CN107011308B - The method of polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit - Google Patents
The method of polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit Download PDFInfo
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- CN107011308B CN107011308B CN201710249297.9A CN201710249297A CN107011308B CN 107011308 B CN107011308 B CN 107011308B CN 201710249297 A CN201710249297 A CN 201710249297A CN 107011308 B CN107011308 B CN 107011308B
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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
Abstract
The present invention provides a kind of method that polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit.This method is using the pericarp of bowl mandarin orange fruit as raw material, using ultrasonic wave assisted extraction,
Description
Technical field
The invention belongs to the extraction separation and purification technical fields 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 to be mentioned using bowl mandarin orange fruit rind as raw material using ultrasonic wave auxiliary
Take,The joint technology of C18 solid-phase extraction column and HSCCC (high speed adverse current chromatogram) isolate and purify simultaneously Nobiletin,
The method of three kinds of polymethoxyflavone class compounds of orange peel element and 5- demethylnobiletin.
Background technique
Bowl mandarin orange (Citrus reticulata cv.Suavissima) is a variety for Rutaceae Citrus,
It is traditional specialty of Wenzhou, Zhejiang Province, Lishui Prefecture, there are more than 2,000 years cultivation histories.Bowl mandarin orange has anti-swell civil
The special food medicine functions such as tumor, heat of dispelling promotes the production of body fluid, preventing phlegm from forming and stopping coughing, refreshing and detoxicating, these effects may in bowl mandarin orange rich in Polymethoxylated
Flavone compound is related.Polymethoxyflavone (Polymethoxylated Flavonoids, PMFs) refers to 4 and 4
The flavone compound of a 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
Pipe etc. has activity well, and the biological mechanism research about polymethoxyflavone is also gradually goed deep into.From 1934
Since isolating polymethoxyflavone class compound monomer for the first time, people have carried out a large amount of research to its activity.It grinds in recent years
Study carefully discovery, polymethoxyflavone class compound, which has, to be inhibited cancer cell multiplication, resists invasion and metastasis of tumor effect, promote cancer thin
The bioactivity such as born of the same parents' apoptosis and autophagy.
Nobiletin, orange peel element and 5- demethylnobiletin 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 substance 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, appearance: white powder.5- demethylnobiletin (5-
Demethylnobiletin), CAS:2174-59-6, molecular formula: C20H20O8, molecular weight: 388.368, appearance: yellowish toner
End.
With the structure of matter determination of polymethoxyflavone class compound and the further investigation to its bioactivity, more first
The market demand of oxygroup flavone compound is gradually increased.The existing separation about polymethoxyflavone mainly uses macropore tree
Rouge chromatography and preparative high performance liquid chromatography, limitation be complex process, higher cost, 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.
Summary of the invention
In view of the problems of the above-mentioned prior art, the object of the present invention is to provide one kind to isolate and purify polymethoxyflavone
The method of class compound, be it is a kind of isolated and purified from bowl mandarin orange fruit rind Nobiletin, orange peel element, 5- demethylnobiletin
Method can fast and effeciently isolate and purify to obtain river of the purity not less than 98% from bowl mandarin orange fruit rind using this method simultaneously
Hesperetin, orange peel element and 5- demethylnobiletin, are realized especially by following steps:
(1) sample extraction: take the bowl mandarin orange pericarp powder of the freeze-drying of certain mass with 95% ethyl alcohol (solid-to-liquid ratio 1:
20) ultrasonic extraction 2 times, after vacuum filtration, merge supernatant, on a rotary evaporator by 25 DEG C of Extracting temperature, each 45min
It is evaporated to no ethyl alcohol phase, is dissolved in deionized water.
(2)C18 solid-phase extraction column desaccharification and segmentation: aqueous solution loading obtained in step (1) is takenC18 solid-phase extraction column, solid-phase extraction column is first washed with deionized water de- 25 times of bed volumes (BV) and removes pole after loading
Property higher impurity, then carrying out elution with 35% methanol 12BV removes impurity, is then eluted with 100% methanol 3BV, and elution is flowed
Speed is 1mL/min, collects eluent, eluent on a rotary evaporator 36 DEG C be evaporated to obtain after preliminary decontamination rich in more first
The powder of oxygroup flavonoid component.
(3) HSCCC further isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletin: preparing n-hexane-acetic acid
Ethyl ester-methanol-water (1.1:0.8:1.1:0.9) dicyandiamide solution sufficiently shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase,
HSCCC splitter is pumped into 20mL/min flow velocity with stationary phase first, after being full of, counter-current chromatograph is opened and is adjusted to revolving speed
Mobile phase is pumped into HSCCC splitter with the speed of 2mL/min by 800rpm, will be preliminary when mobile phase stablizes outflow from outlet
100% methanol elution fraction 50mg after decontamination is dissolved under 5mL sample introduction in phase, according to the map of chromatographic detector acquisition
Peak type is in charge of collection each component, by specific peak start and terminate between efflux collect obtained component, peak I, peak respectively
II and peak III component be respectively Nobiletin, orange peel element and 5- demethylnobiletin (as shown in Figure 3 and Figure 4).
Nobiletin, orange peel element and the 5- demethylnobiletin that the present invention purifies pass through ultra performance liquid chromatography
(UPLC) it is identified with mass spectrum (MS).
Another object of the present invention is that the method isolates and purifies polymethoxyflavone class chemical combination in bowl mandarin orange fruit
Application in object.
The present invention usesC18 Solid Phase Extraction and HSCCC joint technology, using bowl mandarin orange fruit rind powder as raw material
It isolates and purifies to obtain the Nobiletin of high-purity, orange peel element and 5- demethylnobiletin simultaneously.The present invention is relative to past work
Skill has the following advantages: (1) not needing the protection of high temperature and pressure and inert gas, simple process；(2) it does not need using with larger
The reagent of sharp aroma, production procedure are easy to operate safely；(3) it can be used for isolating and purifying the very close flavonoid of property
Object, applicability are wide；(4) with short production cycle, it is thus only necessary to which that several hours can complete whole process of purification；(5) purified product
The rate of recovery is high, purity is high；(6) whole process of purification carries out accurate qualitative, quantitative by UPLC and LC-MS, and accuracy is high；(7) institute
It is reused after solvent is recyclable, cost is relatively low；(8) polymethoxyflavone component is enriched with by early period, can be improved
The substance resolution ratio and reproduction degree of HSCCC.
Detailed description of the invention
Fig. 1 is purifying process flow chart of the present invention.
Fig. 2 is crude extract through Solid Phase Extraction UPLC test map, and wherein a is crude extract UPLC map, and b and d are crude extract
UPLC map through 35% meoh eluate when Solid Phase Extraction, c and e are crude extract warpC18 is segmented UPLC after purification
Map, in UPLC map, peak 1 is neohesperidin, and 2 be Nobiletin, and 3 be orange peel element, and 4 be 5- demethylnobiletin.
Fig. 3 is the HSCCC map of embodiment 1, and components I Nobiletin in figure, compositionⅱ is orange peel element, and component III is gone for 5-
Methine hesperetin.
Fig. 4 is the HSCCC map of embodiment 2, and components I Nobiletin in figure, compositionⅱ is orange peel element, and component III is gone for 5-
Methine hesperetin.
Fig. 5 is the component through HSCCC after purification, and components I (Nobiletin), compositionⅱ (orange peel element), (5- goes first to component III
Nobiletin) UPLC map.
Fig. 6 is that second order ms identify map, and wherein a isC18 Solid Phase Extraction and the separation of HSCCC joint technology are pure
Change obtained Nobiletin monomer second order ms identification map；B isC18 Solid Phase Extraction and HSCCC joint technology point
The orange peel element monomer second order ms obtained from purifying identify map；C isC18 Solid Phase Extraction and HSCCC joint technology
The 5- demethylnobiletin monomer second order ms identification map isolated and purified.
Specific embodiment
The present invention is further described in conjunction with the accompanying drawings and embodiments.
Embodiment 1
The present invention isolate and purify Nobiletin, orange peel element and 5- demethylnobiletin operating method in accordance with the following steps into
Row, referring to Fig. 1:
(1) ultrasonic wave assisted extraction: bowl mandarin orange fruit rind powder 95% ethyl alcohol (the solid-to-liquid ratio ratio of 10.3g freeze-drying
1:20) three times (25 DEG C), each 45min after vacuum filtration, merges supernatant to ultrasonic extraction, be evaporated on a rotary evaporator to
It without ethyl alcohol phase, is dissolved in deionized water, obtains crude extract aqueous solution.
(2)C18 solid-phase extraction column desaccharification and segmentation: crude extract aqueous solution about 5mL obtained in step (1) is taken
LoadingC18 solid-phase extraction column, de- 25 times of bed volumes (BV) are first washed with deionized water in solid-phase extraction column after loading
Fall the higher impurity of polarity, then carries out elution with 35% methanol 12BV and remove impurity, then eluted, washed with 100% methanol 3BV
Separation of flow speed is 1mL/min, collects eluent about 12mL, and eluent is evaporated after obtaining 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- demethylnobiletin, 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- demethylnobiletin: preparing n-hexane-acetic acid
Ethyl ester-methanol-water (1.1:0.8:1.1:0.9) dicyandiamide solution sufficiently shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase,
HSCCC splitter is pumped into 20mL/min flow velocity with stationary phase first, after being full of, counter-current chromatograph is opened and is adjusted to revolving speed
Mobile phase is pumped into HSCCC splitter with the speed of 2mL/min by 800rpm, will be preliminary when mobile phase stablizes outflow from outlet
100% methanol elution fraction 50mg after decontamination is dissolved under 5mL sample introduction in phase, the map acquired according to chromatographic detector
(Fig. 3) is in charge of collection each component, with the purity of UPLC measurement each component, merges go 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.Obtain Nobiletin, orange peel element and 5- demethylnobiletin purity >=98%, as a result referring to Fig. 5.
Embodiment 2
The present invention isolate and purify Nobiletin, orange peel element and 5- demethylnobiletin operating method in accordance with the following steps into
Row, referring to Fig. 1:
(1) ultrasonic wave assisted extraction: bowl mandarin orange fruit rind powder 95% ethyl alcohol (the solid-to-liquid ratio ratio of 11.2g freeze-drying
1:20) three times (25 DEG C), each 45min after vacuum filtration, merges supernatant to ultrasonic extraction, be evaporated on a rotary evaporator to
It without ethyl alcohol phase, is dissolved in deionized water, obtains crude extract aqueous solution.
(2)C18 solid-phase extraction column desaccharification and segmentation: crude extract aqueous solution about 5mL obtained in step (1) is taken
LoadingC18 solid-phase extraction column, de- 25 times of bed volumes (BV) are first washed with deionized water in solid-phase extraction column after loading
Fall the higher impurity of polarity, then carries out elution with 35% methanol 12BV and remove impurity, then eluted, washed with 100% methanol 3BV
Separation of flow speed is 1mL/min, collects eluent about 13mL, and eluent is evaporated after obtaining 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 in end, orange peel element and 5- demethylnobiletin, as a result d and 2e referring to fig. 2.
(3) HSCCC further isolates and purifies Nobiletin, orange peel element and 5- demethylnobiletin: preparing n-hexane-acetic acid
Ethyl ester-methanol-water (1.1:0.8:1.1:0.9) dicyandiamide solution sufficiently shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase,
HSCCC splitter is pumped into 20mL/min flow velocity with stationary phase first, after being full of, counter-current chromatograph is opened and is adjusted to revolving speed
Mobile phase is pumped into HSCCC splitter with the speed of 2mL/min by 800rpm, will be preliminary when mobile phase stablizes outflow from outlet
100% methanol elution fraction 50mg after decontamination is dissolved under 5mL sample introduction in phase, the map acquired according to chromatographic detector
(Fig. 4) is in charge of collection each component, with the purity of UPLC measurement each component, merges go 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.Obtain Nobiletin, orange peel element and 5- demethylnobiletin purity >=98%, as a result referring to Fig. 5.
3 present invention of embodiment is determined by the screening that following tests carries out influence factor
1, 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.Take the freezing of certain mass dry
Dry bowl mandarin orange pericarp powder is repeated 2 times, is taken out through vacuum with 95% ethyl alcohol (solid-to-liquid ratio 1:20) ultrasonic extraction 45min (25 DEG C)
After filter, merge supernatant, the UPLC for polymethoxyflavone class compound is analyzed.UPLC mobile phase includes that deionized water is (molten
Liquid A) and chromatography acetonitrile (solution B), using gradient elution, Detection wavelength 330nm, temperature is room temperature (25 DEG C), sample volume 2
μ l, flow velocity 0.3ml/min, condition are as follows: solvent B:0-5min, 20%, 5-8min:20%-34%；8-20min:34%-
60%, 20-22min:60%-100%, 22~23min:100% are constant, 23~24min:100%~20%, and holding 20% is molten
Terminate a circulation after liquid B1min.The result shows that contain higher polymethoxyflavone kind compound content in bowl mandarin orange pericarp,
And impurity is less, can be used as purified material.As a result a referring to fig. 2.
2、The selection of C18 Solid Phase Extraction methanol wash-out concentration
C18 solid-phase extraction column is horizontal through 2 100% methanol of column volume (BV) activation pillars, 2BV deionized waters
After weighing apparatus pillar, 1BV or so extracting solution loading, loading flow velocity 1mL/min.Solid-phase extraction column after loading is first rinsed with water 25BV and goes
Then sugar is eluted with 20%, 25%, 30%, 35%, 40%, 45%, 50% equal low concentration methanols, each gradient 10BV respectively,
Then it is eluted with 100% methanol 3BV, elution flow rate 1mL/min.With 100% first after UPLC detection various concentration methanol impurity elimination
The content of Nobiletin, orange peel element and 5- demethylnobiletin, determines most suitable methanol wash-out concentration in alcohol eluen.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% elution
It can be enriched with polymethoxyflavone (referring to table 1), and can preferably save river dried orange peel 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 Solid Phase Extraction segmentation impurity elimination purifying crude extract can be enriched with polymethoxyflavone class
Object is closed, impurity is reduced.
Table 1
The selection of 3.HSCCC dicyandiamide solution
The dicyandiamide solution of HSCCC is used for come preliminary screening by measurement distribution coefficient (K).It is different molten by what is prepared in advance
Agent system mixes well, and after stratification, draws the phase up and down of same volume, the preliminary purification powder after segmentation impurity elimination is added,
The peak area of Nobiletin in phase up and down, orange peel element and 5- demethylnobiletin is measured respectively, up and down the ratio between both phase peak areas
The as distribution coefficient of the two.The result shows that 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- demethylnobiletin)=1.81, the ratio between three is in 0.5-2
(referring to table 2) in range.Therefore the present invention is further purified using the dicyandiamide solution.It is further purified to obtain through HSCCC pure
Spend higher powder (referring to Fig. 5), the results showed that component I is high-purity Nobiletin, and component II is high-purity orange peel element, component
III is high-purity 5- demethylnobiletin (referring to Fig. 5).Three kinds of structures of matter are identified through second order ms (MS/MS).Mass Spectrometry Conditions:
ESI ion source, positive ion mode (+ESI)；Dry gas (N2) temperature: 350 DEG C；Flow velocity: 10.0L/min；Nebulizer pressure:
35psi；Capillary voltage: 4000V；Mass scan range: m/z 100~500.Mass spectrometric data acquisition uses MRM mode.It is broken
Mode is consistent with document report, is confirmed as Nobiletin, orange peel element and 5- demethylnobiletin (referring to Fig. 6).
Table 2
Claims (3)
1. a kind of method for isolating and purifying polymethoxyflavone class compound from bowl mandarin orange fruit, which is characterized in that by following
Step is realized:
(1) sample extraction: taking the bowl mandarin orange pericarp powder of freeze-drying to be extracted with 95% EtOH Sonicate, solid-to-liquid ratio 1:20, extracts temperature
25 DEG C of degree, 45 min merges supernatant, is evaporated on a rotary evaporator to no ethyl alcohol phase, is dissolved in after vacuum filtration every time
In deionized water；
(2) Sep-pak C18 solid-phase extraction column desaccharification and segmentation: aqueous solution loading Sep-pak obtained in step (1) is taken
C18 solid-phase extraction column, de- 25 bed volumes are first washed with deionized water in solid-phase extraction column after loading, and it is higher miscellaneous to remove polarity
Matter, then carries out gradient elution with methanol, and eluent is evaporated to obtain 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- demethylnobiletin: preparing n-hexane-acetic acid second
Ester-methanol-water dicyandiamide solution sufficiently shakes up overnight, and upper phase is stationary phase, and lower phase is mobile phase, first with stationary phase with 20
ML/min flow velocity is pumped into HSCCC splitter, after being full of, opens counter-current chromatograph and revolving speed is adjusted to 800 rpm, by mobile phase with
The speed of 2 mL/min is pumped into HSCCC splitter, and when mobile phase stablizes outflow from outlet, 100% that step (2) is obtained is washed
De- 50 mg of component is dissolved under 5 mL sample introduction in phase, is in charge of collection each group according to the peak type in the map of chromatographic detector acquisition
Point, the component at peak I, peak II and peak III is respectively Nobiletin, orange peel element and 5- demethylnobiletin；
With the composition of UPLC measurement each component, merges the test tube for containing single polymethoxyflavone class compound respectively, rotating
It is evaporated three kinds of polymethoxyflavone class compounds is obtained for 36 DEG C on evaporimeter, respectively Nobiletin, orange peel element, 5- go first
Nobiletin, product purity is 98% or more；
Wherein gradient elution described in step (2) is respectively 35% methanol solution, 100% methanol solution, and eluting order is 35% methanol
12 column volumes, 100% methanol, 3 column volumes；
When step (3) carries out HSCCC purifying, n-hexane-ethyl acetate-methanol-water=1.1:0.8:1.1:0.9 solvent is selected
System.
2. a kind of method that polymethoxyflavone class compound is isolated and purified from bowl mandarin orange fruit according to claim 1,
It is characterized in that, solid-phase extraction column model Waters Sep-pak Vac 12cc 2g C18 described in step (2)
Cartridges。
3. the method according to claim 11 isolates and purifies answering in polymethoxyflavone class compound in bowl mandarin orange fruit
With.
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| 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 |
| CN109321543B (en) * | 2018-11-02 | 2021-07-13 | 浙江大学 | Oxygen methyltransferase participating in synthesis of citrus peel flavone and coding gene and application thereof |
| 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 |
| 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 |
| 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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| CN101774992A (en) * | 2010-01-26 | 2010-07-14 | 浙江工商大学 | Method for separating and preparing polymethoxyflavone monomer from orange skin |
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