chlorogenic acid and rutin.
2. according to claim 1 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 1) in by tobacco material crushing 60 mesh sieve.
3. according to claim 1 and 2 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., its feature exists
In：Step 1) middle 50-60 DEG C of Extracting temperature of setting, feed liquid mass volume ratio 1:Under the conditions of 20-25 (W/V, g/mL), water extraction is used
90-150min；50 DEG C of preferable temperature, feed liquid mass volume ratio 1:20 (W/V, g/mL), use water extraction 120min.
4. according to claim 1 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 2) according to crude extract and petroleum ether volume ratio 1:1-1.2 is extracted, preferred volume ratio 1:1, obtain the extracting solution of degreasing.
5. according to claim 1 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 3) middle selection AB-8 or HPD-100 model resins.
6. according to claim 1 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 3) first with the water elution of 5 times of extracting liquid volumes, until sugar-free is detected in eluent.
7. according to claim 6 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 3) wash with water after, change eluent for variable concentrations ethanol gradient elution.
8. according to claim 7 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 3) ethanol elution of collection 10-15% concentration and the ethanol elution of 30-40% concentration obtain solution of chlorogenic acid respectively
With rutin solution.
9. according to claim 8 while the method for extracting separating chlorogenic acid and rutin from Nicotiana tabacum L., it is characterised in that：
Step 3) with the elution speed of 2 times of resin volumes of eluting per hour, using the ethanol gradient elution of 10%, 13%, 15% concentration
Collection obtains solution of chlorogenic acid；Rutin solution is collected using the ethanol gradient elution of 30%, 33%, 36%, 40% concentration.
10. the method for extracting separating chlorogenic acid and rutin while according to claim 8 or claim 9 from Nicotiana tabacum L., its feature
It is：The solution of chlorogenic acid and rutin solution that eluting is collected carries out lyophilization after concentrating respectively, obtains crude powder, dissolves
Powder is crystallized.
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| CN108484695A (en) * | 2018-04-08 | 2018-09-04 | 湖南中医药大学 | A method of extracting benzyl carbinol glycosides and flavone compound simultaneously from butterflybush flower |
| CN108689803A (en) * | 2018-06-28 | 2018-10-23 | 大连理工大学 | A kind of method of waste tobacco leaf comprehensive utilization |
| CN110066264A (en) * | 2018-01-22 | 2019-07-30 | 湖南中烟工业有限责任公司 | A method of extracting rutin sophorin and Scopoletin from tobacco leaf |
| CN114369026A (en) * | 2021-12-06 | 2022-04-19 | 湖南生物机电职业技术学院 | Method for extracting chlorogenic acid and rutin from Ficus pumila leaves |
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| CN110066264A (en) * | 2018-01-22 | 2019-07-30 | 湖南中烟工业有限责任公司 | A method of extracting rutin sophorin and Scopoletin from tobacco leaf |
| CN108484695A (en) * | 2018-04-08 | 2018-09-04 | 湖南中医药大学 | A method of extracting benzyl carbinol glycosides and flavone compound simultaneously from butterflybush flower |
| CN108484695B (en) * | 2018-04-08 | 2021-12-07 | 湖南中医药大学 | Method for simultaneously extracting phenylethanoid glycosides and flavonoids from buddleja officinalis |
| CN108689803A (en) * | 2018-06-28 | 2018-10-23 | 大连理工大学 | A kind of method of waste tobacco leaf comprehensive utilization |
| CN108689803B (en) * | 2018-06-28 | 2021-06-15 | 大连理工大学 | Comprehensive utilization method of waste tobacco leaves |
| CN114369026A (en) * | 2021-12-06 | 2022-04-19 | 湖南生物机电职业技术学院 | Method for extracting chlorogenic acid and rutin from Ficus pumila leaves |
| CN114369026B (en) * | 2021-12-06 | 2023-05-26 | 湖南生物机电职业技术学院 | Method for extracting chlorogenic acid and rutin from ficus pumila leaves |
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| CN106496034B (en) | 2019-07-12 |
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