CN101775050A - Alpha-glucose-based new hesperidin dihydrochalcone as well as preparation method and application thereof - Google Patents
Alpha-glucose-based new hesperidin dihydrochalcone as well as preparation method and application thereof Download PDFInfo
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- CN101775050A CN101775050A CN201010019204A CN201010019204A CN101775050A CN 101775050 A CN101775050 A CN 101775050A CN 201010019204 A CN201010019204 A CN 201010019204A CN 201010019204 A CN201010019204 A CN 201010019204A CN 101775050 A CN101775050 A CN 101775050A
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Abstract
The invention discloses alpha-glucose-based new hesperidin dihydrochalcone. The compound is obtained by carrying out alpha-glucose-based reaction by using new hesperidin dihydrochalcone and dextrin as raw materials under the catalysis of glucosyltransferase. The alpha-glucose-based new hesperidin dihydrochalcone synthesized by the method can be widely used for the industries of foodstuff, medicaments, forages, daily chemicals and the like as a sweetener, a flavoring agent, a flavor enhancer and the like.
Description
Technical field
The invention belongs to and relate to a kind of foodstuff additive and its production and use, be specifically related to alpha-glucose-based neohesperidin dihydrochalcone and its production and use.
Background technology
The food intensive sweetener is meant that sugariness is the sweeting agent of sucrose more than tens times, divides natural and chemosynthesis two big classes.Natural intensive sweetener is because its security is good, and the human consumer easily accepts, and enjoys the welcome in market.Present natural intensive sweetener mainly contains stevioside, glycyrrhizin, Momordia grosvenori aglycone, dihydrochalcone and Suo Matian etc.
Dihydrochalcone is to separate the compound with sweet taste that obtains from oranges and tangerines, naringin at first.People have synthesized the derivative of a large amount of such sweeting agents, and wherein some has just structurally done slightly little change, and some has then done bigger change.All these all are the relations of understanding its structure and local flavor for further, or in order to improve the quality and solubleness and reduction toxicity etc.
The basic skeleton structure of neohesperidin dihydrochalcone is 1, the 3-diphenyl acetone, and its structure is shown below:
The sugariness of neohesperidin dihydrochalcone is 1800 times of sucrose, and the solubleness in water only is 0.5g/L.At present, neohesperidin dihydrochalcone is used as spices or sweeting agent by a plurality of state approvals.But, limited its widespread use to a certain extent because this sweeting agent has shortcomings such as bad back bitter taste, the solubleness in water of similar Radix Glycyrrhizae are little.
Desire is improved the sweet taste characteristic of neohesperidin dihydrochalcone, and method has two kinds at present: a kind of is and the composite use of other sweeting agents to reduce the usage quantity of neohesperidin dihydrochalcone.This is the main using method of present neohesperidin dihydrochalcone in industries such as food, medical daily use chemicals, feeds, and this just causes the neohesperidin dihydrochalcone usage quantity to have only tens to the hundreds of ton at a whole world year consumption.Another kind method is to add other taste corrigents, as Sunmorl N 60S, Gluconolactone, sal epsom etc.This taste antidote, because it is its effect is limited, actual in industrial employing and few.
Summary of the invention
The object of the present invention is to provide a kind of alpha-glucose-based neohesperidin dihydrochalcone, this compound can be used as sweeting agent, sweetener, correctives, is used for products such as food, medicine, feed, daily use chemicals product.
Another object of the present invention is to provide the preparation method of alpha-glucose-based neohesperidin dihydrochalcone, this preparation method's route is simple, reaction conditions is gentle, productive rate is high.
The present invention also aims to provide the purposes of alpha-glucose-based neohesperidin dihydrochalcone.
Alpha-glucose-based neohesperidin dihydrochalcone provided by the invention, its chemical structural formula is:
In the following formula, n represents glucosyl group number, n=1-7.
The preparation method of alpha-glucose-based neohesperidin dihydrochalcone provided by the invention, be to be raw material with neohesperidin dihydrochalcone and dextrin, the alpha-glucosyl reaction takes place under the glucanotransferase effect, generates alpha-glucose-based neohesperidin dihydrochalcone.
Among the preparation method of the present invention, described glucanotransferase can be the table sugar based transferase, and preferred cyclodextrin glucanotransferase, this kind of enzyme can be from bacstearothermophiluses, have a liking for to separate the microorganisms such as alkali fat genus bacillus, bacillus macerans and obtain.
Among the preparation method of the present invention, described dextrin can be commercially available finished product dextrin, also can be to be that raw material is handled the thick dextrin that obtains through enzyme with starch, the commercially available finished product dextrin of preferred DE value 4-20.
Among the preparation method of the present invention, described enzymatic conversion reaction is to carry out in containing the alcoholic acid aqueous solution, and wherein the ethanol weight content is 0-40%, preferred 10-20%; PH is 5-10, preferred pH6-9; Temperature of reaction is 0-70 ℃, preferred 50-60 ℃; Reaction times is 0.5-100 hour, preferred 10-50 hour.
Among the preparation method of the present invention, after described enzymatic conversion reaction finishes, adopt macroporous adsorbent resin, decolouring, the crystallization method alpha-glucose-based neohesperidin dihydrochalcone of further purifying.
The present invention is dissolved in neohesperidin dihydrochalcone in the aqueous ethanolic solution of 0-40%, preferred 10-20%.Alcohol concn is too low, and neohesperidin dihydrochalcone solubleness is low, and is unactual in the production; Alcohol concn is too high, as surpassing 40%, the easy inactivation of glucanotransferase.Through overtesting, find that the alcohol concn of 10-20% is the most suitable.If reaction solution does not use ethanol, can adopt and in the aqueous solution, add sodium hydroxide, potassium hydroxide etc., pH value of solution is transferred to 8.5-10, neohesperidin dihydrochalcone just can be dissolved in the water like this, keeps this pH value, and conversion reaction also can be finished smoothly.It can be 0-70 ℃ that conversion reaction requires temperature, and preferred 50-60 ℃, because the enzyme of glucanotransferase is lived the highlyest under this temperature, the reaction times needs several hours usually to hundreds of hour, follows the tracks of the degree that reacts completely with paper chromatography.
Glucanotransferase is a kind of polyose synthetic enzyme with catalysis, mainly from bacstearothermophilus, have a liking for to separate the microorganisms such as alkali fat genus bacillus, bacillus macerans and obtain.This transferring enzyme can make many flavonoid glycoside connect and go up a plurality of glucosyl groups.
After the neohesperidin dihydrochalcone conversion reaction becomes alpha-glucose-based neohesperidin dihydrochalcone, can directly be used as sweeting agent, correctives and sweetener, be used for industries such as food, medicine, feed, daily use chemicals, also can further purify.Method of purification can be recrystallization, column chromatography, macroporous adsorbent resin etc., preferred macroporous adsorbent resin method, water soluble components such as inorganic salt, sugar are removed in elder generation's water flushing, flush out product with ethanol/water mixed solvent again, generally can go out target product with 30-50% ethanol.Product obtains the alpha-glucose-based neohesperidin dihydrochalcone of white powder through technologies such as concentrated, decolouring, crystallizations.
The enzymatic conversion product adopts HPLC-ESI/Mass to identify the molecular structure of product after above-mentioned purifying technique is purified.The HPLC testing conditions is as follows:
Post: C18 post (250mm, 4.6mm, 5 μ m)
Moving phase: V (methyl alcohol): V (water)=60: 40
Flow velocity: 1.0mL/min
Detect wavelength: 286nm
Column temperature: 25 ℃
Sample size: 10 μ l
HPLC spectrogram and ESI-Mass molecular ion peak (table 1) by analysis illustrate that the structure of the alpha-glucose-based neohesperidin dihydrochalcone of target product is as shown below:
Table 1 ESI-Mass molecular ion peak is analyzed
| Molecular ion peak | ??600 | ??762 | ??924 | ??1086 | ??1248 | ??1410 | ??1572 | ??1734 |
| Release the numerical value of n | ??0 | ??1 | ??2 | ??3 | ??4 | ??5 | ??6 | ??7 |
The present invention is surprised to find the alpha-glucose-based neohesperidin dihydrochalcone sweet taste that is synthesized and is about about 1500 times of sucrose, the situation that the such sugariness multiple of alpha-glucose-based stevioside sharply descends do not occur.The sweet taste quality compare with neohesperidin dihydrochalcone also be improved significantly, particularly it covers that some bad tastes have better effect than neohesperidin dihydrochalcone in the food.The present invention finds alpha-glucose-based neohesperidin dihydrochalcone simultaneously, and at room temperature solubleness is up to 134.0g/L, and higher 268 times than neohesperidin dihydrochalcone (0.5g/L), this has just widened its use range greatly.The alpha-glucose-based neohesperidin dihydrochalcone that the present invention is synthesized can be widely used in industries such as food, medicine, feed, daily use chemicals, as sweeting agent, correctives, sweetener etc.
Embodiment
Embodiment 1
The neohesperidin dihydrochalcone of 1 part of quality and the cyclodextrin of 4 parts of quality (DE 8) joined in 20 part 20% the ethanolic soln, add cyclomaltodextrin glucanotransferase enzyme liquid then, regulate about pH value to 6.0,60 ℃ of reaction 48h down.Paper chromatographic analysis shows that neohesperidin dihydrochalcone partly is transformed into alpha-glucose-based neohesperidin dihydrochalcone.Reaction is heated to 80 ℃ with reaction mixture and makes enzyme deactivation after finishing, and is spin-dried for solvent then and adds 50ml distilled water again, places the after-filtration that spends the night and gets supernatant liquid.Clear liquid is crossed the HP-20 macroporous resin column, remove desaccharification and inorganic salt and other material with distillation washing post, wash post with 40% ethanolic soln again, concentrated being spin-dried for obtains product, promptly alpha-glucose-based neohesperidin dihydrochalcone.
Embodiment 2
The neohesperidin dihydrochalcone of 1 part of quality and the cyclodextrin of 7 parts of quality (DE 15) joined in 15 part 30% the ethanolic soln, add cyclomaltodextrin glucanotransferase enzyme liquid then, regulate about pH value to 6.0,60 ℃ of reaction 48h down.Paper chromatographic analysis shows that neohesperidin dihydrochalcone partly is transformed into alpha-glucose-based neohesperidin dihydrochalcone.Reaction is heated to 80 ℃ with reaction mixture and makes enzyme deactivation after finishing, and is spin-dried for solvent then and adds 50ml distilled water again, places the after-filtration that spends the night and gets supernatant liquid.Clear liquid is crossed the HP-20 macroporous resin column, remove desaccharification and inorganic salt and other material with distillation washing post, wash post with 30% ethanolic soln again, concentrated being spin-dried for obtains product, promptly alpha-glucose-based neohesperidin dihydrochalcone.
Embodiment 3
The neohesperidin dihydrochalcone of 1 part of quality and the cyclodextrin of 8 parts of quality (DE 6) joined in 20 parts the water, regulate about pH value to 9.8 and make its dissolving, add cyclomaltodextrin glucanotransferase enzyme liquid then, at 65 ℃ of reaction 50h down.Paper chromatographic analysis shows that neohesperidin dihydrochalcone partly is transformed into alpha-glucose-based neohesperidin dihydrochalcone.Reaction is heated to 80 ℃ with reaction mixture and makes enzyme deactivation after finishing, and cooling back regulator solution is placed the after-filtration that spends the night and got supernatant liquid to neutral.Clear liquid is crossed the HP-20 macroporous resin column, remove desaccharification and inorganic salt and other material with distillation washing post, wash post with 40% ethanolic soln again, concentrated being spin-dried for obtains product, promptly alpha-glucose-based neohesperidin dihydrochalcone.
Embodiment 4
The neohesperidin dihydrochalcone of 1 part of quality and the cyclodextrin of 10 parts of quality (DE 12) joined in 20 parts the water, regulate about pH value to 9.0 and make its dissolving, add cyclomaltodextrin glucanotransferase enzyme liquid then, at 60 ℃ of reaction 60h down.Paper chromatographic analysis shows that neohesperidin dihydrochalcone partly is transformed into alpha-glucose-based neohesperidin dihydrochalcone.Reaction is heated to 80 ℃ with reaction mixture and makes enzyme deactivation after finishing, and cooling back regulator solution is placed the after-filtration that spends the night and got supernatant liquid to neutral.Clear liquid is crossed the HP-20 macroporous resin column, remove desaccharification and inorganic salt and other material with distillation washing post, wash post with 40% ethanolic soln again, concentrated being spin-dried for obtains product, promptly alpha-glucose-based neohesperidin dihydrochalcone.
Application Example 1
A kind of fruit-flavored beverage that contains alpha-glucose-based neohesperidin dihydrochalcone, its prescription is:
Sucrose: 8%
Alpha-glucose-based neohesperidin dihydrochalcone: 0.0023%
Trisodium Citrate: 0.07%
Essence and flavoring agent: 0.1%
Food dye: an amount of
Add water: quantitatively
Application Example 2
A kind of peppermint chewing gum that contains alpha-glucose-based neohesperidin dihydrochalcone, its prescription is:
Sorbitol powder: 54.4%
Chewing gum base: 24.5%
Sorbitol Solution USP (70%): 15.0%
Glycerine: 4.8%
Essence: an amount of
Alpha-glucose-based neohesperidin dihydrochalcone: 0.017%
Claims (8)
1. alpha-glucose-based neohesperidin dihydrochalcone is characterized in that the chemical structural formula of this compound is:
In the following formula, n represents glucosyl group number, n=1-7.
2. the preparation method of the described alpha-glucose-based neohesperidin dihydrochalcone of claim 1, it is characterized in that: with neohesperidin dihydrochalcone and dextrin is raw material, the alpha-glucosyl reaction takes place under the glucanotransferase effect, generates alpha-glucose-based neohesperidin dihydrochalcone.
3. the preparation method of alpha-glucose-based neohesperidin dihydrochalcone according to claim 2, it is characterized in that: described glucanotransferase is a cyclomaltodextrin glucanotransferase, this kind of enzyme from bacstearothermophilus, have a liking for to separate alkali fat genus bacillus, the bacillus macerans microorganism and obtain.
4. the preparation method of alpha-glucose-based neohesperidin dihydrochalcone according to claim 2 is characterized in that: described dextrin is commercially available finished product dextrin or is that raw material is handled the thick dextrin that obtains through enzyme with starch.
5. the preparation method of alpha-glucose-based neohesperidin dihydrochalcone according to claim 2, it is characterized in that: described enzymatic conversion reaction is to carry out in containing the alcoholic acid aqueous solution, wherein the ethanol weight content is 0-40%; PH is 5-10; Temperature of reaction is 0-70 ℃; Reaction times is 0.5-100 hour.
6. the preparation method of alpha-glucose-based neohesperidin dihydrochalcone according to claim 5, it is characterized in that: described enzymatic conversion reaction is to carry out in containing the alcoholic acid aqueous solution, wherein the ethanol weight content is 10-20%; PH is 6-9; Temperature of reaction is 50-60 ℃; Reaction times is 10-50 hour.
7. the preparation method of alpha-glucose-based neohesperidin dihydrochalcone according to claim 2, it is characterized in that: after described enzymatic conversion reaction finishes, adopt macroporous adsorbent resin, decolouring, the crystallization method alpha-glucose-based neohesperidin dihydrochalcone of further purifying.
8. the described alpha-glucose-based neohesperidin dihydrochalcone of claim 1 is as the application of sweeting agent, correctives and sweetener.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880896A (en) * | 2014-01-21 | 2014-06-25 | 东莞广州中医药大学中医药数理工程研究院 | New dihydrogen chalcone glycosides compound separated from lithocarpus polystachyus and preparation method thereof |
| CN104664086A (en) * | 2015-03-31 | 2015-06-03 | 江西中成人药业有限公司 | Functional composite plant polysaccharide additive premixed feed |
| CN106543243A (en) * | 2016-11-08 | 2017-03-29 | 山东大学 | A kind of rhodioside derivative and preparation method thereof |
| CN111356376A (en) * | 2017-07-27 | 2020-06-30 | 健康科技生物活性剂有限公司 | Sweetening taste-masking composition, sweetening taste-masking product and use thereof |
| WO2021147575A1 (en) * | 2020-01-20 | 2021-07-29 | 中国科学院分子植物科学卓越创新中心 | New carbon glycoside glycosyltransferase and use thereof |
| CN115024458A (en) * | 2022-06-14 | 2022-09-09 | 上海龙殷生物科技有限公司 | A method for improving taste and bitter taste of extract of plant of Rutaceae and Citrus |
-
2010
- 2010-01-04 CN CN201010019204A patent/CN101775050A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880896A (en) * | 2014-01-21 | 2014-06-25 | 东莞广州中医药大学中医药数理工程研究院 | New dihydrogen chalcone glycosides compound separated from lithocarpus polystachyus and preparation method thereof |
| CN103880896B (en) * | 2014-01-21 | 2016-08-17 | 东莞广州中医药大学中医药数理工程研究院 | Lithocarpus polystachyus (wall) Rehd separates novel dihydrochalcone glycosides compound and preparation method thereof |
| CN104664086A (en) * | 2015-03-31 | 2015-06-03 | 江西中成人药业有限公司 | Functional composite plant polysaccharide additive premixed feed |
| CN106543243A (en) * | 2016-11-08 | 2017-03-29 | 山东大学 | A kind of rhodioside derivative and preparation method thereof |
| CN111356376A (en) * | 2017-07-27 | 2020-06-30 | 健康科技生物活性剂有限公司 | Sweetening taste-masking composition, sweetening taste-masking product and use thereof |
| CN111356376B (en) * | 2017-07-27 | 2024-01-05 | 健康科技生物活性剂有限公司 | Sweetening taste masking compositions, sweetening taste masking products and their use |
| WO2021147575A1 (en) * | 2020-01-20 | 2021-07-29 | 中国科学院分子植物科学卓越创新中心 | New carbon glycoside glycosyltransferase and use thereof |
| CN115024458A (en) * | 2022-06-14 | 2022-09-09 | 上海龙殷生物科技有限公司 | A method for improving taste and bitter taste of extract of plant of Rutaceae and Citrus |
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Application publication date: 20100714 |