1,3,5-Trihydroxy-4-prenylxanthone

Names

[ Name ]:
1,3,5-Trihydroxy-4-prenylxanthone

[Synonym ]:
9H-Xanthen-9-one, 1,3,5-trihydroxy-4-(3-methyl-2-buten-1-yl)-
1,3,5-trihydroxy-4-(3-methylbut-2-enyl)xanthen-9-one
1,3,5-Trihydroxy-4-(3-methyl-2-buten-1-yl)-9H-xanthen-9-one
2,4,6-trihydroxynitrobenzene
nitrophlorogucinol
Nitrophloroglucinol
1-Nitrophloroglucinol
1,3,5-trihydroxy-4-(3-methylbut-2-enyl)-9H-xanthen-9-one
1,3,5-Trihydroxy-2-nitrobenzene
2-nitro-phloroglucinol
hitrophloroglucinol

Biological Activity

[Description]:

1,3,5-Trihydroxy-4-prenylxanthone is a Na+/H+ exchange system (Na+/H+ Exchanger (NHE)) inhibitor with a minimum inhibitory concentration of 10 μg/mL[1]. 1,3,5-Trihydroxy-4-prenylxanthone is a phosphodiesterase type 5 (PDE5) (Phosphodiesterase (PDE)) inhibitor with an IC50 value of 3.0 μM[3]. 1,3,5-Trihydroxy-4-prenylxanthone inhibits Lipopolysaccharide (LPS) (Lipopolysaccharides (HY-D1056))-induced NO production in RAW264.7 macrophages, and has anti-inflammatory activities[2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Signaling Pathways >> Immunology/Inflammation >> NO Synthase

Research Areas >> Inflammation/Immunology

[Target]

PDE5:3 μM (IC50)

iNOS

Na+/H+ Exchanger

[In Vitro]

1,3,5-Trihydroxy-4-prenylxanthone（10-30 μM；18 小时）通过消除 IKK 磷酸化、IκB 降解和 NF-κB 核转位抑制 LPS 诱导的 iNOS 表达。 1,3,5-Trihydroxy-4-prenylxanthone 通过干扰 IRAK-1 的翻译后修饰来抑制 LPS 诱导的 iNOS 表达，从而阻断 TAK1 介导的 IKK 和 MAPK 信号转导激活，从而下调 NF-κB 和 AP-1 的激活[2]。 Western Blot Analysis[2] Cell Line: RAW264.7 macrophages Concentration: 10 μM, 20 μM and 30 μM Incubation Time: 18 hours Result: Showed suppression of LPS-induced iNOS expression. Suppressed the nuclear level of c-Fos and c-Jun (major components of activator protein-1, AP-1) and the phosphorylated level of upstream signal molecules, such as JNK and ERK.

[References]

[1]. [1] M Kobayashi, et al. Indonesian medicinal plants. XXI. Inhibitors of Na+/H+ exchanger from the bark of Erythrina variegata and the roots of Maclura cochinchinensis. Chem Pharm Bull (Tokyo). 1997 Oct;45(10):1615-9.

[2]. Wen-Fei Chiou, et al. 1,3,5-trihydroxy-4-prenylxanthone represses lipopolysaccharide-induced iNOS expression via impeding posttranslational modification of IRAK-1. Biochem Pharmacol. 2011 Mar 15;81(6):752-60.

[3]. Chalisa Sabphon, et al. Phosphodiesterase inhibitory activity of the flavonoids and xanthones from Anaxagorea luzonensis. Nat Prod Commun. 2015 Feb;10(2):301-3.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
550.7±49.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₁₆O₅

[ Molecular Weight ]:
312.317

[ Flash Point ]:
204.3±23.3 °C

[ Exact Mass ]:
312.099762

[ PSA ]:
90.90000

[ LogP ]:
3.26

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.676

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%