CN105211083A - A kind of application of Cyclic dipeptides Cyclo-(L-Ile-L-Pro) - Google Patents
A kind of application of Cyclic dipeptides Cyclo-(L-Ile-L-Pro) Download PDFInfo
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- CN105211083A CN105211083A CN201510755741.5A CN201510755741A CN105211083A CN 105211083 A CN105211083 A CN 105211083A CN 201510755741 A CN201510755741 A CN 201510755741A CN 105211083 A CN105211083 A CN 105211083A
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Abstract
The invention provides a kind of application of Cyclic dipeptides Cyclo-(L-Ile-L-Pro), this application is specially Cyclic dipeptides Cyclo-(L-Ile-L-Pro) and is preparing the application in nematode killer, by the mensuration of Meloidogyne incognita and Caenorhabditis elegans lethality rate, find that Cyclic dipeptides Cyclo-(L-Ile-L-Pro) has good killing effect to nematode, for the preparation of novel root-knot nematode biological prevention and control agent provides new selectivity.
Description
Technical field
The invention belongs to technical field of agricultural microbiology, be specifically related to a kind of application of Cyclic dipeptides Cyclo-(L-Ile-L-Pro).
Background technology
Plant nematode is that a class can parasitize each tissue of plant, causes plant to occur the cause of disease animal of illness.Mainly be divided into root-knot nematode, pine wood nematode, soy bean cyst roundworm and stem eelworm etc., the most serious with root-knot nematode harm, worldwide extensively distribute.Root-knot nematode can parasitic 3000 various plants, especially the Vegetables crop such as tomato, cucumber, peanut, and according to incomplete estimation, the economic loss that nematode is caused in the whole world is about 80,000,000,000.In the subtropical and tropical zones that root-knot nematode disease is serious, cause crop production reduction more than 80%.
Root-knot nematode belongs to obligatory parasitism, and what second instar larvae (J2) was root-knot nematode infects age.Usually invaded by the tip of a root of plant, host is stabbed with lancet, secretion noxious material, these materials contain multiple digestive ferment, bring out host tissue and various pathological change occurs, destroy the eubolism function of host cell, most typical symptom forms the different warty root knot of size shape, has multiple female worm in root knot.
Root-knot nematode host range is comparatively wide, and great majority are through sick soil, sick seedling and irrigate propagation, and pieces of an egg can be survived for a long time in soil, therefore administer more difficult.Mainly contain following several method at present: (1) cultural control: comprise rice field-upland field rotation, grafting, improvement soil, regulate sowing time, plantation disease-resistant variety etc.(2) physical control: mainly contain and carry out Soil Thermal process summer and seed eliminates choosing, also comprise water logging in addition more than two weeks, ray or ultrasonic process etc.(3) chemical control: use nematocide and remain the main method of preventing and treating root knot nematode disease at present, wherein Celfume soil disinfection occupies larger proportion in China, excellent to root knot nematode disease control efficiency.But Celfume has destruction to atmospheric ozone layer, some developed countries prohibit the use Celfume at present.(4) biological control: biological control is development in recent years more a kind of prevention and controls.The natural enemy of root-knot nematode mainly contains fungi, bacterium, virus, Rickettsial, actinomycetes, predatism nematode, turbellarian worm and protozoa etc., wherein more to the biological control Effect study of bacterium and fungi.
Cyclic dipeptides of the present invention (cyclicdipeptides), have another name called 2,5-dioxygen piperazidine (2,5-dioxopiperazines) or 2,5-diketopiperazine (2,5-diketopiperazines), being formed by peptide bond cyclization by two amino acid, is the minimum cyclic peptide of occurring in nature.The Cyclic dipeptides that occurring in nature exists generally forms metastable hexatomic ring by a-amino acid (normal is L-amino acid).Because ring two skin forms a stable six-membered ring structure, there is certain conformation effect of contraction, have two hydrogen-bond donors and two hydrogen bond receptors, hydrogen bond is one of major way of drug receptor interaction, and thus Cyclic dipeptides is an important pharmacophore in pharmaceutical chemistry.
Along with people are to the further investigation of Cyclic dipeptides, find that this compounds has multiple biologically active.Its stable hexatomic ring skeleton structure makes it in pharmaceutical chemistry, become an important pharmacophore; show multiple significant biologically active and the pharmacologically actives such as antibacterium, antimycotic, antiviral, antitumor, immunosupress, neuroprotective, anti-malarial, anti-prion, antihyperglycemic, also can be used as plant growth regulator, immunodepressant and immunopotentiator.The cyclo (Leu-Pro) reported and cyclo (Phe-Pro) has stronger inhibitory action to enterococcus faecalis.Cyclic dipeptides also has anticancer and antitumor action, and Merwe etc. find that Cyclo (Tyr-Cys) all has significant inhibit activities to cancer cell HT-29, HeLa and MCF-7.Be separated from the zymotic fluid of Cordyceps sinensis endogenetic fungus Epicoccumnigrum and obtain 3 kinds of CYCLIC DIPEPTIDES compounds and can suppress HIV-1 copying in C8166 cell.
Summary of the invention
A kind of Cyclic dipeptides Cyclo-(L-Ile-L-Pro) is the object of the present invention is to provide to prepare the application in nematode killer.Application particularly in Caenorhabditis elegans insecticide and/or meloidogyne pesticide.Described Cyclic dipeptides Cyclo-(L-Ile-L-Pro) molecular formula is C
11h
18n
2o
2, [M+H]+be m/z211.1449, molecular weight is 210.1449.This Cyclic dipeptides possesses eelworm-killing activity, and its chemical formula is as follows:
In order to reach above object, the present invention adopts following technical measures:
A kind of Cyclic dipeptides Cyclo-(L-Ile-L-Pro) is preparing the application in nematode killer, and application process comprises and is prepared into nematode killer with Cyclic dipeptides Cyclo-(L-Ile-L-Pro) for main effect component or for one of active ingredient.
Compared with prior art, the present invention has following characteristics:
1. reported first of the present invention Cyclo-(L-Ile-L-Pro) its eelworm-killing activity, for the preparation of novel root-knot nematode biological prevention and control agent provides new selectivity.
Accompanying drawing explanation
Fig. 1 is a kind of high-efficient liquid phase chromatogram killing nematode Cyclic dipeptides.
Fig. 2 is a kind of mass spectrogram killing nematode Cyclic dipeptides.
Fig. 3 is a kind of nuclear magnetic resonnance one dimension collection of illustrative plates killing nematode Cyclic dipeptides.
Fig. 4 is a kind of chemical constitution schematic diagram killing nematode Cyclic dipeptides.
Embodiment
Experimental technique in following embodiment, if no special instructions, is the microbiology conventional practices of report.
Embodiment 1:
Kill chemosynthesis and the structure verification of nematode Cyclic dipeptides
1. CYCLIC DIPEPTIDES material (Cyclo-(L-Ile-L-Pro)) is purchased from Tianjin Yaoming Kangde new drugs development Co., Ltd.
5. high performance liquid chromatography (HPLC)
Using 20% acetonitrile/water solution (v/v) as mobile phase, determined wavelength is 220nm, determines the purity of the Cyclic dipeptides material (Cyclo-(L-Ile-L-Pro)) of chemosynthesis, and experiment is carried out 3 times and repeated.
6. liquid phase-mass spectrometry (LC/MS)
The Cyclic dipeptides material (Cyclo-(L-Ile-L-Pro)) of Agilent6540 LC-MS system to chemosynthesis is adopted to carry out Preliminary Identification.Liquid-phase condition is as follows: mobile phase: 5%-90% acetonitrile/water solution (v/v) gradient elution; Flow velocity: 0.3mL/min; Sample size: 3 μ L; Determined wavelength 210nm; Mass Spectrometry Conditions: anion source ESI.Mass spectrometric data: [M+H]+be m/z211.1449, molecular weight is 210.1449, and molecular formula is C
11h
18n
2o
2.
7. nuclear magnetic resonnance (NMR)
Cyclic dipeptides material (Cyclo-(the L-Ile-L-Pro)) structure of magnetic resonance detection chemosynthesis: with heavy water (D2O) for solvent, measures two-dimensional spectrum such as carbon spectrum (13CNMR) and HSQC, COSY and HMBC etc. respectively.According to data analysis, this Cyclic dipeptides is Cyclo-(L-Ile-L-Pro).Table 1 is nuclear magnetic resonance data.
Table 1Cyclo-(L-Ile-L-Pro) Two-dimensional NMR Map data
Embodiment 2:
The Nematicidal Activity of Cyclic dipeptides material (Cyclo-(L-Ile-L-Pro))
1. Nematicidal Activity method
(1) biological activity determination experiment is carried out with 96 orifice plates;
(2) after every hole adds 200ul filtration sterilization, concentration is Cyclic dipeptides solution and about 30 root-knot nematodes of 800 μ g/mL;
(3) often organize Setup Experiments three repetition, and 2 groups of blanks are set with sample solvent, be designated as CK;
(4) 20 DEG C of incubators are cultivated, and observe and add up lethality every 24h;
2. the contact toxicity of Cyclic dipeptides to Caenorhabditis elegans and root-knot nematode measures
According to above-mentioned method, sample is added 96 orifice plates, the sample of each concentration arranges 3 repetitions, using sterile water as negative control.Observe under inverted microscope at 48h, 72h and 96h respectively, nematode judges anyway to be judged to be death with tactile motionless of pin.Improved mortality formula:
3. Cyclic dipeptides Nematicidal Activity result
Table 2 Cyclic dipeptides is to Caenorhabditis elegans determination of activity
Table 3 Cyclic dipeptides Cyclo-(L-Ile-L-Pro) is to Meloidogyne incognita determination of activity
Note: in table, numerical value is the mean value repeating for 3 times to test; Control group is sterile water
Embodiment 3:
The suppression pathogenic bacteria of Cyclic dipeptides material (Cyclo-(L-Ile-L-Pro)), conk determination of activity
1. suppress pathogenic bacteria growth activity to measure
(1) activity checking is carried out with dull and stereotyped face-off experiment;
(2) after every hole adds 30ul filtration sterilization, concentration is the Cyclic dipeptides solution of 100 μ g/mL;
(3) often organize Setup Experiments three repetition, and 3 groups of blanks are set with sample solvent, be designated as CK;
(4) 37 DEG C of incubators are cultivated, and observe antibacterial result after 24h.
2. suppress pathogenic bacteria growth activity to measure
(1) activity checking is carried out with dull and stereotyped face-off experiment;
(2) after every hole adds 30ul filtration sterilization, concentration is the Cyclic dipeptides solution of 100 μ g/mL;
(3) often organize Setup Experiments three repetition, and 3 groups of blanks are set with sample solvent, be designated as CK;
(4) 28 DEG C of incubators are cultivated, when conk extends to whole flat board, and statistical experiment result.
3. Cyclic dipeptides suppresses pathogenic bacteria, conk determination of activity result
The determination of activity of table 4 Cyclic dipeptides Cyclo-(L-Ile-L-Pro) bacteria growing inhibiting
Note: NE (noeffect) represents do not have effect
Table 5 Cyclic dipeptides Cyclo-(L-Ile-L-Pro) Antifungi growth activity measures
Note: NE (noeffect) represents do not have effect.
Claims (5)
1. a Cyclic dipeptides Cyclo-(L-Ile-L-Pro) is preparing the application in nematode killer.
2. application according to claim 1, described Cyclic dipeptides is preparing the application in nematode killer as main effect component.
3. application according to claim 1, described Cyclic dipeptides is preparing the application in nematode killer as sole active ingredient.
4. the nematode killer described in application according to claim 1 is Meloidogyne incognita insecticide or Caenorhabditis elegans insecticide.
5. a Cyclic dipeptides Cyclo-(L-Ile-L-Pro) is preparing the application simultaneously killed in Meloidogyne incognita and Caenorhabditis elegans insecticide.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107624768A (en) * | 2017-08-21 | 2018-01-26 | 华南农业大学 | Applications of Cyclic dipeptides cyclo (S) pro (R) Ile in bacterial wilt is prevented and treated |
| CN113678837A (en) * | 2021-08-23 | 2021-11-23 | 王文明 | Plant extract slow-release insect-resist agent and preparation method thereof |
| CN114539354A (en) * | 2020-11-26 | 2022-05-27 | 西南科技大学 | Nematicidal cyclopeptide compound and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0543408A (en) * | 1991-08-09 | 1993-02-23 | Nippon Zoki Pharmaceut Co Ltd | Agent for imparting resistance to stress |
| CN1074936A (en) * | 1992-01-24 | 1993-08-04 | Fmc有限公司 | Insecticidally effective peptides |
| KR20110120051A (en) * | 2010-04-28 | 2011-11-03 | 공주대학교 산학협력단 | Process for preparing 2,5-diketopiperazine compounds |
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2015
- 2015-11-09 CN CN201510755741.5A patent/CN105211083B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0543408A (en) * | 1991-08-09 | 1993-02-23 | Nippon Zoki Pharmaceut Co Ltd | Agent for imparting resistance to stress |
| CN1074936A (en) * | 1992-01-24 | 1993-08-04 | Fmc有限公司 | Insecticidally effective peptides |
| KR20110120051A (en) * | 2010-04-28 | 2011-11-03 | 공주대학교 산학협력단 | Process for preparing 2,5-diketopiperazine compounds |
Non-Patent Citations (1)
| Title |
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| 汪蕾等: "共生真菌巴西类壳小圆孢中环二肽类代谢物研究进展", 《化学研究与应用》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107624768A (en) * | 2017-08-21 | 2018-01-26 | 华南农业大学 | Applications of Cyclic dipeptides cyclo (S) pro (R) Ile in bacterial wilt is prevented and treated |
| CN107624768B (en) * | 2017-08-21 | 2020-07-03 | 华南农业大学 | Application of cyclic dipeptide cyclo- (S) -pro- (R) -Ile in preventing and treating bacterial wilt |
| CN114539354A (en) * | 2020-11-26 | 2022-05-27 | 西南科技大学 | Nematicidal cyclopeptide compound and preparation method thereof |
| CN114539354B (en) * | 2020-11-26 | 2024-04-26 | 西南科技大学 | Nematicidal cyclopeptide compound and preparation method thereof |
| CN113678837A (en) * | 2021-08-23 | 2021-11-23 | 王文明 | Plant extract slow-release insect-resist agent and preparation method thereof |
| CN113678837B (en) * | 2021-08-23 | 2022-12-02 | 王文明 | Plant extract slow-release insect-resist agent and preparation method thereof |
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| CN105211083B (en) | 2017-03-29 |
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