Ranunculin

Ranunculin

Names
IUPAC name (5S)-5-[(β-D-Glucopyranosyloxy)methyl]furan-2(5H)-one
Systematic IUPAC name (5S)-5-({[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)furan-2(5H)-one
Identifiers
CAS Number	644-69-9  Y
3D model (JSmol)	Interactive image
ChemSpider	390250  Y
ECHA InfoCard	100.010.384
PubChem CID	441581
UNII	IBP7446K1O  Y
CompTox Dashboard (EPA)	DTXSID40982977
InChI InChI=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 Y Key: TYWXNGXVSZRXNA-NVZSGMJQSA-N Y 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 Key: TYWXNGXVSZRXNA-NVZSGMJQBP
SMILES C1=CC(=O)OC1COC2C(C(C(C(O2)CO)O)O)O
Properties
Chemical formula	C11H16O8
Molar mass	276.241 g·mol−1
Melting point	141 to 142 °C (286 to 288 °F; 414 to 415 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

Ranunculin is a glycoside found in many members of the buttercup family, including species of Helleborus, Anemone, Clematis and most commonly Ranunculus. ^[1] 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. ^{[2] [3]}

Protoanemonin release

	ranunculin
↓ – glucose	(plant wounded, aglycone release)
	protoanemonin

References

1. Bai, Yili; Benn, Michael; Majak, Walter; McDiamid, Ruth (August 15, 1996). "Extraction and HPLC Determination of Ranunculin in Species of the Buttercup Family". Journal of Agricultural and Food Chemistr. 44 (8): 2235–2238. doi:10.1021/jf950626m . Retrieved March 28, 2025.
2. Berger, Artur; Wachter, Helmut, eds. (1998). Hunnius Pharmazeutisches Wörterbuch (in German) (8 ed.). Walter de Gruyter Verlag. ISBN   3-11-015793-4.
3. Moriarty, Robert; Romain, C; Karle, I; Karle, J (July 1, 1965). "The Structure of Anemonin". Journal of the American Chemical Society. 87 (14): 3251–3252. doi:10.1021/ja01092a047 . Retrieved April 12, 2025.