Ptaquiloside

Ptaquiloside
Names
	IUPAC name (2R,3aR,7S,7aR)-7-Hydroxy-2,5,7-trimethyl-3a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-spiro[3,7a-dihydro-2H-indene-6,1'-cyclopropane]-1-one
Identifiers
CAS Number	87625-62-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3632862
ChEBI	CHEBI:82527 ;
ChemSpider	10312775 ;
KEGG	C19515 ;
PubChem CID	13962857;
UNII	F0MN9S5699 ;
CompTox Dashboard (EPA)	DTXSID20892005 ;
	InChI InChI=1S/C20H30O8/c1-9-6-20(28-17-15(25)14(24)13(23)11(8-21)27-17)7-10(2)19(4-5-19)18(3,26)16(20)12(9)22/h7,9,11,13-17,21,23-26H,4-6,8H2,1-3H3/t9-,11-,13-,14+,15-,16-,17+,18+,20-/m1/s1;
	SMILES C[C@@H]1C[C@]2(C=C(C3(CC3)[C@@]([C@H]2C1=O)(C)O)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O;
Properties
Chemical formula	C20H30O8
Molar mass	398.452 g·mol−1
Melting point	85 to 89 °C (185 to 192 °F; 358 to 362 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ptaquiloside is a norsesquiterpene glucoside produced by bracken ferns (majorly Pteridium aquilinum) during metabolism. It is identified to be the main carcinogen of the ferns and to be responsible for their biological effects, such as haemorrhagic disease and bright blindness in livestock and oesophageal, gastric cancer in humans. Ptaquiloside has an unstable chemical structure and acts as a DNA alkylating agent under physiological conditions. It was first isolated and characterized by Yamada and co-workers in 1983.

The pure form ptaquiloside is a colorless amorphous compound. It is readily soluble in water and fairly soluble in ethyl acetate. Except in the plants, ptaquiloside has been detected in the milk and meat of affected livestock, as well as in the underground water and dry soil around bracken fern vegetation. The prevalence of ptaquiloside in daily sources along with its carcinogenic effects make it an increasing biological hazard in modern days.