Adonifoline

CAS# 115712-88-4

Adonifoline

Catalog No. BCN2056----Order now to get a substantial discount!

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Quality Control of Adonifoline

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Chemical structure

Adonifoline

3D structure

Chemical Properties of Adonifoline

Cas No. 115712-88-4 SDF Download SDF
PubChem ID 15736564 Appearance Cryst.
Formula C18H23NO7 M.Wt 365.38
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,20R)-4-hydroxy-5,10-dimethyl-2,6,9,12-tetraoxa-17-azapentacyclo[12.5.1.14,8.08,10.017,20]henicos-14-ene-3,11-dione
SMILES CC1C2(CC3(CO1)C(O3)(C(=O)OCC4=CCN5C4C(CC5)OC2=O)C)O
Standard InChIKey MYOFCWPLRKBPJD-AQYQBICXSA-N
Standard InChI InChI=1S/C18H23NO7/c1-10-18(22)8-17(9-24-10)16(2,26-17)14(20)23-7-11-3-5-19-6-4-12(13(11)19)25-15(18)21/h3,10,12-13,22H,4-9H2,1-2H3/t10?,12-,13-,16?,17?,18?/m1/s1
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 Adonifoline

Description1. Adonifoline is a hepatotoxic pyrrolizidine alkaloid.

Adonifoline Dilution Calculator

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Adonifoline Molarity Calculator

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Preparing Stock Solutions of Adonifoline

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7369 mL 13.6844 mL 27.3688 mL 54.7375 mL 68.4219 mL
5 mM 0.5474 mL 2.7369 mL 5.4738 mL 10.9475 mL 13.6844 mL
10 mM 0.2737 mL 1.3684 mL 2.7369 mL 5.4738 mL 6.8422 mL
50 mM 0.0547 mL 0.2737 mL 0.5474 mL 1.0948 mL 1.3684 mL
100 mM 0.0274 mL 0.1368 mL 0.2737 mL 0.5474 mL 0.6842 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 Adonifoline

Glucuronidation, a new metabolic pathway for pyrrolizidine alkaloids.[Pubmed:20092275]

Chem Res Toxicol. 2010 Mar 15;23(3):591-9.

Pyrrolizidine alkaloids (PAs) possess significant hepatotoxicity to humans and animals after metabolic activation by liver P450 enzymes. Metabolism pathways of PAs have been studied for several decades, including metabolic activation, hydroxylation, N-oxidation, and hydrolysis. However, the glucuronidation of intact PAs has not been investigated, although glucuronidation plays an important role in the elimination and detoxication of xenobiotics. In this study, PAs glucuronidation was investigated, and three important points were found. First, we demonstrated that senecionine (SEN)-a representative hepatotoxic PA-could be conjugated by glucuronic acid via an N-glucuronidation reaction catalyzed by uridine diphosphate glucuronosyl transferase in human liver microsomes. Second, glucuronidation of SEN was catalyzed not only by human but also other animal species and showed significant species differences. Rabbits, cattle, sheep, pigs, and humans showed the significantly higher glucuronidation activity than mice, rats, dogs, and guinea pigs on SEN. Kinetics of SEN glucuronidation in humans, pigs, and rabbits followed the one-site binding model of the Michaelis-Menten equation, while cattle and sheep followed the two-sites binding model of the Michaelis-Menten equation. Third, besides SEN, other hepatotoxic PAs including monocrotaline, Adonifoline, and isoline also underwent N-glucuronidation in humans and several animal species such as rabbits, cattle, sheep, and pigs.

Identification of metabolites of adonifoline, a hepatotoxic pyrrolizidine alkaloid, by liquid chromatography/tandem and high-resolution mass spectrometry.[Pubmed:19918941]

Rapid Commun Mass Spectrom. 2009 Dec;23(24):3907-16.

Hepatotoxic pyrrolizidine alkaloid (HPA)-containing plants have always been a threat to human and livestock health worldwide. Adonifoline, a main HPA in Senecio scandens Buch.-Ham. ex D. Don (Qianli guang), was used officially as an infusion in cases of oral and pharyngeal infections in China. In this study in vivo metabolism of Adonifoline was studied for the first time by identifying the metabolites of Adonifoline present in bile, urine and feces of rats using liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS(n)) (ion trap) as well as liquid chromatography/electrospray ionization high-resolution mass spectrometry (LC/ESI-HRMS) (quadrupole-time of flight). In total 19 metabolites were identified and, among them, retronecine-N-oxides were confirmed by matching their fragmentation patterns with their fully characterized synthetic compounds. These metabolites are all involved in both phase I and phase II metabolic processes and the principal in vivo metabolism pathways of Adonifoline were proposed.

The comparative pharmacokinetics of two pyrrolizidine alkaloids, senecionine and adonifoline, and their main metabolites in rats after intravenous and oral administration by UPLC/ESIMS.[Pubmed:21573843]

Anal Bioanal Chem. 2011 Jul;401(1):275-87.

Pyrrolizidine alkaloids (PAs) are considered to be one of the most hepatotoxic groups of compounds of plant origin and are present in about 3% of the world's flowering plants. Most PAs represent a considerable health hazard to both livestock and humans through the consumption of plants and PA-contaminated products such as milk, honey, herbal teas, and medicines. This study determined the differences in the in vivo pharmacokinetic behavior of senecionine (SEN), Adonifoline (ADO), and their main metabolites in rats after intravenous administration and oral administration by ultraperformance liquid chromatography/electrospray ionization mass spectrometry. Upon intravenous administration and oral administration of SEN and ADO, significant differences in pharmacokinetics were observed, with the SEN and ADO being absorbed fast with lower bioavailability and being quickly metabolized to PA N-oxides and hydroxylation products of PAs or their N-oxides. It could be seen that the plasma concentration ratio of senecionine N-oxide (SEN-NO) to SEN (C (SEN-NO)/C (SEN)) was significantly larger than that for Adonifoline N-oxide (ADO-NO) and ADO (C (ADO-NO)/C (ADO)) (P < 0.001) for both dosing routes in rats. The high N-oxygenation activity and extensive toxicity of SEN, compared with ADO, in rats raised the question of whether or not the higher metabolic rate of SEN in rats in vivo was related to its potent toxicity. The toxicity of SEN-NO and ADO-NO needs to be evaluated further and compared in vitro/in vivo. This study was most helpful for interpreting the metabolism of metabolic bioactivation and detoxication, and toxicity differences among SEN, ADO and other PAs.

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