• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Use of non-prolific cyclic amino acids to increase plant tolerance to osmotic stress conditions. The present invention proposes the use of non-proline cyclic amino acids of general formula (I), wherein n, x, y and z have the meaning described in the description, to increase the tolerance of plants to osmotic stress conditions, which have their origin in the lack of availability of water from the environment. The non-proline amino acids that are used in the invention are of natural origin and have a much higher effectiveness than other amino acids already known and used for the same purpose, so it is considered that this invention can be very useful to avoid economic losses caused by declining productivity in agricultural crops. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2638213A1
    申请号:ES201630317
    申请日:2016-03-17
    公开日:2017-10-19
    发明作者:David JIMÉNEZ ARIAS；Andrés BORGES RODRÍGUEZ；Alicia Boto Castro；Francisco VALDÉS GONZÁLEZ；José Antonio PÉREZ PÉREZ；Juan Cristo Luis Jorge
    申请人:Consejo Superior de Investigaciones Cientificas CSIC；Universidad de La Laguna；
    IPC主号:
    专利说明:

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    USE of non-prolific cyclic amino acids to increase the
    TOLERANCE OF PLANTS TO OSMOTIC STRESS CONDITIONS
    D E S C R I P C I O N
    SECTOR OF THE INVENTION
    The present invention relates to the use of organic molecules to increase the tolerance of plants to osmotic stress conditions caused by the difficulty in accessing the water in the environment, such as those caused by saline stress or water deficit. Based on the above, this invention can be included in the area of the application of compounds and substances to favor the development of plants under the described conditions of osmotic stress.
    STATE OF THE TECHNIQUE
    The lack of accessibility to water by plants is one of the factors that most decisively influence the decline in productivity of agricultural crops. This lack of accessibility to water may be due to both weather, agricultural or hydrological dry conditions, which in short refers to a water deficit in the environment, as well as physiological drying.
    Physiological drying occurs when soluble salts are found in high concentrations in the soil solution, limiting water intake by the plant due to the low water potential that is generated.
    In any of the drying situations described above, an osmotic stress occurs in plants, which results in the generation of a very similar physiological, biochemical and molecular response that affects their development (Sairam and Tyagi, 2004. Current Science 86 (3), 407-421).
    It is known that plants, and as a survival strategy in these stress situations, can adjust their osmotic potential by generating a water potential lower than that of the soil solution, in order to access the water present in it (Munns and Tester, 2008 Annual Review of Plant Biology 59: 651-681).
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    It is also known that the adaptation of plants to different stress conditions can be stimulated by means of chemical compounds to try to cancel the negative effect on their development, so for example, in the patent ES2332494B1 the use of menadione is claimed, a derivative of vitamin K, to increase the tolerance of plants to osmotic stress caused by salinity.
    In relation to the use of amino acids to improve plant development conditions, it is widely known that mixtures of this type of organic molecules from protein hydrolyzate have been used in Europe since 1968 to: fertilize the soil, such as pesticides, as herbicides, as fungicides and as growth regulators through a nutritional effect of crops.
    There are also documents that refer to the use of amino acids to increase tolerance to situations of low water availability due to physiological drought. In this regard, the work of El-Samad et al. (2011. Journal of Medicinal Plants Research 5:24, 5692-5699) which refers to the use of non-cyclic amino acids such as phenylalanine or proline; or patent application document US2009054241A1, in which a proline derivative, namely hydroxyproline, is used. However, in any of these cases, the effectiveness in relation to the increase in tolerance is still limited.
    Based on the above, the search for new amino acids is considered of interest, which when applied to plants, are able to stimulate their natural mechanisms to increase tolerance to osmotic stress conditions.
    EXPLANATION OF THE INVENTION
    It is considered that the problem that solves the invention is the selection of organic molecules, specifically amino acids, which when applied to plants, allow to increase their tolerance to the conditions of osmotic stress and therefore do not see their productivity diminished in relation to non-submitted plants To said stress.
    The inventors have observed that some amino acids, specifically the non-prolific cyclic amino acids of general formula (I), as an example of which include pipecolic acid and pyroglutamic acid, are capable of stimulating
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    Natural mechanisms of plants that allow them to overcome osmotic stress conditions, significantly increasing their biomass production in these adverse conditions and bringing it closer to the values of control plants not subjected to such stress (see Example 2). The inventors have also verified that the use of other different amino acids, used under the same conditions of experimentation, do not achieve a recovery of biomass production with respect to a control or if they achieve it is to a lesser extent (see examples 1 to 3) .
    The advantages of the use of the non-prollolic clinical amino acids of general formula (I) that are included in the scope of the present invention are:
    - they have a clearly superior effect than other amino acids described in the state of the art, such as alanine or hydroxyproline, have shown in improving tolerance to osmotic stress conditions;
    -that is natural amino acids or biodegradable derivatives that minimize environmental impact; Y
    - enable safe handling by operators during the application.
    In a first aspect, the invention relates to the use of at least one compound of formula (I) to increase the tolerance of plants to osmotic stress conditions.
    Z
    [
    image 1
    image2
    OR
    X
    (I)
    where:
    n represents an integer between 0 and 1; Y represents -C = O or -CH2;
    X represents -OH, -O-C1-4alkyl or -NH-C1.4alkyl; and Z represents H, -OH, -SH or -S-C1-4alkyl,
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    with the proviso that L-proline and D-proline are excluded from the definition of a compound of formula (I).
    In another embodiment the invention relates to the use of a compound of formula (I) as defined above where: n represents a number between 0 and 1;
    Y represents -C = O or -CH2;
    X represents -OH, -O-C1-4alkyl or -NH-C1-4alkyl; and Z is H,
    with the proviso that L-proline and D-proline are excluded from the definition of a compound of formula (I).
    In another embodiment the invention relates to the use of a compound of formula (I) as defined above where: n represents a number between 0 and 1;
    Y represents -C = O or -CH2;
    X represents -OH; Y
    Z is H,
    with the proviso that L-proline and D-proline are excluded from the definition of a compound of formula (I).
    In another embodiment the invention relates to the use of a compound of formula (I) as defined above where the compound of formula (I) is the compound of formula (II).
    image3
    In another embodiment the invention relates to the use of a compound of formula (I) as defined above where the compound of formula (I) is the compound of formula (III).
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    image4
    (III)
    Some compounds of formula (I) have chiral centers that give rise to several stereoisomers. The present invention describes each of these stereoisomers and mixtures thereof.
    Also included in the scope of the invention are the water-soluble derivatives of the amino acid of the invention.
    The "conditions of osmotic stress" are caused by a difficulty in accessing the water available in the environment that houses a plant and that the expert in the state of the art knows as a common element to circumstances of meteorological, agricultural, hydrological dryness ( situations of hydric deficit) or physiological (salinity situations), and that has similar effects on the activation of defense mechanisms of the plant and on the decrease of its development (Sairam and Tyagi, 2004. Current Science 86 (3), 407 -421).
    The results included in this document (see Example 2), have shown that the amino acid of the invention is effective in increasing tolerance under conditions of osmotic stress, such as those caused for example in salinity conditions, so it is considered that It must also be effective under conditions of osmotic stress caused by water deficit.
    In another embodiment the invention relates to the use of a compound of formula (I) as defined above to increase tolerance to osmotic stress caused by a water deficit.
    In another embodiment the invention relates to the use of a compound of formula (I) as defined above to increase tolerance to osmotic stress produced by salinity.
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    As mentioned above, some of the compounds of the present invention may exist as several diastereoisomers and / or several optical isomers. The diastereoisomers can be separated by conventional techniques such as chromatography or fractional crystallization. Optical isomers can be solved by conventional optical resolution techniques to give optically pure isomers. This resolution can be carried out in any of the intermediate products of a compound of formula (I). Optically pure isomers can also be obtained individually using enantioselective synthesis. The present invention covers all individual isomers as! such as mixtures thereof (for example racemic mixtures or mixtures of diastereoisomers), both obtained by synthesis and by physical mixture thereof.
    In a second aspect, the invention relates to a method for improving tolerance to osmotic stress conditions, hereinafter method of the invention, which comprises administering to the plant an effective dose of at least one compound of formula (I) such and as defined above.
    Although the person skilled in the art will know that it is possible to use the amino acid of the invention in any support that favors its penetrability in the plant material, preferably, the method of the invention comprises using the compound of formula (I) in aqueous solution. .
    The method of the invention also includes using the amino acid of the invention together with various vehicles and agents that facilitate its conservation, handling and application.
    In another embodiment the invention relates to the method defined above where the compound of formula (I) can be used in conjunction with another active ingredient. Examples of additional active ingredient are, by way of indication and not limitation, nematicides, insecticides, acaricides, fungicides, bactericides, herbicides, growth regulators, fertilizers, synergists, fertilizers and soil conditioners, and preferably where the additional active ingredient is selected from Nematicide, insecticide, acaricide, fungicide, bactericide and herbicide.
    Although the addition of only one of the amino acids of the invention causes beneficial effects on increasing tolerance to situations of osmotic stress,
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    increasing its biomass production to values very similar to those of plants that are not subjected to this stress, the invention also includes the simultaneous combination of more than one compound of formula (I), such as the compound of formula (II), also referred to as pipecollnic acid, and the compound of formula (III), also referred to as pyroglutamic acid.
    As explained above, in the description of the use of the amino acid of the invention (compound of formula (I)), and in a consistent manner, the method of the invention is applicable to increase the tolerance to osmotic stress caused by a water deficit or salinity.
    The effectiveness of the method of the invention is evident when the reduction of the negative effects caused by osmotic stress is verified, after the application of the amino acid of the invention in plants treated with moderate doses of NaCl (50 mM) (Attia et al, 2008 Physiology Plantarum 132: 293-305), which obviously increases biomass production to values close to those obtained by control plants without osmotic stress. It is further verified that the application of the amino acid of the invention causes a response of a systematic nature and, consequently, its effects extend to the rest of the plant from the roots.
    In the above definitions, the term C1-4alkyl, as a group or part of a group, means a straight or branched chain alkyl group containing 1 to 4 C atoms; and includes the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl groups.
    In this document, "plant" means indistinctly both an individual and a plurality thereof, whether considered in its entirety, that is, including air part and radical part irrespective of their stage of development, or partially considered , that is, any portion thereof that can be used as plant material for reproduction or multiplication.
    By "plant material of reproduction" means both the seed and the fruit that comprises it.
    The term "multiplication plant material" means any fragment of a plant from which at least one new specimen can be obtained and is normally used as a basis in propagation techniques, such as propagation
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    by layers, cuttings, stakes, stolons, buds, rhizomes, tubers, bulbs or corms; graft propagation; micropropagation; or propagation by in-vitro culture.
    As the expert in the state of the art knows, depending on the stage of development of the plant or the type of plant material, different techniques of application of phytosanitary products are possible. Thus, for example, for plants already established in the field, for application in the aerial part, the most suitable techniques may include spraying the amino acid of the invention on the leaves, or injection into the stem, while for the root part, the application It can be done by incorporation into the irrigation water or the substrate that houses the plant.
    However, for plant material in stages prior to putting it in the field, in addition to the prior art, it is also possible to immerse the radical part in a solution that comprises the amino acid of the invention or the total immersion of the plant material, either of reproduction or multiplication. Preferably, the application is by immersion of the radical part.
    Examples of cultivation in which the method of the invention can be applied are any monocot crop or dicot crop, for indicative and non-limiting purposes, cereal, fruit, vegetable, vegetable, or ornamental plant crops.
    In another embodiment the invention relates to the method as defined above, which comprises the application in aqueous solution of the compound of formula (I) by immersion of the root system.
    In another embodiment the invention relates to the method as defined above, which comprises the application in aqueous solution of the compound of formula (I) by immersion of the seeds.
    In another embodiment the invention relates to the method as defined above, wherein the compound of formula (I) is the compound of formula (II).
    In another embodiment the invention relates to the method as defined above, wherein the compound of formula (I) is the compound of formula (III).
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    The "effective dose" may optionally increase or decrease according to the amino acid of the selected invention, of the plant material, of its stage of development, of the type of formulation, of the time, of the place, of the frequency of application and of the degree of osmotic stress. .
    In a particular embodiment of the method of the invention, the amino acid of the invention is used in a concentration range of 0.1 pM to 3 M.
    Throughout the description and the claims, the word "comprises" and its variants are not intended to exclude other technical characteristics. For the person skilled in the art, other aspects, advantages and characteristics of the invention will be derived in part from the description and in part of the practice of the invention The following examples are provided by way of illustration, and are not intended to be limiting of the present invention.
    EMBODIMENTS OF THE INVENTION
    The conditions described below were used as the basis for all the examples included below. The culture conditions, such as the nutrient solution and the substrate used have been optimized for the realization of this type of experiments. Similarly, the dose of NaCl used has been optimized for this type of experiments since 50 mM allows to assess whether a treatment is capable of increasing salinity tolerance (Jimenez-Arias et al., 2015. Environmental and Experimental Botany 120 , 23-30).
    For the cultivation of the Arabidopsis thaliana plants necessary for the tests, a hydroponic culture system was used. This system was established in hydroponic cuvettes with 1.9 L capacity (Araponics®) where 18 plants were grown per container. A mixture of sand from two different grains was used as a physical substrate. The seeds were sown in seed containers (seed-holders), which were deposited for a week in a small greenhouse, consisting of a high density polyethylene tray with river sand (washed sillcea sand, with medium grain size) with distilled water sterile covered with a transparent plastic sheet, which was deposited in a culture chamber at 22 ± 2 ° C, with a photoperiod of 16 hours of light (100-110 pmol m-2 s-1 of PAR) and with 100% relative humidity After a week, the seed-holders with the seedlings were
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    transferred to the hydroponic cuvettes under the same photoperiod and light intensity conditions, but with 60-70% relative humidity. The seedlings remained without aeration during the first week, from which the solution (Table 1) was generously aerated by aeration pumps and was renewed every 7 days.
    Table 1. Hydroponic solution used in the experiments
     Macronutrients (mM)  Micronutrients (pM)
     KNO3 (1.25)  H3BO3 (50)
     KH2PO4 (0.5)  MnSO4 x H2O (10)
     MgSO4 x 7H2O (0.75)  ZnSO4 x 7H2O (2)
     Ca (NO3) 2 x 4H2O (0.75)  CuSO4 x 5H2O (1.5) (NH4) aMo7O24 x 4H2O (0.075) Sequestrene® (44.8)
    Example 1. Effect of alanine on the response of A. thaliana to saline stress caused by the addition of NaCl
    To check if the fundamental structure of the amino acids produces protective effects against saline stress, a simple amino acid such as alanine was used.
    In this way, 21-day plants were treated for 24 hours in nutrient solution enriched with a concentration of 2.5 mM alanine. Subsequently, the plants were deposited in normal nutritional solution for 24 hours and subsequently grew for 7 days in nutrient solution with or without a contribution of 50 mM NaCl. This experiment was repeated twice, using 12 plants per experiment, the value shown in Table 2 being the average of 24 plants for each of the conditions.
    Subsequently, the wet weight of the aerial part of the plants was determined.
    The following table (Table 2) shows the results of the amino acid alanine on plant development.
    Table 2: Effects of alanine on growth in optimal and saline conditions.
     Untreated Alanina Salt Alanina-salt
     Fresh Weight (mg plant)  130 ± 16 142 ± 8 52 ± 8 ** 36 ± 2 **
     TCR  0.53 0.58 0.21 ** 0.11 **
    The data shown are the average of two independent experiments with 24 plants 5 in total. The ** show significant differences with respect to the control group with a p <0.01. TCR: Relative growth rate (T.C.R = (ln Ps2-ln Ps1) / (T2-T1); ln being logarithm neperian; Ps dry weight and T time).
    As can be seen, the structure represented by the amino acid alanine was not able to promote growth, nor increase tolerance to salinity, it seems, it seems that it harms the plants before the same dose of salt.
    Example 2. Effect of pyroglutamic acid or pipecollnic acid on the response of A. thaliana to saline stress caused by the addition of NaCl
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    Plants of 21 days were treated for 24 hours in nutrient solution enriched with a concentration of 2.5 mM pyroglutamic acid or pipecollnic acid. Subsequently the plants were deposited in normal nutritional solution for 24 hours and subsequently grew for 7 days in nutrient solution with or without a contribution of 50 mM NaCl. This experiment was repeated twice, using 12 plants per experiment, the value shown in Table 2 being the average of 24 plants for each of the conditions.
    The fresh weight of the specimens is shown in the following table (Table 3).
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    Table 3: Effects of pyroglutamic acid and Ac. Pipecolinico on growth in optimal and saline conditions
     Untreated Pyroglutamic acid Pipecolinic acid Salt Pyroglutamic acid Pipecolinic acid - salt
     Fresh weight  158.3 ± 20 183.9 ± 15 145.9 ± 22 90 ± 18 ** 170.4 ± 15 133.9 ± 21
     (mg plant)
     TCR  0.56 0.56 0.46 0.23 0.49 0.45
    The data shown are the average of two independent experiments with 24 plants in total. The ** show significant differences with respect to the control group with a p <0.01. TCR: Relative growth rate (T.C.R = (ln Ps2- ln Ps1) / (T2-T1); being ln 5 logarithm neperiano; Ps dry weight and T time).
    As can be seen, the salt again significantly decreased the growth, as shown by the fresh weight and the relative growth rate of the plant, after one week of being subjected to saline stress. This did not occur significantly in those plants that were previously treated with 2.5 mM pyroglutamic acid or 2.5 mM pipecollnic acid, so its effect on increasing tolerance to saline stress is proven.
    Example 3. Comparison of the effect of pyroglutamic acid, pipecollnic acid 15 or hydroxyproline on the response of A. thaliana to saline stress caused by the addition of NaCl
    In order to demonstrate that the utilization of these compounds is more effective than the use of other amino acids already described, such as hydroxyproline 20 (US20090054241 A1), the effect of a 2.5 mM dose treatment was compared. from
    pyroglutamic acid or pipecollnic acid, or hydroxyproline.
    The plants were deposited in nutrient solution enriched with any of the compounds previously noted for 24 hours and subsequently grew 25 for 7 days in nutrient solution with a contribution of 50 mM NaCl. As a control, plants grown on nutrient solution and NaCl were used. This experiment was repeated twice, using 12 plants per experiment, the value shown in Table 2 being the average of 24 plants for each of the conditions.
    30 In order to illustrate the defense against saline stress, two measures are used. The values for the Sensitivity Index (S.I) described by Saadallah et al. (2001) are shown first. The higher the negative value of the S.I. The greater the negative effect of salinity on the plant. The second measure is a percentage of
    reduction of the relative growth rate of the plant subjected to saline stress conditions.
    The following table (Table 4) shows the results.
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    Table 4: Effects of pyroglutamic acid, pipecolinic acid or hydroxyproline on the Sensitivity Index
     Control Pyroglutamic acid Pipecolinic acid Hydroxyproline
     YES  -0.70 -0.1 ** -0.07 ** -0.25 **
     % reduction TCR  62.00 10.22 ** 8.12 ** 24.34 **
    10 (SI = PSs-PSc / PSc; being dry weight plants in saline conditions; dry weight under control conditions) and the percentage of reduction of the relative growth rate (% Red. TCR = (TCRs-TCRc / TCRc) x100; TCRs being growth rate of plants grown under saline conditions; TCRc growth rate of plants grown under control conditions). The data shown are the average of two independent experiments with 24 plants in total. The ** show significant differences with respect to the control group with a p <0.01.
    As can be seen, the use of any of the two compounds considerably increased the tolerance with respect to hydroxyproline, so the use of these compounds at the same dose was more beneficial for the cultivation of the plant under conditions of saline stress. .
    权利要求:
    Claims (12)
    [1]
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    R E I V I N D I C A C I O N E S
    1.- Use of at least one compound of formula (I) to increase the tolerance of plants to osmotic stress conditions
    Z
    [
    image 1
    image2
    OR
    X
    (I)
    where:
    n represents an integer between 0 and 1;
    Y represents -C = O or -CH2;
    X represents -OH, -O-C1-4alkyl or -NH-C1-4alkyl; and Z represents H, -OH, -SH or -S-C1-4alkyl,
    with the proviso that L-proline and D-proline are excluded from the definition of a compound of formula (I).
    [2]
    2. The use of a compound of formula (I) according to claim 1, wherein the compound of formula (I) is the compound of formula (II):
    image3
    (II).
    [3]
    3. The use of a compound of formula (I) according to claim 1, wherein the compound of formula (I) is the compound of formula (III).
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    image4
    (III).
    [4]
    4. - The use of a compound of formula (I) according to any of claims 1 to 3, characterized in that the osmotic stress is produced by a water deficit or by salinity.
    [5]
    5. - Method for increasing the tolerance of plants to osmotic stress conditions, characterized in that it comprises administering to the plant an effective dose of at least one compound of formula (I) according to any of claims 1 to 3.
    [6]
    6. - The method according to claim 5, characterized in that the compound of formula (I) is used in aqueous solution.
    [7]
    7. - The method according to any of claims 5 or 6, characterized in that additionally compound of formula (I) an active ingredient is used which selects a nematicide, insecticide, acaricide, fungicide, bactericide and herbicide.
    [8]
    8. - The method according to any of claims 5 to 7, characterized in that the osmotic stress is produced by a water deficit or by salinity.
    [9]
    9. - The method according to any of claims 5 to 8, characterized in that the application of the compound of formula (I) is carried out using a technique selected for spraying, injection, irrigation, immersion and application on substrate.
    [10]
    10. - The method according to any of claims 5 to 9, characterized in that the application of the compound of formula (I) is carried out with a dose between 0.1 pM and 3 M.
    [11]
    11. - The method according to any of claims 5 to 10, characterized in that:
    - the compound of formula (I) is selected from a compound of formula (II) and a compound of formula (III); Y
    - The application is made by immersion in the root system.
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    [12]
    12. - The method according to any of claims 5 to 10, characterized in that:
    - the compound of formula (I) is selected from a compound of formula (II) and a compound of formula (III); Y
    - and the application is done by immersion of seeds.
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