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| 10mg |
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| Targets |
Maculosin targets quorum-sensing systems in Pseudomonas aeruginosa, suppressing both the las and rhl systems. It also acts as a host-specific phytotoxin against spotted knapweed (Centaurea maculosa). The compound exhibits antioxidant activity through DPPH radical scavenging with an IC50 of 2.16 μg/mL, which is 2.2 times more potent than BHA (4.8 μg/mL). As a cyclic dipeptide, it may also interact with bacterial signaling pathways and plant receptors, though specific molecular targets are not fully characterized.
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| ln Vitro |
In vitro, Maculosin exhibits potent antioxidant activity with a DPPH radical scavenging IC50 of 2.16 μg/mL. It acts as a host-specific phytotoxin, inducing the formation of weeping necrotic lesions in leaves of spotted knapweed at a concentration of 10 μM. The compound shows antibacterial activity with a minimum inhibitory concentration (MIC) of 31.25 μg/mL against the plant pathogen Xanthomonas axonopodis. It suppresses both las and rhl quorum-sensing systems in P. aeruginosa.
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| ln Vivo |
In vivo, Maculosin is a host-specific phytotoxin that induces necrotic lesions in spotted knapweed leaves. As a secondary metabolite of fungi and bacteria, it plays a role in microbial ecology and plant-pathogen interactions. The compound has been studied for its potential as a bioherbicide against spotted knapweed, an invasive weed species. However, specific in vivo efficacy data in animal models are not extensively reported.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Maculosin are not well-established, as it is a natural product with multiple activities. For antioxidant activity, DPPH radical scavenging assays are performed by incubating the compound (typically 1-100 μg/mL) with DPPH solution (0.1 mM in methanol) at room temperature for 30 minutes, and absorbance is measured at 517 nm. For antibacterial assays, the compound is tested against bacterial cultures using broth microdilution methods to determine MIC values. Quorum-sensing inhibition is assessed using reporter strains.
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| Cell Assay |
In vitro cellular assays for Maculosin use bacterial cultures such as Pseudomonas aeruginosa or Xanthomonas axonopodis. Bacteria are grown in appropriate media to mid-log phase and treated with various concentrations of the compound (typically 1-100 μg/mL) for 16-24 hours. Bacterial growth is monitored by OD600 measurement. Quorum-sensing inhibition is assessed using reporter strains with luminescent or colorimetric readouts. Antibacterial activity is quantified by MIC determination. Antioxidant activity can be assessed in cell-free systems using DPPH or ABTS assays.
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| Animal Protocol |
In vivo animal studies with Maculosin are not extensively reported, as the compound is primarily studied as a phytotoxin and antibacterial agent. In plant models, spotted knapweed leaves are treated with the compound at 10 μM, and lesion formation is observed. In animal models, the compound could potentially be studied for its antibacterial or anti-quorum-sensing effects, but specific protocols are not detailed in the available literature.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Maculosin are not extensively reported. As a cyclic dipeptide with a molecular weight of 260.29, it is expected to have moderate lipophilicity and oral bioavailability. The compound is soluble in DMSO and other organic solvents. Specific PK parameters such as half-life, volume of distribution, and clearance are not detailed. The compound is a secondary metabolite and is likely metabolized by peptidases.
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| Toxicity/Toxicokinetics |
The toxicity profile of Maculosin is not extensively reported. As a naturally occurring compound, it is expected to have moderate toxicity. The compound is for research use only and not for human therapeutic use. Standard toxicity studies would include cytotoxicity assays in mammalian cell lines and acute toxicity in rodents. No specific genotoxicity or carcinogenicity data are reported.
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| References |
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| Additional Infomation |
Maculosin is a homocyclic peptide, a dipeptide composed of L-proline and L-tyrosine linked by a peptide bond. It is a metabolite. Maculosin is a dipeptide, homocyclic peptide, pyrrolopyrazine compound, and also belongs to the phenolic class of compounds. Functionally, it is related to L-proline and L-tyrosine. Maculosin has been reported to be detected in Aspergillus versicolor, Leptooxyphium, and several other organisms with relevant data.
Maculosin (CAS 4549-02-4) is a naturally occurring cyclic dipeptide with multiple biological activities including phytotoxicity, antibacterial effects, antioxidant activity, and quorum-sensing modulation. It has a molecular formula of C14H16N2O3 and a molecular weight of 260.29. The compound is used in research on quorum sensing, phytotoxicity, and antioxidant mechanisms. It is available for research purposes only and is not approved for clinical use. |
| Molecular Formula |
C14H16N2O3
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|---|---|
| Molecular Weight |
260.28844
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| Exact Mass |
260.116
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| CAS # |
4549-02-4
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| PubChem CID |
119404
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| Appearance |
White to off-white solid powder
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| Density |
1.36g/cm3
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| Boiling Point |
581.4ºC at 760mmHg
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| Melting Point |
156-159 °C
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| Flash Point |
305.4ºC
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| Index of Refraction |
1.644
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| LogP |
0.69
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
19
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| Complexity |
377
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CC=C(C=C3)O
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| InChi Key |
LSGOTAXPWMCUCK-RYUDHWBXSA-N
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| InChi Code |
InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
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| Chemical Name |
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~384.19 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8419 mL | 19.2093 mL | 38.4187 mL | |
| 5 mM | 0.7684 mL | 3.8419 mL | 7.6837 mL | |
| 10 mM | 0.3842 mL | 1.9209 mL | 3.8419 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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