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MedKoo Cat#: 462679 | Name: Tutin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tutin is a poisonous plant derivative found in New Zealand tutu plants. 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 insect, when the vine hoppers have been feeding on the sap of tutu bushes.

Chemical Structure

Tutin
Tutin
CAS#2571-22-4

Theoretical Analysis

MedKoo Cat#: 462679

Name: Tutin

CAS#: 2571-22-4

Chemical Formula: C15H18O6

Exact Mass: 294.1103

Molecular Weight: 294.30

Elemental Analysis: C, 61.22; H, 6.17; O, 32.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Toot poison; Tutine; Tutu;
IUPAC/Chemical Name
(1a'S,1b'R,2R,2'S,5'R,6'S,6a'R,7a'R,8'R)-1b',6'-dihydroxy-6a'-methyl-8'-(prop-1-en-2-yl)hexahydrospiro[oxirane-2,7'-[2,5]methanooxireno[2',3':3,4]cyclopenta[1,2-d]oxepin]-3'(2'H)-one
InChi Key
CCAZWUJBLXKBAY-ULZPOIKGSA-N
InChi Code
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
SMILES Code
CC([C@@H]1[C@H]2OC([C@@H]1[C@@]3([C@H]4O[C@H]4[C@@]5([C@@]3([C@@H]2O)C)CO5)O)=O)=C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 294.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Watkins OC, Joyce NI, Gould N, Perry NB. Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism. J Nat Prod. 2018 Apr 27;81(4):1116-1120. doi: 10.1021/acs.jnatprod.8b00120. Epub 2018 Mar 5. PMID: 29504746. 2: Fields BA, Reeve J, Bartholomaeus A, Mueller U. Human pharmacokinetic study of tutin in honey; a plant-derived neurotoxin. Food Chem Toxicol. 2014 Oct;72:234-41. doi: 10.1016/j.fct.2014.07.032. Epub 2014 Jul 30. PMID: 25084484. 3: Zhou H, Zheng Y, Tang YH. [Tutin-induced epileptiform discharge of CA1 pyramidal cells in rat hippocampal slices]. Sheng Li Xue Bao. 2004 Jun 25;56(3):341-6. Chinese. PMID: 15224147. 4: Fuentealba J, Muñoz B, Yévenes G, Moraga-Cid G, Pérez C, Guzmán L, Rigo JM, Aguayo LG. Potentiation and inhibition of glycine receptors by tutin. Neuropharmacology. 2011 Feb-Mar;60(2-3):453-9. doi: 10.1016/j.neuropharm.2010.10.023. Epub 2010 Oct 31. PMID: 21044637. 5: Larsen L, Joyce NI, Sansom CE, Cooney JM, Jensen DJ, Perry NB. Sweet Poisons: Honeys Contaminated with Glycosides of the Neurotoxin Tutin. J Nat Prod. 2015 Jun 26;78(6):1363-9. doi: 10.1021/acs.jnatprod.5b00241. Epub 2015 May 21. PMID: 25993882. 6: Beasley M, Hood D, Anderson P, Reeve J, Slaughter RJ. Poisoning due to tutin in honey-a report of an outbreak in New Zealand. N Z Med J. 2018 Apr 13;131(1473):59-71. PMID: 29649198. 7: Fuentealba J, Guzmán L, Manríquez-Navarro P, Pérez C, Silva M, Becerra J, Aguayo LG. Inhibitory effects of tutin on glycine receptors in spinal neurons. Eur J Pharmacol. 2007 Mar 15;559(1):61-4. doi: 10.1016/j.ejphar.2006.12.018. Epub 2007 Jan 17. PMID: 17303114. 8: Zhou H, Tang YH, Zheng Y. A new rat model of acute seizures induced by tutin. Brain Res. 2006 May 30;1092(1):207-13. doi: 10.1016/j.brainres.2006.03.081. Epub 2006 May 3. PMID: 16674929. 9: Okuda T, Yoshida T. The correlation of coriamyrtin and tutin, and their absolute configurations. Chem Pharm Bull (Tokyo). 1967 Dec;15(12):1955-65. doi: 10.1248/cpb.15.1955. PMID: 5590701. 10: Jiang YQ, Xu ML, Chen XM. [Effects of microinjection of tutin into the nucleus tractus solitarius on the phrenic nerve discharge in rabbits]. Sheng Li Xue Bao. 1990 Jun;42(3):295-301. Chinese. PMID: 2082474. 11: Curtis DR, Davies J, Game CJ, Johnston GA, McCulloch RM. Central actions of shikimin and tutin. Brain Res. 1973 Dec 7;63:419-23. doi: 10.1016/0006-8993(73)90116-9. PMID: 4148744. 12: Pérez C, Becerra J, Manríquez-Navarro P, Aguayo LG, Fuentealba J, Guzmán JL, Joseph-Nathan P, Jiménez V, Muñoz MA, Silva M. Inhibitory activities on mammalian central nervous system receptors and computational studies of three sesquiterpene lactones from Coriaria ruscifolia subsp. ruscifolia. Chem Pharm Bull (Tokyo). 2011;59(2):161-5. doi: 10.1248/cpb.59.161. PMID: 21297293. 13: Wang J, Xu M, Li G, Chen X. [Nerve tissue morphological study of tutin microinjection into pontine NPBM in two hours]. Hua Xi Yi Ke Da Xue Xue Bao. 2002 Jan;33(1):54-7. Chinese. PMID: 12599428. 14: Nistri A, Constanti A, Quilliam JP. Letter: Central inhibition, G.A.B.A., and tutin. Lancet. 1974 May 18;1(7864):996-7. doi: 10.1016/s0140-6736(74)91311-7. PMID: 4133689. 15: Jiang Y, Xu M, Wu L, Chen X. [Effects of microinjection of tutin into nucleus tractus solitarius region on the morphology of neural tissue of this area in rabbit]. Hua Xi Yi Ke Da Xue Xue Bao. 1991 Mar;22(1):35-8. Chinese. PMID: 1685470. 16: Şenol FS, Yilmaz G, Şener B, Koyuncu M, Orhan I. Preliminary screening of acetylcholinesterase inhibitory and antioxidant activities of Anatolian Heptaptera species. Pharm Biol. 2010 Mar;48(3):337-41. doi: 10.3109/13880200903133837. PMID: 20645823. 17: Yuan DJ. [Clinical observations on the effects of Lactoni Coriariae and Tutin in the treatment of schizophrenia (report of 140 cases) (author's transl)]. Zhonghua Shen Jing Jing Shen Ke Za Zhi. 1979;12(4):196-200. Chinese. PMID: 555383. 18: Moghadamtousi SZ, Kamarudin MN, Chan CK, Goh BH, Kadir HA. Phytochemistry and biology of Loranthus parasiticus Merr, a commonly used herbal medicine. Am J Chin Med. 2014;42(1):23-35. doi: 10.1142/S0192415X14500025. PMID: 24467533. 19: Wang J, Xu M, Chen Z, Chen X. [Respiratory effects of tutin microinjection into NPBM of rabbits]. Hua Xi Yi Ke Da Xue Xue Bao. 1993 Jun;24(2):152-5. Chinese. PMID: 8244291. 20: Kudo Y, Niwa H, Tanaka A, Yamada K. Actions of picrotoxinin and related compounds on the frog spinal cord: the role of a hydroxyl-group at the 6-position in antagonizing the actions of amino acids and presynaptic inhibition. Br J Pharmacol. 1984 Feb;81(2):373-80. doi: 10.1111/j.1476-5381.1984.tb10088.x. PMID: 6608389; PMCID: PMC1986894.