CN106496034B - Method a kind of while that separating chlorogenic acid and rutin sophorin are extracted from tobacco leaf - Google Patents
Method a kind of while that separating chlorogenic acid and rutin sophorin are extracted from tobacco leaf Download PDFInfo
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- CN106496034B CN106496034B CN201610914573.4A CN201610914573A CN106496034B CN 106496034 B CN106496034 B CN 106496034B CN 201610914573 A CN201610914573 A CN 201610914573A CN 106496034 B CN106496034 B CN 106496034B
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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
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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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- 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
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Abstract
The invention discloses a kind of methods for extracting separating chlorogenic acid and rutin sophorin from tobacco leaf simultaneously.The tobacco leaf powder sample 200g for weighing 60 meshes, is dissolved in the water with solid-liquid ratio 1:20, temperature 50 C, and 120min is extracted in stirring.It collects filtrate and removes oil-soluble impurities with petroleum ether extraction to get chlorogenic acid, rutin sophorin extracting solution.Extracting solution upper prop carries out the column chromatography for separation of chlorogenic acid and rutin sophorin, first uses the water elution of 5 times of extracting liquid volumes, up to sugar-free detects in eluent.After being eluted with water, the ethanol gradient elution that eluent is various concentration is changed.The ethanol eluate of 10-15% concentration is collected respectively and the ethanol eluate of 30-40% concentration obtains solution of chlorogenic acid and rutin sophorin solution.This method save raw materials and reagents, reduce development cost, reach good separating effect.
Description
Technical field
The invention belongs to effective ingredients in plant extractive technique fields, are related to a kind of extraction and separate tobacco from tobacco leaf simultaneously
The method of chlorogenic acid, rutin sophorin.
Background technique
China's tobacco planting area and yield occupy first place in the world, and the annual tobacco leaf that produces 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 it is taken place frequently " the tobacco advocated with the World Health Organization by Global climate change, natural calamity in recent years
There is tobacco leaf and harvest and store excess in the influence of control framework pact ", tobacco enterprise, and there are about 30% discarded tobacco leaf, to be not used to cigarette raw
It produces.According to statistics, current tobacco leaf inventory level has reached 37.2 months, and occupied fund reaches 350,000,000,000 or so, and many tobacco leaves are big
Big is more than the optimal period of natural alcoholization.Nevertheless, be suitable for high-grade cigarette brand high-quality characteristic tobacco still supply falls short of demand,
To maintain cigarette district leaf tobacco production and protecting the interests of tobacco grower, annual enterprise must also maintain certain tobacco leaf amount of purchase.Therefore, such as
Contradiction between what neutralizing leaf tobacco production, inventory and not applicable tobacco leaf has become tobacco enterprise urgent problem to be solved.
Tobacco belongs to state monopoly commodity, this mean that tobacco enterprise must find it is a kind of discarded tobacco leaf is transformed into it is non-
The approach of tobacco product can just deal carefully with these not applicable tobacco leaves.It can coordinate tobacco leaf imbalance between supply and demand in order to explore and reduce
Tobacco enterprise stores up cost, increases the effective way of discarded tobacco leaf added value.This project is quasi- according to many years result of study, using existing
For biochemistry separating and purifying technology, to content in discarded tobacco leaf more than milligram, it has proved that there are treatment disease effects
Secondary metabolite chlorogenic acid and rutin sophorin are isolated and purified and chemical modification, develops the higher health care product of added value and shield
Skin product.The series of products that project is researched and developed not only can be widely applied to medicine, health care product and cosmetics and skincare product field, promote low order
The added value of tobacco leaf, 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, formula 1 is seen, because caffeic acid can
Green original is all referred to as so there are the different isomers such as mono-/bis -/tri- caffeoyl guinic acids at ester bond with 3,4,5 hydroxyls of chinic acid
Acid.Leading composition is accounted for 3-caffeoylquinic acid in tobacco leaf.3-caffeoylquinic acid (hereinafter referred to as chlorogenic acid) has very much
Physiological function.Inhibit inflammation, hypoglycemic protection liver function etc. including antibacterial.
Rutin sophorin is also known as rutin, is flavonoid compound, also belongs to Polyphenols, sees formula 2, content also reaches in tobacco
To the content of 10mg/g or so.It is that a kind of bioactivity is very strong, the extensive Chinese medicine of clinical application.With anti-oxidizing activities, resist
The pharmacological actions such as lipid peroxidation, antiviral, anti-acute pancreatitis, can be used for the treatment of a variety of chronic diseases.
Existing goods chlorogenic acid is all extracted from honeysuckle and Cortex Eucommiae;Rutin sophorin is extracted from sophora flower.Also have from some other plant
The report of barosmin is extracted in object.The technique taken generally changes the parameters such as temperature, solvent, solid-liquid ratio and improves recovery rate.Pass through
CO2Extraction, the techniques such as macroreticular resin excessively mention chlorogenic acid and rutin respectively.Due to complicated component in tobacco leaf, contain a large amount of sugar, rouge
With other organic substances, a large amount of reduced sugar and amino-compound generate Maillard reaction in extraction process, form dark brown
Pigment, seriously affect chlorogenic acid and Extraction of rutin effect.So extracting separating chlorogenic acid and rue simultaneously from discarded tobacco leaf
More than list, chlorogenic acid extracting and rutin sophorin from honeysuckle (being rich in chlorogenic acid) and sophora flower (being rich in rutin sophorin) want complicated to glycosides.Patent
104086425A reports from tobacco leaf while extracting the report of separating chlorogenic acid, rutin sophorin, Salanesol and nicotine, we according to
The patent embodiment repeats, and efficiently separating for chlorogenic acid and rutin sophorin is not implemented, and pigment is in dark brown, and separating effect does not reach
To effect described in this patent.So far, we yet there are no in desaccharification and separating chlorogenic acid and rutin sophorin simultaneously on the basis of pigment
Technique report.
Summary of the invention
The present invention is directed to present Research, to two kinds of compounds of separating chlorogenic acid and rutin sophorin mention simultaneously from discarded tobacco leaf
Taking technique is studied, in order to provide it is a kind of can simultaneously separating chlorogenic acid and rutin sophorin effective ways.This method
Raw materials and reagents are saved, development cost is reduced, reach good separating effect.
Method a kind of while that separating chlorogenic acid and rutin sophorin are extracted from tobacco leaf: the following steps are included:
1) tobacco material takes water as a solvent primary extraction after crushing, and obtains the crude extract of Tobacco Chlorogenic Acid, rutin sophorin;
2) crude extract is extracted with organic solvent, obtains the extracting solution of degreasing;
3) extracting solution upper prop carries out the column chromatography for separation of chlorogenic acid and rutin sophorin.
Tobacco material is crushed into the sieving of 60 mesh in step 1).
50-60 DEG C of Extracting temperature of setting in step 1) under the conditions of feed liquid mass volume ratio 1:20-25 (W/V, g/mL), is used
Water extracts 90-150min;50 DEG C of preferable temperature, 120min is extracted with water in feed liquid mass volume ratio 1:20 (W/V, g/mL).
It is extracted in step 2) according to crude extract and petroleum ether volume ratio 1:1-1.2, preferred volume ratio 1:1 obtains degreasing
Extracting solution.
AB-8 HPD-100 model resin is selected in step 3).
Step 3) is first with the water elution of 5 times of extracting liquid volumes, until sugar-free detects in eluent.
After step 3) is eluted with water, the ethanol gradient elution that eluent is various concentration is changed.
Step 3) collects the ethanol eluate of 10-15% concentration respectively and the ethanol eluate of 30-40% concentration obtain it is green
Raw aqueous acid and rutin sophorin solution.Specifically to elute the elution speed of 2 times of resin volumes per hour, using 10%, 13%,
The ethanol gradient elution of 15% concentration is collected to obtain solution of chlorogenic acid;Using the ethyl alcohol ladder of 30%, 33%, 36%, 40% concentration
Rutin sophorin solution is collected in degree elution.The solution of chlorogenic acid and rutin sophorin solution for eluting collection are freeze-dried after being concentrated respectively,
Crude powder is obtained, dissolved powders are crystallized.
Advantage of the invention:
1, the present invention directlys adopt water and is disposably extracted, and greatly reduces extraction cost, obtained Tobacco Chlorogenic Acid,
The crude extract of rutin sophorin, Tobacco Chlorogenic Acid, rutin sophorin recovery rate respectively reach 84%, 99% (tests number according to the rate of recovery
According to).The content of chlorogenic acid and rutin sophorin in extracting solution respectively reaches 21.7mg/g, 16.5mg/g.
2, thermal concentration is not added in extracting solution after present invention extraction, directly crosses macroreticular resin, water-soluble sugar is eluted with water, avoids
The Maillard reaction that soluble sugar is participated in reduces pigment and is formed.
3, macroreticular resin adjustment water and alcohol elute ratio in the present invention, and pigment is effectively removed on macroreticular resin.
4, the 10-15% ethanol eluate Content of Chlorogenic Acid that the present invention collects is 20.2mg/g, recovery rate 93.1%
(in obtained chlorogenic acid separating liquid, rutin sophorin content is 3mg/g, HPLC method),;Rutin sophorin contains in 30-40% ethanol eluate
Amount is 11.5mg/g, recovery rate 75.2%, (in obtained rutin sophorin extracting solution, chlorogenic acid content 0.8mg/g, HPLC method).
By three above step, chlorogenic acid and rutin sophorin are almost kept completely separate, and final recovery rate can be 81.9% He respectively
61%.
We (are added 1% chitosan solution, it is heavy to remove impurity according to existing patent (104086425A) processing step 2
Form sediment, adjust pH to 2, overnight, obtain rutin sophorin precipitating, with after hot water dissolving in refrigerator save, crystallization;It is surveyed in remaining extracting solution
Chlorogenic acid 16.4mg/g, rutin sophorin 11.2mg/g) chlorogenic acid and rutin sophorin are separated, it is actually obtaining the result is that green original
Sour recovery rate is 60%, and the recovery rate 56.2% of rutin sophorin, according to (104086425A) process, chlorogenic acid does not have with rutin sophorin
It is separated.
In short, the present invention realizes discarded tobacco leaf Content of Chlorogenic Acid and rue by the cheap solvent of simple technique and safety
It is completely separated while glycosides functional component, operates extremely simple, the saving energy, Environmental Safety is that realization is industrial effectively
Technique.
Detailed description of the invention
Fig. 1 is process flow chart of the invention.
Specific embodiment
It is intended to further illustrate the present invention with reference to embodiments, rather than limitation of the present invention.
Embodiment 1:
One, it is extracted while Tobacco Chlorogenic Acid, rutin sophorin
The tobacco leaf powder sample 200g for weighing 60 meshes, is dissolved in 4000ml water with solid-liquid ratio 1:20, pours into stirring
Extractor simultaneously sets 50 DEG C of Extracting temperature, and stirring extraction time 120min is extracted.Obtained extracting solution is filtered,
Residue is filtered off, filtrate is collected.Tobacco Chlorogenic Acid in filtrate, rutin sophorin recovery rate respectively reach 84%, 99% (according to the rate of recovery
Experimental data).The content of chlorogenic acid and rutin sophorin in filtrate respectively reaches 21.7mg/g, 16.5mg/g.Filtrate is pressed into 1:1 body
The dosage of product ratio is cleaned with petroleum ether extraction, recycles upper organic phase, is merged lower layer's water phase and is mentioned to get chlorogenic acid, rutin sophorin
Take liquid.Green former rue is measured at this time, fragrant glycosides content is respectively 20.9mg/g, 15.3mg/g.
Two, the separation of Tobacco Chlorogenic Acid, rutin sophorin
1. separating chlorogenic acid
It will be packed into chromatographic column by pretreated AB-8 model macroreticular resin, keep cylinder smooth, no inclination, without gas in column bed
Bubble, it is not stratified.Adjusting extracting solution pH with hydrochloric acid solution is 3, weighs and is poured slowly into chromatography with the extracting solution of macroreticular resin same volume
In column, flow out extracting solution with the elution speed of 2BV/h (per hour elute 2 times of resin volumes), after closure piston, stand
30min adsorbs material sufficiently.The distilled water of 5 times of resin volumes is weighed, the sugar being adsorbed in filler is eluted with the flow velocity of 2BV/h
Point.The ethanol solution for preparing 10%, 13%, 15%, successively pours into chromatographic column and is eluted, and dosage is same as above, and merges eluent
Solution of chlorogenic acid can be obtained.10-15% ethanol eluate Content of Chlorogenic Acid is 20.2mg/g, recovery rate 93.1%, wherein rue
Fragrant glycosides content is 3mg/g, HPLC method.Solution of chlorogenic acid is concentrated 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 of extracting, crystallizing processing.
2. separating rutin sophorin
The ethanol solution for preparing 30%, 33%, 36%, 40%, successively pours into same root chromatographic column and is eluted, dosage
Ibid, rutin sophorin solution can be obtained by merging eluent.Rutin sophorin content is 11.5mg/g, recovery rate in 30-40% ethanol eluate
75.2%, wherein chlorogenic acid content 0.8mg/g, HPLC method.Rutin sophorin solution is concentrated under reduced pressure, vacuum drying treatment is carried out,
Rutin sophorin crude product can be obtained.Crude product obtains rutin sophorin sterling after the methods of extracting, crystallizing processing.
Chlorogenic acid and rutin sophorin are almost kept completely separate, and final recovery rate can be 81.9% and 61% respectively.
Embodiment 2:
One, it is extracted while Tobacco Chlorogenic Acid, rutin sophorin
The tobacco leaf powder sample 200g for weighing 60 meshes, is dissolved in 5000ml water with solid-liquid ratio 1:25, pours into stirring
Extractor simultaneously sets 50 DEG C of Extracting temperature, and stirring extraction time 120min is extracted.Obtained extracting solution is filtered,
Residue is filtered off, filtrate is collected.Filtrate is cleaned in the dosage of volume 1:1 ratio with petroleum ether extraction, upper organic phase is recycled, is closed
And lower layer's water phase is to get chlorogenic acid, rutin sophorin extracting solution.
Two, the separation of Tobacco Chlorogenic Acid, rutin sophorin
1. separating chlorogenic acid
It will be packed into chromatographic column by pretreated HPD-100 model macroreticular resin, keep cylinder smooth, no inclination, in column bed
Bubble-free, it is not stratified.Adjusting extracting solution pH with hydrochloric acid solution is 3, weighs and is poured slowly into the extracting solution of macroreticular resin same volume
In chromatographic column, flow out extracting solution with the elution speed of 2BV/h (per hour elute 2 times of resin volumes), after closure piston,
Standing 30min adsorbs material sufficiently.The distilled water of 5 times of resin volumes is weighed, is adsorbed in filler with the flow velocity elution of 2BV/h
Sugar.The ethanol solution for preparing 10%, 13%, 15%, successively pours into chromatographic column and is eluted, dosage is same as above, and merging is washed
De- liquid can obtain solution of chlorogenic acid.Through high performance liquid chromatography detection, acquired solution Content of Chlorogenic Acid, which accounts for, separates preceding extracting solution
84% or more.Solution of chlorogenic acid is concentrated under reduced pressure, vacuum drying treatment is carried out, chlorogenic acid crude product can be obtained.Crude product is by extraction, knot
After the processing of the methods of crystalline substance, chlorogenic acid pure product is obtained.
2. separating rutin sophorin
The ethanol solution for preparing 30%, 33%, 36%, 40%, successively pours into same root chromatographic column and is eluted, dosage
Ibid, rutin sophorin solution can be obtained by merging eluent.Through high performance liquid chromatography detection, before rutin sophorin content accounts for separation in acquired solution
64% or more of extracting solution.Rutin sophorin solution is concentrated under reduced pressure, vacuum drying treatment is carried out, rutin sophorin crude product can be obtained.Crude product warp
After crossing the methods of extraction, crystallization processing, rutin sophorin sterling is obtained.
Within the scope of operating condition of the present invention, the present invention is attained by the promising result better than the prior art, on
Examples 1 and 2 are stated to have better effect.
Claims (6)
1. a kind of method for extracting separating chlorogenic acid and rutin sophorin from tobacco leaf simultaneously, it is characterised in that: the following steps are included:
1) tobacco material takes water as a solvent primary extraction after crushing, and obtains the crude extract of Tobacco Chlorogenic Acid, rutin sophorin;
2) crude extract is extracted with organic solvent, obtains the extracting solution of degreasing;
3) extracting solution upper prop carries out the column chromatography for separation of chlorogenic acid and rutin sophorin;
50-60 DEG C of Extracting temperature, under the conditions of feed liquid mass volume ratio 1:20-25 (W/V, g/mL) is set in step 1), is mentioned with water
Take 90-150min;
It is extracted in step 2 according to crude extract and petroleum ether volume ratio 1:1-1.2, obtains the extracting solution of degreasing;
AB-8 HPD-100 model resin is selected in step 3);
Step 3) first uses the water elution of 5 times of extracting liquid volumes, until sugar-free detects in eluent;
After step 3) is eluted with water, the ethanol gradient elution that eluent is various concentration is changed;10-15% concentration is collected respectively
Ethanol eluate and the ethanol eluate of 30-40% concentration obtain solution of chlorogenic acid and rutin sophorin solution.
2. method that is according to claim 1 while extracting separating chlorogenic acid and rutin sophorin from tobacco leaf, it is characterised in that:
Tobacco material is crushed into the sieving of 60 mesh in step 1).
3. method that is according to claim 1 or 2 while extracting separating chlorogenic acid and rutin sophorin from tobacco leaf, feature exist
In: 50 DEG C of Extracting temperature are set in step 1), feed liquid mass volume ratio 1:20(W/V, g/mL), 120min is extracted with water.
4. method that is according to claim 1 while extracting separating chlorogenic acid and rutin sophorin from tobacco leaf, it is characterised in that:
According to crude extract and petroleum ether volume ratio 1:1 in step 2, the extracting solution of degreasing is obtained.
5. method that is according to claim 1 while extracting separating chlorogenic acid and rutin sophorin from tobacco leaf, it is characterised in that:
Step 3) is collected with eluting the elution speeds of 2 times of resin volumes per hour using the ethanol gradient elution of 10%, 13%, 15% concentration
Obtain solution of chlorogenic acid;Rutin sophorin solution is collected using the ethanol gradient elution of 30%, 33%, 36%, 40% concentration.
6. the method for extracting separating chlorogenic acid and rutin sophorin from tobacco leaf simultaneously according to claim 1 or 5, feature exist
It is freeze-dried after: the solution of chlorogenic acid and rutin sophorin solution for eluting collection is concentrated respectively, obtains crude powder, dissolve powder
End is crystallized.
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CN110066264B (en) * | 2018-01-22 | 2022-03-15 | 湖南中烟工业有限责任公司 | Method for extracting rutin and scopoletin from tobacco leaves |
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 |
CN108689803B (en) * | 2018-06-28 | 2021-06-15 | 大连理工大学 | Comprehensive utilization method of waste tobacco 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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