CN102771496A - 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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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 fields such as agricultural chemicals exploitation, farmland chemical regulation and provenance agricultural.
Technical background
Polypentenol (polyprenols) extensively is present in the plants such as green confierophyte and ginkgo; Be to be the single lipids of structure, on structure, can divide: the n-OH of 3-(cis) n-OH of 2-(cis) n-OH of betulinol type ω-(trans), the pure type ω of luxuriant and rich with fragrance card-(trans) and the pure type ω of alltrans eggplant Buddhist nun-(trans) with the C5 isopentene group.
Polypentenol and ester class thereof are nonpolar ester type compounds; Its leaching process is: solvent lixiviate-hydrolysis-extraction-column chromatography separation 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, methyl alcohol-acetone, n-hexane-acetone.Employing benzinums such as Yang Xiaoming carry out lixiviate to ginkgo leaf; Obtain liposoluble substance, further adopt n-hexane to extract after the hydrolysis, obtain polypentenol and oil-soluble impurities with saturated sodium-chloride water solution washing organic facies; Separate with thin layer chromatography, and then adopt column chromatography purification.Li Chunbin etc. dissolve the ginkgo leaf ligroin extraction with acetone, carry out purification by silica gel column chromatography after the filtration, and with benzinum and benzinum: ether (25: 1) linear gradient elution, the polypenthylene acetic acid esters purity that obtains reaches more than 90%.Employing benzinums such as Sun Lei extract with 1: 7 solid-liquid ratio, and 10 hours, the extract obtained column chromatography for separation of carrying out got polypentenol.Employing benzinums such as Wang Chengzhang carry out lixiviate to ginkgo leaf, with EtOH-NaOH solution it are refluxed, and press 1: 5 preparation unsaponifiable matter with saponification agent again.Deng Yongzhi etc. carry out carbon dioxide supercritical extraction to ginkgo leaf, and then adopt benzinum and ether to dissolve in 19: 1 ratio, then separate with silica gel column chromatography, with the centrifugal removal of impurities of acetone solution eluate with obtain the polypentenol of purifying.
The growth and development of plant process receives the regulation and control of plant endogenous hormones usually, also receives the restriction of various unsuitable environmental conditions simultaneously, often causes the decline of growth rate and output, and the metabolic function downward modulation at each tissue of plant and position is one of main inducing wherein.Plant growth regulator is the chemicals of natural source; Be also referred to as plant hormone (for example 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 (biology of deriving of natural generation auxin, ethrel) that makes.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, also receives the adjusting and the control of plant growth substance simultaneously.Densely can produce the physiological effect of obviously showing down low, strong Physiology and biochemistry of plant generation and form are reacted.Plant promotes bolting to bloom at rooting of cuttings, and is solid, prevents to come off, and the vegetables fruit thinning is induced and breaking dormancy, promotes aspects such as maturation and enhancing 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 that the sustainable development of agricultural is significant.
At present, both at home and abroad the research of natural polypentenol is mainly concentrated on anti-hepatitis, biologically active such as antitumor.Research shows that the polypentenol compounds is a natural products; To human non-toxic, do not have mutagenesis, do not have teratogenesis and do not have carcinogenesis; Has tangible biologically active at aspects such as hepatitis virus resisting and AIDS virus and NACT leukemia; To immunologic function diseases such as hypertension, high fat of blood, diabetes, gout, lupus erythematosus, chronic hepatitis, suppressing tumour all has obvious effect with auxiliaryization, radiotherapy.Polypentenol all has the better inhibited effect to mouse transplantability hepatoma Heps, sarcoma s180 and Emhorn knurl EC.But polypentenol should be made in plant growth regulating almost not to be had.Korea S's power is held dragon extraction separation from the cotton plant leaf and is obtained undecaprenol and ten diterpene alcohol; Studied it and be applied to plant seed as plant growth regulator; The result shows that its concentration has good stratification effect [Chinese patent CN1529550A] to seeds such as corn, cucumber when 100ppm and 50ppm.And the polypentenol in this patent is the birch terpene alcohols polypentenol that is made up of 14～24 (is main with 17～19) individual isopentene group unit, extracts obtain different in its chemical constitution and the cotton plant leaf.Polypentenol is the compound in natural plants source, has safety, easily biological-degradable, characteristics such as environmentally friendly, therefore utilizes polypentenol exploitation natural green plant growth regulator to have important practical significance.
Summary of the invention
For realizing above-mentioned purpose, having invented a kind of content has plant growth regulator composition of polypentenol and preparation method thereof, it is characterized in that being made up of following steps:
(1) preparation of polypentenol: the plant leaf powder through extraction, saponification, washing, is got final product after the drying;
(2) preparation of urea alcoholic solution: urea is put into absolute methanol, be heated to urea and all dissolve filling under the nitrogen condition water-bath, wherein the w/v of urea and absolute methanol is 1: 10～5: 10, and the reflux temperature is 60～75 ℃;
(3) carry out the urea clathrate reaction: in the urea alcoholic solution, add polypentenol CE and filler; Polypentenol crude extract: filler: the ratio 0.5～1: 1～2: 10～40 of urea alcoholic solution; Stirring and refluxing under 60-75 ℃ of temperature, be cooled to room temperature after, separate out in the crystallization of-20～10 ℃ of deepfreeze to urea inclusions; Suction filtration is collected crystal and filtrating respectively then.
(4) crystal that step (3) is obtained is adorned post, at the uniform velocity injects chromatographic column with flowing phase and carries out wash-out, collects elution fraction; Merge, the polypentenol after obtaining making with extra care after concentrating is analyzed through HPLC; The purity of sample is more than 50%, and the rate of recovery is more than 80%.
(5) polypentenol that step (4) is obtained by percentage is: 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 ℃, is diluted to desired concn with deionized water before using; Stir, process the plant growth regulator composition that content has polypentenol.
2, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that plant leaf in the step (1) is a kind of in ginkgo leaf, pine needle, the 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, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged, it is characterized in that filler in the step (3) be in silica gel, active carbon, polyamide, attapulgite, aluminium oxide, the diatomite one or more.
4, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged, it is characterized in that flowing phase in the step (4) is a kind of in benzinum, n-hexane, the ether.
5, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that cosolvent in the step (5) selects one or more in methyl alcohol, ethanol, the acetone; Emulsifier selects one or more among Tween 80, OP-10, OP-21, the X-100, and stabilizing agent is selected from one or more in n-butanol, propyl alcohol, the glycerine.
6, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged, it is characterized in that being mixed with polypentenol behind the solution is 0.1～100mg/L as effective final concentration of plant growth regulator.
7, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that; Wine, immersion or
processing are irrigated, sprayed to plant growth regulator to plant, plant tissue or seed; Perhaps directly add the medium that comprises above-mentioned vegetable material; Handled 1～40 day every day 1～3 time continuously.
8, according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged, it is characterized in that, said plant or seed are a kind of in wheat, ternip, Yellow Emperor, a legendary ruler chrysanthemum, cucumber, fairy bamboo and the rosemary.
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 the mammal internal organs is approaching, and can in human body, be metabolized to the dolichol phosphate ester, as the biosynthetic carrier of glycoprotein.Therefore under various practice conditions such as farmland and greenhouse, use the low concentration polypentenol can not cause adverse effect to ecotope.
2) applied range this method is exclusively used in fields such as the nuisanceless production that comprises agricultural chemicals exploitation, farmland chemical regulation, provenance agricultural, group training, can regulate plant seed germination, takes root, the growth of crop and control is through saving effect such as growth.
Embodiment
Following examples are more of the present invention giving an example, and should not regarded as qualification of the present invention.
Embodiment 1: urea adduct method prepares the method for polypentenol
Selected four kinds of different types of absorption carriers such as silica gel, active carbon, polyamide, attapulgite, studied the purifying research of urea and absorption carrier respectively by 5 kinds of different quality proportionings such as mass ratioes 10: 1,5: 1,5: 2,5: 3,1: 1.
The purification result of the different proportionings of table 1 urea silica gel
By being carrier with silica gel shown in the table 1; Benzinum is that eluant, eluent can find out that through 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 merely 39.83%, and it is the highest that urea and silica gel mass ratio are that the fixing dress mutually for preparing at 5: 1 is lived the ginkgo leaf polypentenol purity that purifying obtains, and its purity is 72.34%; Along with its purity of increase of silica gel consumption diminishes again gradually, yield also descends thereupon gradually.Take all factors into consideration the factor of its purity and yield, the best purification condition that with silica gel is carrier is that urea silica gel mass ratio is 5: 1, and its purity is 72.34%, is greatly improved than the purity 37.9% of molecular clock product C.Firmly urea crystal in crystallization process is irregular for pure urea dress, and the inhomogeneous purification effect of dress post is relatively poor; Along with the consumption of silica gel increases urea at the silica gel area load, product purity improved gradually, was issued to the maximum of purity 5: 1 conditions; Along with the purity of the decline polypentenol of urea ratio reduces gradually; With the increase of the consumption of silica gel the suction-operated of polypentenol is strengthened and to cause yield to descend gradually.
The purification result of table 2 different carriers
By shown in the table 2; Silica gel, active carbon, attapulgite and four kinds of different adsorption carriers of polyamide have been selected; Mass ratio between urea and the carrier 5: 1; Find with silica gel to be that the product purity that obtains of carrier is higher through the contrast experiment, active carbon takes second place, and polyamide and attapulgite are that the product purity that carrier obtains improves not quite.The product colour that polyamide, attapulgite purifying obtain shows brownish red more deeply, and silica gel takes second place, and the product colour that activated carbon purification obtains is thin out to be buff.Take all factors into consideration with silica gel is that carrier is best.
Embodiment 2: the preparation of ginkgo leaf polypentenol emulsion
Extract the ginkgo leaf polypentenol that separation obtains with embodiment 1; With ginkgo leaf polypentenol 5g, tween 2.5g, ethanol 2.5mL and water 15mL; In the ultrasonic disruption appearance, carry out ultrasonic homogeneous; Obtain the polypentenol emulsion, and be mother liquor, be mixed with 5 concentration (10mg/L, 20mg/L, 50mg/L and 100mg/L) with it.
Embodiment 3: to the influence of crop seeds sprouting
3-1: to the influence of wheat seeds sprouting and growth of seedling
Selected size is consistent, the wheat seed of full seed, and in the aseptic workbench of ultra-clean, the NaClO solution soaking 20min with 5%, with distilled water flushing for several times.Under aseptic condition, take out, change in the polypentenol sample, make blank with distilled water, as positive control, each is treated to 100 seeds with 20mg/L IAA (heteroauxin), establishes 3 repetitions; Seed is used the distilled water flushing the surface of the seed after soaking 4h, seed fitly is arranged in places the auxilliary glass training shape ware that 2 layers of gauze are arranged, and 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 root system vigor.The result lists among the table 3-8.
Table 3 ginkgo leaf polypentenol is to the comparison of wheat seed germinating rate
Table 4 ginkgo leaf polypentenol is to the comparison of wheat seed height of seedling
The comparison that table 5 ginkgo leaf polypentenol is long to the wheat seed root
Table 6 ginkgo leaf polypentenol is to the comparison of wheat seed amylase activity
Table 7 ginkgo polypentenol is to the comparison of wheat seed root system vigor
3-2: to the influence of Yellow Emperor, a legendary ruler chrysanthemum seed germination
Selected size is consistent, the wheat seed of full seed, and in the aseptic workbench of ultra-clean, the NaClO solution soaking 20min with 5%, with distilled water flushing for several times.Under aseptic condition, take out, change in the polypentenol sample, make blank with distilled water, as positive control, each is treated to 100 seeds with 20mg/L IAA (heteroauxin), establishes 3 repetitions; Seed is used the distilled water flushing the surface of the seed after soaking 4h, seed fitly is arranged in places the auxilliary glass training shape ware that 2 layers of gauze are arranged, and puts into illumination box, under 25 ℃ of conditions, cultivates 10 days.Duration of germination is observed every day, keeps the skin wet a record germination grain number.The result lists in the table 8.
Table 8 ginkgo leaf polypentenol is to the comparison of Yellow Emperor, a legendary ruler chrysanthemum percentage of seedgermination
3-3: the influence that the dialogue radish seed is sprouted
Selected size is consistent, the wheat seed of full seed, and in the aseptic workbench of ultra-clean, the NaClO solution soaking 20min with 5%, with distilled water flushing for several times.Under aseptic condition, take out, change in the polypentenol sample, make blank with distilled water, as positive control, each is treated to 100 seeds with 20mg/L IAA (heteroauxin), establishes 3 repetitions; Seed is used the distilled water flushing the surface of the seed after soaking 4h, seed fitly is arranged in places the auxilliary glass training shape ware that 2 layers of gauze are arranged, and puts into illumination box, under 25 ℃ of conditions, cultivates 5 days.Duration of germination is observed every day, keeps the skin wet a record germination grain number.The result lists in the table 9.
The comparison of table 9 ginkgo leaf polypentenol dialogue radish seed germination rate
3-4: to the influence of germination of cucumber seeds
Selected size is consistent, the wheat seed of full seed, and in the aseptic workbench of ultra-clean, the NaClO solution soaking 20min with 5%, with distilled water flushing for several times.Under aseptic condition, take out, change in the polypentenol sample, make blank with distilled water, as positive control, each is treated to 100 seeds with 20mg/L IAA (heteroauxin), establishes 3 repetitions; Seed is used the distilled water flushing the surface of the seed after soaking 4h, seed fitly is arranged in places the auxilliary glass training shape ware that 2 layers of gauze are arranged, and puts into illumination box, under 25 ℃ of conditions, cultivates 5 days.Duration of germination is observed every day, keeps the skin wet a record germination grain number.The result lists in the table 10.
The comparison of table 10 ginkgo leaf polypentenol dialogue radish seed germination rate
Embodiment 4: to the influence of plant cuttage root-taking
4-1: to the influence of fairy bamboo cuttage root-taking
Selected fairy bamboo branch of the same size takes out under aseptic condition, changes in the polypentenol sample, makes blank with distilled water, and as positive control, each is treated to 30 with 20mg/L IAA (heteroauxin), establishes 3 repetitions; After soaking 2h, place test tube to cultivate, cultivated 15 days under 25 ℃ of conditions, write down the number of taking root.In the results list 11.
Table 11 ginkgo leaf polypentenol is to the influence of fairy bamboo cuttage root-taking
4-2: to the influence of rosemary, cuttage root-taking
Selected rosemary, branch of the same size takes out under aseptic condition, changes in the polypentenol sample, makes blank with distilled water, and as positive control, each is treated to 30 with 20mg/L IAA (heteroauxin), establishes 3 repetitions; After soaking 2h, place test tube to cultivate, cultivated 15 days under 25 ℃ of conditions, write down the number of taking root.In the results list 12.
Table 12 ginkgo leaf polypentenol is to the influence of rosemary, cuttage root-taking
Claims (7)
1. a content has plant growth regulator composition of polypentenol and preparation method thereof, it is characterized in that being made up of following steps:
The first step, the 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 orders, add any solvent in anhydrous propanone or the C1～C3 alcohol, leaf and solvent are 1: 20 by mass ratio; Soaking at room temperature 10～72 hours, or 10 ℃～80 ℃ through Microwave Extraction or Extraction by Ultrasound 10～60 minutes, repeat to extract twice; Merge extract, vacuum reclaims organic solvent, and concentrate is a 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 by mass ratio 1: 1～10 with quartz sand; Obtain mixed aid; Mixed aid and polypentenol class fat ointment mass ratio are to mix at 0.5～20: 100, stir 2～30 hours at-30 ℃～0 ℃, and 3000～20000 rev/mins of centrifuges filter; Clear liquid reclaims organic solvent, and concentrate is a polypentenol lipoid extract;
(3) preparation of urea alcoholic solution: urea is put into absolute methanol, be heated to urea and all dissolve filling under the nitrogen condition water-bath, wherein the w/v of urea and absolute methanol is 1: 1～10, and the reflux temperature is 40～90 ℃;
(4) polypentenol lipoid extract urea inclusion preparation: in the urea alcoholic solution, add polypentenol lipoid extract and filler; Polypentenol lipoid extract: filler: the mass ratio 0.1～1: 1～3: 10～40 of urea alcoholic solution, stirring and refluxing under 60-75 ℃ of temperature, be cooled to room temperature after; Separate out in the crystallization of-20～10 ℃ of deepfreeze to urea inclusions; Suction filtration is collected crystal and filtrating respectively then, and crystal is a polypentenol lipoid extract urea inclusion;
(5) polypentenol lipoid purifying: with polypentenol lipoid urea clathrate crystal dress post, carry out wash-out with non-polar solven, elution volume is column volume 1-4 times; TLC detects; Merge polypentenol lipoid elution fraction, obtain the polypentenol lipoid of purifying after concentrating, detect through HPLC; Polypentenol lipoid purity is more than 50%, and the rate of recovery is more than 75%;
(6) the polypentenol lipoid that step (5) is obtained mixes with cosolvent, emulsifier and stabilizing agent and water by mass percentage, polypentenol 1%～20% in 100 parts of quality; Cosolvent 1～50%, emulsifier 1～20%, stabilizing agent 1～10%; Water surplus, at room temperature ultrasonic filter emulsification 10～30min stirs; Preserve at low temperature below 4 ℃, process the plant growth regulator composition that content has polypentenol.
2. according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that plant leaf in the step (1) is a kind of in ginkgo leaf, pine needle, the 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. according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged, it is characterized in that filler in the step (4) be in silica gel, active carbon, polyamide, attapulgite, aluminium oxide, the diatomite one or more.
4. according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged, it is characterized in that in the non-polar solven benzinum, n-hexane, ether in the step (5) any.
5. according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that cosolvent in the step (6) selects one or more in methyl alcohol, ethanol, the acetone; Emulsifier selects one or more among Tween 80, OP-10, OP-21, the X-100, and stabilizing agent is selected from one or more in n-butanol, propyl alcohol, the glycerine.
6. according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that; Thin up to effective final concentration was 0.1～100mg/L when the plant growth regulator composition of polypentenol was used, and wine, immersion or seed soaking are irrigated, sprayed to plant, plant tissue or seed handle, and perhaps directly added the medium that comprises above-mentioned vegetable material; Handled 1～40 day every day 1～3 time continuously.
7. according to the said a kind of content of claim 1 plant growth regulator composition of polypentenol and preparation method thereof is arranged; It is characterized in that said plant, plant tissue or seed are a kind of in wheat, ternip, Yellow Emperor, a legendary ruler chrysanthemum, cucumber, fairy bamboo and the rosemary.
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| CN103145528A (en) * | 2013-01-24 | 2013-06-12 | 中国林业科学研究院林产化学工业研究所 | Method of preparing high-purity polyprenol lipid by means of both high-speed countercurrent chromatography and high performance liquid chromatography |
| CN106857695A (en) * | 2016-12-31 | 2017-06-20 | 新昌县迪斯曼科技有限公司 | Plant growth regulator composition and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103145528A (en) * | 2013-01-24 | 2013-06-12 | 中国林业科学研究院林产化学工业研究所 | Method of preparing high-purity polyprenol lipid by means of both high-speed countercurrent chromatography and high performance liquid chromatography |
| CN103145528B (en) * | 2013-01-24 | 2015-02-18 | 中国林业科学研究院林产化学工业研究所 | Method of preparing high-purity polyprenol lipid by means of both high-speed countercurrent chromatography and high performance liquid chromatography |
| CN106857695A (en) * | 2016-12-31 | 2017-06-20 | 新昌县迪斯曼科技有限公司 | Plant growth regulator composition and preparation method thereof |
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| CN102771496B (en) | 2014-04-09 |
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