(-)-aspidospermine
Identification
| Name | (-)-aspidospermine |
| CAS Number | 466-49-9 |
| FDA UNII | U1475W62Q5 |
| Molecular Formula | C22 H30 N2 O2 |
| Molecular Weight | 354.49350000 |
| Nikkaji Number | J11.323I |
| Beilstein | 0048882 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 4.207 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 (-)-aspidospermine usage levels up to | not for fragrance use. |
| Recommendation for (-)-aspidospermine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
aspidospermidine, 1-acetyl-17-methoxy- (8CI,9CI)
PubMed:
Divergent Asymmetric Total Synthesis of (+)-Vincadifformine, (-)-Quebrachamine, (+)-Aspidospermidine, (-)-Aspidospermine, (-)-Pyrifolidine, and Related Natural Products.
PubMed:
Identification of an aspidospermine derivative from borage extract as an anti-amyloid compound: A possible link between protein aggregation and antimalarial drugs.
PubMed:
Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications.
PubMed:
Cytotoxicity, genotoxicity and mechanism of action (via gene expression analysis) of the indole alkaloid aspidospermine (antiparasitic) extracted from Aspidosperma polyneuron in HepG2 cells.
PubMed:
Cytotoxic eburnamine-aspidospermine type bisindole alkaloids from Bousigonia mekongensis.
PubMed:
Catalytic enantioselective and divergent total synthesis of (+)-10-oxocylindrocarpidine, (+)-cylindrocarpidine, (-)-N-acetylcylindrocarpinol, and (+)-aspidospermine.
PubMed:
Angustifonines A and B, cytotoxic bisindole alkaloids from Bousigonia angustifolia.
PubMed:
Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine.
PubMed:
Stereoselective formation of fused tricyclic amines from acyclic aldehydes by a cascade process involving condensation, cyclization, and dipolar cycloaddition.
PubMed:
The use of natural product scaffolds as leads in the search for trypanothione reductase inhibitors.
PubMed:
Efficient synthetic approaches to the common scaffold of indole alkaloids.
PubMed:
Highly efficient synthesis of tricyclic amines by a cyclization/cycloaddition cascade: total syntheses of aspidospermine, aspidospermidine, and quebrachamine.
PubMed:
Formal synthesis of aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums.
PubMed:
Revisiting a classic approach to the Aspidosperma alkaloids: an intramolecular Schmidt reaction mediated synthesis of (+)-aspidospermidine.
PubMed:
Total synthesis of (-)-aspidospermine via diastereoselective ring-closing olefin metathesis.
PubMed:
Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring.
PubMed:
Antiplasmodial activity of aspidosperma indole alkaloids.
PubMed:
Alkaloids from Aspidosperma species from Bolivia.
PubMed:
Alkaloids from leaves and stems of Vallesia glabra.
PubMed:
Isolation and biological activity of aspidospermine and quebrachamine from an Aspidosperma tree source.
PubMed:
New compounds with cytotoxic and antitumor effects. Part 6: Monomeric indole alkaloids of vinca minor L. and their effect on P388 cells.
PubMed:
Alkaloids from Roots of Strempeliopsis strempelioides - Structures of Strempeliopine and Strempeliopidine1.
PubMed:
Microbial transformation of aspidospermine.
PubMed:
Biological and phytochemical evaluation of plants. XI. Isolation of aspidospermine, quebrachidine, rhazinilam, (-)-pyrifolidine, and akuammidine from Aspidosperma quebracho-blanco (Apocynaceae).
PubMed:
The synthesis of a racemic stereoisomer of aspidospermine.
PubMed:
The stereochemistry of intermediates in the total synthesis of dl-aspidospermine.
PubMed:
The absolute configuration of (-)-aspidospermine.
PubMed:
Total synthesis of aspidospermine.
PubMed:
[Determination of the absolute configuration of alkaloids of the aspidospermine group by means of optical comparison with alkaloids of the strychnine group].
PubMed:
A note on the pharmacology of aspidospermine.
PubMed:
The constitution of aspidospermine.
PubMed:
Aspidospermine.