CN101307344B - Method for hydrolyzing propolis flavonoid glycosideby by naringinase - Google Patents
Method for hydrolyzing propolis flavonoid glycosideby by naringinase Download PDFInfo
- Publication number
- CN101307344B CN101307344B CN2008100630547A CN200810063054A CN101307344B CN 101307344 B CN101307344 B CN 101307344B CN 2008100630547 A CN2008100630547 A CN 2008100630547A CN 200810063054 A CN200810063054 A CN 200810063054A CN 101307344 B CN101307344 B CN 101307344B
- Authority
- CN
- China
- Prior art keywords
- propolis
- flavonoid
- enzymolysis
- naringinase
- products
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 241000241413 Propolis Species 0.000 title claims abstract description 53
- 229940069949 propolis Drugs 0.000 title claims abstract description 53
- 229930003935 flavonoid Natural products 0.000 title claims abstract description 26
- 235000017173 flavonoids Nutrition 0.000 title claims abstract description 26
- 150000002215 flavonoids Chemical class 0.000 title claims abstract description 20
- 108010001078 naringinase Proteins 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 12
- 230000003301 hydrolyzing effect Effects 0.000 title claims abstract description 7
- -1 zytase Proteins 0.000 claims description 14
- 108090000790 Enzymes Proteins 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 9
- 229940088598 enzyme Drugs 0.000 claims description 9
- 238000002203 pretreatment Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 108010059892 Cellulase Proteins 0.000 claims description 3
- 108010059820 Polygalacturonase Proteins 0.000 claims description 3
- 108010047754 beta-Glucosidase Proteins 0.000 claims description 3
- 102000006995 beta-Glucosidase Human genes 0.000 claims description 3
- 229940106157 cellulase Drugs 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 2
- 238000001976 enzyme digestion Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 19
- 229930182486 flavonoid glycoside Natural products 0.000 abstract description 13
- 150000007955 flavonoid glycosides Chemical class 0.000 abstract description 13
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 abstract description 10
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 abstract description 10
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 abstract description 10
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000007791 liquid phase Substances 0.000 abstract 1
- 229930003944 flavone Natural products 0.000 description 17
- 235000011949 flavones Nutrition 0.000 description 17
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 15
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 15
- 150000002212 flavone derivatives Chemical class 0.000 description 12
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 6
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 5
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 3
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 3
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 description 3
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 3
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000012496 blank sample Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000007071 enzymatic hydrolysis Effects 0.000 description 3
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 3
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 235000008777 kaempferol Nutrition 0.000 description 3
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 3
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 description 3
- 235000007743 myricetin Nutrition 0.000 description 3
- 229940116852 myricetin Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000005875 quercetin Nutrition 0.000 description 3
- 229960001285 quercetin Drugs 0.000 description 3
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 3
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 3
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 3
- 235000005493 rutin Nutrition 0.000 description 3
- 229960004555 rutoside Drugs 0.000 description 3
- 241000256844 Apis mellifera Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000002213 flavones Chemical class 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000002019 anti-mutation Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000011987 flavanols Nutrition 0.000 description 1
- 229930003949 flavanone Natural products 0.000 description 1
- 150000002207 flavanone derivatives Chemical class 0.000 description 1
- 235000011981 flavanones Nutrition 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- 150000002216 flavonol derivatives Chemical class 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000013011 mating Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000006041 probiotic Substances 0.000 description 1
- 230000000529 probiotic effect Effects 0.000 description 1
- 235000018291 probiotics Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Images
Landscapes
- Jellies, Jams, And Syrups (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
The invention provides a method for hydrolyzing propolis flavonoid glycoside by naringinase. The method is as follows: naringinase is adopted to carry out constant-temperature enzymolysis of propolis flavonoid glycoside; propolis flavonoid glycoside substance is hydrolyzed into flavonoid aglycone through enzymolysis; moreover, compared with raw materials, the antioxidation property of the productis reinforced. The content of flavonoid substances in the obtained enzymolysis products can be measured through high-efficiency liquid phase chromatogram, and the result shows that the content of flavonoid glycoside substances is reduced, while the content of flavonoid aglycone substances is obviously increased. The method realizes deep development and utilization of propolis products, and is propitious to increase the added value of bee products and expand the application range of bee products. Moreover, the made propolis enzymolysis products has remarkably increased antioxidation property, and can be better used in the fields of medicine, foodstuff and cosmetics, etc. as compared with raw material propolis.
Description
Technical field
The invention belongs to the propolis processing technology, relate to a kind of method of hydrolyzing propolis flavonoid glycosideby by naringinase.
Technical background
Propolis (propolis) is that honeybee is gathered resin from plant plumule, bark and trunk crack, and sneaks into the colloidal solid thing with aromatic odour that its mandibular gland secretory product and beeswax process.Being called as " black wax " on the Arabic in ancient times medical book of propolis " doctor's allusion quotation ", also is one of main component of recording the earliest Nidus Vespae in Shennong's Herbal.Various biological effects such as propolis has the prevention wound infection, it is immune, antitumor, hypotensive to regulate, reducing blood-fat, hypoglycemic and resisting pathogenic microbes.The complex chemical composition of propolis contains flavonoid compound, acid, alcohol, phenol, aldehyde, ester, ethers and alkene, terpene, steroid and multiple amino acids, lipid acid, enzyme, VITAMIN and various trace elements.In these chemical ingredientss, because the flavonoid content height, biologic activity is strong, and therefore the research about flavonoid compound extraction and effect in the propolis becomes focus.
Flavonoid compound is the Polyphenols antioxidant that a class extensively distributes at nature.Studies show that in a large number flavonoid compound has removes free radical, anti-oxidant, anti-mutation, antitumor, antibiotic, antiviral and regulate function such as immunity, wherein the most important thing is its anti-oxidant activity.Flavonoid compound exists in the form of occurring in nature majority with flavonoid glycoside, has only the form with free Flavone aglycone of minute quantity to exist.Though naturally occurring free Flavone aglycone content is few, its activity that shows is high more a lot of than the glucosides of mating type.Flavone aglycone can directly be absorbed and enter animal blood, the chromocor compound of most of glucosides type can not enter into blood by small bowel in human body, but degraded and metabolism by the heterocycle fragmentation pattern by microorganism in the enteric cavity, the small portion flavones is wherein only arranged under the effect of colonic probiotic bacterium (milk-acid bacteria and bifidus bacillus) excretory lytic enzyme, the generation aglycon is reuptaked and is entered blood.Therefore, flavonoid glycoside bioavailability in animal body is well below aglycon type flavones.Studies show that the biological activity that Flavone aglycone is removed the human body oxyradical obviously is better than flavone glycoside, tiring of Flavone aglycone is 7 times that flavone glycoside is tired.
In the propolis the flavonoid compound that goes out of isolation identification kind more than 70 is arranged, wherein main have flavonoid, flavonols, flavanone and a flavanol compound.Discover that obtain four components after propolis is separated through silica gel adsorption, the general flavone content among the component I V is relatively higher than component I, II, III, its main component is exactly a flavonoid glycoside substance, so the content of flavonoid glycoside in propolis is than higher.
Because the enzyme specificity is strong, so the mild condition of enzyme process catalytic hydrolysis, can adopt weakly acidic damping fluid, Flavone aglycone is volatility not, is the effective way of industrial preparation high reactivity Flavone aglycone healthcare products.
Summary of the invention
Originally the method that the purpose of this invention is to provide a kind of hydrolyzing propolis flavonoid glycosideby by naringinase adopts naringinase that propolis flavonoid is carried out the constant temperature enzymolysis, specifically realizes by following steps:
Take by weighing propolis, be dissolved in water, adding beta-glucosidase, zytase, cellulase, polygalacturonase, α-Dian Fenmei are carried out the prozyme pre-treatment, enzyme dosage is respectively 10U/mg, 1500U/mL, 9U/mL, 50U/mL, 1.5U/mL, and in pH value 5.0, pre-treatment is 6 hours under 50 ℃ of conditions of temperature, add naringinase 5U/mg～30U/mg, regulate pH value 4～7, control concentration of substrate and be 30 ℃～60 ℃ of 0.2mg/mL～5mg/mL hydrolysis temperature, enzymolysis time 6～36 hours.It is even to remain solution in the reaction process.Enzymolysis finishes and adds dehydrated alcohol and make its final concentration reach 60% to make enzyme-deactivating.
Institute's enzymolysis product that obtains is through its Flavonoid substances content of high-performance liquid chromatogram determination, and the result shows that flavonoid glycoside substance content descends, and flavonoid glycoside metaclass substances content obviously improves.
The method of a kind of enzymolysis propolis flavonoid provided by the invention, by enzymolysis, propolis flavone glycoside material is hydrolyzed to Flavone aglycone, compares with raw material, and the antioxidant property of product strengthens.The present invention is the deep development utilization to propolis product, helps improving the added value of bee product, opens up its range of application.The propolis enzymolysis product antioxidant property that makes significantly improves, and than the raw material propolis, can be applied to fields such as medicine, foods and cosmetics better.
Description of drawings
Fig. 1 is 5 kinds of Flavonoid substances enzymolysis front and back content in the propolis.
Fig. 2 is the anti-Oxidation of Fat and Oils effect of propolis flavone enzymolysis product.
Fig. 3 is 5 kinds of Flavonoid substances enzymolysis front and back content in the propolis.
Fig. 4 is the anti-Oxidation of Fat and Oils effect of propolis flavone enzymolysis product.
Fig. 5 is 5 kinds of Flavonoid substances enzymolysis front and back content in the propolis.
Fig. 6 is the anti-Oxidation of Fat and Oils effect of propolis flavone enzymolysis product.
Embodiment
The present invention is further described in conjunction with the accompanying drawings and embodiments.
Get propolis 100mg, be dissolved in the 200mL distilled water, adding beta-glucosidase, zytase, cellulase, polygalacturonase, α-Dian Fenmei are carried out the prozyme pre-treatment, and enzyme dosage is respectively 10U/mg, 1500U/mL, 9U/mL, 50U/mL, 1.5U/mL, in pH value 5.0, pre-treatment is 6 hours under 50 ℃ of conditions of temperature, adds a certain amount of naringinase and transforms, and the control enzyme concn is 30U/mg, pH value 4.5,50 ℃ of temperature, enzymolysis time 24 hours, it is even to remain solution in the reaction process.Enzymolysis finishes and adds dehydrated alcohol and make its final concentration reach 60% to make enzyme-deactivating.The 198.4mg/100g of flavonoid glycoside substance rutin under this enzymatic hydrolysis condition in the products therefrom propolis before by enzymolysis is reduced to the 36.3mg/100g behind the enzymolysis, percent hydrolysis reaches 81.7%, the content of aglycon class material myricetin, Quercetin and kaempferol all increases to some extent, has improved 53.2%, 63.2% and 95.9% (referring to table 1, Fig. 1) respectively.
5 kinds of Flavonoid substances enzymolysis front and back content (mg/100g) in table 1 propolis
Accurately take by weighing the fresh lard of 50.0g, add 0.02% propolis therein, place 60 ± 2 ℃ thermostat container, its 2 days, the peroxide value (POV) 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days the time are measured in sampling regularly.
Press the regulation of GB/T5009.37-1996, lard POV 〉=0.20% is o'clock for exceeding standard.The POV of propolis enzymolysis product in the time of the 9th day is 0.2789%, and the POV of control group propolis is 0.5013%, and this moment, blank sample reached 0.6501% (referring to table 2, Fig. 2).The result shows that enzymolysis product has anti-preferably lard oxidation susceptibility, significantly is better than the raw material propolis.
Table 2 lard peroxide value (%)
Get propolis 200mg, be dissolved in the 200mL distilled water, carry out the prozyme pre-treatment with embodiment 1, add a certain amount of naringinase and transform, the control enzyme concn is 10U/mg, pH value 4.0, and 35 ℃ of temperature, enzymolysis time 9 hours, it is even to remain solution in the reaction process.Enzymolysis finishes and adds dehydrated alcohol and make its final concentration reach 60% to make enzyme-deactivating.The 198.4mg/100g of flavonoid glycoside substance rutin under this enzymatic hydrolysis condition in the products therefrom propolis before by enzymolysis is reduced to the 109.7mg/100g behind the enzymolysis, percent hydrolysis reaches 44.7%, the content of aglycon class material myricetin, Quercetin and kaempferol all increases to some extent, has improved 1.8%, 30.2% and 39.3% (referring to table 3, Fig. 3) respectively.
5 kinds of Flavonoid substances enzymolysis front and back content (mg/100g) in table 3 propolis
The POV of propolis enzymolysis product in the time of the 9th day is 0.4368%, and the POV of control group propolis is 0.5013%, and this moment, blank sample reached 0.6501% (referring to table 4, Fig. 4).
Table 4 lard peroxide value (%)
Get propolis 800mg, be dissolved in the 200mL distilled water, carry out the prozyme pre-treatment with embodiment 1, add a certain amount of naringinase and transform, the control enzyme concn is 5U/mg, pH value 6.5, and 60 ℃ of temperature, enzymolysis time 6 hours, it is even to remain solution in the reaction process.Enzymolysis finishes and adds dehydrated alcohol and make its final concentration reach 60% to make enzyme-deactivating.The 198.4mg/100g of flavonoid glycoside substance rutin under this enzymatic hydrolysis condition in the products therefrom propolis before by enzymolysis is reduced to the 136.8mg/100g behind the enzymolysis, percent hydrolysis reaches 31.0%, the content of aglycon class material myricetin, Quercetin and kaempferol all increases to some extent, has improved 5.3%, 18.8% and 20.2% (referring to table 5, Fig. 5) respectively.
5 kinds of Flavonoid substances enzymolysis front and back content (mg/100g) in table 5 propolis
The POV of propolis enzymolysis product in the time of the 9th day is 0.4673%, and the POV of control group propolis is 0.5013%, and this moment, blank sample reached 0.6501% (referring to table 6, Fig. 6).
Table 6 lard peroxide value (%)
Claims (2)
1. the method for a hydrolyzing propolis flavonoid glycosideby by naringinase is characterized in that realizing by following steps:
Take by weighing propolis, be dissolved in water, adding beta-glucosidase, zytase, cellulase, polygalacturonase, α-Dian Fenmei are carried out the prozyme pre-treatment, enzyme dosage is respectively 10U/mg, 1500U/mL, 9U/mL, 50U/mL, 1.5U/mL, in pH value 5.0, pre-treatment is 6 hours under 50 ℃ of conditions of temperature, add naringinase 5U/mg～30U/mg, regulate pH value 4～7, the control concentration of substrate is 30 ℃～60 ℃ of 0.2mg/mL～5mg/mL hydrolysis temperature, enzymolysis time 6～36 hours, enzymolysis finish and add dehydrated alcohol and make its final concentration reach 60% to make enzyme-deactivating.
2. the method for a kind of hydrolyzing propolis flavonoid glycosideby by naringinase according to claim 1, it is characterized in that: it is even to remain solution in the enzyme digestion reaction process.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100630547A CN101307344B (en) | 2008-07-08 | 2008-07-08 | Method for hydrolyzing propolis flavonoid glycosideby by naringinase |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008100630547A CN101307344B (en) | 2008-07-08 | 2008-07-08 | Method for hydrolyzing propolis flavonoid glycosideby by naringinase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101307344A CN101307344A (en) | 2008-11-19 |
| CN101307344B true CN101307344B (en) | 2011-05-04 |
Family
ID=40124022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008100630547A Expired - Fee Related CN101307344B (en) | 2008-07-08 | 2008-07-08 | Method for hydrolyzing propolis flavonoid glycosideby by naringinase |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101307344B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102321699A (en) * | 2011-06-24 | 2012-01-18 | 江苏江大源生态生物科技有限公司 | Method for composite enzymolysis-assisted extraction of active ingredient from propolis |
| CN103611333A (en) * | 2013-11-21 | 2014-03-05 | 江苏江大源生态生物科技有限公司 | Method for supercritical extraction of super natural factors of propolis by using CO2 fluid in combination with solid-state enzymolysis |
| CN106676143A (en) * | 2017-01-10 | 2017-05-17 | 江苏农林职业技术学院 | Pueraria flavone modification method |
| CN110464696A (en) * | 2019-09-18 | 2019-11-19 | 北京蜜慕科技有限公司 | A kind of preparation method and applications of small molecule propolis extract |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101089187A (en) * | 2006-06-14 | 2007-12-19 | 浙江工业大学 | Method for hydrolytic preparing biological tangeritin by enzyme |
| CN101100683A (en) * | 2006-09-08 | 2008-01-09 | 颜廷和 | Glucoside type flavone biological transformation and purification technique |
-
2008
- 2008-07-08 CN CN2008100630547A patent/CN101307344B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101089187A (en) * | 2006-06-14 | 2007-12-19 | 浙江工业大学 | Method for hydrolytic preparing biological tangeritin by enzyme |
| CN101100683A (en) * | 2006-09-08 | 2008-01-09 | 颜廷和 | Glucoside type flavone biological transformation and purification technique |
Non-Patent Citations (1)
| Title |
|---|
| 余兰平.蜂胶黄酮苷酶解与抗氧化活性的探讨.《蜜蜂杂志》.2007,(第1期),3-4. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101307344A (en) | 2008-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2682755C (en) | Fermented plant extracts, methods of production and uses | |
| KR101330864B1 (en) | Preparation for fermented-red gingseng or fermented-gingseng containing increased ginsenoside rd using pectinase | |
| Huo et al. | A preliminary study on polysaccharide extraction, purification, and antioxidant properties of sugar-rich filamentous microalgae Tribonema minus | |
| CN101307344B (en) | Method for hydrolyzing propolis flavonoid glycosideby by naringinase | |
| KR102044602B1 (en) | Preparation method for soybean-fermented composition having enhanced GABA, Conjugated linoleic acid and Aglycone isoflavones, combined probiotics for its fermentation and functional food of anti-diabetic and anti-obesity effects containing the soybean-fermented composition | |
| Eom et al. | Increased antioxidative and nitric oxide scavenging activity of ginseng marc fermented by Pediococcus acidilactici KCCM11614P | |
| Kwak et al. | Antioxidant activity and anti-inflammatory activity of ethanol extract and fractions of Doenjang in LPS-stimulated RAW 264.7 macrophages | |
| US10086029B2 (en) | Fermented plant extracts, methods of production and uses | |
| Constantin et al. | Bioactive Components, Applications, Extractions, and Health Benefits of Winery By-Products from a Circular Bioeconomy Perspective: A Review | |
| KR101980450B1 (en) | Composition of active wild-cultivated ginseng having increased ginsenoside Rd and compound K, chlorgenic acid and quercetin, and preparation method thereof | |
| CN117204568A (en) | Rosa roxburghii dietary fiber-bonded polyphenol with remarkable hypoglycemic activity, and extraction method and application thereof | |
| CN101307083B (en) | Method for acid-hydrolyzing propolis flavonoid glycoside | |
| Larios‐Cruz et al. | Extraction of bioactive molecules through fermentation and enzymatic assisted technologies | |
| Khawas et al. | Banana peels and their prospects for industrial utilization | |
| Kuo et al. | A process for high-efficiency isoflavone deglycosylation using Bacillus subtilis natto NTU-18 | |
| CN116407572A (en) | Sea buckthorn extract and preparation method and application thereof | |
| CN108450879A (en) | Conversion efficiently produces mammalian lignan method in degreasing linseed organism | |
| KR20190030850A (en) | Platycodon radix composition containing high protocatechuic acid, epicatechin, and oleic acid and enhanced inhibition activities of alpha-glucosidase and pancreatic lipase, and preparation method thereof | |
| Buzhylov et al. | Enzymatic modification of wheat bran | |
| CN103262970B (en) | Removed-sugar honey and preparation method thereof | |
| Cabanillas-Bojórquez et al. | Biotechnology for extraction of plant phenolics | |
| Lopes et al. | The importance of microbial and enzymatic bioconversions of isoflavones in bioactive compounds | |
| CN101555275A (en) | Method for preparing alpha-amylase inhibitor by enzymatic method | |
| CN108441527A (en) | A method of preparing rhamnetin using bioenzymatic conversion | |
| CN102796676A (en) | Bacteroides uniformis Strain-I and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20110504 Termination date: 20150708 |
|
| EXPY | Termination of patent right or utility model |