CN112999274A - Rose polyphenol extract and preparation method and application thereof - Google Patents
Rose polyphenol extract and preparation method and application thereof Download PDFInfo
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- CN112999274A CN112999274A CN202110327662.XA CN202110327662A CN112999274A CN 112999274 A CN112999274 A CN 112999274A CN 202110327662 A CN202110327662 A CN 202110327662A CN 112999274 A CN112999274 A CN 112999274A
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- polyphenol extract
- rose
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- ethanol
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Abstract
The invention relates to a rose polyphenol extract and a preparation method and application thereof, wherein the preparation method comprises the following steps: extracting flos Rosae Rugosae with water or alcohol organic solvent, and concentrating to obtain flos Rosae Rugosae concentrated solution; diluting the concentrated solution of flos Rosae Rugosae with water, filtering, adsorbing the filtrate with macroporous adsorbent resin column, sequentially eluting with water, 30-50% ethanol, and 60-80% ethanol, collecting 30-50% ethanol eluate, and concentrating to obtain flos Rosae Rugosae polyphenol extract RA; collecting 60-80% ethanol eluate, and concentrating to obtain rose polyphenol extract RB. The rose polyphenol extract has stable chemical composition and high purity of effective components; the preparation method is simple, convenient and efficient, and is easy to realize industrial application.
Description
Technical Field
The invention relates to the field of chemical component separation, and particularly relates to a rose polyphenol extract and a preparation method and application thereof.
Background
The rose is rich in chemical components, including volatile oil, polyphenol, protein, various amino acids and vitamins, and also rich macroelements, trace elements and other nutritional components essential to human body. The polyphenols are classified into various classes according to their molecular size and carbon skeleton. The polyphenols in flos Rosae Rugosae are mainly flavonoids and tannins. The polyphenol compound contains a plurality of phenolic hydroxyl groups, so that the polyphenol compound has higher biological activity, and meanwhile, the active hydroxyl groups can also cause instability of the structure of the polyphenol compound, thereby bringing difficulty to research.
At present, the application of the rose extract is mainly focused on the application of rose essential oil. The rose essential oil is known as 'liquid gold', and is widely applied to the fields of cosmetics, foods and the like. In the extraction process of the rose essential oil, the generated rose water extract is rich in active substances such as polysaccharide, polyphenol (including flavone, tannin, organic acid and the like) and the like, and is often treated as waste, so that the comprehensive utilization rate of rose is not high, and the rose resource is greatly wasted.
CN109529404B discloses a method for preparing polyphenol extract by using double-petal red rose dregs, which takes the double-petal red rose dregs as raw materials and adopts a plurality of enzyme systems in fruits to extract polyphenol compounds, but the fruit raw materials of the method limit the application of the polyphenol compounds, and the extracted polyphenol substances have lower content; CN105860572A the rose dregs are treated by the steps of ultrasonic countercurrent extraction, resin adsorption separation, nanofiltration membrane filtration dealcoholization and the like, and the pigment, polysaccharide and flavone are obtained by extraction, and the purity of the obtained flavone is only 18.8%.
Plant polyphenol is a main active substance of common food and traditional Chinese medicine, has pharmacological activities in multiple aspects such as oxidation resistance, inflammation resistance, aging resistance and the like, and develops health care products and the like based on polyphenol. Zhanglianli et al (analysis of flavonoids in three rose teas and research on antioxidant activity thereof, journal of Kunming theory university (Nature science edition), 2019-10-15, 44(05):84-90) adopt methanol solutions with different concentrations to extract total flavonoids of three roses of bitter water, golden edge and flat yin and determine the content of the total flavonoids, 30% of methanol extraction obtains golden edge rose tea soup with the highest total flavone content of about 22%, and gradient concentration of methanol extraction only has 4-8% of the total flavone content. Therefore, the polyphenol extract in the rose is not fully utilized.
Disclosure of Invention
In order to solve the technical problems, the invention provides the rose polyphenol extract and the preparation method thereof, and the rose polyphenol extract obtained by the method has stable chemical composition, high purity of pharmacological active ingredients and better effects on oxidation resistance and blood sugar reduction.
The invention relates to a preparation method of a rose polyphenol extract, which comprises the following steps:
(1) extracting flos Rosae Rugosae with water or alcohol organic solvent, and concentrating to obtain flos Rosae Rugosae concentrated solution;
(2) diluting the concentrated solution of flos Rosae Rugosae with water, filtering, adsorbing the filtrate with macroporous adsorbent resin column, sequentially eluting with water, 30-50% ethanol, and 60-80% ethanol, collecting 30-50% ethanol eluate, and concentrating to obtain flos Rosae Rugosae polyphenol extract RA; collecting 60-80% ethanol eluate, and concentrating to obtain rose polyphenol extract RB.
Further, in the step (2), the rose polyphenol extract RA contains quercetin-3-O- β -D-sophoroside and kaempferol-3-O- β -D-sophoroside.
Further, in the step (2), the rose polyphenol extract RB comprises kaempferol-3-O- (6 "-galloyl) - β -D-glucoside and ellagic acid.
Furthermore, the content of quercetin-3-O-beta-D-sophoroside is more than 20% based on the total weight of the rose polyphenol extract RA.
Furthermore, the content of kaempferol-3-O-beta-D-sophoroside is more than 20% based on the total weight of the rose polyphenol extract RA.
Furthermore, the content of kaempferol-3-O- (6' -galloyl) -beta-D-glucoside is more than 8 percent based on the total weight of the rose polyphenol extract RB.
Further, the ellagic acid content is greater than 15% based on the total weight of the rose polyphenol extract RB.
Further, in the step (1), the water extraction method is a steam distillation method.
Further, in the step (1), the alcoholic organic solvent is 50-80% ethanol.
Further, in the step (2), the macroporous adsorption resin is a non-polar resin or a weak polar resin.
The invention claims the rose polyphenol extract prepared by the preparation method.
The invention also claims the application of the rose polyphenol extract in antioxidant and hypoglycemic functional foods or daily chemical products.
By the scheme, the invention at least has the following advantages:
(1) compared with the traditional extraction method, the rose polyphenol extract has higher content and purity of each active ingredient, stable chemical composition, and higher use value of functional food and medicine prepared by taking the active ingredients as raw materials.
(2) The invention separates out flavonoid glycoside and ellagic acid with higher content for the first time, and provides guidance for the application of roses and functional active ingredients thereof in clinic and life.
The foregoing description is only an overview of the technical solutions of the present invention, and in order to make the technical solutions of the present invention more clearly understood and to implement them in accordance with the contents of the description, the following description is made with reference to the preferred embodiments of the present invention and the accompanying detailed drawings.
Drawings
In order that the present disclosure may be more readily and clearly understood, reference will now be made in detail to the present disclosure, examples of which are illustrated in the accompanying drawings.
FIG. 1 is an HPLC profile of the rose polyphenol extract RA prepared in example 2;
FIG. 2 is an HPLC chromatogram of the rose polyphenol extract RB prepared in example 2;
FIG. 3 is an HPLC chromatogram of ellagic acid prepared in example 2;
FIG. 4 is an HPLC chromatogram of an ellagic acid control.
Detailed Description
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Example 1
(1) Weighing 400g of dried rose flower, adding 5L of water, performing reflux extraction for 1 time, combining the two extracting solutions, and concentrating under reduced pressure to 1L; extracting with 1L petroleum ether for 2 times, mixing extractive solutions, and concentrating under reduced pressure to obtain flos Rosae Rugosae essential oil. Adjusting pH of the rest water layer extractive solution to 1-3 with hydrochloric acid, and filtering;
(2) adsorbing the extract obtained in step (1) with AB-8 macroporous adsorbent resin column, eluting with water, 30% and 60% ethanol in sequence, collecting 30% eluate, concentrating, and drying to obtain RA; collecting 60% part of eluate, concentrating, and drying to obtain RB.
And analyzing the composition and the main component content of RA and RB by adopting a liquid phase. Chromatographic conditions are as follows: adopting Agilent 1260 liquid phase system, wherein the chromatographic column is Cosmosil 5C18-PAQ chromatographic column with specification of 4.6mm × 250mm and 5 μm, 0.1% formic acid water is used as mobile phase A, acetonitrile is used as mobile phase B, and thenGradient elution (0-5 min, 5% B, 5-20 min, 5-20% B, 20-30 min, 20% B, 30-45 min, 20-35% B, 45-50 min, 35-80% B, 50-55 min, 80-5% B); the detection wavelength is 360 nm; the column temperature is 30 ℃; flow rate 1ml min-1(ii) a The injection volume was 20. mu.L. HPLC chromatogram is shown in fig. 1 and 2, wherein 1 is quercetin-3-O-beta-D-sophoroside, 2 is kaempferol-3-O-beta-D-sophoroside, 3 is ellagic acid, and 4 is kaempferol-3-O- (6 "-galloyl) -beta-D-glucoside. The content of quercetin-3-O-beta-D-sophoroside in RA is 25% and the content of kaempferol-3-O-beta-D-sophoroside is 23%. The content of kaempferol-3-O- (6' -galloyl) -beta-D-glucoside in RB is 11.2%, and the content of ellagic acid is 22.5%.
Example 2
(1) Weighing 400g of dried rose flower, adding 5L of 80% ethanol, reflux-extracting, repeatedly extracting for 1 time, mixing the two extracting solutions, concentrating under reduced pressure to obtain soft extract, and diluting with water to 1L; extracting with 1L petroleum ether for 2 times, mixing extractive solutions, and concentrating under reduced pressure to obtain flos Rosae Rugosae essential oil. Adjusting pH of the rest water layer extractive solution to 1-3 with hydrochloric acid, and filtering;
(2) adsorbing the extractive solution of (1) with D-101 macroporous adsorbent resin column, sequentially eluting with water, 50% and 80% ethanol, collecting 50% eluate, concentrating, and drying to obtain RA; collecting 80% part of eluate, concentrating, and drying to obtain RB.
And analyzing the composition and the main component content of RA and RB by adopting a liquid phase. The content of quercetin-3-O-beta-D-sophoroside in RA is 32% and the content of kaempferol-3-O-beta-D-sophoroside is 30%. The content of kaempferol-3-O- (6' -galloyl) -beta-D-glucoside in RB is 16.6%, and the content of ellagic acid is 28.2%.
Example 3
Component separation and identification of rose polyphenol extract
(1) RA obtained in example 2 was dissolved in a 30% methanol solution, acetic acid was added at a concentration of 1% v/v, and the solution was passed through an ODS reverse-phase chromatography column, and eluted with 30%, 35%, 40%, 45% and 50% methanol in this order. And (3) combining 35% and 45% of elution fractions through HPLC detection, concentrating, eluting with methanol through a Sephadex LH-20 column, and concentrating to obtain the compound 1. Detecting 50% methanol flow by HPLC, mixing, concentrating, eluting with methanol by Sephadex LH-20 column, and concentrating to obtain compound 2.
(2) RB obtained in example 2 was dissolved in 30% methanol solution, formic acid was added at a concentration of 0.1% v/v, and the solution was passed through an ODS reverse phase chromatography column and eluted with 30%, 35%, 40%, and 60% methanol in this order. And (4) combining and concentrating 40% of elution fractions by HPLC detection to obtain the compound 3. And (3) detecting 60% of the elution fractions by HPLC, merging, concentrating, eluting by a Sephadex LH-20 column with methanol, and concentrating to obtain a compound 4.
Identification of compound 1: yellow powder, ESI-MS (-) gave M/z 625.15([ M-H ]]-). Easily dissolved in methanol, and after thin layer chromatography, dark spots are observed under ultraviolet 254nm, the reaction with aluminum trichloride is yellow, and Molish reaction is positive, so that the flavone glycosides are presumed.1H-NMR(600MHz，MeOH-d4)，δHProton signals of 7.66(1H, s), 7.52(1H, d, J ═ 9.2Hz), 6.87(1H, d, J ═ 8.2Hz), 6.37(1H, s), 6.18(1H, s), the aglycone of which is presumed to be quercetin; deltaHSugar end hydrogen proton signal, δ, of 5.34(1H, d, J ═ 7.6Hz), 4.74(1H, d, J ═ 7.3Hz)H3.83-3.29(12H, m) of hydrogen proton signal on sugar,13C-NMR (600MHz, MeOH-d4) delta: 156.2(C-2), 133.0(C-3), 177.4(C-4), 161.3(C-5), 98.0(C-6), 164.1(C-7), 93.4(C-8), 155.5(C-9), 104.2(C-10), 121.1(C-1'), 115.4(C-2'), 144.8(C-3'), 148.5(C-4'), 116.0(C-5'), 121.8(C-6'), 103.9(C-1 "), 82.7 (C-2"), 76.7(C-3 "), 69.6 (C-4"), 76.5(C-5 "), 60.7 (C-6"), 98.6(C-1 "'), 74.4 (C-2"', 76.5(C-3 "'), 69.5 (C-4"'), 77.5(C-5 "'), 60.6"'). In HMBC spectra, the glucose end group hydrogen proton deltaH4.74 carbon atom signal delta to the 2-position of another glucoseC81.5, determining that the two glucoses are 1-2 connected and are sophorose; the hydrogen proton delta H5.34 at the end group of sophorose is related to the carbon atom signal delta C133.7 at the 3-position of quercetin, and the nuclear magnetic data of the compound 1 is basically consistent with the comparison of the literature [ Zhang Qing Hao et al, sophorae fructus chemical components and the anti-osteoporosis effect research thereof, natural products research and development, 2017, 29(09): 1517-.]Identified as quercetin-3-O-beta-D-sophoroside.
Identification of compound 2: yellow powder, ESI-MS (-) gave M/z 615.11([ M-H ]]-) which is easy to dissolve in methanol, and is observed under ultraviolet 254nm after thin-layer chromatography to have dark spots, and the reaction with aluminum trichloride shows yellow, and the Molish reaction shows positive, so that the flavonoid glycoside substance is presumed to be the flavonoid glycoside substance.1H-NMR(600MHz，MeOH-d4)，δHProton signals of 8.03(2H, d, J ═ 8.3Hz), 6.89(2H, d, J ═ 8.3Hz), 6.38(1H, s), 6.18(1H, s), and the aglycone of the compound was presumed to be kaempferol; deltaHSugar end hydrogen proton signal, δ, of 5.31(1H, d, J ═ 7.5Hz), 4.76(1H, d, J ═ 7.5Hz)H3.84-3.31(12H, m) of hydrogen proton signal on sugar,13C-NMR (600MHz, MeOH-d4) delta: 156.3(C-2), 132.9(C-3), 177.5(C-4), 161.3(C-5), 98.7(C-6), 164.1(C-7), 93.6(C-8), 155.6(C-9), 103.9(C-10), 120.9(C-1'), 131.0(C-2', 6'), 115.3(C-3', 5'), 160.0(C-4'), 97.9(C-1 "), 82.5 (C-2"), 77.5(C-3 "), 69.7 (C-4"), 77.0(C-5 "), 60.8 (C-6"), 104.1(C-1 "'), 74.4 (C-2"'), 76.7(C-3 "'), 69.6 (C-4"'), 76.6(C-5 "'), 60.5 (C-6"'). In HMBC spectra, the glucose end group hydrogen proton deltaH4.76 signal delta from the carbon atom at position 2 of another glucoseC81.2, determining that the two glucoses are 1-2 connected and are sophorose; hydrogen proton delta at sophorose end groupH5.31 signal delta with the 3-carbon atom of kaempferolC133.6. The nuclear magnetic data of the compound 2 is basically consistent with the comparison of the literature [ Zhang Qing Hao et al, chemical components of fructus sophorae and the research on the anti-osteoporosis effect thereof, natural product research and development, 2017, 29(09): 1517-.]Identified as kaempferol-3-O-beta-D-sophoroside.
Identification of Compound 4: yellow powder, ESI-MS (-) gave M/z 600.48([ M-H ]]-) which is easy to dissolve in methanol, and is observed under ultraviolet 254nm after thin-layer chromatography to have dark spots, and the reaction with aluminum trichloride shows yellow, and the Molish reaction shows positive, so that the flavonoid glycoside substance is presumed to be the flavonoid glycoside substance.1H-NMR(400MHz，DMSO-d6)：δ7.94(d，J＝8.6Hz，2H，H-2'，6')，6.92(s，2H，H-2”'，6”')，6.76(d，J＝8.5Hz，2H，H-3'，5')，6.39(d，J＝2.1Hz，1H，H-8)，6.19(d，J＝2.1Hz，1H，H-6)，5.45(d，J＝7.3Hz，1H，glu-H-1”)，4.26(d，J＝11.6Hz，1H，4.17(dd，J＝12.0，3.3Hz，1H)，3.49～3.35(m，2H)，3.27(tt，J＝14.3，7.2Hz，2H)。13C-NMR (100MHz, DMSO-d6) delta: 177.7(C-4), 166.1(C-7), 161.6(C-5), 160.4(C-4'), 157.2(C-9), 156.2(C-2), 133.6(C-3), 131.2(C-2', 6'), 119.7(C-1'), 115.6(C-3', 5'), 104.3(C-10), 99.4(C-6), 94.3(C-8), glucose: 101.8(C-1 "), 75.5 (C-2"), 74.9(C-3 "), 76.8 (C-5"), 69.5(C-4 "), 63.1 (C-6"), galloyl: 165.1(C-7 '), 145.9(C-3 ', 5'), 138.9(C-4 '), 121.1(C-1'), 109.0(C-2 ', 6 '). The nuclear magnetic data of compound 4 is substantially consistent with literature comparison [ Zhangpei et al. chemical composition of China rose. Chinese herbal medicine 2010, 41(10):1616-1618.]Identified as kaempferol-3-O- (6' -galloyl) -beta-D-glucoside.
Structural characterization of compound 3:
HPLC comparison with ellagic acid reference purchased from sahn chemical technology (shanghai) ltd, chromatographic conditions: isocratically eluting with methanol-0.1% formic acid water solution (57: 43) for 20min, and detecting the wavelength at 254nm under the same chromatographic conditions as in example 1. FIG. 3 is a liquid phase diagram of ellagic acid prepared in the present example, and FIG. 4 is a liquid phase diagram of a control. T of comparison of two figuresRSimilarly, the compound is ellagic acid.
Comparative example
(1) Weighing 400g of dried rose flower, adding 4L of methanol for reflux extraction, repeatedly extracting for 1 time, combining the two extracting solutions, concentrating under reduced pressure to obtain thick paste, and adding water for diluting to 1L; extracting with 1L petroleum ether for 2 times, mixing extractive solutions, and concentrating under reduced pressure to obtain flos Rosae Rugosae essential oil. Adjusting pH of the rest water layer extractive solution to 1-3 with hydrochloric acid, and filtering;
(2) extracting the extractive solution of (1) with 1L ethyl acetate, repeating the extraction for 3 times, mixing extractive solutions, concentrating under reduced pressure, and drying to obtain RB. Concentrating the rest water layer extractive solution under reduced pressure, and drying to obtain RA.
Content comparison of rose polyphenol extract:
the contents of the rose polyphenol extracts prepared in examples 1 and 2 and comparative example are shown in table 1.
TABLE 1 content of different rose polyphenol extracts
The antioxidant and hypoglycemic effects of the rose polyphenol extract are compared:
OH of the rose polyphenol extracts prepared in example 1 and comparative example was measured·Clearance, DPPH·Clearance rate and alpha-glucosidase inhibitory activity.
(1) Preparing each group of sample solution by using 70% ethanol solution, preparing reference substance solution with the same concentration by using VC as a standard substance, taking 1ml of each sample, replacing the sample solution by using 1ml of 70% ethanol solution in a blank group, adding 2ml of 1 mu mol/ml-1 DPPH ethanol solution, fully mixing uniformly, reacting for 30min in a dark place at room temperature, measuring absorbance at 515nm, parallelly measuring three groups, and taking an average value.
(2) Adding 6mmol/L FeSO in turn4The solution, 6mmol/L salicylic acid solution each 2ml, 2ml sample was added, and finally 6mmol/L H was added2O2Starting the reaction with 2ml of the solution, standing for 30min, measuring the absorbance at the wavelength of 510nm, replacing the sample solution with distilled water as a blank, taking VC with the same mass concentration as a positive control, carrying out parallel determination for three times, and taking an average value.
(3) Respectively taking 100 μ l of each sample, adding 450 μ l of buffer solution, adding 200 μ l of alpha-glucosidase solution, adding 200 μ l of PNPG after water bath at 37 ℃ for 15min, adding 2ml of Na with the concentration of 0.5mol/l after water bath at 37 ℃ for 30min2CO3The reaction was terminated and the absorbance at 405nm was measured. Using phosphate buffer solution as blank control instead of enzyme solution and sample solution, and using phosphorusReplacing the sample with acid buffer solution as negative control, replacing the sample with acarbose solution as positive control, and making into final product
The results are shown in Table 2.
TABLE 2 antioxidant and hypoglycemic effects of rose polyphenol extract
As can be seen from table 1, the content of the rose polyphenol extract prepared by the present invention is much higher than that of the rose polyphenol extract prepared by the conventional method, and in table 2, the 1, 1-diphenyl-2-picrylphenylhydrazine (DPPH) clearance rate, the hydroxyl radical clearance rate and the α -glucosidase inhibitory activity of the rose polyphenol extract prepared by the present invention are all more than 2 times those of the rose polyphenol extract prepared by the conventional method, which indicates that the extract of the present invention has higher effective active component content and stronger antioxidant and hypoglycemic effects.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the spirit or scope of the invention.
Claims (10)
1. The preparation method of the rose polyphenol extract is characterized by comprising the following steps:
(1) extracting flos Rosae Rugosae with water or alcohol organic solvent, and concentrating to obtain flos Rosae Rugosae concentrated solution;
(2) diluting the concentrated solution of flos Rosae Rugosae with water, filtering, adsorbing the filtrate with macroporous adsorbent resin column, sequentially eluting with water, 30-50% ethanol, and 60-80% ethanol, collecting 30-50% ethanol eluate, and concentrating to obtain flos Rosae Rugosae polyphenol extract RA; collecting 60-80% ethanol eluate, and concentrating to obtain rose polyphenol extract RB.
2. The method of claim 1, wherein: in the step (2), the rose polyphenol extract RA contains quercetin-3-O-beta-D-sophoroside and kaempferol-3-O-beta-D-sophoroside.
3. The method of claim 1, wherein: in the step (2), the rose polyphenol extract RB comprises kaempferol-3-O- (6' -galloyl) -beta-D-glucoside and ellagic acid.
4. The method of claim 2, wherein: in the rose polyphenol extract RA, the content of quercetin-3-O-beta-D-sophoroside is more than 20%, and the content of kaempferol-3-O-beta-D-sophoroside is more than 20%.
5. The production method according to claim 3, characterized in that: in the rose polyphenol extract RB, the content of kaempferol-3-O- (6' -galloyl) -beta-D-glucoside is more than 8 percent, and the content of ellagic acid is more than 15 percent.
6. The method of claim 1, wherein: in the step (1), the water extraction method is a steam distillation method.
7. The method of claim 1, wherein: in the step (1), the alcohol organic solvent is 50-80% ethanol.
8. The method of claim 1, wherein: in the step (2), the macroporous adsorption resin is nonpolar resin or weak polar resin.
9. A rose polyphenol extract produced by the production method described in any one of claims 1 to 8.
10. Use of the rose polyphenol extract of claim 9 in an antioxidant and hypoglycemic functional food or daily chemical product.
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Cited By (3)
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| CN113484434A (en) * | 2021-07-01 | 2021-10-08 | 苏州求是本草健康科技有限公司 | Detection method of rose polyphenol |
| CN113717139A (en) * | 2021-09-15 | 2021-11-30 | 耒阳市刘燕酿制生物科技有限公司 | Method for extracting quercetin from pomegranate peel |
| CN116712484A (en) * | 2023-07-03 | 2023-09-08 | 暨南大学 | Rose extract, preparation method thereof and application thereof in preparation of drugs with neuraminidase inhibition effect |
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| CN106668234A (en) * | 2016-12-30 | 2017-05-17 | 成都普思生物科技股份有限公司 | Process for extracting and purifying total flavone from rose flower |
| CN110638704A (en) * | 2019-10-11 | 2020-01-03 | 广东丸美生物技术股份有限公司 | Extraction method of rose extract, rose extract obtained by extraction, application and cosmetics |
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| CN101693059A (en) * | 2009-10-16 | 2010-04-14 | 中国科学院新疆理化技术研究所 | Preparation method of rose polyphenol and application thereof in gynaecology and obstetrics |
| CN106668234A (en) * | 2016-12-30 | 2017-05-17 | 成都普思生物科技股份有限公司 | Process for extracting and purifying total flavone from rose flower |
| CN110638704A (en) * | 2019-10-11 | 2020-01-03 | 广东丸美生物技术股份有限公司 | Extraction method of rose extract, rose extract obtained by extraction, application and cosmetics |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113484434A (en) * | 2021-07-01 | 2021-10-08 | 苏州求是本草健康科技有限公司 | Detection method of rose polyphenol |
| CN113717139A (en) * | 2021-09-15 | 2021-11-30 | 耒阳市刘燕酿制生物科技有限公司 | Method for extracting quercetin from pomegranate peel |
| CN116712484A (en) * | 2023-07-03 | 2023-09-08 | 暨南大学 | Rose extract, preparation method thereof and application thereof in preparation of drugs with neuraminidase inhibition effect |
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