CN108774120A - Lapachol class compound and preparation method thereof - Google Patents
Lapachol class compound and preparation method thereof Download PDFInfo
- Publication number
- CN108774120A CN108774120A CN201810435924.2A CN201810435924A CN108774120A CN 108774120 A CN108774120 A CN 108774120A CN 201810435924 A CN201810435924 A CN 201810435924A CN 108774120 A CN108774120 A CN 108774120A
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- Prior art keywords
- lapachol
- compound
- fusarium
- hjt
- angusta
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- -1 Lapachol class compound Chemical class 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 15
- 238000000855 fermentation Methods 0.000 claims abstract description 14
- 230000004151 fermentation Effects 0.000 claims abstract description 14
- 241000327150 Rhodiola angusta Species 0.000 claims abstract description 12
- 244000005700 microbiome Species 0.000 claims abstract description 8
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 241000196324 Embryophyta Species 0.000 claims abstract description 7
- 241000223218 Fusarium Species 0.000 claims abstract description 7
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000000284 extract Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 241000209094 Oryza Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 6
- 239000012530 fluid Substances 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 241001149959 Fusarium sp. Species 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 239000002207 metabolite Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000001963 growth medium Substances 0.000 claims description 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 239000002609 medium Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000010898 silica gel chromatography Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 abstract description 5
- 230000002503 metabolic effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 2
- 238000012827 research and development Methods 0.000 abstract description 2
- 238000000638 solvent extraction Methods 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- MEPSBMMZQBMKHM-UHFFFAOYSA-N Lomatiol Natural products CC(=C/CC1=C(O)C(=O)c2ccccc2C1=O)CO MEPSBMMZQBMKHM-UHFFFAOYSA-N 0.000 description 1
- 241001165494 Rhodiola Species 0.000 description 1
- CIEYTVIYYGTCCI-UHFFFAOYSA-N SJ000286565 Natural products C1=CC=C2C(=O)C(CC=C(C)C)=C(O)C(=O)C2=C1 CIEYTVIYYGTCCI-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- KNOSIOWNDGUGFJ-UHFFFAOYSA-N hydroxysesamone Natural products C1=CC(O)=C2C(=O)C(CC=C(C)C)=C(O)C(=O)C2=C1O KNOSIOWNDGUGFJ-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- CWPGNVFCJOPXFB-UHFFFAOYSA-N lapachol Chemical compound C1=CC=C2C(=O)C(=O)C(CC=C(C)C)=C(O)C2=C1 CWPGNVFCJOPXFB-UHFFFAOYSA-N 0.000 description 1
- SIUGQQMOYSVTAT-UHFFFAOYSA-N lapachol Natural products CC(=CCC1C(O)C(=O)c2ccccc2C1=O)C SIUGQQMOYSVTAT-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007269 microbial metabolism Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/66—Preparation of oxygen-containing organic compounds containing the quinoid structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention belongs to pharmaceutical technology fields, three kinds of new lapachol class compounds are obtained more particularly to being extracted from fusarium plant endogenesis microbial metabolic products, chemical compounds I 1-methoxylfusarnaphthoquinones A, compound ii 5-dehydroxysolaninol, compound III 1-dehydroxysolaninol；The present invention is to acquire from Rhodiola angusta（Rhodiola angustaNakai）The interior raw fusarium microorganism at blade position（Fusariumsp.HJT-P-5）Solid fermentation product be raw material, detached through solvent extraction and a variety of chromatographic processes, obtain three new lapachol class compounds of the invention；This kind of new lapachol class compound of the present invention and preparation method thereof has very important significance in antitumor drug research and development.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to be extracted from fusarium plant endogenesis microbial metabolic products
Obtain three kinds of new lapachol class compounds, chemical compounds I 1-methoxylfusarnaphthoquinones A, compound ii 5-
The preparation method of dehydroxysolaninol, compound III 1-dehydroxysolaninol and three kinds of compounds.
Background technology
Isolated 50000 kinds or more of the natural products from microbial metabolic products at present, many of compound life
Object activity is good, has the potential quality being developed to as newtype drug.With going deep into for research, produced from traditional terrestrial microbial metabolism
The probability that pilot compound is obtained in object continuously decreases, and speed slows down year by year, therefore develops special border microbial resources as working as
Business is anxious.Plant endogenesis microorganism can be metabolized since its habitat is special and generate that structure is special, and the good compound of activity is
One of current research hotspot.
To raw microorganism in Rhodiola angustaFusarium Sp. HJT-P-5's studies have shown that its metabolite contain it is more
Kind lapachol class compound, such compound have apparent inhibition to live human lung cancer cell A549 and human colon cancer cell HCT116
Property.
Invention content
The present invention provides acquire from Rhodiola angusta（Rhodiola angustaNakai）The interior raw sickle at blade position
The mould microorganism belonging to genus of knife（Fusarium sp. HJT-P-5）Solid fermentation product in isolated three novel lapachol classes
Object I ~ III is closed, chemical compounds I is named as 1- methoxylfusarnaphthoquinones A, and compound ii is named as 5-
Dehydroxysolaninol, the entitled 1- dehydroxysolaninol of compound III, chemical structural formula are respectively：
。
Pharmacological activity shows that these three compounds have significantly human lung cancer cell A549 and human colon cancer cell HCT116
Inhibitory activity.
The preparation method of these three lapachol class compounds is to acquire from Rhodiola angusta（Rhodiola angusta
Nakai）The interior raw fusarium microorganism at blade position（Fusarium sp.HJT-P-5）Solid fermentation product be raw material,
It is detached through solvent extraction and a variety of chromatographic processes, obtains three new lapachol class compounds；Using high resolution mass spectrum, nuclear-magnetism is total
Shake equal spectroscopy techniques, it is determined that the structure of these three compounds, specific preparation process are as follows：
（1）It will acquire from Rhodiola angusta（Rhodiola angustaNakai）The interior raw fusarium microorganism at blade position
（Fusarium sp. HJT-P-5）Carry out solid fermentation；
Solid culture based formulas：Rice, pure water；
Fermentation condition：Bacterial strain HJT-P-5 is inoculated in shaking table shake culture in the conical flask of No. 4 culture medium zymotic fluids of fungi, then
The zymotic fluid of shake culture is inoculated in be left to ferment in the conical flask equipped with solid medium together with mycelium and is cultivated；
（2）The extraction of metabolite：Plant endogenesis epiphyte HJT- P-5 solid fermentation products are surpassed using equal-volume acetone
Sound extracts, and through 8 layers of filtered through gauze, extracting solution is detached with mycelium and rice, extracting solution is concentrated to dryness, and water is added to be suspended, successively
With isometric ethyl acetate, extracting n-butyl alcohol 3 times, solvent is recovered under reduced pressure and obtains acetic acid ethyl ester extract and extracting n-butyl alcohol
Object；
（3）Ethyl acetate layer is isolated and purified with normal phase silica gel column chromatography, uses volume ratio for chloroform:Methanol=100:0,100:1,
100:2,100:3,100:5,100:10 gradient elution collects eluent；
（4）Step（3）Eluent purified through high performance liquid chromatography separation, use volume ratio for acetonitrile:Water:Tetrahydrofuran=15:
80:5 solution elution, obtains chemical compounds I, uses volume ratio for acetonitrile after concentration:Water=31:69 solution elute compound ii,
Ⅲ。
Beneficial effects of the present invention are：The compound of the present invention is new lapachol class compound, and raw material of the present invention is to plant
Raw microbial fermentation product, is easy to get safely, method is simple to operation, does not introduce noxious material, of low cost, can be extensive in object
Sustainable exploitation utilization.The compound of the present invention and preparation method have very important meaning in antitumor drug research and development
Justice.
Specific implementation mode
Below in conjunction with specific implementation mode, the present invention will be further described.
Embodiment 1
The preparation of chemical compounds I ~ III：
（1）It will acquire from Rhodiola angusta（Rhodiola angustaNakai）The interior raw fusarium microorganism at blade position
（Fusarium sp. HJT-P-5）Carry out solid fermentation；
Solid culture based formulas：Rice 80g, pure water 120ml；
Fermentation condition：Bacterial strain HJT-P-5 is inoculated in the 4 bottled 500 mL tapers for there are No. 4 culture medium zymotic fluids of 200 mL fungies
Shaking table shake culture 2d in bottle（Condition of culture：28 DEG C, 120 r/min）, then by the zymotic fluid after shake culture 2d together with mycelia
Body is inoculated in standing for fermentation culture 40d in the 40 bottled 500 mL conical flasks for having solid medium in the ratio of inoculum concentration 10%,
（Condition of culture：28℃）；
（2）The extraction of metabolite：Plant endogenesis epiphyte HJT- P-5 solid fermentation products are surpassed using equal-volume acetone
Sound extracts, and 15min × 3 time detach extracting solution with mycelium and rice, extracting solution is concentrated to dryness, and is added through 8 layers of filtered through gauze
2L water is suspended, and successively with isometric ethyl acetate, extracting n-butyl alcohol 3 times, solvent is recovered under reduced pressure and obtains acetic acid ethyl ester extract
（44.66g）And n-butyl alcohol extract（41.13g）；
（3）Ethyl acetate layer is isolated and purified with normal phase silica gel column chromatography, uses volume ratio for chloroform:Methanol=100:0,100:1,
100:2,100:3,100:5,100:10 gradient elution collects eluent；
（4）Step（3）Eluent purified through high performance liquid chromatography separation, use volume ratio for acetonitrile:Water：Tetrahydrofuran=15:
80:5 solution elution, obtains compound 1, uses volume ratio for acetonitrile after concentration:Water=31:69 solution elute compound ii,
Ⅲ。
Using nuclear magnetic resonance（NMR）Equal spectroscopic techniques measure its structure, and the spectral data of chemical compounds I ~ III see the table below 1 ~ table
3。
1 chemical compounds I hydrogen of table composes (500 MHz) and carbon composes (125 MHz) nuclear magnetic data（DMSO-d 6）
2 compound ii hydrogen of table composes (500 MHz) and carbon composes (125 MHz) nuclear magnetic data（DMSO-d 6）
3 compound III hydrogen of table composes (500 MHz) and carbon composes (125 MHz) nuclear magnetic data（DMSO-d 6）
Claims (2)
1. the lapachol class compound of following chemical structural formulas I ~ III：
。
2. the preparation method of lapachol class compound as described in claim 1, which is characterized in that the method step is：
（1）It will acquire from Rhodiola angusta（Rhodiola angustaNakai）The interior raw fusarium microorganism at blade position
（Fusarium sp. HJT-P-5）Carry out solid fermentation；
Solid culture based formulas：Rice, pure water；
Fermentation condition：Bacterial strain HJT-P-5 is inoculated in shaking table shake culture in the conical flask of No. 4 culture medium zymotic fluids of fungi, then
The zymotic fluid of shake culture is inoculated in be left to ferment in the conical flask equipped with solid medium together with mycelium and is cultivated；
（2）The extraction of metabolite：Plant endogenesis epiphyte HJT- P-5 solid fermentation products are surpassed using equal-volume acetone
Sound extracts, and through 8 layers of filtered through gauze, extracting solution is detached with mycelium and rice, extracting solution is concentrated to dryness, and water is added to be suspended, successively
With isometric ethyl acetate, extracting n-butyl alcohol 3 times, solvent is recovered under reduced pressure and obtains acetic acid ethyl ester extract and extracting n-butyl alcohol
Object；
（3）Ethyl acetate layer is isolated and purified with normal phase silica gel column chromatography, uses volume ratio for chloroform：Methanol=100:0,100:1,
100:2,100:3,100:5,100:10 gradient elution collects eluent；
（4）Eluent is purified through high performance liquid chromatography separation, uses volume ratio for acetonitrile:Water:Tetrahydrofuran=15:80:5 it is molten
Liquid elutes, and chemical compounds I is obtained after concentration, uses volume ratio for acetonitrile:Water=31:69 solution elutes to obtain compound ii, compound
Ⅲ。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810435924.2A CN108774120B (en) | 2018-05-09 | 2018-05-09 | Lapatiquinone compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810435924.2A CN108774120B (en) | 2018-05-09 | 2018-05-09 | Lapatiquinone compound and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108774120A true CN108774120A (en) | 2018-11-09 |
| CN108774120B CN108774120B (en) | 2021-04-06 |
Family
ID=64026976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810435924.2A Active CN108774120B (en) | 2018-05-09 | 2018-05-09 | Lapatiquinone compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108774120B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116041307A (en) * | 2023-01-31 | 2023-05-02 | 三峡大学 | Preparation method of 4, 9-dihydroxyl-alpha-lapachone from catalpa bungei |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837399A (en) * | 1988-05-10 | 1989-06-06 | The United States Of America As Represented By The Secretary Of Agriculture | Napthoquinone antibiotics from fuserium solani |
| CN104274432A (en) * | 2013-07-01 | 2015-01-14 | 上海来益生物药物研究开发中心有限责任公司 | Application of naphthoquinone derivative solaniol in preparation of antiviral drugs |
| CN105056230A (en) * | 2015-08-03 | 2015-11-18 | 中国医学科学院医学生物学研究所 | Application of beta-lapachone, and beta-lapachone containing compound adjuvant and vaccine |
| CN105294638A (en) * | 2015-10-30 | 2016-02-03 | 成都科创佳思科技有限公司 | Catalyzed synthesis method of dehydrogenated alpha-lapachol |
| WO2017106624A1 (en) * | 2015-12-18 | 2017-06-22 | The Board Of Regents Of The University Of Texas System | Napthoquinones, pro-drugs, and methods of use thereof |
-
2018
- 2018-05-09 CN CN201810435924.2A patent/CN108774120B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837399A (en) * | 1988-05-10 | 1989-06-06 | The United States Of America As Represented By The Secretary Of Agriculture | Napthoquinone antibiotics from fuserium solani |
| CN104274432A (en) * | 2013-07-01 | 2015-01-14 | 上海来益生物药物研究开发中心有限责任公司 | Application of naphthoquinone derivative solaniol in preparation of antiviral drugs |
| CN105056230A (en) * | 2015-08-03 | 2015-11-18 | 中国医学科学院医学生物学研究所 | Application of beta-lapachone, and beta-lapachone containing compound adjuvant and vaccine |
| CN105294638A (en) * | 2015-10-30 | 2016-02-03 | 成都科创佳思科技有限公司 | Catalyzed synthesis method of dehydrogenated alpha-lapachol |
| WO2017106624A1 (en) * | 2015-12-18 | 2017-06-22 | The Board Of Regents Of The University Of Texas System | Napthoquinones, pro-drugs, and methods of use thereof |
Non-Patent Citations (2)
| Title |
|---|
| G.R.NALIN RATHNAYAKE等: "Chemical investigation of metabolites produced by an endophytic fungi Phialemonium curvatum from the leaves of Passiflora edulis", 《NATURAL PRODUCT RESEARCH》 * |
| KONGKIAT TRISUWAN等: "Anthraquinone, Cyclopentanone, and Naphthoquinone Derivatives from the Sea Fan-Derived Fungi Fusarium spp. PSU-F14 and PSU-F135", 《J. NAT. PROD.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116041307A (en) * | 2023-01-31 | 2023-05-02 | 三峡大学 | Preparation method of 4, 9-dihydroxyl-alpha-lapachone from catalpa bungei |
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| CN108774120B (en) | 2021-04-06 |
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