Tutin (toxin)

Tutin

Clinical data
ATC code	none
Identifiers
IUPAC name 2a,3a-epoxy- 3a,4a,5,6,7,7a-hexahydro- 3aα,6β,7β-trihydroxy- 5α-isopropyl- 7aα-methylspiro (indan-1,2'-oxirane)- γ-lactone
CAS Number	2571-22-4 Y
PubChem CID	75729
ChemSpider	10252021
CompTox Dashboard (EPA)	DTXSID30180400
ECHA InfoCard	100.236.780
Chemical and physical data
Formula	C15H18O6
Molar mass	294.299 g/mol g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=C)[C@@H]1[C@@H]2[C@H]([C@]3([C@@]4(CO4)[C@H]5[C@@H]([C@]3([C@H]1C(=O)O2)O)O5)C)O
InChI InChI=1S/C15H18O6/c1-5(2)6-7-12(17)20-8(6)9(16)13(3)14(4-19-14)10-11(21-10)15(7,13)18/h6-11,16,18H,1,4H2,2-3H3/t6-,7+,8+,9+,10+,11-,13-,14+,15-/m0/s1 Key:CCAZWUJBLXKBAY-ULZPOIKGSA-N
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Tutin is a poisonous plant derivative found in New Zealand tutu plants (several species in the Coriaria genus). It acts as a potent antagonist of the glycine receptor, and has powerful convulsant effects. It is used in scientific research into the glycine receptor. It is sometimes associated with outbreaks of toxic honey poisoning when bees feed on honeydew exudate from the sap-sucking passionvine hopper (Scolypopa australis) insect, when the vine hoppers have been feeding on the sap of tutu bushes. Toxic honey is a rare event and is more likely to occur when comb honey is eaten directly from a hive that has been harvesting honeydew from passionvine hoppers feeding on tutu plants.