Parsonsine

CAS# 72213-98-0

Parsonsine

Catalog No. BCN2111----Order now to get a substantial discount!

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Quality Control of Parsonsine

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Chemical structure

Parsonsine

3D structure

Chemical Properties of Parsonsine

Cas No. 72213-98-0 SDF Download SDF
PubChem ID 15060933 Appearance Powder
Formula C22H33NO8 M.Wt 439.50
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,4S,8R,9S,19R)-4,9-dihydroxy-8-methyl-4,9-di(propan-2-yl)-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione
SMILES CC1C(C(=O)OCC2=CCN3C2C(CC3)OC(=O)C(CC(=O)O1)(C(C)C)O)(C(C)C)O
Standard InChIKey MPPSDVYCCOJJIB-QCNRXRGQSA-N
Standard InChI InChI=1S/C22H33NO8/c1-12(2)21(27)10-17(24)30-14(5)22(28,13(3)4)20(26)29-11-15-6-8-23-9-7-16(18(15)23)31-19(21)25/h6,12-14,16,18,27-28H,7-11H2,1-5H3/t14-,16-,18-,21+,22+/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.

Protocol of Parsonsine

Kinase Assay

Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi.[Pubmed: 12706631]

Insect Biochem Mol Biol. 2003 May;33(5):515-23.

Leaf beetles of the genus Platyphora, feeding on plant species containing pyrrolizidine alkaloids of the lycopsamine type, not only sequester these alkaloids and concentrate them in their exocrine defensive secretions, but also specifically process the plant acquired alkaloids.
METHODS AND RESULTS:
Using P. boucardi as subject, three mechanisms were studied: (i). utilization of host plant alkaloids that are not sequestered per se; (ii). elucidation of the mechanism of the already documented C-7 epimerization of heliotridine O(9)-monoesters; (iii). the specificity of insect catalyzed necine base esterification. P. boucardi does not sequester the triester Parsonsine, the principal alkaloid of its host plant Prestonia portobellensis (Apocynaceae). Beetles fed with a purified mixture of nor-derivatives of Parsonsine, obtained from Parsonsia laevigata, did not sequester the triesters but transformed them by partial degradation into monoesters that are accumulated in the defensive secretions. The mechanism of the previously described transformation of rinderine into intermedine by C-7 epimerization was elucidated by feeding C-7 deuterated heliotrine (3'-methylrinderine). The transformation of heliotrine into epiheliotrine (3'-methylintermedine) catalyzed by P. boucardi is accompanied by complete loss of deuterium, indicating the same mechanism of an oxidation-reduction process via a ketone intermediate as recently demonstrated in a pyrrolizidine alkaloid sequestering lepidopteran.
CONCLUSIONS:
P. boucardi is able to form ester alkaloids from five different necine bases fed as radioactively labeled substrates. However, besides C-7 epimerization the beetles are not able to convert simple necine bases into retronecine. The functional importance of the various alkaloid transformations is discussed in comparison to striking parallels of analogous reactions known from pyrrolizidine alkaloid sequestering Lepidoptera.

Parsonsine Dilution Calculator

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Parsonsine Molarity Calculator

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Preparing Stock Solutions of Parsonsine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.2753 mL 11.3766 mL 22.7531 mL 45.5063 mL 56.8828 mL
5 mM 0.4551 mL 2.2753 mL 4.5506 mL 9.1013 mL 11.3766 mL
10 mM 0.2275 mL 1.1377 mL 2.2753 mL 4.5506 mL 5.6883 mL
50 mM 0.0455 mL 0.2275 mL 0.4551 mL 0.9101 mL 1.1377 mL
100 mM 0.0228 mL 0.1138 mL 0.2275 mL 0.4551 mL 0.5688 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 Parsonsine

Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi.[Pubmed:12706631]

Insect Biochem Mol Biol. 2003 May;33(5):515-23.

Leaf beetles of the genus Platyphora, feeding on plant species containing pyrrolizidine alkaloids of the lycopsamine type, not only sequester these alkaloids and concentrate them in their exocrine defensive secretions, but also specifically process the plant acquired alkaloids. Using P. boucardi as subject, three mechanisms were studied: (i). utilization of host plant alkaloids that are not sequestered per se; (ii). elucidation of the mechanism of the already documented C-7 epimerization of heliotridine O(9)-monoesters; (iii). the specificity of insect catalyzed necine base esterification. P. boucardi does not sequester the triester Parsonsine, the principal alkaloid of its host plant Prestonia portobellensis (Apocynaceae). Beetles fed with a purified mixture of nor-derivatives of Parsonsine, obtained from Parsonsia laevigata, did not sequester the triesters but transformed them by partial degradation into monoesters that are accumulated in the defensive secretions. The mechanism of the previously described transformation of rinderine into intermedine by C-7 epimerization was elucidated by feeding C-7 deuterated heliotrine (3'-methylrinderine). The transformation of heliotrine into epiheliotrine (3'-methylintermedine) catalyzed by P. boucardi is accompanied by complete loss of deuterium, indicating the same mechanism of an oxidation-reduction process via a ketone intermediate as recently demonstrated in a pyrrolizidine alkaloid sequestering lepidopteran. P. boucardi is able to form ester alkaloids from five different necine bases fed as radioactively labeled substrates. However, besides C-7 epimerization the beetles are not able to convert simple necine bases into retronecine. The functional importance of the various alkaloid transformations is discussed in comparison to striking parallels of analogous reactions known from pyrrolizidine alkaloid sequestering Lepidoptera.

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