Heliotrine

CAS# 303-33-3

Heliotrine

Catalog No. BCN1982----Order now to get a substantial discount!

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Quality Control of Heliotrine

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Chemical structure

Heliotrine

3D structure

Chemical Properties of Heliotrine

Cas No. 303-33-3 SDF Download SDF
PubChem ID 906426 Appearance White powder
Formula C16H27NO5 M.Wt 313.39
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in chloroform and ethan
Chemical Name [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate
SMILES CC(C)C(C(C)OC)(C(=O)OCC1=CCN2C1C(CC2)O)O
Standard InChIKey LMFKRLGHEKVMNT-UJDVCPFMSA-N
Standard InChI InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/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.

Source of Heliotrine

The herbs of Cynoglossum amabile

Biological Activity of Heliotrine

Description1. The pyrrolizidine alkaloid Heliotrine interferes with reporter signals derived from GAL4-based nuclear receptor transactivation assays by a mechanism independent of luciferase enzyme inhibition. 2. Acute hepatitis induced by Heliotrine is accompanied by uncoupling of oxidative phosphorylation in liver mitochondria.
TargetsATPase

Heliotrine Dilution Calculator

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Heliotrine Molarity Calculator

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Preparing Stock Solutions of Heliotrine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1909 mL 15.9546 mL 31.9091 mL 63.8182 mL 79.7728 mL
5 mM 0.6382 mL 3.1909 mL 6.3818 mL 12.7636 mL 15.9546 mL
10 mM 0.3191 mL 1.5955 mL 3.1909 mL 6.3818 mL 7.9773 mL
50 mM 0.0638 mL 0.3191 mL 0.6382 mL 1.2764 mL 1.5955 mL
100 mM 0.0319 mL 0.1595 mL 0.3191 mL 0.6382 mL 0.7977 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 Heliotrine

Utility of an appropriate reporter assay: Heliotrine interferes with GAL4/upstream activation sequence-driven reporter gene systems.[Pubmed:26212314]

Anal Biochem. 2015 Oct 15;487:45-8.

Reporter gene assays are widely used for the assessment of transcription factor activation following xenobiotic exposure of cells. A critical issue with such assays is the possibility of interference of test compounds with the test system, for example, by direct inhibition of the reporter enzyme. Here we show that the pyrrolizidine alkaloid Heliotrine interferes with reporter signals derived from GAL4-based nuclear receptor transactivation assays by a mechanism independent of luciferase enzyme inhibition. These data highlight the necessity to conduct proper control experiments in order to avoid perturbation of reporter assays by test chemicals.

Disturbances in oxidative phosphorylation in the liver of rats with heliotrine-induced hepatitis and restoration by phosphatidylcholine and ATP.[Pubmed:1668644]

Biomed Sci. 1991;2(5):460-4.

Acute hepatitis induced by Heliotrine is accompanied by uncoupling of oxidative phosphorylation in liver mitochondria. The rate of oxygen uptake during succinate oxidation increased in all metabolic states, while the respiratory control index decreased by 45% because of the greater increase in the respiration rate in state 4 by comparison with that in state 3. Heliotrine poisoning also halved the rate of oxygen uptake in rat liver homogenates in the presence of ascorbate and tetramethylene-p-phenylenediamine. This is indicative of a lowering of cytochrome oxidase activity and of energy metabolism disturbances in rat liver. Preparations of cotton phosphatidylcholine (PC), both purified and as ATP-containing complexes (PC+ATP), as well as ATP alone, reduced the metabolic disorders in liver mitochondria of rats with acute Heliotrine-induced hepatitis. The therapeutic effect of these preparations consisted in the restoration of oxidative phosphorylation coupling and of the cytochrome oxidase activity. The effect of PC+ATP was much greater than either PC or ATP alone. In contrast, the commercial preparation, Essential, had no beneficial effect.

Comparison of the toxic effects of dehydroheliotridine and heliotrine in pregnant rats and their embryos.[Pubmed:7431152]

J Pathol. 1980 Aug;131(4):339-55.

Female hooded rats were injected intraperitoneally on the 14th day of pregnancy with dehydroheliotridine (DHH), a pyrrolic metabolite of pyrrolizidine alkaloids, at 30 to 90 mg/kg, or with the alkaloid Heliotrine at 200 mg/kg and the effects on the embryos were evaluated on the 20th day. DHH was both growth-retarding and teratogenic. A dose of 40 mg DHH/kg approximated 200 mg Heliotrine/kg in its effects on embryos, the principal abnormalities being skeletal, including retarded ossification, distorted ribs and long bones, cleft palate and feet defects. At higher dose rates growth almost ceased in many tissues and although more than 60 per cent. of the embryos were alive they would not have survived birth. All were very immature and had multiple skeletal and visceral defects. The effects observed in the liver were anomalous in that the embryonic parenchyma showed little response to the anti-mitotic activity of DHH.

Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine.[Pubmed:24375927]

Mol Nutr Food Res. 2014 May;58(5):995-1004.

SCOPE: 1,2-Unsaturated pyrrolizidine alkaloids (PA) are found in plants such as Asteraceae and Boraginaceae families. Acute PA poisoning via contaminated food or feed causes severe damage to liver depending on species-specific oral bioavailability. For assessing PA bioavailability, their passage across the intestinal barrier was investigated using Caco-2 cells. METHODS: Differentiated Caco-2 cells were exposed in transport chambers to the PA Heliotrine (Hn), echimidine (Em), senecionine (Sc), and senkirkine (Sk). Cell supernatants were analyzed by LC-MS/MS. RESULTS: PA pass Caco-2 monolayer from the apical into basolateral compartment depending on their chemical structure. Compared to the cyclic diesters Sc and Sk with a passage rate of 47% +/- 4 and 40% +/- 3, respectively, the transferred amount of the monoester Hn (32% +/- 3) and open-chained diester Em (13% +/- 2) was substantially lower. This suggested an active transport of Hn and Em. Using Madin-Darby canine kidney II/P-glycoprotein (ABCB1)-overexpressing cells, the active excretion of Hn and Em by ABCB1 from the gastrointestinal epithelium into the gut lumen was shown. CONCLUSION: PA cross the intestinal barrier structure-dependently. The passage of the noncyclic PA Hn and Em is reduced by an ABCB1-driven efflux into the gastrointestinal lumen resulting in a decreased oral bioavailability.

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