CN105211083B - 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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- CN105211083B CN105211083B CN201510755741.5A CN201510755741A CN105211083B CN 105211083 B CN105211083 B CN 105211083B CN 201510755741 A CN201510755741 A CN 201510755741A CN 105211083 B CN105211083 B CN 105211083B
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Abstract
The invention provides a kind of application of Cyclic dipeptides Cyclo (L Ile L Pro), applications of the application specially Cyclic dipeptides Cyclo (L Ile L Pro) in nematode killer is prepared, by Meloidogyne incognita and the measure of Caenorhabditis elegans fatality rate, it was found that Cyclic dipeptides Cyclo (L Ile L Pro) has preferable killing effect to nematicide, the preparation for new root-knot nematode biological prevention and control agent provides new selectivity.
Description
Technical field
The invention belongs to technical field of agricultural microbiology, and in particular to a kind of Cyclic dipeptides Cyclo- (L-Ile-L-Pro)
Application.
Background technology
Plant nematode be a class can parasitize plant each tissue, cause plant the cause of disease animal of disease occur.
Root-knot nematode, Bursaphelenchus xylophilus, soy bean cyst roundworm and Ditylenchus dipsaci etc. are broadly divided into, endanger the most serious with root-knot nematode, it is alive
It is widely distributed in the range of boundary.Root-knot nematode can be with parasitic 3000 various plants, the especially Vegetables such as Fructus Lycopersici esculenti, Fructus Cucumidis sativi, Semen arachidis hypogaeae
Crop, according to not exclusively estimation, the economic loss that nematicide is caused in the whole world is 80,000,000,000 or so.In the serious heat of root-knot nematode disease
Band and subtropical zone, cause crop production reduction more than 80%.
Root-knot nematode belongs to obligatory parasitism, and second instar larvae (J2) infects age for root-knot nematode.Generally by the tip of a root of plant
Invade, host is stabbed with lancet, secrete noxious substance, these materials contain various digestive enzyme, and induction host tissue occurs various
Pathological change, destroys the homergy function of host cell, and most typical symptom is to form the different warty root knot of size shape,
There are multiple female adults in root knot.
Root-knot nematode host range is wider, and great majority are Jing sick soils, sick seedling and irrigate propagation, and pieces of an egg can be deposited in soil
Live for a long time, therefore administer relatively difficult.Mainly there is following several method at present：(1) cultural control：Including rice field-upland field rotation, grafting,
Improved soil, regulation sowing time, plantation disease-resistant variety etc..(2) physical control：Mainly there is summer to carry out soil heat treatment and seed
Choosing is eliminated, water logging more than two weeks, ray or ultrasonic Treatment etc. is additionally included.(3) chemical prevention：Apply nematicide to remain
The main method of root knot nematode disease is prevented and treated at present, and wherein bromomethane soil disinfection occupies larger proportion in China, to vegetable root knot
Nematicide prevention effect is excellent.But bromomethane has destruction to atmospheric ozone layer, some developed countries have forbidden at present
Using bromomethane.(4) Biological control：Biological control is to develop a kind of relatively rapid prevention and controls in recent years.The day of root-knot nematode
Enemy mainly has funguses, antibacterial, virus, Rickettsial, actinomycetes, predatism nematicide, turbellarian worm and protozoacide etc., wherein to antibacterial
It is more with the Biological control Effect study of funguses.
Cyclic dipeptides (cyclic dipeptides) of the present invention, also known as 2,5- dioxygen piperazidine (2,5-
Dioxopiperazines) or 2,5- diketopiperazine (2,5-diketopiperazines), passes through peptide bond ring by two aminoacid
Close and formed, be the cyclic peptide of minimum in nature.Cyclic dipeptides present in nature are typically by a-amino acid (being often l-amino acid)
Form metastable hexatomic ring.As two skin of ring forms a stable six-membered ring structure, make with certain conformation constraint
With, there are two hydrogen-bond donors and two hydrogen bond receptors, hydrogen bond is one of major way of drug receptor interaction, thus ring
Dipeptides is an important pharmacophore in pharmaceutical chemistry.
With further investigation of the people to Cyclic dipeptides, it is found that such compound has multiple biological activities.Which stable six
Membered ring skeleton structure makes which become an important pharmacophore in pharmaceutical chemistry, shows antibacterium, antifungal, disease-resistant
Various significant biological activitys such as poison, antitumor, immunosuppressant, neuroprotective, malaria, anti-prion, hyperglycemia and medicine
Reason activity, is alternatively arranged as plant growth regulator, immunosuppressant and immunostimulant.The cyclo (Leu-Pro) that reported and
Cyclo (Phe-Pro) has stronger inhibitory action to enterococcus faecalis.Cyclic dipeptides also have anticancer and antitumor action, Merwe
There is significant inhibitory activity to cancerous cell HT-29, HeLa and MCF-7 Deng discovery Cyclo (Tyr-Cys).From in Cordyceps
In the fermentation liquid of raw funguses Epicoccum nigrum, isolated 3 kinds of CYCLIC DIPEPTIDES compounds can suppress HIV-1 thin in C8166
Duplication in born of the same parents.
The content of the invention
It is an object of the invention to provide a kind of Cyclic dipeptides Cyclo- (L-Ile-L-Pro) is in nematode killer is prepared
Using.Application particularly in Caenorhabditis elegans insecticide and/or meloidogyne pesticide.Described Cyclic dipeptides Cyclo-
(L-Ile-L-Pro) molecular formula is C11H18N2O2, [M+H]+it is m/z 211.1449, molecular weight is 210.1449.The Cyclic dipeptides
Possesses eelworm-killing activity, its chemical formula is as follows：
In order to reach object above, the present invention adopts following technical measures：
A kind of application of Cyclic dipeptides Cyclo- (L-Ile-L-Pro) in nematode killer is prepared, application process include with
Cyclic dipeptides Cyclo- (L-Ile-L-Pro) is prepared into nematode killer for main effect component or for one of effective ingredient.
Compared with prior art, the invention has the characteristics that：
1. reported first of the present invention Cyclo- (L-Ile-L-Pro) its eelworm-killing activity, is new root-knot nematode life
The preparation of anti-preparation is there is provided new selectivity.
Description of the drawings
Fig. 1 is a kind of high-efficient liquid phase chromatogram of nematicide Cyclic dipeptides.
Fig. 2 is a kind of mass spectrum of nematicide Cyclic dipeptides.
Fig. 3 is a kind of one-dimensional collection of illustrative plates of nuclear magnetic resonance, NMR of nematicide Cyclic dipeptides.
Fig. 4 is a kind of chemical constitution schematic diagram of nematicide Cyclic dipeptides.
Specific embodiment
Experimental technique in following embodiments, if no special instructions, is the microbiology conventional practices of report.
Embodiment 1：
The chemosynthesis of nematicide Cyclic dipeptides and structure verification
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, Detection wavelength is 220nm, determines the Cyclic dipeptides of chemosynthesis
The purity of material (Cyclo- (L-Ile-L-Pro)), experiment carry out 3 repetitions.
6. liquid phase-mass spectrometry (LC/MS)
Using Cyclic dipeptides material (Cyclo- (L-Ile-L- of the 6540 LC-MS systems of Agilent to chemosynthesis
Pro)) carry out Preliminary Identification.Liquid-phase condition is as follows：Mobile phase：5%-90% acetonitrile/water solution (v/v) gradient elutions；Flow velocity：
0.3mL/min；Sample size：3μL；Detection wavelength 210nm；Mass Spectrometry Conditions：Anion source ESI.Mass spectrometric data：[M+H]+it is m/z
211.1449, molecular weight is 210.1449, and molecular formula is C11H18N2O2。
7. nuclear magnetic resonance, NMR (NMR)
Cyclic dipeptides material (Cyclo- (the L-Ile-L-Pro)) structure of magnetic resonance detection chemosynthesis：With heavy water (D2O)
For solvent, the carbon spectrum two-dimensional spectrum such as (13C NMR) and HSQC, COSY and HMBC is determined respectively.According to data analysiss, the ring two
Peptide is Cyclo- (L-Ile-L-Pro).Table 1 is nuclear magnetic resonance data.
Table 1 Cyclo- (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 adding 200ul filtration sterilizations per hole, concentration is the Cyclic dipeptides solution and 30 or so root knot lines of 800 μ g/mL
Worm；
(3) three repetitions of every group of Setup Experiments, and 2 groups of blanks are set with sample solvent, it is designated as CK；
(4) 20 DEG C of incubators are cultivated, and are observed every 24h and are counted mortality rate；
2. Cyclic dipeptides are determined to the contact toxicity of Caenorhabditis elegans and root-knot nematode
According to above-mentioned method, the sample that sample adds 96 orifice plates, each concentration is arranged into 3 repetitions, is made with sterilized water
For negative control.Observe under inverted microscope in 48h, 72h and 96h respectively, nematicide judges the motionless judgement touched with pin anyway
For death.Improved mortality formula：
3. Cyclic dipeptides Nematicidal Activity result
2 Cyclic dipeptides of table are to Caenorhabditis elegans determination of activity
3 Cyclic dipeptides Cyclo- (L-Ile-L-Pro) of table is to Meloidogyne incognita determination of activity
Note:In table, numerical value is the meansigma methodss of 3 repetition experiments；Matched group is sterilized water
Embodiment 3：
The suppression pathogenic bacteria of Cyclic dipeptides material (Cyclo- (L-Ile-L-Pro)), funguses growth activity are determined
1. suppress pathogenic bacteria growth activity to determine
(1) active checking is carried out with flat board face-off experiment；
(2) after adding 30ul filtration sterilizations per hole, concentration is the Cyclic dipeptides solution of 100 μ g/mL；
(3) three repetitions of every group of Setup Experiments, and 3 groups of blanks are set with sample solvent, it is designated as CK；
(4) 37 DEG C of incubators are cultivated, and antibacterial result is observed after 24h.
2. suppress pathogenic bacteria growth activity to determine
(1) active checking is carried out with flat board face-off experiment；
(2) after adding 30ul filtration sterilizations per hole, concentration is the Cyclic dipeptides solution of 100 μ g/mL；
(3) three repetitions of every group of Setup Experiments, and 3 groups of blanks are set with sample solvent, it is designated as CK；
(4) 28 DEG C of incubators are cultivated, when funguses growth extends to whole flat board, statistical experiment result.
3. Cyclic dipeptides suppress pathogenic bacteria, funguses growth activity measurement result
4 Cyclic dipeptides Cyclo- (L-Ile-L-Pro) bacteria growing inhibiting determination of activity of table
Note：NE (no effect) represents do not have effect
5 Cyclic dipeptides Cyclo- (L-Ile-L-Pro) of table suppresses funguses growth activity to determine
Note：NE (no effect) represents do not have effect.
Claims (4)
1. application of a kind of Cyclic dipeptides Cyclo- (L-Ile-L-Pro) in nematode killer is prepared, described nematode killer
For Meloidogyne incognita insecticide or Caenorhabditis elegans insecticide.
2. application according to claim 1, described Cyclic dipeptides as main effect component in nematode killer is prepared should
With.
3. application according to claim 1, described Cyclic dipeptides are as sole active ingredient in nematode killer is prepared
Application.
4. a kind of Cyclic dipeptides Cyclo- (L-Ile-L-Pro) is being prepared while killing Meloidogyne incognita and Caenorhabditis elegans are killed
Application in worm agent.
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| 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 |
| CN114539354B (en) * | 2020-11-26 | 2024-04-26 | 西南科技大学 | Nematicidal cyclopeptide compound 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1074936A (en) * | 1992-01-24 | 1993-08-04 | Fmc有限公司 | Insecticidally effective peptides |
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| JPH0543408A (en) * | 1991-08-09 | 1993-02-23 | Nippon Zoki Pharmaceut Co Ltd | Agent for imparting resistance to stress |
| KR101191977B1 (en) * | 2010-04-28 | 2012-10-17 | 대한민국(관리부서:농촌진흥청장) | Process for preparing 2,5-diketopiperazine compounds |
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| CN1074936A (en) * | 1992-01-24 | 1993-08-04 | Fmc有限公司 | Insecticidally effective peptides |
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| 共生真菌巴西类壳小圆孢中环二肽类代谢物研究进展;汪蕾等;《化学研究与应用》;20141231;第26卷(第9期);第1478-1482页 * |
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