CN112870236B - Flavone effective part of abelmoschus manihot and preparation method and application thereof - Google Patents
Flavone effective part of abelmoschus manihot and preparation method and application thereof Download PDFInfo
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- CN112870236B CN112870236B CN202011353570.0A CN202011353570A CN112870236B CN 112870236 B CN112870236 B CN 112870236B CN 202011353570 A CN202011353570 A CN 202011353570A CN 112870236 B CN112870236 B CN 112870236B
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- ethanol
- quercetin
- macroporous resin
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- 240000005959 Abelmoschus manihot Species 0.000 title claims abstract description 63
- 235000001075 Abelmoschus manihot Nutrition 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 229930003944 flavone Natural products 0.000 title claims description 23
- 235000011949 flavones Nutrition 0.000 title claims description 23
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 title description 13
- 150000002212 flavone derivatives Chemical class 0.000 title description 13
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title description 13
- 229930003935 flavonoid Natural products 0.000 claims abstract description 39
- 235000017173 flavonoids Nutrition 0.000 claims abstract description 39
- 150000002215 flavonoids Chemical class 0.000 claims abstract description 34
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 claims abstract description 26
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims abstract description 26
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- YLWQTYZKYGNKPI-CXWQUDHASA-N 3,5,7-trihydroxy-2-[4-hydroxy-3-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OC1=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=CC=C1O YLWQTYZKYGNKPI-CXWQUDHASA-N 0.000 claims abstract description 13
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims abstract description 13
- KHVMAMXQPVHXTJ-UHFFFAOYSA-N Hibifolin-acetat Natural products O1C(C(O)=O)C(O)C(O)C(O)C1OC1=C(O)C=C(O)C2=C1OC(C=1C=C(O)C(O)=CC=1)=C(O)C2=O KHVMAMXQPVHXTJ-UHFFFAOYSA-N 0.000 claims abstract description 13
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- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims abstract description 13
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- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims abstract description 13
- HCUDCIHFJUTKCF-UHFFFAOYSA-N gossypetin 8-O-beta-D-glucuronide Natural products OC1C(O)C(Oc2c(O)c(O)c(O)c3C(=O)C=C(Oc23)c4ccc(O)c(O)c4)OC(C1O)C(=O)O HCUDCIHFJUTKCF-UHFFFAOYSA-N 0.000 claims abstract description 13
- GXMWXESSGGEWEM-UHFFFAOYSA-N isoquercitrin Natural products OCC(O)C1OC(OC2C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O GXMWXESSGGEWEM-UHFFFAOYSA-N 0.000 claims abstract description 13
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims abstract description 13
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 claims abstract description 13
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- OVSQVDMCBVZWGM-DTGCRPNFSA-N quercetin 3-O-beta-D-galactopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-DTGCRPNFSA-N 0.000 claims abstract description 13
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 claims abstract description 13
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims abstract description 13
- BBFYUPYFXSSMNV-UHFFFAOYSA-N quercetin-7-o-galactoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 BBFYUPYFXSSMNV-UHFFFAOYSA-N 0.000 claims abstract description 13
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention relates to an effective part of abelmoschus manihot flavonoid as well as a preparation method and application thereof, belonging to the field of medicines, and the effective part of the abelmoschus manihot flavonoid comprises the following flavonoid components: the effective part of the abelmoschus manihot flavonoid has good effects of preventing or treating skin aging, repairing and resisting aging, and the effective part of the abelmoschus manihot flavonoid has the advantages of good effects of preventing or treating skin aging, repairing and resisting aging, and can be used for treating skin aging, and preventing and treating skin aging, and is prepared from quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperin in a mass ratio of 1:13-33:1-7:14-38:12-32:1-5: 18-42.
Description
Technical Field
The invention belongs to the field of medicines, particularly relates to a flavonoid effective part of abelmoschus manihot and a preparation method and application thereof, and particularly relates to a high-purity flavonoid effective part of abelmoschus manihot prepared by a membrane separation coupling resin method and application thereof.
Background
Abelmoschus manihot (L.) Medic, a dry corolla of Abelmoschus manihot (L.) Medic) belonging to family Malvaceae, is sweet and cold in taste and enters kidney and bladder meridians; has effects of clearing away heat and dampness, relieving swelling, and removing toxic substances, and can be used for treating superficial infection, toxic swelling, and scald caused by water or fire. The medicine is recorded in Jiayou materia Medica, and the Chinese pharmacopoeia of 2010 edition. Record of Jiayou herbal: abelmoschus manihot is used for treating malignant sores and abscess for a long time without recovery. The compendium of materia Medica (Ben Cao gang mu) is characterized in that: abelmoschus manihot, flos Abelmoschi Manihot, with sweet, cold, slippery and non-toxic smell, is used as a key herb for treating sore when patients with malignant sores and pus are not healed for a long time.
According to the research results of published documents, the flavonoid compound is the main component of the flower of abelmoschus manihot and is also the pharmacological active component of the flower of abelmoschus manihot, and the flower of abelmoschus manihot total flavone can improve the renal function and has obvious curative effect on treating chronic glomerulonephritis. Modern researches prove that the flavonoid components in the abelmoschus manihot extract not only have obvious treatment effect on sores, but also have obvious protection effect on injuries of heart, brain, tissues and the like caused by ischemia; in addition, researches show that the sunset abelmoschus flower total flavone has certain effects on controlling intestinal inflammation, reducing histopathological scores and the like, wherein the kidney tissue inflammation factor level is reduced through dose group therapy in the sunset abelmoschus flower total flavone, and free radicals of organisms are eliminated at the same time, so that the sunset abelmoschus flower total flavone is expected to become a medicine for treating chronic glomerulonephritis. A plurality of literature reports show that the sunset abelmoschus flower total flavone has better effects on the aspects of resisting inflammation, relieving fever and pain, protecting heart and brain ischemia injury, promoting angiogenesis, reducing thrombus, reducing blood sugar, resisting virus, resisting depression and the like. In addition, in recent years, the main development trend of cosmetics in all countries in the world is to "advocate nature", and natural plant raw materials are favored. The flavonoid compounds are widely existed in the plant world, and many of the flavonoid compounds have the effects of clearing free radicals in skin, promoting skin metabolism, reducing pigmentation, moistening skin, astringing, moisturizing, removing red blood streak and the like, but at present, cosmetics added with the plant flavonoid compounds are still in the research and development stage.
The extraction method of the flower of abelmoschus manihot reported in the literature comprises ethanol reflux extraction, ultrasonic extraction and normal-temperature soaking extraction, for example, Chinese patent application 201510916167.7 discloses an extraction process of flavonoid compounds in the flower of abelmoschus manihot, which comprises the following steps: drying flos Abelmoschi Manihot flower, pulverizing, sieving, adding ethanol, ultrasonic extracting, centrifuging, collecting supernatant, and filtering. For another example, chinese patent application 201911306130.7 discloses an extract of flower of abelmoschus manihot and a preparation method thereof, the preparation method comprising the steps of: (1) extraction: weighing raw material abelmoschus manihot, adding 60-80% ethanol for reflux extraction; (2) filtering for the first time: filtering to obtain filtrate; (3) and (3) concentrating: concentrating the filtrate under reduced pressure to obtain concentrated solution a without alcohol smell, and recovering ethanol; (4) water precipitation: adding water into the concentrated solution a for water precipitation; (5) and (3) second filtration: filtering to obtain supernatant; (6) adsorption: adsorbing the supernatant with macroporous resin; (7) impurity washing: washing impurities with water; (8) desorption: desorbing by using 65-75% ethanol to obtain desorption solution; (9) concentration: concentrating the desorption solution under reduced pressure to obtain concentrated solution b, wherein the Baume degree is 10-20; (10) and (3) drying: and transferring the concentrated solution b to a spraying process for spraying to obtain the product. The Abelmoschus manihot flower extract has good hygroscopicity. The preparation process is safer, more efficient and more environment-friendly.
However, the sunset abelmoschus flower extract has complex components, the content of active ingredients is greatly changed, different content compositions generally have great influence on the pharmacological action of the sunset abelmoschus flower extract, but the actual research of the sunset abelmoschus flower extract in cosmetics is relatively deficient at present, the extraction transfer rate is low, the extraction energy consumption is high, and the solvent dosage is large. Therefore, there is a need to search for effective fractions of sunscreens for cosmetics, particularly for preventing or treating skin aging, or anti-aging cosmetics, and extraction processes thereof.
Disclosure of Invention
The invention aims to provide an effective part of flavones of abelmoschus manihot and a preparation method and application thereof, and provides the effective part of flavones of abelmoschus manihot and an extraction process thereof aiming at cosmetics, in particular sunscreens, after-sun repairing agents or anti-aging cosmetics for preventing or treating skin aging.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
firstly, the invention provides an effective part of flavones of abelmoschus manihot, which comprises the following flavones: quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperin, wherein the mass ratio of the components is 1:13-33:1-7:14-38:12-32:1-5:18-42, preferably 1:15-32:2-6:16-36:14-30:2-4: 20-40; preferably 1:17-29:2.4-5.2:18-33:16-27:2.4-3.6: 23-38; further preferably 1:19-26:2.7-4.4:20-29:18-24:2.7-3.3: 26-35.
Preferably, the content of quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperoside in the effective part is 52% or more, preferably 56% or more, more preferably 63-77%, and even more preferably 67-75%. Furthermore, the invention provides a pharmaceutical composition comprising the effective part, and the pharmaceutical composition further comprises a pharmaceutically acceptable carrier.
Preferably, the dosage form of the pharmaceutical composition comprises solution, injection, tablet, suppository, ointment, gel, pill, granule, capsule, mixture and suspension.
Furthermore, the invention provides a composition comprising the following flavonoid ingredients: quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperoside, wherein the mass ratio of the components is 1:13-33:1-7:14-38:12-32:1-5:18-42, preferably 1:15-32:2-6:16-36:14-30:2-4:20-40, more preferably 1:17-29:2.4-5.2:18-33:16-27:2.4-3.6:23-38, and even more preferably 1:19-26:2.7-4.4:20-29:18-24:2.7-3.3: 26-35.
Preferably, in the composition, the content of quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperoside is 52% or more, preferably 56% or more, more preferably 63-77%, and still more preferably 67-75%.
Furthermore, the present invention provides the use of the above-mentioned effective fraction, pharmaceutical composition or composition for the preparation of a sunscreen agent, a post-sun repair agent or an anti-aging cosmetic for the prevention or treatment of skin aging.
Furthermore, the invention provides application of the effective part, the pharmaceutical composition or the composition in preparing anti-aging drugs.
Furthermore, the invention provides a preparation method of the effective part, and particularly provides a method for preparing high-purity flavone components of the abelmoschus manihot by a membrane separation coupling resin method. The method comprises the steps of gradually separating total flavonoids from the flower of abelmoschus manihot by using an ultrafiltration membrane and macroporous resin, extracting the flower of abelmoschus manihot by using ethanol, primarily treating an extracting solution, filtering by using ultrafiltration membranes with different molecular weight cut-off to obtain a concentrated solution, recovering the ethanol from the concentrated solution, and treating by using the macroporous resin to obtain the high-purity effective flavonoid fraction of the flower of abelmoschus manihot.
The preparation method comprises the following steps:
(1) extracting flos Abelmoschi Manihot with ethanol to obtain extractive solution; (2) the extract is filtered in series by two ultrafiltration membranes with different molecular weight cut-offs to prepare a cut-off concentrated solution; (3) removing ethanol from the concentrated solution, and eluting with macroporous resin to obtain effective fraction of flos Abelmoschi Manihot flower flavonoids.
In a preferred embodiment of the method of the invention,
in the step (1), the dosage of the ethanol is 10-25 times of that of the flower of abelmoschus manihot, the ethanol is 60% -95% ethanol solution, and the extraction method can adopt the extraction method used in the field, including but not limited to a reflux method or a percolation method;
in step (2), the molecular weights are 300-3500, and more preferably the two molecular weight cutoffs are 500 and 3500, respectively; the filtering volume of the filtration is 50-90% of the extracting solution, and the preferred filtering volume is 70-80%;
in the step (2), before filtering, the method further comprises the steps of extracting the extracting solution, adsorbing with activated carbon, precipitating with alcohol or precipitating with acid, wherein the solvent for precipitating with alcohol is preferably ethanol or methanol, and the solvent for precipitating with acid is preferably hydrochloric acid or sulfuric acid.
In the step (3), the model of the macroporous resin is D101, HPD100 or AB-8, and the ethanol removal is the decompression recovery of ethanol at the temperature of 50-90 ℃;
in the step (3), the elution process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:6, the concentration of a sample loading solution is 0.15g crude drug/ml, the volume of the sample loading solution is 7BV, the sample loading is carried out at the flow rate of 2BV/h, the impurities are removed by using 6BV pure water and 3BV 5% ethanol at the flow rate of 2BV/h, and the elution is carried out by using 4BV 60% ethanol at the flow rate of 2 BV/h. The sample loading liquid takes water as a solvent.
Further preferably, the preparation method provided by the invention comprises the following specific operation steps:
(1) extracting Abelmoschus manihot with 10-25 times of 60% -95% ethanol to obtain Abelmoschus manihot extract;
(2) primarily treating the abelmoschus manihot extract, and filtering with ultrafiltration membranes with different molecular weight cut-off, wherein the primary treatment method comprises extraction, activated carbon adsorption, alcohol precipitation or acid precipitation and the like;
(3) selecting ultrafiltration membranes with cut-off molecular weight of 500-3500, using the ultrafiltration membranes with different molecular weights in series, filtering 50-90% of the volume of the extract by using the ultrafiltration membranes to obtain concentrated solution, recovering ethanol from the concentrated solution at 50-90 ℃ under reduced pressure, and treating the ethanol by using macroporous resin to obtain the flavonoid effective part of the flower of abelmoschus manihot, wherein the type of the macroporous resin 1:6 is D101, HPD100 or Ab-8;
(4) the treatment process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:4-1:9, the concentration of a sample loading solution is 0.10-0.30g crude drug/ml, the volume of the sample loading solution is 4-12BV, sample loading is carried out at the flow rate of 1-4BV/h, impurity removal is carried out by using 4-8BV pure water and 1-5BV5% ethanol at the flow rate of 0.5-4BV/h, and elution is carried out by using 2-8BV 60% ethanol at the flow rate of 1-5 BV/h;
(5) recovering ethanol from macroporous resin eluate at 50-90 deg.C under reduced pressure to obtain flos Abelmoschi Manihot flower flavonoid effective fraction.
Still more preferably as follows:
(1) extracting Abelmoschus manihot with 15-18 times of 60% -70% ethanol to obtain Abelmoschus manihot extract;
(2) primarily treating the abelmoschus manihot extract, and filtering with ultrafiltration membranes with different molecular weight cut-off, wherein the primary treatment method comprises extraction, activated carbon adsorption, alcohol precipitation or acid precipitation and the like;
(3) selecting ultrafiltration membranes with the cut-off molecular weight of 500-3500, connecting the ultrafiltration membranes with different molecular weights in series for use, filtering 70-90% of the volume of an extracting solution by using the ultrafiltration membranes to obtain a concentrated solution, recovering ethanol from the concentrated solution at 50-70 ℃ under reduced pressure, and treating the concentrated solution by using D101 macroporous resin to obtain the flavonoid effective part of the flower of abelmoschus manihot;
(4) the treatment process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:5-1:8, the concentration of a sample loading solution is 0.10-0.20g crude drug/ml, the volume of the sample loading solution is 5-10BV, the sample loading is carried out at the flow rate of 1-3BV/h, 5-7BV pure water and 2-4BV 5% ethanol are used for removing impurities at the flow rate of 1-3BV/h, and 3-6BV 60% ethanol is used for eluting at the flow rate of 1-4 BV/h;
(5) recovering ethanol from macroporous resin eluate at 50-70 deg.C under reduced pressure to obtain flos Abelmoschi Manihot flavone effective fraction.
The beneficial effects of the invention are as follows:
(1) the flavonoid effective part of the abelmoschus manihot has good effects of preventing or treating sun screening and repairing after solarization;
(2) the flavonoid effective part of the abelmoschus manihot has good anti-aging effect;
(3) the preparation method has the advantages of simple process, short production period, mild treatment conditions, low energy consumption, good separation effect of the 7 flavonoid components of the flower of abelmoschus manihot, wide sources of the used raw materials and reagents, low cost and easy realization of industrial large-scale production.
Detailed Description
The present invention will be further explained with reference to specific examples in order to make the technical means, the technical features, the technical objectives and the effects of the present invention easier to understand, but the following examples are only preferred embodiments of the present invention, and not all embodiments of the present invention. Other embodiments obtained by persons skilled in the art without making creative efforts based on the embodiments in the implementation belong to the protection scope of the invention. In the following examples, unless otherwise specified, all the procedures and equipment used were conventional equipment.
Example 1 preparation of flavonoid effective fractions from Abelmoschus manihot
Pulverizing 100g flos Abelmoschi Manihot into coarse powder, and extracting with 15 times of 60% ethanol under reflux to obtain extractive solution; adsorbing the abelmoschus manihot extract by using activated carbon, filtering by using an ultrafiltration membrane with the molecular weight cutoff of 3500, collecting filtrate, filtering 80% of the filtrate by using an ultrafiltration membrane with the molecular weight cutoff of 500 to obtain concentrated solution, recovering ethanol from the concentrated solution at 50 ℃ under reduced pressure, and treating by using D101 macroporous resin, wherein the treatment process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:6, the concentration of a sample loading solution (aqueous solution) is 0.15g crude drug/ml, the volume of the sample loading solution is 7BV, sample loading is carried out at the flow rate of 2BV/h, impurities are successively removed by 6BV pure water and 3BV 5% ethanol at the flow rate of 2BV/h, elution is carried out by 4BV 60% ethanol at the flow rate of 2BV/h to obtain an eluent, and the eluent is decompressed and recycled at the temperature of 50 ℃ to obtain 1.23g of the effective part of the flower flavonoid of abelmoschus manihot.
Example 2 preparation of effective fractions of sunset abelmoschus flowers
Pulverizing 100g flos Abelmoschi Manihot into coarse powder, and extracting with 18 times of 70% ethanol under reflux to obtain extractive solution; filtering the abelmoschus manihot extract by using an ultrafiltration membrane with molecular weight cutoff of 3500, collecting filtrate, filtering 70% of the filtrate by using an ultrafiltration membrane with molecular weight cutoff of 1000 to obtain concentrated solution, recovering ethanol from the concentrated solution at 60 ℃ under reduced pressure, and treating the concentrated solution by using D101 macroporous resin, wherein the treatment process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:5, the concentration of a sample loading solution is 0.15g crude drug/ml, the volume of the sample loading solution is 6BV, sample loading is carried out at the flow rate of 2BV/h, impurities are removed by 6BV pure water and 3BV 5% ethanol at the flow rate of 2BV/h, elution is carried out by 4BV 60% ethanol at the flow rate of 1.5BV/h to obtain an eluent, and the eluent is decompressed and recycled at the temperature of 60 ℃ to obtain 1.19g of the effective part of the abelmoschus manihot flavonoids.
Example 3 preparation of effective fractions of sunset abelmoschus flowers
Pulverizing 100g flos Abelmoschi Manihot into coarse powder, percolating with 18 times of 60% ethanol, and extracting to obtain extractive solution; filtering the abelmoschus manihot extract by using an ultrafiltration membrane with the molecular weight cutoff of 3500, collecting filtrate, filtering 80% of the filtrate by using an ultrafiltration membrane with the molecular weight cutoff of 500 to obtain concentrated solution, recovering ethanol from the concentrated solution at 60 ℃ under reduced pressure, and treating the concentrated solution by using D101 macroporous resin, wherein the treatment process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:8, the concentration of a sample loading solution is 0.15g crude drug/ml, the volume of the sample loading solution is 8BV, sample loading is carried out at the flow rate of 2BV/h, impurities are removed by using 6BV pure water and 3BV 5% ethanol at the flow rate of 2BV/h, elution is carried out by using 4BV 60% ethanol at the flow rate of 3BV/h to obtain an eluent, and the eluent is decompressed at the temperature of 60 ℃ to recover the ethanol to obtain 0.98g of the effective part of the flower flavonoid of abelmoschus manihot.
Example 4 preparation of effective fractions of sunset abelmoschus flowers
Percolating 100g flos Abelmoschi Manihot with 18 times of 70% ethanol to obtain extractive solution; filtering the abelmoschus manihot extract by using an ultrafiltration membrane with molecular weight cutoff of 3500, collecting filtrate, filtering 80% of the filtrate by using an ultrafiltration membrane with molecular weight cutoff of 1000, washing the liquid in a charging basket by using 70% ethanol, washing 3 times of the volume of the liquid to obtain concentrated solution, recovering ethanol from the concentrated solution at 60 ℃ under reduced pressure, and treating the concentrated solution by using D101 macroporous resin, wherein the treatment process of the macroporous resin comprises the following steps: the macroporous resin diameter-height ratio is 1:6, the concentration of a sample loading solution is 0.15g crude drug/ml, the volume of the sample loading solution is 7BV, the sample loading is carried out at the flow rate of 2BV/h, 6BV pure water and 3BV 5% ethanol are used for removing impurities at the flow rate of 2BV/h, 4BV 60% ethanol is used for eluting at the flow rate of 2BV/h to obtain an eluent, and the eluent is decompressed at 60 ℃ to recover the ethanol to obtain 1.25g of the flavones effective part of the abelmoschus manihot.
Example 5 detection of effective part of Abelmoschus manihot flavonoid
The content of 7 ingredients was measured on the effective fractions of sunset abelmoschus flower flavonoid prepared in examples 1 to 4. The detection method adopts a UPLC method reported in the determination of 7 ingredients in the flower of abelmoschus manihot by a one-test-multiple evaluation method (journal of drug analysis, 12 th 2013, 2082-step 2087) to determine the content of the ingredients in the flower of abelmoschus manihot.
The detection results of the components in the sample are shown in tables 1 to 4:
TABLE 1 assay data for the sample of example 1
TABLE 2 assay data for the sample of example 2
TABLE 3 assay data for the samples of example 3
TABLE 4 assay data for the samples of example 4
Example 6 prevention of UVB-induced skin Damage in mice by effective fractions of Abelmoschus manihot flavonoid
The experimental method comprises the following steps:
BALB/c mice, weight 22 + -2 g, light/dark cycle 12 h. When UVB irradiates, a 313nm UVB lamp tube 4 is used for manufacturing an ultraviolet lamp box, the irradiation height is adjusted to be 20cm, 2 hours of irradiation are carried out every day, and the irradiation lasts for four weeks.
Randomly dividing the test result into a control group, a light aging model group, an abelmoschus manihot flavonoid effective part prevention group, an abelmoschus manihot flavonoid effective part treatment group and an abelmoschus manihot extract control group according to the weight, wherein each group comprises 6 patients. Wherein the effective part of the flavones of the flower of abelmoschus manihot is obtained by the preparation method of the embodiment 3,abelmoschus manihot extract was prepared according to document CN108567802A example 3. After grouping, the back of each group of mice is depilated until the skin is completely exposed, and the depilated area is 6-8cm 2 。
Control group, without UVB irradiation, was directly applied with physiological saline (0.1 mL/cm) 2 ) (ii) a A light aging model group, wherein the back of the mouse after depilation is irradiated by a UVB lamp; the effective part prevention group of flos Abelmoschi Manihot flavone is prepared by smearing effective part solution of flos Abelmoschi Manihot flavone (active ingredient: 0.05 mg/cm) 1 hr before each UVB irradiation 2 ) (ii) a The flos Abelmoschi Manihot flavone effective part treatment group is smeared with flos Abelmoschi Manihot flavone effective part solution (active ingredient 0.05 mg/cm) 1 hr after each UVB irradiation 2 ) (ii) a The flos Abelmoschi Manihot extract treatment group is applied with flos Abelmoschi Manihot extract solution (active ingredient 0.15 mg/cm) 1 hr after each UVB irradiation 2 )。
After the experiment is finished, the skin of the back of each group of mice is photographed by using a digital camera, and the damage degree of the skin of the back of the mice is observed and analyzed.
The results of the experiment are shown in table 5:
table 5.
Experimental results show that the effective part of the flavones of the abelmoschus manihot can effectively prevent or treat skin damage caused by ultraviolet irradiation, and can play a role in sun protection, repair and aging resistance.
The present invention is not limited to the above-described preferred embodiments, but rather, the present invention is to be construed broadly and cover all modifications, equivalents, and improvements falling within the spirit and scope of the present invention.
Claims (18)
1. The effective part of the flavones of the flower of abelmoschus manihot is characterized by comprising the following flavones: quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperin, wherein the mass ratio of the components is 1:13-33:1-7:14-38:12-32:1-5:18-42,
the preparation method of the effective part of the sunset abelmoschus flower flavonoid comprises the following steps: (1) extracting flos Abelmoschi Manihot with 60-95% ethanol solution to obtain extractive solution; (2) filtering the extractive solution with ultrafiltration membrane with molecular weight cutoff of 3500, and concentrating with ultrafiltration membrane with molecular weight of 500 to obtain concentrated solution; (3) removing ethanol from the concentrated solution, and eluting with macroporous resin to obtain flos Abelmoschi Manihot flavonoid effective fraction, wherein the macroporous resin is D101, HPD100 or AB-8, and the macroporous resin elution process comprises: the diameter-height ratio of the macroporous resin is 1:4-1:9, the concentration of a sample loading solution is 0.10-0.30g crude drug/ml, the volume of the sample loading solution is 4-12BV, sample loading is carried out at the flow rate of 1-4BV/h, impurity removal is carried out by using 4-8BV pure water and 1-5BV5% ethanol at the flow rate of 0.5-4BV/h, and elution is carried out by using 2-8BV 60% ethanol at the flow rate of 1-5 BV/h.
2. The effective fraction of sunset abelmoschus flowers according to claim 1, wherein the volume of the extract solution filtered out in the step (2) is 70-80% of the volume of the extract solution.
3. The effective part according to claim 1 or 2, characterized by comprising the following flavonoid ingredients: quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperin, wherein the mass ratio of the components is 1:15-32:2-6:16-36:14-30:2-4: 20-40.
4. The effective part according to claim 3, characterized by comprising the following flavonoid ingredients: quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperin, wherein the mass ratio of the components is 1:17-29:2.4-5.2:18-33:16-27:2.4-3.6: 23-38.
5. The effective part according to claim 4, which is characterized by comprising the following flavonoid ingredients: quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O-beta-D-glucuronide, isoquercitrin, rutin and hyperin, wherein the mass ratio of the components is 1:19-26:2.7-4.4:20-29:18-24:2.7-3.3: 26-35.
6. The effective fraction according to claim 1 or 2, wherein the content of quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O- β -D-glucuronide, isoquercitrin, rutin and hyperoside is 52% or more.
7. The active fraction according to claim 6, wherein the content of quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O- β -D-glucuronide, isoquercitrin, rutin and hyperoside is 56% or more.
8. The active site according to claim 7, wherein the content of quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O- β -D-glucuronide, isoquercitrin, rutin and hyperoside is 63-77%.
9. The active site according to claim 8, wherein the content of quercetin, quercetin-3' -O-glucoside, myricetin, gossypetin-8-O- β -D-glucuronide, isoquercitrin, rutin and hyperoside is 67-75%.
10. A pharmaceutical composition comprising the effective site of any one of claims 1 to 9, wherein the pharmaceutical composition further comprises a pharmaceutically acceptable carrier.
11. The pharmaceutical composition according to claim 10, wherein the pharmaceutical composition is in the form of a solution, ointment, gel, suspension.
12. Use of the effective part according to any one of claims 1 to 9, the pharmaceutical composition according to claim 10 or 11 for the preparation of a sunscreen agent, a post-sun repairing agent or an anti-aging cosmetic for preventing or treating skin aging.
13. Use of the effective fraction of any one of claims 1 to 9, the pharmaceutical composition of claim 10 or 11 for the preparation of an anti-aging medicament.
14. The method for preparing the effective fraction of any one of claims 1 to 9, comprising the steps of: (1) extracting flos Abelmoschi Manihot with 60-95% ethanol solution to obtain extractive solution; (2) filtering the extractive solution with ultrafiltration membrane with molecular weight cutoff of 3500, and concentrating with ultrafiltration membrane with molecular weight of 500 to obtain concentrated solution; (3) removing ethanol from the concentrated solution, eluting with macroporous resin to obtain effective components of flos Abelmoschi Manihot flower flavonoids,
wherein, the dosage of the ethanol in the step (1) is 10 to 25 times of that of the sunset abelmoschus flower, and the ethanol is 60 to 95 percent ethanol solution; in the step (2), the molecular weight is 500 and 3500, and the filtering volume of the filtration is 50-90% of the extracting solution; the model of the macroporous resin in the step (3) is D101, HPD100 or AB-8, and the elution process of the macroporous resin comprises the following steps: the diameter-height ratio of the macroporous resin is 1:4-1:9, the concentration of a sample loading solution is 0.10-0.30g crude drug/ml, the volume of the sample loading solution is 4-12BV, sample loading is carried out at the flow rate of 1-4BV/h, impurity removal is carried out by using 4-8BV pure water and 1-5BV5% ethanol at the flow rate of 0.5-4BV/h, and elution is carried out by using 2-8BV 60% ethanol at the flow rate of 1-5 BV/h.
15. The method according to claim 14, wherein the filtered volume of the filtration in the step (2) is 70 to 80% of the extract.
16. An effective part of flavones of abelmoschus manihot is prepared by the following preparation method: extracting the flower of abelmoschus manihot in 60-95% alcohol solution to obtain extracting solution; filtering the extracting solution obtained in the step (2) by using an ultrafiltration membrane with the molecular weight cutoff of 3500, and concentrating by using an ultrafiltration membrane with the molecular weight of 500 to prepare concentrated solution; removing ethanol from the concentrated solution in the step (3), and eluting by macroporous resin to obtain the effective part of the sunset abelmoschus flower flavonoids, wherein the type of the macroporous resin is D101, HPD100 or AB-8, and the elution process of the macroporous resin comprises the following steps: removing impurities with 4-8BV pure water and 1-5BV5% ethanol at flow rate of 0.5-4BV/h, and eluting with 2-8BV 60% ethanol at flow rate of 1-5 BV/h.
17. The effective fraction of claim 16, wherein the amount of ethanol used in step (1) is 10-25 times that of the flower of abelmoschus manihot; the filtering volume of the filtration in the step (2) is 50-90% of the extracting solution; the elution process of the macroporous resin in the step (3) comprises the following steps: the diameter-height ratio of the macroporous resin is 1:4-1:9, the concentration of a sample loading solution is 0.10-0.30g crude drug/ml, the volume of the sample loading solution is 4-12BV, the sample loading is carried out at the flow rate of 1-4BV/h, the impurities are removed by 4-8BV pure water and 1-5BV5% ethanol at the flow rate of 0.5-4BV/h, and the elution is carried out by 2-8BV 60% ethanol at the flow rate of 1-5 BV/h.
18. The active fraction of claim 17, wherein the volume of the extract solution filtered by the filtration in the step (2) is 70 to 80% of the volume of the extract solution.
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| WO2023174205A1 (en) * | 2022-03-15 | 2023-09-21 | 苏中药业集团股份有限公司 | Pharmaceutical formulation and use thereof |
| WO2023173268A1 (en) * | 2022-03-15 | 2023-09-21 | 苏中药业集团股份有限公司 | Effective parts of flavonoids from flos abelmoschus manihot, and preparation method therefor and use thereof |
| CN114642621B (en) * | 2022-05-06 | 2024-06-07 | 广州合颜和美生物工程有限公司 | Abelmoschus manihot flower mask, preparation method and application thereof |
| WO2025055910A1 (en) * | 2023-09-16 | 2025-03-20 | 苏中药业集团股份有限公司 | Use of pharmaceutical composition in preparation of drug for osteoporosis |
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