CN102771496B - Plant growth regulator composition containing polyprenols and preparation method thereof - Google Patents
Plant growth regulator composition containing polyprenols and preparation method thereof Download PDFInfo
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- CN102771496B CN102771496B CN201210265860.9A CN201210265860A CN102771496B CN 102771496 B CN102771496 B CN 102771496B CN 201210265860 A CN201210265860 A CN 201210265860A CN 102771496 B CN102771496 B CN 102771496B
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
- Cultivation Of Plants (AREA)
Abstract
The invention relates to a plant growth regulator composition containing polyprenols and a preparation method thereof and belongs to the field of development and application of plant growth regulatory substance. The preparation method comprises the step of using polyprenols with 0.1-100mg/L of effective concentration to perform soaking, sprinkling and other treatment on irrigation and plants, plant tissues and seeds for1-3 times every day, wherein the treatment lasts for 1-40 days, and seed germination, seedling growth and striking of the plant tissue roots can be promoted. Due to the fact that the polyprenols is chemical substance from natural plants and is free of toxicity to relevant metabolic mechanisms in human body and the plants and free of harm to the environment, the fact that polyprenols is used for developing natural green plant growth regulators has important significance and has good business prospect.
Description
Technical field
The present invention relates to a kind of content has plant growth regulator composition of polypentenol and preparation method thereof, belongs to the development and application field of plant growth regulating substance, is exclusively used in the fields such as agricultural chemicals exploitation, farmland chemical regulation and provenance agricultural.
Technical background
Polypentenol (polyprenols) is extensively present in the plants such as green confierophyte and ginkgo, be to take C5 isopentene group as the single lipids of structure, structure, can divide: the n-OH of 3-(cis) n-OH of 2-(cis) n-OH of betulinol type ω-(trans), luxuriant and rich with fragrance card alcohol type ω-(trans) and alltrans Salanesol type ω-(trans).
Polypentenol and ester class thereof are nonpolar ester type compounds, its leaching process is: the separation of extraction-hydrolysis-extraction-column chromatography or molecular clock etc., main organic solvent has: chloroform, n-hexane, benzinum, toluene, benzene, pentane etc., can also use mixed solvent, as: n-hexane-ether, acetone-chloroform, methanol-acetone, n-hexane-acetone.The employing benzinums such as Yang little Ming carry out lixiviate to ginkgo leaf, obtain liposoluble substance, further after hydrolysis, adopt n-hexane to extract, by saturated sodium-chloride water solution washing organic facies, obtain polypentenol and oil-soluble impurities, with thin layer chromatography, carry out separation, and then adopt column chromatography purification.Li Chunbin etc. dissolve ginkgo leaf ligroin extraction with acetone, carry out purification by silica gel column chromatography after filtration, with benzinum and benzinum: ether (25: 1) linear gradient elution, the polyprenyl acetates purity obtaining reaches more than 90%.The employing benzinums such as Sun Lei extract with the solid-liquid ratio of 1: 7, and 10 hours, the extract obtained column chromatography for separation of carrying out, obtained polypentenol.The employing benzinums such as Wang Chengzhang carry out lixiviate to ginkgo leaf, with EtOH-NaOH solution, it is refluxed, then with saponification agent by preparing unsaponifiable matter at 1: 5.Deng Yongzhi etc. carry out carbon dioxide supercritical extraction to ginkgo leaf, and then adopt benzinum and ether to dissolve in the ratio of 19: 1, with silica gel column chromatography, carry out separation afterwards, with the centrifugal removal of impurities of acetone solution eluate with obtain the polypentenol of purifying.
The process of growing of plant is subject to the regulation and control of plant endogenous hormones conventionally, is also subject to the restriction of various unsuitable environmental conditions simultaneously, often causes the decline of growth rate and output, and the metabolic function downward at each tissue of plant and position is one of main inducing wherein.Plant growth regulator is the chemicals of natural source, for example, also referred to as plant hormone (growth hormone, gibberellin, cytokinins, ethene, brassinosteroid or abscisic acid), fat oligosaccharides, peptide, derivative of fatty acid and oligosaccharins, or they can be the synthetic compounds (the derivative biology of natural generation auxin, ethrel) making.Plant growth regulator is the trace level chemical substance that coordinate plant growth is grown, and growth and development of plants needs the supply of liquid manure nutrition, is also subject to adjusting and the control of plant growth substance simultaneously.At low dense lower energy, produce the physiological effect of obviously showing, make plant that strong Physiology and biochemistry occur and react with form.Plant, at rooting of cuttings, promotes bolting to bloom, solid, prevent from coming off, and vegetables fruit thinning, induction and breaking dormancy, promote ripe and strengthen the aspects such as resistance, applied widely.From eighties of last century nineties, the research and development of natural source plant growth regulator become one of focus of domestic research.Utilize natural plants as the raw material that extracts plant growth regulator, realize agriculture sustainable development significant.
At present, both at home and abroad the research of natural polypentenol is mainly concentrated on to anti-hepatitis, the biologically active such as antitumor.Research shows that polyprenols is natural products, nontoxic to human body, without mutagenesis, without teratogenesis with without carcinogenesis, at aspects such as hepatitis virus resisting and AIDS virus and NACT leukemia, there is obvious biologically active, to immunologic function diseases such as hypertension, high fat of blood, diabetes, gout, lupus erythematosus, chronic hepatitis, suppressing tumour and auxiliaryization, radiotherapy all has obvious effect.Polypentenol has good inhibition to mouse transplantability hepatoma Heps, sarcoma s180 and Emhorn knurl EC.But polypentenol should be made in to plant growth regulating almost not to be had.Korea S power is held dragon and from cotton plant leaf, is extracted separation and obtain undecaprenol and ten diterpene alcohol, study it and be applied to plant seed as plant growth regulator, result shows, its concentration has good stratification effect [Chinese patent CN1529550A] to seeds such as corn, cucumber when 100ppm and 50ppm.And polypentenol in this patent is the birch terpene alcohols polypentenol by 14～24 (take 17～19 as main) individual isopentene group cell formation, in its chemical constitution and cotton plant leaf, extract obtain different.Polypentenol is the compound in natural plants source, has safety, easily biological-degradable, the feature such as environmentally friendly, therefore utilizes polypentenol exploitation natural green plant growth regulator to have important practical significance.
Summary of the invention
For achieving the above object, having invented a kind of content has plant growth regulator composition of polypentenol and preparation method thereof, it is characterized in that being comprised of following steps:
(1) preparation of polypentenol: by the extraction of plant leaf powder process, saponification, washing, after being dried;
(2) preparation of urea alcoholic solution: urea is put into absolute methanol, bathe and to be heated to urea and all to dissolve filling nitrogen Water Under, wherein the w/v of urea and absolute methanol is 1: 10～5: 10, and heating reflux temperature is 60～75 ℃;
(3) carry out urea clathrate reaction: in urea alcoholic solution, add polypentenol crude extract and filler, polypentenol crude extract: filler: the ratio 0.5～1: 1～2: 10～40 of urea alcoholic solution, stirring and refluxing at 60-75 ℃ of temperature, be cooled to after room temperature, at-20～10 ℃ of deepfreezes to urea inclusion crystallization, then suction filtration, collects respectively crystal and filtrate.
(4) crystal step (3) being obtained fills post, at the uniform velocity injects chromatographic column carry out wash-out with mobile phase, collects elution fraction, merge, the polypentenol after being refined after concentrating, analyzes through HPLC, the purity of sample is more than 50%, and the rate of recovery is more than 80%.
(5) polypentenol step (4) being obtained, by percentage, be: polypentenol 1%～20%, cosolvent 1～50%, emulsifier 1～20%, stabilizing agent 1～10%, water surplus, at room temperature ultrasonic filter emulsification 10～30min, preserves at low temperature below 4 ℃, before using, by deionized water, is diluted to desired concn, stir, make the plant growth regulator composition that content has polypentenol.
2, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, it is characterized in that plant leaf in step (1) is a kind of in ginkgo leaf, pine needle, mulberry leaf, the structure of its polypentenol is betulinol type ω-(trans)
2-(cis)
n-OH, wherein the scope of n is 10～20.
3, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, it is characterized in that the filler in step (3) is one or more in silica gel, active carbon, polyamide, attapulgite, aluminium oxide, diatomite.
4, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, it is characterized in that mobile phase in step (4) is a kind of in benzinum, n-hexane, ether.
5, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, it is characterized in that the cosolvent in step (5) selects one or more in methyl alcohol, ethanol, acetone, emulsifier selects one or more in Tween 80, OP-10, OP-21, X-100, and stabilizing agent is selected from one or more in n-butanol, propyl alcohol, glycerine.
6, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, and it is characterized in that being mixed with polypentenol after solution is 0.1～100mg/L as effective final concentration of plant growth regulator.
7, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, it is characterized in that, plant growth regulator to plant, plant tissue or seed irrigate, spray wine, immersion or
process, or directly add the medium that comprises above-mentioned vegetable material, process continuously every day 1～3 time 1～40 day.
8, a kind of content has plant growth regulator composition of polypentenol and preparation method thereof according to claim 1, it is characterized in that, described plant or seed are a kind of in wheat, ternip, Yellow Emperor, a legendary ruler chrysanthemum, cucumber, fairy bamboo and rosemary, Xue MingRosma rinus officinalis.
A kind of content provided by the present invention has plant growth regulator composition of polypentenol and preparation method thereof, also has the following advantages:
1) pollution-free, environmental protection polypentenol derives from ginkgo leaf, pine needle, mulberry leaves etc., easily biological-degradable, dolichol structure contained in it and human body and mammal internal organs approaches, and can in human body, be metabolized to dolichol phosphate ester, as the biosynthetic carrier of glycoprotein.Therefore under the various practice conditions such as farmland and greenhouse, use low concentration polypentenol can not cause adverse effect to ecotope.
2) applied range this method is exclusively used in nuisanceless production, the field such as group training etc. that comprises agricultural chemicals exploitation, farmland chemical regulation, provenance agricultural, can regulating plant seed germination, take root, the growth of crop and controlling through saving the effects such as growth.
Embodiment
Following examples are more of the present invention giving an example, and should not be seen as limitation of the invention.
Embodiment 1: urea adduct method is prepared the method for polypentenol
Select four kinds of different types of absorption carriers such as silica gel, active carbon, polyamide, attapulgite, studied respectively the purifying research of 5 kinds of different quality proportionings such as urea and absorption carrier 10: 1 in mass ratio, 5: 1,5: 2,5: 3,1: 1.
The purification result of the different proportionings of table 1 urea silica gel
Take silica gel as shown in Table 1 as carrier, benzinum is that eluant, eluent can find out that by the experimental result of the mass ratio of different urea and silica gel polypentenol yield under pure urea condition reaches 92.08%, but its purity is only 39.83%, it is the highest that urea and silica gel mass ratio are that prepare at 5: 1 fixing loads the Polyprenols From Ginkgo Biloba L purity that purifying obtains mutually, its purity is 72.34%, along with its purity of increase of silica gel consumption diminishes again gradually, yield also declines thereupon gradually.Consider the factor of its purity and yield, the best purification condition that the silica gel of take is carrier as urea silica gel mass ratio be 5: 1, its purity is 72.34%, compared with the purity of molecular clock product C 37.9%, is greatly improved.It is irregular that pure urea loads urea crystal in crystallization process, and the inhomogeneous purification effect of dress post is poor; Along with the consumption of silica gel increases urea in Silica Surface load, product purity improves gradually, is issued to the maximum of purity 5: 1 conditions; Along with the purity of the decline polypentenol of urea ratio reduces gradually; Increase with the consumption of silica gel strengthens and causes yield to decline gradually the suction-operated of polypentenol.
The purification result of table 2 different carriers
As shown in Table 2, silica gel, active carbon, attapulgite and four kinds of different absorption carriers of polyamide have been selected, mass ratio between urea and carrier 5: 1, by contrast experiment find take silica gel as the product purity that carrier obtains higher, active carbon takes second place, and polyamide and attapulgite are that the product purity that carrier obtains improves little.The more aobvious brownish red of the product colour that polyamide, attapulgite purifying obtain, silica gel takes second place, and product colour that activated carbon purification obtains is thin out is buff.Consider and take silica gel as carrier the best.
Embodiment 2: the preparation of Polyprenols From Ginkgo Biloba L emulsion
With embodiment 1, extract the separated Polyprenols From Ginkgo Biloba L obtaining, by Polyprenols From Ginkgo Biloba L 5g, tween 2.5g, ethanol 2.5mL and water 15mL, in ultrasonic disruption instrument, carry out ultrasonic homogeneous, obtain polypentenol emulsion, and take it as mother liquor, be mixed with 5 concentration (10mg/L, 20mg/L, 50mg/L and 100mg/L).
Embodiment 3: the impact that crop seeds is sprouted
3-1: the impact on wheat seeds sprouting and growth of seedling
Selected in the same size, the wheat seed of full seed, in ultra-clean aseptic working platform, the NaClO solution with 5% soaks 20min, with distilled water flushing for several times.Under aseptic condition, take out, proceed in polypentenol sample, with distilled water, make blank, using 20mg/L IAA (heteroauxin) as positive control, each is treated to 100 seeds, establishes 3 repetitions; Seed soaks after 4h, uses distilled water flushing the surface of the seed, and seed is fitly arranged in and is placed in the auxiliary glass training shape ware that has 2 layers of gauze, puts into illumination box, under 25 ℃ of conditions, cultivates 7 days.Duration of germination is observed every day, keeps the skin wet, and a record germination grain number, height of seedling and the root of its seedling are long, survey its amylase activity and improving activity of root system.The results are shown in table 3-8.
The comparison of table 3 Polyprenols From Ginkgo Biloba L to wheat seed germinating rate
The comparison of table 4 Polyprenols From Ginkgo Biloba L to wheat seed height of seedling
The comparison that table 5 Polyprenols From Ginkgo Biloba L is long to wheat seed root
The comparison of table 6 Polyprenols From Ginkgo Biloba L to wheat seed amylase activity
The comparison of table 7 ginkgo polypentenol to wheat seed improving activity of root system
3-2: the impact on Yellow Emperor, a legendary ruler chrysanthemum seed germination
Selected in the same size, the wheat seed of full seed, in ultra-clean aseptic working platform, the NaClO solution with 5% soaks 20min, with distilled water flushing for several times.Under aseptic condition, take out, proceed in polypentenol sample, with distilled water, make blank, using 20mg/L IAA (heteroauxin) as positive control, each is treated to 100 seeds, establishes 3 repetitions; Seed soaks after 4h, uses distilled water flushing the surface of the seed, and seed is fitly arranged in and is placed in the auxiliary glass training shape ware that has 2 layers of gauze, puts into illumination box, under 25 ℃ of conditions, cultivates 10 days.Duration of germination is observed every day, keeps the skin wet, and a record germination grain number.The results are shown in Table 8.
The comparison of table 8 Polyprenols From Ginkgo Biloba L to Yellow Emperor, a legendary ruler chrysanthemum percentage of seedgermination
3-3: the impact that dialogue radish seed is sprouted
Selected in the same size, the wheat seed of full seed, in ultra-clean aseptic working platform, the NaClO solution with 5% soaks 20min, with distilled water flushing for several times.Under aseptic condition, take out, proceed in polypentenol sample, with distilled water, make blank, using 20mg/L IAA (heteroauxin) as positive control, each is treated to 100 seeds, establishes 3 repetitions; Seed soaks after 4h, uses distilled water flushing the surface of the seed, and seed is fitly arranged in and is placed in the auxiliary glass training shape ware that has 2 layers of gauze, puts into illumination box, under 25 ℃ of conditions, cultivates 5 days.Duration of germination is observed every day, keeps the skin wet, and a record germination grain number.The results are shown in Table 9.
The comparison of table 9 Polyprenols From Ginkgo Biloba L dialogue radish seed germination rate
3-4: the impact on germination of cucumber seeds
Selected in the same size, the wheat seed of full seed, in ultra-clean aseptic working platform, the NaClO solution with 5% soaks 20min, with distilled water flushing for several times.Under aseptic condition, take out, proceed in polypentenol sample, with distilled water, make blank, using 20mg/L IAA (heteroauxin) as positive control, each is treated to 100 seeds, establishes 3 repetitions; Seed soaks after 4h, uses distilled water flushing the surface of the seed, and seed is fitly arranged in and is placed in the auxiliary glass training shape ware that has 2 layers of gauze, puts into illumination box, under 25 ℃ of conditions, cultivates 5 days.Duration of germination is observed every day, keeps the skin wet, and a record germination grain number.The results are shown in Table 10.
The comparison of table 10 Polyprenols From Ginkgo Biloba L dialogue radish seed germination rate
Embodiment 4: the impact on plant cuttage root-taking
4-1: the impact on fairy bamboo cuttage root-taking
Selected fairy bamboo branch of the same size takes out under aseptic condition, proceeds in polypentenol sample, with distilled water, makes blank, usings 20mg/L IAA (heteroauxin) as positive control, and each is treated to 30, establishes 3 repetitions; Soak after 2h, be placed in test tube and cultivate, under 25 ℃ of conditions, cultivate 15 days, record the number of taking root.In the results list 11.
The impact of table 11 Polyprenols From Ginkgo Biloba L on fairy bamboo cuttage root-taking
4-2: the impact on rosemary, Xue MingRosma rinus officinalis cuttage root-taking
Selected rosemary, Xue MingRosma rinus officinalis branch of the same size takes out under aseptic condition, proceeds in polypentenol sample, with distilled water, makes blank, usings 20mg/L IAA (heteroauxin) as positive control, and each is treated to 30, establishes 3 repetitions; Soak after 2h, be placed in test tube and cultivate, under 25 ℃ of conditions, cultivate 15 days, record the number of taking root.In the results list 12.
The impact of table 12 Polyprenols From Ginkgo Biloba L on rosemary, Xue MingRosma rinus officinalis cuttage root-taking
Claims (5)
1. a preparation method who contains the plant growth regulator of polypentenol lipoid, is characterized in that being comprised of following steps:
(1) polypentenol lipoid extracts: will be rich in the fresh plant leaf of polypentenol lipoid, room temperature is dried in the shade, be crushed to the following powder of 100 order, add any solvent in anhydrous propanone or C1～C3 alcohol, leaf and solvent are 1: 20 in mass ratio, soaking at room temperature 10～72 hours, or extract 10～60 minutes through Microwave Extraction or ultrasonic at 10 ℃～80 ℃, repeat to extract twice, merge extract, vacuum reclaims organic solvent, and concentrate is polypentenol class fat ointment;
(2) polypentenol lipoid extract: it is 1: 6～30 anhydrous propanones that polypentenol class fat ointment adds mass ratio, and room temperature is dissolved as solution; 40～200 order diatomite mix with quartz sand 1: 1 in mass ratio～10, obtain mixed aid, mixed aid is 0.5～20 with polypentenol class fat ointment mass ratio: 100 mix, at-30 ℃～0 ℃, stir 2～30 hours, 3000～20000 revs/min of centrifuges filter, clear liquid reclaims organic solvent, and concentrate is polypentenol lipoid extract;
(3) preparation of urea alcoholic solution: urea is put into absolute methanol, bathe and to be heated to urea and all to dissolve filling nitrogen Water Under, wherein the w/v of urea and absolute methanol is 1: 1～10, and heating reflux temperature is 40～90 ℃;
(4) polypentenol lipoid extract urea inclusion preparation: add polypentenol lipoid extract and filler in urea alcoholic solution, polypentenol lipoid extract: filler: the mass ratio 0.1～1: 1～3: 10～40 of urea alcoholic solution, stirring and refluxing at 60-75 ℃ of temperature, be cooled to after room temperature, at-20～10 ℃ of deepfreezes to urea inclusion crystallization, then suction filtration, collects respectively crystal and filtrate, and crystal is polypentenol lipoid extract urea inclusion;
(5) polypentenol lipoid purifying: by polypentenol lipoid urea clathrate crystal dress post, with non-polar solven, carry out wash-out, elution volume is column volume 1-4 times, TLC detects, merge polypentenol lipoid elution fraction, after concentrating, obtain the polypentenol lipoid of purifying, through HPLC, detect, polypentenol lipoid purity is more than 50%, and the rate of recovery is more than 75%;
(6) polypentenol lipoid step (5) being obtained, mix by mass percentage with cosolvent, emulsifier and stabilizing agent and water, polypentenol lipoid 1%～20% in 100 parts of quality, cosolvent 1～50%, emulsifier 1～20%, stabilizing agent 1～10%, water surplus, at room temperature ultrasonic emulsification 10～30min, stirs, at low temperature below 4 ℃, preserve, make the plant growth regulator composition that contains polypentenol lipoid.
2. a kind of preparation method of the plant growth regulator that contains polypentenol lipoid according to claim 1, it is characterized in that plant leaf in step (1) is a kind of in ginkgo leaf, pine needle, mulberry leaf, the structure of its polypentenol lipoid is betulinol type ω-(trans)
2-(cis)
n-OH, wherein the scope of n is 10～20.
3. a kind of preparation method of the plant growth regulator that contains polypentenol lipoid according to claim 1, is characterized in that the filler in step (4) is one or more in silica gel, active carbon, polyamide, attapulgite, aluminium oxide, diatomite.
4. a kind of preparation method of the plant growth regulator that contains polypentenol lipoid according to claim 1, is characterized in that non-polar solven in step (5) is any in benzinum, n-hexane, ether.
5. a kind of preparation method of the plant growth regulator that contains polypentenol lipoid according to claim 1, it is characterized in that the cosolvent in step (6) is selected from one or more in methyl alcohol, ethanol, acetone, emulsifier is selected from one or more in Tween 80, OP-10, OP-21, X-100, and stabilizing agent is selected from one or more in n-butanol, propyl alcohol, glycerine.
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