Cyclo(L-Pro-L-Val)
(Synonyms: 环(L-脯-L-缬)二肽) 目录号 : GC45416
A diketopiperazine
Cas No.:2854-40-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cyclo(L-Pro-L-Val) is a diketopiperazine that has been found in the marine sponge T. ignis, the bacterium B. pumilus, and the fungus A. fumigatus, among others.1,2,3 It is active against the bacteria S. aureus and B. subtilis (MICs = 16.3 and 18.2 μg/ml, respectively) but not E. coli (MIC = >20 μg/ml).3 Cyclo(L-Pro-L-Val) inhibits activation of a LuxR-dependent E. coli biosensor by the quorum-sensing molecule 3-oxo-hexanoyl-homoserine lactone (IC50 = 0.4 mM) and activates violacein pigment production in the LuxR-dependent C. violaceum acyl homoserine lactone reporter strain CV026.4 However, it does not activate or inhibit lacZ-based reporter fusions in S. liquefaciens or A. tumefaciens.
References
1. Schmitz, F.J., Vanderah, D.J., Hollenbeak, K.H., et al. Metabolites from the marine sponge Tedania ignis. A new atisanediol and several known diketopiperazines. J. Org. Chem. 48(22), 3941-3945 (1983).
2. Brack, C., Mikolasch, A., and Schauer, F. 2,5-Diketopiperazines produced by Bacillus pumilus during bacteriolysis of Arthrobacter citreus. Mar. Biotechnol. (NY) 16(4), 385-395 (2014).
3. El-Gendy, B.E.-D.M., and Rateb, M.E. Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification. Bioorg. Med. Chem. Lett. 25(16), 3125-3128 (2015).
4. Holden, M.T.G., Chhabra, S.R., de Nys, R., et al. Quorum-sensing cross talk: Isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other gram-negative bacteria. Mol. Microbiol. 33(6), 1254-1266 (1999).
| Cas No. | 2854-40-2 | SDF | |
| 别名 | 环(L-脯-L-缬)二肽 | ||
| Canonical SMILES | O=C([C@H](C(C)C)N1)N2[C@](CCC2)([H])C1=O | ||
| 分子式 | C10H16N2O2 | 分子量 | 196.2 |
| 溶解度 | PBS (pH 7.2): 2mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.0968 mL | 25.4842 mL | 50.9684 mL |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Cyclic peptides. XIX. Synthesis, conformation, and biological activity of Cyclo(-Pro-Val-Pro-Val-) with L-L-L-L and L-D-L-D sequences
Int J Pept Protein Res 1985 May;25(5):475-80.PMID:4019028doi
Cyclo(-L-Pro-L-Val-L-Pro-L-Val-) (1L) and Cyclo(-L-Pro-D-Val-L-Pro-D-Val-) (1D) were synthesized by the conventional method for peptide synthesis. Conformations of 1L and 1D in solution were studied. Compound 1L has a cis-trans-cis-trans backbone conformation with C2 symmetry in CDCl3. This conformation is slightly different from that in crystalline state and in DMSO-d6 solution. Compound 1D has a cis-trans-cis-trans conformation in DMSO-d6 and an all-trans conformation in trifluoroethanol-d3. Compound 1L retarded stem-growth of rice seedlings and, in contrast, compound 1D promoted root-growth of rice seedlings.
Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians
Nat Prod Res 2021 Dec;35(23):4969-4977.PMID:32352330DOI:10.1080/14786419.2020.1756803.
Inhibitory activity of the biocontrol bacterial strain Lysobacter capsici AZ78 is related to the production of cyclo(l-Pro-l-Tyr), a 2,5-diketopiperazine with in vitro and in vivo toxic activity against Phytophthora infestans and Plasmopara viticola. Further investigation of culture filtrate organic extracts showed its ability to produce other 2,5-diketopiperazines. They were isolated and identified by spectroscopic (1H NMR and ESIMS) and physic (specific optical rotation) methods as Cyclo(L-Pro-L-Val), cyclo(d-Pro-d-Phe), cyclo(l-Pro-l-Leu), and cyclo(d-Pro-l-Tyr). When tested against the phytopathogenic Gram-positive bacterium Rhodococcus fascians LMG 3605, Cyclo(L-Pro-L-Val) showed a toxic activity similar to chloramphenicol at a comparable concentration. Overall, these data suggest that 2,5-diketopiperazines represent a class of metabolites characterizing the metabolome of L. capsici AZ78. Furthermore, the toxic activity showed by Cyclo(L-Pro-L-Val) against R. fascians LMG 3605 broaden the spectrum activity of 2,5-diketopiperazines against phytopathogenic microorganisms enforcing their potential development as biopesticides.[Figure: see text].
Antibacterial Activity of Two Metabolites Isolated From Endophytic Bacteria Bacillus velezensis Ea73 in Ageratina adenophora
Front Microbiol 2022 May 6;13:860009.PMID:35602058DOI:10.3389/fmicb.2022.860009.
Ageratina adenophora, as an invasive and poisonous weed, seriously affects the ecological diversity and development of animal husbandry. Weed management practitioners have reported that it is very difficult to control A. adenophora invasion. In recent years, many researchers have focused on harnessing the endophytes of the plant as a useful resource for the development of pharmacological products for human and animal use. This study was performed to identify endophytes with antibacterial properties from A. adenophora. Agar well diffusion method and 16S rRNA gene sequencing technique were used to screen and identify endophytes with antibacterial activity. The response surface methodology and prep- high-performance liquid chromatography were used to determine the optimizing fermentation conditions and isolate secondary metabolites, respectively. UV-visible spectroscopy, infrared spectroscopy, nuclear magnetic resonance, and high-resolution mass spectrum were used to determine the structures of the isolated metabolites. From the experiment, we isolated a strain of Bacillus velezensis Ea73 (GenBank no. MZ540895) with broad-spectrum antibacterial activity. We also observed that the zone of inhibition of B. velezensis Ea73 against Staphylococcus aureus was the largest when fermentation broth contained 6.55 g/L yeast extract, 6.61 g/L peptone, 20.00 g/L NaCl at broth conditions of 7.95 pH, 51.04 h harvest time, and a temperature of 27.97°C. Two antibacterial peptides, Cyclo (L-Pro-L-Val) and Cyclo (L-Leu-L-Pro), were successfully extracted from B. velezensis Ea73. These two peptides exhibited mild inhibition against S. aureus and Escherichia coli. Therefore, we isolated B. velezensis Ea73 with antibacterial activity from A. adenophora. Hence, its metabolites, Cyclo (L-Pro-L-Val) and Cyclo (L-Leu-L-Pro), could further be developed as a substitute for human and animal antibiotics.
Bioactive Phytochemicals from Mulberry: Potential Anti-Inflammatory Effects in Lipopolysaccharide-Stimulated RAW 264.7 Macrophages
Int J Mol Sci 2021 Jul 29;22(15):8120.PMID:34360887DOI:10.3390/ijms22158120.
The fruits of the mulberry tree (Morus alba L.), known as white mulberry, have been consumed in various forms, including tea, beverages, and desserts, worldwide. As part of an ongoing study to discover bioactive compounds from M. alba fruits, the anti-inflammatory effect of compounds from M. alba were evaluated in lipopolysaccharide (LPS)-stimulated mouse RAW 264.7 macrophages. Phytochemical analysis of the ethanol extract of the M. alba fruits led to the isolation of 22 compounds. Among the isolated compounds, to the best of our knowledge, compounds 1, 3, 5, 7, 11, 12, and 14-22 were identified from M. alba fruits for the first time in this study. Inhibitory effects of 22 compounds on the production of the nitric oxide (NO) known as a proinflammatory mediator in LPS-stimulated RAW 264.7 macrophages were evaluated using NO assays. Western blot analysis was performed to evaluate the anti-inflammatory effects of Cyclo(L-Pro-L-Val) (5). We evaluated whether the anti-inflammatory effects of Cyclo(L-Pro-L-Val) (5) following LPS stimulation in RAW 264.7 macrophages occurred because of phosphorylation of IκB kinase alpha (IKKα), IκB kinase beta (IKKβ), inhibitor of kappa B alpha (IκBα), nuclear factor kappa B (NF-κB) and activations of inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX-2). Cyclo(L-Pro-L-Val) (5) significantly suppressed phosphorylations of IKKα, IKKβ, IκBα, and NF-κB and activations of iNOS and COX-2 in a concentration-dependent manner. Taken together, these results indicate that Cyclo(L-Pro-L-Val) (5) can be considered a potential therapeutic agent for the treatment of inflammation-associated disorders.
Bacterial Lipodepsipeptides and Some of Their Derivatives and Cyclic Dipeptides as Potential Agents for Biocontrol of Pathogenic Bacteria and Fungi of Agrarian Plants
J Agric Food Chem 2022 Apr 20;70(15):4591-4598.PMID:35395154DOI:10.1021/acs.jafc.1c08139.
Biotic stresses (fungi, bacteria, insects, weeds, etc.) are some of the most important causes of the decrease in the quality and quantity of crops that could become an emergency due to a noteworthy increase in the world population. Thus, to overcome these problems, massive use of chemical pesticides has been carried out with heavy consequences for environmental pollution and food safety. An eco-friendly alternative can be using natural compound-based biopesticides with high efficacy and selectivity. Some bacterial lipodepsipeptides (tolaasins I, II, A, D, and E and WLIP together with hexacetyl- and tetrahydro-tolaasin I and WLIP methyl ester) and cyclic dipeptides (cyclo(l-Pro-l-Tyr), cyclo(d-Pro-l-Tyr), Cyclo(L-Pro-L-Val), and cyclo(l-Pro-l-Leu)) were assayed against several pathogenic bacteria and fungi of important agrarian plants. Lipodepsipeptides showed strong growth inhibition of all microorganisms tested in the range of 0.1-0.8 μg/mL, while cyclodipeptides, despite preserving this ability, showed a noteworthily reduced antimicrobial activity being active only in the range of 15-900 μg/mL. Among the lipodepsipeptides and cyclic dipeptides assayed, tolaasin d and cyclo(l-Pro-l-Tyr) (also named maculosin-1) appeared to be the most toxic compounds. Some structure-activity relationships of lipodepsipeptides were also discussed along with their practical application as biopesticides in agriculture.