CN102643259A - Ultrasonic preparation method of myrica rubra leaf proanthocyanidin oligomer - Google Patents
Ultrasonic preparation method of myrica rubra leaf proanthocyanidin oligomer Download PDFInfo
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- CN102643259A CN102643259A CN2012101055214A CN201210105521A CN102643259A CN 102643259 A CN102643259 A CN 102643259A CN 2012101055214 A CN2012101055214 A CN 2012101055214A CN 201210105521 A CN201210105521 A CN 201210105521A CN 102643259 A CN102643259 A CN 102643259A
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Abstract
The invention discloses a preparation method of a myrica rubra leaf proanthocyanidin oligomer, which comprises the following steps of: adding myrica rubra leaf proanthocyanidin extractive with the purity larger than or equal to 50% and ethanol used as a solvent into a container to obtain mixture liquid; ultrasonically processing the mixture liquid at the temperature of 5-50 DEG C and the ultrasonic frequency of 20khz for 30-80 minutes, wherein the dosage ratio of the myrica rubra leaf proanthocyanidin extractive with the purity larger than or equal to 50% to the ethanol is 10g of myrica rubra leaf proanthocyanidin extractive with the purity larger than or equal to 50%/20-40ml of ethanol; and (2) filtering a product obtained in the step (1) and carrying out chromatograph on the obtained filtrate to obtain a myrica rubra leaf proanthocyanidin oligomer. According to the method disclosed by the invention, a large content of myrica rubra leaf proanthocyanidin oligomer with the polymerization degree less than or equal to 4 can be obtained.
Description
Technical field
The present invention relates to the functional food field, particularly food vegetable chemistry component field.
Background technology
Proanthocyanidin is one type of flavan-3-alcohol class monomer and C4-C8 thereof or the C4-C6 key polymeric polyhydroxy phenol compounds that is formed by connecting; Molecular skeleton is C6-C3-C6, is the secondary metabolite in the growing process, gains the name because of in acidic medium, adding heat energy generation cyanidin(e); Proanthocyanidin has good anti-oxidant (Kim Y.J.; Yokozawa T.Modulation of oxidative stress and melanogenesis by proanthocyanidins.Biological & Pharmaceutical Bulletin.2009,32 (7), 1155-1159.), anticancer (Lu J.M.; Zhang K.Q.; Chen S.A., Wen W.Grape seed extract inhibits VEGF expression via reducing HIF-1alpha protein expression.Carcinogenesis.2009,30 (4); 636-644.), prevention and treatment cardiovascular disorder (Karthikeyan K.; Bai B.R.S., Devaraj S.N.Cardioprotective effect of grape seed proanthocyanidins on isoproterenol-induced myocardial injury in rats.International Journal of Cardiology.2007,115; (3); 326-333.) and anti-diabetic and complication (Lee Y.A., Kim Y.J., Cho E.J.; Yokozawa T.Ameliorative Effects of Proanthocyanidin on Oxidative Stress and Infl ammation in Streptozotocin-Induced Diabetic Rats.Journal of Agricultural and Food Chemistry 2007; 55,9395-9400.) etc. biological activity has been widely used in food, makeup and medicine and other fields.
The biological activity of proanthocyanidin is closely related with its polymerization degree, and the polymerization degree is regarded as the poly proanthocyanidin greater than 5.Influenced the activity of phenolic hydroxyl group because of its molecular weight is big with steric effect, caused its biological activity to reduce, and exist with multimeric forms more than the proanthocyanidin in the natural phant, therefore, the Study on degradation of proanthocyanidin receives extensive concern.At present, the degradation method of studying more proanthocyanidin catalysis hydrogen arranged, separate the chemical process of sulfurous acid degraded (Du Xiao, Tang Wei, Liao Xuepin. the Pd/C catalytic hydrogenolytic cleavage research of tamarack poly proanthocyanidin. chemical research and application, 2005,17 (4): 456; Tian Yaxin, the king ships, Han Xiaoyun; Liu Jiwei, Kang Chuanhong. the condition optimizing of sulfurous method degraded seed of Fructus Hippophae proanthocyanidin, Northeast Forestry University's journal; 2012,40 (1): 108-113) with method (Wang Hengyong, the preliminary study of fungus degrading sea-buckthorn proanthocyanidin of microbiological deterioration; Heilongjiang University's [Master's thesis], Harbin: 2010,5.7).
Find Folium Myricae rubrae proanthocyanidin content very high (about 110mg/g DW) after deliberation, structure is identified and is found to be mainly former delphinidin; Do not find to prepare the research and the report of Folium Myricae rubrae proanthocyanidin oligomer with UW.
Summary of the invention
The technical problem that the present invention will solve provides a kind of preparation method of Folium Myricae rubrae proanthocyanidin oligomer, adopts method of the present invention can obtain the Folium Myricae rubrae proanthocyanidin oligomer of the polymerization degree≤4 of big content.
In order to solve the problems of the technologies described above, the present invention provides a kind of preparation method of Folium Myricae rubrae proanthocyanidin oligomer, may further comprise the steps:
1), in container, add the Folium Myricae rubrae proanthocyanidin extract of purity (being mass content) >=50% and as the ethanol of solvent, mixed liquor; With said mixed liquor supersound process 30～80 minutes under-5～50 ℃ temperature, 20khz ultrasonic frequency;
The Folium Myricae rubrae proanthocyanidin extract of purity >=50% with the consumption of ethanol ratio is: the Folium Myricae rubrae proanthocyanidin extract of 10g purity >=50%/20～40ml ethanol;
2), with the step 1) products therefrom through filtering, the filtrating of gained is carried out chromatographic separation, Folium Myricae rubrae proanthocyanidin oligomer.
As the preparing method's of Folium Myricae rubrae proanthocyanidin oligomer of the present invention improvement, the supersound process in the step 1) is:
The container that mixed liquor is housed is placed in the low temperature thermostat bath; Select sonde-type pulse ultrasonic wave instrument for use, 1～1.5cm under the liquid of probe insertion mixed liquor, the degree of depth of mixed liquor (being liquid level) keeps 4～8cm; Burst length is 1～4s; Dutycycle is 30%～90%, and controlled temperature is-5～50 ℃ in the low temperature thermostat bath, and the sound intensity is 60.55～544.59W/cm
2, the treatment time is 30～80 minutes.
As the preparing method's of Folium Myricae rubrae proanthocyanidin oligomer of the present invention further improvement, step 2) in chromatographic separation be:
Liquid chromatograph is Agilent 1100Series, and detector is the UV detector, and the detection wavelength is 280nm; Chromatographic column is Luna Silica (250 * 4.6mm, i.d.5-μ m, Phenomenex Inc.; Darmstadt, Germany), sample size is 10 μ L; Flow velocity (flow velocity of gradient elution) is 1mL/min, and column temperature is 37 ℃;
Moving phase is made up of mobile phase A, Mobile phase B and moving phase C, and mobile phase A is a methylene dichloride, and Mobile phase B is a methyl alcohol, and moving phase C is that acetate mixes by 1: 1 volume ratio with water and gets;
In the gradient elution:
The volumetric concentration of moving phase C is constant to be 4%;
During 0～20min, the volumetric concentration of Mobile phase B is 14～23.6%;
During 20～50min, the volumetric concentration of Mobile phase B is 23.6～40%;
During 50～55min, the volumetric concentration of Mobile phase B is 40～86%;
During 55～60min, the volumetric concentration of Mobile phase B is 86%;
During 60～65min, the volumetric concentration of Mobile phase B is 86～14%;
Elutriant lyophilize in collection 30～60min time period gets Folium Myricae rubrae proanthocyanidin oligomer to constant weight.
Further improvement as the preparation method of Folium Myricae rubrae proanthocyanidin oligomer of the present invention: the diameter of probe is 10mm, and container is dark opaque container (purpose is the oxidation of avoiding illumination to cause).
Further improvement as the preparation method of Folium Myricae rubrae proanthocyanidin oligomer of the present invention:
Controlled temperature is 200W/cm for-5 ℃, the sound intensity in low temperature thermostat bath
2, the treatment time is when being 60 minutes, the Folium Myricae rubrae proanthocyanidin oligomer of gained with the polymerization degree be 2 be main;
Controlled temperature is that 40 ℃, the sound intensity are 100W/cm in low temperature thermostat bath
2, the treatment time is when being 70 minutes, the Folium Myricae rubrae proanthocyanidin oligomer of gained with the polymerization degree be 4 be main.
In the present invention, the cryodesiccated condition of elutriant is-45～-55 ℃, and the time was generally 20～28 hours.
The preparation method of Folium Myricae rubrae proanthocyanidin oligomer of the present invention, different oligomer content can be effectively controlled through temperature, the sound intensity, action time.
In the present invention, the polymerization degree adopts the method for NP-HPLC-DAD to detect.
In the present invention, the variable power scope of sonde-type pulse ultrasonic wave instrument is 0-950W.
The Folium Myricae rubrae proanthocyanidin extract of the purity (mass content) >=50% that the present invention is used for example can be according to the Yang that has published, HH; Ye, XQ; Liu, DH; Chen, JC; Zhang, JJ; Shen, Y; Yu; D Characterization of Unusual Proanthocyanidins in Leaves of Bayberry (Myrica rubra; Journal of Agricultural and Food Chemistry.2011,59 (5): 1622-1629 prepares.
The present invention has following advantage and effect:
1, can be used for the preparation of the oligomer of the former delphinidin (being the Folium Myricae rubrae proanthocyanidin extract of the red bayberry gained of different varieties) in the different varieties red bayberry leaf;
2, the advantage that has environmental protection, convenience, degraded ratio easy to control.
3, the gained oligomer can be used for the evaluation of the biological activity effect of the former delphinidin of different polymerization degree.
Embodiment
The preparation method of embodiment 1, a kind of Folium Myricae rubrae proanthocyanidin oligomer, carry out following steps successively:
1), takes by weighing the Folium Myricae rubrae proanthocyanidin extract of 10mg purity (mass content) >=50%; Join and be equipped with in the brown mother glass pipe of 30ml alcoholic acid; Get mixed liquor.
Above-mentioned Folium Myricae rubrae proanthocyanidin extract is from the Folium Myricae rubrae of water chestnut kind, to obtain; After the acid catalysis degraded, adopt the HPLC religious services or rituals to detect earlier: mean polymerisation degree is 8.0; Be mainly: the polymerization degree be 2 account for 22%; The polymerization degree be 3 account for 21%, the polymerization degree be 4 18%, the polymerization degree greater than 4 account for 39%.
The brown mother glass pipe that mixed liquor is housed places low temperature thermostat bath, selects sonde-type pulse ultrasonic wave instrument (ultrasonic frequency is 20khz) for use, 1cm (promptly the top of probe is 1cm apart from liquid level) under the liquid of probe (diameter of probe is 10mm) insertion mixed liquor; The degree of depth of mixed liquor keeps 4cm; Burst length is 2s, and dutycycle is 66.7%, and controlled temperature is-5 ℃ in the low temperature thermostat bath; Treatment time is 60 minutes, and the sound intensity is 180W/cm
2(power that is ultrasonic instrument is 180W).
2), with the step 1) products therefrom through filtering, the filtrating of gained is carried out chromatographic separation, chromatographic separation condition is specially:
Liquid chromatograph is Agilent 1100Series, and detector is the UV detector, and the detection wavelength is 280nm; Chromatographic column is Luna Silica (250 * 4.6mm, i.d.5-μ m, Phenomenex Inc.; Darmstadt, Germany), sample size is 10 μ L; Flow velocity (flow velocity of gradient elution) is 1mL/min, and column temperature is 37 ℃
Moving phase is made up of mobile phase A, Mobile phase B and moving phase C, and mobile phase A is a methylene dichloride, and Mobile phase B is a methyl alcohol, and moving phase C is that acetate mixes by 1: 1 volume ratio with water and gets;
In the gradient elution:
The volumetric concentration of moving phase C is constant to be 4%;
During 0～20min, the volumetric concentration of Mobile phase B is 14～23.6%; All the other are mobile phase A;
During 20～50min, the volumetric concentration of Mobile phase B is 23.6～40%; All the other are mobile phase A;
During 50～55min, the volumetric concentration of Mobile phase B is 40～86%; All the other are mobile phase A;
During 55～60min, the volumetric concentration of Mobile phase B is 86%; All the other are mobile phase A;
During 60～65min, the volumetric concentration of Mobile phase B is 86～14%; All the other are mobile phase A;
Collect elutriant lyophilize in 30～60min time period (51 ℃ lyophilize about 24 hours) to constant weight, Folium Myricae rubrae proanthocyanidin oligomer 4mg.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 90% is the oligomer of the polymerization degree≤4.
Embodiment 2, make controlled temperature in the low temperature thermostat bath among the embodiment 1 into 15 by-5 ℃, the sound intensity is by 180W/cm
2Make 300W/cm into
2, the treatment time made 50 into by 60 minutes; All the other are with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 3mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 67% is the oligomer of the polymerization degree≤4.
Embodiment 3, make controlled temperature in the low temperature thermostat bath among the embodiment 1 into 45 ℃ by-5 ℃, the sound intensity makes 400W into by 180W, and the treatment time made into 70 minutes by 60 minutes; All the other are with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 3.5mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 79% is the oligomer of the polymerization degree≤4.
Embodiment 4, change the liquid level among the embodiment 1 (being the degree of depth of mixed liquor) into 6cm by 4cm, the burst length is that 2s changes 4s into, and dutycycle makes 90% into by 66.7%, and all the other are fully with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 2.8mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 63% is the oligomer of the polymerization degree≤4.
Embodiment 5, change the liquid level among the embodiment 1 (being the degree of depth of mixed liquor) into 8cm by 4cm, the burst length is that 2s changes 5s into, and dutycycle makes 30% into by 66.7%, and all the other are fully with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 2.75mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 62% is the oligomer of the polymerization degree≤4.
Embodiment 6, be from the Folium Myricae rubrae of charcoal plum kind, to obtain with the Folium Myricae rubrae proanthocyanidin extract among the embodiment 1 instead; This Folium Myricae rubrae proanthocyanidin extract adopts the HPLC religious services or rituals to detect earlier after the acid catalysis degraded: mean polymerisation degree is 9.6; Be mainly: the polymerization degree be 2 account for 22%; The polymerization degree be 3 account for 17%, the polymerization degree be 4 account for 19%, the polymerization degree greater than 4 account for 42%.
All the other are fully with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 3.8mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 85% is the oligomer of the polymerization degree≤4.
Embodiment 7, be from the Folium Myricae rubrae of raisin kind, to obtain with the Folium Myricae rubrae proanthocyanidin extract among the embodiment 1 instead; This Folium Myricae rubrae proanthocyanidin extract adopts the HPLC religious services or rituals to detect earlier after the acid catalysis degraded: mean polymerisation degree is 10.1; Be mainly: the polymerization degree be 2 account for 21%; The polymerization degree be 3 account for 17%, the polymerization degree be 4 account for 17%, the polymerization degree greater than 4 account for 45%.
All the other are fully with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 3.6mg that gets.
Detect through HPLC method detection method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 81% is the oligomer of the polymerization degree≤4.
Comparative Examples 1, make the solvent among the embodiment 1 into methyl alcohol by ethanol, all the other are with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 2.8mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 63% is the oligomer of the polymerization degree≤4.
Comparative Examples 2, make the solvent among the embodiment 1 into propyl alcohol by ethanol, all the other are with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 3.2mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 72% is the oligomer of the polymerization degree≤4.
Comparative Examples 3, make the burst length among the embodiment 1 into 500ms by 2s, all the other are with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 2.7mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 61% is the oligomer of the polymerization degree≤4.
Comparative Examples 4, make the burst length among the embodiment 1 into 6s by 2s, all the other are with embodiment 1.
The final Folium Myricae rubrae proanthocyanidin oligomer 3.9mg that gets.
Detect through the HPLC method, in the above-mentioned Folium Myricae rubrae proanthocyanidin oligomer, 76% is the oligomer of the polymerization degree≤4.
At last, it is also to be noted that what more than enumerate only is several specific embodiments of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (4)
1. the preparation method of Folium Myricae rubrae proanthocyanidin oligomer is characterized in that may further comprise the steps:
1), in container, add the Folium Myricae rubrae proanthocyanidin extract of purity >=50% and as the ethanol of solvent, mixed liquor; With said mixed liquor supersound process 30～80 minutes under-5～50 ℃ temperature, 20khz ultrasonic frequency;
The Folium Myricae rubrae proanthocyanidin extract of said purity >=50% with the consumption of ethanol ratio is: the Folium Myricae rubrae proanthocyanidin extract of 10g purity >=50%/20～40ml ethanol;
2), with the step 1) products therefrom through filtering, the filtrating of gained is carried out chromatographic separation, Folium Myricae rubrae proanthocyanidin oligomer.
2. the preparation method of Folium Myricae rubrae proanthocyanidin oligomer according to claim 1 is characterized in that, the supersound process in the said step 1) is:
The container that mixed liquor is housed is placed in the low temperature thermostat bath; Select sonde-type pulse ultrasonic wave instrument for use, 1～1.5cm under the liquid of probe insertion mixed liquor, the degree of depth of mixed liquor keeps 4～8cm; Burst length is 1～4s; Dutycycle is 30%～90%, and controlled temperature is-5～50 ℃ in the low temperature thermostat bath, and the sound intensity is 60.55～544.59W/cm
2, the treatment time is 30～80 minutes.
3. the preparation method of Folium Myricae rubrae proanthocyanidin oligomer according to claim 2 is characterized in that: the chromatographic separation said step 2) is:
Liquid chromatograph is Agilent 1100 Series, and detector is the UV detector, and the detection wavelength is 280nm, and chromatographic column is Luna Silica, and sample size is 10 μ L, and flow velocity is 1mL/min, and column temperature is 37 ℃;
Moving phase is made up of mobile phase A, Mobile phase B and moving phase C, and mobile phase A is a methylene dichloride, and Mobile phase B is a methyl alcohol, and moving phase C is that acetate mixes by 1: 1 volume ratio with water and gets;
In the gradient elution:
The volumetric concentration of moving phase C is constant to be 4%;
During 0～20min, the volumetric concentration of Mobile phase B is 14～23.6%;
During 20～50min, the volumetric concentration of Mobile phase B is 23.6～40%;
During 50～55min, the volumetric concentration of Mobile phase B is 40～86%;
During 55～60min, the volumetric concentration of Mobile phase B is 86%;
During 60～65min, the volumetric concentration of Mobile phase B is 86～14%;
Elutriant lyophilize in collection 30～60min time period gets Folium Myricae rubrae proanthocyanidin oligomer to constant weight.
4. the preparation method of Folium Myricae rubrae proanthocyanidin oligomer according to claim 3 is characterized in that: the diameter of said probe is 10mm, and said container is dark opaque container.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924422A (en) * | 2012-09-10 | 2013-02-13 | 华南理工大学 | Method for preparing oligomeric proanthocyanidins by enhanced degradation under pulsed electric field |
| CN105925008A (en) * | 2016-07-11 | 2016-09-07 | 李旭颖 | Production method of waxberry red pigment |
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| US20240182435A1 (en) * | 2021-05-21 | 2024-06-06 | Zhejiang University | Chemical synthesis method of prodelphinidin b9 gallate |
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|---|---|---|---|---|
| CN1680359A (en) * | 2005-01-12 | 2005-10-12 | 天津科技大学 | Purification of oligo-proanthocyanidin from grape seed by membrane ultrafilter method |
| CN1850133A (en) * | 2006-03-09 | 2006-10-25 | 中国林业科学研究院林产化学工业研究所 | Method for extracting anti-oxygenation active material from Chinese waxmyrtle Bark |
| CN101845035A (en) * | 2009-03-24 | 2010-09-29 | 上海医药工业研究院 | Method for extracting oligomeric proanthocyanidins |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1680359A (en) * | 2005-01-12 | 2005-10-12 | 天津科技大学 | Purification of oligo-proanthocyanidin from grape seed by membrane ultrafilter method |
| CN1850133A (en) * | 2006-03-09 | 2006-10-25 | 中国林业科学研究院林产化学工业研究所 | Method for extracting anti-oxygenation active material from Chinese waxmyrtle Bark |
| CN101845035A (en) * | 2009-03-24 | 2010-09-29 | 上海医药工业研究院 | Method for extracting oligomeric proanthocyanidins |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102924422A (en) * | 2012-09-10 | 2013-02-13 | 华南理工大学 | Method for preparing oligomeric proanthocyanidins by enhanced degradation under pulsed electric field |
| CN102924422B (en) * | 2012-09-10 | 2015-03-11 | 华南理工大学 | Method for preparing oligomeric proanthocyanidins by enhanced degradation under pulsed electric field |
| CN105925008A (en) * | 2016-07-11 | 2016-09-07 | 李旭颖 | Production method of waxberry red pigment |
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