CN114853704A - Pimarane lactone, preparation method and application thereof - Google Patents
Pimarane lactone, preparation method and application thereof Download PDFInfo
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- CN114853704A CN114853704A CN202210674043.2A CN202210674043A CN114853704A CN 114853704 A CN114853704 A CN 114853704A CN 202210674043 A CN202210674043 A CN 202210674043A CN 114853704 A CN114853704 A CN 114853704A
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- -1 Pimarane lactone Chemical class 0.000 title claims abstract description 44
- 229930000776 pimarane Natural products 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 12
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 10
- 230000002000 scavenging effect Effects 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 162
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 32
- 238000004440 column chromatography Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000010828 elution Methods 0.000 claims description 18
- 239000012046 mixed solvent Substances 0.000 claims description 17
- 239000000284 extract Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000287 crude extract Substances 0.000 claims description 10
- 239000003480 eluent Substances 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 10
- 239000000499 gel Substances 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 10
- 229910002027 silica gel Inorganic materials 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000000638 solvent extraction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- 238000010298 pulverizing process Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000013375 chromatographic separation Methods 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 241000982713 Euphorbia fischeriana Species 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 230000000694 effects Effects 0.000 description 12
- 229930004069 diterpene Natural products 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 241001263604 Stellera chamaejasme Species 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 230000002292 Radical scavenging effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 241001088525 Eutypella sp. D-1 Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- JIDXGOZTLODFJW-FEWBMDKSSA-N [(1S,2S,5R,11R,12R,14R)-12-acetyloxy-5-ethenyl-2,9-dihydroxy-5,11-dimethyl-8-oxo-11-tetracyclo[8.5.0.01,14.02,7]pentadeca-6,9-dienyl]methyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC[C@]1(C)[C@@H](C[C@H]2C[C@@]22C1=C(O)C(=O)C1=C[C@](C)(CC[C@]21O)C=C)OC(C)=O JIDXGOZTLODFJW-FEWBMDKSSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000003113 dilution method Methods 0.000 description 2
- 150000004141 diterpene derivatives Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 229930027917 kanamycin Natural products 0.000 description 2
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 2
- 229960000318 kanamycin Drugs 0.000 description 2
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- ZXEVPUOHSXARBR-VIPLHTEESA-N (4ar,10ar,11ar,11br)-4,4,8,11b-tetramethyl-2,3,4a,5,6,10a,11,11a-octahydro-1h-naphtho[2,1-f][1]benzofuran-9-one Chemical compound CC([C@H]1CC2)(C)CCC[C@@]1(C)[C@H]1C2=CC2=C(C)C(=O)O[C@@H]2C1 ZXEVPUOHSXARBR-VIPLHTEESA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 241001048934 Dendrobium albopurpureum Species 0.000 description 1
- 241001076416 Dendrobium tosaense Species 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- 241000434018 Euphorbia pekinensis Species 0.000 description 1
- 241001231225 Eutypella Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001170076 Lonicera macranthoides Species 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 244000237986 Melia azadirachta Species 0.000 description 1
- 235000013500 Melia azadirachta Nutrition 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 241001523965 Xylaria Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000141 anti-hypoxic effect Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- OYXDHOVYZKWSRM-PHJMNMFVSA-N jolkinolide A Chemical compound CC([C@H]1CC2)(C)CCC[C@@]1(C)[C@H]1[C@]32O[C@@H]3C2=C(C)C(=O)OC2=C1 OYXDHOVYZKWSRM-PHJMNMFVSA-N 0.000 description 1
- ZXEVPUOHSXARBR-UHFFFAOYSA-N jolkinolide E Natural products C1CC2C(C)(C)CCCC2(C)C2C1=CC1=C(C)C(=O)OC1C2 ZXEVPUOHSXARBR-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000000274 microglia Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 150000004212 pimarane derivatives Chemical class 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
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- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a pimarane lactone, which is characterized by having the following structure:
the molecular formula of the compound is C 20 H 28 O 3 The molecular weight is 316. The invention also discloses a preparation method of the pimarane lactone, and application of the pimarane lactone in scavenging free radicals or inhibiting the growth of staphylococcus aureus.
Description
Technical Field
The invention belongs to the technical field of natural medicinal chemistry, and particularly relates to a pimarane lactone in stellera chamaejasme, a preparation method thereof, and application of the pimarane lactone in scavenging free radicals or inhibiting the growth of staphylococcus aureus.
Background
The pimarane diterpenoid shows more biological activity. Chenjian army and the like [1] An enantiomer-isopimarane diterpene EP-1 with novel structure and nerve cell protection activity is separated and obtained from Euphorbia pekinensis, and the in vitro activity test result shows that the compound has better nerve cell protection activity. Tri Li [2] And the like, the high-purity pimarane diterpenoid compound is extracted and separated from NaH for the first time, and the compound is found to have anti-inflammatory effect. Storehouse of storehouse (golden storehouse) [3] Isopimarane diterpenoid compounds having anticonvulsant activity and anti-hypoxic activity in myocardial cells are disclosed. Libertellenone H (LH) is a pimarane-type diterpene compound derived from Eutypella sp.D-1, which is an arctic fungus, exhibits significant antitumor activity, and has proliferation inhibitory effect on multiple tumor cells [4] . Old rain, etc [5] Syn-pimarane type (syn-pimarane) diterpene compounds are separated and identified from lonicera macranthoides, and have strong inhibiting effect on agricultural pathogenic fungi. Jiajing et al [6] The prepared pimarane diterpenoid compound has the function of inhibiting the release of inflammation medium NO in BV2 microglia induced by LPS. Liling bell [7] Separating from the dendrobium officinale Kimura et Migo Flickingeria albopurpurea Seidenf to obtain the enantiomorphous pimarane diterpenoid compounds with antibacterial activity. Wanxiaoning, etc [8] Disclosed is a pimarane diterpene which is capable of inhibiting oxidative stress in zebra fish. High female, etc [9] Disclosed is a pimarane diterpene having an excellent phytotoxic activity on the root and leaf sheaths of seedlings of Poa annua. Wu Shaohua et al [10] An antifungal isopimarane diterpene compound is separated from a fermentation product of Azadirachta indica endophytic xylaria YM311647(xylariasp. YM311647). Liujing hall, etc [11] Separating and purifying to obtain Magnaporthe oryzae from thallus fermentation broth extract of Eutypella spA pimarane compound having inhibitory activity.
The pimarane lactone is a diterpene lactone formed by decarboxylation of 16-position carboxyl and 12-position hydroxyl. Jolkinolide A, Jolkinolide E and the like are all pimarane lactone compounds which are separated from the plant Euphorbia fidjiana at the earliest and have no biological activity [12] 。
Free radicals are a factor causing food deterioration, aging of human body, and diseases; the search for compounds that scavenge free radicals is an important direction in medical research.
Reference documents:
[1] chenjiangjun, Wangyuyou, Luyubo, Feng Zi Yu and Gankun are antimer-isopimarane diterpenoids with nerve cell protecting activity, and its preparation method and application [ P ]. CN114349623A,2022-04-15.
[2] Trelliant, chenlong, machao, royal Dajie, Lucui, Zhanghao, Zhang Yu, Sunxuan, Xieli pimaric alkane diterpenoid compound and the preparation method and the application in the preparation of anti-inflammatory drugs [ P ]. CN113582815A,2021-11-02.
[3] A seashore gold storehouse, Wang Yi Min, Zhu Zheng Hua, Qian Da Wei, Wang Ming Gunn, Zhao Ming an isohalapine diterpene compound, its preparation method and application [ P ] CN110204592B,2021-06-22.
[4] Zhang Xiang, ocean source pimarane diterpene Libertellenone H anti-pancreatic cancer activity and mechanism research, doctor, university of military and medicolegal of China's liberation army and military, 2021.
[5] Chenyu, Von warming, Luhui, Xudao, uni-yu, Zhao friendship and Wanggui diterpenoid compound, preparation method and agricultural fungus-resistant application thereof [ P ]. CN108409533B,2021-02-05.
[6] Jasmine, Asaha, Wang Anhua, Huohanshan, a pimarane type diterpenoid, its preparation method and application [ P ]. CN111423310A,2020-07-17.
[7] The separation and identification of 4 enantiomorphous pimpinene diterpene compounds in the plum blossom, the pepper stem, the honey, the zheng liyun, the Zhujiang river flower, the research on the anticaries effect thereof [ J ]. the college of Guangdong pharmaceutical sciences, 2020, v.36; no.157(02) 195-.
[8] Application of kaempferine diterpene in preparation of antioxidant stress medicament [ P ]. CN109908133A,2019-06-21 in Shentao, Lieining, Hanyang, Wantangu and Dongfeng.
[9] Gaokun, Wenwjun and Liya are one kind of antimetabolite diterpene and its preparation process and application [ P ]. CN108840792A,2018-11-20.
[10] Wushahua, Chenge, Miao-Guo-Mali-pini-pine diterpene compound and its application [ P ]. CN103360351B,2015-01-28.
[11] Research on pimarane diterpenoid compounds in the Arctic fungus Eutypella sp.D-1 [ J ]. research and development of natural products, 2014, v.26(01):56-59.
[12]LAL ALLICK R.,CAMBIE RICHARD C.,RUTLEDGE PETER S.,WOODGATE PAUL D.Ent-pimarane and ent-abietane diterpenes from Euphorbia fidjiana[J].Phytochemistry,1990,29(7):2239-2246.
Disclosure of Invention
The first purpose of the invention is to provide a pimarane lactone; the second purpose is to provide a preparation method of the pimarane lactone; the third purpose is to provide the application of the pimarane lactone, which can be used for scavenging free radicals and inhibiting the growth of staphylococcus aureus.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention discloses a pimarane lactone compound, which has the following structure:
the molecular formula is C 20 H 28 O 3 The molecular weight is 316; the English name is: 11 beta-hydroxy-ent-abieta-8 (14),13(15) -dien-16,12 beta-olide; the Chinese names are: stellera chamaejasme lactone A.
The invention discloses a preparation method of pimarane lactone, which takes a stellera chamaejasme medicinal material as a raw material and is prepared by the steps of extract extraction, organic solvent extraction, repeated column chromatography and Sephadex LH-20 gel chromatography separation, and the preparation method specifically comprises the following steps:
(1) extracting the extractum: pulverizing radix Euphorbiae Fischerianae, extracting with a first solvent, and removing the first solvent to obtain crude extract;
(2) organic solvent extraction: suspending the crude extract obtained in the step (1) in water, extracting with a second solvent, and removing the second solvent to obtain a brownish black extract;
(3) column chromatography: dissolving the extract obtained in the step (2) by using a mixed solvent of chloroform and methanol in a volume ratio of 1:1, then adsorbing the extract on silica gel of 300-400 meshes, and filling the extract into a column by a dry method; gradient elution is carried out by using a mixed solvent of chloroform and methanol in a volume ratio of 50:1,20:1,10:1,5:1 and 2: 1; taking the eluent with the ratio of 20:1, and removing the solvent to obtain an elution sample A; dissolving and eluting the sample A by using methanol, adsorbing the sample A on RP-18, performing dry column chromatography, and sequentially eluting by using 40 v/v% methanol, 70 v/v% methanol and 100 v/v% methanol; taking 70 v/v% methanol eluent, and removing the solvent to obtain an elution sample;
(4) column chromatography: dissolving the elution sample obtained in the step (3) by using a mixed solvent (300mL) of chloroform and methanol (volume ratio is 2:1), and adsorbing the sample on 300-400 meshes of silica gel; and (3) filling the column by a dry method, eluting by using petroleum ether and ethyl acetate in a volume ratio of 8:1, and removing the solvent by reduced pressure distillation to obtain a fraction.
(5) Sephadex LH-20 gel chromatographic separation: dissolving the fraction obtained in the step (4) by using a mixed solvent of chloroform and methanol (the volume ratio is 2:1), and passing the solution through a Sephadex LH-20 gel column, wherein the ratio of methanol: and (3) taking dichloromethane with the volume ratio of 2:1 as an eluent, collecting fractions by an automatic collector, identifying components by a TLC plate, recovering the solvent and evaporating to dryness to obtain the pimarane lactone.
Preferably, the first solvent in the step (1) is an ethanol aqueous solution with a volume concentration of 70-100% or a methanol aqueous solution with a volume concentration of 90-100%, and the extraction is heating reflux extraction.
Preferably, the second solvent in step (2) is ethyl acetate.
An example of the method for preparing said pimarane lactone of the present invention is as follows:
(1) extracting the extractum: pulverizing 29.0kg of dried radix Euphorbiae Fischerianae powder, extracting with 95% industrial ethanol under reflux for 3 times (70 deg.C; the industrial ethanol dosage is 35L, 25L, and 20L, respectively, and the extraction time is 4h, 3h, and 3h), distilling under reduced pressure to remove solvent, and mixing the extracts to obtain ethanol crude extract;
(2) organic solvent extraction: suspending the crude extract in water (15.5L), extracting with ethyl acetate for three times (15L each time), and distilling under reduced pressure to remove ethyl acetate to obtain brown black extract 708.97 g;
(3) column chromatography: dissolving 845.97g of methanol extract with a mixed solvent (1.0L) of chloroform and methanol (volume ratio is 2:1), and adsorbing a sample on 300-400 mesh silica gel (1500.0 g); performing dry column chromatography, performing gradient elution with chloroform to methanol (50:1,20:1,10:1,5:1,2:1) at volume ratios of 50L, 50L and 20L, distilling under reduced pressure to remove solvent to obtain corresponding elution samples Fr.1(523.52g), Fr.2(172.22g), Fr.3(77.05g), Fr.4(99.06g) and Fr.5(144.19g), dissolving sample Fr.2(170.0g) in methanol, adsorbing on RP-18, performing dry column chromatography, sequentially eluting with 40% methanol (9.0L), 70% methanol (9.0L) and 100% methanol (5.0L), and distilling under reduced pressure to remove solvent to obtain corresponding elution samples Fr.2a (25.62g), Fr.2b (87.49g) and Fr.2c (34.21 g);
(4) column chromatography: dissolving 87.49g of a sample Fr.2b in a mixed solvent (300mL) of chloroform and methanol (volume ratio of 2:1), and adsorbing the sample on 300-400 mesh silica gel (150.0 g); the column was packed by dry method, and eluted with a mixed solution (10L) of petroleum ether and ethyl acetate at a volume ratio of 8:1 to obtain a fraction, and the solvent was distilled off under reduced pressure to obtain sample Fr.2b12(850.3 mg).
(5) And (3) carrying out Sephadex LH-20 gel chromatographic separation: 840mg of sample Fr.2b12 is taken, dissolved by a mixed solvent (3mL) of chloroform and methanol (volume ratio is 2:1), the obtained solution is put into a Sephadex LH-20 gel column, 600mL of mixed solution of methanol and dichloromethane (2:1, v/v) is used as an eluent, fractions are collected by an automatic collector, 8mL of each tube is used, components are identified by a TLC plate, single components are obtained, and then the obtained components are evaporated to dryness to obtain light yellow powder 15mg, namely the pimarane lactone.
The structure of the pimarane lactone prepared in the above method was determined by the following method:
spectral data are as follows:
compound, light yellow powder, molecular formula:C 20 H 28 O 3 molecular weight: 316.44. ESI-MS of 317.0[ M + H ]] + 。 1 H NMR(600MHz,MeOD)δ6.39(s,1H),4.95(s,1H),4.45(d,J＝3.4,1H),2.62–2.52(m,1H),2.23(s,2H),2.01(d,J＝12.5,1H),1.79(s,2H),1.73–1.62(m,1H),1.58(s,2H),1.47(s,1H),1.40(s,1H),1.36(s,1H),1.31(s,1H),1.29(d,J＝2.5,2H),1.27(d,J＝2.1,1H),0.97(s,3H),0.94(s,3H),0.90(s,3H). 13 C NMR(150MHz,MeOD)δ8.22,17.63,20.12,22.21,24.97,34.39,34.51,38.02,40.59,41.37,42.99,56.84,63.76,65.30,81.34,114.54,118.82,151.50,155.10,178.05。
The compound was identified as: 11 beta-hydroxy-ent-abieta-8 (14),13(15) -dien-16,12 beta-olide; the Chinese names are: stellera chamaejasme lactone A.
The pimarane lactone compound of the invention is subjected to a free radical scavenging test, and the activity is expressed by the capacity of scavenging DPPH free radicals; the activity of scavenging lipid radicals DPPH was determined by setting the sample concentrations to 12.5, 25, 50, 100, 200, and 400. mu. mol/L, respectively. Taking a 96-well culture plate, adding 100 mu L/well of freshly prepared DPPH methanol solution (final concentration is 316 mu mol/L), adding L00 mu L/well of a sample to be detected, adding L00 mu L/well of methanol into a control well, adding 200 mu L of methanol into a blank well, slightly mixing uniformly, sealing the plate by using a sealing plate membrane, standing in a dark place for 30 minutes at room temperature, and measuring the absorbance value of each well on an enzyme-labeled tester, wherein the measurement wavelength is 517 nm; the sample clearance to free radical DPPH was calculated as follows:
wherein A is Blank space : a blank well average absorbance value; a. the Control : mean absorbance values of control wells; a. the Sample (I) : average absorbance values for each concentration sample well.
The samples were tested in triplicate and half the clearance IC was calculated 50 The result was (32.38. + -. 1.92). mu. mol/L, indicating that the pimaranolide compound of the present invention has a good effect of scavenging radicals.
The result of the test on the growth inhibition of staphylococcus aureus of the pimaranolide disclosed by the invention is (25.65 +/-2.37) mu mol/L, which shows that the pimaranolide disclosed by the invention has a better effect of inhibiting the growth of staphylococcus aureus.
Compared with the prior art, the invention has the beneficial effects that:
the invention firstly purifies a pimarane lactone (stellera chamaejasme lactone A) from the medicinal material of the stellera chamaejasme, and the pimarane lactone compound has good functions of eliminating free radicals and inhibiting the growth of staphylococcus aureus and has wide application in the field of medicines.
Drawings
FIG. 1 is the chemical structure of the pimarane lactone of the present invention;
FIG. 2 shows the NMR spectrum of pimaranolide of the present invention (A) 1 H NMR spectrum);
FIG. 3 is a nuclear magnetic resonance carbon spectrum of pimaranolide of the present invention (C 13 C NMR and DEPT spectra);
Detailed Description
The present invention will be described in further detail with reference to examples. It will be appreciated by those skilled in the art that the following examples are illustrative of the invention only and should not be taken as limiting the scope of the invention. Those skilled in the art will recognize that the specific techniques or conditions, not specified in the examples, are according to the techniques or conditions described in the literature of the art or according to the product specification. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available by purchase.
The proportions are volume ratios and concentrations are percent by volume concentrations of the present invention unless otherwise specified.
The pimarane lactone mixture is obtained by separating from a Chinese medicinal material stellera chamaejasme L, and the molecular formula of the pimarane lactone mixture is C 20 H 28 O 3 Molecular weight is 316, having the following structure:
the invention relates to a preparation method of pimarane lactone, which is prepared by using Chinese medicinal material stellera chamaejasme as raw material through the steps of extract extraction, organic solvent extraction, repeated column chromatography and Sephadex LH-20 gel column chromatography; the method specifically comprises the following steps:
A. extracting the extractum: pulverizing 29.0kg of dried radix Euphorbiae Fischerianae powder, extracting with 90 v/v% industrial ethanol under reflux for 3 times (70 deg.C; the industrial ethanol dosage is 35L, 25L, and 20L, respectively, and the extraction time is 4h, 3h, and 3h), distilling under reduced pressure to remove solvent, and mixing to obtain ethanol crude extract;
B. organic solvent extraction: suspending the crude extract in water (15.5L), extracting with ethyl acetate for three times (15L each time), and distilling under reduced pressure to remove ethyl acetate to obtain brown black extract 708.97 g;
C. column chromatography: dissolving 845.97g of methanol extract with a mixed solvent (1.0L) of chloroform and methanol (volume ratio is 2:1), and adsorbing a sample on 300-400 mesh silica gel (1500.0 g); performing dry column chromatography, performing gradient elution with chloroform to methanol (50:1,20:1,10:1,5:1,2:1) at volume ratios of 50L, 50L and 20L, distilling under reduced pressure to remove solvent to obtain corresponding elution samples Fr.1(523.52g), Fr.2(172.22g), Fr.3(77.05g), Fr.4(99.06g) and Fr.5(144.19g), dissolving sample Fr.2(170.0g) in methanol, adsorbing on RP-18, performing dry column chromatography, sequentially eluting with 40% methanol (9.0L), 70% methanol (9.0L) and 100% methanol (5.0L), and distilling under reduced pressure to remove solvent to obtain corresponding elution samples Fr.2a (25.62g), Fr.2b (87.49g) and Fr.2c (34.21 g);
D. column chromatography: dissolving 87.49g of a sample Fr.2b in a mixed solvent (300mL) of chloroform and methanol (volume ratio of 2:1), and adsorbing the sample on 300-400 mesh silica gel (150.0 g); the column was packed by dry method, and eluted with petroleum ether and ethyl acetate (8:1 v/v; 10L) in a volume ratio to give a fraction, which was distilled under reduced pressure to remove the solvent to give Fr.2b12(850.3 mg).
E. Sephadex LH-20 gel chromatographic separation: a840 mg sample Fr.2b12 was taken, dissolved in a mixed solvent (3mL) of chloroform-methanol (volume ratio 2:1), passed through a Sephadex LH-20 gel column, purified by column chromatography with 600mL of methanol: dichloromethane (2:1, v/v) is used as eluent, fractions are collected by an automatic collector, each tube is 8mL, components are identified by a TLC plate, single components are obtained, and then the components are evaporated to dryness to obtain light yellow powder 15mg, namely the pimarane lactone.
Example 1: preparation of pimarane lactones
Pulverizing 29.0kg of dried radix Euphorbiae Fischerianae powder, extracting with 90% ethanol under reflux for 3 times (70 deg.C; each extraction time is 4 hr), distilling under reduced pressure to remove solvent, and mixing the extracts to obtain ethanol crude extract. Suspending the crude extract in water (15.5L), extracting with ethyl acetate (15L × 3), and distilling under reduced pressure to remove ethyl acetate to obtain brown extract 708.97 g; 540.2g of the ethanol extract was dissolved in a mixed solvent (4.0L) of chloroform and methanol (volume ratio 1:1), and the sample was adsorbed on 300-400 mesh silica gel (1.0 kg). The column was packed by a dry method, and gradient elution was carried out with chloroform to methanol (50:1,20:1,10:1,5:1,2:1, volumes of 50L, and 20L, respectively) in a volume ratio, and the solvents were distilled off under reduced pressure to obtain corresponding elution samples Fr.1(523.52g), Fr.2(172.22g), Fr.3(77.05g), Fr.4(99.06g), and Fr.5(144.19 g). Sample Fr.2(170.2g) was dissolved in methanol, adsorbed on RP-18, subjected to dry column chromatography, eluted with 40% methanol (9.0L), 70% methanol (9.0L) and 100% methanol (5.0L) in this order by volume, and the solvent was distilled off under reduced pressure to give corresponding eluted samples Fr.2a (25.62g), Fr.2b (87.49g) and Fr.2c (34.21 g). Taking 70 v/v% methanol eluent to obtain an elution sample Fr.2b (87.49g), dissolving the elution sample Fr.2b in a mixed solvent (300mL) of chloroform and methanol (the volume ratio is 2:1), and adsorbing the sample on silica gel (150.0g) of 300-400 meshes; the column was packed by dry method, and eluted with petroleum ether/ethyl acetate (8:1 v/v; 10L) at a volume ratio to give a fraction, which was then subjected to distillation under reduced pressure to remove the solvent to give Fr.2b12(850.3 mg). A840 mg sample Fr.2b12 was taken, dissolved in a mixed solvent (3mL) of chloroform-methanol (volume ratio 2:1), passed through a Sephadex LH-20 gel column, purified by column chromatography with 600mL of methanol: dichloromethane (2:1, v/v) is used as eluent, fractions are collected by an automatic collector, each tube is 8mL, components are identified by a TLC plate, single components are obtained, and then the components are evaporated to dryness to obtain light yellow powder 15mg, namely the pimarane lactone.
Example 2: detection of the Compound obtained in example 1
The compound obtained in example 1 was detected as a pale yellow powder of formula C 20 H 28 O 3 Molecular weight: 316.44. ESI-MS 317.0[ M + H ]] + 。 1 H NMR(600MHz,MeOD)δ6.39(s,1H),4.95(s,1H),4.45(d,J＝3.4,1H),2.62–2.52(m,1H),2.23(s,2H),2.01(d,J＝12.5,1H),1.79(s,2H),1.73–1.62(m,1H),1.58(s,2H),1.47(s,1H),1.40(s,1H),1.36(s,1H),1.31(s,1H),1.29(d,J＝2.5,2H),1.27(d,J＝2.1,1H),0.97(s,3H),0.94(s,3H),0.90(s,3H). 13 C NMR(150MHz,MeOD)δ8.22,17.63,20.12,22.21,24.97,34.39,34.51,38.02,40.59,41.37,42.99,56.84,63.76,65.30,81.34,114.54,118.82,151.50,155.10,178.05。
The compound was identified as: 11 beta-hydroxy-ent-abieta-8 (14),13(15) -dien-16,12 beta-olide; the Chinese names are: stellera chamaejasme lactone A.
Example 3: radical scavenging Activity test of the Compound obtained in example 1
The compound obtained in example 1 was subjected to a radical scavenging test, and the activity was expressed as the amount of DPPH radical scavenging ability; the activity of scavenging free radical DPPH was determined by setting the sample concentrations to 15, 30, 60, 120, 240, and 480. mu. mol/L, respectively. Taking a 96-well culture plate, respectively adding 100 mu L/well of freshly prepared DPPH methanol solution (final concentration is 316 mu mol/L), adding 00 mu L/well of a sample to be detected, adding 00 mu L/well of methanol into a control well, adding 200 mu L of methanol into a blank well, slightly mixing, sealing the plate by using a sealing plate membrane, standing for 30 minutes in a dark place at room temperature, and measuring the absorbance value of each well on a Bio-Tek enzyme-linked immunosorbent assay instrument, wherein the measurement wavelength is 517 nm; the sample clearance to free radical DPPH was calculated as follows:
wherein A is Blank space : a blank well average absorbance value; a. the Control : mean absorbance values of control wells; a. the Sample (I) : average absorbance values for each concentration sample well.
The samples are parallelly detected for 3 times, and the half clearance concentration IC of the positive control rutin is calculated 50 The result of the measurement was (12.31. + -. 0.04). mu. mol/L, the half-clearing concentration IC of the pimaranolide compound of the present invention 50 As a result, (32.38. + -. 1.92). mu. mol/L.
The result shows that the pimarane lactone compound has better effect of scavenging free radicals.
Example 4: test for inhibition of Staphylococcus aureus growth by the Compound obtained in example 1
According to the report of the literature, the antibacterial activity is tested by adopting a continuous gradient dilution method.
Staphylococcus aureus (Staphylococcus aureus, ATCC 25923) was inoculated into LB medium (1L of water, 10g of tryptone, 5g of yeast extract and 10g of sodium chloride) and cultured for 18 hours. Dissolving a sample to be detected in DMSO (dimethyl sulfoxide), adding the sample into a 96-hole culture plate by adopting a two-fold gradient dilution method to enable the final concentration to be in the range of 0-512 mu g/mL, adding a pre-cultured bacterial liquid diluted to a proper concentration, placing at 37 ℃, culturing for 18h, and observing the growth condition of microorganisms. Kanamycin was used as a positive control and DMSO was used as a negative control. Samples were repeated in triplicate, with the Minimum Inhibitory Concentration (MIC) being the minimum Concentration that inhibits microbial growth. The average MIC for kanamycin was (11.32. + -. 0.15). mu. mol/L, and the average MIC for the pimaralactone compound of the present invention was (25.65. + -. 2.37). mu. mol/L.
The result shows that the pimarane lactone compound has better effect of inhibiting the growth of staphylococcus aureus.
The foregoing shows and describes the general principles, essential features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are described in the specification and illustrated only to illustrate the principle of the present invention, but that various changes and modifications may be made therein without departing from the spirit and scope of the present invention, which fall within the scope of the invention as claimed.
Claims (6)
1. A pimarane lactone, characterized in that it has the following structure:
the molecular formula is C 20 H 28 O 3 The molecular weight is 316.
2. The preparation method of the pimaranthine lactone according to claim 1, wherein the preparation method comprises the following steps of extract extraction, organic solvent extraction, column chromatography and separation and purification by using a euphorbia fischeriana medicinal material as a raw material, and the specific steps are as follows:
(1) extracting the extractum: pulverizing radix Euphorbiae Fischerianae, extracting with a first solvent, and removing the first solvent to obtain crude extract;
(2) organic solvent extraction: suspending the crude extract obtained in the step (1) in water, extracting with a second solvent, and then removing the second solvent to obtain an extract;
(3) column chromatography: dissolving the extract obtained in the step (2) by using a mixed solvent of chloroform and methanol in a volume ratio of 1:1, then adsorbing the extract on 300-400 meshes of silica gel, and filling the column by a dry method; gradient elution is carried out by using a mixed solvent of chloroform and methanol in a volume ratio of 50:1,20:1,10:1,5:1 and 2: 1; taking the eluent with the ratio of 20:1, and removing the solvent to obtain an elution sample A; dissolving and eluting the sample A by using methanol, adsorbing the sample A on RP-18, performing dry column chromatography, and sequentially eluting by using 40 v/v% methanol, 70 v/v% methanol and 100 v/v% methanol; taking 70 v/v% methanol eluent, and removing the solvent to obtain an elution sample;
(4) column chromatography: dissolving the elution sample obtained in the step (3) by using a mixed solvent (300mL) of chloroform and methanol (volume ratio is 2:1), and adsorbing the sample on 300-400 meshes of silica gel; filling the column by a dry method, eluting by mixed liquid of petroleum ether and ethyl acetate with the volume ratio of 8:1, and removing the solvent by reduced pressure distillation to obtain fraction;
(5) sephadex LH-20 gel chromatographic separation: and (3) dissolving the fraction obtained in the step (4) by using a mixed solvent of chloroform and methanol in a volume ratio of 2:1, passing the solution through a Sephadex LH-20 gel column, collecting the fraction by using a mixed solution of methanol and dichloromethane in a volume ratio of 2:1 as an eluent through an automatic collector, identifying components by using a TLC plate, recovering the solvent and evaporating to dryness to obtain the pimarane lactone.
3. The method according to claim 2, wherein the first solvent in step (1) is an ethanol aqueous solution having a volume concentration of 70 to 100% or a methanol aqueous solution having a volume concentration of 90 to 100%, and the extraction is heating reflux extraction.
4. The method according to claim 2, wherein the second solvent in step (2) is ethyl acetate.
5. Use of a pimaranolide according to claim 1 for scavenging free radicals.
6. Use of a pimaranolide according to claim 1 for inhibiting the growth of staphylococcus aureus.
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| US20180353440A1 (en) * | 2017-06-12 | 2018-12-13 | University Of South Carolina | Pimarane Diterpenoids for Use in Wound Healing and Angiogenesis |
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