CN104877389A - Natural plant pigment and preparation method thereof - Google Patents
Natural plant pigment and preparation method thereof Download PDFInfo
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- CN104877389A CN104877389A CN201510213955.XA CN201510213955A CN104877389A CN 104877389 A CN104877389 A CN 104877389A CN 201510213955 A CN201510213955 A CN 201510213955A CN 104877389 A CN104877389 A CN 104877389A
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- xanthohumol
- cyclodextrin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
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Abstract
The invention relates to a natural plant pigment and a preparation method thereof, belonging to the field of extraction and application of natural products. The preparation method comprises the following steps: by using humulus lupulus or waste humulus lupulus residues generated in the humulus lupulus working process as a raw material, extracting and separating to obtain a yellow extract of which the main active component is xanthohumol; and purifying the extract to obtain the xanthohumol yellow crystal or powder. The crystal or powder is insoluble or slightly soluble in water. In order to widen the application range, cyclodextrin is utilized to include the crystal or powder to obtain the xanthohumol cyclodextrin inclusion compound which is applicable to beer, medicine, food proportioning, beverage proportioning, health-care tea proportioning, cosmetics and dye industry.
Description
Technical field
The present invention relates to a kind of natural plant pigment and preparation method thereof, belong to natural product extraction and Application Areas.More specifically, the present invention relates to a kind of with the discarded hop residue produced in hops or the hops course of processing for raw material, obtain a kind of yellow extract through extracting and developing, the main active ingredient of this extract is xanthohumol, will obtain yellow crystals or the powder of xanthohumol after extract purifying; Above-mentioned crystal or powder water insoluble or be slightly soluble in water, for expanding its use range, adopt again cyclodextrin encapsulated further, obtain the xanthohumol cyclodextrin inclusion compound of the use being applicable to beer, medicine, food ingredients, beverage ingredient, health tea batching, makeup and dyestuffs industries.
Background technology
Hops, formal name used at school Humulus lupulus L, another name hop, top must colored, Tang's showy flowers of herbaceous plants, hops, lupulus, hops etc., for Urticales Cannabaceae Humulus per nnial herb, be one of main raw material of beer brewing, the fragrance of beer uniqueness and bitter taste and preservative activity can be supplied to.Hops is also the time-honored medicinal and edible plant of a kind of use, is rich in the multiple effective components such as hop resin, hops oil, polyphenol, flavones, has antibacterial, calm, the pharmacological function of the illnesss such as treatment tuberculosis, neurasthenia, leprosy.Xanthohumol is the simple prenyl phenyl styryl ketone of a kind of structure in hops, is also one of Flavonoid substances main in hops, and its structure gives its multiple physiologically active.As a kind of active components of plants of natural origin, xanthohumol has beautiful color and luster, and good light stability, in traditional beer product, namely impart the soft color and luster of beer.
In recent years, along with deepening continuously of studying xanthohumol, the various health care that xanthohumol has human body and pharmacological action are verified gradually.But due to the exclusive source that hops is occurring in nature xanthohumol, therefore drinks beer has just become people to absorb the unique channel of xanthohumol substantially.At present, existing many research, at the various physiologically actives paying close attention to xanthohumol, also has the report added in medicine or healthcare products.As Chinese patent CN200910089533.0 discloses a kind of preparation method being rich in xanthohumol beer, CN02807794.6 discloses the purposes of hop components in food, CN200810061875.7 discloses a kind of sperm and ovum health beverage, CN200910039245.4 discloses a kind of production method of health-care beer, CN200710120424.1 discloses has auxiliary inhibiting health-care beer and preparation method thereof to tumour, CN200480013784.6 discloses for the composition suppressed or prevent bone density to reduce, food and drink etc. are all using xanthohumol as its main active ingredient.
And about also having a large amount of bibliographical informations to the work of xanthohumol extracting and developing and purifying.Wherein, Chinese patent CN200480037757.2 discloses the production method of the Flos lupuli (Flos Humuli Lupuli) extract with oestrogenic hormon and antiproliferative activity, CN200680035064.9 discloses Flos lupuli (Flos Humuli Lupuli) extract and preparation method thereof and application, CN200810037197.0 discloses Flos lupuli (Flos Humuli Lupuli) extract and preparation method thereof and application, CN200810073983.6--is containing the preparation method of the Flos lupuli (Flos Humuli Lupuli) extract of xanthohumol, CN200910089532.6 discloses the method extracting xanthohumol in hop residue with SFE-CO 2, CN201010045507.0 discloses a kind of method of utilizing hop residues to extract xanthohumol, the industrialized preparing process of CN201010167119.X--high-purity xanthohumol, CN201310053195.1 discloses containing the natural extract of xanthohumol and preparation method thereof and by its obtained product, CN201310449828.0 discloses a kind of method extracting xanthohumol from hops extract remainder, CN201410182552.9 discloses a kind of method etc. being separated xanthohumol from hops.The problem of xanthohumol poorly water-soluble has also caused the concern of researchist, and namely Chinese patent CN201110122090.8 discloses and improve the water miscible method of xanthohumol.The method makes xanthohumol and cyclodextrin in Diluted Alcohol, underpressure distillation recovered alcohol, filters the aqueous solution obtaining cyclodextrin-xanthohumol inclusion compound; Cyclodextrin-xanthohumol inclusion compound powder-product is obtained again by drying.Although aforesaid method have also been obtained one improve the water miscible product of xanthohumol, preparation process is complicated, and with an organic solvent ethanol, product last handling process also needs recycling design etc.
Summary of the invention
Raising along with quality of life and the pursuit to health, increasing employing natural pigment replaces synthetic colour has become the first-selection of following people in healthy pollution-free food production, also be one of focus of the research of current field of functional food, Lyeopene, carotene, alkannin, various anthocyanogen etc. as natural origin all play important physiological function while providing the tempting color and luster of food, but because natural pigment content is low, extraction cost is high, majority can only be applied in the higher functional foodstuff of value or healthcare products.Xanthohumol is higher as a kind of content of food color in hops of natural origin, and the China large hops producing region that is third place in the world, output is very considerable, has good DEVELOPMENT PROSPECT.The object of this invention is to provide in a kind of discarded hop residue produced from hops or the hops course of processing and extract a kind of natural plant pigment with functionally active, for overcoming the narrow defect of the plant pigments xanthohumol poorly water-soluble, the range of application that directly obtain, the invention provides the cyclodextrin encapsulated xanthohumol of a kind of employing, obtain the xanthohumol-cyclodextrin inclusion compound of the good water solubility that may be used in beer, medicine, food ingredients, beverage ingredient, health tea batching, makeup and dyestuffs industries.Without the need to adding any organic solvent in the preparation process of this inclusion compound, directly by xanthohumol and cyclodextrin mixed grinding or with a small amount of water by cyclodextrin and xanthohumol furnishing pasty state, adopt polishing to carry out inclusion.The preparation process of whole inclusion compound is without the need to using solvent or only using a small amount of water for solvent, gained xanthohumol-cyclodextrin inclusion compound is natural, nontoxic, harmless, good water solubility, without adding any poisonous, harmful solvent and chemical substance in whole preparation process, without hazardous emission, meet the requirement of green chemistry chemical technology.
To achieve these goals, the present invention adopts following technical scheme to be achieved:
A kind of natural plant pigment and preparation method thereof, is characterized in that comprising the following steps:
(1) with the discarded hop residue produced in hops or the hops course of processing for raw material, through extracting and developing, purifying obtain content 80% ~ 99.5% xanthohumol purification thing, xanthohumol after purification is yellow crystals or powder, water insoluble or be slightly soluble in water;
(2) by the xanthohumol crystal that obtains in above-mentioned steps (1) or powder, mix with the ratio uniform of weight ratio 1:15 ~ 1:200 with cyclodextrin, at selected temperature, adopt polishing to carry out inclusion, after the grinding of 0.5-3 hour, obtain the xanthohumol-cyclodextrin inclusion compound that can be dissolved in water;
(3) xanthohumol-cyclodextrin inclusion compound obtained in above-mentioned steps (2) can directly make an addition in beer to produce the beer being rich in xanthohumol;
A kind of preparation method of natural plant pigment, it is characterized in that described cyclodextrin is alpha-cylodextrin, beta-cyclodextrin, γ – cyclodextrin, hydroxypropyl-beta-cyclodextrin, 2-methyl-B-cyclodextrin, 2, 6-DM-β-CD and 2, 3, one in 6-TM-β-CD, the inclusion compound obtained is respectively xanthohumol-alpha-cylodextrin inclusion compound, xanthohumol-Benexate Hydrochloride, xanthohumol-γ – cyclodextrin inclusion compound, xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, xanthohumol-2-methyl-B-cyclodextrin inclusion compound, xanthohumol-2, 6-DM-β-CD inclusion compound and xanthohumol-2, 3, 6-TM-β-CD inclusion compound, preferred xanthohumol-cyclodextrin inclusion compound is xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion.
A preparation method for natural plant pigment, is characterized in that the ratio preferably 1:20 ~ 1:50 of described xanthohumol and cyclodextrin.
A preparation method for natural plant pigment, is characterized in that described selected grinding temperature scope is 20 DEG C ~ 80 DEG C.
A kind of natural plant pigment, is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of functional natural plant pigment.
A kind of natural plant pigment, it is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of water miscible natural yellow pigment, can be used in various beer, alcoholic beverage, soft drink, candy, jelly, biscuit, cake, simultaneously because xanthohumol itself has multiple pharmacologically active, the batching of healthcare products also can be it can be used as to use.
Beneficial effect acquired by the present invention is:
The present invention has substantial feature and significant technical progress, any organic solvent is not adopted in the preparation process of xanthohumol-cyclodextrin inclusion compound, directly pass through to grind xanthohumol-cyclodextrin inclusion compound that certain hour can obtain good water solubility by than row mixing xanthohumol and cyclodextrin, or by xanthohumol and cyclodextrin by than arrange mix after a small amount of water reconcile into pasty state, the xanthohumol-cyclodextrin inclusion compound of good water solubility can be obtained after then adopting polishing to be ground for some time.Whole preparation process uses environment and human body toxic organics or chemical substance without any, discharges without hazardous and noxious substances, solve the problem of ecotope from beginning of production, meet the requirement of Sustainable development; Preparation time is short simultaneously, and technique is simple, improves the water miscible effect of xanthohumol obvious, maintains its natural quality.As a kind of natural plant pigment with functionally active, can directly be made an addition in beer, also as the raw material of the industries such as medicine, food, beverage, health tea, makeup, dyeing and batching, wide adaptability, active high can be had.
A kind of preparation method of natural plant pigment, it is characterized in that described cyclodextrin is alpha-cylodextrin, beta-cyclodextrin, γ – cyclodextrin, hydroxypropyl-beta-cyclodextrin, 2-methyl-B-cyclodextrin, 2, 6-DM-β-CD and 2, 3, one in 6-TM-β-CD, the inclusion compound obtained is respectively xanthohumol-alpha-cylodextrin inclusion compound, xanthohumol-Benexate Hydrochloride, xanthohumol-γ – cyclodextrin inclusion compound, xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, xanthohumol-2-methyl-B-cyclodextrin inclusion compound, xanthohumol-2, 6-DM-β-CD inclusion compound and xanthohumol-2, 3, 6-TM-β-CD inclusion compound, preferred xanthohumol-cyclodextrin inclusion compound is xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion.
A preparation method for natural plant pigment, is characterized in that the ratio preferably 1:20 ~ 1:50 of described xanthohumol and cyclodextrin.
A preparation method for natural plant pigment, is characterized in that described selected grinding temperature scope is 20 DEG C ~ 80 DEG C.
A kind of natural plant pigment, is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of functional natural plant pigment.
A kind of natural plant pigment, it is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of water miscible natural yellow pigment, can be used in various beer, alcoholic beverage, soft drink, candy, jelly, biscuit, cake, simultaneously because xanthohumol itself has multiple pharmacologically active, the batching of healthcare products also can be it can be used as to use.
Beneficial effect acquired by the present invention is:
The present invention has substantial feature and significant technical progress, any organic solvent is not adopted in the preparation process of xanthohumol-cyclodextrin inclusion compound, directly pass through to grind xanthohumol-cyclodextrin inclusion compound that certain hour can obtain good water solubility by than row mixing xanthohumol and cyclodextrin, or by xanthohumol and cyclodextrin by than arrange mix after a small amount of water reconcile into pasty state, the xanthohumol-cyclodextrin inclusion compound of good water solubility can be obtained after then adopting polishing to be ground for some time.Whole preparation process uses environment and human body toxic organics or chemical substance without any, discharges without hazardous and noxious substances, solve the problem of ecotope from beginning of production, meet the requirement of Sustainable development; Preparation time is short simultaneously, and technique is simple, improves the water miscible effect of xanthohumol obvious, maintains its natural quality.As a kind of natural plant pigment with functionally active, can directly be made an addition in beer, also as the raw material of the industries such as medicine, food, beverage, health tea, makeup, dyeing and batching, wide adaptability, active high can be had.
After xanthohumol and cyclodextrin are mixed in proportion, adding a small amount of water makes the mixture of xanthohumol and cyclodextrin become mashed prod, the grinding of this mashed prod, after 0.5-3 hour, is placed in baking oven low temperature under the condition of 40 ~ 60 DEG C and is dried to constant weight, obtain water miscible xanthohumol-cyclodextrin inclusion compound.
A kind of preparation method of natural plant pigment, it is characterized in that described cyclodextrin is alpha-cylodextrin, beta-cyclodextrin, γ – cyclodextrin, hydroxypropyl-beta-cyclodextrin, 2-methyl-B-cyclodextrin, 2, 6-DM-β-CD and 2, 3, one in 6-TM-β-CD, the inclusion compound obtained is respectively xanthohumol-alpha-cylodextrin inclusion compound, xanthohumol-Benexate Hydrochloride, xanthohumol-γ – cyclodextrin inclusion compound, xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, xanthohumol-2-methyl-B-cyclodextrin inclusion compound, xanthohumol-2, 6-DM-β-CD inclusion compound and xanthohumol-2, 3, 6-TM-β-CD inclusion compound, preferred xanthohumol-cyclodextrin inclusion compound is xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion.
A preparation method for natural plant pigment, is characterized in that the ratio preferably 1:20 ~ 1:50 of described xanthohumol and cyclodextrin.
A preparation method for natural plant pigment, is characterized in that described selected grinding temperature scope is 20 DEG C ~ 80 DEG C.
A kind of natural plant pigment, is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of functional natural plant pigment.
A kind of natural plant pigment, it is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of water miscible natural yellow pigment, can be used in various beer, alcoholic beverage, soft drink, candy, jelly, biscuit, cake, simultaneously because xanthohumol itself has multiple pharmacologically active, the batching of healthcare products also can be it can be used as to use.
Beneficial effect acquired by the present invention is:
The present invention has substantial feature and significant technical progress, any organic solvent is not adopted in the preparation process of xanthohumol-cyclodextrin inclusion compound, directly pass through to grind xanthohumol-cyclodextrin inclusion compound that certain hour can obtain good water solubility by than row mixing xanthohumol and cyclodextrin, or by xanthohumol and cyclodextrin by than arrange mix after a small amount of water reconcile into pasty state, the xanthohumol-cyclodextrin inclusion compound of good water solubility can be obtained after then adopting polishing to be ground for some time.Whole preparation process uses environment and human body toxic organics or chemical substance without any, discharges without hazardous and noxious substances, solve the problem of ecotope from beginning of production, meet the requirement of Sustainable development; Preparation time is short simultaneously, and technique is simple, improves the water miscible effect of xanthohumol obvious, maintains its natural quality.As a kind of natural plant pigment with functionally active, can directly be made an addition in beer, also as the raw material of the industries such as medicine, food, beverage, health tea, makeup, dyeing and batching, wide adaptability, active high can be had.
Embodiment
Adopt the mode of specific embodiment to explain the present invention particularly below, but the present invention is not limited to embodiment.
Embodiment 1
By 0.1g xanthohumol respectively with 10g alpha-cylodextrin, 10g beta-cyclodextrin, 10g γ-cyclodextrin, 10g 2-methyl-B-cyclodextrin, 10g 2, 6-dimethyl-β-cyclodextrin, 10g 2, 3, 6-trimethylammonium beta-cyclodextrin, the mixing of 10g hydroxypropyl-beta-cyclodextrin is placed in mortar, and add 10mL distilled water furnishing pasty state respectively in the mixture, grinding 1h, then to be placed in baking oven low temperature under the condition of 40-60 DEG C and to be dried to constant weight, obtain xanthohumol-alpha-cylodextrin inclusion compound respectively, xanthohumol-Benexate Hydrochloride, xanthohumol-γ-cyclodextrin inclusion compound, xanthohumol-2-methyl-B-cyclodextrin inclusion compound, xanthohumol-2, 6-dimethyl-β-cyclodextrin inclusion compound, xanthohumol-2, 3, 6-trimethylammonium Benexate Hydrochloride, xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion.By analysis, the yield of above-mentioned inclusion compound and inclusion rate data are obtained in table 1.
The comparison of the different cyclodextrin encapsulated effect of table 1
Embodiment 2
0.1g xanthohumol and 5g beta-cyclodextrin being mixed directly is placed in mortar, under the condition not adding any solvent, carry out dry grinding 2h, obtain xanthohumol-Benexate Hydrochloride, by analysis, the yield of inclusion compound is 96.25%, and inclusion rate is 27.34%.
Embodiment 3
0.2g xanthohumol and 4g hydroxypropyl-beta-cyclodextrin being mixed directly is placed in mortar, under the condition not adding any solvent, carry out dry grinding 1.5h, obtain xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, by analysis, the yield of inclusion compound is 95.47%, and inclusion rate is 45.34%.
Embodiment 4
0.5g xanthohumol and 25g hydroxypropyl-beta-cyclodextrin being mixed directly is placed in mortar, add 15mL deionized water by its furnishing pasty state, grinding 40min, then to be placed in baking oven low temperature under the condition of 40-60 DEG C and to be dried to constant weight, obtain xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, by analysis, the yield of inclusion compound is 98.75%, and inclusion rate is 98.04%.
Embodiment 5
5g xanthohumol and 200g hydroxypropyl-beta-cyclodextrin being mixed directly is placed in motor-driven mill, add 100mL distilled water, opening power, grinding 300min, then to be placed in baking oven low temperature under the condition of 40-60 DEG C and to be dried to constant weight, obtain xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, by analysis, the yield of inclusion compound is 94.75%, and inclusion rate is 97.36%.
Claims (8)
1. natural plant pigment and preparation method thereof, is characterized in that comprising the following steps:
(1) with the discarded hop residue produced in hops or the hops course of processing for raw material, through extracting and developing, purifying obtain content 80% ~ 99.5% xanthohumol purification thing, xanthohumol after purification is yellow crystals or powder, water insoluble or be slightly soluble in water;
(2) by the xanthohumol crystal that obtains in above-mentioned steps (1) or powder, mix with the ratio uniform of weight ratio 1:15 ~ 1:200 with cyclodextrin, at selected temperature, adopt polishing to carry out inclusion, after the grinding of 0.5-3 hour, obtain the xanthohumol-cyclodextrin inclusion compound that can be dissolved in water;
(3) xanthohumol-cyclodextrin inclusion compound obtained in above-mentioned steps (2) can directly make an addition in beer to produce the beer being rich in xanthohumol;
(4) xanthohumol-cyclodextrin inclusion compound obtained in above-mentioned steps (2) can as whole food yellow pigment in beverage, candy, biscuit and various protective foods.
2. method according to claim 1, it is characterized in that described xanthohumol and cyclodextrin encapsulated method be not for add any solvent, after directly xanthohumol and cyclodextrin being mixed in proportion, after dry grinding 0.5-3 hour, obtain water miscible xanthohumol-cyclodextrin inclusion compound.
3. method according to claim 1, it is characterized in that described xanthohumol and cyclodextrin encapsulated method are after xanthohumol and cyclodextrin being mixed in proportion, adding a small amount of water makes the mixture of xanthohumol and cyclodextrin become mashed prod, by the grinding of this mashed prod after 0.5-3 hour, be placed in baking oven low temperature under the condition of 40 ~ 60 DEG C and be dried to constant weight, obtain water miscible xanthohumol-cyclodextrin inclusion compound.
4. method according to claim 1, it is characterized in that described cyclodextrin is alpha-cylodextrin, beta-cyclodextrin, γ – cyclodextrin, hydroxypropyl-beta-cyclodextrin, 2-methyl-B-cyclodextrin, 2, 6-DM-β-CD and 2, 3, one in 6-TM-β-CD, the inclusion compound obtained is respectively xanthohumol-alpha-cylodextrin inclusion compound, xanthohumol-Benexate Hydrochloride, xanthohumol-γ – cyclodextrin inclusion compound, xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion, xanthohumol-2-methyl-B-cyclodextrin inclusion compound, xanthohumol-2, 6-DM-β-CD inclusion compound and xanthohumol-2, 3, 6-TM-β-CD inclusion compound, preferred xanthohumol-cyclodextrin inclusion compound is xanthohumol-hydroxypropyl-beta-cyclodextrin inclusion.
5. method according to claim 1, is characterized in that the ratio preferably 1:20 ~ 1:50 of described xanthohumol and cyclodextrin.
6. method according to claim 1, is characterized in that described selected grinding temperature scope is 20 DEG C ~ 80 DEG C.
7. natural plant pigment according to claim 1, is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of functional natural plant pigment.
8. natural plant pigment according to claim 1, it is characterized in that obtained xanthohumol-cyclodextrin inclusion compound is a kind of water miscible natural yellow pigment, can be used in various beer, alcoholic beverage, soft drink, candy, jelly, biscuit, cake, simultaneously because xanthohumol itself has multiple pharmacologically active, the batching of healthcare products also can be it can be used as to use.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106074471A (en) * | 2016-07-14 | 2016-11-09 | 新疆大学 | A kind of preparation method of new bacteriostatic agent hexahydro β acid cyclodextrin clathrate |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106074471A (en) * | 2016-07-14 | 2016-11-09 | 新疆大学 | A kind of preparation method of new bacteriostatic agent hexahydro β acid cyclodextrin clathrate |
| CN106074471B (en) * | 2016-07-14 | 2018-12-07 | 新疆大学 | A kind of preparation method of new bacteriostatic agent hexahydro β-acid cyclodextrin inclusion compound |
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Application publication date: 20150902 |