ranunculin

Ranunculin is a glycoside found in many members of the buttercup family, including species of Helleborus, Anemone, Clematis and most commonly Ranunculus. Glycosides are common in plants, where they serve as defense mechanisms against herbivores and microorganisms. When plant cell wall structures are damaged, glycosidase enzymes hydrolyze the inactive glycoside into its components- a sugar and practically any other molecule, which is called the aglycone. Ranunculin is a glucoside, which indicates that glucose is the specific sugar attached its aglycone protoanemonin.

Chemical data

Formula: C11H16O8
Molecular weight: 276.24 g/mol
IUPAC name: (2S)-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2H-furan-5-one
SMILES: C1=CC(=O)O[C@@H]1CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChIKey: TYWXNGXVSZRXNA-NVZSGMJQSA-N
XLogP: -2
Polar surface area: 126 Å²
H-bond donors: 4
H-bond acceptors: 8
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Has part: hydrogen
Mass: 276.084517

Show 4 more facts

found in taxon: Ranunculus japonicus
canonical SMILES: C1=CC(=O)OC1COC2C(C(C(C(O2)CO)O)O)O
chemical formula: C₁₁H₁₆O₈
isomeric SMILES: C1=CC(=O)O[C@@H]1CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Sources (2)

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Encyclopedic overview

3 sections

Contents

Toxicity
Protoanemonin release
References

{{chembox | verifiedrevid = 399427368 | ImageFile = Ranunculin skeletal.svg | IUPACName = (5S)-5-[(β-D-Glucopyranosyloxy)methyl]furan-2(5H)-one | SystematicName = (5S)-5-({[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)furan-2(5H)-one | OtherNames = |Section1= |Section2= |Section3= }}

Excerpted from Wikipedia’s “ranunculin” article, available under the CC BY-SA 4.0 licence.