CN101007827A - Method of extracting sesamin from seasame cake - Google Patents
Method of extracting sesamin from seasame cake Download PDFInfo
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- CN101007827A CN101007827A CNA2007100198629A CN200710019862A CN101007827A CN 101007827 A CN101007827 A CN 101007827A CN A2007100198629 A CNA2007100198629 A CN A2007100198629A CN 200710019862 A CN200710019862 A CN 200710019862A CN 101007827 A CN101007827 A CN 101007827A
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- sesame
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- seasame
- ethyl acetate
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Abstract
The invention relates to a method for preparing sesamin from seasame cake. It comprises following steps: taking side product sesameseed meal in benne oil factory as raw material, removing left oil using skellysolve B; taking oil-removed seasame cake as raw material, extracting sesamin coarse extract with methanol; separating and purifying with silica gel column chromatography method and getting sesamin. The productivity of sesamin is 1.57%, and purity id 88.02%. The invention makes use of sesameseed meal to prepare seasame that possesses multiple physiologically active substance, so the market prospect is wide.
Description
Technical field
A kind of method for preparing sesamin from sesame cake meal relates to the extraction and purification of sesamin.With method of the present invention sesame cake meal is fully utilized, therefrom preparation has the sesamin of multiple physiological active functions, has broad application prospects.
Background technology
Sesame is as important oil crops, plant with a long history, especially extensively plantation of country in Asia and Africa Development.Contain 0.5%～1.0% Lignanoids compounds in the sesame approximately, and most importantly sesamin or sesamin (sesamin) account for more than 50% of lignanoid's content.The Japan scholar sesame lignanoid that goes out of isolation identification has sesamin, episesamin, sesamin phenol, sesamolin, sesame woods phenol element, sesamol and rosin spirit etc.Recently relevant sesame lignanoid antioxygenation with and studies show that of a series of physiological functions aspects such as interaction of in vivo metabolism and some biological enzyme, sesame lignanoid has Mulberry Extract, suppresses lipid peroxidation, reducing cholesterol, hypertension, antibiotic, protect physiological actions such as liver, inhibition mammary cancer and immuno-stimulating.
Sesamin is sheet or powdery white solid normally, is lipid-soluble substance, and water insoluble, bronsted lowry acids and bases bronsted lowry is soluble in organic solvents such as methyl alcohol.Sesamin through the organic solvent crystallization treatment is generally white, needle-shaped crystals.Sesamin has great application prospect owing to have multiple physiological active functions in agricultural, food service industry, and highly purified sesamin is applied in health care and pharmaceutical industries gradually.
The method for preparing at present sesamin mainly contains following several:
Wang Xingguo (Chinese patent CN1594310A) etc. has reported that be raw material with the sesame crude oil after the sesame squeezing through lower floor's product (sesame oil residue) that standing demix obtains, utilize the sesame oil of n-hexane extraction remnants, be raw material with this sesame oil that reclaims again, slightly carry product with methyl alcohol or extraction using alcohol sesamin, with ethanol the sesamin crude extract is carried out recrystallization again.
Zhu Xiaojun (Chinese patent CN1535970A) has reported the column container of sesame oil by the filling chromosorb, crosses column shape container wash-out oiliness impurity with fat-soluble elutriant simultaneously, and elutriant is washed till the stripping of column shape container bottom colour band.Be the proposition process of sesamin subsequently, promptly collect the sorbent material colour band layer that occupy the column shape container middle part, utilize the extractives that contains sesamin in the outstanding belt of solvent extraction that dissolves sesamin again.
A China fir Pu person of refined tastes (Chinese patent CN1170603A) etc. has reported a kind of method of separating sesamin-class compounds from the overhead product that contains sesamin-class compounds in fact that the wet distillation sesame oil that reduces pressure down obtains, can be with the method for the good separation sesamin-class compounds of high purity and high-recovery, efficient.
More than about the development and use and the patent of sesamin be raw material all basically with sesame, sesame oil or sesame oil residue, all do not relate to the problem of utilizing that sesame is produced lignanoid in the greasy by product sesame cake meal.
Summary of the invention
The purpose of this invention is to provide a kind of method for preparing sesamin of from sesame cake meal, extracting.Byproduct is the numb cake/dregs of rice (milling process) and the dregs of linseeds or sesame seeds (water is for method) behind the sesame system oil, often be used as waste material in early days and abandon, or as fertilizer sources, then most of now as protein fodder, make an addition in the animal daily ration.Also contain many functional ingredient in these depleted sesame-send cakes.Sesame-send cake is carried out the utilization again of Biological resources, therefrom extracts sesamin with different physiological roles, not only can improve sesame added value and also can be for developing natural, efficient, nontoxic antioxidant.
Technical scheme of the present invention:
(1) test records and contains about 14% grease in the sesame cake meal, and these remaining greases can influence the extraction yield of lower alcohol to sesamin, so the present invention is at first with sesame-send cake drying, pulverizing, the normal hexane, pentane, heptane or its mixture that add 2～5 times of volumes then, degreasing 1～3 time, each 3～6h adopts vacuum filtration to carry out solid-liquid separation, removes the remaining grease in the sesame-send cake;
(2) wash 2～3 times with distilled water or 3～10% sodium chloride aqueous solution removing greasy sesame-send cake in the step 1, remove the carbohydrate and the protein of solubility, then in oven dry below 70 ℃;
(3) sesame-send cake that step 2 is dried adds methyl alcohol, ethanol, ethyl acetate or the acetone etc. of 2～10 times of volumes, and lixiviate is 1～3 time under 35～75 ℃ of temperature, and each 2～10 hours, solid-liquid separation;
(4) the filtrate rotary evaporation with step 3 is concentrated into the medicinal extract shape, removes solvent;
(5) step 4 gained medicinal extract is suspended with an amount of hot water, use ethyl acetate extraction 1～3 time, gained extraction liquid rotary evaporation is concentrated obtain acetic acid ethyl ester extract;
(6) adopt sample on the wet method dress post dry method, take by weighing silica gel for chromatography (200～300 order) and be loaded in the silica gel column chromatography, get sample on an amount of acetic acid ethyl ester extract;
(7) adopt the mixed solution of petrol ether/ethyl acetate different volumes ratio as eluent, by gradient 100/0,20/1,16/1,8/1,4/1,2/1,1/1,1/2,1/3,1/4 and 0/100 wash-out successively, adopt tlc (Chinese Pharmacopoeia 2005 editions) to detect target component.
(8) adopt high performance liquid chromatography to detect the purity of purified product sesamin.Chromatographic condition: chromatographic column Agilent ODS2 (150mm * 4.6mm, 5 μ m), mobile phase methanol-water (68:32), flow velocity 1mL/min, 30 ℃ of column temperatures, detector DAD diode-array detector detects wavelength 287nm.
Mainly owing to its endogenous lignan component that contains, the lignanoid in sesame, sesame oil, sesame oil deodorization thing and the sesame cake meal is one of main source of plant-sourced antioxidant to the strong anti-oxidation performance of sesame oil.The present invention founded a kind of from sesame cake meal the production technique of high efficiency extraction Gingeli antioxidation composition, realized the comprehensive utilization of sesame cake meal.Compare with sesame, sesame oil and the invention of the middle extraction polyphenoils of sesame oil deodorization thing, have advantages such as the cheap and wide material sources of cost of material.
From sesame cake meal, extract these oxidation-resistant active ingredients, after refinement treatment, add again in the food, not only can prevent or suppress the oxidative rancidity of food, but also can strengthen the nourishing function of food human body.
Embodiment
Below in conjunction with embodiment the present invention is further elaborated.
Embodiment 1
The 1000g sesame-send cake, the normal hexane of 2 times of volumes of adding, 2 times/10h of degreasing; Use distilled water wash then 3 times, in 50 ℃ of vacuum-dryings; The sesame cake meal of degreasing adds the methyl alcohol of 4 times of volumes, 2 times/6h of 25 ℃ of lixiviates, solid-liquid separation; The filtrate rotary evaporation concentrate medicinal extract 39.6g; With institute's medicinal extract small amount of thermal aqueous suspension, use ethyl acetate extraction 2 times, rotary evaporation concentrates and obtains the 19.6g acetic acid ethyl ester extract then.
Embodiment 2
The 1000g sesame-send cake, the pentane of 3 times of volumes of adding, 3 times/3h of degreasing; The washing of 3% sodium chloride aqueous solution is 2 times then, in 60 ℃ of oven dry; The sesame cake meal of degreasing adds the methyl alcohol of 8 times of volumes, 3 times/6h of 45 ℃ of lixiviates, solid-liquid separation; The filtrate rotary evaporation concentrate medicinal extract 41.8g; With institute's medicinal extract small amount of thermal aqueous suspension, use ethyl acetate extraction 3 times, rotary evaporation concentrates and obtains the 20.5g acetic acid ethyl ester extract then.
Embodiment 3
The 1000g sesame-send cake, the normal hexane of 5 times of volumes of adding, 3 times/6h of degreasing; Then with 10% sodium chloride aqueous solution washing 3 times, in 70 ℃ of oven dry; The sesame cake meal of degreasing adds 8 times of volume of ethanol, 2 times/6h of 60 ℃ of lixiviates, solid-liquid separation; The filtrate rotary evaporation concentrate medicinal extract 37.4g; With institute's medicinal extract small amount of thermal aqueous suspension, use ethyl acetate extraction 3 times, rotary evaporation concentrates and obtains the 17.3g acetic acid ethyl ester extract then.
Embodiment 4
Taking by weighing the 85g silica gel for chromatography is loaded in 20 * 600 the glass chromatography column; Accurately take by weighing the 2.02g acetic acid ethyl ester extract that embodiment 1 prepares, add the 3.0g silica gel mixed sample, sample on the dry method; Adopt binary solvent elution system petrol ether/ethyl acetate by gradient (100/0,20/1,16/1,8/1,4/1,2/1,1/1,1/2,1/3,1/4,0/100) wash-out; Adopt the thin-layer chromatography detection method to find in 4/1 elutriant, to obtain the target component sesamin; Elutriant is concentrated, separate out precipitation naturally, drying is weighed.
Finally obtain throw out 31.9mg, yield is 1.57%; Through its purity of high effective liquid chromatography for measuring is 88.02%.
Embodiment 5
Taking by weighing the 130g silica gel for chromatography is loaded in 33 * 600 the glass chromatography column; Accurately take by weighing the 5.03g acetic acid ethyl ester extract that embodiment 1 prepares, add the 7.07g silica gel mixed sample and be splined on capital; Adopt petrol ether/ethyl acetate by gradient (100/0,20/1,16/1,8/1,4/1,2/1,1/1,1/2,1/3,1/4,0/100) wash-out; The thin-layer chromatography detection method finds to obtain the target component sesamin in 4/1 elutriant; Elutriant is concentrated, separate out precipitation naturally, drying is weighed.
Finally obtain throw out 51.8mg, yield is 1.02%; Through its purity of high effective liquid chromatography for measuring is 62.8%.
Embodiment 6
The sesamin that embodiment 5 is obtained is made into the methanol solution that concentration is respectively 1mg/mL, 2mg/mL, 3mg/mL, 4mg/mL and 5mg/mL.Get the sesamin methanol solution 0.1mL of above-mentioned different concns, adding 3.9mL concentration is the DPPH methanol solution of 2.5mg/mL, behind the reaction 30min, measures its absorbancy at the 515nm place.Calculate the clearance rate of sesamin to DPPH according to formula, the result is as shown in table 1.
Table 1 different concns sesamin solution is to the clearance rate of DPPH
| Concentration (mg/mL) | 1 | 2 | 3 | 4 | 5 |
| Clearance rate % | 12.84 | 17.91 | 18.14 | 18.67 | 18.82 |
Claims (1)
1. preparation method who extracts sesamin from sesame cake meal is characterized in that:
(1) at first with sesame-send cake drying, pulverizing, add normal hexane, pentane, heptane or its mixture of 3 times of volumes then, degreasing 2 times adopts vacuum filtration to carry out solid-liquid separation, removes the remaining grease in the sesame-send cake;
(2) wash 2～3 times removing the sodium chloride aqueous solution of greasy sesame-send cake in the step 1, remove the carbohydrate and the protein of solubility, then in oven dry below 70 ℃ with distilled water or 3～10%;
(3) sesame-send cake that step 2 is dried adds methyl alcohol, ethanol, ethyl acetate or the acetone etc. of 2～10 times of volumes, and lixiviate is 1～3 time in 35～75 ℃ of hot water, and each 2～10 hours, solid-liquid separation;
(4) the filtrate rotary evaporation with step 3 is concentrated into the medicinal extract shape, removes solvent;
(5) with the small amount of thermal aqueous suspension of step 4 gained medicinal extract, use ethyl acetate extraction 1～3 time, gained extraction liquid rotary evaporation is concentrated obtain acetic acid ethyl ester extract;
(6) adopt sample on the wet method dress post dry method, take by weighing chromatography and be loaded in the silica gel column chromatography, get sample on an amount of acetic acid ethyl ester extract with 200～300 order silica gel;
(7) mixed solution that adopts petrol ether/ethyl acetate different volumes ratio by gradient 100/0,20/1,16/1,8/1,4/1,2/1,1/1,1/2,1/3,1/4 and 0/100 wash-out successively, promptly obtains sesamin as eluent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100198629A CN101007827A (en) | 2007-02-01 | 2007-02-01 | Method of extracting sesamin from seasame cake |
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| Application Number | Priority Date | Filing Date | Title |
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| CNA2007100198629A CN101007827A (en) | 2007-02-01 | 2007-02-01 | Method of extracting sesamin from seasame cake |
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| CN101007827A true CN101007827A (en) | 2007-08-01 |
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| CNA2007100198629A Pending CN101007827A (en) | 2007-02-01 | 2007-02-01 | Method of extracting sesamin from seasame cake |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101423860B (en) * | 2008-12-11 | 2011-07-06 | 江苏大学 | Gingeli antioxidation polypeptide composition and method for producing the same |
| CN102432619A (en) * | 2010-09-29 | 2012-05-02 | 苏州瑞蓝博中药技术开发有限公司 | Preparation method of sesamin |
| CN102793055A (en) * | 2011-12-22 | 2012-11-28 | 江南大学 | Method for degreasing and decoloring distillers dried grains with soluble (DDGS) |
| CN103160374A (en) * | 2013-03-28 | 2013-06-19 | 中南林业科技大学 | Method for preparing low denatured rice bran meal through extraction method |
| CN102781944B (en) * | 2009-10-27 | 2014-04-09 | 乔志亚生技股份有限公司 | Method for isolation and purification of sesamolin and sesamin from mixture of sesamolin and sesamin |
| CN104817566A (en) * | 2015-04-03 | 2015-08-05 | 安徽新桥工贸有限责任公司 | Sesamin separation extraction method |
| CN104910170A (en) * | 2009-07-03 | 2015-09-16 | 富味乡食品股份有限公司 | Method for preparing sesamin and sesamolin |
| CN105341136A (en) * | 2015-11-03 | 2016-02-24 | 安徽工程大学 | Natural oxidation inhibitor containing plant extracts, and preparation method and application of natural oxidation inhibitor, as well as processing method of minced pork |
| CN105505574A (en) * | 2015-12-04 | 2016-04-20 | 南京威尔化工有限公司 | Method for preparing high-purity ricinus oil according to chromatographic separation |
| CN106543196A (en) * | 2016-10-28 | 2017-03-29 | 浙江惠光生化有限公司 | A kind of method that sesamin is extracted from Oleum sesami |
| CN106565799A (en) * | 2016-10-19 | 2017-04-19 | 天津商业大学 | Method for supercritical carbon dioxide extraction of lignan from fermented sesame cakes |
| CN111004247A (en) * | 2019-12-01 | 2020-04-14 | 福建农林大学 | New plant source raw material for preparing 4-hydroxy sesamin and method thereof |
-
2007
- 2007-02-01 CN CNA2007100198629A patent/CN101007827A/en active Pending
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101423860B (en) * | 2008-12-11 | 2011-07-06 | 江苏大学 | Gingeli antioxidation polypeptide composition and method for producing the same |
| CN104910170A (en) * | 2009-07-03 | 2015-09-16 | 富味乡食品股份有限公司 | Method for preparing sesamin and sesamolin |
| CN102781944B (en) * | 2009-10-27 | 2014-04-09 | 乔志亚生技股份有限公司 | Method for isolation and purification of sesamolin and sesamin from mixture of sesamolin and sesamin |
| CN102432619A (en) * | 2010-09-29 | 2012-05-02 | 苏州瑞蓝博中药技术开发有限公司 | Preparation method of sesamin |
| CN102793055A (en) * | 2011-12-22 | 2012-11-28 | 江南大学 | Method for degreasing and decoloring distillers dried grains with soluble (DDGS) |
| CN103160374A (en) * | 2013-03-28 | 2013-06-19 | 中南林业科技大学 | Method for preparing low denatured rice bran meal through extraction method |
| CN104817566A (en) * | 2015-04-03 | 2015-08-05 | 安徽新桥工贸有限责任公司 | Sesamin separation extraction method |
| CN105341136A (en) * | 2015-11-03 | 2016-02-24 | 安徽工程大学 | Natural oxidation inhibitor containing plant extracts, and preparation method and application of natural oxidation inhibitor, as well as processing method of minced pork |
| CN105505574A (en) * | 2015-12-04 | 2016-04-20 | 南京威尔化工有限公司 | Method for preparing high-purity ricinus oil according to chromatographic separation |
| CN106565799A (en) * | 2016-10-19 | 2017-04-19 | 天津商业大学 | Method for supercritical carbon dioxide extraction of lignan from fermented sesame cakes |
| CN106565799B (en) * | 2016-10-19 | 2019-05-17 | 天津商业大学 | Lignan in supercritical carbon dioxide extracting fermented Semen Sesami grouts |
| CN106543196A (en) * | 2016-10-28 | 2017-03-29 | 浙江惠光生化有限公司 | A kind of method that sesamin is extracted from Oleum sesami |
| CN106543196B (en) * | 2016-10-28 | 2019-01-08 | 浙江惠光生化有限公司 | A method of extracting sesamin from sesame oil |
| CN111004247A (en) * | 2019-12-01 | 2020-04-14 | 福建农林大学 | New plant source raw material for preparing 4-hydroxy sesamin and method thereof |
| CN111004247B (en) * | 2019-12-01 | 2024-02-06 | 福建农林大学 | New plant source raw material for preparing 4-hydroxy sesamin and method thereof |
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