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Referencia número: HY-N6610

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Protoanemonin

Protoanemonin is a natural unsaturated γ-lactone small molecule derived from plants of the Ranunculaceae family, possessing various activities such as plant growth regulation, antibacterial, and antifungal effects. Protoanemonin is a quorum sensing inhibitor that inhibits Pseudomonas aeruginosa quorum sensing, downregulates virulence factor expression, and activates the iron starvation response pathway. Protoanemonin possesses broad-spectrum antibacterial and antifungal activities, and also has antimutagenic activity. Protoanemonin exhibits bidirectional plant growth regulatory effects, promoting plant tissue elongation at low concentrations and inhibiting plant tissue elongation at high concentrations. Protoanemonin can be used in research related to bacterial quorum sensing, microbial metabolism, antibacterial and antifungal activity, antimutagenesis, and plant growth regulation.

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No. CAS: 108-28-1
Fòrmula: C₅H₄O₂
Peso molecular:96.08

Almacenamiento:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (284 KB)

Protoanemonin Chemical Structure

No. CAS: 108-28-1

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Actividad biológica
- Descripciòn
- In Vitro
Chemical Information
Pureza y Documentación
Referencias
Calculators
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Classifications
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Actividad biológica

Descripciòn

In Vitro

OthersBacterial InfectionFungal Infection

Others

Protoanemonin inhibits quorum sensing-dependent virulence factor gene and protein expression in Pseudomonas aeruginosa PAO1 and activates the iron starvation response pathway^[1].
Protoanemonin (20-160 μg/plate) reduces the mutation frequency induced by ultraviolet light and MNNG (HY-128612) in Escherichia coli B/r WP2 trp cells, with UV mutation AD₅₀ = 30 μg/plate and MNNG mutation AD₅₀ = 47 μg/plate^[2].
Protoanemonin (0‑200 μg/3 mL soft agar) exhibits almost no cytotoxicity toward ultraviolet- and MNNG-induced Escherichia coli B/r WP2 Trp⁺ mutant clones, with a cell survival rate higher than 91.2% at a concentration of 200 μg/plate^[2].
Protoanemonin (4×10^-6-1×10^-4 M; 48 h) inhibits the elongation of pea stem and oat coleoptile segments, while at low concentrations it produces a growth-promoting effect^[3].
Protoanemonin can be generated from 4-chlorocatechol catalyzed by enzymes of the 3-oxoadipate pathway through muconate cycloisomerase-mediated dechlorination-decarboxylation conversion^[6].

Bacterial Infection

Protoanemonin exhibits broad-spectrum growth inhibitory activity against multiple bacterial strains, with MICs ranging from 8 μg/mL to 62.5 μg/mL for aerobic bacterial strains and from 15.625-125 μg/mL for anaerobic bacterial strains; moreover, when combined with different antibiotics, 20 of 22 tested combinations produce partial synergistic effects against aerobic bacteria (0.5 < FIC ≤ 0.75)^[4].

Fungal Infection

Protoanemonin inhibits the growth of multiple dermatophyte and yeast fungal strains, with MIC ranging from 2.0 × 10^‑4 M to 7.5 × 10^‑4 M and MLC ranging from 3.8 × 10^‑4 M to > 1.0 × 10^‑3 M; it loses antifungal activity after reacting with L-cysteine^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

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Chemical Information

No. CAS 108-28-1
Peso molecular 96.08
Fòrmula C₅H₄O₂
SMILES

O=C1OC(C=C1)=C
Structure Classification
- Others
Initial Source
Envío

Room temperature in continental US; may vary elsewhere.
Almacenamiento

Please store the product under the recommended conditions in the Certificate of Analysis.

Pureza y Documentación

Select Batch:

Pureza: 99.98%

Assay: 99.98%

ee.: 99.98%

Ficha de datos (284 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instrucciones de manejo (2659 KB)

Referencias

[1]. Bobadilla Fazzini RA, et al. Protoanemonin: a natural quorum sensing inhibitor that selectively activates iron starvation response. Environmental microbiology. 2013 Jan;15(1):111-20.

[2]. Minakata H, et al. Protoanemonin, an antimutagen isolated from plants. Mutation research. 1983 Mar;116(3-4):317-22.

[3]. Thimann KV. Inhibition of Plant Growth by Protoanemonin and Coumarin, and Its Prevention by Bal. Proc Natl Acad Sci U S A. 1949 Jun;35(6):272-6.

[4]. Didry N. Microbiological properties of protoanemonin isolated from Ranunculus bulbosus. Phytotherapy Research. 1993;7(1):21-24.

[5]. Mares D, et al. Antimicrobial activity of protoanemonin, a lactone from ranunculaceous plants. Mycopathologia. 1987 Jun;98(3):133-40.

[6]. Blasco R, et al. From xenobiotic to antibiotic, formation of protoanemonin from 4-chlorocatechol by enzymes of the 3-oxoadipate pathway. The Journal of biological chemistry. 1995 Dec 08;270(49):29229-35.

Calculators

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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