CN110483541A - A kind of isopentene group flavone compound and its preparation method and application - Google Patents

A kind of isopentene group flavone compound and its preparation method and application Download PDF

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CN110483541A
CN110483541A CN201910829693.8A CN201910829693A CN110483541A CN 110483541 A CN110483541 A CN 110483541A CN 201910829693 A CN201910829693 A CN 201910829693A CN 110483541 A CN110483541 A CN 110483541A
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fraction
volume ratio
silica gel
petroleum ether
component
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CN110483541B (en
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孙彦君
冯卫生
陈辉
张艳丽
弓建红
高美玲
陈豪杰
赵晨
韩瑞杰
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Henan University of Traditional Chinese Medicine HUTCM
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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L2/00Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/42Preservation of non-alcoholic beverages
    • A23L2/44Preservation of non-alcoholic beverages by adding preservatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/40Separation, e.g. from natural material; Purification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04Ortho-condensed systems

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  • Medicines Containing Plant Substances (AREA)
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Abstract

The present invention relates to isopentene group flavone compounds and its preparation method and application, it can effectively solve the problems, such as the preparation of isopentene group flavone compound and prepare antioxidant, the isopentene group flavone compound is the Chinese podophyllum root ketone Q(sinoflavonoids Q I extracted from Himalayan mayapple fruit), Chinese podophyllum root ketone R(sinoflavonoids R II), Chinese podophyllum root ketone S(sinoflavonoids S III), Chinese podophyllum root ketone T(sinoflavonoids T IV), it can be used for preparing the antioxidant of food or beverage, abundant raw material, preparation method is easy to operate, economic and social benefit is significant.

Description

A kind of isopentene group flavone compound and its preparation method and application
Technical field
The present invention relates to medicine, especially a kind of isopentene group flavone compound and its system with antioxidant activity Preparation Method and application.
Background technique
The active oxygen radical that oxidative stress refers to body tissue or generates into the cell has been more than that original oxygen radical makes With ability or Scavenging activity, redox equilibrium is destroyed, so as to cause the active oxygen radical excessively accumulated is generated in vivo And its relevant metabolite causes certain detrimental effect to body, thus certain pathological state is presented.Oxidative stress quilt Be considered the reason of leading to many degenerative diseases, as cancer, chronic inflammation, cardiovascular disease, neurogenic disease, diabetes, Alzheimer's disease and Parkinson's disease etc..Thus by inhibiting the damage of oxidative stress class to become disease relevant to treatment oxidative stress One of the important channel of disease.At the same time, in food, the oxidation of nutriment can cause food quality to decline, or even can also Cause the body of intake person that disease occurs.Therefore, finding safe antioxidant is always grinding for pharmacy and nutrition worker Study carefully hot spot.
Himalayan mayapple fruit is the drying of Berberidaceae Sinopodophyllum plant Podophyllum emodi var chinense Sinopodophyllum emodi (Wall.) Ying. Ripening fruits.Podophyllum emodi var chinense is a kind of medicinal plant with long history, just on the books in ancient times Shennong's Herbal: big poison is killed, Treat cough larynx disease, the tired sense of ailment said due to cold or exposure loses that soul is absurd to see.Do not enter soup.How on the books later history tree is also, is mainly used for Huoxue San " Knot, dispelling wind and eliminating dampness, worm snake bite, bruise, heart stomachache, cough due to wind-cold evil, irregular menstruation, Aconitum Szechenyianum Gay poisoning, rheumatalgia and gas The diseases such as pipe inflammation.Than wide, China is mainly distributed on Sichuan, Qinghai, Tibet, Gansu, Shaanxi for Podophyllum emodi var chinense distribution.Himalayan mayapple fruit is as biography System Tibetan medicine has long medicinal history first recorded in " moon king's medicine examine ".Chemical constitution study shows to mainly contain lignanoid and Huang Ketone compounds, wherein isopentene group flavone compound is representative active constituent in Himalayan mayapple fruit, is had important and wide General bioactivity is for example anti-oxidant, antitumor, anti-inflammatory, antibacterial, anti-osteoporosis, prevents senile dementia, anti-diabetic, heart and brain blood Protection of pipe, estrogen-like etc..But be related to that there is oxidation resistant isopentene group flavone compound and its bioactivity, so far for It only there are no patent or document report
Summary of the invention
For above situation, for the defect for overcoming the prior art, the purpose of the present invention is just to provide a kind of isopentene group Flavone compound and its preparation method and application, preparation and the preparation that can effectively solve isopentene group flavone compound are anti- The problem of oxidant.
The technical solution that the present invention solves is that a kind of isopentene group flavone compound is extracted from Himalayan mayapple fruit Chinese podophyllum root ketone Q (sinoflavonoids Q I), Chinese podophyllum root ketone R (sinoflavonoids R II), Chinese podophyllum root ketone S (sinoflavonoids S III), Chinese podophyllum root ketone T (sinoflavonoids T IV), molecular structural formula is respectively as follows:
Preparation method is:
Using 6-9kg of Himalayan mayapple fruit medicinal material as raw material, heated with 2-5 times of raw material weights, the ethyl alcohol that volumetric concentration is 75%-95% Refluxing extraction 3 times, Extracting temperature is 90-95 DEG C, and each extraction time is 1.5-2 hours, and ethyl alcohol is recovered under reduced pressure and obtains medicinal extract shape second Alcohol extracting thing is suspended in the distilled water of 2-3.2L, successively respectively extracts 3 with petroleum ether, methylene chloride, ethyl acetate, n-butanol Secondary, 2-3.2L, time are 1.5-2 hours every time;Ethyl acetate fraction is separated through silica gel column chromatography, successively uses volume ratio For the petroleum of 100:0,100:5,100:7,100:10,100:30,100:50,100:70,100:100,100:200,0:100 Ether-acetone mixed solvent system carries out gradient elution, 9.1-13L eluents of each gradient, and flow velocity is 10-15mL/min, often 350-500ml volumes are a fraction, collect 260 fractions, each fraction is tested and analyzed through silica gel thin-layer chromatography, thin with GF254 Laminate, respectively using the methylene chloride-methanol of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 as solvent, with volume As color developing agent, 105 DEG C of 3-5min of heating are closed sulfuric acid-ethanol solution than 10:90 respectively according to thin-layer chromatography testing result And fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-132, fraction 133-144, fraction 145- 157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196-204, Fraction 205-208, fraction 209-234, fraction 235-260, obtain component Fr.1-Fr.16;By component Fr.8 through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity are 50-70mL/h, and every 8-12mL is a fraction, collects 43 fractions, each Fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, using methylene chloride-acetone of volume ratio 5:3 as expansion Agent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating are detected according to thin-layer chromatography and are tied Fruit, respectively merge fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43, obtain 5 inferior component Fr.8-1, Fr.8-2,Fr.8-3,Fr.8-4,Fr.8-5;Inferior component Fr.8-4 is purified through preparative high performance liquid chromatography, chromatographic column YMC- Pack ODS-A, then with volume ratio be the Methanol+Water system elutions of 72:28, flow velocity 7mL/min is collected and is retained Time is that the chromatographic peak of 36min obtains chemical compounds I;By component Fr.9 through silica gel column chromatography, the petroleum ether-the third of volume ratio 100:30 The elution of ketone mixed solvent, every 10-15mL are a fraction, collect the fraction containing compounds Ⅳ and obtain compounds Ⅳ;By component Fr.11 is through silica gel column chromatography, petroleum ether-acetone mixed solvent system of volume ratio 100:7,100:10,100:15,100:20 Elution, 50-80mL eluents of each gradient, every 5-8mL are a fraction, collect 40 fractions, each fraction is through silica gel thin-layer Chromatography tests and analyzes, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with volume ratio 10: 90 sulfuric acid-ethanol solution merges fraction according to thin-layer chromatography testing result as color developing agent, 105 DEG C of 3-5min of heating respectively 1-8, fraction 9-15, fraction 16-31, fraction 32-40, obtain 4 inferior components Fr.11-1, Fr.11-2, Fr.11-3, Fr.11- 4;Inferior component Fr.11-4 is purified through preparative high performance liquid chromatography, is the Methanol+Water system of 80:20 with volume ratio Elution, chromatographic column are YMC-Pack ODS-A, flow velocity 7mL/min, collect the chromatographic peak that retention time is 69min Close object III;By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution is eluted, and every 3-5mL is One fraction collects the fraction containing compound ii and obtains compound ii.
Novel isopentene group flavone compound Chinese podophyllum root ketone Q prepared by the present invention with antioxidant activity (sinoflavonoid Q I), Chinese podophyllum root ketone R (sinoflavonoid R II), Chinese podophyllum root ketone S (sinoflavonoid S III), Chinese podophyllum root ketone T (sinoflavonoid T IV), can be used for preparing the antioxidant of food or beverage, abundant raw material, preparation side Method is easy to operate, and economic and social benefit is significant.
Detailed description of the invention
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of the compounds of this invention I.
Fig. 2 is the carbon-13 nmr spectra figure of the compounds of this invention I.
Fig. 3 is the HMBC spectrogram of the compounds of this invention I.
Fig. 4 is the hsqc spectrum figure of the compounds of this invention I.
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram of the compounds of this invention II.
Fig. 6 is the carbon-13 nmr spectra figure of the compounds of this invention II.
Fig. 7 is the HMBC spectrogram of the compounds of this invention II.
Fig. 8 is the hsqc spectrum figure of the compounds of this invention II.
Fig. 9 is the hydrogen nuclear magnetic resonance spectrogram of the compounds of this invention III.
Figure 10 is the carbon-13 nmr spectra figure of the compounds of this invention III.
Figure 11 is the HMBC spectrogram of the compounds of this invention III.
Figure 12 is the hsqc spectrum figure of the compounds of this invention III.
Figure 13 is the hydrogen nuclear magnetic resonance spectrogram of the compounds of this invention IV.
Figure 14 is the carbon-13 nmr spectra figure of the compounds of this invention IV.
Figure 15 is the HMBC spectrogram of the compounds of this invention IV.
Figure 16 is the hsqc spectrum figure of the compounds of this invention IV.
Specific embodiment
It elaborates with reference to embodiments with concrete condition to a specific embodiment of the invention.
The present invention can be provided in the specific implementation by following embodiment.
Embodiment 1
A kind of preparation method of isopentene group flavone compound of the present invention, using Himalayan mayapple fruit medicinal material 9kg as raw material, with 18L, volumetric concentration are 95% ethyl alcohol heating and refluxing extraction 3 times, and Extracting temperature is 95 DEG C, and each extraction time is 1.5 hours, are subtracted Receipts ethyl alcohol is pushed back, medicinal extract shape ethanol extract is obtained, is suspended in the distilled water of 3.2L, successively with petroleum ether, methylene chloride, acetic acid Ethyl ester, n-butanol respectively extract 3 times, each 3.2L, and the time is 1.5 hours;By Ethyl acetate fraction through at the beginning of silica gel column chromatography Step separation, be successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50,100:70,100:100, The petroleum ether of 100:200,0:100-acetone mixed solvent system carry out gradient elution, each gradient 13L eluent, and flow velocity is 15mL/min, every 500ml volume are a fraction, collect 260 fractions, each fraction is tested and analyzed through silica gel thin-layer chromatography, use GF254 lamellae, respectively using the methylene chloride-methanol of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 as solvent, Using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography testing result, Merge fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-132, fraction 133-144, stream respectively Part 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260 obtain-Fr.16 components of Fr.1;Component Fr.8 is passed through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 70mL/h, every 12mL are a fraction, collect 43 fractions, respectively A fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, using the dichloromethane-acetone of volume ratio 5:3 as expansion Agent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating are detected according to thin-layer chromatography and are tied Fruit, respectively merge fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43, obtain 5 inferior component Fr.8-1, Fr.8-2,Fr.8-3,Fr.8-4,Fr.8-5;Inferior component Fr.8-4 is purified through preparative high performance liquid chromatography, chromatographic column YMC- Pack ODS-A, then with volume ratio be the Methanol+Water system elutions of 72:28, flow velocity 7mL/min is collected and is retained Time is that the chromatographic peak of 36min obtains chemical compounds I;By component Fr.9 through silica gel column chromatography, the petroleum ether-the third of volume ratio 100:30 The elution of ketone mixed solvent, every 15mL are a fraction, collect the fraction containing compounds Ⅳ and obtain compounds Ⅳ;By component Fr.11 is through silica gel column chromatography, petroleum ether-acetone mixed solvent system of volume ratio 100:7,100:10,100:15,100:20 Elution, each gradient 80mL eluent, every 8mL are a fraction, collect 40 fractions, each fraction is examined through silica gel thin-layer chromatography Analysis is surveyed, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with the sulphur of volume ratio 10:90 Acid-ethanol solution merges fraction 1-8, stream according to thin-layer chromatography testing result as color developing agent, 105 DEG C of 3-5min of heating respectively Part 9-15, fraction 16-31, fraction 32-40, obtain 4 inferior components Fr.11-1, Fr.11-2, Fr.11-3, Fr.11-4;Subgroup Part Fr.11-4 is purified through preparative high performance liquid chromatography, is the Methanol+Water system elutions of 80:20, color with volume ratio Spectrum column is YMC-Pack ODS-A, flow velocity 7mL/min, collects the chromatographic peak that retention time is 69min and obtains compound III; By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution elution, every 5mL is a fraction, is received Fraction of the collection containing compound ii obtains compound ii.
Embodiment 2
A kind of preparation method of isopentene group flavone compound of the present invention, using Himalayan mayapple fruit medicinal material 6kg as raw material, with 30L, volumetric concentration are 75% ethyl alcohol heating and refluxing extraction 3 times, and Extracting temperature is 90 DEG C, and each extraction time is 2 hours, decompression Ethyl alcohol is recycled, medicinal extract shape ethanol extract is obtained, is suspended in the distilled water of 2L, successively with petroleum ether, methylene chloride, acetic acid second Ester, n-butanol respectively extract 3 times, each 2L, and the time is 2 hours;By Ethyl acetate fraction through silica gel column chromatography initial gross separation, Be successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50,100:70,100:100,100:200, The petroleum ether of 0:100-acetone mixed solvent system carries out gradient elution, each gradient 9.1L eluent, flow velocity 10mL/ Min, every 350ml volume are a fraction, collect 260 fractions, each fraction is tested and analyzed through silica gel thin-layer chromatography, use GF254 Lamellae, respectively using the methylene chloride-methanol of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 as solvent, with body Sulfuric acid-ethanol solution of the product than 10:90 is as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography testing result, difference Merge fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-132, fraction 133-144, fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196- 204, fraction 205-208, fraction 209-234, fraction 235-260 obtain-Fr.16 components of Fr.1;Component Fr.8 is passed through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 50mL/h, every 8mL are a fraction, collect 43 fractions, respectively A fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, using the dichloromethane-acetone of volume ratio 5:3 as expansion Agent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating are detected according to thin-layer chromatography and are tied Fruit, respectively merge fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43, obtain 5 inferior component Fr.8-1, Fr.8-2,Fr.8-3,Fr.8-4,Fr.8-5;Inferior component Fr.8-4 is purified through preparative high performance liquid chromatography, chromatographic column YMC- Pack ODS-A, then eluted with volume ratio for the methanol-water mixed solution of 72:28, flow velocity 7mL/min collects retention time Chemical compounds I is obtained for the chromatographic peak of 36min;By component Fr.9 through silica gel column chromatography, petroleum ether-acetone of volume ratio 100:30 is mixed Bonding solvent elution, every 10mL are a fraction, collect the fraction containing compounds Ⅳ and obtain compounds Ⅳ;Component Fr.11 is passed through Silica gel column chromatography, petroleum ether-acetone mixed solvent system elutions of volume ratio 100:7,100:10,100:15,100:20 are each Gradient 5mL eluent, every 5mL are a fraction, collect 40 fractions, and each fraction is tested and analyzed through silica gel thin-layer chromatography, are used GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with sulfuric acid-ethyl alcohol of volume ratio 10:90 Solution is as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography testing result, merge respectively fraction 1-8, fraction 9-15, Fraction 16-31, fraction 32-40 obtain 4 inferior components Fr.11-1, Fr.11-2, Fr.11-3, Fr.11-4;Inferior component Fr.11-4 is purified through preparative high performance liquid chromatography, is the Methanol+Water system elutions of 80:20, chromatography with volume ratio Column is YMC-Pack ODS-A, flow velocity 7mL/min, collects the chromatographic peak that retention time is 69min and obtains compound III;By group Divide Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution elution, every 3mL is a fraction, and collection contains There is the fraction of compound ii to obtain compound ii.
Embodiment 3
A kind of preparation method of isopentene group flavone compound of the present invention, using Himalayan mayapple fruit medicinal material 8kg as raw material, with 24L, volumetric concentration are 85% ethyl alcohol heating and refluxing extraction 3 times, and Extracting temperature is 92 DEG C, and each extraction time is 1.5 hours, are subtracted Receipts ethyl alcohol is pushed back, medicinal extract shape ethanol extract is obtained, is suspended in the distilled water of 2.8L, successively with petroleum ether, methylene chloride, acetic acid Ethyl ester, n-butanol respectively extract 3 times, each 2.8L, and the time is 1.5 hours;By Ethyl acetate fraction through at the beginning of silica gel column chromatography Step separation, be successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50,100:70,100:100, The petroleum ether of 100:200,0:100-acetone mixed solvent system carry out gradient elution, each gradient 11.7L eluent, flow velocity For 13mLmin-1, every 450ml volume is a fraction, collect 260 fractions, each fraction is tested and analyzed through silica gel thin-layer chromatography, With GF254 lamellae, respectively using the methylene chloride-methanol of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 as expansion Agent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating are detected according to thin-layer chromatography and are tied Fruit, respectively merge fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-132, fraction 133-144, Fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260 obtain-Fr.16 components of Fr.1;Component Fr.8 is passed through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 65mL/h, every 10mL are a fraction, collect 43 fractions, respectively A fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, using the dichloromethane-acetone of volume ratio 5:3 as exhibition Agent is opened, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating are detected according to thin-layer chromatography As a result, merging fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43 respectively, 5 inferior component Fr.8- are obtained 1,Fr.8-2,Fr.8-3,Fr.8-4,Fr.8-5;Inferior component Fr.8-4 is purified through preparative high performance liquid chromatography, and chromatographic column is YMC-Pack ODS-A, then with volume ratio be the Methanol+Water system elutions of 72:28, flow velocity 7mL/min is collected Retention time is that the chromatographic peak of 36min obtains chemical compounds I;By component Fr.9 through silica gel column chromatography, the petroleum of volume ratio 100:30 Ether-acetone mixed solvent elution, every 12mL are a fraction, collect the fraction containing compounds Ⅳ and obtain compounds Ⅳ;By group Divide Fr.11 through silica gel column chromatography, petroleum ether-acetone mixed solvent system of volume ratio 100:7,100:10,100:15,100:20 System elution, each gradient 75mL eluent, every 7.5mL are a fraction, collect 40 fractions, each fraction is through silica gel thin-layer Chromatography tests and analyzes, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with volume ratio Sulfuric acid-ethanol solution of 10:90 merges as color developing agent, 105 DEG C of 3-5min of heating according to thin-layer chromatography testing result respectively Fraction 1-8, fraction 9-15, fraction 16-31, fraction 32-40, obtain 4 inferior component Fr.11-1, Fr.11-2, Fr.11-3, Fr.11-4;Inferior component Fr.11-4 is purified through preparative high performance liquid chromatography, molten for the methanol-water mixing of 80:20 with volume ratio Agent system elutions, chromatographic column are YMC-Pack ODS-A, flow velocity 7mL/min, collect the chromatographic peak that retention time is 69min and obtain To compound III;By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution is eluted, often 4.5mL is a fraction, collects the fraction containing compound ii and obtains compound ii.
Embodiment 4
In specific implementation, the novel isopentene group flavone compound with antioxidant activity can also be by small by the present invention Leaf lotus medicinal material 7kg is raw material, and with 28L, volumetric concentration for 75% ethyl alcohol heating and refluxing extraction 3 times, Extracting temperature is 90 DEG C, often Secondary extraction time be 2 hours, ethyl alcohol is recovered under reduced pressure, obtains medicinal extract shape ethanol extract, is suspended in the distilled water of 2.4L, successively with Petroleum ether, methylene chloride, ethyl acetate, n-butanol respectively extract 3 times, each 2.4L, and the time is 2 hours;Ethyl acetate is extracted Position is successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100 through silica gel column chromatography initial gross separation: 50, the petroleum ether of 100:70,100:100,100:200,0:100-acetone mixed solvent system carry out gradient elution, Mei Yiti Degree 10.4L eluent, flow velocity 12mLmin-1, every 400ml volume is a fraction, collects 260 fractions, each fraction warp Silica gel thin-layer chromatography tests and analyzes, with GF254 lamellae, respectively with petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 Methylene chloride-methanol is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of heating 3- 5min, according to thin-layer chromatography testing result, merge respectively fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, Fraction 116-132, fraction 133-144, fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260, obtain - Fr.16 components of Fr.1;By component Fr.8 through Sephadex LH-20 gel column chromatography, methanol is eluted, flow velocity 55mL/h, Every 9mL is a fraction, collects 43 fractions, and each fraction tests and analyzes through silica gel thin-layer chromatography, with GF254 lamellae, with body Dichloromethane-acetone of the product than 5:3 is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C 3-5min of heating merge fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-according to thin-layer chromatography testing result respectively 33, fraction 34-43 obtain 5 inferior components Fr.8-1, Fr.8-2, Fr.8-3, Fr.8-4, Fr.8-5;Inferior component Fr.8-4 warp Preparative high-performance liquid chromatographic, chromatographic column is YMC-Pack ODS-A, then is washed with volume ratio for the methanol-water mixed solution of 72:28 De-, flow velocity 7mL/min collects the chromatographic peak that retention time is 36min and obtains chemical compounds I;By component Fr.9 through silicagel column color Spectrum, petroleum ether-acetone mixed solvent elution of volume ratio 100:30, every 11mL is a fraction, collects the stream containing compounds Ⅳ Part obtains compounds Ⅳ;By component Fr.11 through silica gel column chromatography, volume ratio 100:7,100:10,100:15,100:20's Petroleum ether-acetone mixed solvent system elutions, each gradient 70mL eluent, every 7mL are a fraction, collect 40 fractions, Each fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, is made respectively with the petroleum ether of volume ratio 5:4-acetone For solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography Testing result, respectively merge fraction 1-8, fraction 9-15, fraction 16-31, fraction 32-40, obtain 4 Arius part Fr.11-1, Fr.11-2,Fr.11-3,Fr.11-4;Arius part Fr.11-4 is purified through preparative high-performance liquid chromatographic, is 80:20 with volume ratio Methanol+Water elution, chromatographic column be YMC-Pack ODS-A, flow velocity 7mL/min, collect retention time be The chromatographic peak of 69min obtains compound III;By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixing Solution elution, every 4mL are a fraction, collect the fraction containing compound ii and obtain compound ii.
The method of the present invention is reliable and stable, easy to operate, embodiment 1-4 products therefrom through UV, IR, NMR spectrum (1H- NMR、13C-NMR, HSQC, HMBC) and high resolution mass spectrum (HR-ESI-MS) spectral technique be accredited as novel isopentene group flavones Class compound Chinese podophyllum root ketone Q (sinoflavonoid Q), Chinese podophyllum root ketone R (sinoflavonoid R), Chinese podophyllum root ketone S (sinoflavonoid S), Chinese podophyllum root ketone T (sinoflavonoid T) has Scavenging activity to DPPH free radical.Related money Expect as follows:
One, the identification of compound
Chemical compounds I, yellow powder, hydrochloric acid-magnesium powder reaction are positive, and prompt may be flavone compound.HR-ESI-MS Provide quasi-molecular ion peak m/z 453.1910 [M ﹢ H]+(calcd for C26H29O7, 453.1913, determine that molecular formula is C26H28O7。 IR(KBr,cm-1) show that the compound has free hydroxyl group (3354cm-1), associate carbonyl (1659cm-1), phenyl ring (1611 cm-1).UV (λ max) shows that the compound has flavones ol skeleton (262,321nm).1H NMR(500MHz,DMSO- d6) display two groups of aromatic Coupling System signal δ 6.35 (1H, s), 6.76 (1H, d, J=8.3Hz), 6.74 (1H, d, J= 8.3 Hz), it is respectively belonging to the A ring and B ring of flavones parent nucleus, one five is respectively present in prompting structure and is replaced and 1,2,3,4- tetra- Substituted benzene ring structural unit.By 2 groups of methene proton signal δ 3.21 (2H, d, J=7.1Hz), 3.24 (2H, d, J=7.3Hz), Four methyl proton signal δ 1.71 (3H, s), 1.61 (3H, s), 1.34 (3H, s), 1.49 (3H, the s) being connected with quaternary carbon, two A alkene Hydrogen Proton δ 5.16 (1H, t, J=7.1), 5.03 (1H, t, J=7.3), there are 2 isopentene groups in prompting structure.1 The methoxy proton signal δ 3.56 (3H, s) being connected with olefinic carbon.Five phenolic hydroxyl group proton δ 12.90 (1H, s), 10.81 (1H, s), 9.87 (1H, s), 8.52 (1H, s), wherein δ 12.90 (1H, s) is the 5 phenolic hydroxyl group proton signals to associate with 4 carbonyls.13C NMR(125 MHz,DMSO-d6) display contains 26 carbon atoms, in addition to 2 groups of isopentene group carbon signal δ 21.4,122.6, 131.1, except 18.1,25.9,26.2,123.3,130.6,17.8,25.7,12 fragrant carbon signals, 1 carbonyl are given Carbon signal δ 178.5, two olefinic carbon signal δ 159.6,139.0 being connected with oxygen, the above carbon modal data further demonstrate that chemical compounds I For isopentene group flavones 01 derivatives.HMBC spectrum in, by methene proton signal δ 3.21 (2H, d, J=7.1Hz, H-1 ") with The long-range correlation of δ 158.5 (C-5), 111.1 (C-6), 162.3 (C-7), δ 3.24 (2H, d, J=7.3Hz, H-1 " ') and δ The long-range correlation of 123.2 (C-1 '), 128.2 (C-2 '), 143.7 (C-3 ') show that two isopentene groups are connected to flavones The position C-6 and C-2 ' of parent nucleus.It is remotely related by δ 3.56 (3H, s) and the HMBC of δ 139.0 (C-3), show the methoxy not belonged to Base is connected to C-3.By chemical compounds I1H NMR、13C NMR signal is belonged to by HSQC, HMBC spectrum (see Table 1). Therefore chemical compounds I structure be 6,2 '-di (3-methyl-2-butenyl) -5,7,3 ', 4 '-tetrahydroxy-3- Methoxyflavone is named as Chinese podophyllum root ketone Q (sinoflavonoid Q).
Table 1.NMR(500MHz,DMSO-d6)assignments for I.
Compound ii, yellow powder, hydrochloric acid-magnesium powder reaction are positive, and prompt may be flavone compound.HR-ESI- MS provides quasi-molecular ion peak m/z 453.1910 [M ﹢ H]+(calcd for C26H29O7, 453.1913), determine that molecular formula is C26H28O7。IR(KBr,cm-1) show that the compound has free hydroxyl group (3374cm-1), associate carbonyl (1650cm-1), phenyl ring (1597cm-1).UV (λ max) shows that the compound has flavones ol skeleton (262,321nm).1H NMR(500MHz, DMSO- d6) two groups of aromatic Coupling System signal δ 6.28 (1H, s) of display, 6.68 (1H, d, J=8.2Hz), 6.72 (1H, d, J= 8.2Hz), it is respectively belonging to the A ring and B ring of flavones parent nucleus, one five is respectively present in prompting structure and is replaced and 1,2,3,4- tetra- Substituted benzene ring structural unit.By 2 groups of methene proton signal δ 2.54 (2H, t, J=6.8Hz), 1.74 (2H, t, J=6.8Hz), Methyl proton signal δ 1.30 (6H, s) on two quaternary carbons, there are 12,2- dimethyl dihydropyran rings in prompting structure.By 1 A methene proton signal δ 3.21 (2H, d, J=6.9Hz), two be connected with quaternary carbon methyl proton signal δ 1.34 (3H, S), 1.50 (3H, s), an alkene Hydrogen Proton δ 5.04 (1H, t, J=6.9), there are 1 isopentene groups in prompting structure.1 with The connected methoxy proton signal δ 3.48 (3H, s) of olefinic carbon.Three phenolic hydroxyl group signal δ 10.60 (1H, s), 9.75 (1H, s), 8.46 (1H, s), wherein δ 10.60 (1H, s) is 7 phenolic hydroxyl group proton signals.13C NMR(125MHz,DMSO-d6) display contain There are 26 carbon atoms, in addition to 1 group of 2,2- dimethyl-dihydro pyranyl δ 16.7,30.8,74.7,26.4 (× 2), one group of isoamyl Alkenyl δ 26.0,122.9,129.9,17.4,25.4, δ 59.4 except a methoxyl group, give 12 fragrant carbon signals, and 1 Carbonyl carbon signals δ 172.0, two company oxygen olefinic carbon signal δ 155.1,140.6, the above carbon modal data further demonstrates that compound ii For isopentene group flavones 01 derivatives.HMBC spectrum in, by methene proton signal δ 2.54 (2H, t, J=6.8Hz, H-1 ") with The long-range correlation of δ 154.6 (C-5), 105.0 (C-6), 159.8 (C-7), in conjunction with 7 phenolic hydroxyl group signal δ 10.60 (1H, s) In the presence of, show dihydropyran ring and flavones parent nucleus C-5 and C-6 it is parallel and.By methene proton signal δ 3.21 (2H, t, J= 6.9Hz, H-1 " ') to δ 121.8 (C-1 '), 127.6 (C-2 '), 143.2 (C-3 ') it is long-range related, show isopentene group connect It connects in 2 ' positions.It is remotely related by δ 3.56 (3H, s) and the HMBC of δ 140.6 (C-3), show that the methoxyl group not belonged to is connected to C-3.By compound ii1H NMR、13C NMR signal is belonged to by HSQC, HMBC spectrum (see Table 2).Therefore change Close object II structure be 5,6- (2,2-dimethyldihydropyrano) -2 '-(3-methyl-2-butenyl) -7,3 ', 4 '-trihydroxy-3-methoxyflavone are named as Chinese podophyllum root ketone R (sinoflavonoid R).
Table 2.NMR(500MHz,DMSO-d6)assignments forⅡ.
Compound III, yellow powder, hydrochloric acid-magnesium powder reaction are positive, and prompt may be flavone compound.HR-ESI- MS provides quasi-molecular ion peak m/z 453.1912 [M ﹢ H]+(calcd for C26H29O7, 453.1913), determine that molecular formula is C26H28O7。IR(KBr,cm-1) show that the compound has free hydroxyl group (3524cm-1), associate carbonyl (1651cm-1), phenyl ring (1604cm-1).UV (λ max) shows that the compound has flavones ol skeleton (261,325nm).1H NMR(500MHz, DMSO- d6) two groups of aromatic Coupling System signal δ 6.34 (1H, s) of display, 6.73 (1H, d, J=8.4Hz), 6.76 (1H, d, J= 8.4Hz), it is respectively belonging to the A ring and B ring of flavones parent nucleus, one five is respectively present in prompting structure and is replaced and 1,2,3,4- tetra- Substituted benzene ring structural unit.By 2 groups of methene proton signal δ 2.62 (2H, t, J=6.7Hz), 1.81 (2H, t, J=6.7Hz), Methyl proton signal δ 1.30 (6H, s) on two quaternary carbons, there are 12,2- dimethyl dihydropyran rings in prompting structure.By 1 A methene proton signal δ 3.25 (2H, d, J=6.9Hz), two be connected with quaternary carbon methyl proton signal δ 1.30 (3H, S), 1.45 (3H, s), an alkene Hydrogen Proton δ 5.00 (1H, t, J=6.9Hz), there are 1 isopentene groups in prompting structure.1 The methoxy proton signal δ 3.56 (3H, s) being connected with olefinic carbon.Three phenolic hydroxyl group signal δ 13.00 (1H, s), 9.86 (1H, s), 8.56 (1H, s), wherein δ 13.00 (1H, s) is the 5 phenolic hydroxyl group proton signals to associate with 4 carbonyls.13C NMR(125MHz, DMSO-d6) display contain 26 carbon atoms, in addition to 1 group of 2,2- dimethyl dihydro pyranyl δ 15.7,30.9,76.2,26.3 (× 2), one group of isopentene group δ 25.7,122.8,130.2,17.4,25.4, δ 59.9 except a methoxyl group, gives 12 fragrance Carbon signal, 1 carbonyl carbon signals δ 178.2, two company oxygen olefinic carbon signal δ 159.7,138.5, the above further table of carbon modal data Bright compound III is isopentene group flavones 01 derivatives.In HMBC spectrum, by methene proton signal δ 2.62 (2H, t, J= 6.7Hz, H-1 ") to δ 104.4 (C-6), 159.8 (C-7), 94.4 (C-8) it is long-range related, in conjunction with 5 phenolic hydroxyl group signal δ The presence of 13.00 (1H, s), show 2,2- dimethyl dihydropyran ring and flavones parent nucleus C-6 and C-7 it is parallel and.By methylene Proton signal δ 3.25 (2H, d, J=6.9Hz, H-1 " ') and δ 121.1 (C-1 '), 127.8 (C-2 '), 143.3 (C-3 ') It is long-range related, show that isopentene group is connected to 2 ' positions.Remotely related, the table by δ 3.56 (3H, s) and the HMBC of δ 138.5 (C-3) The bright methoxyl group not belonged to is connected to C-3.By compound III1H NMR、13C NMR signal is carried out by HSQC, HMBC spectrum Belong to (see Table 3).Therefore the structure of compound III is 6,7- (2,2-dimethyldihydropyrano) -2 '-(3- Methyl-2-butenyl) -5,3 ', 4 '-trihydroxy-3-methoxyflavone are named as Chinese podophyllum root ketone S (sinoflavonoid S)。
Table 3.NMR(500MHz,DMSO-d6)assignments forⅢ.
Compounds Ⅳ, yellow powder, hydrochloric acid-magnesium powder reaction are positive, and prompt may be flavone compound.HR-ESI- MS provides quasi-molecular ion peak m/z 385.1262 [M ﹢ H]+(calcd for C21H21O7, 385.1287), determine that molecular formula is C21H20O7。IR(KBr,cm-1) show that the compound has free hydroxyl group (3421cm-1), association carbonyl (1655cm-1), phenyl ring (1617cm-1).UV (λ max) shows that compound tool has flavones ol skeleton (256,345nm).1H NMR(500MHz, DMSO-d6) display two groups of aromatic Coupling System signal δ 6.40 (1H, s), 7.46 (1H, d, J=2.2Hz), 6.86 (1H, D, J=8.5Hz), 7.35 (1H, dd, J=8.5,2.2Hz), the A ring and B ring of flavones parent nucleus are respectively belonging to, in prompting structure One five is respectively present to replace and 1,3,4- trisubstituted benzene ring structure.By 2 groups of methene proton signal δ 2.54 (2H, t, J= 6.7Hz), 1.72 (2H, t, J=6.7Hz), 2 methyl proton signal δ 1.30 (6H, s) being connected with quaternary carbon, shows in structure There are 1 2,2- dimethyl dihydropyran rings.1 methoxy proton signal δ 3.69 (3H, s) being connected with olefinic carbon.Two phenol Hydroxyl proton signal δ 10.67 (1H, s), 9.55 (1H, s), 9.29 (1H, s), wherein δ 10.67 (1H, s) is 7 phenolic hydroxyl group matter Subsignal.13C NMR (125MHz,DMSO-d6) display is containing 21 carbon atoms, in addition to the carbon signal δ 59.2,1 of 1 methoxyl group Except group 2,2- dimethyl dihydropyran ring carbon signal δ 16.7,30.8,74.8,26.4 (× 2), 12 aromatic carbon letters are given Number, 1 carbonyl carbon signals δ 172.1, two olefinic carbon signal δ 151.4,139.7 being connected with oxygen, the above carbon modal data is further Show that compounds Ⅳ is isopentene group flavones 01 derivatives.In HMBC spectrum, by methene proton signal δ 2.54 (2H, d, J= 6.7Hz, H-1 ") to δ 154.5 (C-5), 105.0 (C-6), 159.8 (C-7) it is long-range related, show 2,2- dimethyl dihydro Pyranoid ring is connected to C-5 and C-6.It is remotely related by δ 3.69 (3H, s) and the HMBC of δ 139.7 (C-3), show not belong to Methoxyl group be connected to C-3.By compounds Ⅳ1H NMR、13C NMR signal by HSQC, HMBC spectrum belonged to (see Table 4).Therefore compounds Ⅳ structure be 5,6- (2,2-dimethyldihydropyrano) -7,3 ', 4 ' - Trihydroxy-3-methoxyflavone is named as Chinese podophyllum root ketone T (sinoflavonoid T).
Table 4.NMR(500MHz,DMSO-d6)assignments forⅣ.
Two, antioxidant activity
With the DPPH solution of dehydrated alcohol configuration 0.1mmol/L, it is kept in dark place.By the DPPH solution of 50 μ L and it is isometric not Testing sample solution with concentration mixes well, and dark place stands 30min at room temperature, its absorbance is measured at 517nm.DPPH Free radical scavenging ability IC50Value indicates.As a result see Table 5.
- IV pair of PPH free radical scavenging ability of 5. chemical compounds I of Table
The novel isopentene group flavone compound Chinese podophyllum root ketone Q that the present invention prepares is shown by above-mentioned experiment (sinoflavonoid Q), Chinese podophyllum root ketone R (sinoflavonoid R), Chinese podophyllum root ketone S (sinoflavonoid S), peach Seven ketone T (sinoflavonoid T) have Scavenging activity to DPPH free radical, can be used as the antioxidant of food or beverage.

Claims (7)

1. a kind of isopentene group flavone compound, which is characterized in that the compound is the Chinese podophyllum root extracted from Himalayan mayapple fruit Ketone Q (sinoflavonoids Q I), Chinese podophyllum root ketone R (sinoflavonoids R II), Chinese podophyllum root ketone S (sinoflavonoids S III), Chinese podophyllum root ketone T (sinoflavonoids T IV), molecular structural formula is respectively as follows:
2. the preparation method of isopentene group flavone compound described in claim 1, which is characterized in that with Himalayan mayapple fruit medicinal material 6-9kg are raw material, with 2-5 times of raw material weights, ethyl alcohol heating and refluxing extraction 3 times that volumetric concentration is 75%-95%, Extracting temperature It is 90-95 DEG C, each extraction time is 1.5-2 hours, and ethyl alcohol is recovered under reduced pressure and obtains medicinal extract shape ethanol extract, is suspended in 2-3.2L Distilled water in, successively respectively extract 3 times with petroleum ether, methylene chloride, ethyl acetate, n-butanol, every time 2-3.2L, time be 1.5-2 hours;Ethyl acetate fraction is separated through silica gel column chromatography, be successively 100:0,100:5 with volume ratio, 100:7, The petroleum ether of 100:10,100:30,100:50,100:70,100:100,100:200,0:100-acetone mixed solvent system into Row gradient elution, 9.1-13L eluents of each gradient, flow velocity are 10-15mL/min, and every 350-500ml volume is a fraction, 260 fractions are collected, each fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, respectively with volume ratio 1:1's The methylene chloride-methanol of petroleum ether-acetone and volume ratio 5:1 are as solvent, with sulfuric acid-ethanol solution of volume ratio 10:90 As color developing agent, 105 DEG C of 3-5min of heating merge fraction 1-35, fraction 36-85, stream according to thin-layer chromatography testing result respectively Part 86-104, fraction 105-115, fraction 116-132, fraction 133-144, fraction 145-157, fraction 158-163, fraction 164- 170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, Fraction 235-260 obtains component Fr.1-Fr.16;By component Fr.8 through Sephadex LH-20 gel column chromatography, methanol is eluted, Flow velocity is 50-70mL/h, and every 8-12mL is a fraction, collects 43 fractions, and each fraction is tested and analyzed through silica gel thin-layer chromatography, It is molten with sulfuric acid-ethyl alcohol of volume ratio 10:90 using the dichloromethane-acetone of volume ratio 5:3 as solvent with GF254 lamellae Liquid merges fraction 4-7, fraction 8-13, stream according to thin-layer chromatography testing result as color developing agent, 105 DEG C of 3-5min of heating respectively Part 9-26, fraction 27-33, fraction 34-43, obtain 5 inferior components Fr.8-1, Fr.8-2, Fr.8-3, Fr.8-4, Fr.8-5;It is sub- Component Fr.8-4 is purified through preparative high performance liquid chromatography, and chromatographic column is YMC-Pack ODS-A, then with volume ratio is 72:28's Methanol+Water system elutions, flow velocity 7mL/min collect the chromatographic peak that retention time is 36min and obtain chemical compounds I; By component Fr.9 through silica gel column chromatography, petroleum ether-acetone mixed solvent elution of volume ratio 100:30, every 10-15mL is one stream Part, it collects the fraction containing compounds Ⅳ and obtains compounds Ⅳ;By component Fr.11 through silica gel column chromatography, volume ratio 100:7, The petroleum ether of 100:10,100:15,100:20-acetone mixed solvent system elutions, 50-80mL eluents of each gradient, often 5-8mL are a fraction, collect 40 fractions, and each fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, difference Using petroleum ether-acetone of volume ratio 5:4 as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C 3-5min of heating merge fraction 1-8, fraction 9-15, fraction 16-31, fraction 32-according to thin-layer chromatography testing result respectively 40, obtain 4 inferior components Fr.11-1, Fr.11-2, Fr.11-3, Fr.11-4;Inferior component Fr.11-4 is through preparative efficient liquid phase Chromatogram purification, is the Methanol+Water system elutions of 80:20 with volume ratio, and chromatographic column is YMC-Pack ODS-A, flow velocity For 7mL/min, collects the chromatographic peak that retention time is 69min and obtain compound III;By component Fr.13 through silica gel column chromatography, body Product is eluted than 100:40 petroleum ether-acetone mixed solution, and every 3-5mL is a fraction, collects the fraction containing compound ii to obtain the final product To compound ii.
3. the preparation method of isopentene group flavone compound according to claim 2, which is characterized in that with Himalayan mayapple fruit Medicinal material 9kg is raw material, and with 18L, volumetric concentration for 95% ethyl alcohol heating and refluxing extraction 3 times, Extracting temperature is 95 DEG C, is extracted every time Time is 1.5 hours, and ethyl alcohol is recovered under reduced pressure, obtains medicinal extract shape ethanol extract, is suspended in the distilled water of 3.2L, successively with petroleum Ether, methylene chloride, ethyl acetate, n-butanol respectively extract 3 times, each 3.2L, and the time is 1.5 hours;Ethyl acetate is extracted into portion Position through silica gel column chromatography initial gross separation, be successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50, The petroleum ether of 100:70,100:100,100:200,0:100-acetone mixed solvent system carry out gradient elution, and each gradient is used 13L eluent, flow velocity 15mL/min, every 500ml volume are a fraction, collect 260 fractions, each fraction through silica gel thin-layer Chromatography tests and analyzes, with GF254 lamellae, respectively with the methylene chloride-of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 Methanol is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to thin Layer chromatography testing result, respectively merge fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-132, Fraction 133-144, fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260 obtain-Fr.16 components of Fr.1; By component Fr.8 through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 70mL/h, every 12mL are a fraction, receive Collect 43 fractions, each fraction is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, with the dichloromethane of volume ratio 5:3 Alkane-acetone is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to Thin-layer chromatography testing result merges fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43 respectively, obtains 5 A inferior component Fr.8-1, Fr.8-2, Fr.8-3, Fr.8-4, Fr.8-5;Inferior component Fr.8-4 is pure through preparative high performance liquid chromatography Change, chromatographic column is YMC-Pack ODS-A, then with volume ratio is the Methanol+Water system elutions of 72:28, and flow velocity is 7mL/min collects the chromatographic peak that retention time is 36min and obtains chemical compounds I;By component Fr.9 through silica gel column chromatography, volume ratio The petroleum ether of 100:30-acetone mixed solvent elution, every 15mL are a fraction, collect the fraction containing compounds Ⅳ and are changed Close object IV;By component Fr.11 through silica gel column chromatography, petroleum ether-acetone of volume ratio 100:7,100:10,100:15,100:20 Mixed solvent system elution, each gradient 80mL eluent, every 8mL are a fraction, collect 40 fractions, each fraction is through silicon Glue thin-layer chromatography tests and analyzes, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with body Sulfuric acid-ethanol solution of the product than 10:90 is as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography testing result, difference Merge fraction 1-8, fraction 9-15, fraction 16-31, fraction 32-40, obtains 4 inferior components Fr.11-1, Fr.11-2, Fr.11- 3,Fr.11-4;Inferior component Fr.11-4 is purified through preparative high performance liquid chromatography, is mixed with volume ratio for the methanol-water of 80:20 Solvent system elution, chromatographic column are YMC-Pack ODS-A, flow velocity 7mL/min, collect the chromatographic peak that retention time is 69min Obtain compound III;By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution is eluted, often 5mL is a fraction, collects the fraction containing compound ii and obtains compound ii.
4. the preparation method of isopentene group flavone compound according to claim 2, which is characterized in that with Himalayan mayapple fruit Medicinal material 6kg is raw material, and with 30L, volumetric concentration for 75% ethyl alcohol heating and refluxing extraction 3 times, Extracting temperature is 90 DEG C, is extracted every time Time be 2 hours, ethyl alcohol is recovered under reduced pressure, obtains medicinal extract shape ethanol extract, is suspended in the distilled water of 2L, successively with petroleum ether, Methylene chloride, ethyl acetate, n-butanol respectively extract 3 times, each 2L, and the time is 2 hours;By Ethyl acetate fraction through silica gel Column chromatography initial gross separation is successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50,100:70, The petroleum ether of 100:100,100:200,0:100-acetone mixed solvent system carry out gradient elution, and each gradient is eluted with 9.1L Liquid, flow velocity 10mL/min, every 350ml volume are a fraction, collect 260 fractions, each fraction is examined through silica gel thin-layer chromatography Analysis is surveyed, with GF254 lamellae, is made respectively with the methylene chloride-methanol of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 For solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography Testing result merges fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-132, fraction respectively 133-144, fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, fraction 189- 195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260 obtain-Fr.16 components of Fr.1;By group Divide Fr.8 through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 50mL/h, every 8mL are a fraction, collect 43 Fraction, each fraction are tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, with the dichloromethane-acetone of volume ratio 5:3 As solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to thin layer color Testing result is composed, merges fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43 respectively, obtains 5 subgroups Part Fr.8-1, Fr.8-2, Fr.8-3, Fr.8-4, Fr.8-5;Inferior component Fr.8-4 is purified through preparative high performance liquid chromatography, color Spectrum column is YMC-Pack ODS-A, then is eluted with volume ratio for the methanol-water mixed solution of 72:28, and flow velocity 7mL/min is received Integrate retention time and obtains chemical compounds I as the chromatographic peak of 36min;By component Fr.9 through silica gel column chromatography, the stone of volume ratio 100:30 Oily ether-acetone mixed solvent elution, every 10mL are a fraction, collect the fraction containing compounds Ⅳ and obtain compounds Ⅳ;It will Component Fr.11 is through silica gel column chromatography, petroleum ether-acetone mixed solvent system of volume ratio 100:7,100:10,100:15,100:20 System elution, each gradient 5mL eluent, every 5mL are a fraction, collect 40 fractions, each fraction is through silica gel thin-layer chromatography It tests and analyzes, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with volume ratio 10:90's Sulfuric acid-ethanol solution is as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography testing result, merge respectively fraction 1-8, Fraction 9-15, fraction 16-31, fraction 32-40, obtain 4 inferior components Fr.11-1, Fr.11-2, Fr.11-3, Fr.11-4;It is sub- Component Fr.11-4 is purified through preparative high performance liquid chromatography, is the Methanol+Water system elutions of 80:20 with volume ratio, Chromatographic column is YMC-Pack ODS-A, flow velocity 7mL/min, collects the chromatographic peak that retention time is 69min and obtains compound III; By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution elution, every 3mL is a fraction, is received Fraction of the collection containing compound ii obtains compound ii.
5. the preparation method of isopentene group flavone compound according to claim 2, which is characterized in that with Himalayan mayapple fruit Medicinal material 8kg is raw material, and with 24L, volumetric concentration for 85% ethyl alcohol heating and refluxing extraction 3 times, Extracting temperature is 92 DEG C, is extracted every time Time is 1.5 hours, and ethyl alcohol is recovered under reduced pressure, obtains medicinal extract shape ethanol extract, is suspended in the distilled water of 2.8L, successively with petroleum Ether, methylene chloride, ethyl acetate, n-butanol respectively extract 3 times, each 2.8L, and the time is 1.5 hours;Ethyl acetate is extracted into portion Position through silica gel column chromatography initial gross separation, be successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50, The petroleum ether of 100:70,100:100,100:200,0:100-acetone mixed solvent system carry out gradient elution, and each gradient is used 11.7L eluent, flow velocity 13mLmin-1, every 450ml volume is a fraction, and it is thin through silica gel to collect 260 fractions, each fraction Layer chromatography tests and analyzes, with GF254 lamellae, respectively with the dichloromethane of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 Alkane-methanol is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to Thin-layer chromatography testing result merges fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-respectively 132, fraction 133-144, fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, Fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260 obtain Fr.1-Fr.16 Component;By component Fr.8 through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 65mL/h, every 10mL are one stream Part, collect 43 fractions, each fraction tests and analyzes through silica gel thin-layer chromatography, with GF254 lamellae, with the two of volume ratio 5:3 Chloromethanes-acetone is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, According to thin-layer chromatography testing result, merges fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43 respectively, obtain To 5 inferior components Fr.8-1, Fr.8-2, Fr.8-3, Fr.8-4, Fr.8-5;Inferior component Fr.8-4 is through preparative high-efficient liquid phase color Spectrum purifying, chromatographic column are YMC-Pack ODS-A, then with volume ratio are the Methanol+Water system elutions of 72:28, flow velocity For 7mL/min, collects the chromatographic peak that retention time is 36min and obtain chemical compounds I;By component Fr.9 through silica gel column chromatography, volume Petroleum ether-acetone mixed solvent elution than 100:30, every 12mL is a fraction, collects the fraction containing compounds Ⅳ and obtains Compounds Ⅳ;By component Fr.11 through silica gel column chromatography, the petroleum ether-the third of volume ratio 100:7,100:10,100:15,100:20 The elution of ketone mixed solvent system, each gradient 75mL eluent, every 7.5mL are a fraction, collect 40 fractions, each fraction It is tested and analyzed through silica gel thin-layer chromatography, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, Using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to thin-layer chromatography testing result, Respectively merge fraction 1-8, fraction 9-15, fraction 16-31, fraction 32-40, obtain 4 inferior component Fr.11-1, Fr.11-2, Fr.11-3,Fr.11-4;Inferior component Fr.11-4 is purified through preparative high performance liquid chromatography, is the methanol-of 80:20 with volume ratio Water mixed solvent system elutions, chromatographic column are YMC-Pack ODS-A, flow velocity 7mL/min, and collecting retention time is 69min's Chromatographic peak obtains compound III;By component Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution is washed De-, every 4.5mL is a fraction, collects the fraction containing compound ii and obtains compound ii.
6. the preparation method of isopentene group flavone compound according to claim 2, which is characterized in that by Himalayan mayapple fruit Medicinal material 7kg is raw material, and with 28L, volumetric concentration for 75% ethyl alcohol heating and refluxing extraction 3 times, Extracting temperature is 90 DEG C, is extracted every time Time is 2 hours, and ethyl alcohol is recovered under reduced pressure, obtains medicinal extract shape ethanol extract, is suspended in the distilled water of 2.4L, successively with petroleum Ether, methylene chloride, ethyl acetate, n-butanol respectively extract 3 times, each 2.4L, and the time is 2 hours;By Ethyl acetate fraction Through silica gel column chromatography initial gross separation, be successively 100:0,100:5 with volume ratio, 100:7,100:10,100:30,100:50, The petroleum ether of 100:70,100:100,100:200,0:100-acetone mixed solvent system carry out gradient elution, and each gradient is used 10.4L eluent, flow velocity 12mLmin-1, every 400ml volume is a fraction, and it is thin through silica gel to collect 260 fractions, each fraction Layer chromatography tests and analyzes, with GF254 lamellae, respectively with the dichloromethane of petroleum ether-acetone of volume ratio 1:1 and volume ratio 5:1 Alkane-methanol is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, according to Thin-layer chromatography testing result merges fraction 1-35, fraction 36-85, fraction 86-104, fraction 105-115, fraction 116-respectively 132, fraction 133-144, fraction 145-157, fraction 158-163, fraction 164-170, fraction 171-182, fraction 183-188, Fraction 189-195, fraction 196-204, fraction 205-208, fraction 209-234, fraction 235-260 obtain Fr.1-Fr.16 Component;By component Fr.8 through Sephadex LH-20 gel column chromatography, methanol elution, flow velocity 55mL/h, every 9mL are one stream Part, collect 43 fractions, each fraction tests and analyzes through silica gel thin-layer chromatography, with GF254 lamellae, with the two of volume ratio 5:3 Chloromethanes-acetone is as solvent, using sulfuric acid-ethanol solution of volume ratio 10:90 as color developing agent, 105 DEG C of 3-5min of heating, According to thin-layer chromatography testing result, merges fraction 4-7, fraction 8-13, fraction 9-26, fraction 27-33, fraction 34-43 respectively, obtain To 5 inferior components Fr.8-1, Fr.8-2, Fr.8-3, Fr.8-4, Fr.8-5;Inferior component Fr.8-4 through preparative high-performance liquid chromatographic, Chromatographic column is YMC-Pack ODS-A, then is eluted with volume ratio for the methanol-water mixed solution of 72:28, flow velocity 7mL/min, It collects the chromatographic peak that retention time is 36min and obtains chemical compounds I;By component Fr.9 through silica gel column chromatography, volume ratio 100:30's Petroleum ether-acetone mixed solvent elution, every 11mL are a fraction, collect the fraction containing compounds Ⅳ and obtain compounds Ⅳ; By component Fr.11 through silica gel column chromatography, petroleum ether-acetone mixed solvent of volume ratio 100:7,100:10,100:15,100:20 System elutions, each gradient 70mL eluent, every 7mL are a fraction, collect 40 fractions, each fraction is through silica gel thin-layer chromatography Spectrum tests and analyzes, with GF254 lamellae, respectively using petroleum ether-acetone of volume ratio 5:4 as solvent, with volume ratio 10:90 Sulfuric acid-ethanol solution as color developing agent, 105 DEG C of 3-5min of heating merge fraction 1-according to thin-layer chromatography testing result respectively 8, fraction 9-15, fraction 16-31, fraction 32-40 obtain 4 Arius parts Fr.11-1, Fr.11-2, Fr.11-3, Fr.11-4; Arius part Fr.11-4 is purified through preparative high-performance liquid chromatographic, is eluted with volume ratio for the Methanol+Water of 80:20, chromatography Column is YMC-Pack ODS-A, flow velocity 7mL/min, collects the chromatographic peak that retention time is 69min and obtains compound III;By group Divide Fr.13 through silica gel column chromatography, volume ratio 100:40 petroleum ether-acetone mixed solution elution, every 4mL is a fraction, and collection contains There is the fraction of compound ii to obtain compound ii.
7. isopentene group flavone compound Chinese podophyllum root ketone Q (sinoflavonoids Q I) described in claim 1, peach Seven ketone R (sinoflavonoids R II), Chinese podophyllum root ketone S (sinoflavonoids S III), Chinese podophyllum root ketone T (sinoflavonoids T IV) is preparing the application in antioxidant.
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