CN104987329A - Dihydroagarofuran type sesquiterpene compound and preparing method and application thereof - Google Patents
Dihydroagarofuran type sesquiterpene compound and preparing method and application thereof Download PDFInfo
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- CN104987329A CN104987329A CN201510321499.0A CN201510321499A CN104987329A CN 104987329 A CN104987329 A CN 104987329A CN 201510321499 A CN201510321499 A CN 201510321499A CN 104987329 A CN104987329 A CN 104987329A
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- dihydroagarofuran
- monimopetalum
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Abstract
The invention discloses a dihydroagarofuran type sesquiterpene compound, the preparing method of the compound, and the application of the compound in preparing anti-microbial pesticides and relates to the field of medicinal chemistry. According to the application of the novel sesquiterpene compound in anti-microbial pesticides, the structure of the adopted sesquiterpene compound is shown in the figure of the abstract and is named 1beta-acetyl-6alpha-(5-carboxyl-N-methyl-2-pyridone)-8beta-nicotinoyl-9alpha-benzoyl-beta-dihydroagarofuran. The compound is characterized in that the stem leaves of the plant Monimopetalum Chinese Rehd. are used as raw materials, and then the compound is obtained through extraction and separation with the natural product chemistry method. As a pesticide, the compound has a remarkable resisting effect on pests including plutella xylostella, cabbage caterpillar, corn armyworm, prodenia litura, argyrogramma agnate, pea aphids, rice-stem borer, rice tryporyza incertulas and henosepilachna vigintioctomaculata. As a sterilant, the compound has a remarkable resisting effect on sclerotinia sclerotioru, rhizoctonia cereal, fusarium graminearum and botrytis cinerea person.
Description
Technical field
The present invention relates to medicinal chemistry art, disclose a kind of new sesquiterpenoids and preparation method thereof and the purposes in the antibacterial insecticide pesticide of preparation.
Background technology
China is large agricultural country, and about 400,000,000 hectares of the long-term occurring area of crop diseases and pest crop smothering, need produce and use 800,000 tons, agricultural chemicals every year, and agricultural chemicals has become indispensable factor in agriculture production.Widely using of agricultural chemicals, although serve vital role to production development, also occurred such as insect pest, disease resistance problems (resistance), to the pollution of environment and residual and accumulation problem (residue) in agricultural and animal products, injure natural enemy, destroy balance of nature, cause pest resurgence problem (resurgence) etc. progressively to eliminate and forbidding riskiest pesticide bases oneself upon me
state of statefeelings, ensure agricultural product quality and safety, ecological environment security, the control measures that the public is healthy and life security is effective
[1].On June 15th, 2011, through State Council approved, the Ministry of Agriculture, Ministry of Industry and Information, Chinese Ministry of Environmental Protection, the State Administration for Industry and Commerce, State Administration of Quality Supervision, Inspection and Quarantine combine No. 1586th, issue bulletin and have prohibited 23 kinds of riskiest pesticides, and this provides new development opportunity and huge market potential for plant pesticide.Plant pesticide extensively exists in natural ecological environment, aboundresources, and most low toxicity, does not destroy ecotope, and residual few, selectivity is strong, no
kill and woundpest natural enemy, insect and germ are difficult to develop immunity to drugs to plant pesticide, and serviceable bife is long, and consumption is few, and use cost is low.Using plant pesticide, for promoting sustainable development, there is extremely important realistic meaning
[2].
Monimopetalum chinense (
monimopetalum Chineserehd.) be that Celastraceae (Celastraceae) monimopetalum chinense belongs to monotypic genus plant, be Chinese endemic plant, be only distributed in Anhui and Jiangxi, very rare to monimopetalum chinense investigation and application.Report that separation obtains 4 pentacyclic triterpenoids from monimopetalum chinense, is respectively suberone (friedelin), epifriedelinol (epifriedelinol), glochidone (glochidone) and epifriedelinol octacosane acid esters (epifriedelinol octacosanate)
[3-5].Jiangxi monimopetalum chinense among the people treats rheumatic arthritis.In monimopetalum chinense, other chemical compositions and extract are not also reported for application such as desinsections.
Many Celastraceae plants in Chinese traditional agriculture in order to protect farm crop from insect infestations.Record according to " Xinhua book on Chinese herbal medicine outline ", this section has 11 kind of plant to have insecticidal activity, for trypterygine, Tripterygium hypoglaucum, black climing, winged euonymus, Stem or Leaf of Fortune Euonymus, square roundleaf winged euonymus,
xinjiangwinged euonymus, Yunnan are shut out in vain, Euonymus verrucosides, celastrus angulatus, Stem of Oriental Bittersweet
[6].Its bioactive compounds think containing dihydroagarofuran be the polynary ester of skeleton and alkaloid thereof and diterpene-kind compound as Triptonide (triptonide) and triptolide (triptolide), to the various pests of leaf vegetables, melon and fruit class have avoid keep away, food refusal,
poisoningand Developing restraint is grown and repellent rate effect, but its action of contace poison is more weak, mainly stomach poison function
[7].
But sesquiterpenoid is not all containing 5-carboxy-N-methyl-2-pyridone (CNMP) group in above-mentioned plant.Dihydroagarofuran type sesquiterpene to the anesthesia of insect and
poisoningact on relevant with kind with its substituent position, different substituting groups can cause significant activity difference
[8].The dihydroagarofuran type sesquiterpene connecting CNMP group only finds in 5 kind of plant, be respectively micro-scarce Caulis Mayteni (
maytenus emarginata) in micro-scarce maytenin Emarginatine A-H, China
taiwancaulis Mayteni (
maytenus emarginata(Willd.) D. Hou) in Emarginatinine, shark's fin rattan (
loeseneriella merrilliana) in Hippocrateine I-III, tall and big shark's fin rattan (
hippocratea excelsa) in compound 1-5,7-19, plant (
reissantia buchananii) in Reissantins A-C, F-H, but all not studies have reported that its insecticidal and antibacterial is active
[9].
The prior art relevant with the present invention has.
[1] Hou Taiping.Research Progresses on Botanical Pesticides.Chinese agriculture science and technology Leader, 2006,8(6): 12-16.
[2] Zhao Shuying, Song Zhanqian, Wang Qiufen.China's plant pesticide resource development situation and trend.Jiangsu's agriculture science, 2005, (1): 4-6.
[3] Chen Ling, Xie Ping, Qi Wei etc.The research of monimopetalum chinense chemical composition.Jiangxi College of Traditional Chinese Medicine journal, 1994,6(1): 30-32.
[4] thank flat, Zhu Shenghua, Feng Yulin etc.The research (I) of monimopetalum chinense chemical composition.Jiangxi College of Traditional Chinese Medicine journal, 2001,13(4): 159-160.
[5] thank flat, Zhu Shenghua, Feng Yulin etc.The research (II) of monimopetalum chinense chemical composition.Jiangxi College of Traditional Chinese Medicine journal, 2002,14(1): 39-40.
[6] Huang Junhai,
liu Guoqiang, Bai Hongjin, Hu Zhaonong, Wu Wenjun.13 kinds of Celastraceae plant insecticide activity researchs.Northwest Botany Gazette, 2004,24(4): 688-692.
[7] Hu Zhaonong,
liu Guoqiang, Wu Wenjun.China's Celastraceae pesticide plant progress.Insect knowledge, 2005,42(6): 629-634.
[8] Zhu Jingbo, Mu Yanfeng.The New research progress of dihydroagarofuran compounds structure activity relationship.Agriculture of Anhui science, 2008,36(30): 13008-13010.
[9] Luciano M. Liao. Sesquiterpene Pyridine Alkaloids. ChemInform, 2004, 35(28)。
Summary of the invention
The present invention aims to provide a kind of new sesquiterpenoids and preparation method thereof and the purposes in the antibacterial insecticide pesticide of preparation.
The invention discloses a kind of dihydroagarofuran type sesquiterpenoid, chemistry is by name: 1
β-ethanoyl-6
α-(5-carboxy-N-methyl-2-pyridone)-8
β-nicotinoyl-9
α-benzoyl-
β-dihydroagarofuran, structure, for shown in formula I, is characterized in that: have 15 carbon atoms in mother nucleus structure, forms 3 rings, 26 rings (entirely saturated naphthalene nucleus), 15 yuan of furan nucleus.Parent nucleus there are 4 methyl; C-1, C-6, C-8, C-9 have 4 substituting groups to exist, and substituting group comprises 5-carboxy-N-methyl-2-pyridone (CNMP).Molecular weight is 672, and molecular formula is C
37h
40n
2o
10.
The preparation method of above-mentioned compound, is characterized in that: with plant monimopetalum chinense (
monimopetalum Chineserehd.) cauline leaf is raw material, and methyl alcohol, ethanol or aqueous alcohols are extracted, and filter, concentrate to obtain medicinal extract, extraction into ethyl acetate after medicinal extract aqueous suspension, can obtain ethyl acetate extract.Ethyl acetate extract is through column chromatography repeatedly, and column chromatography filler is macroporous resin or polymeric amide or gac or reverse phase silica gel, collects 50 ~ 80% alcohol wash-out positions and get final product.
The present invention has also done multinomial experiment to the antibacterial insecticidal activity of above-claimed cpd, wherein all there is remarkable killing effect to phytopathogens such as the insects such as small cabbage moth, cabbage caterpillar, maize army worm, prodenia litura, three-spotted phytometra, pea aphid, rice-stem borer, Yellow Rice Borer, potato ladybug and rape sclerotium, Rhizoctonia cereali, gibberella saubinetii, strawberry ash bacterium, can use as the activeconstituents of agricultural chemicals.
Accompanying drawing explanation
fig. 1, the embodiment of the present invention 1 gained compound H PLC-MS positive ion color atlas.
fig. 2, the embodiment of the present invention 1 gained compound high resolution second order ms (HR-ESI MS) spectrogram.
fig. 3, the embodiment of the present invention 1 gained compound proton nmr spectra (
1h-NMR) spectrogram.
fig. 4, the embodiment of the present invention 1 gained compound carbon-13 nmr spectra (
13c-NMR) spectrogram.
Embodiment
In conjunction with embodiment, the present invention is described in further detail, but content of the present invention is not restricted to cited embodiment.
Embodiment 1.
Monimopetalum chinense sesquiterpene cauline leaf 5 kg, by 90% ethanol, 60 DEG C of refluxing extraction 3 times, filter, concentratedly to obtain medicinal extract, extraction into ethyl acetate after medicinal extract aqueous suspension, can obtain ethyl acetate extract.Ethyl acetate extract, through D101 macroporous resin chromatography, is collected 50 ~ 80% alcohol wash-out positions, then is used C
18reverse phase silica gel post, collects 70% wash-out position, then uses C
18reverse phase silica gel Column preparation liquid phase, collects 75% wash-out position, obtains compound 1
β-ethanoyl-6
α-(5-carboxy-N-methyl-2-pyridone)-8
β-nicotinoyl-9
α-benzoyl-
β-dihydroagarofuran, purity detects through HPLC-MS and is greater than 98%.
Compound second order ms data syncaryon magnetic resonance spectrum can resolve its structure.HR-ESI MS m/z673.2699 [M+H]
+, display molecular formula is C
37h
40n
2o
10, degree of unsaturation is 19.Second order ms figure shows on parent nucleus 4 substituted acyls, 613.2492 [M+H-HOAc]
+, 491.2163 [M+H-HOAc-HOBz]
+, 337.1773 [M+H-HOAc-HOBz-CNMP]
+, 215.1409 [M+H-HOAc-HOBz-CNMP-HONic]
+, 136.0382 [CNMP-OH]
+.Substituent position by nuclear magnetic resonance spectrum determine (
table 1), be retrieved as a new compound through Scifinder.
Embodiment 2.
The preliminary toxicity test of sterilant adopts spray method.
(1), medicament preparation: by monimopetalum chinense ethyl acetate extract, new sesquiterpene is mixed with the acetone soln of 1mg/mL, then uses acetone diluted 10 times, for subsequent use.
(2), try worm pipette: get small cabbage moth (
plutella xyllostella) 3 instar larvaes concentrate mixing after, enter culture dish with writing brush type brush, often process 10, repeat once.Often process need try worm 15-30 head, and each test all will establish blank.Temperature is generally at 20-28 DEG C, and relative humidity 60-80%, ventilation is good.
(3), spraying quality arbitration: check the size of spraying droplet and spraying whether uniformity with the white garden scraps of paper of 9cm, as undesirable, nozzle adjustable and position, make spraying quality reach basic demand.
(4), treatment process: select potter spray tower, before spraying liquid, by clear water and a large amount of spraying of liquid for spraying.Need before changing dressings fully to clean by bottom batch pan and spray chamber with cloth, the liquid of then a large amount of spraying test.Add certain fresh vegetable leaf in the culture dish being connected to small cabbage moth after, carry out spraying with pipette, extract 3ml liquid, after about 10 seconds, treat the whole sedimentation of liquid, take out culture dish, carry out mark, blank only sprays clear water.After medicament is dry, examination worm is placed in recovery indoor cultivation check result after 24 hours together with feed.After 24 hours and 48 hours, check borer population anyway, calculate mortality ratio and corrected mortality, and compare the virulence size of different agents.Examination worm anyway standard, generally using can normal activity or circle in the air or can normally take action as the worm that lives, what all the other were poisoning is dead worm.
(5), experimental result.
By
table 2known, monimopetalum chinense ethyl acetate extract and new sesquiterpene all have remarkable insecticidal action, and under 0.1mg/mL concentration, the insecticidal action of new sesquiterpene is better than ethyl acetate extract, illustrate that new sesquiterpene is active insecticidal components.
Embodiment 3.
Sterilant contact toxicity measures and adopts topical application.
(1), medicament preparation: according to preliminary virulence test result, the acetone mother liquor acetone diluted of new sesquiterpene 1mg/mL is become 5 concentration, every concentration 5mL, load tool plug small test tube.And be contrast with acetone.
(2), indoor for examination insect: small cabbage moth (
plutella xyllostella), cabbage caterpillar (
pieris rapael.), maize army worm (
mythimna separata Walker), prodenia litura (
prodenia lituraf.), three-spotted phytometra (
plusia agnata Staudinger), pea aphid (
pea aphids), rice-stem borer (
chilo suppressaliswalker), Yellow Rice Borer (
tryporyza incertulaswalker), potato ladybug (
henosepilachna vigintioctopunctata), 3 instar larvaes that during test, picking individual size is basically identical are for examination.
(3), drop treatment process: selecting neat 3 instar larvaes, to choose diameter be in the culture dish of 9 cm, every ware 10 worm.Carry out drop process by trying worm in culture dish by head, lepidopterous larvae drop is on polypide pronotum, and every drop medicament 1 μ L, first contrasts, then from lower concentration to high density, every concentration 20, in triplicate.After being disposed, the examination worm processed being placed in the environment of 27 DEG C, fresh feed of feeding, 24 hours, after 48 hours, checking dead borer population, touch its polypide without any reactor for death with thing.
(4), experimental result.
By
table 3known, the monimopetalum chinense new sesquiterpenoid sterilant produced by the technology of the present invention all has good drug effect to several examination worms for examination.
Embodiment 4.
Bactericide bacteriostasis circle assay method.
(1), medicament preparation: the acetone mother liquor sterilized water of new sesquiterpene 1mg/mL is diluted to 30,20,10ppm, be settled to 10mL.Take sterilized water as contrast.
(2), prepare bacteria suspension: test plant pathogenic bacteria have rape sclerotium (
sclerotinia Sclerotiorum), Rhizoctonia cereali (
rhizoctonia cerealis), gibberella saubinetii (
fusarium graminearum), strawberry ash bacterium (
botrytis cinerea), Phytophthora capsici (
phytophthora capsici), anthrax bacteria (
colletotrichum gloeosporioides).Get cultivation about 7 days for examination test tube strains, add 8mL sterilized water, gently scrape spore on slant medium and mycelium with transfering loop, prepare spore suspension, by spore suspension by sterilized double layer filtered through gauze in sterilizing triangular flask, and with sterilizing tampon plug mouth.Then draw a small amount of spore suspension on slide glass with sterilizing suction pipe, at low power (15 × 10) test under microscope each visual field miospore number, require at about 80.
(3), bacterium culture medium plane is carried in preparation: when the substratum (sterilizing) of fusing being cooled to 45-50 DEG C, aseptically, inhale substratum 9mL, add 1mL bacterium liquid in the culture dish of sterilizing, fully mix, make and carry bacterium culture medium plane.
(4), chemicals treatment: the medicament prepared is poured in the little culture dish of sterilizing, with disinfecting forceps, sterilized filter paper is put into the liquid immersion to take out after 1 minute, be placed on sterilized filter paper, medicament unnecessary on filter paper is sucked, aseptically, put in year bacterium culture medium plane.Need 4 to carry bacterium culture dish altogether, 2 is one group, is divided into two groups.Put 6 filter papers at every culture dish, and perform mark.The culture dish of process, 4-6 hour in the refrigerator being first placed on 2-4 DEG C, until medicament in the medium fully after diffusion, then puts into 28 DEG C of cultivations.Check result after 30-40 hour, measures antibacterial circle diameter (in units of millimeter) with chi right-angled intersection, averages.
(5), experimental result.
By
table 4known, the new sesquiterpenoid sterilant of monimopetalum chinense produced by the technology of the present invention is effective to rape sclerotium, Rhizoctonia cereali, gibberella saubinetii, strawberry ash bacterium, but to Phytophthora capsici and anthrax bacteria invalid.
Claims (6)
1. a dihydroagarofuran type sesquiterpene, is characterized in that chemistry is by name: 1
β-ethanoyl-6
α-(5-carboxy-N-methyl-2-pyridone)-8
β-nicotinoyl-9
α-benzoyl-
β-dihydroagarofuran, structure is such as formula shown in I:
formula I.
2. the preparation method of compound according to claim 1, is characterized in that: with plant monimopetalum chinense (
monimopetalum Chineserehd.) cauline leaf is raw material, methyl alcohol, ethanol or aqueous alcohols are extracted, filter, concentrate to obtain medicinal extract, extraction into ethyl acetate after medicinal extract aqueous suspension, ethyl acetate extract can be obtained, ethyl acetate extract is through column chromatography repeatedly, and column chromatography filler is macroporous resin or polymeric amide or gac or reverse phase silica gel, collects 50 ~ 80% alcohol wash-out positions and get final product.
3. a natural botanical insecticide, is characterized in that using the compound of claim 1 as insect disinfestation component.
4. natural botanical insecticide according to claim 3, is characterized in that described natural botanical insecticide is for killing the insects such as small cabbage moth, cabbage caterpillar, maize army worm, prodenia litura, three-spotted phytometra, pea aphid, rice-stem borer, Yellow Rice Borer, potato ladybug.
5. a natural phant antiseptic-germicide, is characterized in that using the compound of claim 1 as antibacterial components.
6. natural phant antiseptic-germicide according to claim 5, is characterized in that the Plant diseases that described natural phant antiseptic-germicide causes for preventing and treating rape sclerotium, Rhizoctonia cereali, gibberella saubinetii, strawberry ash bacterium etc.
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Cited By (4)
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| CN105497098A (en) * | 2015-12-21 | 2016-04-20 | 江苏省中国科学院植物研究所 | Monimopetalum Chinese extract with anti-inflammatory activity, preparing method and application of extract |
| CN106397254A (en) * | 2016-08-29 | 2017-02-15 | 南京农业大学 | Chiral 8-hydroxyhomodrimane sesquiterpene amide compound and application of same as agricultural bactericide |
| CN110028498A (en) * | 2019-05-18 | 2019-07-19 | 江苏省中国科学院植物研究所 | A kind of new sesquiterpenoid and its preparation method and application in monimopetalum chinense |
| CN111978309A (en) * | 2020-08-25 | 2020-11-24 | 上海诗丹德标准技术服务有限公司 | Tripterygium wilfordii source compound, application and preparation method thereof, pharmaceutical composition and pesticide |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105497098A (en) * | 2015-12-21 | 2016-04-20 | 江苏省中国科学院植物研究所 | Monimopetalum Chinese extract with anti-inflammatory activity, preparing method and application of extract |
| CN105497098B (en) * | 2015-12-21 | 2019-08-02 | 江苏省中国科学院植物研究所 | Monimopetalum chinense extract with anti-inflammatory activity, preparation method and applications |
| CN106397254A (en) * | 2016-08-29 | 2017-02-15 | 南京农业大学 | Chiral 8-hydroxyhomodrimane sesquiterpene amide compound and application of same as agricultural bactericide |
| CN106397254B (en) * | 2016-08-29 | 2017-12-29 | 南京农业大学 | Chiral 8 hydroxyl homodrimane sequiterpene amides compounds and the purposes as disinfectant use in agriculture |
| CN110028498A (en) * | 2019-05-18 | 2019-07-19 | 江苏省中国科学院植物研究所 | A kind of new sesquiterpenoid and its preparation method and application in monimopetalum chinense |
| CN110028498B (en) * | 2019-05-18 | 2022-03-25 | 江苏省中国科学院植物研究所 | New sesquiterpene compound in hedyotis petiolata as well as preparation method and application thereof |
| CN111978309A (en) * | 2020-08-25 | 2020-11-24 | 上海诗丹德标准技术服务有限公司 | Tripterygium wilfordii source compound, application and preparation method thereof, pharmaceutical composition and pesticide |
| CN111978309B (en) * | 2020-08-25 | 2022-03-25 | 上海诗丹德标准技术服务有限公司 | Tripterygium wilfordii source compound, application and preparation method thereof, pharmaceutical composition and pesticide |
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