Trilobatin

CAS# 4192-90-9

Trilobatin

Catalog No. BCN5479----Order now to get a substantial discount!

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Quality Control of Trilobatin

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Chemical structure

Trilobatin

3D structure

Chemical Properties of Trilobatin

Cas No. 4192-90-9 SDF Download SDF
PubChem ID 6451798 Appearance White powder
Formula C21H24O10 M.Wt 436.4
Type of Compound Chalcones Storage Desiccate at -20°C
Synonyms Phloretin 4'-glucoside; p-Phloridzin; p-Phlorizin; Prunin dihydrochalcone
Solubility Soluble in ethan
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
SMILES C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)OC3C(C(C(C(O3)CO)O)O)O)O)O
Standard InChIKey GSTCPEBQYSOEHV-QNDFHXLGSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Trilobatin

1 Malus sp.

Biological Activity of Trilobatin

DescriptionTrilobatin has anti-oxidant, and anti-inflammatory effects, it can increase superoxide dismutase (SOD) activity, and it potentially inhibits the lipopolysaccharide (LPS)-induced inflammatory response by suppressing the NF-κB signaling pathway. Trilobatin shows a strong inhibitory activity against α-glucosidase and a moderate inhibitory activity against α-amylase for management of postprandial hyperglycemia with less side effect.
TargetsTNF-α | IL Receptor | IkB | NF-kB | p65 | IKK | SOD
In vitro

Trilobatin attenuates the LPS-mediated inflammatory response by suppressing the NF-κB signaling pathway.[Pubmed: 25053100 ]

Food Chem. 2015 Jan 1;166:609-15.

We investigated the anti-inflammatory effect of Trilobatin, the flavonoid isolated from the leaves of Lithocarpus polystachyus Rehd, as well as the underlying molecular mechanisms.
METHODS AND RESULTS:
Treatment with Trilobatin (0.005-5 μM) dose-dependently inhibited the lipopolysaccharide (LPS)-induced mRNA expression and secretion of pro-inflammatory cytokines, including tumor necrosis factor α (TNFα), interleukin-1β (IL-1β) and interleukin-6 (IL-6), in RAW 264.7 macrophages. However, no further inhibition was detected when the concentration of Trilobatin was increased to 50 μM. Western blot analysis confirmed that the mechanism of the anti-inflammatory effect was correlated with the inhibition of LPS-induced inhibitor of nuclear factor-kappa B α (IκBα) degradation and nuclear factor-kappa B (NF-κB) p65 phosphorylation. In addition, Trilobatin also showed a significant inhibition of LPS-induced TNFα and IL-6 at both the mRNA and protein levels in a mouse model.
CONCLUSIONS:
Our results suggest that Trilobatin potentially inhibits the LPS-induced inflammatory response by suppressing the NF-κB signaling pathway.

Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus.[Pubmed: 15813365]

Z Naturforsch C. 2004 Jul-Aug;59(7-8):481-4.

In vitro antioxidant activities of three sweet dihydrochalcone glucosides from the leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae), Trilobatin 2"-acetate (1), phloridzin (2) and Trilobatin (3), were investigated.
METHODS AND RESULTS:
The IC50 (50% inhibitory concentration) values for compounds 1-3 of lipid peroxidation in rat liver homogenate were 261, 28, 88 microM, respectively. Compounds 1-3 increased superoxide dismutase (SOD) activity with EC50 (50% effective concentration) values of 575, 167, 128 microM, and glutathione peroxidase (GSH-Px) activity with EC50 values of 717, 347, 129 microM, respectively, and showed only weak DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity.

Protocol of Trilobatin

Kinase Assay

Inhibitory potential of trilobatin from Lithocarpus polystachyus Rehd against α-glucosidase and α-amylase linked to type 2 diabetes.[Reference: WebLink]

Food Chemistry, 2012, 130(2):261-266.

The chemical structure of the sweet compound from Lithocarpus polystachyus Rehd was identified as Trilobatin on the basis of HPLC, EIS-MS and NMR analyses.
METHODS AND RESULTS:
The inhibitory activities of Trilobatin against α-glucosidase and α-amylase were evaluated, and the inhibition mechanism was analysed with Lineweaver–Burk plots. Also the antioxidant activity evaluation of Trilobatin was conducted by DPPH radical scavenging assay. Comparing with acarbose, Trilobatin showed a strong inhibitory activity against α-glucosidase and a moderate inhibitory activity against α-amylase. The Lineweaver–Burk plots analysis elucidated that Trilobatin inhibited the enzyme non-competitively. DPPH scavenging activity of Trilobatin (IC 50 02=020.5702mg/ml) was higher than rutin (IC 50 02=020.7202mg/ml), which indicated that Trilobatin had a moderate antioxidant potential.
CONCLUSIONS:
These results suggest that Trilobatin is a potential effective α-glucosidase inhibitor for management of postprandial hyperglycemia with less side effect, and provide strong rationale for further animal and clinical studies.

Trilobatin Dilution Calculator

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Trilobatin Molarity Calculator

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Preparing Stock Solutions of Trilobatin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2915 mL 11.4574 mL 22.9148 mL 45.8295 mL 57.2869 mL
5 mM 0.4583 mL 2.2915 mL 4.583 mL 9.1659 mL 11.4574 mL
10 mM 0.2291 mL 1.1457 mL 2.2915 mL 4.583 mL 5.7287 mL
50 mM 0.0458 mL 0.2291 mL 0.4583 mL 0.9166 mL 1.1457 mL
100 mM 0.0229 mL 0.1146 mL 0.2291 mL 0.4583 mL 0.5729 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Trilobatin

Trilobatin attenuates the LPS-mediated inflammatory response by suppressing the NF-kappaB signaling pathway.[Pubmed:25053100]

Food Chem. 2015 Jan 1;166:609-15.

We investigated the anti-inflammatory effect of Trilobatin, the flavonoid isolated from the leaves of Lithocarpus polystachyus Rehd, as well as the underlying molecular mechanisms. Treatment with Trilobatin (0.005-5 muM) dose-dependently inhibited the lipopolysaccharide (LPS)-induced mRNA expression and secretion of pro-inflammatory cytokines, including tumor necrosis factor alpha (TNFalpha), interleukin-1beta (IL-1beta) and interleukin-6 (IL-6), in RAW 264.7 macrophages. However, no further inhibition was detected when the concentration of Trilobatin was increased to 50 muM. Western blot analysis confirmed that the mechanism of the anti-inflammatory effect was correlated with the inhibition of LPS-induced inhibitor of nuclear factor-kappa B alpha (IkappaBalpha) degradation and nuclear factor-kappa B (NF-kappaB) p65 phosphorylation. In addition, Trilobatin also showed a significant inhibition of LPS-induced TNFalpha and IL-6 at both the mRNA and protein levels in a mouse model. Our results suggest that Trilobatin potentially inhibits the LPS-induced inflammatory response by suppressing the NF-kappaB signaling pathway.

Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus.[Pubmed:15813365]

Z Naturforsch C. 2004 Jul-Aug;59(7-8):481-4.

In vitro antioxidant activities of three sweet dihydrochalcone glucosides from the leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae), Trilobatin 2"-acetate (1), phloridzin (2) and Trilobatin (3), were investigated. The IC50 (50% inhibitory concentration) values for compounds 1-3 of lipid peroxidation in rat liver homogenate were 261, 28, 88 microM, respectively. Compounds 1-3 increased superoxide dismutase (SOD) activity with EC50 (50% effective concentration) values of 575, 167, 128 microM, and glutathione peroxidase (GSH-Px) activity with EC50 values of 717, 347, 129 microM, respectively, and showed only weak DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity.

Description

Trilobatin, a natural sweetener derived from Lithocarpus polystachyus Rehd, Trilobatin is an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope. Neuroprotective effects. Trilobatin is also a SGLT1/2 inhibitor that selectively induces the proliferation of human hepatoblastoma cells.

Keywords:

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