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Purity: ≥98%
Violanthin is a naturally occuring flavanoid 8-c-glycoside acting as a potent acetylcholinesterase (AChE) inhibitor with IC50 of 79.80 μM. It can be isolated from the aerial parts of Piper bavinum and has high antioxidant and antibacterial activities.
| Targets |
Natural product/flavone; acetylcholinesterase (AChE)
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|---|---|
| ln Vitro |
A new alkenylphenol, bavinol A (1), together with six known compounds (2-7) were isolated from the aerial parts of Piper bavinum (Piperaceae). The chemical structures of these compounds were determined by spectroscopic analyses including 2D NMR spectroscopy. The anti-Alzheimer effects of compounds 1-7 were evaluated from acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity assays. Bavinol A (1), ampelopsin (3), and violanthin (4) exhibited AChE inhibitory activities with IC50 values of 29.80, 59.47 and 79.80 μM. Compound 1 also showed the most potent BChE inhibitory activity with an IC50 value of 19.25 μM[1].
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| Enzyme Assay |
In vitro AChE inhibitory activity assay[1]
The inhibitory activities of AChE and BChE were measured using the spectrophotometric method developed by Ellman with a slight modification (Ellman et al. 1961). Essentially, ACh and BCh were used as substrates to detect the inhibitions of AChE and BChE, respectively. The reaction mixture contained: 140 μL of sodium phosphate buffer (pH 8.0); 20 μL of tested sample solution [final concentration (f.c.) 100 μM for either compound]; and 20 μL of AChE or BChE solution, which were mixed and incubated for 15 min at room temperature. All tested samples and the positive control (berberine) were dissolved in 10 % analytical grade dimethyl sulfoxide (DMSO). Reactions were started by adding 10 μL of 5,5′-dithio-bis-(2-nitrobenzoic acid) (DTNB) and 10 μL of ACh or BCh. The hydrolysis of ACh or BCh was monitored by following the formation of the yellow 5-thio-2-nitrobenzoate anion (formed by the reaction between DTNB and thiocholine, released by the enzymatic hydrolysis of ACh or BCh) at 412 nm for 15 min. All reactions were performed in triplicate and recorded in 96-well microplates using a VERSA max ELISA Microplate Reader. Percent inhibition was calculated using (1–S/E) × 100, where E and S are enzyme activities with or without the tested sample, respectively. The ChEs inhibitory activity of each sample was expressed as IC50 values (μM, defined as the concentration required inhibiting the hydrolysis of substrate by ACh or BCh by 50 %, as calculated using log-dose inhibition curves). |
| Cell Assay |
Violanthin is a flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5, 7 and 4', a beta-D-glucopyranosyl residue at position 6 and a 6-deoxy-alpha-L-mannopyranosyl residue at position 8. It has a role as a plant metabolite and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is a flavone C-glycoside and a trihydroxyflavone. It is functionally related to a flavone.
Violanthin has been reported in Adenia mannii, Angiopteris hypoleuca, and other organisms with data available.
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| References | |
| Additional Infomation |
Violanthin is a flavone C-glycoside that is flavone substituted by hydroxy groups at positions 5, 7 and 4', a beta-D-glucopyranosyl residue at position 6 and a 6-deoxy-alpha-L-mannopyranosyl residue at position 8. It has a role as a plant metabolite and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is a flavone C-glycoside and a trihydroxyflavone. It is functionally related to a flavone.
Violanthin has been reported in Adenia mannii, Angiopteris hypoleuca, and other organisms with data available. |
| Molecular Formula |
C₂₇H₃₀O₁₄
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|---|---|
| Molecular Weight |
578.52
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| Exact Mass |
578.164
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| CAS # |
40581-17-7
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| PubChem CID |
442665
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| Appearance |
White to yellow solid powder
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| Source |
Adenia mannii, Angiopteris hypoleuca; stems of Dendrobium officinale
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| LogP |
-1.8
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| Hydrogen Bond Donor Count |
10
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
41
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| Complexity |
970
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| Defined Atom Stereocenter Count |
10
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| SMILES |
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)C2=C3C(=C(C(=C2O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C(=O)C=C(O3)C5=CC=C(C=C5)O)O)O)O
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| InChi Key |
MVOUGOXRXQDXDC-RSPRXDBDSA-N
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| InChi Code |
InChI=1S/C27H30O14/c1-8-17(31)21(35)23(37)27(39-8)16-20(34)15(26-24(38)22(36)18(32)13(7-28)41-26)19(33)14-11(30)6-12(40-25(14)16)9-2-4-10(29)5-3-9/h2-6,8,13,17-18,21-24,26-29,31-38H,7H2,1H3/t8-,13+,17-,18+,21+,22-,23+,24+,26-,27-/m0/s1
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| Chemical Name |
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]chromen-4-one
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| Synonyms |
C10196; 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]chromen-4-one; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-8-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy -6-(hydroxymethyl)oxan-2-yl]-8-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-me thyl-oxan-2-yl]chromen-4-one; AC1L9D6N; SureCN993603;
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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: 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~172.85 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.32 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 25.0 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: 2.5 mg/mL (4.32 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 | 1.7285 mL | 8.6427 mL | 17.2855 mL | |
| 5 mM | 0.3457 mL | 1.7285 mL | 3.4571 mL | |
| 10 mM | 0.1729 mL | 0.8643 mL | 1.7285 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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