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Trilobatin

Names

[ CAS No. ]:
4192-90-9

[ Name ]:
Trilobatin

[Synonym ]:
UNII:23298I791N
1-Propanone, 1-[4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
3,5-Dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl β-D-glucopyranoside
p-Phloridzin
phloretin-4-D-glucoside
T6OTJ BOR CQ EQ DV2R DQ&& CQ DQ EQ F1Q &&β-D-Gluco Form
p-Phlorizin
1-Propanone, 1-(4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
Trilobatin
1-(4-(β-D-Glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone

Biological Activity

[Description]:

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].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV
Research Areas >> Infection
Signaling Pathways >> Membrane Transporter/Ion Channel >> SGLT

[Target]

HIV-1

SGLT1/2


[In Vitro]

Trilobatin protects against oxidative injury in neuronal PC12 cells through regulating mitochondrial reactive oxygen species (mtROS) homeostasis in the first time, which is, at least partly, mediated through the AMPK/Nrf2/Sirt3 signaling pathway[1].

[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.

[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.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
787.9±60.0 °C at 760 mmHg

[ Melting Point ]:
163 °C

[ Molecular Formula ]:
C21H24O10

[ Molecular Weight ]:
436.409

[ Flash Point ]:
277.1±26.4 °C

[ Exact Mass ]:
436.136932

[ PSA ]:
177.14000

[ LogP ]:
1.43

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.686

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds