CN113943211B - 维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 - Google Patents
维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 Download PDFInfo
- Publication number
- CN113943211B CN113943211B CN202111051449.7A CN202111051449A CN113943211B CN 113943211 B CN113943211 B CN 113943211B CN 202111051449 A CN202111051449 A CN 202111051449A CN 113943211 B CN113943211 B CN 113943211B
- Authority
- CN
- China
- Prior art keywords
- petroleum ether
- hexahydro
- isopropyl
- gradient elution
- preparation
- 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.)
- Active
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 206010061218 Inflammation Diseases 0.000 title claims abstract description 12
- 230000004054 inflammatory process Effects 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims abstract description 10
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 13
- 150000004141 diterpene derivatives Chemical class 0.000 title abstract description 9
- 229940079593 drug Drugs 0.000 title abstract description 8
- 229930004069 diterpene Natural products 0.000 title abstract description 7
- 239000000463 material Substances 0.000 title abstract description 5
- 241000951473 Schizonepeta Species 0.000 claims abstract description 34
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 230000005764 inhibitory process Effects 0.000 claims abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 108
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 84
- 239000003208 petroleum Substances 0.000 claims description 54
- 238000010828 elution Methods 0.000 claims description 40
- 238000010898 silica gel chromatography Methods 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001033 ether group Chemical group 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 241000894006 Bacteria Species 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 238000002791 soaking Methods 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 9
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 7
- 241000588724 Escherichia coli Species 0.000 abstract description 6
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 6
- 229940124350 antibacterial drug Drugs 0.000 abstract description 6
- 238000002474 experimental method Methods 0.000 abstract description 5
- 238000000338 in vitro Methods 0.000 abstract description 4
- 230000003285 pharmacodynamic effect Effects 0.000 abstract description 4
- 229940126214 compound 3 Drugs 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 5
- 238000005457 optimization Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- -1 terpenoid compounds Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- 241001529733 Nepeta Species 0.000 description 1
- 241001612423 Nepeta bracteata Species 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
- 208000004880 Polyuria Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010044302 Tracheitis Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
- C07C35/42—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings derived from the phenanthrene skeleton
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
本发明涉及大苞荆芥分离纯化技术领域,是一种维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用。本发明首次公开了化合物3,4,4a,9,10,10a‑hexahydro‑1‑(hydroxymethyl)‑7‑isopropyl‑2,4a‑dimethylphenanthren‑9‑ol(nepetabrate C),并将该化合物进行了体外抗炎及抗菌药效学实验,实验明显可以看出该化合物对RAW 264.7细胞和金黄色葡萄球菌及大肠杆菌具有较强的抑制作用,从而使该化合物能够作为制备预防炎症及抑菌药物或/和制备抗炎、抗菌药物或/和制备防治炎症及抑菌保健品的应用。
Description
技术领域
本发明涉及大苞荆芥分离纯化技术领域,是一种维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用,维吾尔药材中二萜成分为所述3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthre n-9-ol(nepetabrate C)的简称。
背景技术
大苞荆芥Nepeta bracteata Benth为唇形科Labiatae荆芥属Nepeta植物,主要分布于巴基斯坦,尼泊尔,伊朗等国家,维吾尔名为“祖发”,习称神香草,临床用药广泛,主要以进口为主。其全草入药,气微清香,味淡、性微湿,入肺、肝经,具有镇咳平喘、清热利湿的作用,临床上用于治疗气管炎症,咳嗽气喘、感冒发烧、小便不利等症状。此外,大苞荆芥还具有来源容易、成本低廉、临床疗效可靠、毒副作用小等特点。迄今为止,对大苞荆芥进行探究的重点以及基础理论研究还不多见,现代药理学表明,其提取物具有显著的抗炎、抑菌活性,但尚未对化学成分进行相关研究,大苞荆芥可能是一味治疗呼吸系统疾病很好的物种,因此,近年来备受人们的关注。
大苞荆芥的药效主要来源于其中的萜类化合物,包括单萜类和二萜类化合物,其中优势成分二萜类成分抗炎、抑菌活性较好,因此,开发和利用大苞荆芥的二萜类单体化合物,进一步挖掘其潜在的药用价值,并对其单体化合物的结构和理化性质进行确定和表征,对于开发利用大苞荆芥具有重要意义。
发明内容
本发明提供了一种3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)及其制备方法和应用,克服了上述现有技术之不足,其首次公开了3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isoprop yl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)及其作为制备预防炎症及抑菌药物或/和制备抗炎、抗菌药物或/和制备防治炎症及抑菌保健品的应用。
本发明的技术方案之一是通过以下措施来实现的:一种3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C),化学结构式为
下面是对上述发明技术方案之一的进一步优化或/和改进:
上述按照下述方法制备得到:第一步,将大苞荆芥粉碎并加入乙醇,在室温下浸泡3小时至4小时后,在50℃至60℃条件下加热回流提取3次,每次1小时至3小时,合并每次回流提取液并减压回收、浓缩,得大苞荆芥总浸膏;第二步,将大苞荆芥总浸膏用水分散,依次用石油醚和二氯甲烷萃取,得到石油醚部位和二氯甲烷部位;第三步,取石油醚部位浸膏用硅胶柱色谱梯度洗脱分离后得到8个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为1:0、100:1、50:1、25:1、8:1、5:1、1:1、1:0;第四步,将得到的8个馏分中第6个馏分再经硅胶柱色谱梯度洗脱分离后得到5个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为20:1、10:1、3:1、1:1、0:1;第五步,再将得到的5个馏分中第3个馏分再经硅胶柱色谱梯度洗脱分离后得到3个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为10:1、5:1、3:1;第六步,再将得到的3个馏分中第3个馏分再经高效液相色谱梯度洗脱纯化分离,并收集洗脱物,在第28.6分钟处得到3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)。
上述第一步中,每1g大苞荆芥加入8ml至10ml乙醇。
上述第六步中,高效液相色谱梯度洗脱的洗脱液为甲醇和水的混合液,其中,甲醇和水的体积比为85:15。
本发明的技术方案之二是通过以下措施来实现的:一种3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的制备方法,按照下述步骤进行:第一步,将大苞荆芥粉碎并加入乙醇,在室温下浸泡3小时至4小时后,在50℃至60℃条件下加热回流提取3次,每次1小时至3小时,合并每次回流提取液并减压回收、浓缩,得大苞荆芥总浸膏;第二步,将大苞荆芥总浸膏用水分散,依次用石油醚和二氯甲烷萃取,得到石油醚部位和二氯甲烷部位;第三步,取石油醚部位浸膏用硅胶柱色谱梯度洗脱分离后得到8个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为1:0、100:1、50:1、25:1、8:1、5:1、1:1、1:0;第四步,将得到的8个馏分中第6个馏分再经硅胶柱色谱梯度洗脱分离后得到5个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为20:1、10:1、3:1、1:1、0:1;第五步,再将得到的5个馏分中第3个馏分再经硅胶柱色谱梯度洗脱分离后得到3个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为10:1、5:1、3:1;第六步,再将得到的3个馏分中第3个馏分再经高效液相色谱梯度洗脱纯化分离,并收集洗脱物,在第28.6分钟处得到3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)。
下面是对上述发明技术方案之二的进一步优化或/和改进:
上述第一步中,每1g大苞荆芥加入8ml至10ml乙醇。
上述第六步中,高效液相色谱梯度洗脱的洗脱液为甲醇和水的混合液,其中,甲醇和水的体积比为85:15。
本发明的技术方案之三是通过以下措施来实现的:一种3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)作为制备预防炎症及抑菌药物的应用。
本发明的技术方案之四是通过以下措施来实现的:一种3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)作为制备抗炎及抗菌药物的应用。
本发明的技术方案之五是通过以下措施来实现的:一种3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)作为制备防治炎症及抑菌保健品的应用。
本发明首次公开了化合物3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopr opyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C),并将该化合物进行了体外抗炎及抗菌药效学实验,实验明显可以看出该化合物对RAW 264.7细胞和金黄色葡萄球菌及大肠杆菌具有较强的抑制作用,从而使该化合物能够作为制备预防炎症及抑菌药物或/和制备抗炎、抗菌药物或/和制备防治炎症及抑菌保健品的应用。
附图说明
附图1为本发明所述3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的化学结构图。
附图2为本发明所述3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的1H-NMR谱图。
附图3为本发明所述3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的13C-APT谱图。
具体实施方式
本发明不受下述实施例的限制,可根据本发明的技术方案与实际情况来确定具体的实施方式。本发明中所提到各种化学试剂和化学用品如无特殊说明,均为现有技术中公知公用的化学试剂和化学用品;本发明中的百分数如没有特殊说明,均为质量百分数;本发明中的溶液若没有特殊说明,均为溶剂为水的水溶液,例如,盐酸溶液即为盐酸水溶液;本发明中的常温、室温一般指15℃到25℃的温度,一般定义为25℃。
下面结合实施例对本发明作进一步描述:
实施例1:该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C),其特征在于化学结构式为
将本发明实施例1所述的3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopr opyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)进行核磁共振氢谱(1H-NMR)和核磁共振碳谱(13C-APT)分析。
本实施例所述的3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的1H-NMR谱图如图2所示。
本实施例所述的该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的13C-APT谱图如图3所示。
对图2和图3进行图谱解析,并将图2和图3各峰进行归属,图2和图3的各峰归属如表1所示,通过表1的数据可知,本实施例所述的3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)的化学结构式如图1所示,易溶于氯仿、甲醇。
实施例2:该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C),按照下述方法制备得到:第一步,将大苞荆芥粉碎并加入乙醇,在室温下浸泡3小时至4小时后,在50℃至60℃条件下加热回流提取3次,每次1小时至3小时,合并每次回流提取液并减压回收、浓缩,得大苞荆芥总浸膏;第二步,将大苞荆芥总浸膏用水分散,依次用石油醚和二氯甲烷萃取,得到石油醚部位和二氯甲烷部位;第三步,取石油醚部位浸膏用硅胶柱色谱梯度洗脱分离后得到8个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为1:0、100:1、50:1、25:1、8:1、5:1、1:1、1:0;第四步,将得到的8个馏分中第6个馏分再经硅胶柱色谱梯度洗脱分离后得到5个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为20:1、10:1、3:1、1:1、0:1;第五步,再将得到的5个馏分中第3个馏分再经硅胶柱色谱梯度洗脱分离后得到3个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为10:1、5:1、3:1;第六步,再将得到的3个馏分中第3个馏分再经高效液相色谱梯度洗脱纯化分离,并收集洗脱物,在第28.6分钟处得到3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)。
实施例3:作为上述实施例的优化,该3,4,4a,9,10,10a-hexahydro-1-(hydroxymet hyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C),按照下述方法制备得到:第一步,将大苞荆芥粉碎并加入乙醇,在室温下浸泡3小时或4小时后,在50℃或60℃条件下加热回流提取3次,每次1小时或3小时,合并每次回流提取液并减压回收、浓缩,得大苞荆芥总浸膏;第二步,将大苞荆芥总浸膏用水分散,依次用石油醚和二氯甲烷萃取,得到石油醚部位和二氯甲烷部位;第三步,取石油醚部位浸膏用硅胶柱色谱梯度洗脱分离后得到8个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为1:0、100:1、50:1、25:1、8:1、5:1、1:1、1:0;第四步,将得到的8个馏分中第6个馏分再经硅胶柱色谱梯度洗脱分离后得到5个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为20:1、10:1、3:1、1:1、0:1;第五步,再将得到的5个馏分中第3个馏分再经硅胶柱色谱梯度洗脱分离后得到3个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为10:1、5:1、3:1;第六步,再将得到的3个馏分中第3个馏分再经高效液相色谱梯度洗脱纯化分离,并收集洗脱物,在第28.6分钟处得到3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)。
实施例4:作为上述实施例的优化,第一步中,每1g大苞荆芥加入8ml至10ml乙醇。
实施例5:作为上述实施例的优化,第六步中,高效液相色谱梯度洗脱的洗脱液为甲醇和水的混合液,其中,甲醇和水的体积比为85:15。
实施例6:该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)作为制备预防炎症及抑菌药物的应用。
实施例7:该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)作为制备抗炎及抗菌药物的应用。
实施例8:该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)作为制备防治炎症及抑菌保健品的应用。
实施例9:该3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)按照下述方法得到:第一步,将大苞荆芥粉碎并加入乙醇,在室温下浸泡3小时后,在50℃条件下加热回流提取3次,每次2小时,合并每次回流提取液并减压回收、浓缩,得大苞荆芥总浸膏;第二步,将大苞荆芥总浸膏用水分散,依次用石油醚和二氯甲烷萃取,得到石油醚部位和二氯甲烷部位;第三步,取石油醚部位浸膏用硅胶柱色谱梯度洗脱分离后得到8个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为1:0、100:1、50:1、25:1、8:1、5:1、1:1、1:0;第四步,将得到的8个馏分中第6个馏分再经硅胶柱色谱梯度洗脱分离后得到5个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为20:1、10:1、3:1、1:1、0:1;第五步,再将得到的5个馏分中第3个馏分再经硅胶柱色谱梯度洗脱分离后得到3个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为10:1、5:1、3:1;第六步,再将得到的3个馏分中第3个馏分再经高效液相色谱梯度洗脱纯化分离,并收集洗脱物,在第28.6分钟处得到3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropy l-2,4a-dimethylphenanthren-9-ol(nepetabrate C)。
将本发明实施例9得到的3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopr opyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)进行体外抗炎及抗菌药效学实验,体外抗炎及抗菌药效学实验利用MTT比色法。
以3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylph enanthren-9-ol(nepetabrate C)为实验组,以Aspinin(阿司匹林,抗炎药物)为对照组,同时设立空白组,实验组、对照组和空白组选取RAW 264.7细胞为实验对象,培养基稀释后,以6×104/ml的密度接种于96孔板,每孔100μl,培养箱中正常培养24小时后,各组加入相对应的药物,使各组药物的最终浓度分别为2.5μg/ml(1组),5μg/ml(2组),10μg/ml(3组),20μg/ml(4组),40μg/ml(5组),共设5个浓度,每个浓度3个复孔;培养48小时后,于每孔加MTT 10μl染色;继续培养四小时后,吸弃原培养液,每孔加入DMSO 150μl,置摇床上低速振荡10min,使结晶物充分溶解,并于酶联免疫检测仪570nm波长处检测光密度值,根据光密度值计算50%抑制浓度(IC50,μM),光密度值计算IC50的计算方法为现有公知技术。实验组、对照组对RAW 264.7细胞的IC50如表2所示。表2数据可以看出,本发明所述的3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)对RAW264.7细胞均具有一定的抑制作用。
以3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylph enanthren-9-ol(nepetabrate C)为实验组,以Penicillin(阿莫西林,抗菌药物)为对照组,同时设立空白组,实验组、对照组和空白组选取金黄色葡萄球菌和大肠杆菌为实验对象,将样品以无菌水或DMSO稀释一定倍数后,离心取100μL加入指示菌平板的孔内,做为抑菌实验孔,取新鲜培养的指示菌株,将菌悬液浓度调至0.5McFarland并均匀涂布在上述平板上,放置相应温度下培养24h或48h,观察各平皿的菌落生长情况。向孔中加入100μL新鲜培养基做为阴性对照孔,阿莫西林溶液做为阳性对照。培养基稀释后,以6×104/ml的密度接种于96孔板,每孔100μl,培养箱中正常培养24小时后,各组加入相对应的药物,使各组药物的最终浓度分别为2.5μg/ml(1组),5μg/ml(2组),10μg/ml(3组),20μg/ml(4组),40μg/ml(5组),共设5个浓度,每个浓度3个复孔;培养48小时后,于每孔加MTT 10μl染色;继续培养四小时后,吸弃原培养液,每孔加入DMSO 150μl,置摇床上低速振荡10min,使结晶物充分溶解,并于酶联免疫检测仪570nm波长处检测光密度值,根据光密度值计算50%抑制浓度(IC50,μM),光密度值计算IC50的计算方法为现有公知技术。实验组、对照组对金黄色葡萄球菌和大肠杆菌的IC50如表3所示。表3数据可以看出,本发明所述的3,4,4a,9,10,10a-hexahydro-1-(hydroxymethyl)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C)对金黄色葡萄球菌和大肠杆菌均具有一定的抑制作用。
综上所述,本发明首次公开了化合物3,4,4a,9,10,10a-hexahydro-1-(hydroxymethy l)-7-isopropyl-2,4a-dimethylphenanthren-9-ol(nepetabrate C),并将该化合物进行了体外抗炎及抗菌药效学实验,实验明显可以看出该化合物对RAW 264.7细胞和金黄色葡萄球菌及大肠杆菌具有较强的抑制作用,从而使该化合物能够作为制备预防炎症及抑菌药物或/和制备抗炎、抗菌药物或/和制备防治炎症及抑菌保健品的应用。
以上技术特征构成了本发明的实施例,其具有较强的适应性和实施效果,可根据实际需要增减非必要的技术特征,来满足不同情况的需求。
表1
表2
表3
Claims (7)
1.一种3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇,其特征在于3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇即为nepetabrate C,其化学结构式为
2.一种根据权利要求1所述的3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇的制备方法,其特征在于按照下述步骤进行:第一步,将大苞荆芥粉碎并加入乙醇,在室温下浸泡3小时至4小时后,在50℃至60℃条件下加热回流提取3次,每次1小时至3小时,合并每次回流提取液并减压回收、浓缩,得大苞荆芥总浸膏;第二步,将大苞荆芥总浸膏用水分散,依次用石油醚和二氯甲烷萃取,得到石油醚部位和二氯甲烷部位;第三步,取石油醚部位浸膏用硅胶柱色谱梯度洗脱分离后得到8个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为1:0、100:1、50:1、25:1、8:1、5:1、1:1、1:0;第四步,将得到的8个馏分中第6个馏分再经硅胶柱色谱梯度洗脱分离后得到5个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为20:1、10:1、3:1、1:1、0:1;第五步,再将得到的5个馏分中第3个馏分再经硅胶柱色谱梯度洗脱分离后得到3个馏分,其中,硅胶柱色谱梯度洗脱液包括石油醚和乙酸乙酯,石油醚和乙酸乙酯的体积比依次为10:1、5:1、3:1;第六步,再将得到的3个馏分中第3个馏分再经高效液相色谱梯度洗脱纯化分离,并收集洗脱物,在第28.6分钟处得到nepetabrate C,即为3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇。
3.根据权利要求2所述的3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇的制备方法,其特征在于第一步中,每1g大苞荆芥加入8ml至10ml乙醇。
4.根据权利要求2或3所述的3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇的制备方法,其特征在于第六步中,高效液相色谱梯度洗脱的洗脱液为甲醇和水的混合液,其中,甲醇和水的体积比为85:15。
5.一种根据权利要求1所述的3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇作为制备预防炎症及抑菌药物的应用。
6.一种根据权利要求1所述的3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇作为制备抗炎及抗菌药物的应用。
7.一种根据权利要求1所述的3,4,4,9,10,10a-六氢-1-羟甲基-7-异丙基-2,4a-二甲基菲-9-醇作为制备防治炎症及抑菌保健品的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111051449.7A CN113943211B (zh) | 2021-09-08 | 2021-09-08 | 维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111051449.7A CN113943211B (zh) | 2021-09-08 | 2021-09-08 | 维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113943211A CN113943211A (zh) | 2022-01-18 |
CN113943211B true CN113943211B (zh) | 2023-08-29 |
Family
ID=79327951
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111051449.7A Active CN113943211B (zh) | 2021-09-08 | 2021-09-08 | 维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113943211B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114805030B (zh) * | 2022-06-07 | 2024-02-13 | 新疆维吾尔自治区中药民族药研究所 | 大苞荆芥提取物中二萜类成分及其制备方法和应用 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5198258A (ja) * | 1975-02-20 | 1976-08-30 | Jiterupenkeijudotainoseizoho | |
JPS5334764A (en) * | 1976-09-09 | 1978-03-31 | Rikagaku Kenkyusho | Preparation of diterpene derivatives and their preparation |
US5965757A (en) * | 1998-02-04 | 1999-10-12 | Boulder Scientific Company | Synthesis of N-silylated cyclopentaphenanthrene compounds |
CN101380406A (zh) * | 2008-10-23 | 2009-03-11 | 中国人民解放军第四军医大学 | 一种用于治疗唇炎的药物及其制备方法 |
CN103393801A (zh) * | 2013-07-31 | 2013-11-20 | 广州市娇兰化妆品有限公司 | 具有祛痤疮功效的中药复方提取物及其制备方法与应用 |
CN104225550A (zh) * | 2014-09-26 | 2014-12-24 | 安徽安科余良卿药业有限公司 | 活血止痛膏的制备方法 |
TWI648253B (zh) * | 2017-11-10 | 2019-01-21 | 義守大學 | 純化奇壬醇的方法 |
CN110507687A (zh) * | 2019-09-16 | 2019-11-29 | 赵谦 | 一种苍耳子二萜类化合物的制备方法及其组合物与应用 |
-
2021
- 2021-09-08 CN CN202111051449.7A patent/CN113943211B/zh active Active
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5198258A (ja) * | 1975-02-20 | 1976-08-30 | Jiterupenkeijudotainoseizoho | |
JPS5334764A (en) * | 1976-09-09 | 1978-03-31 | Rikagaku Kenkyusho | Preparation of diterpene derivatives and their preparation |
US5965757A (en) * | 1998-02-04 | 1999-10-12 | Boulder Scientific Company | Synthesis of N-silylated cyclopentaphenanthrene compounds |
CN101380406A (zh) * | 2008-10-23 | 2009-03-11 | 中国人民解放军第四军医大学 | 一种用于治疗唇炎的药物及其制备方法 |
CN103393801A (zh) * | 2013-07-31 | 2013-11-20 | 广州市娇兰化妆品有限公司 | 具有祛痤疮功效的中药复方提取物及其制备方法与应用 |
CN104225550A (zh) * | 2014-09-26 | 2014-12-24 | 安徽安科余良卿药业有限公司 | 活血止痛膏的制备方法 |
TWI648253B (zh) * | 2017-11-10 | 2019-01-21 | 義守大學 | 純化奇壬醇的方法 |
CN110507687A (zh) * | 2019-09-16 | 2019-11-29 | 赵谦 | 一种苍耳子二萜类化合物的制备方法及其组合物与应用 |
Also Published As
Publication number | Publication date |
---|---|
CN113943211A (zh) | 2022-01-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113861008B (zh) | 大苞松香二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 | |
CN113831245B (zh) | 大苞荆芥提取物中的二萜及其制备方法和应用 | |
CN114044734B (zh) | 松香烷二萜及其制备方法和应用 | |
CN113943211B (zh) | 维吾尔药材中二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 | |
CN108503521B (zh) | 愈创木烷型倍半萜a及其制备方法和作为制备预防肿瘤和抗肿瘤药物的应用 | |
CN113861126B (zh) | 高度氧化二萜及其制备方法和作为制备预防或/和治疗炎症的抗炎、抗菌药物中的应用 | |
CN110218200B (zh) | 一种红树内生真菌中环缩肽化合物及其制备方法与应用 | |
CN111671780A (zh) | 具有神经细胞保护活性的透骨草木脂素制备方法及其应用 | |
CN114933602A (zh) | 白花地胆草中高度氧化的吉玛烷型倍半萜内酯类化合物及其制备方法和应用 | |
CN109369399B (zh) | 1,3-o-二阿魏酸酯-2-甲氧基丙二醇及其制备方法和应用 | |
CN114890870A (zh) | 大苞荆芥提取物中松香烷二萜及其制备方法和应用 | |
CN111253352B (zh) | 一种从中药斑叶兰中提取分离的化合物及其制备方法和应用 | |
CN108299178B (zh) | 愈创木烷型倍半萜b及其制备方法和作为制备预防肿瘤和抗肿瘤药物的应用 | |
CN106349021B (zh) | 一种吉祥草中的化合物及其制备与应用 | |
CN111471050A (zh) | 一类星孢菌素类衍生物及其制备方法和应用 | |
CN105837590A (zh) | 具有抗白色念珠菌活性的化合物及其制备方法和应用 | |
CN115010589B (zh) | 神香草提取物中大苞松香烷二萜类成分及其制备方法和应用 | |
CN115073413B (zh) | 一种苯并环醚类倍半萜类化合物及其制备方法与应用 | |
CN115043719B (zh) | 一种真菌来源的聚酮类化合物及其制备方法与应用 | |
CN115286673B (zh) | 来源于杯叶海绵的降二倍半萜类化合物及提取方法与应用 | |
CN114805030B (zh) | 大苞荆芥提取物中二萜类成分及其制备方法和应用 | |
CN110669032B (zh) | 一类深海真菌来源的聚丙酸酯衍生物及其制备方法和在制备抗结核药物中的应用 | |
CN116064244B (zh) | 一种海洋曲霉菌ITBBc1及其分离的三联苯类化合物和应用 | |
CN116375690B (zh) | 一种黄酮生物碱类化合物及其制备方法和应用 | |
CN114957273B (zh) | 弯萼金丝桃中4种具有抑制群感效应活性的氧杂蒽酮类新化合物及其分离纯化方法和应用 |
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 |