Trichodesmine

CAS# 548-90-3

Trichodesmine

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Quality Control of Trichodesmine

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Chemical structure

Trichodesmine

3D structure

Chemical Properties of Trichodesmine

Cas No. 548-90-3 SDF Download SDF
PubChem ID 119040 Appearance White-yellowish powder
Formula C18H27NO6 M.Wt 353.41
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in chloroform, methanol and water
SMILES CC(C)C1C(=O)OC2CCN3C2C(=CC3)COC(=O)C(C1(C)O)(C)O
Standard InChIKey SOODLZHDDSGRKL-FOOXYVKASA-N
Standard InChI InChI=1S/C18H27NO6/c1-10(2)13-15(20)25-12-6-8-19-7-5-11(14(12)19)9-24-16(21)18(4,23)17(13,3)22/h5,10,12-14,22-23H,6-9H2,1-4H3/t12-,13+,14-,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.

Source of Trichodesmine

1 Heliotropium sp. 2 Trichodesma sp.

Biological Activity of Trichodesmine

Description1. Trichodesmine has greater lethality and neurotoxicity than monocrotaline, because of the two structural characteristics: (a) steric hindrance at position 14 of dehydroTrichodesmine results in greater resistance to hydrolysis, allowing more to be released from the liver and to be delivered to the brain; (b) the larger isopropyl substituent at position 14 of dehydroTrichodesmine renders the molecule more lipophilic, leading to greater penetration of the brain.

Trichodesmine Dilution Calculator

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Preparing Stock Solutions of Trichodesmine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8296 mL 14.1479 mL 28.2957 mL 56.5915 mL 70.7394 mL
5 mM 0.5659 mL 2.8296 mL 5.6591 mL 11.3183 mL 14.1479 mL
10 mM 0.283 mL 1.4148 mL 2.8296 mL 5.6591 mL 7.0739 mL
50 mM 0.0566 mL 0.283 mL 0.5659 mL 1.1318 mL 1.4148 mL
100 mM 0.0283 mL 0.1415 mL 0.283 mL 0.5659 mL 0.7074 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 Trichodesmine

The comparative metabolism of the four pyrrolizidine alkaloids, seneciphylline, retrorsine, monocrotaline, and trichodesmine in the isolated, perfused rat liver.[Pubmed:7645024]

Toxicol Appl Pharmacol. 1995 Aug;133(2):277-84.

Despite their similarity in structure, pyrrolizidine alkaloids (PAs) vary in their LD50s and in the organs in which toxicity is expressed. We have examined whether there are differences in the metabolism of certain PAs that are associated with these quantitative and qualitative differences in toxicity. Isolated rat livers were perfused with one of four PAs (seneciphylline, retrorsine, monocrotaline, and Trichodesmine) at 0.5 mM for 1 hr, and the pyrrolic metabolites determined that were released into perfusate and bile or bound in the liver. The proportion of the PA removed by the liver varied from 93% for retrorsine to 55% for Trichodesmine. However, Trichodesmine-perfused livers released the greatest amount of the dehydroalkaloid into the perfusate. These reactive pyrrolic metabolites appear to be largely responsible for the toxicity of PAs. Over the course of a 1-hr perfusion, dehydroalkaloid release varied fourfold among the PAs examined. Seneciphylline and retrorsine significantly increased bile flow. Highest concentrations of PAs in bile were achieved at 30-40 min perfusion. Conversion of dehydroalkaloid to the conjugate 7-glutathionyl-6,7-dihydro-1-hydroxymethyl-5H-pyrrolizine (GSDHP) is a detoxification reaction. GSDHP release into bile varied from 80 nmol/g liver for Trichodesmine to 880 nmol/g for retrorsine. Release of the less toxic hydrolytic product of dehydroalkaloids, 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine, was also determined. Bound pyrroles in liver are probably an indication of heptatoxicity. At the end of perfusion these varied from 55 nmol/g for monocrotaline to 195 nmol/g for retrorsine. The chemical form of the bound pyrroles is a 7-thioether conjugate of 6,7-dihydro-1-hydroxymethyl-5H-pyrrolizine. No 7,9-dithio conjugate was detected, indicating that only monoalkylation has been found. These differences in metabolic pattern reflect differences in reactivity of the initially formed dehydroalkaloid and can account for the toxicological differences between the parent PAs.

Physicochemical and metabolic basis for the differing neurotoxicity of the pyrrolizidine alkaloids, trichodesmine and monocrotaline.[Pubmed:9182239]

Neurochem Res. 1996 Feb;21(2):141-6.

Monocrotaline and Trichodesmine are structurally closely related pyrrolizidine alkaloids (PAs) exhibiting different extrahepatic toxicities, Trichodesmine being neurotoxic (LD(50) 57 mu mol/kg) and monocrotaline pneumotoxic (LD(50) 335 mu mol/kg). We have compared certain physicochemical properties and metabolic activities of these two PAs in order to understand the quantitative and qualitative differences in toxicity. Both PAs were metabolized in the isolated, perfused rat liver to highly reactive pyrrolic dehydroalkaloids that appear to be responsible for the toxicity of PAs. More dehydroTrichodesmine (468 nmol/g liver) than dehydromonocrotaline (116 nmol/g liver) was released from liver into perfusate on perfusion for 1 hr with 0.5 mM of the parent PA. DehydroTrichodesmine had a significantly longer aqueous half-life (5.4 sec) than that of dehydromonocrotaline (3.4 sec). In vivo, significantly higher levels of bound pyrroles were found in the brain 18 hr after injection of Trichodesmine (25 mg/kg; i.p.) than were seen following either an equal dose (25 mg/kg; i.p.) or an equitoxic dose (90 mg/kg; i.p.) of monocrotaline. Trichodesmine had a higher partition coefficient than monocrotaline for both chloroform and heptane, indicating its greater lipophilicity. The pK(a) of Trichodesmine (7.07) was only slightly higher than that of monocrotaline (pK(a inverted question mark 6.83), suggesting that a difference in degree of ionization was not a major factor affecting the relative ability of the dehydroalkaloids to cross the blood-brain barrier. We conclude that the greater lethality and neurotoxicity of Trichodesmine compared to monocrotaline is due to two structural characteristics: (i) steric hindrance at position 14 of dehydroTrichodesmine results in greater resistance to hydrolysis, allowing more to be released from the liver and to be delivered to the brain; (ii) the larger isopropyl substituent at position 14 of dehydroTrichodesmine renders the molecule more lipophilic, leading to greater penetration of the brain.

The effect of the pyrrolizidine alkaloids, monocrotaline and trichodesmine, on tissue pyrrole binding and glutathione metabolism in the rat.[Pubmed:7660367]

Toxicon. 1995 May;33(5):627-34.

One day after in vivo administration of equitoxic doses of the hepatotoxic and pneumotoxic pyrrolizidine alkaloid, monocrotaline (65 mg/kg, i. p.) or the related hepatotoxic and neurotoxic alkaloid Trichodesmine (15 mg/kg, i. p.) hepatic GSH levels are increased by more than 50%. These doses of alkaloids represent 60% of the LD50 values. Accompanying these changes in GSH levels is an increase in the overall rate of GSH synthesis in supernatants of alkaloid-exposed livers. The ability of the rat to metabolize the two alkaloids was shown by the appearance of tissuebound pyrrolic metabolites of pyrrolizidines in various organs. The levels of these metabolites appear to correlate with organ toxicity. For the hepatic and pneumotoxic alkaloid, monocrotaline, higher levels are found in liver (17 nmoles/g tissue) and lung (10 nmoles/g) than for Trichodesmine (7 nmoles/g and 8 nmoles/g, respectively). For the neurotoxic alkaloid, Trichodesmine, higher levels are found in brain (3.8 nmoles/g tissue) than for monocrotaline (1.7 nmoles/g tissue).

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