1,3,5-Trihydroxy-4-prenylxanthone | CAS:53377-61-0

1,3,5-Trihydroxy-4-prenylxanthone

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Description:

1,3,5-Trihydroxy-4-prenylxanthone is a relatively potent inhibitor of phosphodiesterase type 5 (PDE5), with an IC50 value of 3.0 μM; it shows in vitro inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), with IC50 values of 56.3plusmn;0.4 and 46.0plusmn;0.3 M, respectively. 1,3,5-Trihydroxy-4-prenylxanthone inhibits LPS-induced NF-κB and AP-1 activations by interfering with the posttranslational modification (phosphorylation and/or ubiquitinylation) of IRAK-1 in the cell membrane to impede TAK1-mediated activation of IKK and MAPKs signal transduction.

Targets:

NF-kB | IkB | AP-1 | JNK | ERK | TGF-β/Smad | AChR | IKK | BChR | AChR | PDE | IRAK-1 | TAK

In vitro:

Nat Prod Commun. 2015 Feb;10(2):301-3.

Phosphodiesterase inhibitory activity of the flavonoids and xanthones from Anaxagorea luzonensis.[Pubmed: 25920267]

METHODS AND RESULTS:
Five flavonoids, one isoflavone and five xanthones were isolated from Anaxagorea luzonensis. Of these eleven isolated compounds, 1,3,5-Trihydroxy-4-prenylxanthone (3) was a relatively potent inhibitor of phosphodiesterase type 5 (PDE5), with an IC50 value of 3.0 μM.
CONCLUSIONS:
This is the first report showing that natural xanthones can exhibit promising PDE5 inhibitory activity. Moreover, this study revealed that the presence of the C-4 prenyl residue attached to the xanthone core is correlated with the significant PDE5 inhibitory activity.

Journal of Medicinal Plant Research, 2012 , 6 (21):3781-3785.

Cholinesterase inhibitory activities of xanthones from Anaxagorea luzonensis A. Gray[Reference: WebLink]

METHODS AND RESULTS:
Five xanthones (1-5) were isolated from the heartwood of Anaxagorea luzonensis A. Gray (Annonaceae) and this is the first report of the isolation of xanthone 1 (6-deoxyisojacareubin) from this species. The in vitro inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) of these isolated xanthones was highest in 1,3,5-Trihydroxy-4-prenylxanthone (3) for both enzymes with IC50 values of 56.3±0.4 and 46.0±0.3 μM, respectively.
CONCLUSIONS:
The presence of the C-4 prenyl residue attached to the xanthone core co-orrelated significantly with the AChE and BChE inhibitory activities and was significantly reduced by hydroxylation (removal of the carbon double bond and addition of a hydroxyl group).

1,3,5-Trihydroxy-4-prenylxanthone Description

Source:	The herbs of Cudrania tricuspidata
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Biochem Pharmacol. 2011 Mar 15;81(6):752-60.

1,3,5-trihydroxy-4-prenylxanthone represses lipopolysaccharide-induced iNOS expression via impeding posttranslational modification of IRAK-1.[Pubmed: 21232528]

1,3,5-Trihydroxy-4-prenylxanthone (TH-4-PX) isolated from Cudrania cochinchinensis repressed lipopolysaccharide (LPS)-induced NO production in RAW264.7 macrophages.
METHODS AND RESULTS:
Here we further examined the underlying mechanisms using RT-PCR and Western blot analyses. Consistent with NO inhibition, suppression of LPS-induced iNOS expression by 1,3,5-Trihydroxy-4-prenylxanthone through abolishing IκB kinase (IKK) phosphorylation, IκB degradation and nuclear factor-κB (NF-κB) nuclear translocation was observed. After LPS stimulation, the increased 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 c-Jun NH2-terminal kinase (JNK) and extracellular signal-regulated kinase, (ERK) were all significantly suppressed by 1,3,5-Trihydroxy-4-prenylxanthone, while p38 remained unaffected. A further experiment revealed that 1,3,5-Trihydroxy-4-prenylxanthone inhibited the phosphorylation of transforming growth factor-β (TGF-β)-activated kinase 1 (TAK1), an upstream signaling molecule required for IKK and mitogen-activated protein kinases (MAPKs) activation. Interestingly, the modified pattern of IRAK-1 in the presence LPS was significantly attenuated by 1,3,5-Trihydroxy-4-prenylxanthone treatment.
CONCLUSIONS:
In conclusion, 1,3,5-Trihydroxy-4-prenylxanthone inhibited LPS-induced NF-κB and AP-1 activations by interfering with the posttranslational modification (phosphorylation and/or ubiquitinylation) of IRAK-1 in the cell membrane to impede TAK1-mediated activation of IKK and MAPKs signal transduction.

Product Name	1,3,5-Trihydroxy-4-prenylxanthone
Price:
CAS No.:	53377-61-0
Catalog No.:	CFN98891
Molecular Formula:	C₁₈H₁₆O₅
Molecular Weight:	312.3 g/mol
Purity:	>=98%
Type of Compound:	Xanthones
Physical Desc.:	Yellow powder
Source:	The herbs of Cudrania tricuspidata
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Anticholinesterase Compound Library Xanthones Compound Library TGF-β/Smad Inhibitor Library PDE Inhibitor Library NF-kB Inhibitor Library JNK Inhibitor Library IKK Inhibitor Library IkB Inhibitor Library ERK Inhibitor Library AP-1 Inhibitor Library AChR Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.202 mL	16.0102 mL	32.0205 mL	64.041 mL	80.0512 mL
5 mM	0.6404 mL	3.202 mL	6.4041 mL	12.8082 mL	16.0102 mL
10 mM	0.3202 mL	1.601 mL	3.202 mL	6.4041 mL	8.0051 mL
50 mM	0.064 mL	0.3202 mL	0.6404 mL	1.2808 mL	1.601 mL
100 mM	0.032 mL	0.1601 mL	0.3202 mL	0.6404 mL	0.8005 mL

CFN96469	Ugaxanthone	13179-11-8	328.32	C₁₈H₁₆O₆
CFN96573	Isojacareubin	50597-93-8	326.31	C₁₈H₁₄O₆
CFN92541	1,3,6,8-tetrahydroxy-4-(3-methyl-2-buten-1-yl)-9H-Xanthen-9-one	1319198-98-5	328.3	C₁₈H₁₆O₆
CFN96276	6-Deoxyjacareubin	16265-56-8	310.3	C₁₈H₁₄O₅
CFN98022	1,3,7-Trihydroxy-2-prenylxanthone	20245-39-0	312.3	C₁₈H₁₆O₅
CFN97264	1,7-Dihydroxy-3-methoxy-2-prenylxanthone	77741-58-3	326.4	C₁₉H₁₈O₅
CFN99202	1,5,8-Trihydroxy-3-methoxy-2-prenylxanthone	110187-11-6	342.4	C₁₉H₁₈O₆
CFN99016	1,4,5,6-Tetrahydroxy-7-prenylxanthone	1001424-68-5	328.3	C₁₈H₁₆O₆
CFN99675	1,4,6-Trihydroxy-5-methoxy-7-prenylxanthone	160623-47-2	342.4	C₁₉H₁₈O₆
CFN97493	O-Demethylforbexanthone	92609-77-3	326.3	C₁₈H₁₄O₆