CN103535726B - A kind of compound combination with collaborative effect of scavenging radical - Google Patents
A kind of compound combination with collaborative effect of scavenging radical Download PDFInfo
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- CN103535726B CN103535726B CN201310500694.0A CN201310500694A CN103535726B CN 103535726 B CN103535726 B CN 103535726B CN 201310500694 A CN201310500694 A CN 201310500694A CN 103535726 B CN103535726 B CN 103535726B
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- calycosin
- scavenging
- rattletop
- radix astragali
- isoferulic acid
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- 230000000694 effects Effects 0.000 title abstract description 13
- 230000002000 scavenging effect Effects 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 title abstract description 7
- ZZAJQOPSWWVMBI-UHFFFAOYSA-N calycosin Chemical compound C1=C(O)C(OC)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZZAJQOPSWWVMBI-UHFFFAOYSA-N 0.000 claims abstract description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 claims abstract description 17
- -1 DPPH free radical Chemical class 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- MQUFGUZKWBCWMX-UHFFFAOYSA-N CO.C(C=CC1=CC(O)=C(OC)C=C1)(=O)O Chemical compound CO.C(C=CC1=CC(O)=C(OC)C=C1)(=O)O MQUFGUZKWBCWMX-UHFFFAOYSA-N 0.000 claims description 5
- 230000007760 free radical scavenging Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000009636 Huang Qi Substances 0.000 abstract description 23
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 abstract description 10
- QURCVMIEKCOAJU-HWKANZROSA-N Isoferulic acid Natural products COC1=CC=C(\C=C\C(O)=O)C=C1O QURCVMIEKCOAJU-HWKANZROSA-N 0.000 abstract description 10
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 abstract description 10
- 239000003963 antioxidant agent Substances 0.000 abstract description 7
- 230000003078 antioxidant effect Effects 0.000 abstract description 7
- 230000002292 Radical scavenging effect Effects 0.000 abstract description 5
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- 238000013459 approach Methods 0.000 abstract description 2
- 238000001514 detection method Methods 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 abstract description 2
- 239000012634 fragment Substances 0.000 description 23
- 239000000284 extract Substances 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000002026 chloroform extract Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 230000008485 antagonism Effects 0.000 description 5
- 238000012216 screening Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000036542 oxidative stress Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- CNHOGQMRRDHYGI-NJCGARBWSA-N beta-onocerin Chemical group C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC(C)=C2CCC1=C(C)CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C CNHOGQMRRDHYGI-NJCGARBWSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 235000013376 functional food Nutrition 0.000 description 2
- 241000411851 herbal medicine Species 0.000 description 2
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007418 data mining Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 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
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/90—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving iron binding capacity of blood
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2500/00—Screening for compounds of potential therapeutic value
- G01N2500/20—Screening for compounds of potential therapeutic value cell-free systems
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Chemical & Material Sciences (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Food Science & Technology (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Cell Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to a kind of compound combination with collaborative effect of scavenging radical, DPPH radicals scavenging experiment is adopted to carry out active tracing detection, docs-effect analytic approach based on intermediate value effect principle evaluates the synergy (combination coefficient of two groups of antioxidant contents, CI), from the Radix Astragali and rattletop, the compound that one group is worked in coordination with scavenging free radicals is filtered out: calycosin and isoferulic acid.The methanol solution of calycosin and isoferulic acid is pressed different dose ratio (3:1,2:1,1:1,1:2,1:3) combine, measure its DPPH radical scavenging activity, find that calycosin and isoferulic acid show best synergistic function under the condition of dose ratio 1:1.
Description
(1) technical field
The present invention relates to a kind of compound combination with collaborative effect of scavenging radical, belong to health food development field.
(2) background technology
The formation of aging population society makes the incidence of disease of aging-related disease as cardiovascular disease, parkinsonism, Alzheimer disease etc. increase year by year, the chronic diseases such as the cancer of some the elderly Yi Fa also in rejuvenation trend, all cause great medical burden to the country and people in recent years.Research finds, preventing and improving sub-health state is prevent and alleviate the pathogenetic important channel of above disease, is then wherein one of method of outbalance and economy by dietary adjustments.At present, much research has confirmed that oxidative stress is directly or indirectly closely related with various disease, and the oxidative stress that simultaneously stress mediate also is considered to the starting stage of sub-health state.Therefore, find some natural safe polyphenoils make an addition to food be alleviate oxidative stress, prevention sub-health state important channel.
China's natural resources of Chinese medicinal materials enriches, and is the important sources of natural, and research and development Chinese medicine source functional food has become focus and the development trend of China's food research.System of Chinese medicine is particular about the application of compatibility compound, can play the effect of collaborative or antagonism thus carry out integrally-regulated to body after each medicine compatibility, shows attenuation, synergy and even produces the pharmacologically active that simple do not possess.From Chinese medicine, screen at present oxidation-resistant active ingredient is material mainly with single medicinal material greatly, to obtain single antioxidant content for target, seldom studies from the synergy of angle to multiple antioxidant content of herbal mixture.
The Radix Astragali and rattletop all belong to both for medicine and food herbal medicine, and the Radix Astragali is conventional Qi-tonifying drug, protect the liver, diuresis, hypotensive and effect such as to delay senility, rattletop is usually used in clearing heat and detoxicating, anti-inflammatory, slows down pain.In Chinese traditional treatment, doctor by virtue of experience often uses two medicines pairings, thus obtains better curative effect, but this synergy active component behind and mechanism of action still indefinite.Therefore from these two kinds of herbal medicine, filter out collaborative antioxidant content, to developing the functional food relevant to oxidative stress and obtaining the aspects such as NEW TYPE OF COMPOSITE antioxidant, there is important theory value.
(3) summary of the invention
The present invention adopts DPPH radicals scavenging experiment to carry out activity to sample separation and follows the tracks of, adopt based on the docs-effect analytic approach of intermediate value effect principle the synergy (combination coefficient of antioxidant content, CI) evaluate, adopt the methods such as extraction, extraction, column chromatography, HPLC, HPLC-MS coupling to carry out separation andpreconcentration to potential collaborative antioxidant content, from the Radix Astragali and rattletop, filter out one group work in coordination with the compound removing DPPH free radical: calycosin and isoferulic acid (table 1).
By the calycosin methanol solution of same concentrations and isoferulic acid methanol solution difference 3:1 by volume; 2:1; 1:1; 1:2; 1:3 fits over together, and evaluate its collaborative ability (table 2) removing DPPH free radical, the calycosin methanol solution of discovery same concentrations and isoferulic acid methanol solution combine and can show best synergistic function (CI under the condition of volume ratio 1:1
50, 0.770).
The DPPH radical scavenging activity of each standard substance of table 1 and combination thereof and synergy
Note:
arepresent and do not detect.
EC
50the concentration of required sample when referring to that free radical scavenging activity is 50%, concentration is less, and Scavenging activity is stronger; CI
50refer to the combination coefficient value (CI) when clearance rate is 50%.During CI value≤0.9, represent synergy, CI value is less, acts synergistically stronger; Addition is represented during 0.9<CI<1.1; During CI value >=1.1, represent antagonism, CI value is larger, and antagonism is stronger.
The CI match value of DPPH free radical is removed in table 2 isoferulic acid and the combination of calycosin different proportion
Note: A: isoferulic acid, B: calycosin
CI
50refer to the combination coefficient value (CI) when clearance rate is 50%.During CI value≤0.9, represent synergy, CI value is less, acts synergistically stronger; Addition is represented during 0.9<CI<1.1; During CI value >=1.1, represent antagonism, CI value is larger, and antagonism is stronger.
(4) accompanying drawing explanation
Fig. 1: synergistic combination screening process figure.
In Fig. 11 extracts; 2 is be separated; 3 is the collaborative scavenging free radicals components of screening; 4 is Active fraction appraisals; 5 is dosage effect evaluations.
(5) detailed description of the invention
(1) screening of the solvent extract removing DPPH free radical worked in coordination with by the Radix Astragali, rattletop: Radix Astragali medicinal powder volume fraction be 85% ~ 95% alcohol heating reflux extract, rotary evaporation is concentrated into medicinal extract.Add and make suspension with the deionized water of the quality such as medicinal extract, be placed in separatory funnel, carry out fractional extraction with benzinum, chloroform, ethyl acetate, n-butanol successively, collect the petroleum ether extract, chloroform extract, acetic acid ethyl ester extract and the n-butyl alcohol extract that obtain the Radix Astragali after each solvent extraction liquid is concentrated into medicinal extract respectively.Rattletop medicinal powder adopts said method to extract equally and extraction obtains rattletop petroleum ether extract, chloroform extract, acetic acid ethyl ester extract and n-butyl alcohol extract.By measuring 4 kinds of extracts of the Radix Astragali and the DPPH radical scavenging activity of 4 kinds of extracts of rattletop and Radix Astragali extract and working in coordination with scavenging ability of DPPH free radical time rattletop extract combination of interactions (two medicines are 1:1 combination by volume under the condition that concentration is identical) and filter out the compartment analysis that Radix Astragali chloroform extract and rattletop chloroform extract carry out next step.
(2) collaborative screening of removing the column chromatography fragment of DPPH free radical in the Radix Astragali chloroform extract obtained in (1) and rattletop chloroform extract: the elution requirement of Radix Astragali chloroform extract is for first benzinum/acetone is by (16:4,15:5,14:6,11:9, v/v) wash-out successively, then chloroform/methanol is by (18:2,17:3,16:4,15:5,13:7,0:20, v/v) wash-out successively, finally obtains 10 fragments according to thin-layer chromatography colour developing merging; The elution requirement of rattletop chloroform extract be chloroform/methanol by (19:1-18:2-17:3-16:4-10:10-0:20, v/v) wash-out successively, obtain 4 fragments according to thin-layer chromatography colour developing merging.By carrying out the detection of DPPH radical scavenging activity to the Radix Astragali 10 fragments and rattletop 4 fragments, filter out 2 of the Radix Astragali, 3,4,5 fragments and rattletop fragment 1 carry out further purifying and analysis.
(3) screening of the composition of potential collaborative scavenging free radicals in the Radix Astragali fragment 2,3,4,5 obtained in (2) and rattletop fragment 1: Radix Astragali fragment 2,4 adopts the method for recrystallizing methanol to carry out purifying, Radix Astragali fragment 3,5 and rattletop fragment 1 adopted the method repeatedly crossing SephadexLH-20 post to carry out purifying.By 2 after Radix Astragali purifying, 3,4,5 fragments combine (two medicines under the condition that concentration is identical by volume 1:1 combine) respectively and evaluate it and collaboratively remove DPPH free radical effect with the fragment 1 after rattletop purifying, filter out component in Radix Astragali fragment 2,4 and rattletop fragment 1 as potential collaborative removing DPPH free radical composition.
(4) qualification of potential collaborative composition in the Radix Astragali fragment 2,4 obtained in (3) and rattletop fragment 1: utilize ultraviolet full wavelength scanner, HPLC-MS/MS determines molecular weight of material and the methods such as (HPLC) that contrasts with standard substance is identified the composition in Radix Astragali fragment 2,4 and rattletop fragment 1, qualification result is: two main peaks in Radix Astragali fragment 2 are respectively calycosin and onocerin, Radix Astragali fragment 4 main component is calycosin, and in rattletop fragment 1, two main peaks are respectively forulic acid and isoferulic acid.
(5) confirmatory test of the potential collaborative composition identified in (4): the DPPH radical scavenging activity of the standard substance of mensuration calycosin, onocerin, forulic acid, isoferulic acid, filter out calycosin and forulic acid, isoferulic acid combine, evaluate its collaborative scavenging ability of DPPH free radical, when finding calycosin and isoferulic acid combination, good synergistic function (table 1) can be shown.
(6) dosage when calycosin combines with isoferulic acid-cooperative effect Relational Data Mining: by calycosin methanol solution identical for concentration and isoferulic acid methanol solution difference 3:1 by volume; 2:1; 1:1; 1:2; 1:3 combines, and evaluates its collaborative ability removing DPPH free radical (0.1mmol/L), finds that the calycosin methanol solution of same concentrations and isoferulic acid methanol solution show the strongest synergistic function (table 2) under the condition of volume ratio 1:1.
Claims (1)
1. the composition of the calycosin methanol solution of same concentrations and isoferulic acid methanol solution 1:1 is by volume manufacturing the application of removing in DPPH free radical medicine, it is characterized in that free radical scavenging activity is 2-75%.
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| CN112391169A (en) * | 2020-11-04 | 2021-02-23 | 厦门华天华电子有限公司 | Oxidation-resistant mixed liquid and FPC (flexible printed circuit) etching method for reducing oxidation under film |
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| CN1850174A (en) * | 2006-02-22 | 2006-10-25 | 天津大学 | Method for preparing Rhizoma cimicifugae formula granules |
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| Title |
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| 升麻中阿魏酸和异阿魏酸的提取工艺研究;王剑光;《中国中医药科技》;20070930;第14卷(第5期);全文 * |
| 黄芪升麻药对抗氧化活性及协同作用的研究;徐燕;《中国优秀硕士论文全库》;20111213;第29页3.2.1和第43页第1段 * |
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