CN115429786A - Extraction method and application of cadinane sesquiterpene compound - Google Patents
Extraction method and application of cadinane sesquiterpene compound Download PDFInfo
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- CN115429786A CN115429786A CN202210949420.9A CN202210949420A CN115429786A CN 115429786 A CN115429786 A CN 115429786A CN 202210949420 A CN202210949420 A CN 202210949420A CN 115429786 A CN115429786 A CN 115429786A
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- dichloromethane
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- silica gel
- methanol
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- -1 cadinane sesquiterpene compound Chemical class 0.000 title claims abstract description 30
- 238000000605 extraction Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229930004725 sesquiterpene Natural products 0.000 claims abstract description 28
- 239000003814 drug Substances 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 16
- 229940079593 drug Drugs 0.000 claims abstract description 13
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 10
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 7
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 6
- 239000004090 neuroprotective agent Substances 0.000 claims abstract description 5
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 4
- 230000036541 health Effects 0.000 claims abstract description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 claims description 21
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 21
- 238000010828 elution Methods 0.000 claims description 21
- 239000003208 petroleum Substances 0.000 claims description 21
- 239000003480 eluent Substances 0.000 claims description 17
- 238000004809 thin layer chromatography Methods 0.000 claims description 14
- 239000000284 extract Substances 0.000 claims description 10
- 238000001514 detection method Methods 0.000 claims description 8
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 8
- 244000130592 Hibiscus syriacus Species 0.000 claims description 7
- 235000018081 Hibiscus syriacus Nutrition 0.000 claims description 7
- 239000002027 dichloromethane extract Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 238000004262 preparative liquid chromatography Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 238000002386 leaching Methods 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- ITOFWMRNIIFZKF-IVZWLZJFSA-N ac1l4fkl Chemical compound O=C([C@@H](C)C[C@@H]1[C@@H](C(C)C)CC2=O)C3=C1C2=CO3 ITOFWMRNIIFZKF-IVZWLZJFSA-N 0.000 abstract description 34
- 150000004354 sesquiterpene derivatives Chemical class 0.000 abstract description 19
- ITOFWMRNIIFZKF-UHFFFAOYSA-N hibiscone C Natural products O=C1CC(C(C)C)C2CC(C)C(=O)C3=C2C1=CO3 ITOFWMRNIIFZKF-UHFFFAOYSA-N 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 4
- 241000721662 Juniperus Species 0.000 abstract description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 2
- 230000000324 neuroprotective effect Effects 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 5
- 150000004552 cadinane derivatives Chemical class 0.000 description 5
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- 238000003032 molecular docking Methods 0.000 description 4
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 3
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- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 3
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- 229960003692 gamma aminobutyric acid Drugs 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
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- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
- 230000003698 anagen phase Effects 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
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- 238000007796 conventional method Methods 0.000 description 2
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- HRYLQFBHBWLLLL-UHFFFAOYSA-N (+)-costunolide Natural products C1CC(C)=CCCC(C)=CC2OC(=O)C(=C)C21 HRYLQFBHBWLLLL-UHFFFAOYSA-N 0.000 description 1
- CAULGCQHVOVVRN-UHFFFAOYSA-N (3Z,9E)-Germacra-3,7(11),9-trien-6-on Natural products CC(C)=C1CC=C(C)CCC=C(C)CC1=O CAULGCQHVOVVRN-UHFFFAOYSA-N 0.000 description 1
- CAULGCQHVOVVRN-SWZPTJTJSA-N (E,E)-germacrone Chemical compound CC(C)=C1C\C=C(C)\CC\C=C(C)\CC1=O CAULGCQHVOVVRN-SWZPTJTJSA-N 0.000 description 1
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- CUGKULNFZMNVQI-UHFFFAOYSA-N Costunolid I Natural products CC1=CCC=C(/C)CCC2C(C1)OC(=O)C2=C CUGKULNFZMNVQI-UHFFFAOYSA-N 0.000 description 1
- WKSUCCVMYJRMFR-UHFFFAOYSA-N Dehydrocostus lactone Natural products C12OC(=O)C(=C)C2CCC(=C)C2(C)C1(C)C(=C)CC2 WKSUCCVMYJRMFR-UHFFFAOYSA-N 0.000 description 1
- KDPFMRXIVDLQKX-NHFJXKHHSA-N Germacr-1(10)-ene-5,8-dione Chemical compound CC(C)[C@@H]1CC(=O)[C@@H](C)CC\C=C(C)\CC1=O KDPFMRXIVDLQKX-NHFJXKHHSA-N 0.000 description 1
- ZVSZHMFUICOVPY-UHFFFAOYSA-N Germacrone Natural products CC(=C)C1CC=C(/C)CCC=C(/C)CC1=O ZVSZHMFUICOVPY-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
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- 235000006784 Saussurea lappa Nutrition 0.000 description 1
- 244000272264 Saussurea lappa Species 0.000 description 1
- HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 1
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 description 1
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- 241000234299 Zingiberaceae Species 0.000 description 1
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- 230000004913 activation Effects 0.000 description 1
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- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 1
- 229960004191 artemisinin Drugs 0.000 description 1
- 229930101531 artemisinin Natural products 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 101150101280 cort gene Proteins 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- HRYLQFBHBWLLLL-AHNJNIBGSA-N costunolide Chemical compound C1CC(/C)=C/CC\C(C)=C\[C@H]2OC(=O)C(=C)[C@@H]21 HRYLQFBHBWLLLL-AHNJNIBGSA-N 0.000 description 1
- MMTZAJNKISZWFG-UHFFFAOYSA-N costunolide Natural products CC1CCC2C(CC(=C/C=C1)C)OC(=O)C2=C MMTZAJNKISZWFG-UHFFFAOYSA-N 0.000 description 1
- KDPFMRXIVDLQKX-UHFFFAOYSA-N curdione Natural products CC(C)C1CC(=O)C(C)CCC=C(C)CC1=O KDPFMRXIVDLQKX-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- NETSQGRTUNRXEO-XUXIUFHCSA-N dehydrocostus lactone Chemical compound C([C@H]1C(=C)C(=O)O[C@@H]11)CC(=C)[C@H]2[C@@H]1C(=C)CC2 NETSQGRTUNRXEO-XUXIUFHCSA-N 0.000 description 1
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- 238000011534 incubation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
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- 239000013642 negative control Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229930009674 sesquiterpene lactone Natural products 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 208000022679 triple-negative breast carcinoma Diseases 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/20—Hypnotics; Sedatives
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- 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
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Abstract
The invention provides an extraction method and application of cadinane sesquiterpene compounds. The preparation method is simple and quick, and the obtained compound has high purity. The juniper alkane type sesquiterpene compound Hibiscone C provided by the invention not only has good neuroprotective activity, but also has good anti-breast cancer activity, can be applied to the preparation of neuroprotective agents or/and anti-tumor drugs, can be applied to the preparation of drugs for treating neuropsychiatric disorder diseases, drugs for improving sleep and drugs for preventing nervous system diseases or health products, and can also be applied to the preparation of drugs for treating breast cancer.
Description
Technical Field
The invention relates to the field of natural plant medicines, and particularly relates to an extraction method and application of cadinane sesquiterpene compounds.
Background
Sesquiterpenes (sesquiterpenes) refer to natural terpenoids with 15 carbon atoms in the molecule, contain three isoprene units, have various skeleton configurations, and have wide physiological activities. Such as artemisinin in Artemisia annua with antimalarial activity, germacrone and curdione as antitumor physiological active ingredients, costunolide and dehydrocostuslactone as sesquiterpene lactone compounds in saussurea lappa Clarke for inhibiting human hepatitis B surface antigen. Sesquiterpenes are mostly liquid and mainly exist in volatile oil of plants. Their oxygen-containing derivatives, such as alcohols, ketones, and lactones, are also widely present in volatile oils and are the major components of the high boiling point portions of volatile oils. The cadinane sesquiterpene exists widely in plant bodies, is mainly distributed in aromatic plants of Compositae, zingiberaceae, rutaceae, etc., has a small amount of distribution in the agilawood, has strong fragrance and bioactivity, and is an important raw material for the industries of medicine, food and cosmetics. This study is aimed at extracting active ingredients from natural plants and developing new uses.
Disclosure of Invention
In view of the above, the invention provides an extraction method and application of cadinane sesquiterpene compounds.
The technical scheme of the invention is realized as follows:
the extraction method of the cadinane sesquiterpene compound comprises the following steps:
(1) Extracting dry powder of hibiscus syriacus stem with dichloromethane, and concentrating under reduced pressure to obtain dichloromethane extract;
(2) Performing silica gel column chromatography on the extract, and performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 100-0 and dichloromethane-methanol with the volume ratio of 50-1:1 as an eluent to obtain Frs.A-Frs.G;
(3) Performing silica gel column chromatography on the Fr.E component obtained in the step (2), and performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 1:1-5262 and dichloromethane-methanol with the volume ratio of 40;
(4) Performing silica gel column chromatography again on the Fr.E1 obtained in the step (3), and performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 4:1-0:1 and dichloromethane-methanol with the volume ratio of 99-1:1 as an eluent to obtain Fr.E1-1-Fr.E1-9;
(5) Taking Fr.E1-3 obtained in the step (4), performing silica gel column chromatography, and recrystallizing to separate out a target compound; or, using semi-preparative liquid chromatography to perform isocratic purification and separation on Fr.E1-3 obtained in step (4) with SB-phenyl column, 85-95% (v/v) methanol-water to obtain the target compound.
Further, the extraction method of the cadinane sesquiterpene compound comprises the following steps:
(1) Extracting dry powder of hibiscus syriacus stem for 2-4 times at room temperature by using dichloromethane, wherein each extraction time is 60-80h, and the mass-to-volume ratio kg/L of the materials is 1:3.5-4.5; concentrating under reduced pressure to obtain dichloromethane extract to obtain extract;
(2) Performing 100-200-mesh silica gel column chromatography on the extract, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 100-0 and dichloromethane-methanol with the volume ratio of 50-1:1 as eluents, collecting fractions, and performing thin-layer chromatography analysis and detection to obtain 7 components, namely Frs.A-Frs.G in sequence;
(3) Performing 200-300-mesh silica gel column chromatography on the Fr.E component obtained in the step (2), performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 1:1-0:1 and dichloromethane-methanol with the volume ratio of 40-1:1 as an eluent, collecting each fraction, and detecting by thin layer chromatography to obtain 7 components, namely Fr.E1-Fr.E7 in sequence;
(4) Performing column chromatography on Fr.E1 obtained in the step (3) again by using 200-300-mesh silica gel column, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 4:1-0:1 and dichloromethane-methanol with the volume ratio of 99-1:1 as eluent, collecting each fraction, and detecting by using thin layer chromatography to obtain 9 components which are Fr.E1-1-Fr.E1-9 in sequence;
(5) Carrying out silica gel column chromatography on the Fr.E1-3 obtained in the step (4), and recrystallizing to separate out a target compound; or, using semi-preparative liquid chromatography to perform isocratic purification and separation on Fr.E1-3 obtained in step (4) with SB-phenyl column, 85-95% (v/v) methanol-water to obtain the target compound.
Furthermore, the extraction method of the cadinane sesquiterpene compound comprises the following steps:
(1) Leaching dry powder of hibiscus syriacus stem with dichloromethane at room temperature for 3 times, wherein each extraction time is 72h, and the mass-to-volume ratio kg/L of the material is 1:4; concentrating under reduced pressure to obtain dichloromethane extract;
(2) Performing 100-200-mesh silica gel column chromatography on the extract, performing gradient elution by using petroleum ether-dichloromethane in a volume ratio of 100-0, dichloromethane-methanol in a volume ratio of 50-1:1 as an eluent, collecting fractions, and performing thin layer chromatography detection to obtain 7 components which are sequentially Frs.A-Frs.G;
(3) Performing 200-300-mesh silica gel column chromatography on the Fr.E component obtained in the step (2), performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 1:1-0:1 and dichloromethane-methanol with the volume ratio of 40-1:1 as an eluent, collecting each fraction, and detecting by thin layer chromatography to obtain 7 components, namely Fr.E1-Fr.E7 in sequence;
(4) Performing column chromatography on Fr.E1 obtained in the step (3) again by using 200-300-mesh silica gel column, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 4:1-0:1 and dichloromethane-methanol with the volume ratio of 99-1:1 as eluent, collecting each fraction, and detecting by using thin layer chromatography to obtain 9 components which are Fr.E1-1-Fr.E1-9 in sequence;
(5) Carrying out silica gel column chromatography on the Fr.E1-3 obtained in the step (4), and recrystallizing to separate out a target compound; or subjecting Fr.E1-3 obtained in step (4) to semi-preparative liquid chromatography using SB-phenyl column, and isocratic purification and separation with 90% v/v methanol-water to obtain the target compound.
The structural formula of the cadinane sesquiterpene compound obtained by the extraction method is as follows:
the cadinane sesquiterpene compound is applied to preparation of neuroprotective agents or/and antitumor drugs.
Furthermore, the cadinane sesquiterpene compound is applied to preparing medicines for treating neuropsychiatric disorder diseases.
Furthermore, the cadinane sesquiterpene compound is applied to preparing medicines or health products for preventing nervous system diseases.
Furthermore, the cadinane sesquiterpene compound is applied to preparing a sleep improving medicine.
Furthermore, the cadinane sesquiterpene compound is applied to preparing anticancer drugs.
Furthermore, the cadinane sesquiterpene compound is applied to preparing a medicine for treating breast cancer.
Compared with the prior art, the invention has the beneficial effects that:
(1) The extraction method is adopted to obtain the cadinane sesquiterpene compound Hibiscone C, the preparation method is simple and quick, and the obtained compound has high purity.
(2) The juniperane type sesquiterpene compound Hibiscone C extracted by the invention can be used as a small molecular compound, can obviously protect PC12 cell damage induced by corticosterone, and has obvious target activation GABA A The activity of the receptor, the function of improving sleep; the targeting PI3K also has obvious antitumor activity.
(3) By adopting the extraction method, the obtained cadinane sesquiterpene compound Hibiscone C not only has good neuroprotective activity, but also has good anti-breast cancer activity.
(4) The juniperane type sesquiterpene compound Hibiscone C provided by the invention can be applied to preparation of neuroprotective drugs or health care products, can be used for treating neuropsychiatric disturbance diseases and preventing nervous system diseases, and can also be applied to preparation of antitumor drugs, can be used for treating breast cancer and the like.
(5) The juniper alkane type sesquiterpene compound Hibiscone C provided by the invention can be applied to treating patients suffering from mental disorder diseases or breast cancer, and can also be applied to treating patients suffering from mental disorder diseases and breast cancer simultaneously.
Drawings
FIG. 1: of Hibiscone C 1 H NMR(600MHz,CDCl 3 ) A spectrogram;
FIG. 2: of Hibiscone C 13 C NMR(600MHz,CDCl 3 ) A spectrogram;
FIG. 3, mass spectrum [ M + H ] +, of Hibiscone C;
FIG. 4, sesquiterpene chromatography detection method and spectra: detection conditions are as follows: 75% v/v methanol-water, flow rate 2ml/min, detection wavelength 254nm, column: agilent SB-phenyl (5um, 9.4X 250mm)
FIG. 5 shows the juniperane type sesquiterpenes Hibiscone C and GABA A Visual picture of docking (A. Interaction site and overall interaction relationship; B. Interaction pattern picture of docking site)
FIG. 6 is a visual depiction of the docking of juniperane-type sesquiterpene Hibiscone C with PI 3K;
the results of the molecular docking show that the cadinane sesquiterpene Hibiscone C can be specifically combined and activated with GABA A The receptor plays a role in improving sleep and can be stably combined with PI3K to play a remarkable anti-tumor role.
Detailed Description
In order to better understand the technical content of the invention, specific examples are provided below to further illustrate the invention.
The experimental methods used in the examples of the present invention are all conventional methods unless otherwise specified.
The materials, reagents and the like used in the examples of the present invention are commercially available unless otherwise specified.
EXAMPLE 1 preparation of cadinane sesquiterpene Compounds
(1) Extracting 13.0kg of dry powder of stem of hibiscus syriacus with 52L of dichloromethane at room temperature for 3 times, each time for 72h; concentrating under reduced pressure to obtain 405.9g of dichloromethane extract to obtain the extract.
(2) The extract was subjected to column chromatography on 100-200 mesh silica gel, gradient elution with the eluents petroleum ether-dichloromethane (100 to 0, 100 v/v) and dichloromethane-methanol (50.
(3) The fr.e (66.8 g) fractions were column chromatographed using silica gel (200-300 mesh) with a gradient elution of petroleum ether-dichloromethane (1:1-0) and dichloromethane-methanol (40: 1-1, v/v) and combined into 7 fractions, fr.e1-fr.e7, etc., as detected by thin layer chromatography.
(4) E1 was again subjected to column chromatography using silica gel (200-300 mesh), gradient elution with petroleum ether-dichloromethane (4:1-0) and dichloromethane-methanol (99: 1-1, v/v), detected by thin layer chromatography, and combined into 9 components of fr.e1-1-fr.e1-9, etc..
(5) Fr.E1-3 by semi-preparative liquid chromatography, purifying and separating with SB-phenyl column and 90% methanol-water to obtain sesquiterpene (437.7 mg, rt 9.1min), performing silica gel column chromatography on the rest part, and recrystallizing to obtain sesquiterpene 8.4g.
The structure of the sesquiterpene is confirmed by nuclear magnetism, mass spectrum and the like. The structural formula of the sesquiterpene is as follows:
the compound is a cadinane sesquiterpene compound Hibiscone C.
Example 2 protection of sesquiterpenes against Cort induced injury to PC12 cells
Test method 1: PC12 cells were cultured according to a conventional method, and cells in the logarithmic growth phase were seeded in a 96-well plate to give a cell concentration of 5X 10 4 Per mL, 100. Mu.L per well, 5% CO at 37 ℃ 2 The culture box is used for culturing for 24 hours. Setting blank group, model control group, positive control diazepam group and experimental group. Adding 200 μ L incomplete culture medium into blank group without any treatment; model control group was treated with only 200. Mu.L (final concentration of 200. Mu.M) of CORT; the experimental group treated cells with 100. Mu.L (final concentration of 200. Mu.M) CORT and the corresponding drug (50,25,12.5,6.25,3.125,1.5625. Mu.g/mL), diazepam (50,25,12.5,6.25,3.125,1.5625. Mu.g/mL) 100. Mu.L. Placing at 37 ℃ with 5% CO 2 The culture chamber (2) was cultured for 24 hours, 100. Mu.L of the drug-containing medium was carefully aspirated, 10. Mu.L of CCK was added thereto, and the mixture was left at 37 ℃ to contain 5% of CO 2 After incubation for 1-2h in the incubator, the 96-well plate is placed at the 450nm wavelength of a microplate reader to measure the OD value, and the cell survival rate and IC are calculated 50 。
Cell viability (%) = ([ OD (model treated) -OD (blank) ])/([ OD (negative control) -OD (blank) ]) x100%
2, test results: the sesquiterpene component Hibiscone C can remarkably protect PC12 cell injury induced by corticosterone, and has concentration of 1.5625,3.125,6.125,12.5,25,50 μ g/mL, increment rate range of 25-78%, and IC 50 It was 3.49. Mu.g/mL. Diazepam IC 50 The content of the sesquiterpene compound Hibiscortine C is 3.87 mu g/mL, and the result shows that the sesquiterpene compound Hibiscortine C can remarkably protect PC12 cell damage induced by corticosterone and is slightly superior to a positive drug.
Example 2 antitumor Activity assay
Test method 1: recovering, culturing and subculturing the three-negative breast cancer cells to enable the three-negative breast cancer cells to grow to the logarithmic growth phase. The counted cells 5 x10 3 Adding the cells into a 96-well plate at a rate of 100 uL/well, marking the plate cover, and observing whether the cells are uniformly plated under an inverted microscope after the plate cover is added. After observation, the cells were placed in a carbon dioxide incubator (CO) 2 At a concentration of 5% and a temperature of 37 ℃ for 24 hours. A blank control group, a different dose group of the sesquiterpene compound Hibiscone C (1.5625,3.125,6.25,12.5,25,50 mug/mL) and cisplatin (1.25,2.5,5,10 mug/mL) are respectively arranged, and 3 multiple wells are arranged for each concentration. Except for the normal group, the supernatant was discarded and the drugs were added separately, and after further culturing for 24 hours, 100. Mu.L of the supernatant per well was aspirated for use in the detection kit. Adding 10 μ L CCK8 into each well, measuring absorbance at 450nm wavelength after 1 hr, and calculating tumor inhibition rate and IC 50 。
Tumor inhibition rate = (model group OD value-administered group OD value)/model group OD value 100
2, test results: the drug concentration of the sesquiterpene compound Hibiscone C is 1.5625,3.125,6.25,12.5,25,50 mug/mL, the inhibition rate is 26-68 percent, and IC is 50 Respectively 6.47 mug/mL, positive medicine cisplatin anticancer IC 50 It was 3.89. Mu.g/mL. The result shows that the sesquiterpene compound Hibiscone C has obvious activity of inhibiting triple-negative breast cancer.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. The application of the cadinane sesquiterpene compound is characterized in that the cadinane sesquiterpene compound is applied to the preparation of a neuroprotective agent or/and an antitumor drug, and the compound has the structural formula as follows:
2. the use of the cadinan sesquiterpene compound of claim 1 in the preparation of a medicament for the treatment of neuropsychiatric disorders.
3. The use of the cadinan sesquiterpene compound of claim 1 in the preparation of a medicament or health product for the prevention of neurological diseases.
4. Use of the cadinan sesquiterpene compound of claim 1 in the preparation of a sleep-improving drug.
5. The use of the cadinan sesquiterpene compound of claim 1 in the preparation of an anticancer agent.
6. The use of the cadinan sesquiterpene compound of claim 5 in the preparation of a medicament for the treatment of breast cancer.
7. The extraction method of the cadinane sesquiterpene compound is characterized by comprising the following steps:
(1) Extracting dry powder of hibiscus syriacus stem with dichloromethane, and concentrating under reduced pressure to obtain dichloromethane extract;
(2) Performing silica gel column chromatography on the extract, and performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 100-0 and dichloromethane-methanol with the volume ratio of 50-1:1 as an eluent to obtain Frs.A-Frs.G;
(3) Performing silica gel column chromatography on the Fr.E component obtained in the step (2), and performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 1:1-5262 and dichloromethane-methanol with the volume ratio of 40;
(4) Performing silica gel column chromatography again on the Fr.E1 obtained in the step (3), and performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 4:1-0:1 and dichloromethane-methanol with the volume ratio of 99-1:1 as an eluent to obtain Fr.E1-1-Fr.E1-9;
(5) Taking Fr.E1-3 obtained in the step (4), performing silica gel column chromatography, and recrystallizing to separate out a target compound; or, using semi-preparative liquid chromatography to perform isocratic purification and separation on Fr.E1-3 obtained in step (4) by using an SB-phenyl chromatographic column, 85-95% v/v methanol-water, and preparing the target compound, wherein the compound has the following structural formula:
8. the method for extracting cadinan sesquiterpene compounds according to claim 7, comprising the following steps:
(1) Leaching dry powder of hibiscus syriacus stem for 2-4 times at room temperature by using dichloromethane, wherein each time of extraction is 60-80h, and the mass volume ratio kg/L of materials is 1:3.5-4.5; concentrating under reduced pressure to obtain dichloromethane extract to obtain extract;
(2) Performing 100-200-mesh silica gel column chromatography on the extract, performing gradient elution by using petroleum ether-dichloromethane in a volume ratio of 100-0 and dichloromethane-methanol in a volume ratio of 50-1:1 as eluents, collecting fractions, and performing thin layer chromatography detection to obtain 7 components which are sequentially Frs.A-Frs.G;
(3) Performing 200-300-mesh silica gel column chromatography on the Fr.E component obtained in the step (2), performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 1:1-0:1 and dichloromethane-methanol with the volume ratio of 40-1:1 as an eluent, collecting each fraction, and detecting by thin layer chromatography to obtain 7 components, namely Fr.E1-Fr.E7 in sequence;
(4) Performing silica gel column chromatography on the Fr.E1 obtained in the step (3) again by using 200-300 meshes, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 4:1-0:1 and dichloromethane-methanol with the volume ratio of 99-1:1 as eluent, collecting each fraction, and detecting by using thin layer chromatography to obtain 9 components which are Fr.E1-1-Fr.E1-9 in sequence;
(5) Taking Fr.E1-3 obtained in the step (4), performing silica gel column chromatography, and recrystallizing to separate out a target compound; or, using semi-preparative liquid chromatography to perform isocratic purification and separation on Fr.E1-3 obtained in step (4) with SB-phenyl column, 85-95% (v/v) methanol-water to obtain the target compound.
9. The method for extracting cadinan sesquiterpene compounds according to claim 8, comprising the following steps:
(1) Leaching dry powder of hibiscus syriacus stem with dichloromethane at room temperature for 3 times, wherein each extraction time is 72h, and the mass-to-volume ratio kg/L of the material is 1:4; concentrating under reduced pressure to obtain dichloromethane extract;
(2) Performing 100-200-mesh silica gel column chromatography on the extract, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 100 to 0 and dichloromethane-methanol with the volume ratio of 50 to 1:1 as an eluent, collecting each fraction, and performing thin-layer chromatography analysis and detection to obtain 7 components, namely Frs.A-Frs.G in sequence;
(3) Performing silica gel column chromatography on the Fr.E component obtained in the step (2) by using 200-300 meshes of silica gel column chromatography, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 1:1-0:1 and dichloromethane-methanol with the volume ratio of 40-1:1 as an eluent, collecting each fraction, and detecting by thin layer chromatography to obtain 7 components which are Fr.E1-Fr.E7 in sequence;
(4) Performing column chromatography on Fr.E1 obtained in the step (3) again by using 200-300-mesh silica gel column, performing gradient elution by using petroleum ether-dichloromethane with the volume ratio of 4:1-0:1 and dichloromethane-methanol with the volume ratio of 99-1:1 as eluent, collecting each fraction, and detecting by using thin layer chromatography to obtain 9 components which are Fr.E1-1-Fr.E1-9 in sequence;
(5) Taking Fr.E1-3 obtained in the step (4), performing silica gel column chromatography, and recrystallizing to separate out a target compound; or, using semi-preparative liquid chromatography to perform isocratic purification and separation on Fr.E1-3 obtained in step (4) by using SB-phenyl chromatographic column and 90% v/v methanol-water to obtain the target compound.
10. Use of the cadinane sesquiterpene compound obtained by the extraction method of any one of claims 7-9 in the preparation of neuroprotective agents and/or antitumor drugs.
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| CN110522776A (en) * | 2019-09-26 | 2019-12-03 | 中国医学科学院药用植物研究所 | It is a kind of Huang the rose of Sharon in anti-tumor effective component preparation method and application |
| CN114436802A (en) * | 2022-01-17 | 2022-05-06 | 中国医学科学院药用植物研究所海南分所 | Cadinane sesquiterpene compound and preparation method and application thereof |
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