CN107383131A - The extracting method of active ingredient in a kind of citrus shedding and tangerine peel - Google Patents
The extracting method of active ingredient in a kind of citrus shedding and tangerine peel Download PDFInfo
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- CN107383131A CN107383131A CN201710596989.0A CN201710596989A CN107383131A CN 107383131 A CN107383131 A CN 107383131A CN 201710596989 A CN201710596989 A CN 201710596989A CN 107383131 A CN107383131 A CN 107383131A
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
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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
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
- C07J73/008—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by two hetero atoms
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- Medicines Containing Plant Substances (AREA)
Abstract
The extracting method of active ingredient in a kind of citrus shedding and tangerine peel, it includes degreasing, 75% alcohol reflux simultaneously is extracted to obtain extract solution with ultrasonic assistant, it is layered after extract solution is concentrated with chloroform, then respectively obtains the higher aurantiamarin finished product of purity, synephrine finished product and lemon bitter principle finished product with different methods.The present invention is suitable to industrialized production, can improve the comprehensive utilization ratio of citrus shedding and tangerine peel, and then improves its economic use value, promotes the further development of citrus industry.
Description
Technical field
The present invention relates to the extractive technique field of effective components in plants, and in particular to has in a kind of citrus shedding and tangerine peel
Imitate the extracting method of composition.
Background technology
Citrus trees are easily into flower, but percentage of fertile fruit is relatively low, and generally 3 ~ 5%, growth course of the citrus young fruit to ripe citrus
In, due to insect pest, soil fertilizer deficiency water shortage, dispenser are improper, flower and fruit thinning control is improper and natural conditions change etc. can trigger
Shedding, China are citrus big producers, a large amount of citrus sheddings are produced during annual mandarin orange planting, it is well known that citrus shedding
In same containing abundant nutritional ingredient, such as essential oil, pigment, pectin, flavonoids, dietary fiber, and general plantation
Orchard worker takes citrus shedding compost and discarded mode to handle, and a large amount of resources of production are wasted while polluting environment.In addition
The manufacturing enterprises such as existing citrus beverage, mandarin orange can in process of production, are mainly seldom entered using its pulp to tangerine peel
Row comprehensive utilization, therefore a large amount of tangerine peel is taken as waste reclamation to handle, in tangerine peel it is same containing abundant nutritional ingredient without
It is fully utilized, it is therefore necessary to citrus shedding and tangerine peel are further developed, to make full use of existing production
Resource, its economic value is improved, reduce the pollution to environment.
Show according to the study, to also containing abundant bioactive substance, including aurantiamarin, Xin Fu in citrus shedding and tangerine peel
Woods, lemon hardship etc., wherein aurantiamarin, which have, maintains osmotic pressure, strengthens capillary toughness, shortens the bleeding time, reduces cholesterol
Deng effect, the auxiliary treatment of disease of cardiovascular system is used clinically for, can cultivate a variety of prevents artery sclerosis and miocardial infarction
Medicine, be one of primary raw material of patent medicine " Maitong ", can be used as natural in the food industry, it can also be used to make up
Conduct industry, synephrine are the main actives in Bitter Orang P.E, and it can effectively prevent energy surplus (heat build-up), by wind
Qi-regulating, warm stomach promote appetite and accelerate metabolism, and it can accelerate fat metabolism and will not be as the patient using Chinese ephedra in theory
Occurring undesirable side effect like that influences cardiovascular, while is also a kind of gentle fragrant expectorant, a kind of neural tranquillizer and
The main reason for laxative for the treatment of constipation, limonin and other analog compounds are citrus fruit presentation bitter tastes, one
As be enriched with citrus plant fruit, especially with concentration highest in seed.Sterling white, bitter, crystalloid, there is certain resist
Cancer and antivirus action and other beneficial organisms activity, have antitumor, insect antifeedant, antiviral, analgesia, anti-inflammatory, hypnosis etc.
Multiple biological activities, available for functional food additives, anticancer food, insecticide, feed addictive etc., but come at present
Say, utilization of the China to citrus shedding is not abundant enough, predominantly single extraction citric acid or neohesperidin etc., if can pass through one
Bar processing technology extracts aurantiamarin, synephrine, limonin this several active ingredient simultaneously from citrus shedding and tangerine peel simultaneously,
Comprehensive utilization ratio can be then greatly improved, and then improves its economic use value, promotes the further development of citrus industry.
The content of the invention
Technical problem solved by the invention the active ingredient in a kind of citrus shedding and tangerine peel are provided extracting method,
To solve the problems, such as in above-mentioned background technology.
Technical problem solved by the invention is realized using following technical scheme：
The extracting method of active ingredient, specifically comprises the following steps in a kind of citrus shedding and tangerine peel：
1）Citrus shedding and tangerine peel are cleaned up, obtain crushing raw material after drying and crushing, raw material, petroleum ether will be crushed by weight
（kg）/ volume ratio（L）For 1:（20~30）Mixed, 70 ~ 75 DEG C of 1 ~ 2h of refluxing extraction, ceramic membrane filter once, must be filtered
Liquid, then crush raw material through being concentrated under reduced pressure to remove petroleum ether and then be dried to obtain degreasing；
2）By 1）Middle gained degreasing crush raw material and 75% ethanol by weight/volume ratio 1：（3~4）, 2 ~ 2.5h of extraction time bar
Part adverse current extraction 3 times, is extracted during extraction with ultrasonic assistant every time, is obtained filtrate with ceramic membrane filter after extraction every time, is merged
Filtrate three times, obtain extract solution；
3）By 2）Middle extract solution concentrated by rotary evaporation obtains concentrate to ethanol is free of；
4）Toward 3）Sequentially added in middle concentrate is 1 by volume:3 chloroforms and by volume be 1:5 ratio sequentially adds chlorine
Imitative and pure water, stratification；
5）By 4）Middle water layer takes out and is individually heated to 75 DEG C, filters while hot, obtains aurantiamarin crude product；Chloroform layer revolving is dry, press
Volume ratio 1:2 add acetone, and synephrine crude product and acetone filtrate are filtrated to get after crystallization；
6）By 5）In obtained aurantiamarin crude product to be concentrated in vacuo to concentration be 2 ~ 2.5mg/ml, in the first macroporous resin column on
Sample, and eluted with the first eluent, the eluent that aurantiamarin purity is more than 95% is collected, aurantiamarin is obtained after concentrate drying
Finished product, wherein the first eluent is the mixed liquor containing 50 ~ 55% ethanol and 0.0001mol/lNaoH；
7）By 5）In obtained synephrine crude product to be dissolved in water to concentration be 2 ~ 2.5mg/ml, in the second macroporous resin column on
Sample, and eluted with the second eluent, the eluent that synephrine purity is more than 95% is collected, synephrine is obtained after concentrate drying
Finished product, wherein the second eluent is the mixed liquor containing 35 ~ 40% ethanol and 0.0001mol/lNaoH；
8）By 5）In obtained acetone filtrate be spin-dried for, by volume 1：（3~4）Dissolved in purified water after, in the third-largest hole resin column
Middle loading, and pure water, 35 ~ 45% ethanol and 70 ~ 80% ethanol elutions are used successively, collect 70 ~ 80% (v/v) second
The eluent of alcohol elution, concentrates the eluent, filters, and collects limonin crude product；By limonin crude product dichloromethane knot
Crystalline substance, and with then the crystals with isopropanol crystallized out is recrystallized to give limonin finished product.
Further, the ceramic membrane aperture is with 0.2 μm.
Further, the aurantiamarin finished product purity is more than 99%.
Further, the synephrine finished product purity is more than 95%.
Further, the limonin finished product purity is more than 95%.
Further, the aurantiamarin finished product, synephrine finished product, lemon bitter principle finished product method for detecting purity are HPLC methods.
Beneficial effect：The extracting method of active ingredient in a kind of citrus shedding of the present invention and tangerine peel, by mandarin orange
Tangerine shedding and tangerine peel are made full use of, and the higher aurantiamarin finished product of purity, synephrine finished product are extracted using series of processes
And lemon bitter principle finished product, suitable for industrialized production, comprehensive utilization ratio is improved, and then its economic use value is improved, promote citrus
The further development of industry.
Embodiment
In order that the technical means, the inventive features, the objects and the advantages of the present invention are easy to understand, tie below
Close specific embodiment and the present invention is expanded on further.
Specific embodiment 1
The extracting method of active ingredient, specifically comprises the following steps in a kind of citrus shedding and tangerine peel described in the present embodiment：
1）Citrus shedding and tangerine peel are cleaned up, high temperature is dried and 60 mesh sieves are crossed after crushing obtains crushing raw material, will crush former
Material, petroleum ether are by weight（kg）/ volume ratio（L）For 1:25 are mixed, 75 DEG C of refluxing extraction 2h, 0.2um ceramic membrane filters
Once, filtrate is obtained, then raw material is crushed through being concentrated under reduced pressure to remove petroleum ether and then be dried to obtain degreasing；
2）By 1）Middle gained degreasing crush raw material and 75% ethanol by weight/volume ratio 1：3, extraction time 2h condition adverse current carry
Take 3 times, extracted every time during extraction with ultrasonic assistant, obtain filtrate with ceramic membrane filter after extraction every time, merge filtrate three times,
Obtain extract solution；
3）By 2）Middle extract solution concentrated by rotary evaporation obtains concentrate to ethanol is free of；
4）Toward 3）Sequentially added in middle concentrate is 1 by volume:3 chloroforms and by volume be 1:5 ratio sequentially adds chlorine
Imitative and pure water, stratification；
5）By 4）Middle water layer takes out and is individually heated to 75 DEG C, filters while hot, obtains aurantiamarin crude product；Chloroform layer revolving is dry, press
Volume ratio 1:2 add acetone, and synephrine crude product and acetone filtrate are filtrated to get after crystallization；
6）By 5）In obtained aurantiamarin crude product to be concentrated in vacuo to concentration be 2mg/ml, the loading in the first macroporous resin column, and
Eluted with the first eluent, collect the eluent that aurantiamarin purity is more than 95%, aurantiamarin finished product is obtained after concentrate drying,
Wherein the first eluent is the mixed liquor containing 50% ethanol and 0.0001mol/lNaoH；
7）By 5）In obtained synephrine crude product to be dissolved in water to concentration be 2mg/ml, the loading in the second macroporous resin column, and
Eluted with the second eluent, collect the eluent that synephrine purity is more than 95%, synephrine finished product is obtained after concentrate drying,
Wherein the second eluent is the mixed liquor containing 35% ethanol and 0.0001mol/lNaoH；
8）By 5）In obtained acetone filtrate be spin-dried for, by volume 1：After 3 dissolved in purified water, in the third-largest hole resin column on
Sample, and pure water, 35% ethanol and 70 % ethanol elutions are used successively, the eluent of 70 % (v/v) ethanol elution is collected,
The eluent is concentrated, is filtered, collects limonin crude product；Limonin crude product is crystallized with dichloromethane, and with then by knot
The crystals with isopropanol that crystalline substance goes out is recrystallized to give limonin finished product.
In the present embodiment, aurantiamarin finished product, synephrine finished product, lemon bitter principle finished product are using HPLC methods detection purity, through inspection
Survey, the purity of aurantiamarin finished product is 99.2%, and synephrine finished product purity is 96.5%, and limonin finished product purity is 95.8%.
Specific embodiment 2
The extracting method of active ingredient, specifically comprises the following steps in a kind of citrus shedding and tangerine peel described in the present embodiment：
1）Citrus shedding and tangerine peel are cleaned up, high temperature is dried and 60 mesh sieves are crossed after crushing obtains crushing raw material, will crush former
Material, petroleum ether are by weight（kg）/ volume ratio（L）For 1:30 are mixed, 70 DEG C of refluxing extraction 2.5h, 0.2um ceramic membrane mistakes
Filter once, obtains filtrate, then crush raw material through being concentrated under reduced pressure to remove petroleum ether and then be dried to obtain degreasing；
2）By 1）Middle gained degreasing crush raw material and 75% ethanol by weight/volume ratio 1：4, extraction time 2.5h condition adverse current
Extraction 3 times, extracted every time during extraction with ultrasonic assistant, obtain filtrate with ceramic membrane filter after extraction every time, merging is filtered three times
Liquid, obtain extract solution；
3）By 2）Middle extract solution concentrated by rotary evaporation obtains concentrate to ethanol is free of；
4）Toward 3）Sequentially added in middle concentrate is 1 by volume:3 chloroforms and by volume be 1:5 ratio sequentially adds chlorine
Imitative and pure water, stratification；
5）By 4）Middle water layer takes out and is individually heated to 75 DEG C, filters while hot, obtains aurantiamarin crude product；Chloroform layer revolving is dry, press
Volume ratio 1:2 add acetone, and synephrine crude product and acetone filtrate are filtrated to get after crystallization；
6）By 5）In obtained aurantiamarin crude product to be concentrated in vacuo to concentration be 2.5mg/ml, the loading in the first macroporous resin column,
And eluted with the first eluent, collect the eluent that aurantiamarin purity is more than 95%, obtained after concentrate drying aurantiamarin into
Product, wherein the first eluent is the mixed liquor containing 55% ethanol and 0.0001mol/lNaoH；
7）By 5）In obtained synephrine crude product to be dissolved in water to concentration be 2.5mg/ml, the loading in the second macroporous resin column,
And eluted with the second eluent, collect the eluent that synephrine purity is more than 95%, obtained after concentrate drying synephrine into
Product, wherein the second eluent is the mixed liquor containing 40% ethanol and 0.0001mol/lNaoH；
8）By 5）In obtained acetone filtrate be spin-dried for, by volume 1：After 3 dissolved in purified water, in the third-largest hole resin column on
Sample, and pure water, 45% ethanol and 80 % ethanol elutions are used successively, the eluent of 80% (v/v) ethanol elution is collected,
The eluent is concentrated, is filtered, collects limonin crude product；Limonin crude product is crystallized with dichloromethane, and with then by knot
The crystals with isopropanol that crystalline substance goes out is recrystallized to give limonin finished product.
In the present embodiment, aurantiamarin finished product, synephrine finished product, lemon bitter principle finished product are using HPLC methods detection purity, through inspection
Survey, the purity of aurantiamarin finished product is 99.6%, and synephrine finished product purity is 95.2%, and limonin finished product purity is 96.5%.
General principle, principal character and the advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
Claims (6)
1. the extracting method of active ingredient in a kind of citrus shedding and tangerine peel, it is characterised in that comprise the following steps：
1）Citrus shedding and tangerine peel are cleaned up, obtain crushing raw material after drying and crushing, raw material, petroleum ether will be crushed by weight
（kg）/ volume ratio（L）For 1:（20~30）Mixed, 70 ~ 75 DEG C of 1 ~ 2h of refluxing extraction, ceramic membrane filter once, must be filtered
Liquid, then crush raw material through being concentrated under reduced pressure to remove petroleum ether and then be dried to obtain degreasing；
2）By 1）Middle gained degreasing crush raw material and 75% ethanol by weight/volume ratio 1：（3~4）, 2 ~ 2.5h of extraction time bar
Part adverse current extraction 3 times, is extracted during extraction with ultrasonic assistant every time, is obtained filtrate with ceramic membrane filter after extraction every time, is merged
Filtrate three times, obtain extract solution；
3）By 2）Middle extract solution concentrated by rotary evaporation obtains concentrate to ethanol is free of；
4）Toward 3）Sequentially added in middle concentrate is 1 by volume:3 chloroforms and by volume be 1:5 ratio sequentially adds chlorine
Imitative and pure water, stratification；
5）By 4）Middle water layer takes out and is individually heated to 75 DEG C, filters while hot, obtains aurantiamarin crude product；Chloroform layer revolving is dry, press
Volume ratio 1:2 add acetone, and synephrine crude product and acetone filtrate are filtrated to get after crystallization；
6）By 5）In obtained aurantiamarin crude product to be concentrated in vacuo to concentration be 2 ~ 2.5mg/ml, in the first macroporous resin column on
Sample, and eluted with the first eluent, the eluent that aurantiamarin purity is more than 95% is collected, aurantiamarin is obtained after concentrate drying
Finished product, wherein the first eluent is the mixed liquor containing 50 ~ 55% ethanol and 0.0001mol/lNaoH；
7）By 5）In obtained synephrine crude product to be dissolved in water to concentration be 2 ~ 2.5mg/ml, in the second macroporous resin column on
Sample, and eluted with the second eluent, the eluent that synephrine purity is more than 95% is collected, synephrine is obtained after concentrate drying
Finished product, wherein the second eluent is the mixed liquor containing 35 ~ 40% ethanol and 0.0001mol/lNaoH；
8）By 5）In obtained acetone filtrate be spin-dried for, by volume 1：（3~4）Dissolved in purified water after, in the third-largest hole resin column
Middle loading, and pure water, 35 ~ 45% ethanol and 70 ~ 80% ethanol elutions are used successively, collect 70 ~ 80% (v/v) second
The eluent of alcohol elution, concentrates the eluent, filters, and collects limonin crude product；By limonin crude product dichloromethane knot
Crystalline substance, and with then the crystals with isopropanol crystallized out is recrystallized to give limonin finished product.
2. the extracting method of active ingredient in a kind of citrus shedding according to claim 1 and tangerine peel, it is characterised in that institute
It is with 0.2 μm to state ceramic membrane aperture.
3. the extracting method of active ingredient in a kind of citrus shedding according to claim 1 and tangerine peel, it is characterised in that institute
Aurantiamarin finished product purity is stated more than 99%.
4. the extracting method of active ingredient in a kind of citrus shedding according to claim 1 and tangerine peel, it is characterised in that institute
Synephrine finished product purity is stated more than 95%.
5. the extracting method of active ingredient in a kind of citrus shedding according to claim 1 and tangerine peel, it is characterised in that institute
Limonin finished product purity is stated more than 95%.
6. the extracting method of active ingredient in a kind of citrus shedding according to claim 1 and tangerine peel, it is characterised in that institute
It is HPLC methods to state aurantiamarin finished product, synephrine finished product, lemon bitter principle finished product method for detecting purity.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108642117A (en) * | 2018-03-06 | 2018-10-12 | 北京颐方生物科技有限公司 | A method of extraction limonin and Nomilin |
| CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102442916A (en) * | 2010-10-01 | 2012-05-09 | 华中农业大学 | Method for extracting natural activated products from orange drops |
| CN103172685A (en) * | 2013-01-30 | 2013-06-26 | 向华 | Method for extracting hesperidin and synephrine from immature bitter oranges |
| CN106831914A (en) * | 2017-04-17 | 2017-06-13 | 广西壮族自治区梧州食品药品检验所 | A kind of method that ASE methods extract aurantiamarin in dried orange peel |
-
2017
- 2017-07-20 CN CN201710596989.0A patent/CN107383131A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102442916A (en) * | 2010-10-01 | 2012-05-09 | 华中农业大学 | Method for extracting natural activated products from orange drops |
| CN103172685A (en) * | 2013-01-30 | 2013-06-26 | 向华 | Method for extracting hesperidin and synephrine from immature bitter oranges |
| CN106831914A (en) * | 2017-04-17 | 2017-06-13 | 广西壮族自治区梧州食品药品检验所 | A kind of method that ASE methods extract aurantiamarin in dried orange peel |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108642117A (en) * | 2018-03-06 | 2018-10-12 | 北京颐方生物科技有限公司 | A method of extraction limonin and Nomilin |
| CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
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Application publication date: 20171124 |