CN102643317A - Method for preparing sesaminol tri-glucoside - Google Patents
Method for preparing sesaminol tri-glucoside Download PDFInfo
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- CN102643317A CN102643317A CN2012101253499A CN201210125349A CN102643317A CN 102643317 A CN102643317 A CN 102643317A CN 2012101253499 A CN2012101253499 A CN 2012101253499A CN 201210125349 A CN201210125349 A CN 201210125349A CN 102643317 A CN102643317 A CN 102643317A
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Abstract
The invention provides a method for preparing sesaminol tri-glucoside, which mainly comprises the following steps: (1) raw material selection: taking sesame seed or sesame oil production byproduct namely sesame cake pulp as raw materials; (2) normal hexane degreasing; (3) ethanol aqueous extraction; (4) separation and purification: separating and purifying by adopting polyamide column chromatography, eluting with water and ethanol solution, detecting by HPLC (high performance liquid chromatography), concentrating under reduced pressure, and vacuum-drying to obtain sesaminol tri-glucoside with purity more than 80%; and (5) refining: further purifying by adopting HW40 column chromatography to obtain sesaminol tri-glucoside with purity more than 98%. Compared with the methods reported in the literature, the method has the advantages of inexpensive and easily available raw materials, simple and feasible process, recyclable solvent, low environmental pollution, low cost and the like, and is suitable for scaled production of high-purity sesaminol tri-glucoside.
Description
Technical field
What the present invention relates to is a kind of method of purification, the method for specifically a kind of extraction from til seed or sesame cake meal, separation and purifying sesamin phenol tri-glucose glycosides.
Background technology
Sesame is that China also is one of important in the world oil crops, receives China, Japan and and some Asian countries people's favor deeply as traditional heath food always.The sesame lignan is mainly given the credit in the performance of sesame functionally active.
The sesame lignan comprises fat-soluble lignan and water-soluble lignan.Fat-soluble lignan is present in the til, mainly comprises sesamin, sesamolin, sesamol and sesamin phenol etc., has anti-oxidant, protection liver, reduces plasma cholesterol, suppresses effects such as Δ 5 desaturases, anti-cancer and immuno-stimulating.Water-soluble lignan is formed by connecting through glycosidic link to termolecular glucose aglycon and, has better water solubility, mainly is present in the sesame cake meal after the degreasing.The water-soluble lignan of report mainly contains sesamin phenol glucoside, sesamolin phenol glucoside and rosin spirit glucoside at present, and wherein sesamin phenol tri-glucose glycosides content is the highest.Compare with fat-soluble lignan, the antioxidation activity in vitro of sesamin phenol tri-glucose glycosides a little less than, but in vivo under the effect of intestinal microflora and beta-glucosidase, sesamin phenol tri-glucose glycosides can be transformed into Mammals lignan Enterodiol and HPMF
[1], the effect of performance estrogen activity.In addition, sesamin phenol tri-glucose glycosides meta-bolites in vivo has very strong oxidation-resistance
[2]Thereby, different physiological roles such as performance anti-inflammatory, anti-cancer
[3-5]
The preparation method of relevant sesamin phenol tri-glucose, report mainly is to adopt methyl alcohol or alcoholic acid extraction with aqueous solution at present, macroporous resin adsorption-water/methanol-eluted fractions, preparation or half preparative hplc are refining to form
[1,6,7]Therefore its preparation process not only need consume a large amount of harmful organic solvent, and receives the restriction of production unit, still fails to be applied to large-scale production at present.
[1]Jan?Kuo-Ching，Hwang?Lucy?Sun，Ho?Chi-Tang.Biotransformation?of?sesaminol?triglucoside?to?mammalian?lignans?by?intestinal?microbiota[J].Journal?of?Agricultural?and?Food?Chemistry，2009，57：6101-6106.
[2]Jan?Kuo-Ching，Hwang?Lucy?Sun，Ho?Chi-Tang.Tissue?distribution?and?elimination?of?sesaminol?triglucoside?and?its?metabolites?in?rat[J].Molecular?Nutrition?and?Food?Research.2009，53：815-825.
[3]Sheng?HongQiang，Hirose?Yoshinobu，Hata?Kazuya，et?al.Modifying?effect?of?dietary?sesaminol?glucosides?on?the?formation?of?azoxymethane-induced?premalignant?lesions?of?rat?colon[J].Cancer?Letters，2007，246：63-68.
[4]Lee?Sun?Young，Ha?Tae?Youl，Son?Dong?Ju，et?al.Effect?of?sesaminol?glucosides?onβ-amyloid-induced?PC12?cell?death?through?antioxidant?mechanisms[J].Neuroscience?Research，2005，52(4)：330-341.
[5]Jan?Kuo-Ching，Ku?Kuo-Lung，Chu?Yan-Hwa，et?al.Tissue?distribution?and?elimination?of?estrogenic?and?anti-inflammatory?catechol?metabolites?from?sesaminol?triglucoside?in?rats[J].Journal?of?Agricultural?and?Food?Chemistry，2010，58：7693-7700.
[6] Korunamu KK, Takemoto Oil & Fat Co LTD.Production of sesaminol triglucoside: Japan, JP10287695A [P] .1998-10-27.
[7]Hirotaka?Katsuzaki，Shunro?Kawakishi，Toshihiko?Osawa.Sesaminol?glucosides?in?sesame?seeds[J].Phytochemistry，1994，35(3)：773-776.
Summary of the invention
The purpose of this invention is to provide a kind of be suitable for suitability for industrialized production produce by product from til seed or til---prepare the method for high purity sesamin phenol tri-glucose glycosides the sesame cake meal.
The objective of the invention is to realize through following steps:
(1) material choice: by product---sesame cake meal all can be used as raw material for the til seed of roasting stir-fry/roasting stir-fry or til production.
(2) degreasing: after raw material pulverizing, add the abundant degreasing of normal hexane, supernatant is removed in centrifugal or filtration, and the deposition part is subsequent use after seasoning or warm air drying.
(3) extract: with til seed after the degreasing or sesame cake meal is raw material, adopts aqueous ethanolic solution to extract sesamin phenol tri-glucose glycosides, and extracting solution removes through concentrating under reduced pressure and desolvates, and can obtain sesamin phenol tri-glucose glycosides crude extract.
(4) separation and purification: go up polyamide column after sesamin phenol tri-glucose glycosides crude extract is dissolved in water; Water and ethanolic soln carry out stepwise elution respectively; The HPLC method detects; Collect water elution component (being rich in sesamin phenol tri-glucose glycosides), obtaining purity through concentrating under reduced pressure, drying in vacuum is the sesamin phenol tri-glucose glycosides more than 80%.
(5) refining: the sesamin phenol tri-glucose glycosides bullion with step (4) is obtained, carry out purifying through HW40 resin column chromatography, can obtain purity is the sesamin phenol tri-glucose glycosides more than 98%.
Wherein, normal hexane described in the step (2) is 5～30mL/g with the liquid material ratio of sesame raw material, degreasing 1～5 time, each 5～24h.
Aqueous ethanolic solution described in the step (3) is concentration 50～95% ethanolic solns, and liquid material ratio is 5～30mL/g, and extraction time is 1～5 time, each 5～24h.
Degreasing of the present invention and extraction conditions are relatively gentleer, can or not be higher than under 60 ℃ of conditions in room temperature to carry out; In degreasing and leaching process, can adopt intermittently stirring or continuously stirring to make the feed liquid thorough mixing, to improve rate of mass transfer, shorten extraction time.
Concentrating under reduced pressure condition of the present invention is pressure 0.07～0.1Mpa, and temperature is room temperature or is no more than 50 ℃.
Separation and purification of the present invention is to adopt the polyamide column chromatography method; Wet method dress post; Go up appearance behind zero(ppm) water (0.45 μ m water system membrane filtration) 3～10 times of column volumes of balance, at first use 1～15 times of column volume of water elution, HPLC detects sesamin phenol tri-glucose glycosides content and purity in the elutriant; And collect corresponding water elution component, vacuum concentration and drying in vacuum obtain the sesamin phenol tri-glucose glycosides of purity more than 80%; Secondly, adopt 1～15 times of column volume of ethanol elution, remove pigment and other weakly polar component of polyamide column absorption, final rinse water is to there not being the ethanol flavor, in order to the separation and purification of next sample.
Process for purification of the present invention is to adopt HW 40 resin column chromatographies; Wet method dress post, water (0.45 μ m water system membrane filtration) balance 6～24h is after the last appearance; With 1～15 times of cylinder ponding of 0.1～5.0mL/min flow velocity wash-out; Automatic collector is collected elutriant, and HPLC method detection level and purity are the sesamin phenol tri-glucose glycosides more than 98% through vacuum concentration and drying in vacuum acquisition purity.
The product of the present invention's preparation, electrospray ionization mass spectrum is the result show, [M-H] of m/z 854.77 and sesamin phenol tri-glucose glycosides
-The peak coincide, and this product removes one or two or three glucosides, and the fragment ion of generation is respectively m/z 178.83 [Glu-H]
-, 322.80 [2Glu-H
2O-H]
-With 368.75 [M-3Glu+3H
2O-H]
-, m/z 891.13 possibly be fragmention [M+2H
2O-H]
-Infer that thus the product relative molecular mass is 855.77; With document (Ali A.Moazzami, Rolf E.Andersson, Afaf Kamal-Eldin.HPLC analysis of sesaminol glucosides in sesame seeds [J] .Journal of Agricultural and Food Chemistry; 2006,54:633-638; Jan Kuo-Ching; Hwang Lucy Sun; Ho Chi-Tang.Tissue distribution and elimination of sesaminol triglucoside and its metabolites in rat [J] .Molecular Nutrition and Food Research.2009; 53:815-825) molecular weight 856 of the sesamin phenol tri-glucose glycosides of report conforms to, and confirms that therefore the product of preparation is a sesamin phenol tri-glucose glycosides.
China's sesame output is abundant, but major part is used to produce til, by product---the sesame cake meal behind the system oil, and only as feed and fertilizer, its resource does not obtain development and utilization.Sesamin phenol tri-glucose glycosides is present in the sesame cake meal after the degreasing in a large number; The present invention is with til seed or to make oily by product sesame cake meal be raw material; Adopt alcohol solution extraction, polymeric amide and HW 40 column chromatographies to prepare highly purified sesamin phenol tri-glucose glycosides, have important practical significance for the development and utilization of sesame resource.
The method for preparing sesamin phenol tri-glucose glycosides of the present invention, raw materials used cheap and easy to get, simple for process, environmentally friendly, cost is low, and sesamin phenol tri-glucose glycosides purity high (HPLC purity >=98%) has higher actual application value.
Description of drawings
Fig. 1 is the structural formula of sesamin phenol tri-glucose glycosides;
Fig. 2 is atmosphere spraying mass spectrum (negative ion mode) figure of sesamin phenol tri-glucose glycosides;
Fig. 3 is the infrared spectrogram of sesamin phenol tri-glucose glycosides;
Fig. 4 is the HPLC figure of sesamin phenol tri-glucose glycosides and at 200～400nm scintigram.
Embodiment
Following examples are used to explain the present invention, but are not used for limiting scope of the present invention.
Take by weighing dried white sesame seed 1.00kg, pulverize, add the 10L normal hexane, room temperature degreasing 6h (stirring once in per 2 hours), degreasing 3 times.Sesame seed meal after the degreasing (about 0.63kg) adds 6L 60% ethanolic soln, and room temperature is extracted 6h (stirring once in per 2 hours), extracts 3 times.United extraction liquid through concentrating under reduced pressure, vacuum lyophilization, obtains containing the extract (about 17.45g) of sesamin phenol tri-glucose glycosides.Extract is dissolved with suitable quantity of water, carry out polyamide column chromatography (3.0 * 60cm).Polyamide column is earlier with going up appearance after the 5BV zero(ppm) water balance again; Wash (5BV) ethanol elution (10BV) again during wash-out earlier, automatic collector is collected the water elution component, and every 10mL collects 1 pipe; The HPLC method detects the content of the sesamin phenol tri-glucose glycosides in the collection tube; Merge elution fraction, and concentrating under reduced pressure, vacuum lyophilization, promptly obtain purity and be 84.17% sesamin phenol tri-glucose glycosides bullion (about 812mg); Bullion is dissolved in an amount of zero(ppm) water, after HW 40 chromatography columns, zero(ppm) water wash-out 6BV; Automatic collector is collected elution fraction, and the HPLC method detects and merges collects liquid, through concentrating under reduced pressure; Vacuum lyophilization promptly obtains purity and is 98.32% sesamin phenol tri-glucose glycosides (about 677mg).Reach through HPLC, UV-vis, ESI-MS, IR
1H-NMR characterizes, the reference report, and the product of conclusive evidence the present invention preparation is a sesamin phenol tri-glucose glycosides.
Embodiment 2
Take by weighing dried Semen Sesami Nigrum seed 1.00kg, pulverize, add the 15L normal hexane, room temperature degreasing 8h, degreasing 4 times.Sesame seed meal after the degreasing (about 0.65kg) adds 10L 75% ethanolic soln, and room temperature is extracted 6h, extracts 4 times.United extraction liquid promptly obtains containing the extract (about 17.88g) of sesamin phenol tri-glucose glycosides after concentrating under reduced pressure, vacuum lyophilization.Extract is dissolved with suitable quantity of water, carry out polyamide column chromatography (3.0 * 60cm).Polyamide column is earlier with going up appearance after the 5BV zero(ppm) water balance again; Wash (10BV) ethanol elution (10BV) again during wash-out earlier; Automatic collector is collected the water elution component, and every 10mL collects 1 pipe, and the HPLC method detects the content of the sesamin phenol tri-glucose glycosides in the collection tube; Merge to collect component and concentrating under reduced pressure, it is 86.04% sesamin phenol tri-glucose glycosides bullion (about 807mg) that vacuum lyophilization promptly obtains purity; Bullion is dissolved in an amount of zero(ppm) water, after HW 40 chromatography columns, zero(ppm) water wash-out 6BV; Automatic collector is collected elution fraction, and the HPLC method detects and merges collects liquid, through concentrating under reduced pressure; Vacuum lyophilization promptly obtains purity and is 99.38% sesamin phenol tri-glucose glycosides (about 643mg).
Embodiment 3
Take by weighing til seed 1.00kg, pulverize, add the 25L normal hexane, 50 ℃ of heating in water bath stir degreasing 5h, degreasing 3 times.Sesame seed meal after the degreasing (about 617g) adds 15L 90% ethanolic soln, and 50 ℃ of heating in water bath stir and extract 5h, extract 3 times.United extraction liquid promptly obtains containing the extract (about 17.23g) of sesamin phenol tri-glucose glycosides after concentrating under reduced pressure, vacuum lyophilization.Extract is dissolved with suitable quantity of water, carry out polyamide column chromatography (3.0 * 60cm).Polyamide column is earlier with going up appearance after the 10BV zero(ppm) water balance again; Wash (15BV) ethanol elution (12BV) again during wash-out earlier; Automatic collector is collected the water elution component, and every 10mL collects 1 pipe, and the HPLC method detects the content of the sesamin phenol tri-glucose glycosides in the collection tube; Merge elution fraction and concentrating under reduced pressure, it is 87.15% sesamin phenol tri-glucose glycosides bullion (about 836mg) that vacuum lyophilization promptly obtains purity; Bullion is dissolved in an amount of zero(ppm) water, after HW 40 chromatography columns, zero(ppm) water wash-out 10BV; Automatic collector is collected elution fraction, and the HPLC method detects and merges collects liquid, through concentrating under reduced pressure; Vacuum lyophilization promptly obtains purity and is 99.86% sesamin phenol tri-glucose glycosides (about 639mg).
Embodiment 4
Take by weighing the oily by product sesame cake meal 1.00kg of system, add the 15L normal hexane, stirring at room degreasing 16h, degreasing 3 times.Sesame seed meal after the degreasing (about 885g) adds 10L 70% aqueous ethanolic solution, and stirring at room is extracted 16h, extracts 3 times.United extraction liquid promptly obtains containing the extract (about 24.25g) of sesamin phenol tri-glucose glycosides after concentrating under reduced pressure, vacuum lyophilization.Extract is dissolved with suitable quantity of water, carry out polyamide column chromatography (3.0 * 60cm).Polyamide column is earlier with going up appearance after the 10BV zero(ppm) water balance again; Wash (12BV) ethanol elution (15BV) again during wash-out earlier; Automatic collector is collected the water elution component, and every 10mL collects 1 pipe, and the HPLC method detects the content of the sesamin phenol tri-glucose glycosides in the collection tube; Merge elution fraction and concentrating under reduced pressure, it is 87.66% sesamin phenol tri-glucose glycosides bullion (about 1083mg) that vacuum lyophilization promptly obtains purity; Bullion is dissolved in an amount of zero(ppm) water, after HW 40 chromatography columns, zero(ppm) water wash-out 15BV; Automatic collector is collected elution fraction, and the HPLC method detects and merges collects liquid, through concentrating under reduced pressure; Vacuum lyophilization promptly obtains purity and is 99.88% sesamin phenol tri-glucose glycosides (about 916mg).
Take by weighing sesame cake meal 100g, add the 2.0L normal hexane, 35 ℃ of heating in water bath stir degreasing 10h, degreasing 3 times.Sesame seed meal after the degreasing (about 82g) adds 10L 60% aqueous ethanolic solution, and 30 ℃ of heating in water bath stir and extract 6h, extract 3 times.United extraction liquid promptly obtains containing the extract (about 2.57g) of sesamin phenol tri-glucose glycosides after concentrating under reduced pressure, vacuum lyophilization.Extract is dissolved with suitable quantity of water, carry out polyamide column chromatography (3.0 * 60cm).Polyamide column is earlier with going up appearance after the 10BV zero(ppm) water balance again; Wash (10BV) ethanol elution (12BV) again during wash-out earlier; Automatic collector is collected the water elution component, and every 10mL collects 1 pipe, and the HPLC method detects the content of the sesamin phenol tri-glucose glycosides in the collection tube; Merge elution fraction and concentrating under reduced pressure, it is 87.02% sesamin phenol tri-glucose glycosides bullion (about 97.33mg) that vacuum lyophilization promptly obtains purity; Bullion is dissolved in an amount of zero(ppm) water, after HW 40 chromatography columns, zero(ppm) water wash-out 12BV; Automatic collector is collected elution fraction, and the HPLC method detects and merges collects liquid, through concentrating under reduced pressure; Vacuum lyophilization promptly obtains purity and is 98.59% sesamin phenol tri-glucose glycosides (about 83.14mg).
Though, the present invention has been done detailed description in the preceding text with general explanation and practical implementation instance, on basis of the present invention, can do some modifications or improvement to it.Therefore, these modifications or the improvement on the basis of not departing from spirit of the present invention, made all belong to the scope that requirement of the present invention is protected.
Claims (8)
1. a method for preparing sesamin phenol tri-glucose glycosides is characterized in that, comprises the steps:
1.1 material choice: by product---sesame cake meal all can be used as raw material for the til seed of roasting stir-fry/roasting stir-fry or til production;
1.2 degreasing: after raw material pulverizing, add the abundant degreasing of normal hexane, supernatant is removed in centrifugal or filtration, and the deposition part is subsequent use after warm air drying or seasoning;
1.3 extract: with til seed after the degreasing or sesame cake meal is raw material, adopts aqueous ethanolic solution to extract sesamin phenol tri-glucose glycosides, extracting solution removes through concentrating under reduced pressure and desolvates, and can obtain sesamin phenol tri-glucose glycosides crude extract;
1.4 separation and purification: adopt polyamide column chromatography that step 1.3 gained crude extract is carried out the initial gross separation purifying; Water and ethanolic soln carry out stepwise elution respectively; The HPLC method detects; Collect water elution component (being rich in sesamin phenol tri-glucose glycosides), obtaining purity through concentrating under reduced pressure, drying in vacuum is the sesamin phenol tri-glucose glycosides more than 80%;
1.5 refining: with the sesamin phenol tri-glucose glycoside product of step 1.4 gained, adopt HW 40 resin column chromatographies to be further purified, can obtain purity is the sesamin phenol tri-glucose glycosides more than 98%.
2. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1 is characterized in that, raw material described in the step 1.1 is that til seed or til are produced by product---sesame cake meal.
3. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1 is characterized in that degreasing solvent described in the step 1.2 is a normal hexane, and normal hexane is 5～30mL/g with the liquid material ratio of sesame raw material, degreasing 1～5 time, each 5～24h.
4. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1 is characterized in that, aqueous ethanolic solution described in the step 1.3 is concentration 50～95% aqueous ethanolic solutions, and liquid material ratio is 5～30mL/g, and extraction time is 1～5 time, each 5～24h.
5. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1 is characterized in that, the pressure when concentrating under reduced pressure described in the step 1.3 and 1.4 removes and to desolvate is 0.07～0.1Mpa, and temperature is room temperature or the highlyest is no more than 50 ℃.
6. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1; It is characterized in that; Temperature is 20～60 ℃ in til seed or sesame cake meal degreasing and leaching process, adopts continuously stirring or intermittently stirs (per 0.5～6h stirs once) so that liquid material thorough mixing.
7. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1 is characterized in that, described in the step 1.4, the crude extract of step 1.3 gained is dissolved in suitable quantity of water after, adopt polyamide column chromatography initial gross separation purifying.At first use 1～15 times of column volume of water elution, HPLC detects sesamin phenol tri-glucose glycosides content and purity in the elutriant, and collects corresponding elution fraction, can obtain the sesamin phenol tri-glucose glycosides of purity more than 80% behind the concentrate drying.Secondly, adopt 1～15 times of column volume of ethanol elution, remove pigment and other weakly polar component of polyamide column absorption, final rinse water is to there not being the ethanol flavor, in order to the separation and purification of next sample.
8. a kind of method for preparing sesamin phenol tri-glucose glycosides as claimed in claim 1 is characterized in that, step 1.5 process for purification is HW 40 resin column chromatographies; Wet method dress post, water balance 6～24h is after the last appearance; With 1～15 times of cylinder ponding of 0.1～5.0mL/min flow velocity wash-out; Automatic collector is collected elutriant, and HPLC method detection level and purity are the sesamin phenol tri-glucose glycosides more than 98% through obtaining purity behind the concentrate drying.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590880A (en) * | 2019-09-23 | 2019-12-20 | 河南省农业科学院 | Method for separating and purifying sesaminol triglycoside |
| CN114190077A (en) * | 2020-06-25 | 2022-03-15 | 株式会社皇后篮 | Preparation method of sesame seed meal extract and food composition containing same as active ingredient for preventing or improving colitis |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590880A (en) * | 2019-09-23 | 2019-12-20 | 河南省农业科学院 | Method for separating and purifying sesaminol triglycoside |
| CN110590880B (en) * | 2019-09-23 | 2022-10-11 | 河南省农业科学院 | Method for separating and purifying sesaminol triglucoside |
| CN114190077A (en) * | 2020-06-25 | 2022-03-15 | 株式会社皇后篮 | Preparation method of sesame seed meal extract and food composition containing same as active ingredient for preventing or improving colitis |
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Application publication date: 20120822 |