Tutin | CAS:2571-22-4 | Manufacturer ChemFaces

Tutin

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Description:

Tutin in honey, is a plant-derived neurotoxin.

In vitro:

J Nat Prod. 2015 Jun 26;78(6):1363-9.

Sweet Poisons: Honeys Contaminated with Glycosides of the Neurotoxin Tutin.[Pubmed: 25993882]

Poisonings due to consumption of honeys containing plant toxins have been reported widely. One cause is the neurotoxin Tutin, an oxygenated sesquiterpene picrotoxane, traced back to honeybees (Apis mellifera) collecting honeydew produced by passionvine hoppers (Scolypopa australis) feeding on sap of the poisonous shrub tutu (Coriaria spp.). However, a pharmacokinetic study suggested that unidentified conjugates of Tutin were also present in such honeys.
METHODS AND RESULTS:
We now report the discovery, using ion trap LC-MS, of two Tutin glycosides and their purification and structure determination as 2-(β-d-glucopyranosyl)Tutin (4) and 2-[6'-(α-d-glucopyranosyl)-β-d-glucopyranosyl]Tutin (5). These compounds were used to develop a quantitative triple quadrupole LC-MS method for honey analysis, which showed the presence of Tutin (3.6 ± 0.1 μg/g honey), hyenanchin (19.3 ± 0.5), Tutin glycoside (4) (4.9 ± 0.4), and Tutin diglycoside (5) (4.9 ± 0.1) in one toxic honey. The ratios of 4 and 5 to Tutin varied widely in other Tutin-containing honeys.
CONCLUSIONS:
The glycosidation of Tutin may represent detoxification by one or both of the insects involved in the food chain from plant to honey.

In vivo:

Food Chem Toxicol. 2014 Oct;72:234-41.

Human pharmacokinetic study of tutin in honey; a plant-derived neurotoxin.[Pubmed: 25084484]

Over the last 150 years a number of people in New Zealand have been incapacitated, hospitalised, or died from eating honey contaminated with Tutin, a plant-derived neurotoxin.
METHODS AND RESULTS:
To investigate the basis of this variability a pharmacokinetic study was undertaken in which 6 healthy males received a single oral dose of Tutin-containing honey giving a Tutin dose of 1.8 μg/kg body weight. The serum concentration-time curve for all volunteers exhibited two discrete peaks with the second and higher level occurring at approximately 15 h post-dose. Two subjects reported mild, transient headache at a time post-dose corresponding to maximum Tutin concentrations. There were no other signs or symptoms typical of Tutin intoxication such as nausea, vomiting, dizziness or seizures. Pharmacokinetic analysis using a two-site absorption model resulted in a good fit to the observed concentration data.
CONCLUSIONS:
A novel analytical method subsequently revealed the presence of glycoside conjugates of Tutin in addition to unconjugated Tutin in honey. These pharmacokinetic data will be important to better define a safe maximum Tutin concentration in honey.

Tutin Description

Source:	The herbs of Coriaria nepalensis Wall.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Product Name	Tutin
Price:
CAS No.:	2571-22-4
Catalog No.:	CFN98289
Molecular Formula:	C₁₅H₁₈O₆
Molecular Weight:	294.3 g/mol
Purity:	>=98%
Type of Compound:	Sesquiterpenoids
Physical Desc.:	Powder
Source:	The herbs of Coriaria nepalensis Wall.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Neurotoxin Compound Library Sesquiterpenoids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.3979 mL	16.9895 mL	33.9789 mL	67.9579 mL	84.9473 mL
5 mM	0.6796 mL	3.3979 mL	6.7958 mL	13.5916 mL	16.9895 mL
10 mM	0.3398 mL	1.6989 mL	3.3979 mL	6.7958 mL	8.4947 mL
50 mM	0.068 mL	0.3398 mL	0.6796 mL	1.3592 mL	1.6989 mL
100 mM	0.034 mL	0.1699 mL	0.3398 mL	0.6796 mL	0.8495 mL

CFN98470	Corianin	35481-77-7	294.3	C₁₅H₁₈O₆
CFN99091	13-O-Acetylcorianin	108887-44-1	336.3	C₁₇H₂₀O₇
CFN98289	Tutin	2571-22-4	294.3	C₁₅H₁₈O₆
CFN98329	2-O-Acetyltutin	2749-28-2	336.3	C₁₇H₂₀O₇
CFN97480	Coriatin	91653-75-7	296.3	C₁₅H₂₀O₆
CFN96743	6-O-Acetylcoriatin	1432063-63-2	338.35	C₁₇H₂₂O₇
CFN99894	Isohyenanchin	19417-00-6	312.3	C₁₅H₂₀O₇