| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
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| Targets |
- AMPK, Nrf2, Sirt3 [1]
- HIV-1 Gp41 (IC50 = 1.8 μM for inhibiting HIV-1 entry) [2] |
|---|---|
| ln Vitro |
Trilobatin initially prevents oxidative damage to neuronal PC12 cells by controlling mitochondrial reactive oxygen species (mtROS), which is partially blindly driven by AMPK/Nrf2/Sirt3 signaling [1].
- Pretreatment with trilobatin (5, 10, 20 μM) significantly increased cell viability of H2O2-induced PC12 cells in a dose-dependent manner, as measured by CCK-8 assay. At 20 μM, the cell viability was notably higher compared to the H2O2-treated group [1] - Trilobatin (5, 10, 20 μM) reduced H2O2-induced mitochondrial ROS production in PC12 cells, as detected by MitoSOX Red staining. The levels of ROS were decreased in a dose-dependent manner [1] - Trilobatin (5, 10, 20 μM) upregulated the expression of p-AMPK, Nrf2, and Sirt3 in H2O2-induced PC12 cells, as shown by Western blot analysis. The protein levels increased with increasing concentrations of trilobatin [1] - Trilobatin inhibited HIV-1 entry into target cells in a dose-dependent manner, with an IC50 of 1.8 μM in the single-cycle HIV-1 entry assay using TZM-bl cells. It blocked the fusion of HIV-1 Env-expressing cells with target cells, as demonstrated by the cell-cell fusion assay [2] - Trilobatin (10 μM) bound to the HIV-1 Gp41 envelope, as indicated by the GST pull-down assay, and disrupted the formation of the Gp41 six-helix bundle (6-HB), which is critical for viral entry [2] |
| Enzyme Assay |
- For examining the effect on 6-HB formation: The Gp41 N-terminal heptad repeat (NHR) and C-terminal heptad repeat (CHR) peptides were incubated with different concentrations of trilobatin (0-100 μM) at 37°C for 1 h. The formation of 6-HB was monitored by measuring the turbidity at 350 nm. Trilobatin inhibited 6-HB formation with an IC50 of 8.5 μM [2]
- GST pull-down assay: GST-tagged Gp41 NHR protein was immobilized on glutathione sepharose beads and incubated with trilobatin (10 μM) at 4°C overnight. After washing, the bound proteins were eluted and analyzed by Western blot to detect the interaction between trilobatin and Gp41 NHR [2] |
| Cell Assay |
- Cell viability assay (PC12 cells): PC12 cells were seeded in 96-well plates and pretreated with trilobatin (5, 10, 20 μM) for 2 h, followed by exposure to H2O2 (200 μM) for 24 h. CCK-8 reagent was added, and the absorbance at 450 nm was measured to determine cell viability [1]
- Mitochondrial ROS detection: PC12 cells were pretreated with trilobatin (5, 10, 20 μM) for 2 h, then treated with H2O2 (200 μM) for 30 min. MitoSOX Red reagent was added, and the fluorescence intensity was measured using a microplate reader to assess mitochondrial ROS levels [1] - Western blot analysis (PC12 cells): PC12 cells were treated as above, lysed, and proteins were extracted. The levels of p-AMPK, AMPK, Nrf2, and Sirt3 were detected using specific antibodies, with β-actin as the internal control [1] - HIV-1 entry assay (TZM-bl cells): TZM-bl cells were seeded in 96-well plates and infected with HIV-1 pseudoviruses in the presence of trilobatin (0-10 μM). After 48 h, luciferase activity was measured to determine viral entry, and the IC50 was calculated [2] - Cell-cell fusion assay: 293T cells expressing HIV-1 Env (effector cells) and TZM-bl cells (target cells) were mixed in the presence of trilobatin (0-10 μM). After 4 h, luciferase activity was measured to evaluate fusion efficiency [2] |
| References |
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| Additional Infomation |
Trilobatin is an aryl beta-D-glucoside that is phloretin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It is isolated from the leaves of the Chinese sweet tea Lithocarpus polystachyus and exhibits significant anti-hyperglycemic, anti-oxidative and anti-inflammatory properties. It has a role as an anti-inflammatory agent, a sweetening agent, an antioxidant and a plant metabolite. It is an aryl beta-D-glucoside, a member of dihydrochalcones and a monosaccharide derivative. It is functionally related to a phloretin.
Trilobatin has been reported in Lithocarpus pachyphyllus, Vitis piasezkii, and other organisms with data available. - Trilobatin is a natural compound, and in the context of neuronal protection, it exerts its effects by regulating mitochondrial ROS homeostasis through the AMPK/Nrf2/Sirt3 signaling pathway, thereby protecting PC12 cells from H2O2-induced oxidative injury [1] - As an HIV-1 entry inhibitor, trilobatin targets the HIV-1 Gp41 envelope, inhibits 6-HB formation, and blocks viral entry into host cells, suggesting its potential as an anti-HIV-1 agent [2] |
| Molecular Formula |
C21H24O10
|
|---|---|
| Molecular Weight |
436.4093
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| Exact Mass |
436.136
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| Elemental Analysis |
C, 57.80; H, 5.54; O, 36.66
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| CAS # |
4192-90-9
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| PubChem CID |
6451798
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
787.9±60.0 °C at 760 mmHg
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| Melting Point |
163 °C
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| Flash Point |
277.1±26.4 °C
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| Vapour Pressure |
0.0±2.9 mmHg at 25°C
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| Index of Refraction |
1.686
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| LogP |
1.43
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
7
|
| Heavy Atom Count |
31
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| Complexity |
569
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C([H])=C(C(C(C([H])([H])C([H])([H])C2C([H])=C([H])C(=C([H])C=2[H])O[H])=O)=C(C=1[H])O[H])O[H]
|
| InChi Key |
GSTCPEBQYSOEHV-QNDFHXLGSA-N
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| InChi Code |
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
|
| Chemical Name |
1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
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| Synonyms |
Trilobatin; Trilobatin; 4192-90-9; p-Phlorizin; p-Phloridzin; phloretin-4'-O-glucoside; PRUNIN DIHYDROCHALCONE; 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one; 23298I791N; Phloretin-4-O-glucoside
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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 (~229.14 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.77 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 20.8 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: ≥ 2.08 mg/mL (4.77 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 20.8 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: ≥ 2.08 mg/mL (4.77 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 | 2.2914 mL | 11.4571 mL | 22.9142 mL | |
| 5 mM | 0.4583 mL | 2.2914 mL | 4.5828 mL | |
| 10 mM | 0.2291 mL | 1.1457 mL | 2.2914 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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