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
Identification
| Name | tutin |
| CAS Number | 2571-22-4 |
| FDA UNII | B69P754702 |
| Molecular Formula | C15 H18 O6 |
| Molecular Weight | 294.30366000 |
| Nikkaji Number | J9.962G |
Regulatory
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) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | unreported-guinea pig LDLo 2 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 3613 ug/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
No supplier data available
Potential Uses
Natural Occurrence
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
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 (ElazıÄ-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.