CN105418705A - Method for extracting hesperidin and neohesperidin from citrus peels and fruits - Google Patents
Method for extracting hesperidin and neohesperidin from citrus peels and fruits Download PDFInfo
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- CN105418705A CN105418705A CN201510892977.3A CN201510892977A CN105418705A CN 105418705 A CN105418705 A CN 105418705A CN 201510892977 A CN201510892977 A CN 201510892977A CN 105418705 A CN105418705 A CN 105418705A
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- 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
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Abstract
The invention provides a method for extracting hesperidin and neohesperidin from citrus peels and fruits. The method comprises the following steps: drying and grinding citrus peels and fruits of immature citron, mixing in a ratio of 1 to 1, and performing percolation extraction; extracting dregs with alkaline liquor, regulating the extract with acid, precipitating, washing, dissolving with 65% ethanol, and recrystallizing to obtain a hesperidin product; performing chromatography on the percolating liquid through strongly acidic styrene type cation columns, washing, and feeding into macro-porous resin; and washing with water, washing with 20% lower alcohol, washing with 65% lower alcohol, concentrating the eluent, assisting separation with 5.0% (NH4)2SO4/NaCl to obtain a coarse crystal, and recrystallizing to obtain a neohesperidin product. The product has the content of hesperidin being 98.0 percent and the yield being over 6.0 percent, and has the content of neohesperidin being 90.0 percent and the yield being over 2.0 percent. Temperature is controlled to be lower than 15 DEG C in crystallization and recrystallization.
Description
Technical field
The present invention relates to field of plant extraction, especially a kind of method extracting flavones from peel of Citrus reticulata Blanco, fruit.
Background technology
Oranges and tangerines are the important plants of Rutaceae Citrus, and mainly utilize its pulp and seldom fully utilize effect and pericarp, great majority are taken as waste reclamation process.Because citrus fruit, skin contain more biologically active substance, therefore more and more extensive to its utilization.Hesperidin (Hesperidin) is the natural flavone compounds in orange peel, and the Hesperidin purity adopting alkali leaching acid-precipitation method to extract from navel orange is 80.3%, and yield is 1.55%.Neohesperidin (Neohesperidin) is the glucosides formed by Hesperitin and neohesperidose, and the method extracting neohesperidin at present comprises ultrasound assisted extraction method, soxhlet extraction and water-bath reflux extraction.Synephrine (Synephrine) is the main component of dried immature fruit of citron orange alkaloids substance, and the content of synephrine reduces along with the maturation of citrusfruit, therefore generally chooses green fruit and shedding and is used as extracting raw material; The extracting method of synephrine has heating reflux method, ultrasonic extraction and microwave loss mechanisms.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of method of efficient extraction and isolation Hesperidin, neohesperidin simultaneously from dried immature fruit of citron orange fruitlet and peel of Citrus reticulata Blanco mixture, by peel of Citrus reticulata Blanco and dried immature fruit of citron orange fruitlet dry, pulverize, after the mixing of 1:1 ratio, use water seepage pressure effects; Then slag of getting it filled carries out Hesperidin extraction, and content of hesperidin can reach more than 98%, and yield is more than 6.0%; Get percolate and carry out neohesperidin extraction, obtain neohesperidin extractive content and reach more than 90%, yield is more than 2.0%.In order to solve this technical problem, the concrete implementation step of this patent is as follows:
One, peel of Citrus reticulata Blanco, the pre-treatment of bigarabe dried immature fruit of citron orange fruitlet
Collect peel of Citrus reticulata Blanco, drying, pulverizing, sieve for subsequent use; Collect the drying of dried immature fruit of citron orange fruitlet, pulverize, sieve for subsequent use.By the 1:1 ratio mixing in mass ratio of citrus peel meal and dried immature fruit of citron orange fruitlet powder, be placed in extractor, in solid-liquid ratio 1:(10-30) ratio, carry out seepage pressure effects with the aqueous ethanolic solution of 30%-50%, control temperature 40-45 DEG C, seepage pressure effects 10-12h; Filter; Then in filtrate, add the polygalacturonase of 0.01-0.1%, stir 30min at 50 DEG C, then temperature is transferred to 70 DEG C, process 15-30min, kills polygalacturonase; Then filter, the dregs of a decoction are separated with filtrate; The dregs of a decoction are used for Hesperidin and extract, and filtrate is used for neohesperidin and extracts.
The described screen cloth sieved is 10 orders or 60 orders or 100 orders;
Described seepage pressure effects can carry out 3 times.
Two, Hesperidin extracting and developing, purifying
Be 10.0-11.0 dipping by lye by above-mentioned dregs of a decoction pH value, extract; It is 2.0-3.0 that gained extracting solution HCl is adjusted to pH value, places, precipitation; Precipitation being washed with water to neutrality, with solid-liquid ratio 1:(50-60) g/mL adds methyl alcohol, is 10.0-11.0 with dilute NaOH solution tune system pH, 30min is reacted at 30 DEG C, natural filtration, then adjust filtrate pH to be 3.0-5.0 with dilute hydrochloric acid, below 15 DEG C, leave standstill 12h recrystallization; Crystal after recrystallization is Hesperidin product.In this product, content of hesperidin can reach 98.0%, and Hesperidin yield is more than 6.0%.
Described alkali lye is NaOH or Ca(OH)
2.
Described crystallization and recrystallization, temperature will control below 15 DEG C, to guarantee Hesperidin yield and purity.
Three, neohesperidin extracting and developing, purifying
The filtrate of getting described in step one crosses strongly acidic styrene's type cation seperation column, and collection of ions post effluent liquid, then washes with water.By ion column effluent liquid and water lotion mixing, enter macroporous adsorbent resin, after washing, first with 20% low-carbon alcohol washing, then use 65% low-carbon alcohol wash-out, elutriant is concentrated, places below 15 DEG C, with (NH
4)
2sO
4/ NaCl helps and analyses, and obtains neohesperidin crude product; Neohesperidin crude product being washed with water to neutrality, with solid-liquid ratio 1:(50-60) g/mL adds methyl alcohol, is 10.0-11.0 with dilute NaOH solution tune system pH, 30min is reacted at 30 DEG C, natural filtration, then adjust filtrate pH to be 3.0 with dilute hydrochloric acid, below 15 DEG C, leave standstill 12h recrystallization; Separate out off-white color needle-like crystal; Suction filtration, dries, obtains neohesperidin; Detect with HPLC, in this product, content of hesperidin can reach more than 90.0%, and Hesperidin yield is more than 2.0%.
Described strongly acidic styrene's type cation seperation column preferably 001 × 7 cation seperation column;
The preferred D101 of described macroporous adsorbent resin;
Described crystallization and recrystallization, temperature will control below 15 DEG C, to guarantee neohesperidin yield and purity.
Described diacolation, extraction, enzymolysis, filtration, chromatographic adsorption, wash-out, crystallization, recrystallization are all known technology.
The present invention has following advantages and characteristic:
1, utilize resources synthetically
Dried immature fruit of citron orange fruitlet and peel of Citrus reticulata Blanco are carried out seepage pressure effects in the mixing of 1:1 ratio, extracts Hesperidin in the dregs of a decoction after extraction, in filtrate, extract neohesperidin, achieve Hesperidin, neohesperidin simultaneous synthesis extracts.
2, combination technique is novel
By the technical program, dried immature fruit of citron orange fruitlet, the citrus peel meal 1:1 ratio in mass ratio that minces are mixed, after solid-liquid ratio seepage pressure effects, Hesperidin is extracted from the dregs of a decoction, from filtrate, extract neohesperidin, obtaining content of hesperidin can reach more than 98.0%, and yield is more than 6.0%; Obtain neohesperidin extractive content and can reach more than 90%, neohesperidin yield is more than 2.0%.Especially Hesperidin and neohesperidin extract simultaneous extraction, and be utilize diacolation filtrate, neohesperidin adopts first positively charged ion chromatography column, D101 macroporous resin column again, then adopts 20% low-carbon alcohol washing, then uses 65% low-carbon alcohol wash-out, get 65% low-carbon alcohol elutriant to concentrate, with (the NH of concentrated solution quality 5%
4)
2sO
4/ NaCl helps and analyses, crystallization; By coarse-grain dissolve with methanol, obtain product through recrystallization.All crystallizations and re-crystallization step are all carry out below 15 DEG C.These technical characteristics are combined, and Hesperidin and neohesperidin extract create beyond thought effect on content and yield 2 indexs.These results are that each technical characterstic of technical combinations scheme kind is supported mutually, acting in conjunction just realizes, and known technology is not reported, also the technology of this Welded joint is not enlightened, and is not simple superposition, have outstanding substantive distinguishing features and significant progress.
Embodiment
The following stated example understands the present invention in detail.
Embodiment 1
Pre-treatment
Using the dried immature fruit of citron orange fruitlet of bigarabe third time physiological fruit drop as extraction raw material, dry, pulverize with high-speed multifunctional pulverizer, get crushed material and cross 10 object sieves, for subsequent use.Bitter orange peer be dry, pulverize, cross 10 mesh sieves, for subsequent use.Accurately take dried immature fruit of citron orange fruitlet crushed material 25.0g and bitter orange peer crushed material 25.0g is placed in beaker, add 500mL30% aqueous ethanolic solution, soak water-bath at putting into water-bath 44 DEG C and extract 10h, filter, obtain extracting solution.In extracting solution, add 0.5g pectinase treatment, stir 30min at 50 DEG C, then water-bath is adjusted to 70 DEG C, process 30min, by abundant for polygalacturonase deactivation.After its cooling under gauze is auxiliary, use double-layer filter paper suction filtration, obtain filtrate and filter residue, filter residue is for extracting Hesperidin, and filtrate is for extracting neohesperidin.
Hesperidin extracts
Get above-mentioned filter residue 100g, add the water of 2000ml, at 30 DEG C, add 1.75gCa (OH) while stirring
2, stir after 0.5h and filter, get filtrate and add dilute hydrochloric acid and adjust system pH to be 3.0, control temperature is at 12h standing 15 DEG C below; Separate out coarse crystal; Suction filtration, dries to obtain Hesperidin crude product.Add methyl alcohol with solid-liquid ratio 1:60g/mL, adjust system pH to be 10.0 with dilute NaOH solution, below 30 DEG C, react 30min, natural filtration, then adjust filtrate pH to be 3.0 with dilute hydrochloric acid, below 15 DEG C, leave standstill 12h recrystallization; After recrystallization, filter, dry, obtain Hesperidin crystal, the yield of Hesperidin is 6.06%, and purity is 98.15%.
Neohesperidin is extracted
Get pre-treatment filtrate and cross D101 macroporous adsorptive resins, washing, uses 30% ethanol and 70% ethanol gradient elution successively.Collect 70% alcohol eluen, be condensed into medicinal extract.In medicinal extract, add the ammonium sulfate solids of 5% massfraction, heat while stirring, after boiling, stop heating, cooling; Crystallization 12h below 15 DEG C, obtains neohesperidin crude product.
Neohesperidin crude product is washed with water to neutrality, adds methyl alcohol with solid-liquid ratio 1:50g/mL, adjust system pH to be 10.0 with dilute NaOH solution, react 30min at 30 DEG C, natural filtration, then adjust filtrate pH to be 3.0 with dilute hydrochloric acid, below 15 DEG C, leave standstill 12h, carry out recrystallization, separate out off-white color needle-like crystal; Suction filtration, dries, obtains neohesperidin; Recording purity through HPLC is 90.07%, neohesperidin yield 2.06%.
Embodiment 2
Pre-treatment
Using the dried immature fruit of citron orange fruitlet of bigarabe third time physiological fruit drop as extraction raw material, dry, pulverize with high-speed multifunctional pulverizer, get crushed material and cross 100 object sieves, for subsequent use; Bitter orange peer be dry, pulverize, cross 100 mesh sieves, for subsequent use.Accurately take dried immature fruit of citron orange fruitlet crushed material 50.0g and bitter orange peer crushed material 50.0g is placed in beaker, add 1000mL50% aqueous ethanolic solution, after stirring, soak water-bath at putting into water-bath 40 DEG C and extract 12h, filter.In extracting solution, add 0.15g pectinase treatment, at 50 DEG C, stir 30min, then water-bath is adjusted to 70 DEG C, process 20min.Line gauze coarse filtration after its cooling, then use double-layer filter paper suction filtration, obtain filtrate and filter residue.Filter residue is being repeated extraction 2 times, merging filtrate; Filter residue is for extracting Hesperidin, and filtrate is for extracting neohesperidin and synephrine.
Hesperidin extracts
Get above-mentioned filter residue 100g, extract with alkali extraction and acid precipitation; Add the water 3000ml of solid-liquid ratio 1:30g/mL, at 30 DEG C, add 9.2gCa (OH) while stirring
2, stir after 0.5h and filter, get filtrate and add appropriate dilute hydrochloric acid and adjust system pH to be 2.0, leave standstill 12h; Crystallization, suction filtration, dries to obtain Hesperidin crude product.Add methyl alcohol with solid-liquid ratio 1:60g/mL, react 30min, natural filtration at adjusting system pH to be 10.0,30 DEG C with dilute NaOH solution, then adjust filtrate pH to be 5.0 with dilute hydrochloric acid, leave standstill 12h recrystallization; After recrystallization, filter, dry, weigh, obtain Hesperidin sterling, purity is 98.16%, and yield is 6.14%.
Neohesperidin is extracted
The filtrate of getting after pre-treatment merging crosses D101 macroporous adsorptive resins, and washing, uses 30% ethanol and 70% ethanol gradient elution successively.Collect 70% alcohol eluen, be condensed into medicinal extract.In medicinal extract, add the ammonium sulfate solids of 5% massfraction, heat while stirring, stop heating after boiling, cooling, crystallization 12h below 15 DEG C, obtains neohesperidin crude product.Neohesperidin crude product is placed in the beaker of clean dried, in beaker, adds methyl alcohol with the ratio of solid-liquid ratio 1:60g/mL, stir evenly; React 30min, natural filtration at adjusting system pH to be 11.0,30 DEG C with dilute NaOH solution, then adjust filtrate pH to be 2.0 with dilute hydrochloric acid, below 15 DEG C, leave standstill 12h, carry out recrystallization; Suction filtration, dries, obtains neohesperidin; Recording purity through HPLC is 91.15%, neohesperidin yield 2.28%.
Claims (4)
1. from peel of Citrus reticulata Blanco, fruit, extract a method for Hesperidin and neohesperidin, it is characterized in that: adopt following processing step:
A pre-treatment
With bitter orange peer and bigarabe third time physiological fruit drop dried immature fruit of citron orange fruitlet for raw material, drying, pulverizing, sieve, example is the ratio of 1:1 in mass ratio, take bitter orange peer crushed material and dried immature fruit of citron orange fruitlet crushed material, use 30%-50% aqueous ethanolic solution, according to quality solid-liquid ratio 1:(10-30), carry out seepage pressure effects 10-12h at 40-45 DEG C; Be added into polygalacturonase in the ratio of 0.01%-0.1%, stir 30min at 40-50 DEG C, then temperature regulating to 70 DEG C, process 15-30min; Then filter; The dregs of a decoction can repeat extraction 3 times; The dregs of a decoction obtained are for extracting Hesperidin, and filtrate is for extracting neohesperidin;
B Hesperidin extracts
Being the NaOH solution of 10.0-11.0 by pH value, is 1:(5-10 according to solid-liquid ratio) ratio soak the dregs of a decoction, extract;
It is 2.0-3.0 that gained extracting solution HCl is adjusted to pH value, places below 15 DEG C, precipitation;
Throw out is washed with water to neutrality, then uses 65% dissolve with ethanol, place below 15 DEG C, recrystallization; Crystal after recrystallization is Hesperidin product;
C neohesperidin extracting and developing, purifying
Get filtrate described in steps A and cross strongly acidic styrene's type cation seperation column, then wash with water, collect effluent liquid and water lotion;
By ion column effluent liquid and water lotion mixing, enter D101 macroporous adsorbent resin; After washing, first use 20% low-carbon alcohol wash-out, then use 65% low-carbon alcohol gradient elution, collect 65% low-carbon alcohol elutriant;
65% low-carbon alcohol washing lotion is concentrated, places below 15 DEG C, with (the NH of concentrated solution quality 5.0%
4)
2sO
4/ NaCl helps and analyses, and obtains neohesperidin crude product;
Neohesperidin crude product being washed with water to neutrality, with solid-liquid ratio 1:(50-60) g/mL adds methyl alcohol, is 10.0-11.0 with dilute NaOH solution tune system pH, react 30min at 30 DEG C, natural filtration, then adjust filtrate pH to be 2.0-3.0 with dilute hydrochloric acid, leave standstill below 15 DEG C, recrystallization; Separate out off-white color needle-like crystal; Suction filtration, dries, obtains neohesperidin.
2. method according to claim 1, is characterized in that: sieve described in steps A, and the order number of screen cloth is 10 orders or 60 orders or 100 orders.
3. method according to claim 1, is characterized in that: described in step C, strongly acidic styrene's type cation seperation column is 001 × 7 cation seperation column.
4. method according to claim 1, is characterized in that: described macroporous resin is D101.
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Cited By (5)
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| WO2018010170A1 (en) * | 2016-07-15 | 2018-01-18 | 刘力 | Novel embodiment of flavonoid, and composition and application thereof |
| CN108822169A (en) * | 2018-09-18 | 2018-11-16 | 湘西华方制药有限公司 | The heavy aurantiamarin that alcohol extracting prepares the method for crystallising of heavy aurantiamarin and is prepared |
| CN109730300A (en) * | 2019-03-01 | 2019-05-10 | 华中农业大学 | A kind of method and a kind of starch gel hardening agent and its application preparing starch gel hardening agent low in calories with citrus peel residue |
| 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 |
| CN113651791A (en) * | 2021-09-01 | 2021-11-16 | 湖南华诚生物资源股份有限公司 | Method for separating hesperetin from immature bitter orange |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN109730300A (en) * | 2019-03-01 | 2019-05-10 | 华中农业大学 | A kind of method and a kind of starch gel hardening agent and its application preparing starch gel hardening agent low in calories with citrus peel residue |
| 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 |
| CN113651791A (en) * | 2021-09-01 | 2021-11-16 | 湖南华诚生物资源股份有限公司 | Method for separating hesperetin from immature bitter orange |
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Effective date of registration: 20220909 Address after: 427000 Economic Development Zone C, Zhangjiajie City, Hunan Province Patentee after: ZHANGJIAJIE JIYUAN TECHNOLOGY Co.,Ltd. Address before: 541004 Liuhe Road, the Guangxi Zhuang Autonomous Region, 82 Liuhe Road 35 building 3 unit 202 room. Patentee before: Zhou Zhide |