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CN-120965789-B - Active naphthalene glycoside component in dianella root, extraction method and application thereof

CN120965789BCN 120965789 BCN120965789 BCN 120965789BCN-120965789-B

Abstract

Active naphthalene glycoside component in dianella root, extraction method and application thereof are provided. The invention belongs to the technical fields of plant separation and extraction, medicine and daily chemicals, and particularly relates to an active naphthalene glycoside component in dianella root, an extraction method and application thereof. The invention aims to solve the problem that the compound with whitening effect in dianella root is not clear. The extraction method comprises drying and pulverizing dianella root, extracting with ethanol under reflux, concentrating to obtain concentrated solution, separating the concentrated solution by macroporous resin adsorption chromatography, ODS column chromatography, and preparative liquid chromatography to obtain naphthalin components, wherein the naphthalin components are 5-hydroxydianellose and 5-hydroxydianellin, dianellose, dianellin, and the naphthalin components are used as active components for preparing whitening and freckle removing cosmetics and pharmaceutical preparations. The extraction and separation method provided by the invention is simple, convenient and rapid, and the extracted compound has high purity, can effectively remove DPPH free radical and inhibit tyrosinase activity, and has good application prospect in whitening and freckle removing aspects.

Inventors

  • MA TIANCHENG
  • SUN YU
  • HONG YU
  • MA YUKUN
  • LIU HUANHUAN
  • Wan Qingjin

Assignees

  • 齐齐哈尔医学院

Dates

Publication Date
20260508
Application Date
20250805

Claims (8)

  1. 1. The extraction method of the active naphthalene glycoside component in the dianella root is characterized by comprising the following steps of: 1. Drying and pulverizing dianella root, extracting with 70% ethanol under reflux to obtain concentrated solution, concentrating and drying to obtain crude dianella root extract; 2. Dissolving the raw dianella root extract with water to obtain a dianella root solution, loading the dianella root solution on a D101 macroporous resin adsorption column, and eluting with water, a 15% ethanol aqueous solution, a 30% ethanol aqueous solution, a 60% ethanol aqueous solution and a 90% ethanol aqueous solution in sequence to obtain ethanol aqueous solution eluents with different concentrations; 3. concentrating the 60% ethanol water elution fraction obtained in the second step, evaporating to dryness, separating by using ODS column chromatography, and eluting by sequentially using a methanol water solution with the volume concentration of 20%, a methanol water solution with the volume concentration of 40%, a methanol water solution with the volume concentration of 60%, a methanol water solution with the volume concentration of 70% and a methanol water solution with the volume concentration of 90% at the flow rate of 10-20 mL/min to obtain methanol water elution fractions with different concentrations; 4. Concentrating 40% methanol water elution fraction and 60% ethanol water elution fraction respectively, evaporating to dryness, separating by liquid chromatography, separating from 40% methanol water elution fraction to obtain a compound 1, 5-dihydroxy-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-xylosyl- (1- > 6) ] -beta-D-glucoside with retention time of 15.5 min and a compound 2, 5-dihydroxy-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-rhamnosyl- (1- > 6) ] -beta-D-glucoside with retention time of 16.5 min, separating from 60% methanol water elution fraction to obtain a compound 3 1-hydroxy-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-xylosyl- (1- > 6) ] -beta-D-glucoside with retention time of 22.5 min and a compound 4 1-hydroxy-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L- [ alpha-1- > 6) ] -beta-D-glucoside with retention time of 23.5 min; The molecular formula of the compound 1, 5-dihydroxyl-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-xylosyl- (1- & gt 6) ] -beta-D-glucoside is C 24 H 30 O 13 , the molecular weight 526 and the structural formula are as follows: ; The molecular formula of the compound 2, 5-dihydroxyl-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-rhamnosyl- (1- & gt 6) ] -beta-D-glucoside is C 25 H 32 O 13 , the molecular weight is 540, and the structural formula of ESI-MS (negative) is M/z 539.3 [ M-H ] - , wherein the structural formula is as follows: ; The molecular formula of the compound 3 1-hydroxy-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-xylosyl- (1- & gt 6) ] -beta-D-glucoside is C 24 H 30 O 12 , the molecular weight is 510, and the ESI-MS (negative) is M/z 508.8 [ M-H ] - , and the structural formula is as follows: ; The molecular formula of the compound 4 1-hydroxy-2-acetyl-3-methylnaphthalene-8-O- [ alpha-L-rhamnosyl- (1- & gt 6) ] -beta-D-glucoside is C 25 H 32 O 12 , the molecular weight is 524, and the ESI-MS (negative) is M/z 523.0 [ M-H ] - , and the structural formula is as follows: 。
  2. 2. The method for extracting active naphthalene glycosides from dianella root according to claim 1, wherein the 70% ethanol reflux method comprises steps of drying and pulverizing dianella root, adding ethanol with volume 5-10 times and 70-95% of the dianella root, reflux extracting for 2-3 h, filtering to remove residues while hot, extracting for 3 times, mixing filtrates, and concentrating under reduced pressure at 45-55 ℃ to obtain concentrated solution.
  3. 3. The method for extracting active naphthalene glycosides from dianella root as set forth in claim 1, wherein in step four, the liquid chromatograph is a Waters 2545 high-phase liquid chromatograph, the detector is a Waters 2489 type ultraviolet detector, the packing of the chromatographic column is C18 reversed phase silica gel, the mobile phase is a mixture of acetonitrile and water in a volume ratio of 22:78 and a methanol aqueous solution in a water ratio of methanol to water of 40:60, the flow rate is 10 ml/min, and the detection wavelength is 224 nm.
  4. 4. The application of active naphthalene glycoside components in dianella root is characterized in that the active naphthalene glycoside components in dianella root are compounds 1-4 extracted by the extraction method of claim 1, and the compounds are used as active components for preparing whitening and freckle removing cosmetics.
  5. 5. The use of an active naphthalene glycoside component in dianella root according to claim 4, wherein the cosmetic for whitening and removing freckle further comprises one or more of a humectant, an antioxidant, a surfactant and a thickener.
  6. 6. The use of an active naphthalene glycoside in dianella root according to claim 4, wherein the cosmetic for whitening and removing freckle is in the form of aqueous solution, emulsion, cream, ointment, gel or facial mask.
  7. 7. The application of active naphthalene glycoside components in dianella root is characterized in that the active naphthalene glycoside components in dianella root are compounds 1-4 extracted by the extraction method of claim 1, and the compounds are used as active components for preparing pharmaceutical preparations.
  8. 8. The use of active naphthalene glycosides in dianella root as set forth in claim 7, wherein the pharmaceutical preparation further comprises one or more of stearic acid, cetyl alcohol and castor oil, triethanolamine and propylene glycol.

Description

Active naphthalene glycoside component in dianella root, extraction method and application thereof Technical Field The invention belongs to the technical fields of plant separation and extraction, medicine and daily chemicals, and particularly relates to an active naphthalene glycoside component in dianella root, an extraction method and application thereof. Background The dianella root is the dry root of dianella [ Dianella ensifolia (L.) DC ] of dianella of the genus dianella of the family Liliaceae, and is a common medicine of Lahu, and is also called dianella, shanjiao, cat, etc. It is mainly produced in regions of Yunnan, guangdong, guizhou, sichuan, guangxi and Fujian etc. in China and also distributed in tropical regions of sub-state. It is sweet and pungent in flavor, cool in nature, and has the actions of removing toxic substances and relieving swelling and pain. The Chinese medicinal composition is ground into powder and mixed with proper amount of vinegar, and then the mixture is applied to affected parts to treat carbuncle, abscess, tinea, lymphadenitis and other diseases. At present, chemical components of dianella are not deeply researched, the structural types are mainly flavans, chromones, naphthalin, resorcinol and the like, and the dianella has biological activity effects of whitening, resisting tumors, resisting oxidation and the like, but the whitening efficacy components are not clear. In recent years, safety accidents frequently occur in chemical synthetic cosmetics, so that consumers are promoted to pay more attention to purely natural plant cosmetics during purchasing. The Chinese herbal medicine obtains the acceptance and favor of wide consumers by virtue of mild medicine effect and lower adverse reaction risk. However, chinese herbal medicine resources in China are very rich, different kinds of medicinal materials have different properties, and each medicinal material contains various chemical components. The characteristics bring great challenges to the research and development of natural Chinese herbal medicine whitening cosmetics with high efficiency and safety, and the research and development of the natural Chinese herbal medicine whitening cosmetics are difficult in terms of accurate extraction of active ingredients and guarantee of product safety and efficacy. The beauty is pursued naturally by people, especially women, but the skin-whitening and skin-care products on the market at present mainly adopt chemical light-shading agents, decoloration or corner layer stripping, have unobvious effects and easy recurrence, have certain side effects, and always afflict people loving beauty. The skin color of the human body is mainly dependent on the content and distribution of melanin, and the inhibition of melanin generation can achieve the effect of skin whitening, and common experimental methods include tyrosinase activity inhibition experiments and DPPH free radical oxidation resistance experiments. It is not clear from the present literature that the compounds having whitening effect in dianella root are synthesized. The invention discovers a naphthalin compound with whitening effect in dianella root. Disclosure of Invention The invention aims to solve the technical problem that a compound with whitening effect in dianella root is not clear, and provides an active naphthalene glycoside component in dianella root, an extraction method and application thereof. The molecular formula of the active naphthalene glycoside component in the dianella root is C 24H30O13, the molecular weight is 526, and the molecular weight of ESI-MS (negative) is M/z 525.2 [ M-H ] -, and the structural formula is as follows: 。 the molecular formula of the active naphthalene glycoside component in the dianella root is C 24H30O12, the molecular weight is 510, and the molecular weight of ESI-MS (negative) is M/z 508.8 [ M-H ] -, and the structural formula is as follows: 。 The extraction method of the active naphthalene glycoside component in the dianella root comprises the following steps: 1. Drying and pulverizing dianella root, extracting with 70% ethanol under reflux to obtain concentrated solution, concentrating and drying to obtain crude dianella root extract; 2. Dissolving the raw dianella root extract with water to obtain a dianella root solution, loading the dianella root solution on a D101 macroporous resin adsorption column, and eluting with water, a 15% ethanol aqueous solution, a 30% ethanol aqueous solution, a 60% ethanol aqueous solution and a 90% ethanol aqueous solution in sequence to obtain ethanol aqueous solution eluents with different concentrations; 3. concentrating the 60% ethanol water elution fraction obtained in the second step, evaporating to dryness, separating by using ODS column chromatography, and eluting by sequentially using a methanol water solution with the volume concentration of 20%, a methanol water solution with the volume concentration of 40%, a methanol water solution