| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
|
||
| 5mg | |||
| Other Sizes |
| Targets |
Vomifoliol targets stomatal guard cells in plants, inducing stomatal closure through a mechanism similar to abscisic acid. [1]
In enzymatic assays, vomifoliol inhibits acetylcholinesterase (AChE) with an IC50 of 96.64 ± 0.09 μg/mL. [2] It also exhibits activity against Leishmania donovani promastigotes with an IC50 of 302.80 ± 0.33 μg/mL. [2] |
|---|---|
| ln Vitro |
Vomifoliol induces stomatal closure in epidermal strips of Eichhornia crassipes. In a bioassay using phosphate buffer (pH 5.7) with illumination (1800 lx) and CO₂-free aeration, vomifoliol at concentrations ranging from 10⁻⁴ to 10⁻¹¹ M caused a log-linear reduction in stomatal aperture. The regression line for vomifoliol (y = 0.3024x + 2.4645) showed no significant difference in slope compared to abscisic acid (p = 0.05), indicating equal activity at identical concentrations. [1]
Vomifoliol exhibits moderate acetylcholinesterase (AChE) inhibitory activity with an IC50 of 96.64 ± 0.09 μg/mL. [2] Vomifoliol also demonstrates moderate antileishmanial activity against Leishmania donovani promastigotes with an IC50 of 302.80 ± 0.33 μg/mL, as determined by MTT colorimetric assay. [2] |
| Enzyme Assay |
Acetylcholinesterase (AChE) inhibition assay (Ellman method) : The assay was performed in a 96-well microplate. Each well contained 130 μL of 0.1 mM sodium phosphate buffer (pH 8.0), 20 μL of DTNB (5,5'-dithio-bis(2-nitrobenzoic acid)), 20 μL of test solution (vomifoliol), and 20 μL of AChE solution. After 15 min incubation at 25°C, 10 μL of acetylthiocholine iodide was added to initiate the reaction. The hydrolysis of acetylthiocholine was measured by monitoring the production of the 5-thio-2-nitrobenzoate anion at 412 nm using a microplate reader. Percentage inhibition was calculated as [(E - S)/E] × 100, where E is enzyme activity without test sample and S is enzyme activity with test sample. Galanthamine (IC50 = 0.77 ± 0.09 μg/mL) was used as a positive control. Vomifoliol showed an IC50 of 96.64 ± 0.09 μg/mL. [2]
|
| Cell Assay |
Antileishmanial assay (MTT colorimetric method) : Leishmania donovani promastigotes (strain MHOM/IN/1983/AG83) at 5 × 10⁵ cells/mL were treated with test samples (vomifoliol) at various concentrations and incubated at 22 ± 2°C for 72 hours. After incubation, cells were harvested, resuspended in PBS containing MTT (0.3 mg/mL), and incubated further. The resulting purple formazan crystals were dissolved in DMSO, and optical density was measured at 570 nm using an ELISA reader. The percentage of growth inhibition was calculated as [(OD of untreated control - OD of treated set)/OD of untreated control] × 100. Amphotericin B (IC50 = 0.37 ± 0.10 μg/mL) was used as a positive control. Vomifoliol showed an IC50 of 302.80 ± 0.33 μg/mL. [2]
|
| References | |
| Additional Infomation |
Chemical structure: Vomifoliol (systematic name: (3S,5R,6S,7E)-5,6-dihydroxy-3-methyl-7-(2-oxopropyl)-1,2-benzenediol? Not exactly). The stereochemistry of vomifoliol was defined through its identification as blumenol A. Its β-glucoside, roseoside, has also been isolated from Vinca rosea. [1]
Plant source: Vomifoliol has been isolated from Rauvolfia vomitoria (Apocynaceae), Croton species (Euphorbiaceae), Palicourea alpina (Rubiaceae), and Podocarpus blumei (Podocarpaceae), as well as from Canarium patentinervium Miq. (Burseraceae). [1][2] Mechanism of action (plant physiology) : Vomifoliol causes stomatal closure in a manner similar to abscisic acid, although its exact mechanism and whether it is converted to ABA in planta require further investigation. In vitro conversion of vomifoliol to ABA has been achieved. [1] (6S,9R)-Vomitoxin is a (6S)-vomitoxin with an R configuration at the 9-position hydroxyl group. It is both a phytotoxin and a metabolite. It is the enantiomer of (6R,9S)-vomitoxin. Vomitoxin has been reported in Otanthus maritimus, Euchresta formosana, and other organisms with relevant data. |
| Molecular Formula |
C13H20O3
|
|---|---|
| Molecular Weight |
224.30
|
| Exact Mass |
224.141
|
| CAS # |
23526-45-6
|
| PubChem CID |
5280462
|
| Appearance |
White to off-white solid powder
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
362.3±42.0 °C at 760 mmHg
|
| Flash Point |
187.1±24.4 °C
|
| Vapour Pressure |
0.0±1.8 mmHg at 25°C
|
| Index of Refraction |
1.567
|
| LogP |
1.05
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
16
|
| Complexity |
352
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
CC1=CC(=O)CC([C@]1(/C=C/[C@@H](C)O)O)(C)C
|
| InChi Key |
KPQMCAKZRXOZLB-KOIHBYQTSA-N
|
| InChi Code |
InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1
|
| Chemical Name |
(4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one
|
| Synonyms |
Vomifoliol; 23526-45-6; (6S,9R)-vomifoliol; (6S,9R)-6-hydroxy-3-oxo-alpha-ionol; (+)-Vomifoliol;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 50 mg/mL (222.92 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (5.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 12.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (5.57 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 12.5 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. View More
Solubility in Formulation 3: ≥ 1.25 mg/mL (5.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4583 mL | 22.2916 mL | 44.5831 mL | |
| 5 mM | 0.8917 mL | 4.4583 mL | 8.9166 mL | |
| 10 mM | 0.4458 mL | 2.2292 mL | 4.4583 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
