PRUNINDIHYDROCHALCONE Chemical Properties

Melting point:

170-173 °C

Boiling point:

787.9±60.0 °C(Predicted)

Density 

1.555±0.06 g/cm3(Predicted)

FEMA 

4674 | TRILOBATIN

storage temp. 

4°C, protect from light

solubility 

DMF: 20 mg/ml; DMSO: 25 mg/ml; Ethanol: 20 mg/ml; PBS (pH 7.2): 0.1 mg/ml

form 

A crystalline solid

pka

6.85±0.40(Predicted)

color 

White to off-white

JECFA Number

2171

InChIKey

GSTCPEBQYSOEHV-LKLLPNDVNA-N

SMILES

C(C1C(=CC(O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)=CC=1O)O)(=O)CCC1C=CC(O)=CC=1 |&1:6,7,8,10,12,r|

LogP

1.36

Safety Information

HS Code 

29329990

PRUNINDIHYDROCHALCONE Usage And Synthesis

Chemical Properties

Soluble in organic solvents such as methanol, ethanol, and DMSO.

Uses

Trilobatin, a natural sweetener derived from?Lithocarpus polystachyus?Rehd[1], Trilobatin?is an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope[2]. Neuroprotective effects[1]. Trilobatin is also a SGLT1/2 inhibitor that selectively induces the proliferation of human hepatoblastoma cells[3].

Definition

ChEBI: 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.

IC 50

HIV-1; SGLT1; SGLT2

References

[1] Gao J, et al. Trilobatin?Protects Against Oxidative Injury in Neuronal PC12 Cells Through Regulating Mitochondrial ROS Homeostasis Mediated by AMPK/Nrf2/Sirt3 Signaling Pathway. Front Mol Neurosci.?2018 Jul 30;11:267. DOI:10.3389/fnmol.2018.00267
[2] Yin S,?et al. Trilobatin?as an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope. FEBS Lett.?2018 Jul;592(13):2361-2377. DOI:10.1002/1873-3468.13113

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