Lycopsamine

CAS# 10285-07-1

Lycopsamine

Catalog No. BCN1999----Order now to get a substantial discount!

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Quality Control of Lycopsamine

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Chemical structure

Lycopsamine

3D structure

Chemical Properties of Lycopsamine

Cas No. 10285-07-1 SDF Download SDF
PubChem ID 107938 Appearance White-beige powder
Formula C15H25NO5 M.Wt 299.37
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Retronecine 9-(-)-viridiflorate
Solubility Soluble in chloroform
Chemical Name [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
SMILES CC(C)C(C(C)O)(C(=O)OCC1=CCN2C1C(CC2)O)O
Standard InChIKey SFVVQRJOGUKCEG-ZGFBFQLVSA-N
Standard InChI InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,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.

Source of Lycopsamine

1 Amsinckia sp. 2 Anchusa sp. 3 Borago sp. 4 Cryptantha sp. 5 Eupatorium sp. 6 Heliotropium sp. 7 Messerschmidia sp. 8 Symphytum sp.

Biological Activity of Lycopsamine

In vitro

TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound.[Pubmed: 25531790]

Acta Pharm. 2014 Dec;64(4):503-8.

Due to severe toxicity of pyrrolizidine alkaloids, their quantification in medicinal products is very important. The idea of this research was to use retrorsine as a surrogate reference compound instead of Lycopsamine reference or Lycopsamine isolated from comfrey.
METHODS AND RESULTS:
A method for the analysis of Lycopsamine in extracts of comfrey roots was developed and validated, employing thin layer chromatography, derivatisation with Dann-Mattocks reagent followed by densitometric analysis. The new method showed linearity within 0.70 to 7.0 μg of Lycopsamine per application of 10 μL of a solution. It has also been proven to be specific and precise (repeatability RSD 2-4 % within the plate).
CONCLUSIONS:
The method was successfully employed for quantification of Lycopsamine in comfrey root and comfrey root medicinal products such as ointments.

In vivo

The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus).[Pubmed: 26177929]

J Appl Toxicol. 2016 May;36(5):716-25.

Comfrey (Symphytum officinale), a commonly used herb, contains dehydropyrrolizidine alkaloids that, as a group of bioactive metabolites, are potentially hepatotoxic, pneumotoxic, genotoxic and carcinogenic. Consequently, regulatory agencies and international health organizations have recommended comfrey be used for external use only. However, in many locations comfrey continues to be ingested as a tisane or as a leafy vegetable.
METHODS AND RESULTS:
The objective of this work was to compare the toxicity of a crude, reduced comfrey alkaloid extract to purified Lycopsamine and intermedine that are major constituents of S. officinale. Male, California White chicks were orally exposed to daily doses of 0.04, 0.13, 0.26, 0.52 and 1.04 mmol Lycopsamine, intermedine or reduced comfrey extract per kg bodyweight (BW) for 10 days. After another 7 days chicks were euthanized. Based on clinical signs of poisoning, serum biochemistry, and histopathological analysis the reduced comfrey extract was more toxic than Lycopsamine and intermedine.
CONCLUSIONS:
This work suggests a greater than additive effect of the individual alkaloids and/or a more potent toxicity of the acetylated derivatives in the reduced comfrey extract. It also suggests that safety recommendations based on purified compounds may underestimate the potential toxicity of comfrey.

Protocol of Lycopsamine

Structure Identification
Phytochem Anal. 2014 Sep-Oct;25(5):429-38.

Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine.[Pubmed: 24816769]

To investigate methods for the separation of gram-scale quantities of the epimeric dehydropyrrolizidine alkaloids Lycopsamine and intermedine and to compare their NMR spectroscopic data with those of their heliotridine-based analogues echinatine and rinderine.
METHODS AND RESULTS:
Lycopsamine and intermedine were extracted, predominantly as their N-oxides and along with their acetylated derivatives.Examination of the NMR data for Lycopsamine, intermedine and their heliotridine-based analogues echinatine and rinderine allowed for some amendments of literature data and provided useful comparisons for determining relative configurations in monoester dehydropyrrolizidine alkaloids. A similar NMR comparison of Lycopsamine and intermedine with their N-oxides showed the effects of N-oxidation on some key chemical shifts. A levorotatory shift in specific rotation from +3.29° to -1.5° was observed for Lycopsamine when dissolved in ethanol or methanol respectively.
CONCLUSIONS:
A semi-automated flash chromatographic process using boronated soda glass beads was standardised and confirmed as a useful, larger scale preparative approach for separating the epimers Lycopsamine and intermedine.

Lycopsamine Dilution Calculator

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Lycopsamine Molarity Calculator

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Preparing Stock Solutions of Lycopsamine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3403 mL 16.7017 mL 33.4035 mL 66.807 mL 83.5087 mL
5 mM 0.6681 mL 3.3403 mL 6.6807 mL 13.3614 mL 16.7017 mL
10 mM 0.334 mL 1.6702 mL 3.3403 mL 6.6807 mL 8.3509 mL
50 mM 0.0668 mL 0.334 mL 0.6681 mL 1.3361 mL 1.6702 mL
100 mM 0.0334 mL 0.167 mL 0.334 mL 0.6681 mL 0.8351 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 Lycopsamine

Semi-automated separation of the epimeric dehydropyrrolizidine alkaloids lycopsamine and intermedine: preparation of their N-oxides and NMR comparison with diastereoisomeric rinderine and echinatine.[Pubmed:24816769]

Phytochem Anal. 2014 Sep-Oct;25(5):429-38.

INTRODUCTION: The diversity of structure and, particularly, stereochemical variation of the dehydropyrrolizidine alkaloids can present challenges for analysis and the isolation of pure compounds for the preparation of analytical standards and for toxicology studies. OBJECTIVE: To investigate methods for the separation of gram-scale quantities of the epimeric dehydropyrrolizidine alkaloids Lycopsamine and intermedine and to compare their NMR spectroscopic data with those of their heliotridine-based analogues echinatine and rinderine. METHODS: Lycopsamine and intermedine were extracted, predominantly as their N-oxides and along with their acetylated derivatives, from commercial samples of comfrey (Symphytum officinale) root. Alkaloid enrichment involved liquid-liquid partitioning of the crude methanol extract between dilute aqueous acid and n-butanol, reduction of N-oxides and subsequent continuous liquid-liquid extraction of free base alkaloids into CHCl3 . The alkaloid-rich fraction was further subjected to semi-automated flash chromatography using boronated soda glass beads or boronated quartz sand. RESULTS: Boronated soda glass beads (or quartz sand) chromatography adapted to a Biotage Isolera Flash Chromatography System enabled large-scale separation (at least up to 1-2 g quantities) of Lycopsamine and intermedine. The structures were confirmed using one- and two-dimensional (1) H- and (13) C-NMR spectroscopy. Examination of the NMR data for Lycopsamine, intermedine and their heliotridine-based analogues echinatine and rinderine allowed for some amendments of literature data and provided useful comparisons for determining relative configurations in monoester dehydropyrrolizidine alkaloids. A similar NMR comparison of Lycopsamine and intermedine with their N-oxides showed the effects of N-oxidation on some key chemical shifts. A levorotatory shift in specific rotation from +3.29 degrees to -1.5 degrees was observed for Lycopsamine when dissolved in ethanol or methanol respectively. CONCLUSION: A semi-automated flash chromatographic process using boronated soda glass beads was standardised and confirmed as a useful, larger scale preparative approach for separating the epimers Lycopsamine and intermedine. The useful NMR correlations to stereochemical arrangements within this specific class of dehydropyrrolizidine alkaloid cannot be confidently extrapolated to other similar dehydropyrrolizidine alkaloids. Published 2014. This article is a U.S. Government work and is in the public domain in the USA.

TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound.[Pubmed:25531790]

Acta Pharm. 2014 Dec;64(4):503-8.

Due to severe toxicity of pyrrolizidine alkaloids, their quantification in medicinal products is very important. The idea of this research was to use retrorsine as a surrogate reference compound instead of Lycopsamine reference or Lycopsamine isolated from comfrey. A method for the analysis of Lycopsamine in extracts of comfrey roots was developed and validated, employing thin layer chromatography, derivatisation with Dann-Mattocks reagent followed by densitometric analysis. The new method showed linearity within 0.70 to 7.0 mug of Lycopsamine per application of 10 muL of a solution. It has also been proven to be specific and precise (repeatability RSD 2-4 % within the plate). The method was successfully employed for quantification of Lycopsamine in comfrey root and comfrey root medicinal products such as ointments.

The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus).[Pubmed:26177929]

J Appl Toxicol. 2016 May;36(5):716-25.

Comfrey (Symphytum officinale), a commonly used herb, contains dehydropyrrolizidine alkaloids that, as a group of bioactive metabolites, are potentially hepatotoxic, pneumotoxic, genotoxic and carcinogenic. Consequently, regulatory agencies and international health organizations have recommended comfrey be used for external use only. However, in many locations comfrey continues to be ingested as a tisane or as a leafy vegetable. The objective of this work was to compare the toxicity of a crude, reduced comfrey alkaloid extract to purified Lycopsamine and intermedine that are major constituents of S. officinale. Male, California White chicks were orally exposed to daily doses of 0.04, 0.13, 0.26, 0.52 and 1.04 mmol Lycopsamine, intermedine or reduced comfrey extract per kg bodyweight (BW) for 10 days. After another 7 days chicks were euthanized. Based on clinical signs of poisoning, serum biochemistry, and histopathological analysis the reduced comfrey extract was more toxic than Lycopsamine and intermedine. This work suggests a greater than additive effect of the individual alkaloids and/or a more potent toxicity of the acetylated derivatives in the reduced comfrey extract. It also suggests that safety recommendations based on purified compounds may underestimate the potential toxicity of comfrey.

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