52589-11-4

52589-11-4 structure

Name: Phellamurin
Chemical Name: phellamurin
CAS Number: 52589-11-4
Molecular Formula: C₂₆H₃₀O₁₁
Molecular Weight: 518.510
Catalog: Natural product Flavonoids
Create Date: 2017-06-03 10:08:16
Modify Date: 2024-01-09 20:16:23
Phellamurin is a plant flavonone glycoside from the leaves of Phellodendron amurense and inhibits intestinal P-glycoprotein. Phellamurin also inhibits egg laying by Papilio protenor. Phellamurin induces cells apoptosis and has anti-tumor activity[1][2][3].

Name	phellamurin
Synonyms	(2R,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4-oxo-3,4-dihydro-2H-chromen-7-yl β-D-glucopyranoside Phellamurin 4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-, (2R-trans)- 4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-, (2R,3R)-

Description	Phellamurin is a plant flavonone glycoside from the leaves of Phellodendron amurense and inhibits intestinal P-glycoprotein. Phellamurin also inhibits egg laying by Papilio protenor. Phellamurin induces cells apoptosis and has anti-tumor activity[1][2][3].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Signaling Pathways >> Membrane Transporter/Ion Channel >> P-glycoprotein Research Areas >> Metabolic Disease
In Vitro	Phellamurin (0-10 μg/mL; 48 hours; U2OS and Saos-2 cells) treatment leads to a repression of cell viability in U2OS and Saos-2 cells in a dose-dependent manner[1]. Phellamurin (0-10 μg/mL; 48 hours; U2OS and Saos-2 cells) treatment concentration-dependently promots the apoptosis of U2OS and Saos-2 cells[1]. Phellamurin (0-10 μg/mL; 48 hours; U2OS and Saos-2 cells) treatment declines the ratios of p-PI3K/PI3K, p-AKT/AKT, and p-mTOR/mTOR in U2OS and Saos-2 cells[1]. Cell Viability Assay[1] Cell Line: U2OS and Saos-2 cells Concentration: 0 μg/mL, 2.5 μg/mL, 5 μg/mL, and 10 μg/mL Incubation Time: 48 hours Result: Suppressed the viability of U2OS and Saos-2 cells in a concentration-dependent manner. Apoptosis Analysis[1] Cell Line: U2OS and Saos-2 cells Concentration: 0 μg/mL, 2.5 μg/mL, 5 μg/mL, and 10 μg/mL Incubation Time: 48 hours Result: Induced apoptosis of U2OS and Saos-2 cells in a concentration-dependent manner. Western Blot Analysis[1] Cell Line: U2OS and Saos-2 cells Concentration: 0 μg/mL and 10 μg/mL Incubation Time: 48 hours Result: Repressed the PI3K/AKT/mTOR pathway in U2OS and Saos-2 cells.
In Vivo	Phellamurin (50 mg/kg/day; intraperitoneal injection; daily; for 21 days; female BALB/c nude mice) treatment represses osteosarcoma tumor growth in vivo. The ratios of p-PI3K/PI3K, p-AKT/AKT, and p-mTOR/mTOR are decreased in xenograft in Phellamurin-treated mice[1]. Animal Model: Athymic female BALB/c nude mice (6 weeks old ) injected with U2OS cells[1] Dosage: 50 mg/kg/day Administration: Intraperitoneal injection; daily; for 21 days Result: Repressed osteosarcoma tumor growth in vivo.
References	[1]. Hongzhi Zhang, et al. Anti-tumor Efficacy of Phellamurin in Osteosarcoma Cells: Involvement of the PI3K/AKT/mTOR Pathway. Eur J Pharmacol. 2019 Sep 5;858:172477. [2]. Hung-Yi Chen, et al. Marked Decrease of Cyclosporin Absorption Caused by Phellamurin in Rats. Planta Med. 2002 Feb;68(2):138-41. [3]. Keiichi Honda, et al. Synergistic or Antagonistic Modulation of Oviposition Response of Two Swallowtail Butterflies, Papilio Maackii and P. Protenor, to Phellodendron Amurense by Its Constitutive Prenylated Flavonoid, Phellamurin. J Chem Ecol. 2011 Jun;37(6):575-81.

Density	1.5±0.1 g/cm3
Boiling Point	861.5±65.0 °C at 760 mmHg
Molecular Formula	C₂₆H₃₀O₁₁
Molecular Weight	518.510
Flash Point	290.7±27.8 °C
Exact Mass	518.178833
PSA	186.37000
LogP	2.14
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.672

Hazard Codes	Xi

56-41-7	108-65-6
56-35-9	64-17-5
67-56-1	108-88-3
141-78-6	1310-73-2
13463-67-7	1333-86-4