tutin
(1aS,1bR,2S,5R,6S,6aR,7R,7aR,8R)-1b,6-dihydroxy-6a-methyl-8-(prop-1-en-2-yl)hexahydrospiro[2,5-methanooxireno[3,4]cyclopenta[1,2-d]oxepine-7,2'-oxiran]-3(2H)-one
 
Notes:
neurotoxin found in coriaria shrubs; hyenanchin is the hydroxy derivative.
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CAS Number: 2571-22-4Picture of molecule3D/inchi
FDA UNII: B69P754702
Nikkaji Web: J9.962G
XlogP3-AA: -0.50 (est)
Molecular Weight: 294.30366000
Formula: C15 H18 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 550.90 °C. @ 760.00 mm Hg (est)
Flash Point: 415.00 °F. TCC ( 212.60 °C. ) (est)
logP (o/w): 1.380 (est)
Soluble in:
 water, 1.90E+04 mg/L @ 10 °C (exp)
 water, 7988 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Coompo
For experimental / research use only.
Tutin from Plants ≥96%
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
unreported-guinea pig LDLo  2 mg/kg
BEHAVIORAL: COMA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 2, Pg. 73, 1910.

intraperitoneal-mouse LD50  3 mg/kg
Journal of Medicinal Chemistry. Vol. 11, Pg. 729, 1968.

intravenous-rabbit LD50  1244 ug/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

unreported-rabbit LDLo  1666 ug/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: COMA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 2, Pg. 73, 1910.

Dermal Toxicity:
subcutaneous-mouse LD50 3613 ug/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

subcutaneous-rabbit LD50 1521 ug/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 2, 1940.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for tutin usage levels up to:
 not for fragrance use.
 
Recommendation for tutin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 75729
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0002571224
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References:
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 75729
Pubchem (sid): 135032793
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C09570
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
(1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-12-isopropenyl-7-methyl-11H-spiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxiran]-11-one
(1aS,1bR,2S,5R,6S,6aR,7R,7aR,8R)-1b,6-dihydroxy-6a-methyl-8-(prop-1-en-2-yl)hexahydrospiro[2,5-methanooxireno[3,4]cyclopenta[1,2-d]oxepine-7,2'-oxiran]-3(2H)-one
(1S,2R,3S,5R,6R,7R,8S,9R,12R)-2,8-dihydroxy-7-methyl-12-(prop-1-en-2-yl)-11H-spiro[4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane-6,2'-oxiran]-11-one
 toot poison
 tutine
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Articles:
PubMed: Human pharmacokinetic study of tutin in honey; a plant-derived neurotoxin.
PubMed: Chimpanzees (Pan troglodytes verus) and their mammalian sympatriates: Mt. Assirik, Niokolo-Koba National Park, Senegal.
PubMed: Phytochemistry and biology of Loranthus parasiticus Merr, a commonly used herbal medicine.
PubMed: Assessment of landscape-scale distribution of sympatric great apes in African rainforests: concurrent use of nest and camera-trap surveys.
PubMed: Uncontrolled donors with controlled reperfusion after sixty minutes of asystole: a novel reliable resource for kidney transplantation.
PubMed: Semisynthesis of N-acyl homoserinelactone derivatives and the antifeedant activity against Mythimna separata.
PubMed: A bitter-sweet tale from the land of milk and honey.
PubMed: Tutu toxicity: three case reports of Coriaria arborea ingestion, review of literature and recommendations for management.
PubMed: [Optimization of kidney transplantation from elderly donors].
PubMed: Sesquiterpenoids and diarylheptanoids from Nidus vespae and their inhibitory effects on nitric oxide production.
PubMed: Inhibitory activities on mammalian central nervous system receptors and computational studies of three sesquiterpene lactones from Coriaria ruscifolia subsp. ruscifolia.
PubMed: Potentiation and inhibition of glycine receptors by tutin.
PubMed: An ethnobotanical survey of medicinal plants in Sivrice (Elazığ-Turkey).
PubMed: Preliminary screening of acetylcholinesterase inhibitory and antioxidant activities of Anatolian Heptaptera species.
PubMed: Investigation of the possible biological activities of a poisonous South African plant; Hyaenanche globosa (Euphorbiaceae).
PubMed: [Parent satisfaction with the Loire Infant Follow-up Team (LIFT) premature and at-risk infant network in the Pays-de-la-Loire area (France)].
PubMed: Effects of Athamanta turbith fruit essential oils on CCl4-induced hepatic failure in mice and their antioxidant properties.
PubMed: Chemical and principal-component analyses of the essential oils of Apioideae taxa (Apiaceae) from central Balkan.
PubMed: The role of Pleistocene refugia and rivers in shaping gorilla genetic diversity in central Africa.
PubMed: Who killed Porthos? Genetic tracking of a gorilla death.
PubMed: Seed protein variations of Salicornia L. and allied taxa in Turkey.
PubMed: Relationship between heavy fuel oil phytotoxicity and polycyclic aromatic hydrocarbon contamination in Salicornia fragilis.
PubMed: Inhibitory effects of tutin on glycine receptors in spinal neurons.
PubMed: A new rat model of acute seizures induced by tutin.
PubMed: Evidence for bioaccumulation of PAHs within internal shoot tissues by a halophytic plant artificially exposed to petroleum-polluted sediments.
PubMed: Gas chromatographic-mass spectrometric method for polycyclic aromatic hydrocarbon analysis in plant biota.
PubMed: The isolation and structure elucidation of a new sesquiterpene lactone from the poisonous plant Coriaria japonica (Coriariaceae).
PubMed: Western gorilla diet: a synthesis from six sites.
PubMed: The epizootiological occurrence of bluetongue in the central Balkans.
PubMed: [Tutin-induced epileptiform discharge of CA1 pyramidal cells in rat hippocampal slices].
PubMed: Mitochondrial DNA phylogeography of western lowland gorillas (Gorilla gorilla gorilla).
PubMed: Phase I trial of concurrent twice-weekly recombinant human interleukin-12 plus low-dose IL-2 in patients with melanoma or renal cell carcinoma.
PubMed: Primates in caves: two new reports of Papio spp.
PubMed: Catastrophic ape decline in western equatorial Africa.
PubMed: Radial variation in sap flow in five laurel forest tree species in Tenerife, Canary Islands.
PubMed: [Nerve tissue morphological study of tutin microinjection into pontine NPBM in two hours].
PubMed: A phase II pilot trial of concurrent biochemotherapy with cisplatin, vinblastine, temozolomide, interleukin 2, and IFN-alpha 2B in patients with metastatic melanoma.
PubMed: Quantitation of trimethyl amine by headspace gas chromatography-mass spectrometry using a base-modified column.
PubMed: [Studies on chemical constituents from the root of Coriaria nepalensis wall (Coriaria sinica Maxim)].
PubMed: Saving the gorillas (Gorilla g. gorilla) and chimpanzees (Pan t. troglodytes) of the Congo Basin.
PubMed: [Diagnostic value of hysterosalpingography in examination of fallopian tubes in infertile women].
PubMed: NOESY on neurotoxins: NMR and conformational assignments of picrotoxins.
PubMed: [Diagnostic value of hysterosalpingography in examination of Fallopian tubes in infertile women].
PubMed: [Ecology and social organization of African tropical forest primates: aid in understanding retrovirus transmission].
PubMed: Initial studies on the contributions of body size and gastrointestinal passage rates to dietary flexibility among gorillas.
PubMed: Cultures in chimpanzees.
PubMed: Fragmented living: Behavioural ecology of primates in a forest fragment in the Lopé Reserve, Gabon.
PubMed: Lowland gorillas and seed dispersal: the importance of nest sites.
PubMed: The primate community of the Lopé Reserve, Gabon: diets, responses to fruit scarcity, and effects on biomass.
PubMed: Actions of picrodendrin antagonists on dieldrin-sensitive and -resistant Drosophila GABA receptors.
PubMed: Filariae from a wild gorilla in Gabon with description of a new species of Mansonella.
PubMed: Intestinal parasites of sympatric gorillas and chimpanzees in the Lopé Reserve, Gabon.
PubMed: A school-based anger management program for developmentally and emotionally disabled high school students.
PubMed: [Respiratory effects of tutin microinjection into NPBM of rabbits].
PubMed: Foraging profiles of sympatric lowland gorillas and chimpanzees in the Lopé Reserve, Gabon.
PubMed: Possible osteomyelitis of skull causes death of a wild lowland gorilla in the Lopé Reserve, Gabon.
PubMed: [Effects of microinjection of tutin into nucleus tractus solitarius region on the morphology of neural tissue of this area in rabbit].
PubMed: [Effects of microinjection of tutin into the nucleus tractus solitarius on the phrenic nerve discharge in rabbits].
PubMed: Simultaneous attack by adult males of a polyspecific troop of monkeys against a crowned hawk eagle.
PubMed: A multivariate analysis of dropout status by length of stay in a rural community mental health center.
PubMed: Contemporary lake transport processes determined from sedimentary records of copper mining activity.
PubMed: 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.
PubMed: The intestinal entodiniomorph ciliates of wild lowland gorillas (Gorilla gorilla gorilla) in Gabon, West Africa.
PubMed: A new intestinal parasitic entodiniomorph ciliate from wild lowland gorillas (Gorilla gorilla gorilla) in Gabon?
PubMed: Reproductive behaviour of wild chimpanzees in the Gombe National Park, Tanzania.
PubMed: [Clinical observations on the effects of Lactoni Coriariae and Tutin in the treatment of schizophrenia (report of 140 cases) (author's transl)].
PubMed: [Nutritional and dietetic problems arising particularly in prolonged corticotherapy].
PubMed: [Physiopathology of diabetic microangiopathy: value of control of the diabetes].
PubMed: [Value of fractionation in diabetology therapy and particularly for glibenclamide].
PubMed: The intestinal parasites of a community of feral chimpanzees, Pan troglodytes schweinfurthii.
PubMed: Tool use in a group of captive chimpanzees I. Escape.
PubMed: [Current results and methods in eradication of typhus fever on the Serbian territory excluding autonomic provinces].
PubMed: [How to advance antidiabetic therapy].
PubMed: Letter: Central inhibition, G.A.B.A., and tutin.
PubMed: Central actions of shikimin and tutin.
PubMed: Chimpanzee copulatory behaviour.
PubMed: Sexual behaviour of group-living adolescent chimpanzees.
PubMed: Chimpanzee dentistry.
PubMed: [Toxic hypoglycemia].
PubMed: [Chronic pancreatitis, diabetes mellitus and specific microangiopathy].
PubMed: [Psychosociologic study of therapeutic constraints in diabetes mellitus].
PubMed: [Psychological consequences of the therapeutic constraints in the diabetic patient (apropos of a survey of 77 cases].
PubMed: [Diabetic retinopathy and insulin therapy].
PubMed: [Can retinopathy be prevented by a more physiological treatment of diabetes?].
PubMed: [Survey on the influence of multiple injections of insulin on the diabetic retinal micro-angiopathy].
PubMed: [For a more physiological treatment of diabetes mellitus. Is it possible to prevent the appearance of angiopathy?].
PubMed: [Diabetes mellitus and chronic pancreatitis].
PubMed: [Specific angiopathy in diabetes secondary to pancreatitis].
PubMed: [Place of hypoglycemic sulfonamides in treatment of steatosis of nutritional origin].
PubMed: [Value of average chain triglycerides in fat malabsorption].
PubMed: [Horton's disease with bilateral eye involvment, cutaneous and lingual necrosis].
PubMed: [Apparently idiopathic bullous dermatosis in a diabetic].
PubMed: [Misleading manifestations of intestinal malabsorption].
PubMed: [Idiopathic bullous eruption in a diabetic].
PubMed: [Study of 41 cases of acute carbon monoxide poisoning with dynamic tests of glycoregulation].
PubMed: The correlation of coriamyrtin and tutin, and their absolute configurations.
PubMed: [Postalcoholic hypoglycemia of the adult. Clinical, biological and physiopathological consideration on 6 cases].
PubMed: [Effects of different diets in obesity].
PubMed: [Disorders of glyco-regulation after portacaval anastomosis: Study of the outcome of carbohydrate metabolism disorders in liver cirrhosis].
PubMed: The central nervous system and carbon monoxide poisoning. I. Clinical data with reference to 20 fatal cases.
PubMed: [Specific angiopathy in diabetes secondary to pancreatitis and hemochromatosis (61 cases)].
PubMed: [Glycoregulation and carbon monoxide coma].
PubMed: [Physiopathological studies of hypoglycemia induced by alcohol (post-alcoholic hypoglycemia)].
PubMed: [Diabetic retinopathy and current concepts of diabetic angiopathy].
PubMed: [Elevation of transaminases during acute respiratory insufficiency].
PubMed: [Apropos of the association of cancer of the kidney, neuromyopathy and hypercalcemia with hypophosphoremia. Discussion of a paraneoplastic hyperparathyroidism].
PubMed: [Electroencephalographic aspects during acute carbon monoxide poisoning and its sequelae].
PubMed: [Diabetes and pancreatopathies].
PubMed: [Thoughts on nonspherocytic chronic congenital hemolytic anemia: apropos of a case].
PubMed: [Intestinal bilharziasis of 1st invasion. Serologic diagnosis. (Apropos of a case)].
PubMed: [Hypereosinophilia in cancer. Considerations apropos of a case in cancer of the kidney].
PubMed: [NUTRITION AND DIET IN 1964].
PubMed: [INFECTIOUS JAUNDICE SECONDARY TO SEPTICEMIA OF URINARY ONSET IN ADULTS].
PubMed: [The heart and hemochromatosis].
PubMed: [ORGANIC PHOSPHORUS POISONING].
PubMed: [THROMBOPENIC PURPURA OF SARCOIDOSIC ORIGIN. REFLECTIONS APROPOS OF A RETROCESSIVE CASE WITHOUT SPLENECTOMY].
PubMed: [THE TREATMENT OF HEMOCHROMATOSIS].
PubMed: [INVESTIGATION ON THE RESULTS OF TREATMENT OF HEMOCHROMATOSIS BY BLOODLETTING].
PubMed: [CHILD GROWTH FROM 0 TO 7 YEARS OF AGE. (MEASUREMENTS OF CHILDREN OF THE PARIS AREA FROM 1953 TO 1962)].
PubMed: [UNSTABLE DIABETES AND ITS TREATMENT].
PubMed: [DIETETICS IN THE TREATMENT OF EDEMA].
PubMed: [Gallbladder neck disease. 54 anatomo-clinical cases without cholelithiasis].
PubMed: [Vitamins in gastroenterology].
PubMed: [Hepatitis and anuria].
PubMed: [Malabsorption syndromes. III. Whipple's disease].
PubMed: [Malabsorption syndromes. II. Secondary steatorrheas caused by malabsorption of the small intestine].
PubMed: [Orthostatic hypotension. (Apropos of a case)].
PubMed: [Acute cholostatic hepatitis].
PubMed: [Polycystic disease of the liver and kidneys].
PubMed: [Metabolic study of a case of Whipple's disease].
PubMed: [Gastroenterology].
PubMed: [Cancer of the pylorus. Symptoms and diagnosis].
PubMed: [The phosphocalcium syndrome of cirrhosis].
PubMed: [Diagnosis of non-traumatic coma].
PubMed: [Idiopathic hypercalciuria -- 28 cases from personal practice].
PubMed: [Data on systematic endocrine examinations of 65 young patients with apparently isolated endocrine cataracts].
PubMed: [Clinical forms of cancer of the pancreas].
PubMed: [Aplasia of the labia minora, genital infantilism & ovarian sclerosis in genetically male women].
PubMed: [Clinical forms, diagnosis & treatment of viral hepatitis].
PubMed: [Severe diabetes treated by intrahypophyseal administration of a radiogold pellet].
PubMed: [Diabetes new medical agents for oral administration].
PubMed: [Acute kidney disease after ingestion of mercuric nitrate; findings on the treatment of kidney diseases caused by mercurials].
PubMed: [Not Available].
PubMed: Chemical Investigations of Fruits and their Products: The Fate of Sugar during "Cider Sickness.".
PubMed: Chemical Investigations of Fruits and their Products: Apple Juice as a Source of Sorbitol.
PubMed: The Pectin Content of Normal and "Silvered" Apple Leaves.
PubMed: Pectin and its Hypothetical Precursor, "Protopectin.".
PubMed: A Note on the Hydrolysis of Pectin.
PubMed: The Behaviour of Pectin towards Alkalis and Pectase.
PubMed: Carnosine, Constitution and Synthesis.
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