anemonin

Also 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.

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

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Encyclopedic overview

7 sections

Contents

Biosynthetic origins
Biosynthesis pathway
Chemical structure and proposed mechanism of formation
Pharmaceutical potential
Synthetic preparation
Kotera Synthesis
References

== 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.