CN107011308A - The method that polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit - Google Patents
The method that polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit Download PDFInfo
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- CN107011308A CN107011308A CN201710249297.9A CN201710249297A CN107011308A CN 107011308 A CN107011308 A CN 107011308A CN 201710249297 A CN201710249297 A CN 201710249297A CN 107011308 A CN107011308 A CN 107011308A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[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
- C07D311/28—Benzo[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
- C07D311/30—Benzo[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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[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
- C07D311/40—Separation, e.g. from natural material; Purification
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Abstract
A kind of present invention isolates and purifies polymethoxyflavone class compound method in providing mandarin orange fruit from bowl.This method is extracted using the pericarp of bowl mandarin orange fruit as raw material using ultrasonic assistant,
Description
Technical field
The invention belongs to the extraction separation and purification technical field of active ingredients in natural plants, and in particular to from bowl mandarin orange fruit
In isolate and purify the method for polymethoxyflavone class compound, be, using bowl mandarin orange fruit rind as raw material, to be carried using ultrasonic assistant
Take,C18 solid-phase extraction columns and HSCCC (high speed adverse current chromatogram) GC-MS isolate and purify simultaneously Nobiletin,
The method of orange peel element and three kinds of polymethoxyflavone class compounds of 5- demethylnobiletins.
Background technology
Bowl mandarin orange (Citrus reticulata cv.Suavissima) is a variety for Rutaceae Citrus,
It is traditional special product of Wenzhou, Zhejiang Province, Lishui Prefecture, has there is the cultivation history of more than 2,000 years.Bowl mandarin orange has anti-swell among the people
Knurl, heat of dispelling are promoted the production of body fluid, preventing phlegm from forming and stopping coughing, the special food medicine function such as refreshing and detoxicating, these effects may with bowl mandarin orange rich in Polymethoxylated
Flavone compound is relevant.Polymethoxyflavone (Polymethoxylated Flavonoids, PMFs) refers to there is 4 and 4
The flavone compound of individual above methoxy substitution base, is mainly derived from Rutaceae citrus plant, especially in citrusfruit
Rich content in pericarp.Polymethoxyflavone class compound in citrusfruit is in antitumor, anti-inflammatory, anti-mutagenesis and protection painstaking effort
There is activity well, the biological mechanism research on polymethoxyflavone is also gradually goed deep into terms of pipe.From 1934
Since isolating polymethoxyflavone class compound monomer first, people have carried out substantial amounts of research to its activity.Grind in recent years
Study carefully discovery, polymethoxyflavone class compound, which has, to be suppressed cancer cell multiplication, the effect of resistance invasion and metastasis of tumor, promotes cancer thin
The bioactivity such as born of the same parents' apoptosis and autophagy.
Nobiletin, orange peel element and 5- demethylnobiletins are main polymethoxyflavone class compounds in citrus.River
Hesperetin (nobiletin), alias：Chuan Piting, nobiletin, CAS：478-01-3, molecular formula：C21H22O8, molecular weight：
402.395, chemical name is 2- (3,4-Dimethoxyphenyl) -5,6,7,8-tetramethoxy-4H-chromen-4-
one.It is present in a class material in bowl mandarin orange or other citrus fruits, sterling is white, powdered.Orange peel element (tangeretin),
CAS：2798-20-1, molecular formula：C20H20O7, molecular weight：372.369, outward appearance：White powder.5- demethylnobiletins (5-
Demethylnobiletin), CAS：2174-59-6, molecular formula：C20H20O8, molecular weight：388.368, outward appearance：Yellowish toner
End.
With the structure of matter determination of polymethoxyflavone class compound and the further investigation to its bioactivity, many first
The market demand of epoxide flavone compound gradually increases.The existing separation on polymethoxyflavone mainly uses macropore tree
Lipid layer is analysed and preparative high performance liquid chromatography, and its limitation is complex process, and cost is higher, isolated monomer purity it is low or
Preparation amount, it is difficult to develop into the isolation technics that separation purity is high, preparation amount is big.
The content of the invention
In view of the defect that above-mentioned prior art is present, polymethoxyflavone is isolated and purified it is an object of the invention to provide one kind
The method of class compound, isolates and purifies Nobiletin, orange peel element, 5- demethylnobiletins in being a kind of mandarin orange fruit rind from bowl
Method, fast and effeciently can simultaneously be isolated and purified from bowl mandarin orange fruit rind using this method and obtain the river that purity is not less than 98%
Hesperetin, orange peel element and 5- demethylnobiletins, are realized especially by following steps：
(1) sample extraction：Taking the bowl mandarin orange pericarp powder of freeze-drying of certain mass, (solid-to-liquid ratio is 1 with 95% ethanol：
20) ultrasonic extraction 2 times, 25 DEG C of Extracting temperature, each 45min after vacuum filtration, merges supernatant, on a rotary evaporator
It is evaporated to without ethanol phase, is dissolved in deionized water.
(2)C18 solid-phase extraction columns are sweetened off and are segmented：Take the aqueous solution loading obtained in step (1)Solid-phase extraction column is first washed with deionized water de- 25 times of bed volumes (BV) and removes pole after C18 solid-phase extraction columns, loading
Property higher impurity, elution is then carried out with 35% methanol 12BV removes impurity, is then eluted with 100% methanol 3BV, elution stream
Speed be 1mL/min, collect eluent, eluent on a rotary evaporator 36 DEG C be evaporated obtain after preliminary decontamination be rich in many first
The powder of epoxide flavonoid component.
(3) HSCCC further isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletins：Prepare n-hexane-acetic acid
Ethyl ester-methanol-water (1.1：0.8：1.1：0.9) dicyandiamide solution, fully shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase,
HSCCC splitters are pumped into 20mL/min flow velocitys with stationary phase first, after being full of, counter-current chromatograph is opened and is adjusted to rotating speed
800rpm, HSCCC splitters are pumped into by mobile phase with 2mL/min speed, will be preliminary when mobile phase outflow stable from outlet
100% methanol elution fraction 50mg after decontamination is dissolved under 5mL sample introduction in phase, the collection of illustrative plates gathered according to chromatographic detector
Peak type is in charge of collection each component, and the efflux between specific peak is started and terminated collects resulting component, peak I, peak respectively
II and peak III component be respectively Nobiletin, orange peel element and 5- demethylnobiletins (as shown in Figure 3 and Figure 4).
Nobiletin, orange peel element and the 5- demethylnobiletins that present invention purifying is obtained pass through ultra performance liquid chromatography
(UPLC) identified with mass spectrum (MS).
Another object of the present invention is that described method isolates and purifies polymethoxyflavone class chemical combination in bowl mandarin orange fruit
Application in thing.
The present invention is usedC18 SPEs and HSCCC GC-MSs, using bowl mandarin orange fruit rind powder as raw material
The Nobiletin for obtaining high-purity, orange peel element and 5- demethylnobiletins are isolated and purified simultaneously.The present invention is relative to past work
Skill has the following advantages：(1) protection of HTHP and inert gas is not needed, technique is simple；(2) it need not use with larger
The reagent of sharp aroma, production procedure is easy to operate safely；(3) it can be used for isolating and purifying the flavonoid of property closely
Thing, applicability is wide；(4) it is with short production cycle, it is thus only necessary to which that several hours can just complete whole process of purification；(5) purified product
The rate of recovery is high, and purity is high；(6) whole process of purification carries out accurate qualitative, quantitative by UPLC and LC-MS, and the degree of accuracy is high；(7) institute
Reused after solvent is recyclable, cost is relatively low；(8) polymethoxyflavone component is enriched with by early stage, can improved
HSCCC material resolution ratio and reproduction degree.
Brief description of the drawings
Fig. 1 is purifying process flow chart of the present invention.
Fig. 2 is that crude extract detects collection of illustrative plates through SPE UPLC, and wherein a is crude extract UPLC collection of illustrative plates, and b and d are crude extract
UPLC collection of illustrative plates through 35% meoh eluate during SPE, c and e pass through for crude extractC18 is segmented UPLC after purification
Collection of illustrative plates, in UPLC collection of illustrative plates, peak 1 is neohesperidin, and 2 be Nobiletin, and 3 be orange peel element, and 4 be 5- demethylnobiletins.
Fig. 3 is components I Nobiletin in the HSCCC collection of illustrative plates of embodiment 1, figure, and compositionⅱ is orange peel element, and component III is gone for 5-
Methine hesperetin.
Fig. 4 is components I Nobiletin in the HSCCC collection of illustrative plates of embodiment 2, figure, and compositionⅱ is orange peel element, and component III is gone for 5-
Methine hesperetin.
Fig. 5 is component through HSCCC after purification, components I (Nobiletin), compositionⅱ (orange peel element), and (5- goes first to component III
Nobiletin) UPLC collection of illustrative plates.
Fig. 6 is that second order mses identify collection of illustrative plates, and wherein a isC18 SPEs and the separation of HSCCC GC-MSs are pure
Change obtained Nobiletin monomer second order mses identification collection of illustrative plates；B isC18 SPEs and HSCCC GC-MSs point
From the plain monomer second order mses identification collection of illustrative plates of orange peel that purifying is obtained；C isC18 SPEs and HSCCC GC-MSs
Isolate and purify obtained 5- demethylnobiletin monomers second order mses identification collection of illustrative plates.
Embodiment
The present invention is further described in conjunction with the accompanying drawings and embodiments.
Embodiment 1
The operating method that the present invention isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletins is entered in accordance with the following steps
OK, referring to Fig. 1：
(1) ultrasonic assistant is extracted：Bowl mandarin orange fruit rind powder 95% ethanol (the solid-to-liquid ratio ratio of 10.3g freeze-dryings
1：20) after ultrasonic extraction three times (25 DEG C), each 45min, vacuum filtration, merge supernatant, be evaporated on a rotary evaporator to
Without ethanol phase, it is dissolved in deionized water, obtains the crude extract aqueous solution.
(2)C18 solid-phase extraction columns are sweetened off and are segmented：Take the crude extract aqueous solution about 5mL obtained in step (1)
LoadingSolid-phase extraction column is first washed with deionized water de- 25 times of bed volumes (BV) and gone after C18 solid-phase extraction columns, loading
Fall the higher impurity of polarity, then carrying out elution with 35% methanol 12BV removes impurity, then eluted, washed with 100% methanol 3BV
Separation of flow speed is 1mL/min, collects eluent about 12mL, and eluent is evaporated and obtained after preliminary decontamination for 36 DEG C on a rotary evaporator
The powder rich in polymethoxyflavone component.The step obtains the decontamination powder 207.2mg after preliminary purification, powder after purification
Total content >=80% of Nobiletin, orange peel element and 5- demethylnobiletins, is as a result shown in Fig. 2 b and 2c in end.
(3) HSCCC further isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletins：Prepare n-hexane-acetic acid
Ethyl ester-methanol-water (1.1：0.8：1.1：0.9) dicyandiamide solution, fully shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase,
HSCCC splitters are pumped into 20mL/min flow velocitys with stationary phase first, after being full of, counter-current chromatograph is opened and is adjusted to rotating speed
800rpm, HSCCC splitters are pumped into by mobile phase with 2mL/min speed, will be preliminary when mobile phase outflow stable from outlet
100% methanol elution fraction 50mg after decontamination is dissolved under 5mL sample introduction in phase, the collection of illustrative plates gathered according to chromatographic detector
(Fig. 3) is in charge of collection each component, and the purity of each component is determined with UPLC, merges gone containing Nobiletin, orange peel element and 5- respectively
The centrifuge tube of methine hesperetin, on a rotary evaporator 36 DEG C be evaporated obtain Nobiletin, orange peel element and 5- remove methine dried orange peel
Element.Plain and 5- demethylnobiletins the purity of Nobiletin, orange peel is obtained >=98%, as a result referring to Fig. 5.
Embodiment 2
The operating method that the present invention isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletins is entered in accordance with the following steps
OK, referring to Fig. 1：
(1) ultrasonic assistant is extracted：Bowl mandarin orange fruit rind powder 95% ethanol (the solid-to-liquid ratio ratio of 11.2g freeze-dryings
1：20) after ultrasonic extraction three times (25 DEG C), each 45min, vacuum filtration, merge supernatant, be evaporated on a rotary evaporator to
Without ethanol phase, it is dissolved in deionized water, obtains the crude extract aqueous solution.
(2)C18 solid-phase extraction columns are sweetened off and are segmented：Take the crude extract aqueous solution about 5mL obtained in step (1)
LoadingSolid-phase extraction column is first washed with deionized water de- 25 times of bed volumes (BV) and gone after C18 solid-phase extraction columns, loading
Fall the higher impurity of polarity, then carrying out elution with 35% methanol 12BV removes impurity, then eluted, washed with 100% methanol 3BV
Separation of flow speed is 1mL/min, collects eluent about 13mL, and eluent is evaporated and obtained after preliminary decontamination for 36 DEG C on a rotary evaporator
The powder rich in polymethoxyflavone component.The step obtains the decontamination powder 220.3mg after preliminary purification, powder after purification
Total content >=80% of Nobiletin, orange peel element and 5- demethylnobiletins in end, as a result referring to Fig. 2 d and 2e.
(3) HSCCC further isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletins：Prepare n-hexane-acetic acid
Ethyl ester-methanol-water (1.1：0.8：1.1：0.9) dicyandiamide solution, fully shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase,
HSCCC splitters are pumped into 20mL/min flow velocitys with stationary phase first, after being full of, counter-current chromatograph is opened and is adjusted to rotating speed
800rpm, HSCCC splitters are pumped into by mobile phase with 2mL/min speed, will be preliminary when mobile phase outflow stable from outlet
100% methanol elution fraction 50mg after decontamination is dissolved under 5mL sample introduction in phase, the collection of illustrative plates gathered according to chromatographic detector
(Fig. 4) is in charge of collection each component, and the purity of each component is determined with UPLC, merges gone containing Nobiletin, orange peel element and 5- respectively
The centrifuge tube of methine hesperetin, on a rotary evaporator 36 DEG C be evaporated obtain Nobiletin, orange peel element and 5- remove methine dried orange peel
Element.Plain and 5- demethylnobiletins the purity of Nobiletin, orange peel is obtained >=98%, as a result referring to Fig. 5.
The screening that the present invention of embodiment 3 carries out influence factor by tests below is determined
1st, the selection of purified material
Fresh bowl mandarin orange fruit rind, is freeze-dried to constant weight, is clayed into power with sample grinding machine.The freezing of certain mass is taken to do
With 95% ethanol, (solid-to-liquid ratio is 1 to dry bowl mandarin orange pericarp powder：20) ultrasonic extraction 45min (25 DEG C), are repeated 2 times, are taken out through vacuum
After filter, merge supernatant, the UPLC for polymethoxyflavone class compound is analyzed.It is (molten that UPLC mobile phases include deionized water
Liquid A) and chromatogram acetonitrile (solution B), using gradient elution, Detection wavelength is 330nm, and temperature is room temperature (25 DEG C), and sample size is 2
μ l, flow velocity is 0.3ml/min, and condition is：Solvent B：0-5min, 20%, 5-8min：20%-34%；8-20min：34%-
60%, 20-22min：60%-100%, 22~23min：100% is constant, 23~24min：100%~20%, holding 20% is molten
Terminate a circulation after liquid B1min.As a result show, higher polymethoxyflavone kind compound content contained in bowl mandarin orange pericarp,
And impurity is less, purified material can be used as.As a result referring to Fig. 2 a.
2、The selection of C18 SPE methanol wash-out concentrations
C18 solid-phase extraction columns activate pillar, 2BV deionized water levels through 2 methanol of column volume (BV) 100%
After weighing apparatus pillar, 1BV or so extract solution loadings, loading flow velocity 1mL/min.Solid-phase extraction column after loading first rinses 25BV with water and gone
Sugar, is then eluted, each gradient 10BV with 20%, 25%, 30%, 35%, 40%, 45%, 50% grade low concentration methanol respectively,
Then eluted with 100% methanol 3BV, elution flow rate is 1mL/min.With 100% first after UPLC detection various concentrations methanol impurity eliminations
The content of Nobiletin, orange peel element and 5- demethylnobiletins in alcohol eluen, it is determined that most suitable methanol wash-out concentration.As a result table
Bright, methanol concentration can efficiently remove flavanone impurity in crude extract when being equal to or higher than 35% condition, after 100% elutes
Polymethoxyflavone (referring to table 1) can be enriched with, and river dried orange peel can be preferably preserved when methanol wash-out concentration is 35%
The Polymethoxylated component such as element is not washed away, therefore then the present invention collects 100% using impurity elimination is eluted under the conditions of 35% methanol
Meoh eluate.ThroughC18 SPEs segmentation impurity elimination purifying crude extract can be enriched with polymethoxyflavone class
Compound, reduces impurity.
Table 1
The selection of 3.HSCCC dicyandiamide solutions
It is used for HSCCC dicyandiamide solution by determining distribution coefficient (K) come preliminary screening.It is different molten by what is prepared in advance
Agent system is fully mixed, after stratification, draws the phase up and down of same volume, the preliminary purification powder added after segmentation impurity elimination,
The peak area of Nobiletin in phase up and down, orange peel element and 5- demethylnobiletins is determined respectively, up and down the ratio between both phase peak areas
The as distribution coefficient of the two.As a result show, n-hexane-ethyl acetate-methanol-water (1.1：0.8：1.1：0.9) dicyandiamide solution
In, K (Nobiletin)=0.55, K (orange peel element)=0.78, K (5- demethylnobiletins)=1.81, the ratio between three is in 0.5-2
In the range of (referring to table 2).Therefore the present invention applies the dicyandiamide solution to be further purified.It is further purified through HSCCC and obtains pure
The higher powder (referring to Fig. 5) of degree, it is high-purity Nobiletin as a result to show component I, and component II is high-purity orange peel element, component
III is high-purity 5- demethylnobiletins (referring to Fig. 5).Three kinds of structures of matter are identified through second order mses (MS/MS).Mass Spectrometry Conditions：
ESI ion guns, positive ion mode (+ESI)；Dry gas (N2) temperature：350℃；Flow velocity：10.0L/min；Nebulizer pressure：
35psi；Capillary voltage：4000V；Mass scan range：M/z 100~500.Mass spectrometric data collection uses MRM patterns.It is broken
Mode is consistent with document report, confirms as Nobiletin, orange peel element and 5- demethylnobiletins (referring to Fig. 6).
Table 2
Claims (5)
1. the method for polymethoxyflavone class compound is isolated and purified in a kind of mandarin orange fruit from bowl, it is characterised in that by following
Step is realized：
(1) sample extraction：The bowl mandarin orange pericarp powder of freeze-drying is taken to be extracted with 95% EtOH Sonicate, solid-to-liquid ratio is 1：20, extract
25 DEG C of temperature, each 45min after vacuum filtration, merges supernatant, is evaporated to without ethanol phase, is dissolved on a rotary evaporator
In deionized water；
(2)Sep-C18 solid-phase extraction columns are sweetened off and are segmented：Take the aqueous solution loading Sep- obtained in step (1)
De- 25 bed volumes are first washed with deionized water in solid-phase extraction column after C18 solid-phase extraction columns, loading, remove higher miscellaneous of polarity
Matter, then carries out gradient elution with methanol, and eluent is evaporated and obtained rich in polymethoxyflavone for 36 DEG C on a rotary evaporator
100% elution fraction；
(3) HSCCC further isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletins：Prepare n-hexane-acetic acid second
The dicyandiamide solution of ester-methanol-water, fully shakes up overnight, upper phase be stationary phase, lower phase be mobile phase, first with stationary phase with
20mL/min flow velocitys are pumped into HSCCC splitters, after being full of, and open counter-current chromatograph and rotating speed is adjusted into 800rpm, by mobile phase
HSCCC splitters are pumped into 2mL/min speed, when mobile phase outflow stable from outlet, 100% that step (2) is obtained
Elution fraction 50mg is dissolved under 5mL sample introduction in phase, and the peak type in the collection of illustrative plates gathered according to chromatographic detector is in charge of collection each group
Point, the component at peak I, peak II and peak III is respectively Nobiletin, orange peel element and 5- demethylnobiletins；
The composition of each component is determined with UPLC, the test tube containing single polymethoxyflavone class compound is merged respectively, in rotation
36 DEG C are evaporated three kinds of polymethoxyflavone class compounds are obtained on evaporimeter, and respectively Nobiletin, orange peel element, 5- remove methine
Hesperetin, product purity is more than 98%.
2. the method for polymethoxyflavone class compound is isolated and purified in a kind of mandarin orange fruit from bowl according to claim 1,
Characterized in that, the gradient elution described in step (2) is respectively 35% methanol solution, 100% methanol solution, eluting order is
35% bed volume of methanol 12,100% methanol, 3 column volumes.
3. the method for polymethoxyflavone class compound is isolated and purified in a kind of mandarin orange fruit from bowl according to claim 1,
Characterized in that, the solid-phase extraction column model Waters Sep- described in step (2)Vac 12cc(2g)
C18Cartridges。
4. the method for polymethoxyflavone class compound is isolated and purified in a kind of mandarin orange fruit from bowl according to claim 1,
Characterized in that, when step (3) carries out HSCCC purifying, selecting n-hexane-ethyl acetate-methanol-water=1.1：0.8：1.1：
0.9 dicyandiamide solution.
5. answering in polymethoxyflavone class compound is isolated and purified in bowl mandarin orange fruit according to the method described in claim 1
With.
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| CN109321543A (en) * | 2018-11-02 | 2019-02-12 | 浙江大学 | The oxygen transmethylase and its encoding gene of participation orange peel flavones synthesis and application |
| CN109394878A (en) * | 2018-12-10 | 2019-03-01 | 浙江大学 | A kind of bowl mandarin orange fruit is rich in the lipid-loweringing purposes of polymethoxyflavone component extract |
| CN113801084A (en) * | 2021-10-14 | 2021-12-17 | 三峡大学 | Polymethoxyflavone extracted from orange vinegar fermentation substrate sludge, and extraction method and application thereof |
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Cited By (10)
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| CN108727324A (en) * | 2018-07-11 | 2018-11-02 | 重庆西南果品营养研究院 | A method of isolating and purifying citrus polymethoxyflavone |
| CN108727324B (en) * | 2018-07-11 | 2021-07-30 | 重庆西南果品营养研究院 | Method for separating and purifying citrus polymethoxylated flavones |
| CN109172667A (en) * | 2018-10-17 | 2019-01-11 | 浙江大学 | A kind of bowl mandarin orange fruit is rich in the hypoglycemic purposes of polymethoxyflavone component extract |
| CN109321543A (en) * | 2018-11-02 | 2019-02-12 | 浙江大学 | The oxygen transmethylase and its encoding gene of participation orange peel flavones synthesis and application |
| CN109394878A (en) * | 2018-12-10 | 2019-03-01 | 浙江大学 | A kind of bowl mandarin orange fruit is rich in the lipid-loweringing purposes of polymethoxyflavone component extract |
| CN113801084A (en) * | 2021-10-14 | 2021-12-17 | 三峡大学 | Polymethoxyflavone extracted from orange vinegar fermentation substrate sludge, and extraction method and application thereof |
| CN113801084B (en) * | 2021-10-14 | 2023-11-28 | 三峡大学 | Polymethoxy flavone extracted from orange vinegar fermentation substrate sludge, extraction method and application |
| CN114053346A (en) * | 2021-11-04 | 2022-02-18 | 中山大学 | Application of phyllanthus emblica embryo polymethoxylated flavonoids compound in preparation of blood fat reducing product |
| CN115736151A (en) * | 2022-12-06 | 2023-03-07 | 北冰洋（北京）饮料食品有限公司 | Method for preparing beverage from citrus processing by-product |
| CN115736151B (en) * | 2022-12-06 | 2024-04-09 | 北冰洋（北京）饮料食品有限公司 | Method for preparing beverage by using citrus processing byproducts |
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