CN114560831A - Dihydrofuranone derivative and extraction method and application thereof - Google Patents
Dihydrofuranone derivative and extraction method and application thereof Download PDFInfo
- Publication number
- CN114560831A CN114560831A CN202210193134.4A CN202210193134A CN114560831A CN 114560831 A CN114560831 A CN 114560831A CN 202210193134 A CN202210193134 A CN 202210193134A CN 114560831 A CN114560831 A CN 114560831A
- Authority
- CN
- China
- Prior art keywords
- ethyl acetate
- dihydrofuranone
- component
- petroleum ether
- methanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000605 extraction Methods 0.000 title abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 91
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000003208 petroleum Substances 0.000 claims abstract description 29
- 241000233866 Fungi Species 0.000 claims abstract description 24
- 210000004027 cell Anatomy 0.000 claims abstract description 22
- 239000003480 eluent Substances 0.000 claims abstract description 17
- 239000000287 crude extract Substances 0.000 claims abstract description 14
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000741 silica gel Substances 0.000 claims abstract description 12
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 12
- 230000005764 inhibitory process Effects 0.000 claims abstract description 6
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 4
- 238000000855 fermentation Methods 0.000 claims description 11
- 230000004151 fermentation Effects 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 241000123650 Botrytis cinerea Species 0.000 claims description 6
- 241000233616 Phytophthora capsici Species 0.000 claims description 6
- 230000000259 anti-tumor effect Effects 0.000 claims description 6
- 210000005229 liver cell Anatomy 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 201000007270 liver cancer Diseases 0.000 claims description 3
- 208000014018 liver neoplasm Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 241000223600 Alternaria Species 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 241000233948 Typha Species 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 241000361202 Cheilosia ranunculi Species 0.000 claims 1
- 241000223218 Fusarium Species 0.000 claims 1
- 229940124350 antibacterial drug Drugs 0.000 claims 1
- 230000009982 effect on human Effects 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 230000000694 effects Effects 0.000 abstract description 16
- 241000228232 Aspergillus tubingensis Species 0.000 abstract description 10
- 210000003608 fece Anatomy 0.000 abstract description 7
- 240000001398 Typha domingensis Species 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 210000001161 mammalian embryo Anatomy 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 2
- 230000002538 fungal effect Effects 0.000 abstract description 2
- 210000003494 hepatocyte Anatomy 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 11
- 229930000044 secondary metabolite Natural products 0.000 description 10
- 239000000523 sample Substances 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 206010039509 Scab Diseases 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000013641 positive control Substances 0.000 description 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000282324 Felis Species 0.000 description 4
- 230000002292 Radical scavenging effect Effects 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 241000751897 Paederus Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002447 crystallographic data Methods 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000005918 in vitro anti-tumor Effects 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 2
- 241000223602 Alternaria alternata Species 0.000 description 2
- 241000385333 Cryptolepis Species 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 244000000004 fungal plant pathogen Species 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229920001470 polyketone Polymers 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 235000006836 Decaisnea insignis Nutrition 0.000 description 1
- 241000340636 Decaisnea insignis Species 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 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 description 1
- 206010019909 Hernia Diseases 0.000 description 1
- 244000241838 Lycium barbarum Species 0.000 description 1
- 235000015459 Lycium barbarum Nutrition 0.000 description 1
- 235000015468 Lycium chinense Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000863503 Paederia Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 208000008350 Pruritus Vulvae Diseases 0.000 description 1
- 241000218206 Ranunculus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 244000057717 Streptococcus lactis Species 0.000 description 1
- 235000014897 Streptococcus lactis Nutrition 0.000 description 1
- 206010056530 Vulvovaginal pruritus Diseases 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 235000017807 phytochemicals Nutrition 0.000 description 1
- 229930000223 plant secondary metabolite Natural products 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 150000003881 polyketide derivatives Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010267 two-fold dilution method Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a dihydrofuranone derivative and an extraction method and application thereof, wherein the endophytic fungus of cat-tail feces, aspergillus tubingensis DS37, is extracted by petroleum ether/ethyl acetate/methanol, the extracting solution is combined and filtered, and the pressure reduction concentration is carried out to obtain a crude extract; and (3) putting the crude extract on a silica gel chromatographic column, eluting by using petroleum ether/ethyl acetate/methanol eluent with different volume gradients, and recrystallizing to obtain the dihydrofuranone derivative. The dihydrofuranone derivative prepared by the invention has good fungal inhibition effect and can be used for medicament control technology; the dihydrofuranone derivative has better cell strain activity on a HepG2 cell strain and a human embryo hepatocyte L02, and can provide a possibility for the development of antitumor drugs; meanwhile, the compound also has certain antioxidant activity.
Description
Technical Field
The invention belongs to the technical field of polyketide preparation, and relates to a dihydrofuranone derivative, and an extraction method and application thereof.
Background
The plant of Ranunculi ternata (Decaisnea insignis (Griff.) hook. f. & Thomson) is called Cat melon (Qinling) and short wolfberry tree, and belongs to the genus Ranunculus of Lardiyabaeeae (Lardiyabaeeae). The bush is widely distributed in southwest and middle areas of China. The cat-tail feces is a traditional folk Chinese herbal medicine in China, is pungent, sweet and neutral in taste, and sweet and cool in root and fruit, and has the effects of clearing lung-heat, relieving cough, dispelling wind and removing dampness, treating rheumatic arthralgia, pruritus vulvae, hernia and the like. The current research on the paediatric feces mainly focuses on the phytochemical components of the paediatric feces, and the research on the endophytic fungi is reported to be less. The endophytic fungi and the plants coexist reciprocally for a long time, secondary metabolites which are the same as or similar to the host can be produced, and the secondary metabolites have various biological activities and are potential resources for screening bacteriostatic active substances. The endophytic fungi secondary metabolite categories are reported to be mainly: the compounds such as coumarin, polyketone, steroid, ester, alkaloid, phenolic acid, flavonoid, terpene and the like all have certain biological activity. However, no report on dihydrofuranone derivatives in endophytic fungi of Ranunculi ternata has been found.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a dihydrofuranone derivative and an extraction method and application thereof, the dihydrofuranone derivative separated from a secondary metabolite of feline panne endophytic fungus DS37 is separated from aspergillus tubingensis for the first time, and the dihydrofuranone derivative has good fungal activity and antioxidant activity and good activity on human liver cancer cells and human embryonic liver cells.
The invention is realized by the following technical scheme:
a dihydrofuranone derivative having the chemical formula:
a method for extracting dihydrofuranone derivatives comprises:
step (1): extracting solid fermentation products of the cat-tail endophytic fungi DS37 serving as raw materials with petroleum ether, ethyl acetate and methanol for a plurality of times respectively, combining extracting solutions, filtering, recovering a mixed solvent, and concentrating the filtered extracting solution under reduced pressure to obtain a crude extract, wherein the mass ratio of the solid fermentation products of the cat-tail endophytic fungi DS37 to the crude extract is 92: 15;
step (2): eluting the crude extract obtained in the step (1) on a silica gel chromatographic column by using petroleum ether/ethyl acetate/methanol eluent with the volume gradient of 1:0:0,0:1:0,0:1:1,0:0:1 respectively to obtain a petroleum ether phase component A, an ethyl acetate phase component B, an ethyl acetate/methanol phase component C and a methanol phase component D respectively; the mass ratio of the crude extract to the components A, B, C and D is 150:11:42:70: 10; the volume ratio of ethyl acetate to methanol in the component C is 1: 1;
and (3): eluting the component B obtained in the step (2) on a silica gel chromatographic column by using petroleum ether/ethyl acetate eluent with the volume gradient of 100:0,100:20,100:50,100:100,100:200 and 0:100 respectively to obtain six components B1-B6; continuously eluting the component B4 on a silica gel chromatographic column by using petroleum ether/ethyl acetate eluent with the volume gradient of 100:0,100: 25, 100:50,100: 70, 100:90, 100:100,100: 130, 100:150, 100:180, 100:200 and 0:100 to obtain eleven components B4-1-B4-11; eluting the component B4-6 with petroleum ether-ethyl acetate eluent with the volume gradient of 100:25, 100:45, 100:65, 100:85, 100:105, 100:125, 100:145, 100:165, 100:185 and 100:205 to obtain ten components B4-6-1-B4-6-10, wherein the component B4-6-3 is recrystallized to obtain the dihydrofuranone derivative; the mass ratio of the component B to the component B4 is 21:1, the mass ratio of the component B4 to the component B4-6 is 20:3.7, and the mass ratio of the component B4-6 to the dihydrofuranone derivative is 1480: 17.
Preferably, the solid fermentation product of the paederus endophytic fungus DS37 in the step (1) is leached for 8 times by petroleum ether/ethyl acetate/methanol.
Preferably, the petroleum ether, ethyl acetate and methanol are all industry standards.
An application of dihydrofuranone derivative in antibacterial, antioxidant and antitumor drugs is provided.
Preferably, the inhibition of bacteria refers to inhibition of bacteria or fungi.
Preferably, the bacteriostasis refers to the inhibition effect on wheat scab, tobacco brown spot pathogen, phytophthora capsici and tomato botrytis cinerea.
Preferably, the antioxidant activity refers to an antioxidant effect on 1, 1-diphenyl-2-trinitrophenylhydrazine.
Preferably, the anti-tumor refers to the in vitro effects on human lung cancer cells, human prostate cancer cells, human breast cancer cells, human liver cancer cells and human embryonic liver cells.
Preferably, anti-tumor refers to in vitro effects on HepG2 cell line and L02 cell line.
Compared with the prior art, the invention has the following beneficial technical effects:
the dihydrofuranone derivative which is a secondary metabolite of the paederia fargesii endophytic fungus DS37 is a compound with good activity, and the molecular formula of the dihydrofuranone derivative is C20H12O8In addition, the dihydrofuranone derivative compound is obtained by extracting a dried secondary metabolite of the cat-tail endophytic fungus DS37 after solid fermentation, and is separated from aspergillus tubingensis for the first time. Tests on the antibacterial activity of the dihydrofuranone derivative disclosed by the invention for the first time show that the compound has good antifungal activity, and particularly has good antibacterial activity on wheat scab, tobacco brown spot, phytophthora capsici and botrytis cinerea, so that the compound can be used for agricultural control and medicament control technologies. In addition, the antioxidant activity of the dihydrofuranone derivative is tested for the first time, and the compound is found to have a certain antioxidant effect on DPPH. Meanwhile, the in vitro anti-tumor activity of the dihydrofuranone derivative is tested for the first time, and the compound is found to have better cytotoxic activity to HepG2 cell strains and L02.
Drawings
FIG. 1 is a UV spectrum of a dihydrofuranone derivative of the present invention;
FIG. 2 is an infrared spectrum of a dihydrofuranone derivative of the present invention;
FIG. 3 is a drawing showing the preparation of dihydrofuranone derivatives of the present invention1H-NMR spectrum;
FIG. 4 shows the preparation of dihydrofuranone derivatives13C-NMR spectrum;
FIG. 5 is a DEPT (135 ℃) spectrum of a dihydrofuranone derivative of the present invention;
FIG. 6 is a NOESY diagram of a dihydrofuranone derivative of the present invention;
FIG. 7 is a HSQC diagram of the dihydrofuranone derivatives of the present invention;
FIG. 8 is a diagram of HMBC of a dihydrofuranone derivative of the present invention;
FIG. 9 is a HR-ESI-M spectrum of a dihydrofuranone derivative of the present invention;
FIG. 10 is a structural view of an X-ray single crystal of a dihydrofuranone derivative of the present invention;
FIG. 11 is a structural diagram of a dihydrofuranone derivative of the present invention.
Deposit description
The invention carries out the following preservation on an endophytic fungus Aspergillus tubingensis DS37 separated from the stem of a paederus plant:
preservation time: 22/3/2018, deposit site: china, Wuhan. China Center for Type Culture Collection (CCTCC); the preservation number is CCTCC M2018147, and the classification name is Aspergillus tubingensis (Aspergillus tubingensis).
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
Embodiments of the invention are described in further detail below:
a dihydrofuranone derivative having the chemical formula:
the extraction method of the compound comprises the following steps:
(1) leaching 9.2kg of a secondary metabolite of the feline feces endophytic fungus DS37 with petroleum ether/ethyl acetate/methanol for 8 times, combining the extracting solutions, filtering, recovering a mixed solvent, and concentrating under reduced pressure to obtain 1500g of a crude extract;
(2) respectively eluting the crude extract obtained in the step (1) on a silica gel chromatographic column by using petroleum ether/ethyl acetate/methanol eluent with the volume gradient of 1:0:0,0:1:0,0:1:1,0:0:1 to obtain a petroleum ether phase component A, an ethyl acetate phase component B, an ethyl acetate/methanol phase component C and a methanol phase component D; wherein, the component A (110g), the component B (420g), the component C (700g) and the component D (100g) are four components; the volume ratio of ethyl acetate to methanol in the component C is 1: 1;
(3) eluting the component B (420g) obtained in the step (2) on a silica gel chromatographic column by using petroleum ether/ethyl acetate eluent with the volume gradient of 100:0,100:20,100:50,100:100,100:200 and 0:100 respectively to obtain six components B1-B6, and eluting the component B4(20g) on the silica gel chromatographic column by using petroleum ether/ethyl acetate eluent with the volume gradient of (V/V)100:0, 10:25, 100:50,100: 70, 100:90, 100:100,100: 130, 100:150, 100:180, 100:200 and 0:100 to obtain eleven components B4-1-B4-11; elution of fraction B4-6(3.7g) with a volume gradient (V/V)10:25, 100:45, 100:65, 100:85, 100:105, 100:125, 100:145, 100:165, 100:185, 100:205 petroleum ether-ethyl acetate eluent gave ten fractions (B4-6-1-B4-6-10) in which fraction B4-6-3 was recrystallized to give the dihydrofuranone derivative (42.5 mg).
The prepared cryptolepis crenata endophytic fungus DS37 secondary metabolite-dihydrofuranone derivative is a polyketone compound with good antibacterial activity, and at present, no report of separating the compound from cryptolepis crenata endophytic fungus is found, and the compound is separated from aspergillus tubingensis fermentation products for the first time; at present, no report about the activity research of the compound is found in endophytic fungi of the paederus cinerea plant, and no report about the activity research of artificially synthesizing the compound is found. The invention adopts a silica gel column chromatography method to separate and identify a dihydrofuranone derivative-2, 4,6a,10, 12-pentahydroxyl-6, 6 a-dihyd-rodiptho [2,1-b:1',2' -d ] furan-5,9-dione with broad-spectrum activity to the fungus from the solid fermentation product of the cat's dung endophytic fungus DS37, and the activity of the compound is reported for the first time.
Obtained by the inventionThe compound (b) is an orange crystal, and [ M + Na ] appears at M/z 403.04255 in an ESI-HR-MS spectrum]+Ion peak, calculating its molecular formula as C20H12O8，1H and13the C nmr data are shown in table 1 and the crystallographic data are shown in table 2.
TABLE 1 preparation of dihydrofuranone derivatives1H and13c nuclear magnetic data
TABLE 2 crystallographic data of dihydrofuranone derivatives
The antibacterial activity test of the dihydrofuranone derivative shows that the compound has good antifungal activity, particularly has good antibacterial activity on wheat scab, alternaria alternate, phytophthora capsici and botrytis cinerea, and is an antibacterial active ingredient of a secondary metabolite of the feline excrement endophytic fungus DS37, so that the compound can be used for agricultural control and medicament control technologies.
The antioxidant activity test of the compound shows that the compound has certain antioxidant activity to 1, 1-diphenyl-2-trinitrophenyl hydrazine (DPPH).
Through in vitro anti-tumor activity tests of the compound, the compound is found to have better activity on HepG2 tumor cell strains and human embryo liver cells L02, and is an anti-tumor component of a secondary metabolite of the feline panniculus endophytic fungus DS37, so that the compound can provide a possibility for development of anti-tumor drugs.
As shown in FIGS. 1-9, from compounds1H-NMR、13The C-NMR, DEPT (135 degree), NOESY, HSQC, HMBC, HR-ESI-M spectra, and crystal structure finally determined the structure of the compound. The compound is dihydrofuranone derivative which is separated from Aspergillus tubingensis fermentation product for the first time and has no activity reported in literature, and related NMR numberThe data and crystallographic data are shown in tables 1 and 2.
The invention is further illustrated by the following examples:
firstly, culturing the strain of the cat-tail feces endophytic fungus Aspergillus tubingensis (Aspergillus tubingensis) DS37 in a strain culture medium; secondly, carrying out fermentation culture on the strains in a fermentation culture medium to obtain 9.2kg of secondary metabolites, leaching for 8 times by using petroleum ether/ethyl acetate/methanol, combining extracting solutions, filtering, recovering a mixed solvent, and concentrating under reduced pressure to obtain 1500g of crude extract; respectively eluting the obtained crude extract on a silica gel chromatographic column by using petroleum ether/ethyl acetate/methanol eluent with the volume gradient of 1:0:0,0:1:0,0:1:1,0:0:1 to obtain four components of A (110g), B (420g), C (700g) and D (100 g); eluting the component B extract with petroleum ether/ethyl acetate (100:0,100:20,100:50,100:100,100:200,0:100, v/v) eluents with different gradients on silica gel chromatographic column to obtain six components B1-B6; eluting the component B4(20g) with petroleum ether/ethyl acetate (V/V) eluent with the volume gradient of (V/V)100:0, 10:25, 100:50,100: 70, 100:90, 100:100,100: 130, 100:150, 100:180, 100:200 and 0:100 to obtain eleven components B4-1-B4-11; the B4-6(3.7g) fractions were eluted with a volume gradient (V/V)10:25, 100:45, 100:65, 100:85, 100:105, 100:125, 100:145, 100:165, 100:185, 100:205 petroleum ether-ethyl acetate eluent to give ten fractions (B4-6-1-B4-6-10), of which fraction B4-6-3 was recrystallized to give a dihydrofuranone derivative (42.5 mg).
Antibacterial activity test of dihydrofuranone derivatives:
1. experimental Material
1.1, test samples
The dihydrofuranone derivative was dissolved in DMSO to prepare a solution of 500. mu.g/mL.
1.2 strains
Two gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and two gram-positive bacteria (Staphylococcus aureus, Streptococcus lactis).
1.3 culture Medium
3.0g/L, NaCl 5.0.0 g/L beef extract and 10.0g/L, pH 7.0.0-7.5 g peptone.
1.4 other materials
96-well plates.
2. Experimental methods
Each well of a 96-well plate was filled with 100. mu.L of the above medium at a concentration of 1X 10 per 100. mu.L6CFU/mL cell suspension, 500. mu.g/mL sample solution was added to the first well, the sample concentration was 500, 250, 125, 62.5, 31.2, 15.6, 7.81, 3.91, 1.95 and 0.975. mu.g/mL in order from the first well to the tenth well by the double dilution method, and 100. mu.L of the above-mentioned medium and DMSO were added to the eleventh and twelfth wells, respectively, as controls. Streptomycin sulfate is used as the positive control of gram-negative bacteria, and penicillin sodium is used as the positive control of gram-positive bacteria. Each of the above groups was subjected to 3 parallel experiments, and the 96-well plate was incubated in an incubator at 37 ℃ for 24 hours.
3. Results of the experiment
The results are shown in table 3 and show that the dihydrofuranone derivatives do not exhibit significant bacteriostatic activity against bacteria.
Antifungal Activity of dihydrofuranone derivatives:
1. experimental Material
1.1, test samples
The dihydrofuranone derivative was dissolved in DMSO to prepare a solution of 500. mu.g/mL.
1.2 strains
Five plant pathogenic fungi (wheat scab, tobacco brown spot, pepper phytophthora, tomato gray mold, rape sclerotinia sclerotiorum).
1.3 culture Medium
200g of potato extract, 20g of glucose and 1000mL of water.
1.4 other materials
96-well plates.
2. Experimental methods
Each well of a 96-well plate was filled with 100. mu.L of the above medium at a concentration of 1X 10 per 100. mu.L6CFU/mL cell suspension, adding 500 μ g/mL sample solution into the first well, and using two-fold dilution method to make the sample concentration from the first well to the tenth well be 500, 250, 125, 62.5, 31.2, 15.6, 7.81, 3.91, 1.95 and 0.975. mu.g/mL, and 100. mu.L of the above medium and DMSO were added to the eleventh and twelfth wells, respectively, as controls. Carbendazim is selected as the positive control of plant pathogenic fungi. 3 replicates of each group were run and the 96-well plates were incubated in a 28 ℃ incubator for 48 hours.
3. Results of the experiment
The results are shown in Table 3, and show that the dihydrofuranone derivative has better inhibitory activity on wheat scab, alternaria tabacum, phytophthora capsici and botrytis cinerea, and the MIC (minimum inhibitory concentration) is 128 mu g/mL.
TABLE 3 bacteriostatic Activity of dihydrofuranone derivatives
Wherein: a is escherichia coli; b, pseudomonas aeruginosa; c: staphylococcus aureus bacteria; d: a lactic acid streptococcus; e: wheat scab bacteria; f: alternaria alternate; g: phytophthora capsici; h: botrytis cinerea; i: sclerotinia sclerotiorum; -: no experiment was set up.
Antioxidant activity test of dihydrofuranone derivatives:
1. experimental Material
1.1, test samples
The dihydrofuranone derivative is dissolved in methanol to prepare the dihydrofuranone derivative with the concentration of 2 mg/mL-1The solution of (1).
1.2, preparing 1, 1-diphenyl-2-trinitrophenylhydrazine (DPPH) solution
Dissolving 0.0200g of 1, 1-diphenyl-2-trinitrophenylhydrazine in a proper amount of methanol, transferring the solution to a 100mL volumetric flask after complete dissolution to prepare fresh 0.200mg mL-1DPPH-methanol solution of (c).
1.3 other materials
Baygen pipette, microplate reader.
2 method of experiment
The sample was dissolved in methanol to prepare a solution having a mass concentration of 2 mg/mL. First, 100. mu.L of methanol was added to each well of the first and second rows of the microplate in sequence. Secondly, 100 mu L of samples to be detected are added into the first holes of the two rows respectively, the samples are mixed uniformly by a pipette, 100 mu L of the samples is sucked and added into the 2 nd hole of each row, then the liquid in the 2 nd hole is mixed uniformly, 100 mu L of the samples is sucked and added into the 3 rd hole of each row, the operation is carried out until the 11 th hole is reached, 100 mu L of the solution is sucked and discarded, and finally, the samples which are not added into the first hole are used as blank control. Finally, 100. mu.L of the prepared DPPH solution was added to each well of the first row, and 100. mu.L of methanol was added to each well of the second row. The ELISA plate was placed at room temperature and protected from light for 30min, Vc was used as a positive control, and the absorbance of each compound was measured at a wavelength of 517nm using an ELISA reader, and each group was assayed 3 times in parallel. The clearance was calculated as follows:
clearance rate is 1- (A)i-Aj)/A0×100％
In the formula: a. thei-absorbance of the test substance after DPPH addition; a. the0-absorbance of methanol plus DPPH; a. thej-absorbance of the test substance after addition of methanol.
Since the measured compound concentration and the DPPH radical scavenging rate are linear, a dose-effect curve can be established with the radical scavenging rate as ordinate and the sample concentration as abscissa, and the concentration (IC) of the sample at a radical scavenging rate of 50% can be determined from the dose-effect curve50)。
3. Results of the experiment
The results of radical scavenging rate test of dihydrofuranone derivatives are shown in Table 4, and the IC can be found from the experimental data50Was 112.63 (. mu.g.mL)-1) The result shows that the compound has certain antioxidant activity on DPPH.
TABLE 4 free radical scavenging test results for dihydrofuranone derivatives
Antitumor activity test of dihydrofuranone derivative:
1. experimental Material
1.1, test samples
The dihydrofuranone derivative was dissolved in DMSO to prepare a 20mM solution.
1.2 tumor cells
Human lung cancer cell (A549), human prostate cancer cell (PC-3), human breast cancer cell (MCF-7), human hepatoma cell (HepG2), human embryo hepatocyte (L02).
1.3 other materials
The kit comprises high-glucose DMEM culture solution, fetal calf serum, a 96-hole cell culture plate with a transparent bottom, an aseptic centrifuge tube, an aseptic pipette, an aseptic sample adding groove, an aseptic gun head, MTT, a multi-channel pipette and an enzyme labeling instrument.
2. Experimental methods
Taking cells in logarithmic growth phase, trypsinizing the cells, adjusting the cell suspension concentration to 5x104PermL, 100. mu.L/well in the middle 6 rows of a 96-well cell culture plate, and 100. mu.L/well in the 1 st and 8 th rows. The culture plate is placed at 37 ℃ and 5% CO2Overnight in an incubator. Preparing a sample on the next day, wherein the positive control is adriamycin and is dissolved to 300 mu M by using sterile normal saline; samples were dissolved to 20mM in DMSO. The adriamycin is diluted to 9 mu M by culture solution, and then 3-fold dilution is carried out in sequence, and 6 concentrations are carried out, namely, the concentration gradients are respectively 9,3,1,0.33,0.11 and 0 mu M. The sample is diluted to 200 μ M by culture solution, and then 3 times of dilution is carried out in sequence, and 6 concentrations are obtained, namely, the concentration gradients are respectively 200,67,22,7.4,2.5 and 0 μ M. The culture medium was aspirated and 100. mu.L of samples of different concentrations were added to each well in sequence. The plates were incubated at 37 ℃ in 5% CO2After 48h incubation in the incubator, the sample-containing medium was aspirated, and MTT solution (0.5mg/mL), 100. mu.L/well, was added. Placing into incubator for further culturing for 4h, absorbing culture solution containing MTT, adding DMSO, adding 100 μ L/well, shaking at low speed for 10min, and measuring OD value of each well at 490nm wavelength with microplate reader. According to the formula of inhibition ratio
Compounds were evaluated for in vitro anti-tumor activity.
3. Results of the experiment
The results are shown in Table 5, and show that the dihydrofuranone derivatives have good cytotoxic activity and IC activity on HepG2 cell lines and human embryonic liver cells L02 as shown by the cytotoxic activity experiments on human A549, PC-3, MCF-7, HepG2 and L0250The values were 101.7. mu.M and 57.83. mu.M, respectively.
TABLE 5 antitumor Activity of dihydrofuranone derivatives
Claims (10)
1. A dihydrofuranone derivative having a chemical formula:
2. a method for extracting a dihydrofuranone derivative according to claim 1, comprising:
step (1): extracting solid fermentation products of the cat-tail endophytic fungi DS37 serving as raw materials with petroleum ether, ethyl acetate and methanol for a plurality of times respectively, combining extracting solutions, filtering, recovering a mixed solvent, and concentrating the filtered extracting solution under reduced pressure to obtain a crude extract, wherein the mass ratio of the solid fermentation products of the cat-tail endophytic fungi DS37 to the crude extract is 92: 15;
step (2): eluting the crude extract obtained in the step (1) on a silica gel chromatographic column by using petroleum ether/ethyl acetate/methanol eluent with the volume gradient of 1:0:0,0:1:0,0:1:1,0:0:1 respectively to obtain a petroleum ether phase component A, an ethyl acetate phase component B, an ethyl acetate/methanol phase component C and a methanol phase component D respectively; the mass ratio of the crude extract to the components A, B, C and D is 150:11:42:70: 10; the volume ratio of ethyl acetate to methanol in the component C is 1: 1;
and (3): eluting the component B obtained in the step (2) on a silica gel chromatographic column by using petroleum ether/ethyl acetate eluent with the volume gradient of 100:0,100:20,100:50,100:100,100:200 and 0:100 respectively to obtain six components B1-B6; continuously eluting the component B4 on a silica gel chromatographic column by using petroleum ether/ethyl acetate eluent with the volume gradient of 100:0,100: 25, 100:50,100: 70, 100:90, 100:100,100: 130, 100:150, 100:180, 100:200 and 0:100 to obtain eleven components B4-1-B4-11; eluting the component B4-6 with petroleum ether-ethyl acetate eluent with the volume gradient of 100:25, 100:45, 100:65, 100:85, 100:105, 100:125, 100:145, 100:165, 100:185 and 100:205 to obtain ten components B4-6-1-B4-6-10, wherein the component B4-6-3 is recrystallized to obtain a dihydrofuranone derivative; the mass ratio of the component B to the component B4 is 21:1, the mass ratio of the component B4 to the component B4-6 is 20:3.7, and the mass ratio of the component B4-6 to the dihydrofuranone derivative is 1480: 17.
3. The method for extracting dihydrofuranone derivative according to claim 2, wherein the fermented solid product of the c.ranunculi chenne endophytic fungus DS37 is extracted with petroleum ether/ethyl acetate/methanol 8 times in step (1).
4. The method of claim 2, wherein the petroleum ether, ethyl acetate and methanol are all industry standards.
5. Use of the dihydrofuranone derivative according to claim 1 or the dihydrofuranone derivative prepared by the method according to any one of claims 2 to 4 for antibacterial drugs, antioxidant activities and antitumor drugs.
6. Use of dihydrofuranone derivatives according to claim 5, wherein the inhibition of bacteria or fungi is indicated.
7. Use of a dihydrofuranone derivative according to claim 6, wherein the inhibitory effect is against Gibberella tritici, Alternaria nicotianae, Phytophthora capsici and Botrytis cinerea.
8. Use of a dihydrofuranone derivative according to claim 5, wherein the antioxidant activity is against 1, 1-diphenyl-2-trinitrophenylhydrazine.
9. The use of a dihydrofuranone derivative according to claim 5, wherein the anti-tumor agent is an in vitro effect on human lung cancer cells, human prostate cancer cells, human breast cancer cells, human liver cancer cells, and human embryonic liver cells.
10. The use of dihydrofuranone derivatives according to claim 9, wherein the antitumor activity is against HepG2 and L02 cell lines in vitro.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210193134.4A CN114560831A (en) | 2022-02-28 | 2022-02-28 | Dihydrofuranone derivative and extraction method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210193134.4A CN114560831A (en) | 2022-02-28 | 2022-02-28 | Dihydrofuranone derivative and extraction method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114560831A true CN114560831A (en) | 2022-05-31 |
Family
ID=81715857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210193134.4A Withdrawn CN114560831A (en) | 2022-02-28 | 2022-02-28 | Dihydrofuranone derivative and extraction method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114560831A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108265007A (en) * | 2017-12-18 | 2018-07-10 | 国家海洋局第三海洋研究所 | The application of deep-sea fungi 3A00421 and its fermented cpds |
| CN111559999A (en) * | 2020-03-05 | 2020-08-21 | 陕西科技大学 | Lactone compound and extraction method and application thereof |
-
2022
- 2022-02-28 CN CN202210193134.4A patent/CN114560831A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108265007A (en) * | 2017-12-18 | 2018-07-10 | 国家海洋局第三海洋研究所 | The application of deep-sea fungi 3A00421 and its fermented cpds |
| CN111559999A (en) * | 2020-03-05 | 2020-08-21 | 陕西科技大学 | Lactone compound and extraction method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 王宁宁: "猫儿屎内生真菌DS37次生代谢产物的研究", 《中国优秀硕士学位论文全文数据库（电子期刊）》, no. 09, pages 018 - 74 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | Promoting role of an endophyte on the growth and contents of kinsenosides and flavonoids of Anoectochilus formosanus Hayata, a rare and threatened medicinal Orchidaceae plant | |
| Han et al. | Isolation and characterisation of the sesquiterpene lactones from Lactuca sativa L var. anagustata | |
| CN108892658B (en) | Compound lithocarpinol B, preparation method thereof and application thereof in preparation of antifungal drugs | |
| CN111559999B (en) | Lactone compound and extraction method and application thereof | |
| WO2022088912A1 (en) | Compound for controlling plant pathogenic bacteria and use thereof | |
| CN108383824B (en) | Benzopyrone dimer and extraction method and application thereof | |
| CN111888273A (en) | Plant-derived natural bacteriostatic agent or preservative and application thereof | |
| CN109295122A (en) | A kind of Preparation method and use of E. exserta endogenetic fungus Chaetomium sp secondary metabolite | |
| Shawkey et al. | Biofunctional molecules from Citrullus colocynthis: An HPLC/MS analysis in correlation to antimicrobial and anticancer activities | |
| Yuan et al. | Isolation of an antibacterial substance from Mahonia fortunei and its biological activity against Xanthomonas oryzae pv. oryzicola | |
| Thippeswamy et al. | Evaluation of antimicrobial property of lichen-Parmelia perlata | |
| CN114560831A (en) | Dihydrofuranone derivative and extraction method and application thereof | |
| CN108503616B (en) | A kind of bicoumarin derivative and its extracting method and application | |
| CN107459474A (en) | A kind of alkaloid and its extracting method and application | |
| CN108383811B (en) | Furanone derivative and extraction method and application thereof | |
| CN107501072A (en) | Compound colletotriconeA and preparation method thereof and the application in antineoplastic is prepared | |
| CN106554340A (en) | The purposes and its isolation and purification method of monomeric compound in a kind of Caulis wisteriae sinensiss tumor | |
| CN109384823B (en) | Two piericins glucoside and application thereof in anti-renal cancer drugs | |
| CN108640896B (en) | A kind of Desertorin B and its extracting method and application | |
| AU2021104334A4 (en) | Phenanthroindolizidine alkaloid and preparation method thereof | |
| CN115650854B (en) | Integrin derivative, its preparation method and application in alpha-glucosidase inhibiting medicine | |
| CN115737664B (en) | Acer truncatum leaf extract with anti-inflammatory activity and preparation method thereof | |
| CN104059038A (en) | Sesquiterpene compounds and application thereof | |
| CN116496332B (en) | Labdane diterpenoid glycoside compound and preparation method thereof | |
| CN111869671B (en) | Application of trihydroxybenzoic acid substituted monoterpene glycoside compounds in resisting phytopathogen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20220531 |