Microorganism-derived cyclic octapeptide compound and application thereof
By using surugamides, a cyclic octapeptide compound isolated from deep-sea Streptomyces, as a plant growth regulator, the problem of insufficient application of marine natural products as plant growth regulators in existing technologies has been solved, and a significant effect on promoting the growth of plant roots and stems has been achieved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SHENYANG INST OF APPL ECOLOGY CHINESE ACAD OF SCI
- Filing Date
- 2026-01-12
- Publication Date
- 2026-05-12
AI Technical Summary
There are few reports on the application of marine natural products as plant growth regulators in the existing technology, and there is a lack of effective compounds to promote plant growth.
Surugamides, a cyclic octapeptide isolated from the deep-sea Streptomycessp. NA13, were used as plant growth regulators to promote the growth of plant roots and stems.
Cyclic octapeptide compounds surugamides significantly promote the growth of plant roots and stems, exhibiting similar activity to traditional plant growth regulators gibberellin and trans-zeatin. In particular, surugamide A is more effective than other compounds at certain concentrations.
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Abstract
Description
Technical Field
[0001] This invention relates to the field of microbial drug technology, specifically to a microbial-derived cyclic octapeptide compound and its applications. Background Technology
[0002] According to a 2019 UN report, the global population is projected to reach 9.7 billion by 2050, an increase of approximately 2 billion from the current population. To meet the growing food demand, crop yields must be significantly increased. Plant growth regulators play a crucial role in improving crop quality and yield, as well as enhancing agricultural practices. The use of plant growth regulators began in the 1930s with products such as ethylene and acetylene. Since then, many natural plant growth regulators that promote plant growth have been discovered, including gibberellins (GA), auxins, abscisic acid, brassinosteroids, and cytokinins. The global market for plant growth regulators has experienced substantial growth, with sales increasing from approximately $1.5 billion in 2015 to approximately $2-3 billion in 2022. Consequently, the demand for plant growth regulators has attracted widespread attention from academics.
[0003] In recent years, marine natural products have attracted widespread attention due to their remarkable structural diversity and potent bioactivity. While marine natural products have been extensively studied as insecticides and fungicides, surprisingly, there are few reports on their use as plant growth regulators. This invention patent provides [the following information] isolated from deep-sea Streptomyces. Streptomyces Application of four cyclic octapeptide compounds, surugamides, in sp. NA13 as plant growth regulators. Summary of the Invention
[0004] The purpose of this invention is to provide a microbial-derived cyclic octapeptide compound and its application.
[0005] To achieve the above objectives, the present invention adopts the following technical solution: Application of a microbial-derived cyclic octapeptide compound, as shown in Formula I, in its use as a plant growth regulator.
[0006] The application of the microbial-derived cyclic octapeptide compound shown in Formula I as a plant root growth regulator.
[0007] The microbial-derived cyclic octapeptide compound shown in Formula I is used as a plant stem growth regulator.
[0008] The microbial-derived cyclic octapeptide compound represented by Formula I Formula I In the formula, R1, R2, and R3 can be the same or different and are selected from H or methyl.
[0009] Further preferably, the compound is The above-mentioned compounds were isolated from deep-sea Streptomyces. Streptomyces It was obtained by fermentation, separation and purification of sp. NA13.
[0010] A plant growth regulator containing a microbial-derived cyclic octapeptide compound of Formula I.
[0011] Advantages of this invention: This invention is the first to isolate cyclic octapeptide from a bacterial strain, and the obtained cyclic octapeptide compound can promote plant growth, making it an ideal compound for promoting the growth of crop roots and stems. Attached Figure Description
[0012] Figure 1 To obtain the effects of cyclic octapeptides surugamides and positive controls gibberellin and trans-zeatin on rice root growth in this embodiment of the invention, groups a and b were surugamide A, surugamide B, trans-zeatin and gibberellin, respectively, compared with the blank control.
[0013] Figure 2 To obtain the effects of cyclic octapeptides surugamides and positive controls gibberellin and trans-zeatin on maize root growth in this embodiment of the invention, groups ej were surugamide A, surugamide B, surugamide C, surugamide D, trans-zeatin and gibberellin compared with the blank control. Detailed Implementation
[0014] To better understand the content of this invention, further explanation is provided below with reference to specific embodiments, but the scope of protection of this patent is not limited thereto.
[0015] The microbial cyclic octapeptide compounds shown in Formula I in the following examples are described in the examples of application number 202211283332.6, entitled "Preparation and Application of a Deep-Sea Streptomyces and its Antifeedant and Antifungal Active Substances", compounds 1-4; structural analysis of the obtained cyclic octapeptide compounds 1-4: The proton spectrum (DMSO-) of compound 1 d 6) Shows 8 amide protons d H 8.45 (1H, d, J = 8.2 Hz), 8.27 (1H, d, J= 7.4 Hz), 8.01 (1H, d, J = 7.4 Hz), 7.83 (1H, s), 7.77 (1H, d, J = 6.2 Hz), 7.70 (1H, m), 7.67 (1H, s), 7.52 (1H, s) and 8 α hydrogen proton d H 4.37 (1H, m), 4.30 (1H, m), 4.27 (1H, t, J = 6.7Hz), 4.23 (1H, m), 4.18 (1H, m), 4.16 (1H, m), 4.07 (1H, t, J = 7.1 Hz), 3.86 (1H, t, J = 6.4 Hz), indicating that compound 1 has 8 amino acid residues (Table 1). The carbon spectrum of compound 1 (DMSO- d 6) Displays signals with 8 carbonyl groups d C 172.5, 172.4, 172.4, 172.3, 171.2, 170.9, 170.9, 168.9 and 8 α carbon signal d C 57.8, 57.5, 57.4, 56.6, 54.6, 52.2, 51.7, 47.9. The above NMR data indicate that compound 1 is an octapeptide. Based on HSQC, HMBC, and... 1 H- 1 Comprehensive analysis of the H COSY spectrum revealed that the eight amino acids consisted of four isoleucines, one alanine, one lysine, one phenylalanine, and one leucine. The amino acid sequence was determined using HMBC and ROESY analyses. d H 7.52 (Ile) 1 -NH) / 4.23 (Leu) 8 - α -H), 7.77 (Ala) 2 -NH) / 4.07 (Ile) 1 - α -H), 8.27 (Ile) 3 -NH) / 4.27 (Ala) 2 - α -H), 8.01 (Ile) 4 -NH) / 4.18 (Ile) 3 - α -H), 7.67 (Lys 5 -NH) / 4.16(Ile)4 - α -H), 7.83 (Ile) 6 -NH) / 4.30(Lys 5 - α -H), 8.45 (Phe 7 -NH) / 3.86 (Ile) 6 - α -H), 7.70 (Leu) 8 -NH) / 4.37 (Phe 7 - α -H). Therefore, the amino acid linker sequence of compound 1 was identified as follows: N -Ile-Ala-Ile-Ile-Lys-Ile-Phe-Leu- C By comparing the NMR data with the references, compound 1 was identified as surugamide A.
[0016] The proton spectrum (DMSO-) of compound 2 d 6) Shows 8 amide protons d H 8.40 (1H, d, J = 8.5 Hz), 8.15 (1H, d, J = 8.0 Hz), 8.01 (2H, d, J = 7.3 Hz), 7.76 (2H, s), 7.68 (1H, d, J = 7.8 Hz), 7.64 (1H, s) and 8 α hydrogen proton d H 4.41 (1H, t, J = 3.5 Hz), 4.29 (2H, m), 4.26 (1H, m), 4.18 (1H, t, J = 8.2Hz), 4.11 (1H, t, J =7.2 Hz), 4.05 (1H, t, J = 7.5 Hz), 3.88 (1H, t, J = 6.3 Hz), indicating that compound 2 has 8 amino acid residues (Table 1). The carbon spectrum of compound 2 (DMSO- d 6) Displays signals with 8 carbonyl groups d C 172.4, 172.3, 172.1, 171.6, 170.8, 170.8, 170.5, 170.4 and 8 α carbon signal d C58.9, 57.7, 57.4, 57.1, 54.3, 52.0, 51.7, 48.1. The above NMR data indicate that compound 2 is an octapeptide. Comparison of the NMR data of compound 2 and compound 1 revealed that Ile in compound 1... 4 Replaced by Val, further comparison of the NMR data of compound 2 with the references identified compound 2 as surugamide B.
[0017] The proton spectrum (DMSO-) of compound 3 d 6) Shows 8 amide protons d H 8.42 (1H, d, J = 8.3 Hz), 8.26 (1H, d, J = 7.5 Hz), 7.98 (1H, d, J = 7.6 Hz), 7.81 (2H, d, J = 5.9 Hz), 7.70 (1H, d, J = 7.5 Hz), 7.65 (1H, s), 7.56 (1H, d, J = 6.1 Hz) and 8 α hydrogen proton d H 4.38 (1H, t, J = 3.5 Hz), 4.30 (1H, m), 4.27 (1H, t, J = 6.7 Hz), 4.23 (1H, m), 4.17 (1H, m), 4.14 (1H, m), 4.09 (1H, t, J = 7.3 Hz), 3.88 (1H, t, J = 6.3 Hz), indicating that compound 3 has 8 amino acid residues (Table 1). The carbon spectrum of compound 3 (DMSO- d 6) Displays signals with 8 carbonyl groups d C 172.4, 172.4, 172.3, 172.1, 171.1, 170.9, 170.9, 169.8 and 8 α carbon signal d C 58.7, 57.7, 57.2, 56.5, 54.6, 52.2, 51.7, 47.9. The above NMR data indicate that compound 3 is an octapeptide. Comparison of the NMR data of compound 3 and compound 1 revealed that Ile in compound 1... 3 Replaced by Val, further comparison of the NMR data of compound 3 with the references identified compound 3 as surugamide D.
[0018] The proton spectrum (DMSO-) of compound 4 d 6) Shows 8 amide protons d H 8.49 (1H, d, J = 8.2 Hz), 8.30 (1H, d, J = 7.3 Hz), 8.02 (1H, d, J = 7.2 Hz), 7.90 (1H, s), 7.72 (2H, t, J = 7.2 Hz), 7.63 (1H, s), 7.39 (1H, s) and 8 α hydrogen proton d H 4.37 (1H, t, J = 3.4 Hz), 4.32 (1H, m), 4.25 (1H, t, J = 6.7 Hz), 4.19 (2H, m), 4.13 (1H, m), 4.06 (1H, t, J = 7.1 Hz), 3.83 (1H, t, J = 6.3 Hz), indicating that compound 4 has 8 amino acid residues (Table 1). The carbon spectrum (DMSO-) of compound 4 d 6) Displays signals with 8 carbonyl groups d C 172.7, 172.6, 172.5, 172.4, 171.3, 170.9, 170.9, 169.8 and 8 α carbon signal d C 58.0, 57.9, 57.5, 56.7, 54.7, 52.4, 51.4, 47.9. The above NMR data indicate that compound 4 is an octapeptide. Comparison of the NMR data of compound 4 and compound 1 revealed that Ile in compound 1... 1 Replaced by Val, further comparison of the NMR data of compound 4 with the references identified compound 4 as surugamide E.
[0019] Example 1: Plant growth-promoting activity of the above-mentioned cyclic octapeptide compounds 1-4 First, the monomeric compounds 1-4 and the positive controls gibberellin and trans-zeatin were dissolved in methanol solution, and test solutions with concentrations of 0.1 μM, 0.01 μM, and 0.001 μM (methanol ratio 1%) were prepared using sterile water. Next, rice and corn seeds were sterilized with 75% alcohol for 5 min and washed three times with distilled water. The treated seeds were then placed in glass petri dishes containing 9 cm cellulose filter paper and incubated in the dark at 24°C for 48 h to allow germination. Two days after germination, uniformly sized seeds (N = 30) were selected and placed in glass petri dishes containing 9 cm cellulose filter paper, with 4 mL of the test solution added. Finally, under soilless conditions, the seeds were exposed to light for 16 h and then in darkness for 8 h. Two days later, the taproot length and stem length (cm) were measured.
[0020] The results of root growth promotion are shown in Table 1 and Figure 1 As shown, surugamides A and B, at a concentration of 0.1 μM, exhibited root growth-promoting activity in rice comparable to the positive controls gibberellin and trans-zeatin. The root growth-promoting results are shown in Table 2 and... Figure 2 As shown, surugamides A, B, D, and E all exhibited significant root-promoting activity in maize at concentrations of 0.1 μM and 0.01 μM, with surugamide A showing superior root-promoting effect compared to the positive control gibberellin at 0.1 μM. Observations revealed that surugamide A had a better root-promoting effect than the other three compounds, which may be related to the higher number of CH3 substituents compared to the other three compounds. When the concentration of surugamide A was 0.1 μM, the root length of rice plants reached 3.8 cm two days after high germination, an increase of 0.6 cm compared to the blank control group (Table 1); the root length of maize plants reached 4.7 cm two days after high germination, an increase of 1.4 cm compared to the blank control group (Table 2).
[0021] The results of promoting stem growth are shown in Table 3. Surugamides B, D, and E, at a concentration of 0.1 μM, all exhibited similar activities in promoting rice stem growth as the positive control trans-zeatin. The results of promoting stem growth are shown in Table 4. Surugamides A, D, and E, at a concentration of 0.1 μM, exhibited similar activities in promoting maize stem growth as the positive control gibberellin.
[0022] Table 1. Activity of compounds 1-4 in promoting rice root growth (root length cm)
[0023] Compared with the blank control.
[0024] Table 2. Activity of compounds 1-4 in promoting maize root growth (root length cm)
[0025] Compared with the blank control.
[0026] Table 3. Activity of compounds 1-4 in promoting rice stem growth (stem length cm)
[0027] Compared with the blank control.
[0028] Table 4. Activity of compounds 1-4 in promoting maize stem growth (stem length cm)
[0029] Compared with the blank control.
Claims
1. The application of a microbial-derived cyclic octapeptide compound, characterized in that: The application of microbial-derived cyclic octapeptide compounds, as shown in Formula I, as plant growth regulators.
2. The application of the microbial-derived cyclic octapeptide compound according to claim 1, characterized in that: The application of the microbial-derived cyclic octapeptide compound shown in Formula I as a plant root growth regulator.
3. The application of the microbial-derived cyclic octapeptide compound according to claim 1, characterized in that: The microbial-derived cyclic octapeptide compound shown in Formula I is used as a plant stem growth regulator.
4. The application of the microbial-derived cyclic octapeptide compound according to claim 1 or 2, characterized in that: The microbial-derived cyclic octapeptide compound represented by Formula I Formula I In the formula, R1, R2, and R3 can be the same or different and are selected from H or methyl.
5. A plant growth regulator, characterized in that: Plant growth regulators contain cyclic octapeptide compounds of microbial origin as shown in Formula I.