CN116730957B - Linderane type sesquiterpene dimer and preparation method and application thereof - Google Patents
Linderane type sesquiterpene dimer and preparation method and application thereof Download PDFInfo
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- KBMSVODXFLAQNJ-DXGHHDSJSA-N Linderane Chemical compound C1=2C(C)=COC=2C\C(C)=C\CC[C@@]23C(=O)O[C@@H]1[C@@H]2O3 KBMSVODXFLAQNJ-DXGHHDSJSA-N 0.000 title claims abstract description 12
- 229930003839 sesquiterpene dimer Natural products 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- KBMSVODXFLAQNJ-ZEBDJQDSSA-N Linderane Natural products O=C1O[C@@H]2[C@@H]3O[C@]13CC/C=C(/C)\Cc1occ(C)c21 KBMSVODXFLAQNJ-ZEBDJQDSSA-N 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000003208 petroleum Substances 0.000 claims description 14
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 10
- 238000010829 isocratic elution Methods 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 7
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 6
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 230000014759 maintenance of location Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000010298 pulverizing process Methods 0.000 claims description 3
- 238000004019 gradient elution chromatography Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000007689 inspection Methods 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 30
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 12
- 241000546273 Lindera <angiosperm> Species 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 7
- 241000218195 Lauraceae Species 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 6
- 239000002158 endotoxin Substances 0.000 abstract description 4
- 229920006008 lipopolysaccharide Polymers 0.000 abstract description 4
- 229930014626 natural product Natural products 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 238000002474 experimental method Methods 0.000 abstract description 2
- 241000009298 Trigla lyra Species 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 235000008671 Calycanthus floridus Nutrition 0.000 description 6
- 235000008670 Calycanthus occidentalis Nutrition 0.000 description 6
- 244000148992 Lindera benzoin Species 0.000 description 6
- 235000004520 Lindera benzoin Nutrition 0.000 description 6
- 235000008262 Lindera benzoin var. benzoin Nutrition 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000722363 Piper Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 238000005100 correlation spectroscopy Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000000469 ethanolic extract Substances 0.000 description 2
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 229930004725 sesquiterpene Natural products 0.000 description 2
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 235000008496 Drimys aromatica Nutrition 0.000 description 1
- 208000008967 Enuresis Diseases 0.000 description 1
- 206010049077 Hernia pain Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 240000002262 Litsea cubeba Species 0.000 description 1
- 235000012854 Litsea cubeba Nutrition 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000019790 abdominal distention Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000012930 cell culture fluid Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002074 deregulated effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to the technical field of medicines, relates to a linderane type sesquiterpene dimer, a preparation method and application thereof, and in particular relates to a lindera root of lindera genus plant of Lauraceae family from traditional Chinese medicineLinderaaggregata) A linderane sesquiterpene dimer obtained by separation, and a preparation method and application thereof. The compound is isolated from lindera root of Piper genus of Lauraceae familyLinderaaggregata) Is designated as Aggreganoid H. The preparation method of the compound adopts a mature technical means in the field of natural product chemistry, and is easy to realize in actual operation. Biological activity experiments show that Aggreganoid H can obviously inhibit lipopolysaccharide-induced RAW264.7 cells from releasing nitric oxide, and IC thereof 50 37.35.+ -. 1.57. Mu.M.
Description
Technical Field
The invention relates to the technical field of medicines, in particular to a combined spicebush root of mountain pepper genus in Lauraceae family which is a traditional Chinese medicineLinderaaggregata) A linderane sesquiterpene dimer obtained by separation, and a preparation method and application thereof.
Background
Inflammation is a defensive reaction of organisms under harmful stimuli such as wounds, infection and the like, and is beneficial to the identification and elimination of inflammatory factors by the organisms. However, when the immune balance is deregulated, the body's response to inflammatory factors is reduced or increased, which may cause various diseases such as immunodeficiency diseases, allergic diseases, cardiovascular diseases, etc. At present, the main medicines for clinically treating inflammation comprise steroidal anti-inflammatory medicines and non-steroidal anti-inflammatory medicines, and the clinical application of the medicines is limited due to a plurality of adverse reactions, single target points and the like of the medicines. Therefore, the search for high-efficiency and low-toxicity anti-inflammatory drugs has great significance. The plant source natural product is an important source of anti-inflammatory drugs, and has the characteristics of various structures and activities, wide action targets, small toxic and side effects and the like.
Radix LinderaeLinderaaggregata) Is a plant of the genus Piper of the family Lauraceae, which is the only variety of combined spicebush root recorded in the Chinese pharmacopoeia of 2020 edition, and has a long history of use. This herb is pungent and warm. It has effects in promoting qi circulation, relieving pain, warming kidney, and dispelling cold, and can be used for treating stagnation of qi due to congealing cold, chest and abdominal distention, asthma, bladder deficiency cold, enuresis, frequent urination, hernia pain, and cold channel abdominal pain.
Disclosure of Invention
The invention aims to provide a linderane sesquiterpene dimer, and also provides a preparation method and application thereof in the aspect of treating alcohol oxidation injury.
A linderane sesquiterpene dimer is named as Aggreganoid H, and has a chemical structural formula shown in formula I:
。
the invention also provides a preparation method of the linderane sesquiterpene dimer, which comprises the following steps:
(1) Pulverizing dried radix Linderae, heating and reflux-extracting with ethanol, filtering, mixing extractive solutions, concentrating under reduced pressure, and recovering ethanol to obtain total extract;
(2) Dispersing the total extract in the step (1) in water, and then extracting with equal volume petroleum ether to obtain petroleum ether phase extract;
(3) Subjecting the extract obtained in the step (2) to silica gel column chromatography, petroleum ether-acetone gradient elution and thin-layer chromatography inspection to obtain seven components A-G, subjecting component F to reversed-phase C-18 column chromatography methanol-water gradient elution, and subjecting the component F to reversed-phase C-8 acetonitrile-water isocratic elution and reversed-phase C-18 methanol-water isocratic elution respectively, wherein a chromatographic peak with a retention time of 13.25 min is Aggreganoid H;
in the petroleum ether-acetone gradient elution process of the step (3), the volume ratio of petroleum ether to acetone is 100:0 to 0:100.
In the methanol-water gradient elution of the step (3), the volume ratio of the methanol to the water is 20:80 to 100:0.
The volume ratio of acetonitrile and water of the acetonitrile-water isocratic elution in the step (3) is 60:40; the volume ratio of methanol to water for methanol-water isocratic elution was 65:35.
The invention also provides application of the compound in preparing anti-inflammatory medicaments.
The invention has the beneficial effects that:
1. new compounds
According to the invention, 1 linderane sesquiterpene dimer with a novel structure is separated from dried root tuber of lindera root of lindera genus of Lauraceae family, the compound is a dimer compound with a C32 skeleton formed by connecting two lindera sesquiterpenes through a 1, 1-disubstituted ethyl bridge, and most lindera sesquiterpenes are C30 skeletons, and the structure is rare in the natural world. The invention enriches the research of chemical component diversity of the combined spicebush root, adds 1 new compound for the field of natural compounds, and also provides a new reference for the research of chemical taxonomy of the combined spicebush root.
2. The extraction method is simple
The preparation method of the compound adopts a mature technical means in the field of natural product chemistry, and is easy to realize in actual operation.
3. Anti-inflammatory Activity
In vitro bioactivity experiments show that Aggreganoid H can remarkably inhibit lipopolysaccharide-induced mouse macrophage (RAW 264.7) from releasing nitric oxide, and IC thereof 50 37.35.+ -. 1.57. Mu.M.
Drawings
High resolution mass spectra of compound Aggreganoid H of fig. 1;
FIG. 2 hydrogen spectrum of Aggreganoid H;
FIG. 3 carbon spectrum of Aggreganoid H;
FIG. 4 Compound Aggreganoid H 1 H- 1 H COSY profile;
FIG. 5 HSQC spectrum of Aggreganoid H;
FIG. 6 HMBC spectra of Aggreganoid H;
FIG. 7 NOESY spectrum of Aggreganoid H;
FIG. 8 ultraviolet absorbance spectra of Aggreganoid H;
FIG. 9 an infrared spectrum of compound Aggreganoid H;
FIG. 10 high performance liquid chromatograms of Aggreganoid H and Aggreganoid G.
Detailed Description
Example 1 preparation of Aggreganoid H
Extracting: pulverizing dried root tuber of Lindera root (5.0 kg) of Piper genus of Lauraceae family, reflux-extracting with 80% ethanol for 4 times (1-2 hr each time), filtering, mixing extractive solutions, concentrating under reduced pressure, diluting the concentrated extractive solution with water, extracting with petroleum ether of equal volume for 4 times, and recovering solvent under reduced pressure to obtain petroleum ether phase extract.
Separating: subjecting the petroleum ether phase extract (127.5, g) obtained in the previous step to silica gel column chromatography, gradient eluting with petroleum ether-acetone (100:0 to 0:100) in volume ratio, gradient eluting with reversed phase C18 silica gel column chromatography methanol-water (20:80 to 100:0), separating acetonitrile-water (60:40) by semi-preparative high performance liquid chromatography C8 column, and separating methanol-water (65:35) by semi-preparative high performance liquid chromatography C18 column to obtain Aggreganoid H (3.5, mg).
Aggreganoid H
Ultraviolet spectrum (methanol):λ max (logε) 195 (4.09), 275 (2.98), see FIG. 8;
an infrared spectrum of light is obtained,ν max 3444, 2930, 2361, 2314, 1740, 1524, 1057 cm -1 see fig. 9;
FIG. 2 is a hydrogen spectrum of compound Aggreganoid H; FIG. 3 is a carbon spectrum of compound Aggreganoid H; FIG. 4 is a compound Aggreganoid H 1 H- 1 H COSY profile; FIG. 5 is the HSQC spectrum of compound Aggreganoid H; FIG. 6 is a schematic diagram of a chemical processHMBC profile of compound Aggreganoid H; FIG. 7 is a NOESY spectrum of compound Aggreganoid H; after the data are collated, the results are shown in Table 1, in which high resolution mass spectra are shownm/z487.2841 [M + H] + (calculated value is C 32 H 39 O 4 , 487.2848)。
Table 1 Nuclear magnetic data for Aggreganoid H (deuterated chloroform)
Example 2 in vitro bioactivity assay
Cell culture: taking RAW264.7 cells in logarithmic growth phase, diluting into 2×10 with DEME high sugar complete medium 5 Each/mL of the cell suspension was inoculated into 96-cell culture plates at 100. Mu.L per well. Is placed at 37 o C. Culturing in a 5% carbon dioxide incubator for 24 hours. The test compounds were formulated in a series of different concentrations (20 to 200. Mu. Mol/L) using DEME high sugar complete medium by double dilution, with 3 duplicate wells set for each concentration. After 1 hour of the test compound acting on the cells, lipopolysaccharide with a final concentration of 1 μg/mL is added; then 37 o After C inoculation for 24 hours, the nitric oxide concentration of the supernatant of the cell culture fluid is measured by adopting a Griess method, and the inhibition rate of the compound on nitric oxide release of RAW264.7 cells is calculated. Half-maximal effective Inhibitory Concentration (IC) of compounds to inhibit nitric oxide release from RAW264.7 cells was calculated using Graphpad Prism 8 software 50 ). The results show that Aggreganoid H can obviously inhibit lipopolysaccharide-induced RAW264.7 cells from releasing nitric oxide, and IC (integrated circuit) thereof 50 37.35.+ -. 1.57. Mu.M.
Example 3 differs from the compound Aggreganoid G disclosed in the earlier application, patent CN 115850218A
The compounds Aggregaroid H and Aggregaroid G are novel compounds separated from the ethanol extract of the combined spicebush root, and the structures of the two compounds are very similar, wherein the difference is that the Aggregaroid H is replaced by one methyl more than the Aggregaroid G. Since the structures of the two compounds are very similar, the polarity of the two compounds is also substantially the same. Thus, in the separation process of the ethanol extract of the combined spicebush root, the separation conditions of the two compounds are basically consistent. The separation process of the two is as follows: after the compounds Aggreganoid H and Aggreganoid G are subjected to reversed-phase C-18 column chromatography methanol-water gradient elution (the volume ratio of methanol to water is 20:80 to 100:0), respectively subjected to reversed-phase C-8 acetonitrile-water isocratic elution (the volume ratio of acetonitrile to water is 60:40) and reversed-phase C-18 methanol-water isocratic elution (the volume ratio of methanol to water is 65:35); as shown in the chromatogram of FIG. 10, the chromatographic peak with retention time of 11.97 min was Aggreganoid G, while the chromatographic peak with retention time of 13.25 min was Aggreganoid H, and the two compounds could achieve better separation.
Claims (3)
1. A linderane sesquiterpene dimer is named as Aggreganoid H, and is characterized in that the chemical structural formula is shown as formula I:。
2. a method for preparing the linderane sesquiterpene dimer according to claim 1, which comprises the following steps:
(1) Pulverizing dried radix Linderae, heating and reflux-extracting with ethanol, filtering, mixing extractive solutions, concentrating under reduced pressure, and recovering ethanol to obtain total extract;
(2) Dispersing the total extract in the step (1) in water, and then extracting with equal volume petroleum ether to obtain petroleum ether phase extract;
(3) Subjecting the extract obtained in the step (2) to silica gel column chromatography, petroleum ether-acetone gradient elution and thin-layer chromatography inspection to obtain seven components A-G, subjecting the component F to reversed-phase C-18 column chromatography and methanol-water gradient elution, and subjecting the component F to reversed-phase C-8 acetonitrile-water isocratic elution and reversed-phase C-18 methanol-water isocratic elution respectively, wherein a chromatographic peak with a retention time of 13.25 min is Aggreganoid H;
in the petroleum ether-acetone gradient elution process of the step (3), the volume ratio of petroleum ether to acetone is 100:0 to 0:100;
in the methanol-water gradient elution of the step (3), the volume ratio of the methanol to the water is 20:80 to 100:0;
the volume ratio of acetonitrile and water of the acetonitrile-water isocratic elution in the step (3) is 60:40; the volume ratio of methanol to water for methanol-water isocratic elution was 65:35.
3. Use of a linderane sesquiterpene dimer according to claim 1 for the preparation of a medicament for the treatment of inflammation.
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| CN109384798A (en) * | 2018-12-07 | 2019-02-26 | 上海健康医学院 | A kind of lindenrane sesquiterpene dimers and its preparation method and application with 1,3- dioxolane connection unit |
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| CN114057764A (en) * | 2021-12-07 | 2022-02-18 | 中国科学院昆明植物研究所 | Lindane dimeric sesquiterpene with anti-inflammatory activity and preparation method and application thereof |
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| CN115850218A (en) * | 2023-01-09 | 2023-03-28 | 山东大学 | Linderane type sesquiterpene dimer and preparation method and application thereof |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109384798A (en) * | 2018-12-07 | 2019-02-26 | 上海健康医学院 | A kind of lindenrane sesquiterpene dimers and its preparation method and application with 1,3- dioxolane connection unit |
| CN110734419A (en) * | 2019-10-28 | 2020-01-31 | 山东省食品药品检验研究院 | eudesmane type sesquiterpene geranylhomogentisate heterocomplex and preparation method and application thereof |
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| CN115850218A (en) * | 2023-01-09 | 2023-03-28 | 山东大学 | Linderane type sesquiterpene dimer and preparation method and application thereof |
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