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Xanthoangelol B

CAS# 132998-81-3

Xanthoangelol B

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Quality Control of Xanthoangelol B

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Chemical structure

Xanthoangelol B

3D structure

Chemical Properties of Xanthoangelol B

Cas No. 132998-81-3 SDF Download SDF
PubChem ID 10409180 Appearance Powder
Formula C25H28O5 M.Wt 408.49
Type of Compound Chalcones Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-1-[2,4-dihydroxy-3-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl]phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES CC(=C)C(CCC(=CCC1=C(C=CC(=C1O)C(=O)C=CC2=CC=C(C=C2)O)O)C)O
Standard InChIKey NCHZAFAGBAEJJJ-BAYITLGHSA-N
Standard InChI InChI=1S/C25H28O5/c1-16(2)22(27)13-5-17(3)4-11-20-24(29)15-12-21(25(20)30)23(28)14-8-18-6-9-19(26)10-7-18/h4,6-10,12,14-15,22,26-27,29-30H,1,5,11,13H2,2-3H3/b14-8+,17-4+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Xanthoangelol B

DescriptionXanthoangelol B and its derivative PM-56 were shown to bind directly to SaeS and inhibit its histidine kinase activity, which suggests a possibility of a broad spectrum inhibitor of histidine kinases. Xanthoangelol B inhibited the phenylephrine-induced vasoconstriction most strongly, and the inhibitory mechanism of it on phenylephrine-induced vasoconstriction might involve the direct inhibition of smooth muscle functions through the reduction of [Ca2+]i elevation without affecting EDRF/NO production.
TargetsCalcium Channel | NO | NMDA receptor
In vitro

Artery relaxation by chalcones isolated from the roots of Angelica keiskei.[Pubmed: 11345693 ]

Planta Med. 2001 Apr;67(3):230-5.


METHODS AND RESULTS:
An EtOAc-soluble fraction from a 50% EtOH extract of the roots of Angelica keiskei inhibited phenylephrine-induced vasoconstriction in rat aortic rings, while an EtOAc-insoluble fraction had no effect at 100 micrograms/ml. Five active substances isolated from the EtOAc-soluble fraction of the roots were identified as xanthoangelol (1), 4-hydroxyderricin (2), and Xanthoangelol B (3), xanthoangelol E (4) and xanthoangelol F (5), which inhibited phenylephrine-induced vasoconstriction at the concentrations of 10-100 micrograms/ml. It was found that xanthoangelol (1), 4-hydroxyderricin (2), and xanthoangelols E (4) and F (5) inhibited the phenylephrine-induced vasoconstriction through endothelium-dependent endothelium-derived relaxing factor (EDRF) production and/or nitric oxide (NO) production. Among the five chalcones, Xanthoangelol B (3) inhibited the phenylephrine-induced vasoconstriction most strongly, and it inhibited the phenylephrine-induced vasoconstriction in the presence or absence of endothelium and in the presence or absence of NG-monomethyl-L-arginine (L-NMMA) (an NO synthetase inhibitor). Furthermore, 4-hydroxyderricin (2) and Xanthoangelol B (3) at concentrations of 10-100 micrograms/ml concentration-dependently inhibited the elevation of intracellular free calcium [Ca2+]i induced by phenylephrine.
CONCLUSIONS:
These results demonstrate that compounds 1, 2, 4 and 5 inhibit phenylephrine-induced vasoconstriction through endothelium-dependent production of EDRF/NO and/or through the reduction of the [Ca2+]i elevation induced by phenylephrine. On the other hand, the inhibitory mechanism of compound 3 on phenylephrine-induced vasoconstriction might involve the direct inhibition of smooth muscle functions through the reduction of [Ca2+]i elevation without affecting EDRF/NO production.

Protocol of Xanthoangelol B

Kinase Assay

Total Synthesis of Xanthoangelol B and Its Various Fragments: Toward Inhibition of Virulence Factor Production of Staphylococcus aureus.[Pubmed: 30388007 ]

J Med Chem. 2018 Dec 13;61(23):10473-10487.

As an alternative strategy to fight antibiotic resistance, two-component systems (TCSs) have emerged as novel targets. Among TCSs, master virulence regulators that control the expression of multiple virulence factors are considered as excellent antivirulence targets. In Staphylococcus aureus, virulence factor expression is tightly regulated by a few master regulators, including the SaeRS TCS.
METHODS AND RESULTS:
In this study, we used a SaeRS GFP-reporter system to screen natural compound inhibitors of SaeRS, and identified Xanthoangelol B 1, a prenylated chalcone from Angelica keiskei as a hit. We have synthesized 1 and its derivative PM-56 and shown that 1 and PM-56 both had excellent inhibitory potency against the SaeRS TCS, as demonstrated by various in vitro and in vivo experiments.
CONCLUSIONS:
As a mode of action, 1 and PM-56 were shown to bind directly to SaeS and inhibit its histidine kinase activity, which suggests a possibility of a broad spectrum inhibitor of histidine kinases.

Xanthoangelol B Dilution Calculator

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Xanthoangelol B Molarity Calculator

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Preparing Stock Solutions of Xanthoangelol B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.448 mL 12.2402 mL 24.4804 mL 48.9608 mL 61.201 mL
5 mM 0.4896 mL 2.448 mL 4.8961 mL 9.7922 mL 12.2402 mL
10 mM 0.2448 mL 1.224 mL 2.448 mL 4.8961 mL 6.1201 mL
50 mM 0.049 mL 0.2448 mL 0.4896 mL 0.9792 mL 1.224 mL
100 mM 0.0245 mL 0.1224 mL 0.2448 mL 0.4896 mL 0.612 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Xanthoangelol B

Total Synthesis of Xanthoangelol B and Its Various Fragments: Toward Inhibition of Virulence Factor Production of Staphylococcus aureus.[Pubmed:30388007]

J Med Chem. 2018 Nov 14.

As an alternative strategy to fight antibiotic resistance, two-component systems (TCSs) have emerged as novel targets. Among TCSs, master virulence regulators that control the expression of multiple virulence factors are considered as excellent antivirulence targets. In Staphylococcus aureus, virulence factor expression is tightly regulated by a few master regulators, including the SaeRS TCS. In this study, we used a SaeRS GFP-reporter system to screen natural compound inhibitors of SaeRS, and identified Xanthoangelol B 1, a prenylated chalcone from Angelica keiskei as a hit. We have synthesized 1 and its derivative PM-56 and shown that 1 and PM-56 both had excellent inhibitory potency against the SaeRS TCS, as demonstrated by various in vitro and in vivo experiments. As a mode of action, 1 and PM-56 were shown to bind directly to SaeS and inhibit its histidine kinase activity, which suggests a possibility of a broad spectrum inhibitor of histidine kinases.

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