LU501312B1 - Chemical synthesis method of prodelphinidin b9 gallate - Google Patents
Chemical synthesis method of prodelphinidin b9 gallate Download PDFInfo
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
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Abstract
The present disclosure aims to provide a chemical synthesis method of a prodelphinidin B9 gallate. A waxberry leaf proanthocyanidin is used as a raw material, an epigallocatechin gallate (EGCG) is used as a nucleophilic reagent, and C4 sites of structural units EGCG and epigallocatechin (EGC) of the waxberry leaf proanthocyanidin are attacked under catalysis of hydrochloric acid to synthesize the prodelphinidin B9 gallate. Compared with prodelphinidin B9 gallates extracted and separated from tea leaves, waxberry leaves and other materials, the prodelphinidin B9 gallate prepared by using the method provided in the present disclosure has higher purity and yield and can be directly used as a nutrient enhancer and a natural antioxidant in the field of food.
Description
CHEMICAL SYNTHESIS METHOD OF PRODELPHINIDIN B9 GALLATE HUS0T312
[01] The present disclosure relates to the field of plant functional components, and in particular to a preparation method of a prodelphinidin B9 gallate.
[02] As a type of polymeric polyphenols with flavan-3-ols as structural units, proanthocyanidins are widely found in plants and are the second largest type of dietary polyphenols after lignin. Main structural units of the proanthocyanidins include (epi)catechin, (epi)afzelechin, (epi)gallocatechin ((E)GC) and gallates thereof.
[03] Through a large number of researches, it is shown that the proanthocyanidins have various kinds of beneficial biological activity such as oxidation resistance, blood sugar reduction and weight loss. However, these functions are closely related to structures, especially types and polymerization degrees of the structural units. First, bioavailability of the proanthocyanidins is determined by the polymerization degrees of the proanthocyanidins. When the polymerization degree is increased, the bioavailability is reduced. The proanthocyanidins with a polymerization degree greater than 4 are basically not absorbed. A density of a phenolic hydroxyl group in a structural unit of the proanthocyanidins is closely related to the biological activity. Researches have shown that compared with the proanthocyanidins without galloyl groups, the proanthocyanidins containing the galloyl groups in the structural units have stronger biological activity due to a higher density of the phenolic hydroxyl group. Prodelphinidins with the (E)GC and (epi)gallocatechin gallate ((E)GCG) thereof as the structural units are the proanthocyanidins with strong activity.
[04] At present, the proanthocyanidins with more researches include the (epi)catechin, the (epi)afzelechin and the gallates thereof as the structural units. Due to abundant sources, researches on structure-function relationships with dimers as materials are relatively clear; and researches on the prodelphinidins are conducted based on mixtures of the proanthocyanidins. The proanthocyanidins derived from waxberry leaves have typical prodelphinidin structures, include the EGC and the EGCG as the main structural units, and have extremely strong in-vitro antioxidant activity. However, since the polymerization degree is high and is in a range of 9.5 to
26.7, the bioavailability is extremely low, the in-vivo activity is low, and action mechanisms are unclear. The prodelphinidins with a low polymerization degree are extremely low in content and difficult to separate and purify, so that researches on the structure-function relationships of the prodelphinidins are limited.
1
[05] An objective of the present disclosure is to provide a chemical synthesis method of a prodelphinidin B9 gallate. In the present disclosure, a waxberry leaf proanthocyanidin is used as a raw material, an EGCG is used as a nucleophilic substrate, and two dimeric prodelphinidin gallates including a prodelphinidin B-3'-gallate and a prodelphinidin B-3,3'-digallate are synthesized under catalysis of an acid. A component content is increased, and purification difficulty is further reduced. The obtained dimeric prodelphinidin gallate is a B-type proanthocyanidin dimer with the EGCG as a structural unit. Not only is the bioavailability of the prodelphinidin-type proanthocyanidin improved, but also a high-purity material is provided for a research on a structure-function relationship of the prodelphinidin-type proanthocyanidin.
[06] The present disclosure adopts the following technical solution.
[07] A chemical synthesis method of a prodelphinidin B9 gallate specifically includes:
[08] separately preparing a hydrochloric acid-containing solution of the waxberry leaf proanthocyanidin with a concentration of 10-400 mg/mL and a hydrochloric acid-containing solution of the EGCG with a concentration of 10-400 mg/mL, where the two hydrochloric acid-containing solutions both include a hydrochloric acid concentration of 0.1-1.0 mol/L; and mixing the hydrochloric acid-containing solutions of the waxberry leaf proanthocyanidin and the EGCG with the same hydrochloric acid concentration at a volume ratio of 1:2 to 2:1 for a reaction at 20-60°C for 40 minutes, and then conducting drying and separation purification to obtain the prodelphinidin B9 gallate, where the prodelphinidin B9 gallate includes the prodelphinidin B-3'-gallate and the prodelphinidin B-3,3'-digallate.
[09] A structural formula of the prodelphinidin B9 gallate including the prodelphinidin B-3'-gallate and the prodelphinidin B-3,3'-digallate is as follows. a SIC COX, I | A er
[10] Prodelphinidin B-3’-gallate Prodelphinidin B-3,3'-digallate 2
[11] With reference to a patent “METHOD FOR PREPARAING WAXBERRY LEAF POTSTE PROANTHOCYANIDIN BY SEPARATION”, a method for extracting and purifying the waxberry leaf proanthocyanidin is used. The prepared waxberry leaf proanthocyanidin has a purity of 864%. The EGCG is a commercially available high performance liquid chromatography (HPLC) grade reagent with a purity greater than or equal to 98%.
[12] As a preferred solution, a drying method specifically includes: conducting rotary evaporation on a reaction solution obtained 40 minutes after the reaction at 40°C to remove methanol and a small amount of water, so as to obtain a dry powder of a crude reaction product.
[13] As a preferred solution, the separation purification is conducted on the obtained crude reaction product by Shimadzu LC-20 semi-preparative liquid chromatography to obtain the prodelphinidin B9 gallate.
[14] The purification includes using an S series XSH preparation column (10 mm * 250 mm, um), acetonitrile containing 0.5 vol% acetic acid as a mobile phase A and ultrapure water as a mobile phase B; dissolving the crude reaction product in a mixture of the mobile phase A and the mobile phase B at a volume ratio of 88:12 to prepare a 20 mg/mL solution; introducing 2 mL of a sample, and conducting elution purification with the mobile phases at a flow rate of 5 mL/min and an elution gradient of 12-27 vol% B for 0-10 minutes, 60 vol% B for 10-20 minutes and 12 vol% B for 20-26 minutes; and setting a detection wavelength to be 280 nm, collecting an effluent at 5.5-6.0 minutes according to a liquid phase spectrum, conducting rotary evaporation on the effluent at 40°C to remove the acetonitrile, and then conducting freeze-drying to obtain a purified prodelphinidin B9 gallate.
[15] Further, the separation purification also includes secondary purification.
[16] The secondary purification includes using Shim-pack GIST C18 (20 mm * 250 mm, 5 um), ultrapure water as a mobile phase A and 98 vol% acetonitrile (containing 0.05 vol% phosphoric acid) as a mobile phase B; dissolving the purified prodelphinidin B9 gallate in a mixture of the mobile phase A and the mobile phase B at a volume ratio of 80:20 to prepare a 50 mg/mL solution; introducing 2 mL of a sample, and conducting elution purification with the mobile phases at a flow rate of 15 mL/min and an elution gradient of 20-40 vol% B for 0-5 minutes and 40 vol% B for 5-15 minutes; and setting a detection wavelength to be 280 nm, collecting an effluent at different peak times according to a liquid phase spectrum, conducting rotary evaporation on the effluent at 40°C to remove the acetonitrile, and then conducting freeze-drying to obtain the prodelphinidin B-3'-gallate and the prodelphinidin B-3,3'-digallate.
[17] In the present disclosure, the waxberry leaf proanthocyanidin is used as a raw material, the EGCG is used as a nucleophilic reagent, and C4 sites of the structural units EGCG and EGC of the waxberry leaf proanthocyanidin are attacked under catalysis of hydrochloric acid to 3 synthesize the prodelphinidin B9 gallate. Compared with prodelphinidin B9 gallates extracted POTSTE and separated from tea leaves, waxberry leaves and other materials, the prodelphinidin B9 gallate prepared by using the method provided in the present disclosure has higher purity and yield. The prodelphinidin B9 gallate can be directly used as a nutrient enhancer and a natural antioxidant in the field of food.
[18] FIG. 1 is an HPLC analysis spectrum of synthesis of a prodelphinidin B9 gallate in Example 1;
[19] FIG. 2 is an HPLC analysis spectrum of synthesis of a prodelphinidin B9 gallate in Example 2;
[20] FIG. 3 is an HPLC analysis spectrum of synthesis of a prodelphinidin B9 gallate in Example 3;
[21] FIG. 4 is an HPLC analysis spectrum of synthesis of a prodelphinidin B9 gallate in Example 4;
[22] FIG. 5 is an HPLC analysis spectrum of synthesis of a prodelphinidin B9 gallate in Example 5;
[23] FIG. 6 is an HPLC analysis spectrum of synthesis of a prodelphinidin B9 gallate in Example 6;
[24] FIG. 7 is an HPLC analysis spectrum of a prodelphinidin B-3'-gallate with a purity of
93.2% prepared in Example 1;
[25] FIG. 8 is an HPLC analysis spectrum of a prodelphinidin B-3,3'-digallate with a purity of
96.6% prepared in Example 1;
[26] FIG. 9 is a mass spectrum of the prodelphinidin B-3'-gallate with a molecular weight of 762 prepared in Example 1;
[27] FIG. 10 is a mass spectrum of the prodelphinidin B-3,3'-digallate with a molecular weight of 914 prepared in Example 1;
[28] FIG. 11 is a 13 carbon nuclear magnetic resonance (13 C NMR) spectrum of the prodelphinidin B-3'-gallate prepared in Example 1; and
[29] FIG. 12 is a 13 C NMR spectrum of the prodelphinidin B-3,3'-digallate prepared in Example 1.
[30] In FIG. 1 to FIG. 6, peak times of the prodelphinidin B-3'-gallate (1) and the prodelphinidin B-3,3'-digallate (2) are 9.9 minutes and 11.7 minutes respectively.
DETAILED DESCRIPTION OF THE EMBODIMENTS 4
[31] In order to make the objectives and technical solutions of the present disclosure clearer. POTSTE specific embodiments of the present disclosure are further described in detail below, but are not used to limit the present disclosure. Reaction conditions in various examples are different. Drying and separation purification (purification is conducted twice) are specifically conducted as follows.
[32] Drying: Rotary evaporation is conducted on a reaction solution obtained 40 minutes after a reaction at 40°C to remove methanol and a small amount of water, so as to obtain a dry powder of a crude reaction product.
[33] Separation purification:
[34] During primary purification, an S series XSH preparation column (10 mm * 250 mm, 5 um) is used, acetonitrile containing 0.5 vol% acetic acid is used as a mobile phase A, and ultrapure water is used as a mobile phase B; the crude reaction product in dissolved a mixture of the mobile phase A and the mobile phase B at a volume ratio of 88:12 to prepare a 20 mg/mL solution; 2 mL of a sample is introduced, and elution purification is conducted with the mobile phases at a flow rate of 5 mL/min and an elution gradient of 12-27 vol% B for 0-10 minutes, 60 vol% B for 10-20 minutes and 12 vol% B for 20-26 minutes; and a detection wavelength is set to be 280 nm, an effluent is collected at 5.5-6.0 minutes according to a liquid phase spectrum, rotary evaporation is conducted on the effluent at 40°C to remove the acetonitrile, and then freeze-drying is conducted to obtain a purified prodelphinidin B9 gallate.
[35] During secondary purification, Shim-pack GIST C18 (20 mm * 250 mm, 5 um) is used, ultrapure water is used as a mobile phase A, and 98 vol% acetonitrile (containing 0.05 vol% phosphoric acid) is used as a mobile phase B; the purified prodelphinidin B9 gallate is dissolved in a mixture of the mobile phase A and the mobile phase B at a volume ratio of 80:20 to prepare a 50 mg/mL solution; 2 mL of a sample is introduced, and elution purification is conducted with the mobile phases at a flow rate of 15 mL/min and an elution gradient of 20-40 vol% B for 0-5 minutes and 40 vol% B for 5-15 minutes; and a detection wavelength is set to be 280 nm, an effluent is collected at different peak times according to a liquid phase spectrum, rotary evaporation is conducted on the effluent at 40°C to remove the acetonitrile, and then freeze-drying is conducted to obtain a prodelphinidin B-3'-gallate and a prodelphinidin B-3,3'-digallate.
[36] In addition, a synthesis detection method of the prepared prodelphinidin B9 gallate is as follows.
[37] The prodelphinidin B9 gallate is analyzed by HPLC. Specific analysis conditions include that Waters 2695 is used for HPLC, a Waters 2489 ultraviolet-visible light detector is used, a detection wavelength is 280 nm, and a Chromatographic column model is Luna hilic (4.6 mm *
250 mm, 5 um, Phenomemex Inc.); acetonitrile (containing 0.5 vol% acetic acid) is used ri mobile phase A, and ultrapure water is used as a mobile phase B; an elution gradient includes 12-27 vol% B for 0-30 minutes, 27-80 vol% B for 30-45 minutes, 80-12 vol% B for 45-46 minutes and 12 vol% B for 46-55 minutes; a flow rate is 0.8 mL/min; a sample introduction amount is 10 pL; and a column temperature is 30°C.
[38] A method for detecting the purity and structure of the prepared prodelphinidin B9 gallate is as follows.
[39] Liquid chromatography-mass spectrometry analysis: À rapid liquid chromatography-triple quadrupole mass spectrometer Agilent 1290/6460 Triple Quad is used for analysis, and chromatographic conditions are the same as the conditions above. Mass spectrometry conditions include that an ESI negative ion mode is used as an ionization mode; a mass-to-charge ratio scanning range is 50-1500 m/z; a desolvation temperature is 400°C; a capillary voltage is 3.5 kV; and a collision energy is 16 eV.
[40] 13 C NMR analysis: An Agilent DD2-600 NMR spectrometer with a superconducting magnet is used for analysis, and methanol-D4 is used as a solvent.
[41] Example 1:
[42] 1 g of a waxberry leaf proanthocyanidin and 1 g of an EGCG were separately weighed and dissolved in 50 mL of a 0.1 mol/L HCl methanol solution for uniform stirring until the solution was clear to obtain a waxberry leaf proanthocyanidin solution and an EGCG solution, 50 ml of the waxberry leaf proanthocyanidin solution and 50 mL of the EGCG solution were mixed in a conical flask with a cover and heated in a water bath at 40°C for 40 minutes, and then drying, separation purification and detection were conducted. As shown in FIG. 1, a prodelphinidin B-3'-gallate had a yield of 8.5%, and a prodelphinidin B-3,3'-digallate had a yield of 20.0%.
[43] FIG. 7 and FIG. 8 were HPLC analysis spectra of the prepared prodelphinidin B-3'-gallate and prodelphinidin B-3,3'-digallate respectively. The prodelphinidin B-3'-gallate had a purity of 93.2%, and the prodelphinidin B-3,3'-digallate had a purity of 96.6%.
[44] FIG. 9 and FIG. 10 were mass spectra of the prodelphinidin B-3'-gallate and prodelphinidin B-3,3'-digallate prepared in the present disclosure respectively. It could be seen that the prodelphinidin B-3'-gallate had a molecular weight of 762, and the prodelphinidin B-3,3'-digallate had a molecular weight of 914.
[45] FIG. 11 and FIG. 12 were 13 C NMR spectra of the prodelphinidin B-3'-gallate and prodelphinidin B-3,3'-digallate prepared in the present disclosure respectively. A carbonyl group (166 ppm) and galloyl ring carbon signals (138 ppm and 110 ppm) of gallic acid were characteristics of gallated flavan-3-ols, indicating that a structural unit contained the EGCG. In 6 addition, an A-type proanthocyanidin usually had a broad peak signal at 102-104 ppm, but the POTSTE signal was not detected, indicating that there was no A-type bond in the structure. The prodelphinidin B-3'-gallate and the prodelphinidin B-3,3'-digallate were obtained.
[46] Example 2:
[47] 1 g of a waxberry leaf proanthocyanidin and 1 g of an EGCG were separately weighed and dissolved in 100 mL of a 0.1 mol/L HCl methanol solution for uniform stirring until the solution was clear to obtain a waxberry leaf proanthocyanidin solution and an EGCG solution, 50 ml of the waxberry leaf proanthocyanidin solution and 25 mL of the EGCG solution were mixed in a conical flask with a cover and heated in a water bath at 40°C for 40 minutes, and then drying, separation purification and detection were conducted. As shown in FIG. 2, a prodelphinidin B-3'-gallate had a yield of 6.2%, and a prodelphinidin B-3,3'-digallate had a yield of 11.6%.
[48] Example 3:
[49] 1 g of a waxberry leaf proanthocyanidin and 1 g of an EGCG were separately weighed and dissolved in 50 mL of a 0.1 mol/L HCl methanol solution for uniform stirring until the solution was clear to obtain a waxberry leaf proanthocyanidin solution and an EGCG solution, 50 ml of the waxberry leaf proanthocyanidin solution and 50 mL of the EGCG solution were mixed in a conical flask with a cover and heated in a water bath at 60°C for 40 minutes, and then drying, separation purification and detection were conducted. As shown in FIG. 3, a prodelphinidin B-3'-gallate had a yield of 4.0%, and a prodelphinidin B-3,3'-digallate had a yield of 18.0%.
[50] Example 4: [S1] 1 g of a waxberry leaf proanthocyanidin and 1 g of an EGCG were separately weighed and dissolved in 5.0 mL of a 0.1 mol/L HCl methanol solution for uniform stirring until the solution was clear to obtain a waxberry leaf proanthocyanidin solution and an EGCG solution,
2.5 ml of the waxberry leaf proanthocyanidin solution and 5.0 mL of the EGCG solution were mixed in a conical flask with a cover and heated in a water bath at 20°C for 40 minutes, and then drying, separation purification and detection were conducted. As shown in FIG. 4, a prodelphinidin B-3'-gallate had a yield of 16.6%, and a prodelphinidin B-3,3'-digallate had a yield of 19.5%.
[52] Example 5: [S3] 2 g of a waxberry leaf proanthocyanidin and 2 g of an EGCG were separately weighed and dissolved in 5.0 mL of a 0.1 mol/L HCl methanol solution for uniform stirring until the solution was clear to obtain a waxberry leaf proanthocyanidin solution and an EGCG solution,
2.5 ml of the waxberry leaf proanthocyanidin solution and 5.0 mL of the EGCG solution were 7 mixed in a conical flask with a cover and heated in a water bath at 40°C for 40 minutes, and then 501312 drying, separation purification and detection were conducted. As shown in FIG. 5, a prodelphinidin B-3'-gallate had a yield of 27.9%, and a prodelphinidin B-3,3'-digallate had a yield of 21.2%. [S4] Example 6: [S5] 1 g of a waxberry leaf proanthocyanidin and 1 g of an EGCG were separately weighed and dissolved in 50.0 mL of a 1 mol/L HCl methanol solution for uniform stirring until the solution was clear to obtain a waxberry leaf proanthocyanidin solution and an EGCG solution, 50 ml of the waxberry leaf proanthocyanidin solution and 50 mL of the EGCG solution were mixed in a conical flask with a cover and heated in a water bath at 40°C for 40 minutes, and then drying, separation purification and detection were conducted. As shown in FIG. 4, a prodelphinidin B-3'-gallate had a yield of 6.8%, and a prodelphinidin B-3,3'-digallate had a yield of 18.0%.
8
Claims (5)
1. À chemical synthesis method of a prodelphinidin B9 gallate, specifically comprising: separately preparing a hydrochloric acid-containing solution of a waxberry leaf proanthocyanidin with a concentration of 10-400 mg/mL and a hydrochloric acid-containing solution of an epigallocatechin gallate (EGCG) with a concentration of 10-400 mg/mL, wherein the two hydrochloric acid-containing solutions both comprise a hydrochloric acid concentration of 0.1-1.0 mol/L; and mixing the hydrochloric acid-containing solutions of the waxberry leaf proanthocyanidin and the EGCG with the same hydrochloric acid concentration at a volume ratio of 1:2 to 2:1 for a reaction at 20-60 °C for 40 minutes, and then conducting drying and separation purification to obtain the prodelphinidin B9 gallate, wherein the prodelphinidin B9 gallate comprises a prodelphinidin B-3'-gallate and a prodelphinidin B-3,3'-digallate.
2. The chemical synthesis method according to claim 1, wherein a solvent used in the hydrochloric acid-containing solution comprises methanol and/or ethanol.
3. The chemical synthesis method according to claim 1, wherein the waxberry leaf proanthocyanidin has a purity of 86.4%; and the EGCG has a purity greater than or equal to 98%.
4. The chemical synthesis method according to claim 1, wherein a drying method specifically comprises: conducting rotary evaporation on a reaction solution obtained 40 minutes after the reaction at 40°C to remove methanol and a small amount of water, so as to obtain a dry powder of a crude reaction product.
5. The chemical synthesis method according to claim 1, wherein a separation purification method specifically comprises: using an S series X5H preparation column, acetonitrile containing 0.5 vol% acetic acid as a mobile phase A and ultrapure water as a mobile phase B; dissolving the crude reaction product in a mixture of the mobile phase A and the mobile phase B at a volume ratio of 88:12 to prepare a mg/mL solution; introducing 2 mL of a sample, and conducting elution purification with the mobile phases at a flow rate of 5 mL/min and an elution gradient of 12-27 vol% B for 0-10 minutes, 60 vol% B for 10-20 minutes and 12 vol% B for 20-26 minutes; and setting a detection wavelength to be 280 nm, collecting an effluent at 5.5-6.0 minutes according to a liquid phase 9 spectrum, conducting rotary evaporation on the effluent at 40°C to remove the acetonitrile, and then conducting freeze-drying to obtain a purified prodelphinidin B9 gallate.
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