CN115212196A - New application of aeginetia indica polyene compounds - Google Patents
New application of aeginetia indica polyene compounds Download PDFInfo
- Publication number
- CN115212196A CN115212196A CN202210987194.3A CN202210987194A CN115212196A CN 115212196 A CN115212196 A CN 115212196A CN 202210987194 A CN202210987194 A CN 202210987194A CN 115212196 A CN115212196 A CN 115212196A
- Authority
- CN
- China
- Prior art keywords
- polyene
- aeginetia
- indica
- aeginetia indica
- polyene compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 235000014624 Aeginetia indica Nutrition 0.000 title claims abstract description 60
- 244000015329 Aeginetia indica Species 0.000 title claims abstract description 55
- -1 polyene compounds Chemical class 0.000 title claims abstract description 41
- 241001530126 Scrophularia Species 0.000 claims abstract description 22
- 150000004291 polyenes Chemical class 0.000 claims abstract description 21
- 239000003814 drug Substances 0.000 claims abstract description 16
- JPIJQSOTBSSVTP-PWNYCUMCSA-N D-erythronic acid Chemical compound OC[C@@H](O)[C@@H](O)C(O)=O JPIJQSOTBSSVTP-PWNYCUMCSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 12
- 208000019423 liver disease Diseases 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- 241001110060 Aeginetia Species 0.000 claims abstract description 6
- 229940079593 drug Drugs 0.000 claims abstract description 5
- 235000013305 food Nutrition 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000000287 crude extract Substances 0.000 claims description 16
- 238000002386 leaching Methods 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 239000002024 ethyl acetate extract Substances 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 241000746966 Zizania Species 0.000 claims description 7
- 235000002636 Zizania aquatica Nutrition 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 210000005228 liver tissue Anatomy 0.000 abstract description 11
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract description 9
- 235000002226 Ranunculus ficaria Nutrition 0.000 abstract description 9
- 210000004027 cell Anatomy 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 9
- 231100000753 hepatic injury Toxicity 0.000 abstract description 6
- 208000029618 autoimmune pulmonary alveolar proteinosis Diseases 0.000 abstract description 5
- 210000004185 liver Anatomy 0.000 abstract description 5
- 230000001681 protective effect Effects 0.000 abstract description 5
- 206010067125 Liver injury Diseases 0.000 abstract description 4
- 210000005229 liver cell Anatomy 0.000 abstract description 3
- 238000011160 research Methods 0.000 abstract description 3
- 230000004083 survival effect Effects 0.000 abstract description 3
- 230000002265 prevention Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- 210000002966 serum Anatomy 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 102000019197 Superoxide Dismutase Human genes 0.000 description 5
- 108010012715 Superoxide dismutase Proteins 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- YBWOXWSKTIHNHZ-SEYSHPTOSA-N Aeginetin Natural products O=C(O)/C(=C\C=C\C=C(/C=C/C=C(\C=C\[C@]1(O)[C@@](O)(C)CCCC1(C)C)/C)\C)/C YBWOXWSKTIHNHZ-SEYSHPTOSA-N 0.000 description 2
- TWGFYQIUSFIVDO-UHFFFAOYSA-N Aeginetolide Natural products C1CCC(C)(C)C2(O)CC(=O)OC21C TWGFYQIUSFIVDO-UHFFFAOYSA-N 0.000 description 2
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 2
- 108010082126 Alanine transaminase Proteins 0.000 description 2
- NYWCITDWPAZNBU-DYISAODMSA-N Azafrin Chemical compound OC(=O)\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@@]1(O)C(C)(C)CCC[C@@]1(C)O NYWCITDWPAZNBU-DYISAODMSA-N 0.000 description 2
- NYWCITDWPAZNBU-SVBPBHIXSA-N Azafrin Natural products CC(=CC=CC=C(C)C=CC(=O)O)C=CC=C(C)C=C[C@]1(O)C(C)(C)CCC[C@]1(C)O NYWCITDWPAZNBU-SVBPBHIXSA-N 0.000 description 2
- 206010019668 Hepatic fibrosis Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000308150 Orobanchaceae Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000003833 cell viability Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- KXMTXZACPVCDMH-UHFFFAOYSA-N methyl 4-[5-(hydroxymethyl)-7-methoxy-1,3-benzodioxol-4-yl]-7-methoxy-1,3-benzodioxole-5-carboxylate Chemical compound COC(=O)C1=CC(OC)=C2OCOC2=C1C1=C2OCOC2=C(OC)C=C1CO KXMTXZACPVCDMH-UHFFFAOYSA-N 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 description 1
- 206010008635 Cholestasis Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 206010072268 Drug-induced liver injury Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 206010019728 Hepatitis alcoholic Diseases 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- 206010020741 Hyperpyrexia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000002353 alcoholic hepatitis Diseases 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 231100000359 cholestasis Toxicity 0.000 description 1
- 230000007870 cholestasis Effects 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 201000008865 drug-induced hepatitis Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 206010019692 hepatic necrosis Diseases 0.000 description 1
- 230000007866 hepatic necrosis Effects 0.000 description 1
- 239000003547 immunosorbent Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000002731 protein assay Methods 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 102000014898 transaminase activity proteins Human genes 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 201000001862 viral hepatitis Diseases 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/203—Retinoic acids ; Salts thereof
-
- 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
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a new application of aeginetia indica polyene compounds, which is to use aeginetia indica polyene compounds as active ingredients to prepare drugs or health-care foods for preventing or treating liver diseases. The experimental results show that: aeginetia multiolefin E and scrophularia erythronic acid can improve the survival rate of the APAP-induced HepG2 cells, and show certain protective activity on liver cells; aeginetia indica polyene E and figwort red acid can effectively reduce CCl 4 The SOD activity of rat liver tissue can be obviously improved, and the SOD has certain prevention and treatment effects on liver injury. Therefore, the aeginetia indica polyene compounds are used as active ingredients for preparing the drugs or health care products for preventing and treating liver diseasesThe application of the aeginetia indica polyene compounds has important significance for the research and the application of the aeginetia indica polyene compounds.
Description
Technical Field
The invention belongs to a new application of aeginetia indica polyene compounds, and particularly relates to a new application of aeginetia indica polyene compounds in preparation of drugs for preventing or treating liver diseases.
Background
The liver is the central organ of human metabolism and nutrition, not only completes the synthesis and decomposition of carbohydrates, proteins and fats, but also needs the transformation of most endogenous and exogenous metabolic end products through the liver. Liver diseases are one of common diseases in modern life, when liver functions are in problem, digestive functions can be directly influenced, the digestion function is reduced, appetite is easily caused, absorption is influenced, sufficient energy cannot be provided for human bodies if digestion and absorption are carried out for a long time, and then the problems that the human bodies are easily fatigued, cannot concentrate, are dizziness and tinnitus can be caused, and even people can be in a worry.
Liver diseases, i.e., liver injury, include mainly viral hepatitis, alcoholic hepatitis and drug-induced hepatitis, which are clinically manifested as hepatic necrosis, fatty liver, cholestasis, hepatic fibrosis, cirrhosis, liver cancer, and the like, and the treatment of liver injury is still a global serious topic at present. Carbon tetrachloride is a hepatic fibrosis inducer and is often used in experiments of acute hepatic injury, namely, a mouse hepatic injury model is obtained by injecting carbon tetrachloride, and the hepatic injury condition is judged by detecting the contents of alanine aminotransferase (ALT/GPT), aspartate aminotransferase (AST/GOT) and superoxide dismutase (SOD) and propylene glycol (MDA) in liver tissues in the serum of a mouse.
Aeginetia polyene compounds, including Aeginetin (Aeginetin), azafrin (Azafrin), extracted from Orobanchaceae (Orobanchaceae), aeginetia (Aeginetia), carotenoid type, are commonly used for treating sore throat, cough, infantile hyperpyrexia, urinary tract infection, osteomyelitis and venomous snake bite.
However, no research report on the aeginetocin compound in preventing or treating liver diseases is found so far.
Disclosure of Invention
The object of the present invention is to solve at least the above drawbacks and to provide advantages which will be explained later.
In order to achieve these objects and other advantages of the present invention, a new use of aeginetobacter asiaticum polyene compounds is now provided, wherein aeginetobacter asiaticum polyene compounds are used as active ingredients for preparing drugs or health foods for preventing or treating liver diseases.
In the scheme, particularly, when the aeginetolide is used as an active ingredient for preparing a medicament or a health-care food for preventing or treating liver diseases, the aeginetolide can be prepared into oral medicaments or non-oral medicaments; wherein, the oral administration can be made into any conventional dosage forms, such as tablet, capsule, powder, granule, etc.; it can be made into injection for non-oral administration. Therefore, the method is suitable for various application scenes and has good market prospect.
Preferably, the aeginetoides polyene compound has the following chemical structural formula, which is referred to as chemical formula I for short:
Preferably, the compound is aeginetocin E, and has the following chemical structural formula, which is simply called chemical formula II:
preferably, the compound is scrophularia erythronic acid, and has the following chemical structural formula, which is referred to as chemical formula III for short:
the preparation method of the aeginetoides polyene compounds is characterized by comprising the following steps:
step one, wild rice is obtained and crushed to obtain wild rice powder.
And step two, repeatedly leaching the wild rice powder for 3 times by using an ethanol solution with the volume fraction of 70-80%, and combining the liquid obtained by leaching for 3 times to obtain a leaching solution.
And step three, sequentially filtering and concentrating the obtained leaching liquor under reduced pressure to obtain a crude extract.
And step four, dissolving the crude extract with water to obtain a crude extract, and sequentially performing petroleum ether extraction and ethyl acetate extraction to obtain the aeginetia indica ethyl acetate extract.
And step five, dissolving the aeginetia indica ethyl acetate extract by using methanol, filtering, separating by using an MCI column, concentrating a 60% methanol eluent, and separating out yellow solid to obtain the aeginetia indica polyene compound.
The feed-liquid ratio of the aeginetosa powder to the ethanol solution is 1:10 to 30 parts; the volume ratio of the ethyl acetate to the crude extract is 0.5-2: 1.
the preparation method of the aeginetoides polyene compounds is characterized by comprising the following steps:
step one, aeginetia indica is obtained and crushed to obtain aeginetia indica powder.
And step two, repeatedly leaching the wild rice powder for 3 times by using an ethanol solution with the volume fraction of 70-80%, and combining the liquid obtained by leaching for 3 times to obtain a leaching solution.
And step three, sequentially filtering and concentrating the obtained leaching liquor under reduced pressure to obtain a crude extract.
And step four, dissolving the crude extract with water to obtain a crude extract, and sequentially performing petroleum ether extraction and ethyl acetate extraction to obtain the aeginetia indica ethyl acetate extract.
And step five, dissolving the aeginetia indica ethyl acetate extract by using methanol, filtering, separating by using an MCI column, concentrating 85% methanol eluent, and separating out red solid to obtain aeginetia indica polyene compound and figwort red acid.
Preferably, the MCI column is an 8 × 20 cm small-hole resin column; the MCI column separation specifically comprises: passing through a column by adopting a methanol-water ratio; the gradient elution was set to a ratio of pure water to methanol of 100: 0. 80: 20. 60: 40. 40: 60. 15: 85. 0:100, 1L per ratio.
Preferably, the medicine is a medicinal preparation prepared by taking the aeginetoides polyene compound as an active ingredient and adding pharmaceutically acceptable carriers or auxiliary ingredients.
The invention has the advantages that:
firstly, the invention can promote the aeginetia indica polyene compound to fully exert the medicinal value thereof, and has important significance for the research and application of the aeginetia indica polyene compound.
Secondly, the aeginetia polyene E and the scrophularia erythronic acid are extracted from aeginetia plants to prepare the medicine for preventing and treating the liver diseases, so that the pain and trouble caused by surgical excision, chemotherapy, radiotherapy and the like can be reduced.
In addition, when the aeginetoides polyene compound is used as an active ingredient for preparing a medicament or health-care food for preventing or treating liver diseases, the aeginetoides polyene compound can be prepared into oral medicaments or non-oral medicaments; wherein, the oral administration medicine can be made into any conventional dosage forms, such as tablets, capsules, powder, granules and the like; it can be made into injection for non-oral administration. Therefore, the method is suitable for various application scenes and has good market prospect.
Detailed Description
The present invention is further described in detail below with reference to examples to enable those skilled in the art to practice the invention with the help of the following description.
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
It is to be noted that the experimental methods described in the following embodiments are all conventional methods unless otherwise specified, and the reagents and materials are commercially available unless otherwise specified.
Example 1
1 extraction and separation of aeginetia indica polyene compounds
Step one, drying 20kg of aeginetia indica whole grass, and crushing to obtain aeginetia indica powder.
Dispersing wild mushroom powder into an ethanol solution with the volume fraction of 70-80%, soaking for 5 days at normal temperature, extracting, repeatedly soaking and extracting for 3 times, and combining the liquid obtained by 3 times of leaching to obtain a leaching solution; wherein the feed-liquid ratio of the aeginetia indica powder to the ethanol solution is 1:10 to 30.
And step three, sequentially filtering and concentrating the leaching liquor obtained in the step two under reduced pressure to obtain a crude extract.
Step four, dissolving the crude extract with water to obtain a crude extract, extracting with petroleum ether to remove fat-soluble impurities, and then extracting the crude extract with ethyl acetate to obtain a aeginetia indica ethyl acetate extract; wherein the volume ratio of the ethyl acetate to the crude extract is 0.5-2: 1.
step five, dissolving the aeginetia indica ethyl acetate extract by using methanol, filtering, separating by using a small-hole resin column (MCI filler) with the size of 8 multiplied by 20 cm, concentrating a 60% methanol eluent, and separating out yellow solid which is aeginetia indica polyene E and accounts for 6.8 g; concentrating 85% methanol eluate to obtain 0.6 g red solid of radix scrophulariae erythronic acid; wherein the weight ratio of the ethyl acetate extract to the MCI filler is 1:40 to 50; the elution process adopts water-methanol gradient elution, and the gradient elution is set as the ratio of pure water to methanol is respectively 100: 0. 80: 20. 60: 40. 40: 60. 15: 85. 0:100, 1L per ratio.
2 structural identification of aeginetia indica polyene compounds
2.1 Structure of aeginetia polyene compounds:
2.2 nuclear magnetic resonance data (Varian-600 MHz NMR) of aeginetopsis polyacea:
1 H NMR(600MHz,d-CD 3 OD):δ H 7.33(d,J=11.8Hz,1H),7.05–6.94(m,1H),6.81(dd,J=15.0,11.5Hz,1H),6.67–6.57(m,1H),6.43(d,J=9.8Hz,1H),6.40(d,J=8.9Hz,1H),6.32(d,J=12.6Hz,1H),6.30(d,J=16.2Hz,1H),6.21(d,J=11.3Hz,1H),2.03(s,3H),2.00(s,3H),1.95(s,3H),1.91–1.86(m,1H),1.85–1.78(m,1H),1.71(td,J=13.1,3.2Hz,1H),1.47(d,J=12.4Hz,1H),1.40–1.33(m,1H),1.21(s,3H),1.17(d,J=13.5Hz,1H),1.09(s,3H),0.81(s,3H).
13 C-NMR(151MHz,d-CD 3 OD):δ C 171.96,141.20,140.38,137.92,137.73,137.27,135.52,132.52,132.35,131.80,129.17,127.91,127.35,80.71,76.02,39.68,37.47,36.76,27.55,27.37,25.75,19.09,13.26,12.95,12.83。
2.3 nuclear magnetic resonance data of the compound scrophularia erythronic acid:
1 H NMR(600MHz,d-CD 3 OD):δ H 7.38(d,J=15.5Hz,1H),6.96–6.87(m,1H),6.78(dd,J=15.0,11.5Hz,1H),6.75–6.66(m,1H),6.60(d,J=11.7Hz,1H),6.42(dd,J=15.5,10.5Hz,2H),6.32(d,J=11.9Hz,2H),6.29(d,J=16.0Hz,1H),6.21(d,J=11.4Hz,1H),5.87(d,J=15.5Hz,1H),2.02(s,3H),2.00(s,3H),1.95(s,3H),1.92–1.88(m,1H),1.83(d,J=3.7Hz,1H),1.71(td,J=13.1,3.3Hz,1H),1.47(d,J=13.1Hz,2H),1.40–1.35(m,2H),1.29(s,2H),1.21(s,3H),1.17(d,J=13.1Hz,1H),1.09(s,3H),0.81(s,3H).
13 C-NMR(151MHz,d-CD 3 OD):δ C 170.97,159.59,150.61,140.84,140.18,138.10,137.44,135.56,135.40,134.48,132.93,132.34,131.93,129.98,127.47,117.19,80.71,76.02,39.68,37.46,36.76,27.56,27.38,25.75,19.09,13.26,12.92,12.56。
3 activity test of aeginetia indica polyene compounds
3.1 protective Activity of Aeginetia indica polyene Compounds on APAP-induced HepG2 cells
(1) Test method
Step a, taking people in logarithmic growth phaseHepatoma cell line HepG2, and preparing a single cell suspension of the HepG2 cell culture solution with the RPMI-1640 culture solution containing 10% fetal bovine serum, inoculating the suspension into a 96-well plate in an amount of 2000 cells per well, in a volume of 100. Mu.l per well, in 5% CO 2 The culture was carried out at a concentration of 37 ℃ for 24 hours in an incubator.
B, the medicine components are aeginetia polyene E group and figwort red acid group, and the aeginetia polyene E or the figwort red acid and acetaminophen (APAP, 8 mM) are used for treating cells together respectively; the positive control group treated cells with APAP and Bicyclol (Bicyclol) together; model groups treated cells with acetaminophen; blank groups were left untreated. The above fractions were treated and incubated for 24 hours.
And c, after the incubation is finished, adding 5mg/ml MTT solution into each hole, continuously culturing for 4 hours, sucking the culture solution, adding DMSO, shaking uniformly, then incubating for 3 hours, finally measuring the OD value at 517nm on an enzyme-linked immunosorbent monitor, and calculating the cell survival rate (%).
(2) Calculation of cell viability
Cell viability% = experimental group OD value/blank group OD × 100%. The results are shown in Table 2.
Table 1: aeginetoxico polyene E and scrophularia erythronic acid have protective activity on HepG2 liver cells (n =5, ** P<0.01)
(3) Analysis of results
Compared with a model group, the aeginetia polyene E and the scrophularia erythronic acid can improve the survival rate of the APAP-induced HepG2 cells and show certain protective activity on liver cells.
3.2 Aeginetia polyakenes on CCl 4 Protective action for rat liver damage
(1) Inspection method
Solution preparation: weighing wild mushroom polyene E and radix scrophulariae erythronic acid, and dissolving with 0.5% CMC-Na to obtain 100mg/mL concentration.
Animal administration: 40 male rats were randomly divided into a blank group and a model groupAeginetia indica polyene E and figwort red acid groups, wherein each group comprises 10 aeginetia indica polyene E and figwort red acid groups. Gavage polyene E and radix scrophulariae erythrocid group are administered according to 100mg/Kg intragastric administration, and the normal control group and model group are both administered with equal amount of 0.5% CMC-Na solution, and are intragastric administered for 1 time per day, and are continuously administered for 7 days. After 2h of the last administration, except the blank group, the mice of the other groups were injected with 0.2% carbon tetrachloride (CCl) intraperitoneally 4 ) 20mL/Kg of olive oil solution. After fasting without water deprivation for 16h, weighing was performed, mice were killed by dislocation, and blood samples and liver tissues were collected for further examination.
And (3) detection: serum is detected by a kit, and glutamic-pyruvic transaminase (ALT) and glutamic-oxalacetic transaminase (AST) in the serum are determined according to the instruction. Liver tissue was weighed to 200mg, homogenized in 1.8mL of pre-cooled physiological saline, centrifuged at 1500 Xg for 5min, and the homogenate collected. The homogenate was first assayed for protein concentration in the homogenate according to the Bio-Rad protein assay kit method. Then, taking the homogenate, and detecting the SOD activity, MDA content and ROS generation level of the homogenate according to the steps of the detection kit specification. Finally, the contents of the above factors in the homogenate are normalized according to the protein concentration.
(2) Test results
The test results are expressed as means + -standard deviation (mean + -SD), and pairwise comparison of means between sets of data was performed using a one-way ANOVA post-hoc SNK-q test. Differences were considered statistically significant when P < 0.05. The results are shown in Table 2.
Table 2: influence of aeginetocin E and scrophularia erythronolic acid on rat serum index (n = 8)
(3) Analysis of results
Compared with the control group, the wild mushroom polyene E group has significantly increased ALT and AST activities (P) in the rat serum of the model group<0.01). Compared with the model group, the ALT and AST activities in the rat serum of aeginetia indica polyene E group and figwort red acid group are both reduced (P)<0.01 And the aeginetia indica polyene E group and the scrophularia erythropolis acid group have no obvious difference. These results indicate that aeginetia polyene E and scrophularia erythronic acid can both alleviate CCl 4 Leading to severe liver diseaseLiver damage in mice.
The antioxidant enzyme SOD activity in rat liver tissue of the model group is obviously reduced (P)<0.01 ); compared with the model group, the SOD activity in the liver tissues of the rats of the aeginetia indica polyene E group and the figwort red acid group is obviously increased (P)<0.01 And the scrophularia rubra group is more remarkable than the aeginetia indica polyene E group. Compared with the blank group, the liver tissue of the rat in the model group has obviously increased MDA content (P)<0.01 Reflecting the rise of lipid peroxidation degree in the rat body; compared with the model group, the rat liver tissues of the aeginetia indica polyene E group and the figwort red acid group have obviously reduced MDA content (P)<0.01). Measurement of ROS levels in rat liver showed that the ROS production levels in the liver tissue of the model group rats were increased compared to the blank group (P)<0.01 ); the levels of ROS production were significantly reduced in the liver tissues of rats in the aeginetia polyene E group and the scrophularia erythronic acid group (P) compared to the model group (P)<0.01 The effect is particularly obvious in a high-dose group (P)<0.01). The results show that aeginetia indica polyene E and scrophularia erythronic acid can reduce CCl 4 Resulting in oxidative stress levels in liver tissues of rats with liver diseases.
While embodiments of the invention have been disclosed above, it is not intended that they be limited to the applications set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. The invention is therefore not to be limited to the specific details described herein, without departing from the general concept as defined by the appended claims and their equivalents.
Claims (8)
1. A new application of aeginetoides polyene compounds is characterized in that aeginetoides polyene compounds are used as active ingredients for preparing medicines or health-care foods for preventing or treating liver diseases.
5. the preparation method of the aeginetoides polyene compounds is characterized by comprising the following steps:
step one, obtaining wild rice and crushing to obtain wild rice powder;
step two, repeatedly leaching the wild rice powder for 3 times by using an ethanol solution with the volume fraction of 70-80%, and combining the liquid obtained by leaching for 3 times to obtain a leaching solution;
step three, sequentially filtering and concentrating the obtained leaching liquor under reduced pressure to obtain a crude extract;
step four, dissolving the crude extract with water to obtain a crude extract, and sequentially performing petroleum ether extraction and ethyl acetate extraction to obtain a aeginetia indica ethyl acetate extract;
step five, dissolving aeginetia indica ethyl acetate extract by using methanol, filtering, separating by using an MCI column, concentrating 60% methanol eluent, and separating out yellow solid to obtain aeginetia indica polyene compound of claim 2;
the feed-liquid ratio of the wild mushroom powder to the ethanol solution is 1:10 to 30 percent; the volume ratio of the ethyl acetate to the crude extract is 0.5-2: 1.
6. the method for preparing aeginetopes compounds according to claim 5, wherein the fifth step is:
step five, dissolving aeginetia indica ethyl acetate extract by using methanol, filtering, separating by using an MCI column, concentrating 85% methanol eluent, and separating out red solid to obtain aeginsenolic acid of the aeginetia indica polyene compound in claim 3.
7. The preparation method of aeginetoides polyene compounds according to any one of claims 5 or 6, wherein the MCI column is a small-hole resin column of 8 x 20 cm; the MCI column separation specifically comprises:
passing through a column by adopting a methanol-water ratio; the gradient elution was set to a ratio of pure water to methanol of 100: 0. 80: 20. 60: 40. 40: 60. 15: 85. 0:100, 1L per ratio.
8. The new use of aeginetia indica polyene compound according to any one of claims 1 to 4, wherein the medicament is a pharmaceutical preparation prepared by using aeginetia indica polyene compound as an active ingredient and adding pharmaceutically acceptable carriers or auxiliary ingredients.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210987194.3A CN115212196B (en) | 2022-08-17 | 2022-08-17 | Application of aeginetia mulosa polyene compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210987194.3A CN115212196B (en) | 2022-08-17 | 2022-08-17 | Application of aeginetia mulosa polyene compound |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115212196A true CN115212196A (en) | 2022-10-21 |
CN115212196B CN115212196B (en) | 2023-09-29 |
Family
ID=83615663
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210987194.3A Active CN115212196B (en) | 2022-08-17 | 2022-08-17 | Application of aeginetia mulosa polyene compound |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115212196B (en) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07258158A (en) * | 1994-03-14 | 1995-10-09 | Marigen Sa | Biotenside solvent for medicine and cosmetic |
CN102772397A (en) * | 2012-08-06 | 2012-11-14 | 上海中医药大学 | New application of azafrin |
CN103254163A (en) * | 2013-05-17 | 2013-08-21 | 南京泽朗医药科技有限公司 | Preparation method of aeginetolide |
-
2022
- 2022-08-17 CN CN202210987194.3A patent/CN115212196B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07258158A (en) * | 1994-03-14 | 1995-10-09 | Marigen Sa | Biotenside solvent for medicine and cosmetic |
CN102772397A (en) * | 2012-08-06 | 2012-11-14 | 上海中医药大学 | New application of azafrin |
CN103254163A (en) * | 2013-05-17 | 2013-08-21 | 南京泽朗医药科技有限公司 | Preparation method of aeginetolide |
Non-Patent Citations (1)
Title |
---|
SHUYU YANG , ET AL: ""Cardioprotective role of azafrin in against myocardial injury in rats via activation of the Nrf2-ARE pathway"", 《PHYTOMEDICINE》, vol. 18, pages 1 - 22 * |
Also Published As
Publication number | Publication date |
---|---|
CN115212196B (en) | 2023-09-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN106336445B (en) | The preparation method and application of compound 20 (R) ginseng sapoglycoside Rg 3 | |
CN104644697B (en) | The preparation method and applications of ganoderma lucidum Ultramicro-powder | |
CN111166734A (en) | Use of naphthoquinones to treat pneumonia caused by pathogenic organisms | |
CN106822166B (en) | A kind of drug for preventing and treating diabetes and hyperlipidemia and its application in pharmacy | |
CN104688760A (en) | Pharmaceutical composition composed of saikoside A and taurine and use thereof | |
CN112353792A (en) | Application of eupatilin in preparing medicament for preventing or treating alcoholic liver disease | |
CN103360452B (en) | The Synthesis and applications of Muskmelon Base tetracyclic triterpene cucurbitane compound | |
CN115212196A (en) | New application of aeginetia indica polyene compounds | |
WO2021120966A1 (en) | Sheep horn keratin, preparation method therefor, pharmaceutical composition thereof and use thereof | |
CN103494813A (en) | Application of hydrochloric acid demethyleneberberine in preparation of drug for preventing and/or treating acute or chronic alcoholic liver disease | |
CN106995479A (en) | Compound ginsenoside Rk1 preparation method and application | |
CN113797235A (en) | Preparation method of compound ganoderma lucidum spore oil with liver protection effect | |
CN103565846B (en) | Preparation method of stingray extract and application of stingray extract in alcoholic liver protection medicine | |
TWI620815B (en) | Preparation and use of antrodia cinnamomea mycelia fermentation product for improving nonalcoholic steatohepatitis (nash) | |
CN108186693B (en) | Preparation method of paecilomyces hepiali active substance for reducing uric acid or treating hyperuricemia, active substance prepared by method and application thereof | |
CN102342962A (en) | Application of extracts from Portulaca oleracea L. in preparation of anti-liver injury medicines and health foods | |
CN111329871A (en) | Preparation method and application of product of cordyceps militaris for preventing and treating liver cancer | |
WO2018188547A1 (en) | New use of cordyceps sobolifera | |
CN110840950A (en) | Application of Russian tea and/or Russian tea extract in preparation of medicines for preventing and treating non-alcoholic liver disease and/or non-alcoholic liver injury | |
WO2018188548A1 (en) | Traditional chinese medicine composition with hypoglycemic effect | |
CN114272354B (en) | Traditional Chinese medicine composition for preventing and improving senile dementia, preparation method and application thereof | |
CN107595934A (en) | A kind of walnut grouts polyphenol purified is preparing the purposes in treating intestinal bacilli illness medicine | |
CN104069149A (en) | Method for processing traditional Chinese medicine decoction piece by using bear gall as matrix | |
CN102793740B (en) | Nutrient particles with auxiliary protecting function on chemical liver injury | |
CN109512808B (en) | Application of methyl palmitate in preparation of medicine for preventing or treating fatty liver |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20221021 Assignee: GUANGXI HENGDERUN BIOLOGICAL SCIENCE & TECHNOLOGY Co.,Ltd. Assignor: GUANGXI BOTANICAL GARDEN OF MEDICINAL PLANTS Contract record no.: X2023980045685 Denomination of invention: The Use of Wild Rice Polyene Compounds Granted publication date: 20230929 License type: Common License Record date: 20231106 |