WO2017095138A1 - Complexe de nanoparticules lipidiques contenant de la curcumine comprenant des ginsénosides - Google Patents
Complexe de nanoparticules lipidiques contenant de la curcumine comprenant des ginsénosides Download PDFInfo
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- WO2017095138A1 WO2017095138A1 PCT/KR2016/013964 KR2016013964W WO2017095138A1 WO 2017095138 A1 WO2017095138 A1 WO 2017095138A1 KR 2016013964 W KR2016013964 W KR 2016013964W WO 2017095138 A1 WO2017095138 A1 WO 2017095138A1
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- Prior art keywords
- curcumin
- lipid nanoparticle
- cancer
- complex
- containing lipid
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Definitions
- the present invention relates to a curcumin-containing lipid nanoparticle complex comprising ginsenosides, and more specifically, in order to improve the stability, dispersibility, and bioavailability of curcumin, the present invention relates to a curcumin-containing lipid nanoparticle complex in which curcumin is encapsulated inside a lipid nanoparticle that comprises ginsenosides and phospholipids, a method for preparing the curcumin-containing lipid nanoparticle complex, pharmaceutical composition for preventing or treating cancer comprising the curcumin-containing lipid nanoparticle complex, food composition for preventing or ameliorating cancer comprising the curcumin-containing lipid nanoparticle complex, and a method for preventing or treating cancer comprising a step of administering the curcumin-containing lipid nanoparticle complex.
- Curcumin which has been used as a food material for thousands of years as the main ingredient of turmeric, has been found to possess various physiologically active properties such as anti-oxidant, anti-inflammatory, and anti-cancer effects, and curcumin has attracted the attention of many researchers because it is expected to contribute to maintaining health, preventing diseases, etc.
- curcumin has been reported to block the absorption of cholesterol in the digestive tract and thereby reduce blood serum cholesterol, and recently curcumin has been used to prevent and treat various diseases such as hyperlipidemia, type-2 diabetes, arthritis, and Alzheimer’s disease.
- curcumin decomposes very quickly in the air and in the gut fluid (particularly in weakly alkaline intestinal fluid), and due to the insolubility thereof in water, curcumin is not absorbed during oral administration, and therefore exhibits many problems of not achieving the desired effect. That is, when curcumin is absorbed from natural products such as turmeric, even if consumed in a large amount, it may not be expected to achieve beneficial physiological benefits.
- the curcumin is metabolized at the rough endoplasmic reticulum of enterocytes while primarily passing through the enterocytes and at the liver cells, by glucuronidation (a type of conjugation reaction) and a sulfation reaction, and the unique antioxidant activity of curcumin is thereby lost.
- glucuronidation a type of conjugation reaction
- a sulfation reaction a type of conjugation reaction
- the unique antioxidant activity of curcumin is thereby lost.
- the international patent publication discloses a method for preparing a molecular complex by reacting curcumin with a phospholipid, based on a mole ratio in a range of 1:1 to 1:10 in an organic solvent, and the molecular complex, which is prepared by this method, is commercially available.
- the molecular complex is an insoluble substance, it is not easy to disperse and elute the complex in a digestive fluid such as gastric fluid and intestinal fluid, and when orally administered, the bioavailability of the molecular complex increases, but the level thereof is limited, which is a disadvantage.
- curcumin glucuronide and curcumin sulfate which are metabolites of curcumin, are detected in blood, while curcumin itself is not detected, and the metabolites are not known to exhibit the same beneficial physiological effects as curcumin, and therefore the utility of the molecular complex is questionable.
- the present inventors while improving the physical property of curcumin, have made extensive research efforts to develop a method capable of utilizing the unique physiological activity specific to curcumin, and confirmed that in the case of using a curcumin-containing lipid nanoparticle complex in which curcumin is encapsulated inside a lipid nanoparticle comprising ginsenosides and phospholipids, the stability, dispersibility, and bioavailability of curcumin were improved, and in addition, it exhibited an improved therapeutic effect against various kinds of cancer, thereby completing the present invention.
- One object of the present invention is to provide a curcumin-containing lipid nanoparticle complex, in which curcumin is encapsulated inside a lipid nanoparticle comprising ginsenosides and phospholipids.
- Another object of the present invention is to provide a method for preparing the curcumin-containing lipid nanoparticle complex.
- Another object of the present invention is to provide pharmaceutical composition preventing or treating cancer comprising the curcumin-containing lipid nanoparticle complex.
- Another object of the present invention is to provide food composition preventing or ameliorating cancer comprising the curcumin-containing lipid nanoparticle complex.
- Another object of the present invention is to provide a method for preventing or treating cancer comprising a step of administering the curcumin-containing lipid nanoparticle complex.
- the curcumin-containing lipid nanoparticle complex provided in the present invention can improve the stability, dispersibility, and bioavailability of curcumin by using ginsenosides, and it can be used to develop various curcumin-containing products.
- FIG. 1 is an electronic transmission microscope photograph illustrating the form in which the curcumin-containing lipid nanoparticle complex provided in the present invention is dispersed in water, where A is a photograph taken at a low magnification, and B is a photograph taken at a high magnification.
- FIG. 2 is a graph illustrating the results of evaluating the stability of the curcumin-containing lipid nanoparticle complex (the composition in Example 2-1) provided in the present invention.
- FIG. 3 is a photograph illustrating the phenomenon in which curcumin is educed when the molecular complex prepared according to the prior art is dispersed in water.
- FIG. 4 is a photograph illustrating the results of evaluating the dispersibility of the improved curcumin-containing lipid nanoparticle complex (the composition in Example 2-1) provided in the present invention, where A is a photograph illustrating the condition of the dispersed liquid after 1 week, and B is a photograph illustrating the condition of the dispersed liquid after 2 weeks.
- FIG. 5 shows a photograph (A) illustrating the shape of the improved curcumin-containing lipid nanoparticle complex (the composition in Example 3-1) provided in the present invention after dispersal thereof for 2 weeks, and shows a graph (B) illustrating the results of measuring the size of the lipid nanoparticle formed after dispersal thereof in water.
- FIG. 6 is a graph illustrating the result of evaluating the elution rate of the improved curcumin-containing lipid nanoparticle complex (the composition in Example 3-1).
- FIG. 7 is a graph illustrating the results of comparing the concentration changes of curcumin in blood over time, after the improved curcumin-containing lipid nanoparticle complex (the composition of Example 3-1) of the present invention is orally administered at different dosages.
- FIG. 8a is a graph illustrating the results of analyzing the anti-cancer activity of the curcumin-containing lipid nanoparticle complex (the composition of Example 3-1) of the present invention against colorectal cancer cells.
- FIG. 8b is a graph illustrating the results of analyzing the anti-cancer activity of the curcumin-containing lipid nanoparticle complex (the composition of Example 3-1) of the present invention against lung cancer cells.
- FIG. 8c is a graph illustrating the results of analyzing the anti-cancer activity of the curcumin-containing lipid nanoparticle complex (the composition of Example 3-1) of the present invention against breast cancer cells.
- FIG. 8d is a graph illustrating the results of analyzing the anti-cancer activity of the curcumin-containing lipid nanoparticle complex (the composition of Example 3-1) of the present invention against melanoma cells.
- the present inventors attempted to devise a new curcumin-containing lipid nanoparticle complex to improve the stability, dispersibility, and bioavailability of curcumin based on the structure of chylomicron, which is known as a transport carrier involved in the lipid absorption process in the body, by mixing curcumin and phospholipids at an appropriate ratio, dissolving the mixture in ethanol, and evaporating the ethanol under low pressure.
- the present inventors focused on ginsenosides, the chemical structure of which is similar to cholesterol which is a component of chylomicrons.
- ginseng contains a large amount of ginsenosides, a type of sterol, and the ginsenosides are structurally similar to cholesterol, but, unlike cholesterol, have many beneficial effects for health such as immunity, anti-inflammation, etc., and by using the ginsenosides, the present inventors attempted to develop a curcumin-containing lipid nanoparticle complex to improve the physical properties of curcumin by encapsulation thereof.
- curcumin is encapsulated inside a lipid nanoparticle that comprises ginsenosides and phospholipids.
- the curcumin-containing lipid nanoparticle obtained above When the curcumin-containing lipid nanoparticle obtained above is dissolved in water, it forms a lipid nanoparticle that is smaller than 1 micron in a core/shell structure, and the curcumin-containing lipid nanoparticle complex exists in a condition where curcumin is encapsulated inside a lipid nanoparticle that comprises ginsenosides and phospholipids, thereby improving the stability, dispersibility, and bioavailability of curcumin.
- the ginsenosides may be ginsenosides obtained by chemical synthesis through known methods, or obtained from ginseng or product thereof which comprises ginsenoside compounds.
- the ginsenosides are capable of having a role in preventing the elution of curcumin, which is encapsulated inside the membrane by external conditions when dispersed in water, and it was confirmed that in order to exhibit such effect, the mixing ratio between a ginsenoside and a phospholipid may be in a range of 20:1 to 1:20 (weight ratio), and the more specific mixing ratio may be in a range of 1:5 to 1:10 (weight ratio).
- the technique to prepare a curcumin-containing lipid nanoparticle complex that may improve the stability, dispersibility, and bioavailability of curcumin by using ginsenosides has not been known, and was invented for the first time by the present inventors.
- the curcumin-containing lipid nanoparticle complex provided in the present invention may improve the stability, dispersibility, and bioavailability of curcumin, and the complex may be used to prepare various curcumin-containing compositions.
- the present invention provides a curcumin-containing lipid nanoparticle complex, comprising: (a) a lipid nanoparticle comprising ginsenosides and phospholipids; and (b) a curcumin-containing lipid nanoparticle complex comprising curcumin which is encapsulated inside the lipid nanoparticle.
- ginsenoside used is not particularly limited thereto.
- the ginsenosides which include a small amount of sugar, exhibit the characteristics of insolubility in water, but excellent solubility in ethanol, and therefore they may be used to form a lipid nanoparticle with phospholipids.
- the ginsenosides may be obtained by chemical synthesis through known methods, or it may be obtained from ginseng or product thereof.
- the ginsenosides may be obtained by chemical synthesis through known methods, or it may be obtained by fermentation, or it may be obtained by acid or alkali hydrolysis of ginseng or product thereof.
- the product in the present invention may be, for example, red ginseng, black ginseng, or Tae-Guek ginseng, etc.
- ginseng saponin derived from processed ginseng
- red ginseng saponin derived from processed ginseng
- black ginseng saponin derived from processed ginseng
- Tae-Guek ginseng saponin derived from processed ginseng, red ginseng, black ginseng, or Tae-Guek ginseng , etc.
- the ginsenoside in the enzyme digestion method, may be obtained by adding ginseng or product thereof and an enzyme exhibiting a glycolytic activity (for example, beta-glucosidase, lactase, alpha-galactosidase, etc.) in an aqueous solution, reacting for 3 to 7 days at a temperature between 25°C and 55°C, and purifying the precipitated product.
- the ginsenosides in acid hydrolysis method, may be obtained by adding ginseng or product thereof into 0.1N-HCl, reacting for 3-5 hours, and purifying the precipitated product.
- alkali hydrolysis method the ginsenosides may be obtained by adding ginseng or product thereof into 0.1N-NaOH, reacting for 3-5 hours, and purifying the precipitated product.
- phospholipid means a lipid, as a type of a complex lipid, having a phosphate ester. Generally, it may be classified into glycerophospholipids composed of glycerols, and sphingophospholipids composed of sphingosine bases, and in particular, glycerophospholipids are known to account for more than 70% of phospholipids in living tissue.
- the phospholipids are present in microbial, plant, and animal systems and are one of the important constituents of various biological membranes, along with proteins.
- the phospholipids may be used to form a lipid nanoparticle with ginsenosides.
- lipid nanoparticle means a substance having a possible application as a drug delivery carrier for the delivery of lipophilic drugs in the body, and together with the development of nanotechnology, it may be in the form of a newly proposed drug delivery system or a pharmaceutical formulation.
- the lipid nanoparticle may be applied to the development of new therapeutic agents due to the inherent size-dependent property thereof.
- the lipid nanoparticle may be a proposed alternative drug delivery carrier to overcome the disadvantages of conventional colloidal carriers such as emulsions, liposomes, and polymeric nano- and micro-particles.
- the lipid nanoparticle shows a similar structure to conventional colloidal carriers such as emulsions, liposomes, and polymeric nano- and micro-particles, but the lipid nanoparticle may be a particle characterized by having a sub-micron diameter, for example, from 10 nm to 1000 nm.
- curcumin-containing lipid nanoparticle complex means a complex in which curcumin is encapsulated inside the lipid nanoparticle.
- the lipid nanoparticle is a particle characterized by having a diameter from 10 nm to 1000 nm, which is less than the diameter of conventional drug delivery carriers, and it may encapsulate various kinds of lipophilic drugs therein, but when curcumin is encapsulated as the drug, the curcumin is merely encapsulated inside the lipid nanoparticle without forming any chemical bond therewith, and may therefore form a simple complex.
- the curcumin-containing lipid nanoparticle complex provided in the present invention may further comprise additional components, in addition to the ginsenoside and phospholipid, for improving the encapsulation efficiency of curcumin.
- the site of the lipid nanoparticle may further comprise an enzyme-digested phospholipid, in addition to the ginsenoside and phospholipid.
- the water solubility of the lipid nanoparticle may increase, thereby improving the dispersibility and solubility of the lipid nanoparticle.
- the content thereof may be, for example, in a range of 0.1 to 5.0 (weight ratio) relative to the content of the phospholipid, as another example, 0.5 to 2.0 (weight ratio), and as another example, it may be 1.0 (weight ratio), but is not particularly limited thereto.
- a curcumin-containing lipid nanoparticle complex was prepared by using curcumin, phospholipids, and ginsenosides, and additionally an enzyme-digested phospholipids and a caprylic/capric triglyceride, and the characteristics of the curcumin-containing lipid nanoparticle complex were analyzed.
- a curcumin-containing lipid nanoparticle complex having a size smaller than 1 micron was formed, in which curcumin was encapsulated inside the lipid nanoparticle as a phospholipid complex (FIG.
- the present invention provides a method for preparing the curcumin-containing lipid nanoparticle complex.
- the method for preparing the curcumin-containing lipid nanoparticle complex of the present invention comprises steps of (a) mixing ginsenosides and phospholipids; (b) dissolving the mixture in a solvent; and (c) removing the solvent.
- curcumin, ginsenosides, and phospholipids that may be used are the same as described above, and the content of the curcumin and the mixing ratio between the ginsenosides and the phospholipids are the same as described above.
- the solvent it is possible to use an alcohol having 1 to 4 carbon atoms.
- the present invention provides a pharmaceutical composition for preventing or treating cancer comprising the curcumin-containing lipid nanoparticle complex.
- Curcumin is known to have anti-cancer activity, and the curcumin-containing lipid nanoparticle complex provided in the present invention can improve the stability, dispersibility, and bioavailability of the curcumin, and therefore if the curcumin-containing lipid nanoparticle complex of the present invention is used, curcumin may be more efficiently used and may be used for preventing or treating cancer.
- the curcumin-containing lipid nanoparticle complex after analyzing the anti-cancer activity of the curcumin-containing lipid nanoparticle complex provided in the present invention, it was confirmed that using the curcumin-containing lipid nanoparticle complex exhibited improved anti-cancer activity against the cells of colorectal cancer (FIG. 8a), lung cancer (FIG. 6b), breast cancer (FIG. 8c), and melanoma (FIG. 8d) compared to simply treating with curcumin alone.
- the curcumin-containing lipid nanoparticle complex provided in the present invention improves the bioavailability of encapsulated curcumin, and it was found that as a result, the curcumin-containing lipid nanoparticle complex provided in the present invention exhibited effective anti-cancer activity. It suggests that the curcumin-containing lipid nanoparticle complex provided in the present invention may be used as an anti-cancer drug with excellent anti-cancer activity.
- the pharmaceutical composition of the present invention may be prepared in the form of a pharmaceutical composition for treating cancer further comprising conventionally used appropriate carriers, excipients, or diluents.
- the carrier used in this case may be an unnatural carrier.
- the pharmaceutical composition may be used by being formulated as, according to each conventional method respectively, powders, granules, capsules, suspensions, emulsions, syrups, aerosols, oral formulations such as oral patches, external compositions, external patches, suppositories, and sterile injection solutions.
- the content of the curcumin-containing lipid nanoparticle complex contained in the pharmaceutical composition of the prevent invention may be in a range of 0.0001 wt % to 50 wt %, preferably in a range of 0.01 wt % to 20 wt %, but is not particularly limited thereto, and the concentration of the curcumin-containing lipid nanoparticle complex contained in a single dose of the pharmaceutical composition may be in a range of 2.5 mM to 25 mM.
- subject of the present invention may include, without limitation, rats, cattle, mammals including humans, farmed fishes, etc. that have the risk of cancer development or have cancer.
- the types of cancer to be treated are the same as described above.
- composition may be administered in a pharmaceutically effective amount in a single or multiple administrations.
- the composition may be formulated as solutions, powders, aerosols, injections, infusion solutions (intravenous), capsules, pills, tablets, suppositories, or patches to be administered.
- the route of administration of the pharmaceutical composition of the present invention for treating cancer may include any general routes.
- the dosage of the pharmaceutical composition of the present invention may be decided by those skilled in the art based on the intended use, the addictivity of the disease, the patient’s age, weight, gender, medical history, or the type of substances used as active ingredients.
- the pharmaceutical composition of the present invention may be administered at a dose in a range of about 0.1 ng/kg to 100 mg/kg, specifically in a range of about 1 ng/kg to 10 mg/kg per adult, and the frequency of the administration of the present invention may be administered once daily or many times in multiple portions, but is not particularly limited thereto.
- the above dosages do not limit the scope of the invention whatsoever.
- the present invention provides a food composition for preventing or ameliorating cancer comprising the curcumin-containing lipid nanoparticle complex.
- Curcumin is contained in a high amount in turmeric (curcuma aromatica or curcuma longa L) and has long been used as food, and the curcumin-containing lipid nanoparticle complex, which contains the curcumin, may be included in a food composition to take advantage of the anti-cancer activity of curcumin.
- the content of the curcumin-containing lipid nanoparticle complex contained in the composition may be in a range of 0.001 wt % to 10 wt %, preferably in a range of 0.1 wt % to 1 wt %, based on the total weight of the composition, but is not particularly limited thereto.
- the composition When the composition is in a liquid form, it may be comprised in a ratio of 1 g to 10 g per 100 mL, preferably, in a ratio of 2 g to 7 g per 100 mL.
- functional food exhibiting anti-cancer activity may be prepared by using the food composition comprising the curcumin-containing lipid nanoparticle complex.
- the food composition may be used to prepare processed food exhibiting anti-cancer activity, and it may be prepared in the form of snacks, beverages, alcoholic beverages, fermented food, canned food, dairy products, processed meat or noodle-processed food, etc., as functional food.
- snacks may include biscuits, pies, cakes, bread, candies, gum, cereal (meal substitutes such as grain cereal), etc.
- Beverages may include drinking water, carbonated beverages, functional ion drinks, juice (for example, apple, pear, grape, aloe, tangerine, peach, carrot, tomato juice, etc.), sweet rice drinks (sikhye), etc.
- Alcoholic beverages may include sake, whiskey, soju, beer, liquor, fruit wine, etc.
- the term "functional food” is the same term as food for special health use (FoSHU), and in addition to nutritional supply, the term means food processed to have a high medical and medicinal effect by exhibiting physiological functions efficiently, and the food may be prepared in various forms such as tablets, capsules, powders, granules, liquid, pills, etc. to achieve beneficial effects for preventing or ameliorating cancer.
- the present invention provides an anti-oxidant composition comprising the curcumin-containing lipid nanoparticle complex.
- curcumin is known to exhibit a high level of anti-oxidant activity
- the curcumin-containing lipid nanoparticle complex of the present invention in which the curcumin is encapsulated, can improve the anti-oxidant activity of curcumin itself.
- Example 1-1 Preparation of ginsenosides by fermentation of ginseng saponin powder
- the yield of the ginsenosides preparation by fermentation was 55.4%.
- small amount of the sample was solubilized by methanol and filtered by using syringe filter (0.45 ⁇ m).
- An aliquot of the methanol solution (20 ⁇ l) was injected into HPLC and analyzed for the composition of ginsenosides.
- the column used was C18 Inertsil (4.6 ⁇ 250 mm, 5 ⁇ m) and detector was used by ultraviolet absorption at 203 nm. Gradient condition is as summarized in Table 1.
- the dried sediment contained ginsenosides Rg1, Rg3, F1, F2, compound K, which does not exist or minimally exists in the ginseng saponin powder, as much as 6.49%, 3.31%, 3.85%, 9.66%, and 2.55%, respectively.
- Example 1-2 Preparation of ginsenosides by acid hydrolysis of ginseng saponin powder
- FIG. 1 is an electron transmission microscope photograph illustrating the form of the curcumin-containing lipid nanoparticle complex of the present invention dispersed in water, wherein A is a photograph taken at low magnification, and B is a photograph taken at a high magnification. As shown in FIG. 1, it was confirmed that when the lipid nanoparticle was dispersed in water, a lipid nanoparticle whose core/shell structure was smaller than 1 micron was formed.
- Example 2-2 Evaluation of the stability of the curcumin -containing lipid nanoparticle
- the curcumin-containing lipid nanoparticle complex was dispersed in a phosphate buffer solution (PBS, pH 8.0) to a concentration of 100 ng/ml, and the concentration of the remaining undegraded curcumin was measured by HPLC (FIG. 2) while stirring with a magnetic stirrer at 37°C for 6 hours.
- PBS phosphate buffer solution
- a control group a methanol solution of curcumin was used, and for the HPLC process condition, C18 Inertsil ODS (150 mm ⁇ 4.6 mm, 5 ⁇ m) was used, and as a mobile phase, a mixture solution of acetonitrile and 2% acetic acid (65:35% v/v) was used, the flow rate was set to 0.8 ml/min, and an ultraviolet absorbance meter (425 nm) was used as a detector.
- C18 Inertsil ODS 150 mm ⁇ 4.6 mm, 5 ⁇ m
- a mobile phase a mixture solution of acetonitrile and 2% acetic acid (65:35% v/v) was used, the flow rate was set to 0.8 ml/min, and an ultraviolet absorbance meter (425 nm) was used as a detector.
- Example 2-3 Evaluation of the dispersibility of the curcumin -containing lipid nanoparticle complex
- Curcumin-containing molecular complexes prepared by the prior art are waxy products and therefore are not dispersed in water, and after applying shearing stress by ultrasonic wave to form a dispersed solution, it is known that the curcumin molecule leaves the molecular complex to be educed as rectangular crystals (FIG. 3).
- FIG. 3 is a photograph illustrating the phenomenon of curcumin being educed when the molecular complex prepared by the prior art is dispersed in water.
- the curcumin-containing lipid nanoparticle complex prepared in Example 2-1 was dispersed in water, and immediately after dispersal thereof, the condition was evaluated after the passage of 1 week and the passage of 2 weeks (FIG. 4).
- FIG. 4 is a photograph illustrating the results of evaluating the dispersibility of the curcumin-containing lipid nanoparticle complex of the present invention (the composition in Example 2-1), wherein A is a photograph illustrating the condition of the dispersed solution after 1 week, and B is a photograph illustrating the condition of the dispersed solution after 2 weeks.
- A is a photograph illustrating the condition of the dispersed solution after 1 week
- B is a photograph illustrating the condition of the dispersed solution after 2 weeks.
- Example 3-1 Preparation of the curcumin -containing lipid nanoparticle complex comprising hardened soybean oil
- an improved curcumin-containing lipid nanoparticle complex was prepared by adding hardened soybean oil as triglycerides.
- curcumin, a phospholipid, an enzyme-digested phospholipid, a caprylic/capric triglyceride, ginsenosides, and hardened soybean oil were mixed in a weight ratio of 3.85%, 38.46%, 7.69%, 38.46%, 3.85%, and 7.69%, respectively, and an improved curcumin-containing lipid nanoparticle complex was prepared by dissolving the obtained mixture in ethanol and removing the ethanol by concentrating under reduced pressure.
- FIG. 5 is a photograph (A) illustrating the form of the improved curcumin-containing lipid nanoparticle complex(the composition in Example 3-1) of the present invention, after the passage of 2 weeks after dispersal thereof in water, and is a graph (B) illustrating the result of measuring the size of the curcumin-containing lipid nanoparticle complex which was formed after dispersal thereof in water.
- FIG. 5 when the improved curcumin-containing lipid nanoparticle complex provided in the present invention was dispersed in water, it was confirmed that the complex was uniformly dispersed in water exhibiting a constant size.
- Example 3-2 Solubility analysis of the curcumin -containing lipid nanoparticle complex comprising hardened soybean oil
- the improved lipid nanoparticle was added to 100 ml of distilled water, was stirred with a magnetic stirrer for 6 hours, and after filtering the solution with a 0.2 ⁇ m syringe filter, the concentration of curcumin was measured by HPLC in the filtrate (Table 2). In particular, pure curcumin was used as a control group.
- the curcumin-containing lipid nanoparticle complex of the present invention (the composition in Example 3-1) was confirmed to have approximately 4600-fold improved solubility, as compared to the solubility of pure curcumin.
- Example 3-3 Analysis of the elution rate of the curcumin -containing lipid nanoparticle comprising hardened soybean oil
- the improved curcumin-containing lipid nanoparticle complex which was prepared in Example 3-1, was added to 100 ml of artificial serum, and the elution amount of curcumin was measured over the course of 6 hours (FIG. 6).
- pure curcumin was used as a control group.
- FIG. 6 is a graph illustrating the results of evaluating the elution rate of the improved curcumin-containing lipid nanoparticle complex(the composition in Example 3-1) provided in the present invention. As shown in FIG. 6, in the control group, less than 15% was eluted in the simulated intestinal fluid, but the improved curcumin-containing lipid nanoparticle complex provided in the present invention (the composition in Example 3-1) was nearly 100% eluted within one hour.
- Example 3-4 Bioavailability analysis of the curcumin -containing lipid nanoparticle complex comprising hardened soybean oil
- a sample prepared by dispersing the improved curcumin-containing lipid nanoparticle complex prepared in Example 3-1 in distilled water was orally administered to Sprague-Dawley rats (7-week-old, 6 mice in each group) at a dose of 50 mg/kg or 100 mg/kg, blood samples were collected by exsanguination every 8 hours, and the blood concentrations of pure curcumin contained in each blood sample were measured by LC-MS (FIG. 7).
- the blood concentrations of curcumin were used by orally administering pure curcumin at a dose of 100 mg/kg.
- the blood concentrations of curcumin were implemented by Agilent 6490 Triple Quadrupole LC/MS system, the column was Zorbax Extend C18 (150 mm ⁇ 1.0 mm, 3.5 ⁇ m), the mobile phase was a mixture solution (50:50, %(v/v)) of acetonitrile containing 0.1% formic acid and distilled water containing 0.1% formic acid, the injection solution was 4 ⁇ l, the column temperature was 28°C, and the flow rate was 0.1 ml/min.
- the internal standard material was hesperetin.
- FIG. 7 is a graph illustrating the result of comparing the blood concentration changes of curcumin over time after the improved curcumin-containing lipid nanoparticle complex provided in the present invention (the composition in Example 3-1) was orally administered at different doses over time.
- the control group when pure curcumin was orally administered (the control group), curcumin was not detected at all in the blood, but when the improved curcumin-containing lipid nanoparticle provided in the present invention was orally administered, the time to reach the maximum blood concentration of curcumin was 30 minutes, and the blood concentration was confirmed to increase in a dose-dependent manner.
- the enterohepatic circulation phenomenon was confirmed, in which the blood concentration of curcumin was not large, but rose again.
- curcumin-containing lipid nanoparticle complex was also capable of improving the bioavailability of curcumin.
- the bioavailability of the improved curcumin-containing lipid nanoparticle complex provided in the present invention was significantly increased, as compared to the bioavailability of the molecular complex provided in the prior art.
- the bioavailability per dosage unit bioavailability
- the bioavailability of the improved curcumin-containing lipid nanoparticle complex provided in the present invention was increased by about 8 to 9 times the bioavailability of the molecular complex provided in the prior art.
- Example 4 Analysis of the anti-cancer activity of the curcumin -containing lipid nanoparticle complex
- curcumin has been used as an active ingredient for anti-cancer therapy, in order to confirm that the curcumin-containing lipid nanoparticle of the present invention showed a more enhanced anti-cancer activity, the anti-cancer activity of the lipid nanoparticle of the present invention against colorectal cancer, lung cancer, breast cancer, or melanoma cells was evaluated.
- Example 4-1 Anti-cancer activity against colorectal cancer cells
- HCT 116 cells which are colorectal cancer cells, were cultured in a RPMI1640 medium containing 10% FBS and 1% penicillin/streptomycin.
- the cultured HCT 116 cells were dispensed into a 96-well plate so that 5000 cells were placed in a well and were cultured at 37°C for 24 hours, a lipid nanoparticle without encapsulated curcumin (control drug 1), curcumin dissolved in DMSO (control drug 2) or the curcumin-containing lipid nanoparticle complex (test drug) that was prepared in Example 3-1 were treated, and the cultured HCT 116 cells were cultured for 48 hours.
- the amount of the test drug and control drug 2 was set to be such that the concentration of curcumin was 1, 5, 10, or 20 ⁇ g/ml, and in the case of control drug 1, the same amount as that of the test drug was tailored for each concentration.
- FIG. 8a is a graph illustrating the results of analyzing the anti-cancer activity of the curcumin-containing lipid nanoparticle complex(the composition of Example 3-1) of the present invention against colorectal cancer cells.
- the lipid nanoparticle without encapsulated curcumin did not exhibit anti-cancer activity against HCT 116 cells, but it was confirmed that the viability of the HCT 116 cells treated with control drug 2 containing curcumin and the test drug was decreased, as the treatment amount of curcumin was increased. Also, when treated with the test drug, it was confirmed that the viability of the HCT 116 cells was further decreased, as compared to the control drug 2 treatment.
- curcumin-containing lipid nanoparticle complex of the present invention exhibited better anti-cancer activity against colorectal cancer than simply treating with curcumin.
- Example 4-2 Anti-cancer activity against lung cancer cells
- Example 4-1 As an object to evaluate the anti-cancer activity, except for the fact that A549 cells, which are lung cancer cells, were used instead of HCT 116 cells, which are colorectal cancer cells, the same method as in Example 4-1 was performed, and the effects of the curcumin-containing lipid nanoparticle complex on the viability of A549 cells were compared (FIG. 8b).
- FIG. 8b is a graph illustrating the results of analyzing the anti-cancer activity against lung cancer cells exhibited by the curcumin-containing lipid nanoparticle complex(the composition of Example 3-1). As shown in FIG. 8b, the lipid nanoparticle that did not contain curcumin did not show anti-cancer activity against A549 cells, but it was confirmed that the viability of the A549 cells treated with control drug 2 containing curcumin and the test drug was decreased as the treatment amount of curcumin was increased. Also, it was confirmed that the viability of the A549 cells was further decreased when the cells were treated with the test drug, as compared to control drug 2.
- curcumin-containing lipid nanoparticle complex of the present invention exhibited better anti-cancer activity against lung cancer than simply treating with curcumin.
- Example 4-1 As an object to evaluate the anti-cancer activity, except for the fact that MCF7 cells, which are breast cancer cells, were used instead of HCT 116 cells, which are colorectal cancer cells, the same method as in Example 4-1 was performed, and the effects of the curcumin-containing lipid nanoparticle complex on the viability of A549 cells were compared (FIG. 8c).
- FIG. 8c is a graph illustrating the results of analyzing the anti-cancer activity against breast cancer cells exhibited by the curcumin-containing lipid nanoparticle complex(the composition of Example 3-1). As shown in FIG. 8c, the lipid nanoparticle that did not contain curcumin did not show anti-cancer activity against MCF7 cells, but it was confirmed that the viability of the MCF7 cells treated with control drug 2 containing curcumin and the test drug was decreased as the treatment amount of curcumin was increased. Also, it was confirmed that the viability of the MCF7 cells was further decreased when the cells were treated with the test drug, as compared to control drug 2.
- Example 4-4 Anti-cancer activity against melanoma cells
- Example 4-1 As an object to evaluate the anti-cancer activity, except for the fact that SKEML-02 cells, which are melanoma cells, were used instead of HCT 116 cells, which are colorectal cancer cells, the same method as in Example 4-1 was performed, and the effects of the curcumin-containing lipid nanoparticle complex on the viability of SKEML-02 cells were compared (FIG. 8d).
- curcumin-containing lipid nanoparticle complex of the present invention exhibited better anti-cancer activity against melanoma than simply treating with curcumin.
- curcumin exhibits anti-cancer activity against various kinds of cancer, and rather than simply treating with curcumin only, it was found that more improved anti-cancer activity was exhibited when treated in the form of the curcumin-containing lipid nanoparticle complex provided in the present invention.
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Abstract
Pour améliorer la stabilité, la dispersibilité et la biodisponibilité de la curcumine, la présente invention concerne une nanoparticule lipidique comprenant des ginsénosides et des phospholipides ; un procédé de préparation de la nanoparticule lipidique ; une composition pharmaceutique pour prévenir ou traiter le cancer comprenant la nanoparticule lipidique ; une composition alimentaire antioxydante, une composition alimentaire pour animaux et une composition cosmétique. Étant donné que la nanoparticule lipidique contenant de la curcumine constituant l'objet de la présente invention améliore la stabilité, la dispersibilité et la biodisponibilité du fait de l'utilisation de ginsénosides, la nanoparticule lipidique contenant de la curcumine peut être largement utilisée dans le développement de divers produits contenant de la curcumine.
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WO2020214125A1 (fr) * | 2019-04-16 | 2020-10-22 | Istanbul Medipol Universitesi | Émulsion lipidique solide comprenant de la curcumine et de la pipérine et son utilisation |
CN111973557A (zh) * | 2018-11-29 | 2020-11-24 | 上海参素药物技术有限公司 | 一种多西他赛脂质体、其制备方法及应用 |
WO2021176327A1 (fr) * | 2020-03-02 | 2021-09-10 | Yogesh Dound | Compositions liposomales de curcumine et leur procédé de préparation |
CN113786369A (zh) * | 2021-11-05 | 2021-12-14 | 青岛科技大学 | 一种含人参总皂苷的天然抗氧化纳米组合物及其制备方法 |
WO2022037814A1 (fr) * | 2020-08-19 | 2022-02-24 | Henkel Ag & Co. Kgaa | Teintures pour fibres de kératine comprenant des colorants naturels encapsulés |
CN114831935A (zh) * | 2022-05-18 | 2022-08-02 | 沈阳信康药物研究有限公司 | 一种可鼻饲给药的无菌20(s)-ppd口服液体制剂及其制备方法和应用 |
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KR101996713B1 (ko) * | 2017-01-18 | 2019-07-04 | 가천대학교 산학협력단 | 진세노사이드 및 인지질 기반 지질나노입자 및 이의 제조방법 |
KR101975295B1 (ko) * | 2018-03-15 | 2019-05-07 | 서울대학교 산학협력단 | 20(S)-protopanaxadiol(PPD)의 피부흡수 개선을 위한 나노입자 조성물 및 제조방법 |
KR102613550B1 (ko) * | 2018-05-17 | 2023-12-14 | 한국생명공학연구원 | 난용성 물질인 커큐민을 포함하는 진세노사이드 복합체 |
KR102291017B1 (ko) * | 2019-08-26 | 2021-08-20 | 주식회사 앱스바이오 | 감초추출물을 포함하는 지질나노입자 복합체 및 그의 제조방법 |
KR102169710B1 (ko) * | 2020-01-08 | 2020-10-26 | 제주대학교 산학협력단 | 커큐민 나노스피어, 그 제조방법 및 이의 용도 |
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WO2021176327A1 (fr) * | 2020-03-02 | 2021-09-10 | Yogesh Dound | Compositions liposomales de curcumine et leur procédé de préparation |
WO2022037814A1 (fr) * | 2020-08-19 | 2022-02-24 | Henkel Ag & Co. Kgaa | Teintures pour fibres de kératine comprenant des colorants naturels encapsulés |
CN113786369A (zh) * | 2021-11-05 | 2021-12-14 | 青岛科技大学 | 一种含人参总皂苷的天然抗氧化纳米组合物及其制备方法 |
CN114831935A (zh) * | 2022-05-18 | 2022-08-02 | 沈阳信康药物研究有限公司 | 一种可鼻饲给药的无菌20(s)-ppd口服液体制剂及其制备方法和应用 |
CN114831935B (zh) * | 2022-05-18 | 2023-04-07 | 沈阳信康药物研究有限公司 | 一种可鼻饲给药的无菌20(s)-ppd口服液体制剂及其制备方法和应用 |
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