Structure via PubChem · Public domain (PubChem)
anemonin
Sign in to saveAlso known as (5S,6S)-4,7-dioxadispiro[4.0.46.25]dodeca-1,9-diene-3,8-dione, trans-4,7-Dioxadispiro[4.0.4.2]dodeca-1,9-diene-3,8-dione, trans-anemonin
Anemonin is a dibutenolide natural product found in members of the buttercup family (Ranunculaceae) such as Helleborus niger, Ranunculus bulbosus, R. ficaria, R. sardous, R. sceleratus, and Clematis hirsutissima. Originally isolated in 1792 by M. Heyer, It is the dimerization product of the toxin protoanemonin. One of the likely active agents in plants used in Chinese medicine as an anti-inflammatory and Native American medicine as a horse stimulant, its unique biological properties give it pharmaceutical potential as an anti-inflammatory agent.
Chemical data
- Formula
- C10H8O4
- Molecular weight
- 192.17 g/mol
- IUPAC name
- (5S,6S)-4,7-dioxadispiro[4.0.46.25]dodeca-1,9-diene-3,8-dione
- SMILES
- C1C[C@@]2([C@@]13C=CC(=O)O3)C=CC(=O)O2
- InChIKey
- JLUQTCXCAFSSLD-NXEZZACHSA-N
- XLogP
- 0.4
- Polar surface area
- 52.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 192.042259
Show 5 more facts
- isomeric SMILES
- C1C[C@@]2([C@@]13C=CC(=O)O3)C=CC(=O)O2
- chemical formula
- C₁₀H₈O₄
- canonical SMILES
- C1CC2(C13C=CC(=O)O3)C=CC(=O)O2
- found in taxon
- Prumnopitys andina
- Commons category
- Anemonin
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
7 sectionsContents
- Biosynthetic origins
- Biosynthesis pathway
- Chemical structure and proposed mechanism of formation
- Pharmaceutical potential
- Synthetic preparation
- Kotera Synthesis
- References
Anemonin is a dibutenolide natural product found in members of the buttercup family (Ranunculaceae) such as Helleborus niger, Ranunculus bulbosus, R. ficaria, R. sardous, R. sceleratus, and Clematis hirsutissima. Originally isolated in 1792 by M. Heyer, It is the dimerization product of the toxin protoanemonin. One of the likely active agents in plants used in Chinese medicine as an anti-inflammatory and Native American medicine as a horse stimulant, its unique biological properties give it pharmaceutical potential as an anti-inflammatory agent.
== Biosynthetic origins == Anemonin is a homodimer formed from two protoanemonin subunits. Protoanemonin is formed from the enzymatic cleavage of ranunculin upon crushing plant matter. When a plant from this family is injured, a β-glucosidase cleaves ranunculin, liberating protoanemonin from glucose as a defense mechanism. This butenolide readily dimerizes in aqueous media to form a single cyclodimer.
Excerpted from Wikipedia’s “anemonin” article, available under the CC BY-SA 4.0 licence.