CN111973621A - Compound containing chitosan oligosaccharide and application - Google Patents
Compound containing chitosan oligosaccharide and application Download PDFInfo
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- CN111973621A CN111973621A CN202010777934.1A CN202010777934A CN111973621A CN 111973621 A CN111973621 A CN 111973621A CN 202010777934 A CN202010777934 A CN 202010777934A CN 111973621 A CN111973621 A CN 111973621A
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- chitosan oligosaccharide
- piperine
- compound
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- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 title claims abstract description 92
- 150000001875 compounds Chemical class 0.000 title claims abstract description 40
- 229940075559 piperine Drugs 0.000 claims abstract description 68
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 claims abstract description 68
- 235000019100 piperine Nutrition 0.000 claims abstract description 68
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 claims abstract description 50
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 13
- 201000007270 liver cancer Diseases 0.000 claims abstract description 13
- 208000014018 liver neoplasm Diseases 0.000 claims abstract description 13
- 201000005202 lung cancer Diseases 0.000 claims abstract description 13
- 208000020816 lung neoplasm Diseases 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000003560 cancer drug Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 241000758706 Piperaceae Species 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000006072 paste Substances 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 12
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- 235000013376 functional food Nutrition 0.000 abstract description 4
- 210000004185 liver Anatomy 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- 230000036737 immune function Effects 0.000 abstract description 3
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 235000013373 food additive Nutrition 0.000 abstract 1
- 239000002778 food additive Substances 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 34
- -1 piperine compound Chemical class 0.000 description 18
- 230000002401 inhibitory effect Effects 0.000 description 9
- 210000002540 macrophage Anatomy 0.000 description 9
- 238000005303 weighing Methods 0.000 description 7
- 210000001744 T-lymphocyte Anatomy 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 4
- 238000012258 culturing Methods 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 102000004142 Trypsin Human genes 0.000 description 3
- 108090000631 Trypsin Proteins 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 230000036039 immunity Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000012588 trypsin Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
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- 238000004113 cell culture Methods 0.000 description 2
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- 238000013329 compounding Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 208000006313 Delayed Hypersensitivity Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 1
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002434 immunopotentiative effect Effects 0.000 description 1
- 230000007365 immunoregulation Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000004199 lung function Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7016—Disaccharides, e.g. lactose, lactulose
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to the industries of functional food and medicine, in particular to a compound containing chitosan oligosaccharide and application thereof. The compound is chitosan oligosaccharide and piperine in a mass ratio of 1:9-9: 1. The invention combines the functions of enhancing the immune function, improving the liver and the heart-lung functions and the like of chitosan oligosaccharide and the anti-tumor effect of piperine, has certain synergistic inhibition effect on liver cancer cells and lung cancer cells, and is a functional food compound which is beneficial to enhancing the immune function, resisting tumors and the like. Both the chitosan oligosaccharide and the piperine can be used as food or food additives, are easy to popularize and can be widely applied to the fields of functional foods and medicines.
Description
Technical Field
The invention relates to the industries of functional food and medicine, in particular to a compound containing chitosan oligosaccharide and application thereof.
Background
Chitosan oligosaccharide is also called Chitosan Oligosaccharide (COS), is an oligosaccharide formed by connecting 2-10 glucosamine with beta-1, 4 glycosidic bonds, and is usually obtained by deacetylating chitin contained in aquatic product wastes such as shrimp and crab shells and degrading by glycosidase. The chitosan oligosaccharide is the only basic amino-polysaccharide existing in a large amount in natural sugar, has the characteristics of good water solubility, safety, no toxicity, easy absorption, good biocompatibility and the like, and shows various biological activities: enhancing immunity of organism tissue and organ, inhibiting growth and proliferation of tumor cells, protecting liver injury, improving liver and heart and lung functions, regulating blood sugar and blood lipid, increasing beneficial bacteria in intestinal tract, etc. The immunopotentiation effect of chitosan oligosaccharide is proved by a plurality of scholars at present, the chitosan oligosaccharide can stimulate the body, promote the increase of the cell number of peritoneal exudate and activate macrophages, so that the generation of active oxygen is increased, and then the peroxidation sterilization mechanism plays a role. The direct activation of the chitosan oligosaccharide to the macrophage increases the killing activity of the macrophage; the chitosan oligosaccharide activates T lymphocytes to show killing activity, and the sensitized T cells induce delayed hypersensitivity; chitosan oligosaccharide activates T lymphocytes, thereby promoting the release of Macrophage Activating Factor (MAF), which in turn activates macrophages. During the activation process, the macrophage is directly activated by the chitosan oligosaccharide, and the sensitivity of the macrophage to MAF can be improved, so that the macrophage is further activated. It is therefore believed that the killing activity of chitosan oligosaccharide occurs primarily as a result of the enhanced interaction of activated T lymphocytes with macrophages.
However, the biological activity of the chitosan oligosaccharide is weak, and although the chitosan oligosaccharide has a certain immunoregulation effect and a tumor cell growth and proliferation inhibiting effect, the effect of the chitosan oligosaccharide used alone is not obvious, so that some effective active factors need to be compounded to enhance the activity effect through interaction. At the present stage, the research on the compound containing the chitosan oligosaccharide is not many, most of active compounds cannot effectively interact with the chitosan oligosaccharide, so that active molecules which easily interact with chitosan oligosaccharide molecules need to be searched, the advantages of the chitosan oligosaccharide and the chitosan oligosaccharide are better played, the activities are complementary, and unexpected effects can be possibly achieved.
Disclosure of Invention
The invention aims to provide a preparation method and application of a compound of chitosan oligosaccharide and piperine, which is helpful for enhancing immune function and improving liver and heart-lung functions and has a synergistic effect on anticancer activity.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a compound containing chitosan oligosaccharide is prepared from chitosan oligosaccharide and piperine according to the mass ratio of 1:9-9: 1.
The molecular weight of the chitosan oligosaccharide is 500-8000; the piperine is extracted from Piperaceae plants.
The compound is chitosan oligosaccharide and piperine in a mass ratio of 3:7-4: 6.
The compound is chitosan oligosaccharide and piperine in a mass ratio of 4:6-5: 5.
The application of the compound in preparing anticancer medicine.
The application of the compound in preparing anti-liver cancer or anti-lung cancer drugs.
The compound is an application of chitosan oligosaccharide and piperine in the preparation of anti-liver cancer drugs according to the mass ratio of 3:7-4: 6.
The compound is an application of chitosan oligosaccharide and piperine in the preparation of the anti-lung cancer medicine according to the mass ratio of 4:6-5: 5.
A compound preparation containing chitosan oligosaccharide, wherein the compound is used as an active ingredient and is mixed with an acceptable carrier; wherein the active ingredient accounts for 0.1-99% of the weight of the preparation.
The preparation can be capsule, tablet, powder, granule, suspension, emulsion or paste.
The invention has the advantages that:
(1) the compound obtained by the invention combines chitosan oligosaccharide with the functions of enhancing immunity and improving liver and heart and lung and piperine with the function of inhibiting tumor cell proliferation, can prevent canceration by enhancing immunity, can treat early liver cancer and lung cancer, and is more beneficial to preventing and treating related diseases of consumer groups;
(2) the chitosan oligosaccharide and the piperine both have certain anticancer activity and are beneficial to preventing the occurrence or recurrence of tumor cells, and the compound product of the chitosan oligosaccharide and the piperine has a synergistic effect, when the compound ratio of the chitosan oligosaccharide to the piperine is 3:7-4:6, the compound product has the highest inhibition rate on liver cancer cells HepG2, and when the mass ratio of the chitosan oligosaccharide to the piperine is 4:6-5:5, the compound product has the highest inhibition rate on lung cancer cells A549.
Detailed Description
The following examples are further illustrative of the present invention, but the present invention is not limited to the compositions and uses of the present embodiments.
The molecular weight of the chitosan oligosaccharide used in the following examples is 500-; the piperine can be obtained by extracting Piperaceae plant according to conventional technique, or obtained commercially.
Example 1:
weighing 1.0g of chitosan oligosaccharide and 9.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Example 2:
the difference from the embodiment 1 is that:
weighing 2.0g of chitosan oligosaccharide and 8.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Example 3:
the difference from the embodiment 1 is that:
3.0g of chitosan oligosaccharide and 7.0g of piperine are weighed and mixed evenly to obtain the chitosan oligosaccharide and piperine compound.
Example 4:
the difference from the embodiment 1 is that:
weighing 4.0g of chitosan oligosaccharide and 6.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Example 5:
the difference from the embodiment 1 is that:
5.0g of chitosan oligosaccharide and 5.0g of piperine are weighed and mixed evenly to obtain the chitosan oligosaccharide and piperine compound.
Example 6:
the difference from the embodiment 1 is that:
weighing 6.0g of chitosan oligosaccharide and 4.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Example 7:
the difference from the embodiment 1 is that:
weighing 7.0g of chitosan oligosaccharide and 3.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Example 8:
the difference from the embodiment 1 is that:
weighing 8.0g of chitosan oligosaccharide and 2.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Example 9:
the difference from the embodiment 1 is that:
weighing 9.0g of chitosan oligosaccharide and 1.0g of piperine, and uniformly mixing to obtain the chitosan oligosaccharide and piperine compound.
Application example
Cell culture: complete medium was prepared by adding 10% final concentration fetal bovine serum, 100U/mL penicillin and 100. mu.g/mL streptomycin to DMEM medium. Taking out the liver cancer cell HepG2 and the lung cancer cell A549 cryopreserved tubes from liquid nitrogen, immediately placing the tubes in a water bath at 37 ℃, quickly and gently shaking the tubes, unfreezing the cells, centrifuging the cells at 1000rpm for 10min, and discarding the supernatant. Separately suspending the two cells using fresh complete medium, transferring the suspensions to a cell culture flask at 37℃、5％CO2And culturing the cells in an incubator with saturated humidity. And (4) observing the growth condition of the cells at any time, and carrying out cell liquid change after the cells are fully attached to the wall, wherein the cells are passaged for 2-3 times every week. When the cells are subcultured, washing the cells for 2-3 times by using PBS buffer solution, then digesting by using 0.25% trypsin, quickly and carefully pouring out the trypsin solution, adding culture medium to terminate digestion, re-suspending the cells, discarding a part of cell suspension according to the number of the cells, and supplementing a proper amount of fresh culture medium to continue culturing.
The MTT method is used for detecting the chitosan oligosaccharide, the piperine and the compound of the chitosan oligosaccharide and the piperine obtained in the embodiment for inhibiting the proliferation of the liver cancer cell HepG2 and the lung cancer cell A549: taking cancer cells in logarithmic growth phase, digesting with trypsin to obtain cell suspension, and adjusting cell concentration to 1 × 105Perml, cells were seeded in 96-well plates at 100. mu.L/well in 37 ℃ with 5% CO2Culturing for 24 hours in an incubator with saturated humidity; after the cells adhere to the wall, the complete culture medium containing the samples is replaced, 5 duplicate wells are set for each sample, and the zero setting wells and the control wells are set at the same time. Cells at 37 ℃ and 5% CO2Culturing for 48h in an incubator with saturated humidity; the cell culture medium was decanted, 100. mu.L of fresh medium, 10. mu.L of MTT was added to each well, incubated at 37 ℃ for 4h, centrifuged at 1000rpm for 5min, the medium was discarded, 150. mu.L of dimethyl sulfoxide was added to each well, and shaken for 15 min. The absorbance was measured at 490nm with a microplate reader.
Cell growth inhibition (%) ═ aControl–ASample (I))/AControl×100
The anticancer activity test of chitosan oligosaccharide, piperine and the compound of chitosan oligosaccharide and piperine has the following results:
TABLE 1 inhibitory Activity of liver cancer cell HepG2 (%)
TABLE 2 inhibitory Activity of Lung cancer cell A549 (%)
| 0.05mg/mL | 0.10mg/mL | 0.25mg/mL | |
| Chitosan oligosaccharide | 1.62 | 6.04 | 11.21 |
| Piperine | 12.56 | 30.57 | 50.48 |
| Chitosan oligosaccharide piperine compound (1:9) | 13.44 | 33.14 | 55.94 |
| Chitosan oligosaccharide piperine compound (2:8) | 14.57 | 33.78 | 56.47 |
| Chitosan oligosaccharide piperine compound (3:7) | 18.74 | 34.99 | 57.24 |
| Chitosan oligosaccharide piperine compound (4:6) | 22.17 | 40.14 | 60.14 |
| Chitosan oligosaccharide piperine compound (5:5) | 20.67 | 36.54 | 58.08 |
| Chitosan oligosaccharide piperine compound (6:4) | 15.64 | 30.28 | 51.48 |
| Chitosan oligosaccharide piperine compound (7:3) | 8.97 | 21.47 | 40.57 |
| Chitosan oligosaccharide piperine compound (8:2) | 6.47 | 15.78 | 28.74 |
| Chitosan oligosaccharide piperine compound (9:1) | 3.75 | 10.67 | 15.24 |
Tables 1 and 2 show the inhibitory activity of chitosan oligosaccharide, piperine and the compound of chitosan oligosaccharide and piperine on liver cancer cells HepG2 and lung cancer cells A549, and it can be seen from the tables that the inhibitory activity of chitosan oligosaccharide on two kinds of cancer cells is very low, and the inhibitory activity of piperine is relatively strong. When the chitosan oligosaccharide and the piperine are compounded, the inhibition rate is higher along with the increase of the concentration, and the inhibition activity on cancer cells is enhanced under the same concentration, which is slightly stronger than that of the chitosan oligosaccharide and the piperine which are used separately. This may be related to Schiff's base and hydrogen bond interactions between the amino and hydroxyl groups of chitosan oligosaccharide and the carbonyl and trans-butadiene structures in piperine molecule. The inhibition rate of the compound is related to the compounding ratio of chitosan oligosaccharide/piperine, and the inhibition rate is increased and then reduced along with the increase of the ratio of chitosan oligosaccharide. When the compound ratio of the chitosan oligosaccharide and the piperine is 3:7-4:6, the inhibition rate on liver cancer cells HepG2 is relatively highest, and when the mass ratio of the chitosan oligosaccharide to the piperine is 4:6-5:5, the inhibition rate on lung cancer cells A549 is relatively highest. However, as the ratio of chitosan oligosaccharide is further increased, the inhibition ratio of the complex becomes weaker. If, for example, when the compounding ratio of the chitosan oligosaccharide and the piperine is 5:5 in terms of component content, at a concentration of 0.10mg/mL, the effective concentration of the chitosan oligosaccharide and the piperine is actually 0.05mg/mL, and the inhibition rate after the two compounds are compounded is much stronger than that of the monomer without the compound in terms of the inhibition activity on two tumor cells.
The chitosan oligosaccharide and the piperine are both food-grade, and the compound of the chitosan oligosaccharide and the piperine has respective biological activities and has synergistic effect on liver cancer cells and lung cancer cells, so that the effect of mixing the chitosan oligosaccharide and the piperine according to a specific ratio is obvious and is not expected to be obtained, and the prevention of cancers is facilitated.
Meanwhile, the compound prepared by the above embodiment is mixed with acceptable medicinal or food-grade carriers as an active ingredient according to the records of the existing preparation formulation documents, wherein the active ingredient accounts for 0.1-99% of the weight of the preparation; can be made into capsule, tablet, powder or granule, which also has the above effects.
Claims (10)
1. A chitosan oligosaccharide-containing complex characterized by: the compound is chitosan oligosaccharide and piperine in a mass ratio of 1:9-9: 1.
2. The chitosan oligosaccharide-containing complex of claim 1, wherein:
the molecular weight of the chitosan oligosaccharide is 500-8000; the piperine is extracted from Piperaceae plants.
3. The chitosan oligosaccharide-containing complex of claim 1 or 2, wherein: the compound is chitosan oligosaccharide and piperine in a mass ratio of 3:7-4: 6.
4. The chitosan oligosaccharide-containing complex of claim 1 or 2, wherein: the compound is chitosan oligosaccharide and piperine in a mass ratio of 4:6-5: 5.
5. Use of a compound according to claim 1, wherein: the application of the compound in preparing anti-cancer drugs.
6. Use according to claim 5, characterized in that: the application of the compound in preparing anti-liver cancer or anti-lung cancer drugs.
7. Use according to claim 6, characterized in that: the compound is an application of chitosan oligosaccharide and piperine in the preparation of anti-liver cancer drugs according to the mass ratio of 3:7-4: 6.
8. Use according to claim 6, characterized in that: the compound is an application of chitosan oligosaccharide and piperine in the preparation of the anti-lung cancer medicine according to the mass ratio of 4:6-5: 5.
9. The chitosan oligosaccharide-containing complex formulation of claim 1, wherein: mixing the complex as an active ingredient with an acceptable carrier; wherein the active ingredient accounts for 0.1-99% of the weight of the preparation.
10. The chitosan oligosaccharide-containing complex formulation of claim 9, wherein: the preparation can be capsule, tablet, powder, granule, suspension, emulsion or paste.
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Non-Patent Citations (3)
| Title |
|---|
| PRASHANT SAHU等: "Enhanced Hepatoprotective activity of Piperine Loaded Chitosan Microspheres", 《INTERNATIONAL JOURNAL OF DRUG DEVELOPMENT & RESEARCH》 * |
| 周艳芬等: "壳寡糖对Hela细胞和A549细胞自噬性死亡的影响", 《科学技术与工程》 * |
| 陈帅等: "胡椒碱的纳米传递载体研究进展", 《中国调味品》 * |
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