CN104630315B - A kind of decompression enzyme process acylation method of black rice pigments - Google Patents
A kind of decompression enzyme process acylation method of black rice pigments Download PDFInfo
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- CN104630315B CN104630315B CN201310547628.9A CN201310547628A CN104630315B CN 104630315 B CN104630315 B CN 104630315B CN 201310547628 A CN201310547628 A CN 201310547628A CN 104630315 B CN104630315 B CN 104630315B
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- black rice
- rice pigments
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- added
- pigments
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- 239000000049 pigment Substances 0.000 title claims abstract description 31
- 241000371652 Curvularia clavata Species 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 16
- 102000004190 Enzymes Human genes 0.000 title claims abstract description 11
- 108090000790 Enzymes Proteins 0.000 title claims abstract description 11
- 230000006837 decompression Effects 0.000 title claims abstract description 10
- 230000010933 acylation Effects 0.000 title abstract description 6
- 238000005917 acylation reaction Methods 0.000 title abstract description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 229940095102 methyl benzoate Drugs 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 102000004882 Lipase Human genes 0.000 claims abstract description 7
- 108090001060 Lipase Proteins 0.000 claims abstract description 7
- 239000004367 Lipase Substances 0.000 claims abstract description 7
- 235000019421 lipase Nutrition 0.000 claims abstract description 7
- 238000004090 dissolution Methods 0.000 claims abstract description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims abstract description 5
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 235000013305 food Nutrition 0.000 abstract description 3
- 239000000284 extract Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 235000010208 anthocyanin Nutrition 0.000 description 5
- 229930002877 anthocyanin Natural products 0.000 description 5
- 239000004410 anthocyanin Substances 0.000 description 5
- -1 acyl group anthocyanin Chemical class 0.000 description 4
- VEVZSMAEJFVWIL-UHFFFAOYSA-O cyanidin cation Chemical compound [O+]=1C2=CC(O)=CC(O)=C2C=C(O)C=1C1=CC=C(O)C(O)=C1 VEVZSMAEJFVWIL-UHFFFAOYSA-O 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 150000004636 anthocyanins Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000007336 cyanidin Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000002019 anti-mutation Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000002864 food coloring agent Nutrition 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The present invention provides a kind of decompression enzyme process of black rice pigments to be acylated method, belongs to deep-processing technical field of agricultural products.Including by a small amount of pyridinium dissolution of black rice pigments, being separately added into methyl benzoate, Novozmy435 immobilized lipases, at reduced pressure conditions catalysis reaction 48 hours.Water is added after reaction and extracts product.This method solvent, enzyme are used multiple times, suitable mass production at low cost, and industrial prospect is good.The acylation black rice pigments of acquisition can be used as natural food pigment, be applied to different field.
Description
One, technical field
The present invention is that a kind of decompression enzyme process of black rice pigments is acylated method, belongs to deep-processing technical field of agricultural products.
Two, background technology
Black rice pigments are the water colo(u)rs extracted from black rice and black rice kind skin, rice bran.Research about black rice pigments
Show that black rice pigments belong to anthocyani pigment, main component is Cy-3-G.Black rice pigments have stronger
Physiological activity and the function such as lowering blood pressure and blood fat, anti-mutation, anti-oxidant, antitumor.As a kind of abundant raw material, easily extract
Natural food colour has prodigious potentiality to be exploited in food, health products, medicine, cosmetics etc., but due to black rice color
Plain main component is non-acyl group anthocyanin, so natural black rice pigment stability is poor, which limits it to process and store
Extensive use in journey.Anthocyanin stability can be improved in acylation, improves colouring effect, improves inoxidizability.Lipase is having
It can be catalyzed transesterification reaction in machine phase, the carboxyl groups in phenols acids can be transferred to the glucose of Cyanidin using this principle
On glycosides hydroxyl, realizes the acylation to anthocyanin, prepare the natural pigment raw material of high stability.Therefore, this method has weight
The theory value and realistic meaning wanted.
Three, invention content
The main component Cy-3-G of technical problem black rice pigments is non-acyl group anthocyanin, than purple sweet potato etc.
Acyl group anthocyanin stability is poor, easily fades.Also black rice pigments is made to be restricted as the application of food coloring.The main needle of the present invention
To the technical barrier of black rice pigments stability difference, by the way that the black rice pigments of preliminary purification are performed under reduced pressure in organic phase
Enzyme process be acylated, obtain stability-enhanced black rice pigments.
The technical solution present invention provides a kind of decompression enzyme process acylation method of black rice pigments, including：
1) preparation of reaction system：Black rice pigments are added in round-bottomed flask, a small amount of pyridinium dissolution is added, are added certain
The methyl benzoate of volume, Novozmy435 immobilized lipases, fully shakes up.
2) lower enzymic catalytic reaction is depressurized：Round-bottomed flask is packed on rotary evaporator, control pressure 0.09MPa, is slowly turned
It is dynamic, successive reaction 48 hours.Since the methanol that transesterification reaction generates is distilled out of, react to generation benzoyl Cyanidin glucose
The progress of glycosides direction,
3) product detaches：Certain volume water is added after reaction to stir evenly, pours into separatory funnel, standing takes after ten minutes
Layer aqueous solution filtering.Filtrate decompression is to be acylated black rice pigments, conversion ratio 30% or so after being concentrated to dryness.Separatory funnel lower layer
The molten object of oil is the mixture of unreacted methyl benzoate and enzyme, reusable after drying.
Advantageous effect
1. obtaining benzoylation black rice pigments, color stability is improved, and can be used as natural food pigment.
2. using immobilized lipase, it is used multiple times, reduces cost, is suitble to mass production, industrial prospect good.
Also it is reaction substrate 3. the use of methyl benzoate being both solvent.Methyl benzoate is unfunctionalized olefins product, safely may be used
It leans on, can be repeated several times utilization.
Four, specific implementation mode
Black rice pigments are added in round-bottomed flask, a small amount of pyridinium dissolution is added, adds the methyl benzoate of certain volume,
Novozmy435 immobilized lipases, fully shake up.Round-bottomed flask is packed on rotary evaporator, control pressure in 0.09MPa,
Successive reaction 48 hours.Certain volume water is added after reaction to stir evenly, pours into separatory funnel, standing takes upper water after ten minutes
Solution filters.Filtrate decompression is to be acylated black rice pigments after being concentrated to dryness.The molten object of separatory funnel lower layer oil is unreacted benzene
The mixture of methyl formate and enzyme, is reused after drying.
Embodiment
20 milligrams of black rice pigments are added in 250 milliliters of round-bottomed flasks, 1 milliliter of pyridinium dissolution is added, adds 10 milliliters
Methyl benzoate, 50 milligrams of Novozmy435 immobilized lipases, fully shakes up.Round-bottomed flask is packed on rotary evaporator,
Control pressure slowly rotates, successive reaction 48 hours in 0.09MPa.20 milliliters of water are added after reaction to stir evenly, pour into liquid separation
Funnel, standing take upper layer aqueous solution to filter after ten minutes.Filtrate decompression is to be acylated black rice pigments after being concentrated to dryness.
Claims (1)
1. a kind of decompression enzyme process of black rice pigments is acylated method, including：
1) reaction system prepares：Black rice pigments are added in round-bottomed flask, a small amount of pyridinium dissolution is added, adds certain volume
Methyl benzoate, Novozmy435 immobilized lipases, fully shakes up；
2) lower enzymic catalytic reaction is depressurized：Round-bottomed flask is packed on rotary evaporator, control pressure is in 0.09MPa, successive reaction
It 48 hours, since the methanol that transesterification reaction generates is distilled out of, reacts and is carried out to generation benzoyl C-3-G direction；
3) product detaches：Certain volume water is added after reaction to stir evenly, pours into separatory funnel, standing takes upper water after ten minutes
Solution filters, and filtrate decompression is as acylated black rice pigments after being concentrated to dryness, and conversion ratio 30% or so, separatory funnel lower layer oil is molten
Object is the mixture of unreacted methyl benzoate and enzyme, reusable after drying.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201310547628.9A CN104630315B (en) | 2013-11-06 | 2013-11-06 | A kind of decompression enzyme process acylation method of black rice pigments |
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| CN201310547628.9A CN104630315B (en) | 2013-11-06 | 2013-11-06 | A kind of decompression enzyme process acylation method of black rice pigments |
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| CN104630315A CN104630315A (en) | 2015-05-20 |
| CN104630315B true CN104630315B (en) | 2018-08-14 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114403224A (en) * | 2021-12-20 | 2022-04-29 | 蚌埠市和平乳业有限责任公司 | High-stability modified milk and preparation method thereof |
| CN116253708A (en) * | 2023-03-07 | 2023-06-13 | 陕西嘉禾生物科技股份有限公司 | Method for extracting anthocyanin from black rice |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1876824A (en) * | 2006-04-21 | 2006-12-13 | 华南理工大学 | Method for preparing cytosine arabinoside ester by enzyme catalysis |
| CN100999749A (en) * | 2007-01-05 | 2007-07-18 | 华南理工大学 | Process of preparing 5-fluorouradine ester by enzyme catalyzing |
-
2013
- 2013-11-06 CN CN201310547628.9A patent/CN104630315B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1876824A (en) * | 2006-04-21 | 2006-12-13 | 华南理工大学 | Method for preparing cytosine arabinoside ester by enzyme catalysis |
| CN100999749A (en) * | 2007-01-05 | 2007-07-18 | 华南理工大学 | Process of preparing 5-fluorouradine ester by enzyme catalyzing |
Non-Patent Citations (7)
| Title |
|---|
| Acylation of Anthocyanins From Black Rice and Their Stability Properties;Xiaoling Lu等;《Advanced Materials Research》;20110221;全文 * |
| Biological activities of flavonoids from Nitraria retusa (Forssk.) Asch.and their acylated derivatives;Jamila Hadj Salem等;《Food Chemistry》;20111231;第124卷;全文 * |
| David E. Stevenson等.Direct acylation of flavonoid glycosides with phenolic acids catalysed by Candida antarctica lipase B(Novozym 435®).《Enzyme and Microbial Technology》.2006,第39卷第1236–1241页. * |
| Enzymatic synthesis of new aromatic esters of phloridzin;E.Enaud等;《Journal of Molecular Catalysis B: Enzymatic》;20041231;第27卷;摘要部分，第2.2节，第3.2节、图7 * |
| 有机相中脂肪酶催化合成黄酮酯类研究进展;曹清丽等;《化学世界》;20130725(第7期);全文 * |
| 脂肪酶催化竹叶抗氧化物中异荭草苷和异牡荆苷酰化;马祥等;《食品科学》;20130104;第34卷(第16期);全文 * |
| 花色苷有机酸酰化及黄酮辅色研究进展;田小燕等;《农产品加工(学刊)》;20121130(第11期);全文 * |
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