lycopsamine
butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3S)-
Identification
| Name | lycopsamine |
| CAS Number | 10285-07-1 |
| FDA UNII | UER4ET3OHI |
| Molecular Formula | C15 H25 N O5 |
| Molecular Weight | 299.36725000 |
| Nikkaji Number | J15.603E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 2.092e+004 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for lycopsamine usage levels up to | not for fragrance use. |
| Recommendation for lycopsamine flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3S)-
[(7R,8R)-7-
hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
(1R-(1alpha,7(2S*,3S*),7abeta))-(2,3,5,7a-
tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-(1-methylethyl)butanoate
PubMed:
Toxic pyrrolizidine alkaloids provide a warning sign to overuse of the ethnomedicine Arnebia benthamii.
PubMed:
Development and validation of a QuEChERS method coupled to liquid chromatography and high resolution mass spectrometry to determine pyrrolizidine and tropane alkaloids in honey.
PubMed:
Penetration of lycopsamine from a comfrey ointment through human epidermis.
PubMed:
Survey of pyrrolizidine alkaloids in seven varieties of Lappula squarrosa: An alternative source of heart-healthy vegetable oil.
PubMed:
Quantification of pyrrolizidine alkaloids in North American plants and honey by LC-MS: single laboratory validation.
PubMed:
A Validated, Rapid HPLC-ESI-MS/MS Method for the Determination of Lycopsamine.
PubMed:
Pyrrolizidine alkaloids in food and feed on the Belgian market.
PubMed:
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:
Pro-toxic dehydropyrrolizidine alkaloids in the traditional Andean herbal medicine "asmachilca".
PubMed:
Characterization and screening of pyrrolizidine alkaloids and N-oxides from botanicals and dietary supplements using UHPLC-high resolution mass spectrometry.
PubMed:
An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides.
PubMed:
Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae).
PubMed:
TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound.
PubMed:
Development of a fast isocratic LC-MS/MS method for the high-throughput analysis of pyrrolizidine alkaloids in Australian honey.
PubMed:
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:
Profiling of dehydropyrrolizidine alkaloids and their N-oxides in herbarium-preserved specimens of amsinckia species using HPLC-esi(+)MS.
PubMed:
Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed.
PubMed:
Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity.
PubMed:
Pyrrolizidine alkaloids: their occurrence in Spanish honey collected from purple viper's bugloss (Echium spp.).
PubMed:
Dehydropyrrolizidine alkaloids in two Cryptantha species: including two new open chain diesters one of which is amphoteric.
PubMed:
Improved method for isolation of lycopsamine from roots of comfrey (Symphytum officinale).
PubMed:
Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates.
PubMed:
Detection of high levels of pyrrolizidine-N-oxides in the endangered plant Cryptantha crassipes (Terlingua Creek cat's-eye) using HPLC-ESI-MS.
PubMed:
Metabolism, genotoxicity, and carcinogenicity of comfrey.
PubMed:
Pyrrolizidine alkaloids in honey: comparison of analytical methods.
PubMed:
Chiral stationary phases for separation of intermedine and lycopsamine enantiomers from Symphytum uplandicum.
PubMed:
Determination of pyrrolizidine alkaloids in comfrey by liquid chromatography-electrospray ionization mass spectrometry.
PubMed:
Lycopsamine and cumambrin B from Eupatorium maculatum.
PubMed:
Tissue distribution, core biosynthesis and diversification of pyrrolizidine alkaloids of the lycopsamine type in three Boraginaceae species.
PubMed:
Absolute configuration of the creatonotines and callimorphines, two classes of arctiid-specific pyrrolizidine alkaloids.
PubMed:
Major components in the hairpencil secretion of a butterfly, Euploea mulciber (Lepidoptera, Danaidae): their origins and male behavioral responses to pyrrolizidine alkaloids.
PubMed:
Differential utilization of pyrrolizidine alkaloids by males of a danaid butterfly, Parantica sita, for the production of danaidone in the alar scent organ.
PubMed:
Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura.
PubMed:
Solid-phase extraction and HPLC-MS profiling of pyrrolizidine alkaloids and their N-oxides: a case study of Echium plantagineum.
PubMed:
On-line structure characterization of pyrrolizidine alkaloids in Onosma stellulatum and Emilia coccinea by liquid chromatography-ion-trap mass spectrometry.
PubMed:
Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults.
PubMed:
Pyrrolizidine alkaloids from Lithospermum canescens Lehm.
PubMed:
Biochemical processing of plant acquired pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi.
PubMed:
Toxic pyrrolyzidine alkaloids from three mongolian plants. a possible risk for cattle poisoning.
PubMed:
Pyrrolizidine alkaloids in Pulmonaria obscura.
PubMed:
Dual chemical sequestration: a key mechanism in transitions among ecological specialization.
PubMed:
Sequestration, metabolism and partial synthesis of tertiary pyrrolizidine alkaloids by the neotropical leaf-beetle Platyphora boucardi.
PubMed:
Pyrrolizidine alkaloids from Ageratum houstonianum Mill.
PubMed:
Pyrrolizidine alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae).
PubMed:
Pyrrolizidine alkaloids from Heliotropium megalanthum.
PubMed:
Preparative separation of pyrrolizidine alkaloids by high-speed counter-current chromatography.
PubMed:
Stereochemical inversion of pyrrolizidine alkaloids byMechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance.
PubMed:
Pyrrolizidine alkaloids in the arctiid mothHyalurga syma.
PubMed:
Investigation into the Presence of Pyrrolizidine Alkaloids in Eupatorium cannabinum by Means of Positive and Negative Ion Chemical Ionization GC-MS.
PubMed:
Synthesis of pyrrolizidine alkaloids indicine, intermedine, lycopsamine, and analogues and their N-oxides. Potential antitumor agents.
PubMed:
Pyrrolizidine alkaloids from Symphytum officinale L. and their percutaneous absorption in rats.
PubMed:
[II1: TLC and HPLC-Analysis of Pyrrolizidine-N-oxid Alkaloids of Symphyti Radix].