CN117486900A - Heteroterpene compound and preparation method and application thereof - Google Patents
Heteroterpene compound and preparation method and application thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 241000233866 Fungi Species 0.000 claims abstract description 20
- 241000208340 Araliaceae Species 0.000 claims abstract description 17
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims abstract description 17
- 235000003140 Panax quinquefolius Nutrition 0.000 claims abstract description 17
- 235000008434 ginseng Nutrition 0.000 claims abstract description 17
- 239000000284 extract Substances 0.000 claims abstract description 14
- 238000010828 elution Methods 0.000 claims abstract description 10
- -1 hetero terpene compound Chemical class 0.000 claims abstract description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000287 crude extract Substances 0.000 claims abstract description 8
- 238000002386 leaching Methods 0.000 claims abstract description 8
- 239000000741 silica gel Substances 0.000 claims abstract description 8
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 4
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 4
- 239000000499 gel Substances 0.000 claims abstract description 4
- 239000008103 glucose Substances 0.000 claims abstract description 4
- 235000007586 terpenes Nutrition 0.000 claims abstract description 3
- 238000004440 column chromatography Methods 0.000 claims abstract 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 5
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 7
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 description 14
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- 229920006008 lipopolysaccharide Polymers 0.000 description 12
- 206010061218 Inflammation Diseases 0.000 description 9
- 230000004054 inflammatory process Effects 0.000 description 9
- 210000002540 macrophage Anatomy 0.000 description 8
- 230000002757 inflammatory effect Effects 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 3
- 239000002260 anti-inflammatory agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 230000003698 anagen phase Effects 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
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- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
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- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 241000235058 Komagataella pastoris Species 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 102000008934 Muscle Proteins Human genes 0.000 description 1
- 108010074084 Muscle Proteins Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000007443 Neurasthenia Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010061481 Renal injury Diseases 0.000 description 1
- 208000032140 Sleepiness Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 208000009205 Tinnitus Diseases 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
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- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
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- 239000012156 elution solvent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000004377 improving vision Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 208000037806 kidney injury Diseases 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000017095 negative regulation of cell growth Effects 0.000 description 1
- 206010029410 night sweats Diseases 0.000 description 1
- 230000036565 night sweats Effects 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/20—Spiro-condensed 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
Landscapes
- 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)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a hetero-terpenoid, a preparation method and application thereof, wherein the molecular formula of the hetero-terpenoid is as follows: c (C) 26 H 26 N 2 O 5 . The preparation method of the hetero-terpenoid comprises the following steps: s1, leaching white ginseng fungus fruiting bodies with methanol, concentrating the extract to obtain an extract, and extracting the extract with ethyl acetate to obtain an ethyl acetate crude extract; s2, separating the ethyl acetate crude extract by silica gel normal phase chromatography, and then performing gradient elution to obtain 8 components (Fr.1-Fr.8) with the polarity from small to large; s3, subjecting the component Fr.2 to column chromatography of glucose gel and using methylene chloride: separating by using an eluting solvent with methanol of 1:1, and continuing to elute dichloromethane with the polarity of: methanol and ethyl acetate: separating with silica gel column of methanol to obtain pure hetero terpene compound. The compound has remarkable inhibitory activity on NO production induced by LPS, and IC thereof 50 25.2 mu M has clinical application potential of anti-inflammatory treatment and can be used for preparing anti-inflammatory medicaments.
Description
Technical Field
The invention relates to the field of pharmaceutical compounds, in particular to a highly oxidized hetero-terpenoid from white ginseng fungus, a preparation method thereof and application thereof in preparing anti-inflammatory drugs.
Background
Inflammation is a defensive response of the body to various inflammatory factors and plays an important role in the immune response. The occurrence of inflammation in local tissues produces a series of complex changes, clinically manifested as redness, swelling, fever, pain and dysfunction, and the inflammation can cause systemic reactions including fever, somnolence, acceleration of muscle protein degradation, etc. Inflammation is also an important factor in the aging process of the human body, and is closely related to many chronic diseases such as arthritis, cardiovascular diseases, cancer, osteoporosis, asthma, alzheimer's disease, dementia, obesity, type II diabetes, and the like. Currently, the prevailing pathogenesis of inflammation is thought to be that macrophages and their released mediators of inflammation are critical in initiating inflammation. Macrophages are an important immune cell in the body, are the main cells that initiate the production of inflammatory mediators in the body, and have anti-infective, anti-tumor and immunomodulating effects. Macrophages can be activated by a variety of inflammatory factors such as cytokines, bacterial lipopolysaccharide LPS, extracellular matrix proteins, and other chemical mediators. LPS is a very important inflammatory factor that stimulates macrophages to synthesize and release a variety of endogenous active factors in the body, thereby inducing inflammation. The use of LPS to treat macrophages is a common in vitro model modeling approach for inflammation.
The anti-inflammatory agents currently in common clinical use mainly include non-steroidal anti-inflammatory agents and steroidal anti-inflammatory agents. Although both of these anti-inflammatory agents have some clinical anti-inflammatory effects, a number of adverse effects and tolerability such as gastric mucosal injury, liver injury, kidney injury, etc. can occur with prolonged use in large amounts. Therefore, searching and developing safer and more efficient anti-inflammatory drugs is a hotspot in the field of anti-inflammatory drug research.
The white ginseng fungus is a rare mushroom fungus used as both medicine and food, and is generally eaten as a health care product in Asia. In the traditional Chinese medicine, the Chinese medicine has the effects of clearing liver and improving vision, nourishing and strengthening body, and has obvious curative effects on children night sweat, neurasthenia, dizziness and tinnitus, gynecological diseases and the like. Researches report that polysaccharide compounds separated from the white ginseng fungus water extract have anti-tumor, anti-inflammatory, antibacterial and other activities. These polysaccharide compounds can significantly inhibit the production of NO by macrophages and down-regulate the expression of the inflammatory factor nucleic factor-kappa (NF- κB). Therefore, the development of novel anti-inflammatory drugs by excavating organic molecules in the white ginseng fungus organic extract has important medicinal and economic values.
Disclosure of Invention
The invention aims to provide a highly oxidized hetero-terpenoid from white ginseng fungus.
Another object of the present invention is to provide a method for preparing highly oxidized hetero terpenoids derived from the above-mentioned white ginseng fungus.
Another object of the present invention is to provide the use of highly oxidized diterpenoid compounds derived from the above-mentioned white ginseng fungus in the preparation of anti-inflammatory drugs.
The technical scheme of the invention is as follows: a heteroterpenoid having the general structural formula:
the molecular formula is: c (C) 26 H 26 N 2 O 5 。
The hetero-terpenoid is separated from fresh fruiting bodies of the white ginseng fungus, which are provided by the industrial scientific and technological company of the agricultural fungus of Pichia pastoris.
A method for preparing a hetero-terpenoid, the method comprising the steps of:
s1, leaching white ginseng fungus fruiting bodies with methanol, concentrating the extract to obtain an extract, and extracting the extract with ethyl acetate to obtain an ethyl acetate crude extract;
s2, separating the ethyl acetate crude extract by silica gel normal phase chromatography, and then performing gradient elution to obtain 8 components (Fr.1-Fr.8) with the polarity from small to large;
s3, the component Fr.2 is treated with glucose gel (Sephadex TM LH-20) and with dichloromethane:
separating by using an eluting solvent with methanol of 1:1, and continuing to elute dichloromethane with the polarity of:
methanol (v/v; 60:1) and ethyl acetate: separating with silica gel chromatographic column of methanol (v/v; 90:1) to obtain pure hetero terpene compound.
In the step S1, the leaching times of methanol are 2-5 times, and the leaching time of one time is 10 days.
In the step S2, the solvent adopted in gradient elution is petroleum ether/ethyl acetate, and 10% -80% ethyl acetate/petroleum ether part is collected after elution.
The application of the hetero-terpenoid can be used for preparing anti-inflammatory drugs.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a hetero-terpenoid from white ginseng fungus, which has obvious inhibition activity on NO generation induced by LPS (LPS), and IC (integrated circuit) 50 25.2 mu M can be used for preparing anti-inflammatory drugs. Therefore, the hetero-terpenoid provided by the invention has clinical application potential of anti-inflammatory treatment.
Detailed Description
The invention is further illustrated in detail below in connection with specific examples which are provided solely for the purpose of illustration and are not intended to limit the scope of the invention. The test methods used in the following examples are conventional methods unless otherwise specified; the materials, reagents and the like used, unless otherwise specified, are those commercially available.
Example 1
A preparation method of a hetero-terpenoid from white ginseng fungus, wherein the hetero-terpenoid is separated from fresh fruiting body of white ginseng fungus; the fresh fruiting body of the white ginseng fungus is provided by the technology-limited liability company of the agricultural fungus industry in the Pijie city.
A specific preparation method of the hetero-terpenoid comprises the following steps:
s1, leaching the white ginseng fungus fruiting body for multiple times by using methanol, concentrating the extract to obtain an extract, and extracting the extract by using ethyl acetate to obtain an ethyl acetate crude extract.
S2, separating the ethyl acetate crude extract by silica gel normal phase chromatography; gradient elution is carried out by petroleum ether/ethyl acetate to obtain 8 components (Fr.1-Fr.8) with the polarity from small to large.
S3, the component Fr.2 is treated with glucose gel (Sephadex TM LH-20) and with dichloromethane: the elution solvent with methanol at 1:1 was used for separation. After the elution is finished, the elution polarity is dichloromethane: methanol (v/v; 60:1)And ethyl acetate: silica gel chromatographic column separation of methanol (v/v; 90:1) to obtain pure compound I.
Example 2
And (3) carrying out structural test analysis on the novel compound I to obtain the following experimental data:
new compounds I, C 26 H 26 N 2 O 5 ，HRESI-MS：469.1736[M+H] + (calculated 469.1734) Table 1 NMR data of Compound I (CDCl) 3 ，500MHz/125MHz,ppm)
From the data in table 1, it was confirmed that the structural formula of the novel compound I is as follows:
example 3
Anti-inflammatory cell screening model of Compound I
1. Cell culture and treatment
RAW 264.7 cells (Shanghai institute of biochemistry and cell biology cell bank) were cultured in vitro, and conventional maintenance culture and passage were performed using DMEM high sugar medium containing 10% FBS at 37 ℃ and 5% carbon dioxide concentration.
2. Intervention of compounds
(1) Experimental method
RAW 264.7 cell density was adjusted to 1X 10 5 cells/well (volume 1 mL) and in logarithmic growth phase, macrophages were induced to be in inflammatory state by addition of LPS (final concentration 1. Mu.g/mL).
Compound I indomethacin was formulated using DMSO to different drug concentrations, 3 parallel duplicate wells were set per concentration, and positive control wells (LPS only) were set, negative control wells (cells and medium), blank control wells (medium).
After 24 hours of incubation, 50. Mu.L of the cell supernatant was added to a new 96-well plate, 50. Mu.L of each of the reagents I of the NO detection kit was added, and the NO content was measured by the Griess method.
Inhibition ratio = ([ NO 2 - ] LPS -[NO 2 - ] LPS+sample )/([NO 2 - ] LPS -[NO 2 - ] untreated )×100
(2) The results are shown in Table 2:
table 2 survival data table
The results show that: compound I shows better NO production inhibitory activity than the positive drug indomethacin, IC thereof 50 25.2. Mu.M.
3. Effect of Compounds on cell viability
MTT can be reduced by succinate dehydrogenase in mitochondria of living cells to water-insoluble blue crystals and deposited in living cells, whereas dead cells do not.
(1) Experimental method
Taking RAW 264.7 cells in logarithmic growth phase according to 1×10 5 cells/well were seeded in 96-well plates at 100 μl per well. The addition of LPS (final concentration 1. Mu.g/mL) induced macrophages to be in an inflammatory state.
After 24 hours of incubation, 50. Mu.L of MTT solution was added to each well at 1mg/mL, and after 4 hours of incubation, the medium was aspirated and 150. Mu.L of DMSO was added to each well. Shaking and shaking evenly. The absorbance value (A) at 490nm wavelength was measured with a microplate reader. Inhibition of cell growth by a drug is expressed in terms of survival, with higher survival indicating lower drug toxicity.
Survival (%) = [ (a) 1 –A 0 )/(A 2 -A 0 )]X 100%, where A 0 Absorbance value of blank control, a 1 For absorbance value of the sample, A 2 As positive control wellsAbsorbance values of (2).
Measuring 5 concentration samples, plotting dose-inhibition rate curve to obtain IC 50 Values. The assay was repeated three times for each sample.
(2) The results are shown in Table 2
The results show that: compound I showed no cytotoxic activity at 25 μm concentration, suggesting that it has a good potential for further preclinical studies.
The present invention is not described in detail in the present application, and is well known to those skilled in the art. Finally, it is noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications and equivalents may be made thereto without departing from the spirit and scope of the technical solution of the present invention, which is intended to be covered by the scope of the claims of the present invention.
Claims (6)
1. A heteroterpene compound characterized by: the structural general formula of the hetero-terpenoid is as follows:
the molecular formula is: c (C) 26 H 26 N 2 O 5 。
2. The diterpenoid compound according to claim 1, characterized in that: the hetero-terpenoid is isolated from fresh fruiting bodies of white ginseng fungus.
3. The method for producing a hetero-terpenoid according to claim 1, wherein: the method comprises the following steps:
s1, leaching white ginseng fungus fruiting bodies with methanol, concentrating the extract to obtain an extract, and extracting the extract with ethyl acetate to obtain an ethyl acetate crude extract;
s2, separating the ethyl acetate crude extract by silica gel normal phase chromatography, and then performing gradient elution to obtain 8 components (Fr.1-Fr.8) with the polarity from small to large;
s3, subjecting the component Fr.2 to column chromatography of glucose gel and using methylene chloride: separating by using an eluting solvent with methanol of 1:1, and continuing to elute dichloromethane with the polarity of: methanol (v/v; 60:1) and ethyl acetate: separating with silica gel chromatographic column of methanol (v/v; 90:1) to obtain pure hetero terpene compound.
4. A process for the preparation of a hetero-terpenoid according to claim 3, wherein: in the step S1, the leaching times of methanol are 2-5 times, and the leaching time of one time is 10 days.
5. A process for the preparation of a hetero-terpenoid according to claim 3, wherein: in the step S2, the solvent adopted in gradient elution is petroleum ether/ethyl acetate, and 10% -80% ethyl acetate/petroleum ether part is collected after elution.
6. Use of a hetero-terpenoid according to claim 1, wherein: the hetero-terpenoid can be applied to the preparation of anti-inflammatory drugs.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311463432.1A CN117486900A (en) | 2023-11-06 | 2023-11-06 | Heteroterpene compound and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311463432.1A CN117486900A (en) | 2023-11-06 | 2023-11-06 | Heteroterpene compound and preparation method and application thereof |
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| CN117486900A true CN117486900A (en) | 2024-02-02 |
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| CN202311463432.1A Pending CN117486900A (en) | 2023-11-06 | 2023-11-06 | Heteroterpene compound and preparation method and application thereof |
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- 2023-11-06 CN CN202311463432.1A patent/CN117486900A/en active Pending
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