CN104823978B - Flavone compound theaflavanoside IV application on preventing and treating plant nematode diseases - Google Patents
Flavone compound theaflavanoside IV application on preventing and treating plant nematode diseases Download PDFInfo
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Abstract
The present invention relates to flavone compound theaflavanoside IV application on preventing and treating plant nematode diseases, shown in the structure such as formula (1) of flavone compound theaflavanoside IV。Cyst roundworm, root-knot nematode, Pratylenchidae, aphelenchoides besseyi are all had strong cytotoxicity by flavone compound theaflavanoside IV, particularly that the virulence of root-knot nematode is very strong。Flavone compound theaflavanoside IV of the present invention derives from natural plants, it is prone to degraded in the environment, therefore compared with nematocide, there is the characteristic of low toxicity and low residue, being compatible with the environment property is better, meets environment protective plant protecting and sustainable agriculture produces and the needs of development。
Description
Technical field
The present invention relates to flavone compound theaflavanosideIV (molecular formula C38H50O23) in the purposes prevented and treated on plant nematode diseases。
Background technology
Plant nematode is one of plant important pathogen biology, and along with agricultural is to industrialization, Base environment develops, long-term establishing in large scale monoculture, and the raising of continuous cropping throughout the year and soil recycling rate of waterused, nematicide quantity in soil is accumulated rapidly, and nematodiasis problem becomes increasingly conspicuous。In the northern area of China, Semen Tritici aestivi cyst roundworm (Heterodera.avenarea, H.filipjevi), soy bean cyst roundworm (Heteroderaglycines) generally occurs and endangers serious, the production of China's Semen Tritici aestivi and Semen sojae atricolor is caused heavy losses and impact (Peng Deliang etc., Peng Deliang, Zhang Dongsheng, Qi Shuhua, Chen Pinsan. wheat cearal cyst nematode the best investigation period and method. plant protection, 1993, 19 (5): 48, Peng Deliang, Li Huixia, Wang Xifeng, IanRelay, JulieNicol, Hou Shengying, Ou Shiqi. the kainogenesis Distribution Area of China's wheat cearal cyst nematode. China's nematology research (volume Two), 2008, 2:344-345；Peng Deliang, Huang Wenkun, Sun Jianhua, Liu Chongjun, Zhang Huimin. China Tianjin finds wheat cearal cyst nematode. China's nematology research (Volume Four), 2012,4:162-163；
Peng Deliang, Huang Wenkun, Sun Jianhua, Liu Chongjun, Zhang Huimin. China Tianjin finds wheat cearal cyst nematode. China's nematology research (Volume Four), 2012,4:162-163；Feng Zhixin. plant nematology (M). Beijing: Chinese agriculture publishing house, 2001), on the vegetable of southern area, fruit tree, root-knot nematode (Meloidogyne) occurs generally and quite serious, In Guangdong Province is owing to being in Delta of the Pearl River area, soil mostly is sandy loam, being particularly suitable for the growth promoter of Plant nematode, therefore nematodiasis problem is more prominent。Northern area adopts booth to produce vegetable now, and root-knot nematode disease is also fairly common and serious。Nematode killing agent is one of effective measures preventing and treating nematodiasis at present, but current nematocide is high poison persistent pesticide, very easily cause the pollution to crops and ecological environment, and the biological pesticide avermectin that toxicity is relatively low at present also occurs in that resistance problems on producing。Therefore seeking new, polytype Biological control nematode killing agent, is one of the study hotspot preventing and treating crops nematodiasis at present。
Plant be bioactive compound natural treasure-house, directly natural product (Herb or certain part such as plant) is processed into preparation in order to control insect (such as rotenone, nimbin), or at fully research natural plant active insecticidal components, structure activity relationship, on the basis of poisoning mechanism, the high-efficient low toxicity insecticide that analog synthesis is new, this has had very successful precedent (research and development such as pyrethroid pesticide) in vegetable insecticide, in contrast to this, the research of Botanical nematocide is relatively backward, until after the eighties in 20th century, the research finding natural nematocidal active material from plant just starts (the Wen Yanhua that receives publicity, Feng Zhixin, Xu Hanhong. several plant pathogenic nematode is killed line screening active ingredients [J] by Plant crude extract. Hua Zhong Agriculture University's journal, 2001, 20 (3): 235-238.), the Chinese invention patent that publication number is CN201210050127.5 discloses the tea saponin prevention and controls to root knot nematode, application number be 2014103322825 patent application disclose tea saponin preventing and treating soybean cyst nematode evil on application；The Chinese invention patent of publication number 1660848 discloses the application of Folium et Ramulus Cephalotaxi aconitines preventing and treating plant nematode diseases, but yet there are no the flavone compound patent to Plant nematode control and application。
Flavonoid (flavonoid) compound is widely present in various plants and the berry of nature, referring to two phenyl ring (A, B ring) with phenolic hydroxyl group and pass through a series of compounds that central authorities' thricarbon atom is interconnected, its basic parent nucleus is 2-phenyl chromone。Current isolated flavone compound is more than 4000 kinds, and minority exists with free state, mostly combine with sugar with the form of flavonoid glycoside exist (Yang Hong. Chemistry for Chinese Traditional Medicine practical technique [M]. Beijing: Chemical Industry Press, 2004)。Flavone compound has protection cardiovascular and cerebrovascular vessel, antitumor, antioxidation, anti-inflammatory, antibacterial antiviral, scavenging activated oxygen, reduce cholesterol and regulate the pharmacologically active (BentH such as immunity, Havsteen.Thebioehemistryandmediealsignifieaneeoftheflavo noids [J] .Pharmacology&TheraPeuties, 2002, 96:67-202), and toxicity is relatively low, therefore in recent years, flavone compound becomes domestic and international natural drug, natural additive, exploitation study hotspot (the Dong Caijun in the fields such as health product exploitation, Li Feng. the progress [J] of flavone compound. processing of farm products, 2010, 2 (2): 65-69.)。Flavone in Semen Camelliae has many medical actives。Zhang Naifeng etc. add the tea seed cake flavone of 300mg/kg in the concentrate supplement of Poll Dorset, and compared with matched group, the weightening finish of experimental group lamb improves 9.8 percentage points, and respiratory tract disease decreases 64%；Experimental group is bred as the weightening finish of sheep and improves 6.1 percentage points, respiratory tract disease decrease 50% (Zhang Naifeng, Zhang Zhonglun, Diao Qiyu etc. the impact [J] on gaining in weight of lamb and health status of the tea flavone. modern farming enterprise's veterinary, 2005,8:18-19.)；Feng Meng etc. add vine tea flavone in laying hen word material, long-term eating is free from side effects, do not have medicine residual, and there is the effect of bacteriostasis and sterilization, and can improve the survival rate of laying hen and laying rate (Feng Meng, Zhou Jian, Huang Yexian. the vine tea flavone impact [J] on the blue performance in layers in sea. feedstuff and herding, 2008,40 (1): 48-50)。
Flavone compound theaflavanosideIV (molecular formula C in the present invention38H50O23) be this laboratory from Theaceae (Camelliaceae) plant oil tea (CameferaOleifera)) and seed extraction separation and purification and obtain, this compound was extracted from the seed of Flos Camelliae Japonicae (Camelliasinensis) by LiNing etc. first in 2007 and obtains and report (LiN, MorikawaT, MatsudaH, etal.Newflavanoneoligoglycosides, theaflavanosidesI, II, III, andIV, withhepatoprotectiveactivityfromtheseedsofteaplant (Camelliasinensis) [J] .Heterocycles.2007, 71 (5): 1193-1201.)。This flavone compound yet there are no the Effect study to nematicide。The structural formula of this compound is shown in described in (1):
This compound be prepared by with the seed of plant of theaceae for material, adopt conventional known method, i.e. organic solvent extraction, macroporous resin, silica gel column chromatography separate, high performance liquid chromatography separation purification, carry out the raw survey of eelworm-killing activity, thus obtaining flavonoid monomer compound theaflavanosideIV (the molecular formula C with strong eelworm-killing activity simultaneously38H50O23).
Summary of the invention:
It is an object of the invention to the new application of the flavone compound theaflavanosideIV of exploitation above-claimed cpd (1), namely for preventing and treating the new application of plant nematode diseases。
Flavone compound theaflavanosideIV as nematicide effective ingredient preventing and treating plant nematode diseases in application, shown in the structure of flavone compound theaflavanosideIV such as formula (1)。
Described Plant nematode is cyst roundworm, root-knot nematode, Pratylenchidae, aphelenchoides besseyi。
Described cyst roundworm is Semen Tritici aestivi cyst roundworm (Heterodera.avenarea) or soy bean cyst roundworm (Heteroderaglycines)。
Described application is flavone compound theaflavanosideIV to make pesticide impose on morbidity plant surface or root。
Described preventing and treating plant nematode diseases is for suppressing line eggs hatching or killing Plant nematode and effectively reduce nematode infection。
Flavone compound theaflavanosideIV described in the compounds of this invention (1) is as effective ingredient, add in agriculture pharmaceutical carrier or compositions, make pesticide, it is possible to adopt the common formulations of pesticide and using method, be used for preventing and treating plant nematode diseases。Or the camellia oleosa seed extract containing this composition, extractive part (such as camellia oleosa seed flavone), separated part are added in agriculture pharmaceutical carrier or compositions, makes pesticidal preparations, be used for preventing and treating plant nematode diseases。The common formulations of pesticide and using method can be adopted。
Plant nematode is had strong cytotoxicity by the flavone compound theaflavanosideIV described in compound (1), the raw result of surveying of the indoor cytotoxicity of Semen Tritici aestivi cyst roundworm (Heterodera.avenarea) is shown, processing 36h, the lethal concentration of 50 to Semen Tritici aestivi cyst roundworm is LC50=9.06 μ g/ml, process 36h, and the lethal concentration of 50 to soy bean cyst roundworm (Heteroderaglycines) is LC50=213.92 μ g/ml, indoor biometrics, process the lethal concentration of 50 respectively LC of Meloidogyne incognita second instar larvae 24h and 48h50=81.21 μ g/ml and LC50=50.77 μ g/ml, the hatching of Meloidogyne incognita ovum there is very strong inhibitory activity, illustrate that cyst roundworm and root-knot nematode are respectively provided with strong cytotoxicity by flavone compound theaflavanosideIV, especially root-knot nematode is had very strong cytotoxicity and egg hatching inhibitory activity。
Advantages of the present invention:
1) flavone compound theaflavanosideIV of the present invention derives from the seed of Theaceae, also has a small amount of existence, it was demonstrated that human body is safer in Folium Camelliae sinensis。
2) indoor biometrics and control in field result of study show, cyst roundworm, root-knot nematode, Pratylenchidae, aphelenchoides besseyi are all had strong cytotoxicity by flavone compound theaflavanosideIV, particularly that the virulence of root-knot nematode is very strong。
3) flavone compound theaflavanosideIV of the present invention derives from natural plants, it is prone to degraded in the environment, therefore compared with nematocide, there is the characteristic of low toxicity and low residue, being compatible with the environment property is better, meets environment protective plant protecting and sustainable agriculture produces and the needs of development。
Detailed description of the invention:
Tests below and operation are further illustrating the present invention, and should not regard limitation of the present invention。
Embodiment 1: the preparation of the flavone compound theaflavanosideIV described in compound (1)
The Semen Camelliae plant disintegrating machine of the residue (tea seed cake) after oil expression smashes, and crosses 40 mesh sieves, soaks with the edible ethanol of the 8 of sample size times of (w/v) 95%, and In Shade, period stirs often。Filtering after 5-7d, residue adds soak with ethanol again, twice repeatedly, merging filtrate。Ethanol filtrate is reduced pressure on a rotary evaporator, less than 45 DEG C concentrations, then use petroleum ether extraction 3 times, remove the unnecessary oils and fats in material。In solution after extracting defat, addition is the hydrogen peroxide of 3%, and regulating pH value is 10, puts in the water-bath of 60 DEG C, and decolour 90min。Solution after decolouring is concentrated into paste, vacuum drying on a rotary evaporator, obtains crude extract。With crude extract for material, adopt macroporous resin adsorption, the method of ethanol water gradient elution carries out composition separation, followed the trail of by raw survey of indoor eelworm-killing activity, the fraction that eelworm-killing activity is stronger, purification on normal-phase silica gel and ODS reverse phase silica gel post is adopted to separate purification further, through high performance liquid chromatography separation purification, obtain monomeric compound, the monomeric compound having eelworm-killing activity is carried out various spectroscopic data mensuration, the data obtained and relevant information are compared, obtain compound (1), it it is the product that replaced by multiple glycosyls further of a naringin, consult and comparison document finds this compound1HNMR and13(solvent is DMSO-d to CNMR data6) all consistent with the theaflavanoside IV separated from Camellia sinensis seed extract of report (LiNing, 2007), determine that it is (2S)-naringin-7-O-β-D-Glucose (1 → 2)-α-L-rhamnose-(1 → 2)-xylose (1 → 6)]-β-D-Glucose glycosides, i.e. theaflavanoside IV, measuring its spectroscopic data is1H-NMR(DMSO-d6, 500MHz) δ .12.05 (1H, brs, 5-OH), 9.60 (1H, 4'-OH), 7.35, 6.80 (each 2H, d, J=8.6Hz, H-3', 5' and 2', 6'), 6.12, 6.10 (each 1H, brs, H-6, 8), 5.51 (1H, dd, J=12.8Hz, 2.8Hz, H-2), 5.26 (1H, d, J=7.5Hz, H-Glc-1-1), 5.12 (1H, d, J=3.8Hz, H-Rha-1), 4.31 (1H, dd, J=7.7, 2, 6Hz, H-Glc-2-1), 4.13 (1H, dd, J=7.5, 2.8Hz, H-Xyl-1), 3.40 (1H, overlapped, H-3b), 2.72 (1H, dd, J=16.5, 2.6Hz, H-3a), 1.18 (3H, d, J=6.0Hz, H-Rha-6).13C-NMR(DMSO-d6,125MHz)δC197.2 (C-4), 164.4 (C-7), 162.9 (C-5), 162.7 (C-9), 157.7 (C-4'), 128.5 (C-1'), 128.4 (C-2', 6'), 115.1 (C-3', 5'), 104.4 (C-Glc-2-1), 103.7 (C-Xyl-1), 103.2 (C-10), 100.4 (C-Rha-1), 96.7 (C-Glc-1-1), 96.1 (C-6), 94.9 (C-8), 81.7 (C-Rha-2), 78.4 (C-2), 76.6 (C-Xyl-3), 76.4 (C-Glc-2-3, 5), 76.3 (C-Glc-2-3), 75.9 (C-Glc-1-2), 75.0 (C-Glc-1-5), 73.9 (C-Glc-2-2), 73.2 (C-Xyl-2), 70.7 (C-Rha-4), 69.5 (C-Glc-1-4), 69.3 (C-Glc-2-4), 69.2 (C-Xyl-4), 67.7 (C-Rha-5), 69.1 (C-Rha-3), 67.7 (C-Glc-1-6), 65.5 (C-Xyl-5), 60.8 (C-Glc-2-6), 41.8 (C-3), 17.8 (C-Rha-6)。ESI-MS shows that its quasi-molecular ion peak is m/z894 [M+Na]+With 873 [M–H]–。
[α]25 D–105.2(c0.25,MeOH)
Embodiment 2: Plant nematode egg hatching inhibitory activity is measured by flavone compound theaflavanosideIV
Survey egg hatching inhibitory activity is raw: with 24 hole biological culture plates (finishing line in bottom), every hole adds the medicinal liquid (after addition ovum grain, solution ultimate density is 0.83mg/mL) of the 1mg/mL of 0.5mL, add the ovum liquid that 0.1mL concentration is 1000/mL, often process and set 4 repetitions, with sterilized water for comparison, put 25 DEG C of calorstats, respectively at the 3rd, 5,7d records the second instar larvae number hatched under inverted microscope, and calculates
Meloidogyne incognita egg hatching inhibitory activity measurement result is shown, Meloidogyne incognita egg hatching is had strong inhibitory activity by flavone compound theaflavanosideIV, process 3 with 0.83mg/mL concentration, 5,7,9d, be 75% 94% to egg hatching suppression ratio, refer to table 1。
Meloidogyne incognita egg hatching inhibitory activity is measured by table 1theaflavanosideIV
Note: 1) data form is in table:Representing 4 times and repeat meansigma methods, S.E is standard error；
2) in table, data are repeat meansigma methods 4 times, represent at 5% difference not notable (DMRT) with indicating same letter after column data
Embodiment 3: Plant nematode cytotoxicity is measured by flavone compound theaflavanosideIV
Weigh 0.05g compound (1) flavone compound theaflavanosideIV, being dissolved in the sterilizing pure water of 10mL, (sample is first with the aquesterilisa hydrotropy of a small amount of about 50 DEG C, then it is being settled to 10mL), obtain the concentration that concentration is 5mg/mL, be then diluted to required gradient concentration with sterilizing pure water successively。With 24 hole biological culture plates, every hole adds the medicinal liquid of each Concentraton gradient of 0.5mL, add the second instar larvae suspension (about 100-200 bar) of 0.5mL, each process sets 4 repetitions, with sterilized water as comparison, puts 25 DEG C of calorstats, respectively at 24h, 36h, 48h, 72h, 96h (clear water recovery 24h), observe counting, under inverted microscope, record nematicide data anyway, and calculate corrected mortality:
Raw survey is it is shown that processing 36h, flavone compound theaflavanosideIV is LC to the lethal concentration of 50 of Semen Tritici aestivi cyst roundworm (Heterodera.avenarea)50=9.064 μ g/ml, process 36h, and the lethal concentration of 50 to soy bean cyst roundworm (Heteroderaglycines) is LC50=213.915 μ g/ml；Process the lethal concentration of 50 respectively LC of Meloidogyne incognita (Meloidogyneincognita) second instar larvae 24h, 48h50=81.21 μ g/ml and LC50=50.77 μ g/ml, illustrate that Semen Tritici aestivi cyst roundworm and root-knot nematode are all had strong cytotoxicity, especially that the virulence of root-knot nematode is very strong, refer to table 2。
The table 2 flavone compound theaflavanosideIV cytotoxicity to cyst roundworm and root-knot nematode
Pratylenchidae (Pratylenchusscribneri) (mixing worm age) and aphelenchoides besseyi (Aphelenchoidesbessryi) (mix worm age) 96h is processed with 0.83mg/ml concentration, the corrected mortality of clear water recovery 24h respectively reaches 83% and 86%, refers to table 3。
The table 3 flavone compound theaflavanosideIV cytotoxicity to Pratylenchidae and aphelenchoides besseyi
Note: 1) data form is in table:Representing 4 times and repeat meansigma methods, S.E is standard error；
2) in table, data are repeat meansigma methods 4 times, represent at 5% difference not notable (DMRT) with indicating same letter after column data。
Claims (5)
1. flavone compound theaflavanosideIV as nematicide effective ingredient preventing and treating plant nematode diseases in application, shown in the structure of flavone compound theaflavanosideIV such as formula (1)
。
2. application according to claim 1, described Plant nematode is cyst roundworm, root-knot nematode, Pratylenchidae, aphelenchoides besseyi。
3. application according to claim 2, described cyst roundworm is Semen Tritici aestivi cyst roundworm (Heterodera.avenarea) or soy bean cyst roundworm (Heteroderaglycines)。
4. application according to claim 1, described application is flavone compound theaflavanosideIV to make pesticide impose on morbidity plant surface or root。
5. application according to claim 1, described preventing and treating plant nematode diseases is for suppressing line eggs hatching or killing Plant nematode and effectively reduce nematode infection。
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