CN105477029A - Preparation method of evening primrose seed flavone - Google Patents

Preparation method of evening primrose seed flavone Download PDF

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Publication number
CN105477029A
CN105477029A CN201510954982.2A CN201510954982A CN105477029A CN 105477029 A CN105477029 A CN 105477029A CN 201510954982 A CN201510954982 A CN 201510954982A CN 105477029 A CN105477029 A CN 105477029A
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seed
flavone
radix oenotherae
oenotherae erythrosepalae
ethanol
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刘学
曹光群
邱香
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Jiangnan University
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Jiangnan University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/50—Methods involving additional extraction steps
    • A61K2236/55—Liquid-liquid separation; Phase separation

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  • Health & Medical Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a preparation method of evening primrose seed flavone. The preparation method comprises the following steps: adding an ethanol solution with volume percentage ranging from 65% to 85% to crushed evening primrose seeds at the material-to-liquid ratio of 1 to (10-30), setting an extracting temperature at 30-70 DEG C, conducting ultrasonic-assisted extraction for 20-100min and filtering so as to obtain a solid filter residue and an extracting solution containing the evening primrose seed flavone; and decompressing the extracting solution, recovering ethanol, concentrating and drying, dissolving in 40% ethanol, processing a sample on a preprocessed polyamide chromatographic column, sequentially eluting the column by virtue of 40% ethanol, 80% ethanol and anhydrous ethanol with an eluting volume of 3-6-time column volume, collecting an eluent of 80% ethanol, decompressing and drying, so that the evening primrose seed flavone is obtained. The evening primrose seed flavone prepared by the preparation method disclosed by the invention is significant in antioxidant activity; and the evening primrose seed flavone is suitable to serve as a cosmetic functional additive.

Description

A kind of preparation method of seed of Radix Oenotherae erythrosepalae flavone
Technical field
The present invention relates to the Extraction and separation of plant, be specifically related to a kind of preparation method of seed of Radix Oenotherae erythrosepalae flavone.
Background technology
At home and abroad in the research of Radix Oenotherae erythrosepalae, the research of Radix Oenotherae erythrosepalae oil is reported and applies at most, also there is report to the research of flavones ingredient in redsepal evening primrose leaf, but the research of the dregs of rice after oil is carried to seed of Radix Oenotherae erythrosepalae and utilizes considerably less, do not make full use of Radix Oenotherae erythrosepalae plant resources.Research finds, extracted in the seed residue of Radix Oenotherae erythrosepalae oil and contain very strong anti-oxidative activity composition, this oxidation-resistant active ingredient it is reported as polyphenol chromocor class material.So far, still not about the report of the Isolation and purification technique of flavones ingredient in seed of Radix Oenotherae erythrosepalae, also have no and the exploitation of flavones ingredient in the seed of Radix Oenotherae erythrosepalae dregs of rice are studied.
Summary of the invention
The object of the present invention is to provide a kind of method of Extraction and separation purification of seed of Radix Oenotherae erythrosepalae flavone, the method is based on ultrasound-assisted extraction method, optimize the extraction process extracting total flavones from the remaining seed of Radix Oenotherae erythrosepalae dregs of rice after extracting Radix Oenotherae erythrosepalae oil, and adopt polyamide column chromatography separation and purification, obtain seed of Radix Oenotherae erythrosepalae total flavones.
The object of the invention is to be achieved through the following technical solutions:
The present invention relates to a kind of preparation method of seed of Radix Oenotherae erythrosepalae flavone, described method comprises the steps:
S1, extraction: take the seed of Radix Oenotherae erythrosepalae dregs of rice appropriate, be 1:10 ~ 1:30g/mL by solid-liquid ratio, add the alcoholic solution that volume fraction is 65% ~ 85%, Extracting temperature is set in 30 ~ 70 DEG C, ultrasonic assistant extracts 20 ~ 100 minutes, filter, obtain solid filter residue and the extracting solution containing seed of Radix Oenotherae erythrosepalae flavone;
S2, separation and purification: by described extracting solution decompression recycling ethanol containing seed of Radix Oenotherae erythrosepalae flavone and concentrate drying, be dissolved in 40% ethanol, be splined on the polyamide chromatographic column that pretreatment is good, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 3 ~ 6 times of column volumes, collects respectively and drying under reduced pressure, obtains components I, compositionⅱ and component III successively; Compositionⅱ is seed of Radix Oenotherae erythrosepalae total flavones.
Preferably, in step S1, described Extraction solvent is alcoholic solution, and concentration counts 75 ~ 85% with volume fraction, and solid-liquid ratio is 1:20 ~ 1:30, and Extracting temperature is 30 ~ 50 DEG C, and ultrasonic assistant extraction time is 60 ~ 100 minutes.
Preferred, in step S1, described Extraction solvent is solid-liquid ratio is 80% ethanol, and solid-liquid ratio is 1:25, and Extracting temperature is 30 DEG C, and extraction time is 60 minutes.
Preferably, in step S2, described concentrated dry thing is dissolved in 40% ethanol.
Preferably, in step S2, described separation process carries out separation and purification with polyamide chromatographic column.
Preferably, in step S2, described eluent is followed successively by 40%, and 80% and dehydrated alcohol.
Preferably, in step S2, described elution volume is 3 ~ 6 times of column volumes, and 80% ethanol elution, through drying under reduced pressure, obtains seed of Radix Oenotherae erythrosepalae total flavones.
The present invention has following beneficial effect:
1. the method for extraction and isolation Flavonoid substances from seed of Radix Oenotherae erythrosepalae is provided.
2. present invention process is a kind of quick, easy, effective extracting method, and extract obtained have significant anti-oxidation efficacy, is suitable for and makes cosmetic industry type additive.
Accompanying drawing explanation
By reading the detailed description done non-limiting example with reference to the following drawings, other features, objects and advantages of the present invention will become more obvious:
Fig. 1 is that concentration of alcohol (volume fraction) affects schematic diagram to total flavones yield;
Fig. 2 is that solid-liquid ratio affects schematic diagram to total flavones yield;
Fig. 3 is that Extracting temperature affects schematic diagram to flavone yield;
Fig. 4 affects schematic diagram to flavone yield extraction time.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in detail.Following examples will contribute to those skilled in the art and understand the present invention further, but not limit the present invention in any form.It should be pointed out that to those skilled in the art, without departing from the inventive concept of the premise, can also make certain adjustments and improvements.These all belong to protection scope of the present invention.
The present invention relates to a kind of based on ultrasonic assistant solvent extraction, and adopt polyamide column chromatography separation and purification, obtain the method for seed of Radix Oenotherae erythrosepalae total flavones, comprise, extraction step, be 1:10 ~ 1:30g/mL by solid-liquid ratio, take seed of Radix Oenotherae erythrosepalae dregs of rice ground product, add the alcoholic solution that volume fraction is 65% ~ 85%, Extracting temperature is set in 30 ~ 70 DEG C, ultrasonic assistant extracts 20 ~ 100 minutes, filters, and obtains solid filter residue and the extracting solution containing seed of Radix Oenotherae erythrosepalae flavone; Purification procedures, by described extracting solution decompression recycling ethanol containing seed of Radix Oenotherae erythrosepalae flavone and concentrate drying, be dissolved in 40% ethanol, be splined on the polyamide chromatographic column that pretreatment is good, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 3 ~ 6 times of column volumes, collect respectively and drying under reduced pressure, obtain components I, compositionⅱ and component III successively; Compositionⅱ is seed of Radix Oenotherae erythrosepalae total flavones.
The determination of extraction process
In the present invention, in the research carrying out extraction process, find that the principal element affecting extraction efficiency has: concentration of alcohol, solid-liquid ratio, Extracting temperature, extraction time.Therefore, at concentration of alcohol (with volume fraction) 65% ~ 85%, solid-liquid ratio 1:10 ~ 1:30, Extracting temperature 30 ~ 70 DEG C, and in 20 ~ 100 minutes extraction times, with total flavones yield for index, adopt experiments of single factor to investigate the impact of each factor on extraction efficiency, and adopt orthogonal experiment method Optimized Extraction Process further.
Fig. 1 is that concentration of alcohol (volume fraction) affects schematic diagram to total flavones yield; Fig. 2 is that solid-liquid ratio affects schematic diagram to total flavones yield; Fig. 3 is that Extracting temperature affects schematic diagram to flavone yield; Fig. 4 affects schematic diagram to flavone yield extraction time.From Fig. 1,2,3,4, be 75 ~ 85% at concentration of alcohol (with volume fraction), solid-liquid ratio is 1:20 ~ 1:30, and Extracting temperature is 30 ~ 50 DEG C, and ultrasonic assistant extraction time is 60 ~ 100min, and total flavones yield is higher.Orthogonal and interpretation of result are as shown in table 1,2.
Table 1 Orthogonal experiment results
The variance analysis of table 2 Orthogonal experiment results
Source of error Sum of deviation square Degree of freedom Mean square (MS) F value Significance
A 0.75 2 0.38 1.00 Not remarkable
B 1.29 2 0.65 1.72 Not remarkable
C 5.78 2 2.89 7.70 Significantly
D 1.76 2 0.88 2.35 Not remarkable
Error 0.75 2
F marginal value: F 0.01(1,2)=8.65, F 0.05(1,2)=4.46.
From Orthogonal experiment results and variance analysis, Extracting temperature on the extraction impact of flavones ingredient in seed of Radix Oenotherae erythrosepalae significantly, process conditions concentration of alcohol, solid-liquid ratio, extraction time, on the extraction impact of total flavones in seed of Radix Oenotherae erythrosepalae significantly the primary and secondary order of each factor on total flavones extraction effect impact in seed of Radix Oenotherae erythrosepalae was not: Extracting temperature > extraction time > solid-liquid ratio > concentration of alcohol.Optimal extract process is A 2b 3c 1d 1combination, i.e. volume fraction of ethanol 80%, solid-liquid ratio 1:25, Extracting temperature 30 DEG C, extraction time 60min.
Separation and purification and antioxidant activity detect
(1) polyamide prepolymer process
Polyamide is used industrial soak with ethanol, spends the night the fine powder removing suspension.Wet method dress post after polyamide is fully swelling, the alcoholic solution with 95% carries out eluting, until flow out drop no longer produce muddiness in water.Then use 5%NaOH instead and carry out eluting, extremely neutral with distilled water flushing afterwards, then use 10% acetum eluting, and finally extremely neutral with distilled water punching, wash tasteless, for subsequent use, all to re-start Regeneration Treatment after each loading eluting is complete.
(2) separation and purification
By described extracting solution decompression recycling ethanol containing seed of Radix Oenotherae erythrosepalae flavone and concentrate drying, be dissolved in 40% ethanol, be splined on the polyamide chromatographic column that pretreatment is good, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 3 ~ 6 times of column volumes, collects respectively and drying under reduced pressure, obtains components I, compositionⅱ and component III successively; Compositionⅱ is seed of Radix Oenotherae erythrosepalae total flavones.
(3) determination of total flavonoids and antioxidant activity detect
Take rutin as reference substance, adopt colorimetry to carry out the mensuration of general flavone content, and calculate total flavones yield.Result shows, components I, and II, III yield is respectively 37.25%, 54.73%, 0.76%; Wherein flavone mass fraction is respectively 29.98%, 61.02%, 10.02%, and flavone mainly concentrates in compositionⅱ.The IC of components I 50value is 0.093mg/mL, the IC of compositionⅱ 50value is 0.022mg/mL, the IC of component III 50value is 0.137mg/mL, and under the same terms, vitamin C removes the IC of DPPH free radical 50value is 0.018mg/mL.Gained seed of Radix Oenotherae erythrosepalae flavone of the present invention has significant antioxidant activity.
Following embodiment is shown in concrete preparation:
embodiment 1
The present invention relates to a kind of based on ultrasonic assistant solvent extraction, and adopt polyamide column chromatography separation and purification, obtain the method for seed of Radix Oenotherae erythrosepalae total flavones, comprise the steps:
Step one: extract
Be 1:25 by solid-liquid ratio g/mL, take seed of Radix Oenotherae erythrosepalae dregs of rice ground product, add the alcoholic solution that volume fraction is 80%, setting Extracting temperature is 30 DEG C, and ultrasonic assistant extracts 60 minutes, filters, and obtains solid filter residue and the extracting solution containing seed of Radix Oenotherae erythrosepalae flavone.
Step 2: separation and purification
By described extracting solution decompression recycling ethanol containing seed of Radix Oenotherae erythrosepalae flavone and concentrate drying, be dissolved in 40% ethanol, be splined on the polyamide chromatographic column that pretreatment is good, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 4 times of column volumes, collects respectively and drying under reduced pressure, obtains components I, compositionⅱ and component III successively; Compositionⅱ is seed of Radix Oenotherae erythrosepalae total flavones.
embodiment 2
The present invention relates to a kind of based on ultrasonic assistant solvent extraction, and adopt polyamide column chromatography separation and purification, obtain the method for seed of Radix Oenotherae erythrosepalae total flavones, comprise the steps:
Step one: extract
Be 1:25 by solid-liquid ratio g/mL, take seed of Radix Oenotherae erythrosepalae dregs of rice ground product, add the alcoholic solution that volume fraction is 80%, setting Extracting temperature is 30 DEG C, and ultrasonic assistant extracts 60 minutes, filters, and obtains solid filter residue and the extracting solution containing seed of Radix Oenotherae erythrosepalae flavone.
Step 2: separation and purification
By described extracting solution decompression recycling ethanol containing seed of Radix Oenotherae erythrosepalae flavone and concentrate drying, be dissolved in 40% ethanol, be splined on the polyamide chromatographic column that pretreatment is good, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 5 times of column volumes, collects respectively and drying under reduced pressure, obtains components I, compositionⅱ and component III successively; Compositionⅱ is seed of Radix Oenotherae erythrosepalae total flavones.
Above specific embodiments of the invention are described.It is to be appreciated that the present invention is not limited to above-mentioned particular implementation, those skilled in the art can make various distortion or amendment within the scope of the claims, and this does not affect flesh and blood of the present invention.

Claims (7)

1. a preparation method for seed of Radix Oenotherae erythrosepalae flavone, is characterized in that, described method comprises the steps:
S1, extraction: take the seed of Radix Oenotherae erythrosepalae dregs of rice appropriate, be 1:10 ~ 1:30g/mL by solid-liquid ratio, add the alcoholic solution that volume fraction is 65% ~ 85%, Extracting temperature is set in 30 ~ 70 DEG C, ultrasonic assistant extracts 20 ~ 100 minutes, filter, obtain solid filter residue and the extracting solution containing seed of Radix Oenotherae erythrosepalae flavone;
S2, separation and purification: by described extracting solution decompression recycling ethanol containing seed of Radix Oenotherae erythrosepalae flavone and concentrate drying, be dissolved in 40% ethanol, be splined on the polyamide chromatographic column that pretreatment is good, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 3 ~ 6 times of column volumes, collects respectively and drying under reduced pressure, obtains components I, compositionⅱ and component III successively; Compositionⅱ is seed of Radix Oenotherae erythrosepalae total flavones.
2. the preparation method of seed of Radix Oenotherae erythrosepalae flavone according to claim 1, is characterized in that, in step S1, described solid-liquid ratio is 1:10 ~ 1:30.
3. the preparation method of seed of Radix Oenotherae erythrosepalae flavone according to claim 1, is characterized in that, in step S1, described concentration of alcohol is 65% ~ 85%.
4. the preparation method of seed of Radix Oenotherae erythrosepalae flavone according to claim 1, is characterized in that, in step S1, described Extracting temperature is 30 ~ 70 DEG C.
5. the preparation method of seed of Radix Oenotherae erythrosepalae flavone according to claim 1, is characterized in that, in step S1, described ultrasonic assistant extraction time is 20 ~ 100 minutes.
6. the preparation method of seed of Radix Oenotherae erythrosepalae flavone according to claim 1, is characterized in that, in step S2, the dry thing of the described extraction containing seed of Radix Oenotherae erythrosepalae flavone is with 40% dissolve with ethanol.
7. the preparation method of seed of Radix Oenotherae erythrosepalae flavone according to claim 1, it is characterized in that, in step S2, described 40% alcoholic solution containing seed of Radix Oenotherae erythrosepalae flavone is splined on the good polyamide chromatographic column of pretreatment, successively with 40%, 80% and dehydrated alcohol eluting, elution volume is 3 ~ 6 times of column volumes, collect respectively and drying under reduced pressure, 80% ethanol elution component is seed of Radix Oenotherae erythrosepalae flavone.
CN201510954982.2A 2015-12-17 2015-12-17 Preparation method of evening primrose seed flavone Pending CN105477029A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114053316A (en) * 2021-11-17 2022-02-18 河北大学 Defatted evening primrose seed extract and application thereof
CN116920003A (en) * 2023-08-29 2023-10-24 河北瑞龙生物科技有限公司 Method for extracting total flavonoids from evening primrose

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CN103768106A (en) * 2012-10-25 2014-05-07 奇复康药物研发(苏州)有限公司 Extraction method for semi-pinnated brake herb flavone

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CN1769279A (en) * 2004-10-28 2006-05-10 浙江工业大学 Method for extracting and separating isoflavone from kudzu slag
CN102151296A (en) * 2010-02-11 2011-08-17 兰州大学 Method for extracting active ingredients for reducing sugar blood from waste residues of liquorice
CN103768106A (en) * 2012-10-25 2014-05-07 奇复康药物研发(苏州)有限公司 Extraction method for semi-pinnated brake herb flavone

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114053316A (en) * 2021-11-17 2022-02-18 河北大学 Defatted evening primrose seed extract and application thereof
CN116920003A (en) * 2023-08-29 2023-10-24 河北瑞龙生物科技有限公司 Method for extracting total flavonoids from evening primrose

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