Viridiflorine

CAS# 551-57-5

Viridiflorine

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Chemical structure

Viridiflorine

3D structure

Chemical Properties of Viridiflorine

Cas No. 551-57-5 SDF Download SDF
PubChem ID 6453144 Appearance Powder
Formula C15H27NO4 M.Wt 285.38
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1R,8S)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
SMILES CC(C)C(C(C)O)(C(=O)OCC1CCN2C1CCC2)O
Standard InChIKey BWQSLRZZOVFVHJ-ABHRYQDASA-N
Standard InChI InChI=1S/C15H27NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h10-13,17,19H,4-9H2,1-3H3/t11-,12-,13-,15-/m0/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 Viridiflorine

Structure Identification
Phytochemistry,1990,29(9):2871-2872.

Pyrrolizidine alkaloids from Cynoglossum germanicum[Reference: WebLink]


METHODS AND RESULTS:
Dried leaves and fruits from cultivated Cynoglossum germanicum plants were found to contain the saturated pyrrolizidine alkaloid, Viridiflorine, along with a small amount of the unsaturated alkaloid echinatine or a closely related isomer.

Phytochemistry,1992,31(7):2513-2518.

Pyrrolizidine alkaloids from Amsinckia[Reference: WebLink]


METHODS AND RESULTS:
In conjunction with a chemosystematic analysis of the genus Amsinckia, the novel pyrrolizidine alkaloids tessellatine and 3′,7-diacetylintermedine were isolated and structurally elucidated by chromatographic (GC and TLC) and spectroscopic (mass, and 1H and 13C NMR) experiments. The 1H and 13C NMR spectra of Viridiflorine are also discussed in detail.

Viridiflorine Dilution Calculator

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Viridiflorine Molarity Calculator

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Preparing Stock Solutions of Viridiflorine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5041 mL 17.5205 mL 35.041 mL 70.082 mL 87.6025 mL
5 mM 0.7008 mL 3.5041 mL 7.0082 mL 14.0164 mL 17.5205 mL
10 mM 0.3504 mL 1.752 mL 3.5041 mL 7.0082 mL 8.7602 mL
50 mM 0.0701 mL 0.3504 mL 0.7008 mL 1.4016 mL 1.752 mL
100 mM 0.035 mL 0.1752 mL 0.3504 mL 0.7008 mL 0.876 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 Viridiflorine

Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): their origins and male behavioral responses to pyrrolizidine alkaloids.[Pubmed:16979653]

J Insect Physiol. 2006 Oct;52(10):1043-53.

Two compounds, 9,10-epoxytetrahydroedulan (ET) and Viridiflorine beta-lactone (VL), were identified as major components from the hairpencils of field-caught males of a danaid butterfly, Euploea mulciber. By contrast, laboratory-reared males entirely lacked VL, but possessed a significant quantity of ET. Various feeding experiments with larvae and indoor adult males strongly suggested that ET is biosynthesized de novo only after eclosion from nutrients ingested during the larval development. Since VL was suspected to be derived from pyrrolizidine alkaloids (PAs) acquired as an adult, tests for feeding response to and oral administration of four PAs (a 4:1 mixture of intermedine/lycopsamine, heliotrine, monocrotaline, and retronecine) were conducted. When the tarsi or proboscis were stimulated with PA solutions, males showed positive feeding responses (proboscis extension and sucking movements) to intermedine/lycopsamine, heliotrine, and retronecine in decreasing order of responsiveness, thereby providing evidence that male adults are endowed with taste receptor(s) specific to PAs on the legs as well as on the proboscis. Differently from gustatory responsiveness, only males fed with intermedine/lycopsamine produced a significant quantity of VL (ca. 35 microg/male), whereas those that ingested heliotrine or monocrotaline hydrochloride produced traces of VL (<0.18 microg/male). Uptake of retronecine did not lead to VL formation at all. In behavioral bioassays to test the attractivity of PAs to males, all individuals tested were attracted exclusively to intermedine/lycopsamine. This shows that certain PA(s) per se serve as attractant(s) for males in locating PA sources, and further suggests that in the field, males will seek particular PA(s) that are indispensable as precursors for the efficient biosynthesis of VL.

Pyrrolizidine alkaloid composition of three Chinese medicinal herbs, Eupatorium cannabinum, E. japonicum and Crotalaria assamica.[Pubmed:1471612]

Am J Chin Med. 1992;20(3-4):281-8.

The pyrrolizidine alkaloid composition of three Chinese herbs, "pei lan", "cheng gan cao" and "zi xiao rong," identified respectively as Eupatorium cannabinum, Eupatorium japonicum (Compositae) and Crotalaria assamica (Leguminosae), were studied by fast atom bombardment mass spectrometry and gas chromatography-electron impact mass spectrometry. Viridiflorine, cynaustraline, amabiline, supinine, echinatine, rinderine and isomers of these alkaloids were found in the Eupatorium species. Monocrotaline was the only pyrrolizidine alkaloid detected in the Crotalaria species.

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