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CN-122011061-A - Arbutin derivative 6-O-Caffeoylarbutin and preparation method and application thereof

CN122011061ACN 122011061 ACN122011061 ACN 122011061ACN-122011061-A

Abstract

The invention discloses an arbutin derivative 6-O-Caffeoylarbutin, a preparation method and application thereof, wherein the structural formula of the 6-O-Caffeoylarbutin compound is shown as the formula (I): (I) The invention relates to an application of an arbutin derivative (6-O-Caffeoylarbutin) in preparing an antioxidant preparation. The first extracted 6-O-Caffeoylarbutin shows excellent antioxidant activity, has stronger ability for eliminating ABTB free radical than ascorbic acid and beta-arbutin, and provides a material basis for developing novel antioxidants.

Inventors

  • LIU SIYUAN
  • Pi Chengyan
  • LIU YUN
  • TANG JIANDONG
  • CAI GUOXIAN
  • LI RUONAN
  • LI JINGJING
  • ZHAO PING

Assignees

  • 西南林业大学

Dates

Publication Date
20260512
Application Date
20260106
Priority Date
20250106

Claims (9)

  1. 1. The arbutin derivative 6-O-Caffeoylarbutin is characterized in that the structural formula of the arbutin derivative 6-O-Caffeoylarbutin is shown as the formula (I): (I) 。
  2. 2. The method for preparing arbutin derivative 6-O-Caffeoylarbutin as claimed in claim 1, which is characterized by comprising the following steps: a. Taking a dry sample of Yunnan golden camellia leaves, and crushing the dry sample to 40-80 meshes; b. Extracting with 95% industrial methanol under reflux at 40-60deg.C for 3 times, each time for 1-3 hr; c. mixing the extractive solutions, and recovering methanol at 40-60deg.C by rotary evaporator to obtain methanol extract; d. Mixing the methanol extract with distilled water, and extracting with petroleum ether and ethyl acetate in sequence; e. Recovering solvent to obtain petroleum ether extract and ethyl acetate extract, and concentrating the rest water phase at high temperature and low pressure to obtain Yunnan golden camellia water phase extract; f. mixing with macroporous resin D101, loading on column, and gradient eluting with water/methanol to obtain 40% methanol water extract; g. Eluting with Sephadex LH-20 gel column to obtain 10 components Fr., component A to component J; h. Purifying by silica gel column chromatography and high performance liquid chromatography PHPLC to obtain compound 6-O-Caffeoylarbutin.
  3. 3. The method for preparing arbutin derivative 6-O-Caffeoylarbutin according to claim 2, wherein in the step (C), the methanol used is industrial grade methanol, in the step (d), the petroleum ether and the ethyl acetate used are both industrial grade, and the temperature of the petroleum ether is 60-90 ℃.
  4. 4. The preparation method of arbutin derivative 6-O-Caffeoylarbutin according to claim 1, wherein in the step (f), water and methanol are subjected to gradient elution, the volume ratio of water to methanol is 100:0-0:100, in the step (g), the preparation method is realized by gradient elution in gel column chromatography, the volume ratio of water to methanol is 80:20-0:100, and in the step (h), silica gel is used in an amount of 200-300 meshes.
  5. 5. An aqueous extract of Yunnan golden camellia, characterized in that the extract is obtained by the method of any one of claims 2 to 4.
  6. 6. Use of arbutin derivatives 6-O-Caffeoylarbutin as claimed in claim 1 for the preparation of antioxidant preparations.
  7. 7. A composition comprising 6-O-Caffeoylarbutin as defined in claim 1, wherein the composition is used for antioxidation.
  8. 8. A method for determining the antioxidant activity of 6-O-Caffeoylarbutin as defined in claim 1, wherein the ABTS + radical clearance is used as a test index.
  9. 9. The method according to claim 8, wherein the formula of the radical clearance of ABTS + is ABTS clearance (%) = [ blank- (sample-control) ]/blank X100%.

Description

Arbutin derivative 6-O-Caffeoylarbutin and preparation method and application thereof Technical Field The invention relates to the technical field of natural product chemistry and phytochemistry, in particular to an arbutin derivative (6-O-Caffeoylarbutin) and a preparation method and application thereof. Background Yunnan golden Camellia (Camellia fascicularis) is a deciduous small shrub belonging to the genus Camellia (Camellia) of the family Theaceae (Theaceae), known as its golden petals. Golden camellia is a rare species, has a history of medicine and food for hundreds of years in China, and is used for treating various diseases such as diarrhea, hematochezia, tumor, hypertension and the like. The Yunnan golden camellia contains rich amino acids, minerals, tea polyphenols, saponins, flavonoids, tea polysaccharides and other bioactive components, and pharmacological and clinical experiments prove that the Yunnan golden camellia has various pharmacological effects of resisting oxidation, resisting tumors, resisting bacteria, reducing blood fat, reducing blood sugar, reducing cholesterol and the like. Although Yunnan golden camellia has so many potential health benefits, the research of the Yunnan golden camellia (Camellia fascicularis) with a very small group special to Yunnan is started later, and the mining potential of functional active ingredients is huge. Particularly in the water phase, the Yunnan golden camellia shows better antioxidant activity than other organic phases, but specific components are not clear. At present, a 6-O-Caffeoylarbutin compound with antioxidant activity, a preparation method and application thereof are lacking. Disclosure of Invention The invention aims to provide a 6-O-Caffeoylarbutin compound with antioxidant activity, and a preparation method and application thereof. In order to solve the technical problems, the invention adopts the technical proposal that In a first aspect, the present application provides a 6-O-Caffeoylarbutin compound. In a second aspect, the present application provides a process for the preparation of a 6-O-Caffeoylarbutin compound. In a third aspect, the application provides a Yunnan golden camellia aqueous phase extract. In a fourth aspect, the application provides the use of a 6-O-Caffeoylarbutin) compound in the preparation of an antioxidant formulation. In a fifth aspect, the present application provides a composition comprising 6-O-Caffeoylarbutin for use in antioxidation. In a sixth aspect, the application provides a method for determining the antioxidant activity of 6-O-Caffeoylarbutin using the ABTS + radical clearance as a test indicator. The structural formula of the 6-O-Caffeoylarbutin compound and the 6-O-Caffeoylarbutin compound provided by the first aspect of the application is shown as the formula (I):(I) 。 The preparation method of the 6-O-Caffeoylarbutin compound provided by the second aspect of the application comprises the following steps: a. Taking a dry sample of Yunnan golden camellia leaves, and crushing the dry sample to 40-80 meshes; b. Extracting with 95% industrial methanol under reflux at 40-60deg.C for 3 times, each time for 1-3 hr; c. Mixing the extractive solutions, and recovering methanol at 40-60deg.C by rotary evaporator to obtain methanol extract; d. Mixing the methanol extract with distilled water, and extracting with petroleum ether and ethyl acetate in sequence; e. Recovering solvent to obtain petroleum ether extract and ethyl acetate extract, and concentrating the rest water phase at high temperature and low pressure to obtain Yunnan golden camellia water phase extract; f. mixing with macroporous resin D101, loading on column, and gradient eluting with water/methanol to obtain 40% methanol water extract; g. eluting with Sephadex LH-20 gel column to obtain 10 components Fr. (A-J); h. Purifying by silica gel column chromatography and high performance liquid chromatography (PHPLC) to obtain 6-O-Caffeoylarbutin as monomer compound. Further, in the step (C), the methanol used is technical grade methanol, and in the step (d), the petroleum ether and the ethyl acetate used are both technical grade, and the temperature of the petroleum ether is 60-90 ℃. Further, in the step (f), gradient elution is carried out by water and methanol, the volume ratio of water to methanol is 100:0-0:100, in the step (g), gradient elution is carried out by gel column chromatography, the volume ratio of water to methanol is 80:20-0:100, and in the step (h), the silica gel used is 200-300 meshes. The third aspect of the application provides a Yunnan golden camellia aqueous phase extract, which is obtained by the method. In a fourth aspect, the application provides the use of a 6-O-Caffeoylarbutin compound in the preparation of an antioxidant formulation. In a fifth aspect the application provides a composition comprising 6-O-Caffeoylarbutin) for use in antioxidation. In a sixth aspect, the application provides a method for determining the