WO2022105726A1 - Procédé de production de granulés contenant du lycopène ayant un effet anti-oxydation efficace - Google Patents

Procédé de production de granulés contenant du lycopène ayant un effet anti-oxydation efficace Download PDF

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WO2022105726A1
WO2022105726A1 PCT/CN2021/130819 CN2021130819W WO2022105726A1 WO 2022105726 A1 WO2022105726 A1 WO 2022105726A1 CN 2021130819 W CN2021130819 W CN 2021130819W WO 2022105726 A1 WO2022105726 A1 WO 2022105726A1
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lycopene
ganoderma lucidum
lucidum spore
spore powder
antioxidant effect
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PCT/CN2021/130819
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Chinese (zh)
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冯鹏
王连安
王颖
周亚杰
钱一帆
冯敏
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中科健康产业集团股份有限公司
南京中科药业有限公司
中科健康产业集团江苏药业有限公司
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/01—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/06—Fungi, e.g. yeasts
    • A61K36/07—Basidiomycota, e.g. Cryptococcus
    • A61K36/074—Ganoderma
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1664—Compounds of unknown constitution, e.g. material from plants or animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1682—Processes
    • A61K9/1694—Processes resulting in granules or microspheres of the matrix type containing more than 5% of excipient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the invention belongs to the field of biotechnology, and in particular relates to a method for producing lycopene-containing granules with high-efficiency antioxidant effect.
  • Lycopene is a functional edible natural pigment, belonging to an important carotenoid, widely present in fruits and vegetables, especially in tomatoes with the highest content. Lycopene is a straight-chain hydrocarbon composed of 11 conjugated carbon-carbon double bonds, the molecular formula is C 40 H 56 , and the pure crystalline product is dark red. Lycopene is widely distributed in various organs and tissues of the human body, and exists in a cis configuration. The cis configuration and the trans configuration can be converted into each other according to different environments. But almost all lycopene derived from natural plants is in the trans configuration, which is the most thermostable.
  • Oxidative stress damage refers to tissue damage caused by excessive production of reactive oxygen species and reactive nitrogen radicals in the body when the body is subjected to harmful stimuli, or the weakening of the enzyme system for scavenging oxidative free radicals. Oxidative stress damage is an important factor leading to human skin aging. It damages cells and tissues, which can lead to degeneration of body functions, and is also the main factor causing nerve damage in cardiovascular and cerebrovascular diseases. Proper supplementation of antioxidants can alleviate oxidative stress damage in the body. In recent years, most of the research on new antioxidative drugs has focused on natural products that can be extracted from the daily diet, because these products have few side effects. Natural antioxidants have always been a research hotspot in the preventive medicine and health care industry for various middle-aged and elderly chronic diseases such as coronary heart disease, hyperlipidemia, diabetes, and neurodegenerative diseases.
  • the antioxidant effect of lycopene is mainly manifested in that it can quench singlet oxygen and scavenge free radicals.
  • the rate constant of scavenging singlet oxygen is 100 times that of antioxidant vitamin E and more than 2 times that of ⁇ -carotene. It has important physiological functions in the prevention and treatment of prostate cancer, lung cancer, and regulation of immunity, and has become a focus of international research on functional food ingredients.
  • Hypochlorous acid can lead to tissue oxidation in cardiovascular diseases by modifying proteins, deoxyribonucleic acid, and ribonucleic acid, while lycopene has the effect of scavenging hypochlorous acid, which can reduce the body damage caused by hypochlorous acid.
  • lycopene has a protective effect on the nervous system.
  • Lycopene can reduce the expression of inflammatory factors by inhibiting related inflammatory pathways, reduce the level of inflammation in the body, and inhibit the apoptosis pathway, reducing the loss of nerve cells and apoptosis. It can improve the antioxidant capacity of nerve cells, inhibit the production of reactive oxygen species, and exert a neuroprotective effect.
  • the combination of lycopene and other substances can enhance its antioxidant effect, and its clinical use has bright prospects.
  • lycopene contains a large number of unsaturated structures, it is easily degraded by oxidation under the action of light, heat and oxygen, and is prone to degradation and isomerization during processing and storage, resulting in reduced physiological activity, and lycopene is a kind of Fat-soluble carotenoids are insoluble in water, and these characteristics greatly limit its promotion and application.
  • raw materials for lycopene there are mainly two kinds of raw materials for lycopene, namely, semi-fluid raw materials (oleoresin) dissolved in fat-soluble solvents and granular embedded solid raw materials.
  • the granular embedded raw material after macromolecular embedding has a great advantage in stability, and will not be damaged by strong acid in gastric juice after taking, so that its bioavailability is improved.
  • lycopene products cover the fields of medicine, health care and cosmetics.
  • injection drugs with lycopene as the main agent which are used to prevent ultraviolet burns, remove stains, protect the skin and adjuvant cancer treatment;
  • All kinds of health care products with lycopene as the main component are mainly used for anti-oxidation, anti-aging, enhancing immunity, regulating blood lipids and preventing cancer and anti-cancer; some supplements with lycopene are added to jam, meat products,
  • lycopene is used as a preservative and added to edible oil to prevent the oxidative rancidity of the oil and prolong the shelf life of the oil.
  • the preparations containing lycopene are mainly soft capsules, which are made by mixing lycopene oleoresin with soybean oil, safflower oil and other edible oils, and filling soft capsules.
  • the lycopene product of this dosage form has poor stability.
  • the embedding process is also widely used in lycopene products, including hard capsules, granules, etc., but many excipients are used, and the content of active ingredients is low, generally not more than 3%.
  • the object of the present invention is to overcome the above-mentioned deficiencies, and provide a method for producing lycopene-containing particles with high-efficiency antioxidant effect.
  • the lycopene-containing granules obtained by the method have high content of effective components, convenient preparation and high stability.
  • a production method of lycopene-containing particles with high-efficiency antioxidant effect comprising the following steps:
  • Ganoderma lucidum spore powder with a wall breaking rate of 90-92% extract Ganoderma lucidum spore oil through CO 2 supercritical extraction process to obtain degreasing Ganoderma lucidum spore powder, and combine the defatted Ganoderma lucidum spore powder with lycopene oleoresin in a ratio of 1-2:1 -2 weight ratio mixing spray granulation.
  • the above-mentioned Ganoderma lucidum spore powder is the Ganoderma lucidum spore powder erupted from Red Ganoderma lucidum. Defatted Ganoderma lucidum spore powder can still see the complete shape of Ganoderma lucidum spores under a 600x microscope.
  • the above-mentioned CO 2 supercritical extraction process is as follows: the extraction temperature is 35 ⁇ 36° C., the extraction pressure is 25 ⁇ 28Mpa, the extraction time is 6 ⁇ 7 hours, the CO 2 flow rate is 400 ⁇ 600L/h, and the sample loading volume is 38kg each time.
  • the preferred CO2 supercritical extraction process is as follows: the extraction temperature is 35°C, the extraction pressure is 25Mpa, the extraction time is 7 hours, and the CO2 flow rate is 500L/h.
  • the above mixing method is as follows: mixing lycopene oleoresin with a little absolute ethanol to obtain lycopene oleoresin alcoholate to increase its fluidity. Put the defatted Ganoderma lucidum spore powder into the fluidized bed granulator, in the fluidized bed granulator, the lycopene oleoresin alcoholate is atomized from the nozzle and sprayed onto the fluidized bed layer by compressed air, and it is in a fluidized state On the broken wall of Ganoderma lucidum spore powder, make it wet and mix well, and flow granulation.
  • the conditions used for spray granulation are: the atomization speed of the nozzle is 40-100 mL/min, the atomization particle size is 10-12 ⁇ m, and the one-time sample loading of the fluidized bed is 8-10 kg.
  • the atomization speed of the nozzle is 100 mL/min, the atomization particle size is 10 ⁇ m, the one-time sample loading of the fluidized bed is 8 kg, and flow granulation is carried out.
  • the conditions can be fully mixed, and after granulation, the prepared granules are placed in a cool and dry place to dry in the shade.
  • the mixing weight ratio of the above-mentioned defatted Ganoderma lucidum spore powder and lycopene oleoresin is 1:1.
  • Mixing in this ratio can increase the lycopene content to the maximum amount, and the particles are uniform.
  • the beneficial effects of the present invention are: the granule product prepared by the method of the present invention has high content of active ingredients, content of lycopene > 6%, content of polysaccharide > 0.8%, good stability, and efficient anti-oxidation. effect.
  • Figure 1 is a diagram showing the protective effect of lycopene particles on the oxidative degradation of BSA caused by AAPH according to an embodiment of the present invention.
  • Figure 2 is a graph showing the protective effect of Example lycopene particles on U87 cells from oxidative damage.
  • Fig. 3 is a graph showing the effect of lycopene particles on the content of 8-OH-dG in an embodiment.
  • lycopene oleoresin is purchased from Chenguang Biotechnology Group Co., Ltd., is a dark red liquid oil, and its lycopene content is greater than 12%.
  • the CO2 supercritical extraction process is as follows: the extraction temperature is 35°C, and the extraction pressure is 25Mpa , the extraction time was 7 hours, the flow rate of CO 2 was 500 L/h, and the amount of each sample was 38 kg.
  • Defatted Ganoderma lucidum spore powder can still see the complete shape of Ganoderma lucidum spores under a 600x microscope. Defatted Ganoderma lucidum spore powder and lycopene oleoresin were taken in a weight ratio of 1:1.
  • the defatted Ganoderma lucidum spore powder into the fluidized bed granulator, mix the lycopene oleoresin with a little anhydrous ethanol, and then spray the lycopene oleoresin mixed with the ethanol from the nozzle and spray it to the On the fluidized bed layer, the broken-wall Ganoderma lucidum spore powder in fluidized state is wetted, fully mixed, and flow granulated.
  • the sample loading capacity of the bed is 8kg at a time; the prepared granules are placed in a cool and dry place to dry in the shade.
  • lycopene particles Three batches of samples were made in parallel, the contents of lycopene in the obtained products were 8.36%, 8.29%, 8.28%, and the contents of polysaccharides were 1.23%, 1.25%, and 1.22, respectively. They are 1#, 2#, and 3# products (hereinafter referred to as lycopene particles).
  • the CO2 supercritical extraction process is as follows: the extraction temperature is 35°C, and the extraction pressure is 25Mpa , the extraction time was 7 hours, the flow rate of CO 2 was 500L/h, and the sample loading was 38kg each time. Defatted Ganoderma lucidum spore powder can still see the complete shape of Ganoderma lucidum spores under a 600x microscope.
  • the defatted Ganoderma lucidum spore powder and the lycopene oleoresin are fully mixed in a weight ratio of 1:1, and conventional dextrin and other auxiliary materials are added for granulation, and the obtained granule is a 4# product.
  • the CO2 supercritical extraction process is as follows: the extraction temperature is 35°C, and the extraction pressure is 25Mpa , the extraction time was 7 hours, the flow rate of CO 2 was 500 L/h, and the amount of each sample was 38 kg.
  • Defatted Ganoderma lucidum spore powder can still see the complete shape of Ganoderma lucidum spores under a 600x microscope. Defatted Ganoderma lucidum spore powder and lycopene oleoresin were taken in a weight ratio of 9:1.
  • the defatted Ganoderma lucidum spore powder into the fluidized bed granulator, mix the lycopene oleoresin with a little anhydrous ethanol, and then spray the lycopene oleoresin mixed with the ethanol from the nozzle and spray it to the On the fluidized bed layer, the broken-wall Ganoderma lucidum spore powder in the fluidized state is wetted, fully mixed, and flow granulated.
  • the one-time sample loading of the chemical bed is 8kg; the prepared granules are placed in a cool and dry place to dry in the shade.
  • the obtained granules are 5# products.
  • the CO2 supercritical extraction process is: the extraction temperature is 40°C, and the extraction pressure is 30Mpa , the extraction time was 5 hours, the flow rate of CO 2 was 500 L/h, and the amount of each sample was 38 kg.
  • Defatted Ganoderma lucidum spore powder and lycopene oleoresin were taken in a weight ratio of 1:1.
  • the defatted Ganoderma lucidum spore powder into the fluidized bed granulator, mix the lycopene oleoresin with a little anhydrous ethanol, and then spray the lycopene oleoresin mixed with the ethanol from the nozzle and spray it to the flow through the compressed air.
  • the broken-wall Ganoderma lucidum spore powder in a fluidized state is wetted, fully mixed, and flow granulated.
  • the sample loading capacity of the bed is 8kg at a time; the prepared granules are placed in a cool and dry place to dry in the shade.
  • the obtained granule is 6# product.
  • the preparation method of the 4% ammonia buffer solution is as follows: firstly, 143 mL of ammonia water is added to 1 L of purified water and mixed evenly, and then the pH is adjusted to 9.8 with 85% phosphoric acid, thus obtaining the 4% ammonia buffer solution.
  • the stable tetrahydrofuran solution was prepared by dissolving 0.25g BHT in 1L tetrahydrofuran.
  • the mobile phase solution was a dichloromethane and methanol solution with a volume ratio of 90:10.
  • the standard curve solution was injected under chromatographic conditions, and the concentration was taken as the abscissa and the peak area as the ordinate to obtain the standard curve equation;
  • the sample was injected under the same chromatographic conditions, separated by a reverse-phase high-efficiency separation chromatographic column, and detected by a UV detector, and the sample to be tested was qualitatively determined by the retention time; according to the above standard curve equation, the retention time and peak area were used to calculate the sample to be tested. lycopene content.
  • UV detector detection wavelength 472nm
  • Injection volume 5 ⁇ L.
  • ⁇ The concentration of lycopene in the sample calculated according to the standard curve, ⁇ g/mL;
  • V concentration factor of the sample
  • m Weighing sample size of the sample, g.
  • Example 1 of the present invention (hereinafter referred to as lycopene particles), quercetin, lycopene oleoresin, defatted Ganoderma lucidum spore powder, AAPH (2,2'-azobisisobutylamidine dihydrochloride), Agarose and 8-OH-dG standards were purchased from Sigma, deoxyribose from BioRad, sodium dodecyl sulfonate (SDS) from Serva, and malignant glioma cells U87 from Lanzhou University School of Life Sciences, DMEM medium was purchased from Gibco in the United States, newborn bovine serum was produced by Hangzhou Sijiqing Company, and other reagents were of domestic analytical grade.
  • lycopene particles quercetin, lycopene oleoresin, defatted Ganoderma lucidum spore powder, AAPH (2,2'-azobisisobutylamidine dihydrochloride), Agarose and 8-OH
  • Antioxidants can reduce Fe 3+ to Fe 2+ , and form a soluble blue complex KFe[Fe(CN) 6 ] with potassium ferricyanide with maximum light absorption at 700 nm. Therefore, the stronger the reducing power, the larger the measured absorbance value.
  • Superoxide anion scavenging rate (%) [1-(A 1 -A 2 )/A 0 ] ⁇ 100 (A 0 is the absorbance without scavenger; A 1 is the absorbance with scavenger added; A 2 is absorbance without pyrogallol).
  • microsomes were extracted by thiobarbituric acid colorimetry, referring to the method of Liu Guoan et al., and diluted to 0.3 ⁇ 0.5g ⁇ L -1 . Take 300 ⁇ L of microsomes and add 100 ⁇ L of PBS and 300 ⁇ L of distilled water, then add 100 ⁇ L of samples with different concentrations, and replace the positive control with distilled water.
  • Tumor cells U87 were cultured in DEME complete medium containing 10% newborn bovine serum, streptomycin (100 ⁇ g ⁇ .L -1 ) and penicillin (100U ⁇ mL -1 ), and were cultured in a 5% CO 2 saturated humidity incubator (37°C), cells in logarithmic growth phase were used for experiments.
  • Cell growth rate (%) (A 1 -A 0 )/(A - A 0 ) ⁇ 100, where A 0 is the absorbance value of the blank group; A is the absorbance value of the control group; A 1 is the absorbance value of the experimental group.
  • U87 cells in the logarithmic growth phase were taken and seeded in 6-well plates at a concentration of 1 ⁇ 10 5 ⁇ mL -1 , 100 ⁇ L per well, and incubated for 24 hours.
  • different concentrations of lycopene were added to make the final concentration 1 , 5, 10 ⁇ mol ⁇ L -1 , incubated for 2h, and added H 2 O 2 with a final concentration of 100 ⁇ mol ⁇ L -1 ;
  • the control group and the injury group were respectively added with DEME complete medium containing 10% bovine serum and the final concentration was 100 ⁇ mol ⁇ L -1 L -1 of H 2 O 2 was incubated for 24h, DNA was extracted with Tiangen DP304-02 DNA extraction kit, DNA purity was determined, pre-loading was performed, and capillary electrophoresis was performed.
  • Quercetin is one of the common dietary antioxidants, and the activity of lycopene granules was compared with quercetin as a reference.
  • Table 1 shows the reducing power of lycopene particles with different concentrations. It can be seen that with the increase of the concentration, the reducing power is also increasing, which is positively correlated within the test range, and the absorbance value reaches 0.0975 at 100 ⁇ mol ⁇ L -1 . ⁇ L -1 quercetin has weaker activity than quercetin.
  • OH ⁇ and O 2 - ⁇ are the most representative free radicals, which can be produced in almost all aerobic organisms, while OH ⁇ is the most active and aggressive reactive oxygen species in organisms, and their abnormal production can damage important Such as protein, DNA and other biological macromolecules, causing damage to the body.
  • the scavenging ability of lycopene particles to OH ⁇ and O 2 - ⁇ was expressed as the concentration when the scavenging rate reached 50% - the half scavenging concentration (EC 50 ), and the results are shown in Table 2.
  • the EC 50 of lycopene particles for OH ⁇ was 0.03 mol ⁇ L -1 , while that of quercetin was 0.08 ⁇ mol ⁇ L -1 .
  • the EC 50 of lycopene granules to remove O 2 - ⁇ was 72.63 ⁇ mol ⁇ L -1 , while that of quercetin was 183.52 ⁇ mol ⁇ L -1 , indicating that lycopene granules had strong activity.
  • Table 5 shows that lycopene granules have inhibitory effect on lipid peroxidation in rat liver microsomes, the half-inhibitory concentration (IC 50 ) is 22.53 ⁇ mol ⁇ L -1 , and its inhibitory effect is stronger than that of quercetin (IC 50 is 29.14 ⁇ mol ⁇ L -1 ) L -1 ) was strong and showed good antioxidant activity.
  • Figure 1 shows the results of the protective effect of lycopene granules and quercetin on AAPH-induced BSA oxidative damage. Compared with the control, after the action of BSA and AAPH at 37°C, the bands of SDS-PAGE gel electrophoresis were obviously lighter, indicating that the bovine serum albumin was oxidatively degraded. After adding different concentrations of lycopene particles to the system, the degradation of BSA was inhibited as the concentration increased.
  • H 2 O 2 is an oxidative metabolite of organisms and is also a reactive oxygen species.
  • U87 cells were injured with 100 ⁇ mol ⁇ L -1 H 2 O 2 or pretreated with different concentrations of lycopene, and the protective effect of lycopene was evaluated by observing cell viability.
  • the peak area is proportional to the content of 8-OH-dG, that is, the higher the content, the more serious the DNA oxidative damage.
  • the peak area increased and the 8-OH-dG content increased.
  • 1 ⁇ mol ⁇ L -1 lycopene particles had no effect on this injury, while the peak area decreased when the concentration was 5 ⁇ mol ⁇ L -1 , and the concentration of 8-OH-dG decreased, showing a significant protective effect; in contrast, 10 ⁇ mol ⁇ L -1 L -1 also had a certain protective effect, but it was not as strong as the 5 ⁇ mol ⁇ L -1 group.
  • the anti-DNA damage activity of quercetin was not as strong as that of lycopene granules.

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Abstract

Procédé de production de granulés contenant du lycopène présentant un effet anti-oxydation efficace. Le procédé consiste : à extraire de l'huile de spores de Ganoderma lucidum à partir de poudre de spores de Ganoderma lucidum ayant un taux de sporodermes cassés compris entre 90 % et 92 % au moyen d'un procédé d'extraction au CO2 supercritique pour obtenir une poudre de spores de Ganoderma lucidum dégraissée ; et à mélanger la poudre de spores de Ganoderma lucidum dégraissée et la résine d'huile de lycopène selon un rapport pondéral de (1 à 2):(1 à 2), et à réaliser une granulation par pulvérisation sur ce dernier. Dans un produit granulaire préparé à l'aide du procédé, la teneur en constituant efficace est élevée, la teneur en lycopène est supérieure à 6 %, et la teneur en polysaccharides est supérieure à 0,8 % ; et le produit présente une bonne stabilité et a un effet anti-oxydation efficace.
PCT/CN2021/130819 2020-11-18 2021-11-16 Procédé de production de granulés contenant du lycopène ayant un effet anti-oxydation efficace WO2022105726A1 (fr)

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CN115125059A (zh) * 2022-06-15 2022-09-30 中科健康产业集团股份有限公司 一种去除灵芝孢子油中脂溶性有害成分的方法
CN115381092A (zh) * 2022-08-26 2022-11-25 吉林省爱康寿生物科技有限公司 一种灵芝孢子粉多糖与蓝莓粉复合咀嚼片及其制作工艺

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CN112569192A (zh) * 2020-11-18 2021-03-30 中科健康产业集团股份有限公司 一种具有高效抗氧化功效的含番茄红素颗粒的生产方法

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