{{chembox | verifiedrevid = 399427368 | ImageFile = Ranunculin skeletal.svg | IUPACName = (5''S'')-5-[(β-<small>D</small>-Glucopyranosyloxy)methyl]furan-2(5''H'')-one | SystematicName = (5''S'')-5-({[(2''R'',3''R'',4''S'',5''S'',6''R'')-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)furan-2(5''H'')-one | OtherNames = |Section1={{Chembox Identifiers | CASNo = 644-69-9 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = IBP7446K1O | PubChem = 441581 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 390250 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1 | SMILES = C1=CC(=O)OC1COC2C(C(C(C(O2)CO)O)O)O | InChI = 1/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1 | InChIKey = TYWXNGXVSZRXNA-NVZSGMJQBP | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = TYWXNGXVSZRXNA-NVZSGMJQSA-N }} |Section2={{Chembox Properties | C=11 | H=16 | O=8 | Appearance = | Density = | MeltingPtC = 141 to 142 | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | FlashPt = | AutoignitionPt = }} }}
'''Ranunculin''' is a glycoside found in many members of the buttercup family, including species of Helleborus, Anemone, Clematis and most commonly Ranunculus.<ref name="Bai"/> 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.
== Toxicity == Ranunculin is very stable in acidic medium and fresh plant tissues, but in alkaline solution or damaged plant cells is hydrolyzed into the unstable toxin protoanemonin and glucose.<ref name="Hunnius"/><ref name="Moriarty"/>
=== Protoanemonin release === {| style="text-align:center" | 250px || ranunculin |- | ↓ – glucose || (plant wounded, aglycone release) |- | 150px|| protoanemonin |}
==References== <references>
<ref name="Bai">{{cite journal |last1=Bai |first1=Yili |last2=Benn |first2=Michael |last3=Majak |first3=Walter |last4=McDiamid |first4=Ruth |title=Extraction and HPLC Determination of Ranunculin in Species of the Buttercup Family |journal=Journal of Agricultural and Food Chemistry |date=August 15, 1996 |volume=44 |issue=8 |pages=2235-2238 |doi=10.1021/jf950626m |url=https://doi.org/10.1021/jf950626m |access-date=March 28, 2025|url-access=subscription }}</ref> <ref name="Hunnius">{{cite book|editor1-first=Artur|editor1-last=Berger|editor2-first=Helmut|editor2-last=Wachter|title=Hunnius Pharmazeutisches Wörterbuch|edition=8|publisher=Walter de Gruyter Verlag|year=1998|language=German|isbn=3-11-015793-4}}</ref> <ref name="Moriarty">{{cite journal |last1=Moriarty |first1=Robert |last2=Romain |first2=C |last3=Karle |first3=I |last4=Karle |first4=J |title=The Structure of Anemonin |journal=Journal of the American Chemical Society |date=July 1, 1965 |volume=87 |issue=14 |pages=3251-3252 |doi=10.1021/ja01092a047 |url=https://doi.org/10.1021/ja01092a047 |access-date=April 12, 2025|url-access=subscription }}</ref>
</references>
Category:Glucosides Category:Furanones Category:Ranunculaceae