Ergot Ann Baker Katie Ditter Carrie Peterson

Botanical Characteristics Parasite Parasite Sclerotium Sclerotium Conidia Conidia Reproduction Reproduction

History of Ergot Discovery Discovery Family Family Names Names Medicinal Purposes Medicinal Purposes Folklore Folklore

History of LSD Discovery Discovery Original Purpose Original Purpose Social Impact Social Impact

Chemistry of Alkaloids Nitrogenous and Basic Nitrogenous and Basic Physiologically Active Physiologically Active Salt and Free Amine Formation Salt and Free Amine Formation Solubility Solubility Crystalline Solid Crystalline Solid Bitter Taste Bitter Taste

The Ergot Alkaloids Structure based on indole ring Structure based on indole ring General biosynthesis of alkaloids General biosynthesis of alkaloids Starting amino acid is tryptophan Starting amino acid is tryptophan All ergot alkaloids are derivatives of (+)- Lysergic Acid All ergot alkaloids are derivatives of (+)- Lysergic Acid

The Ergot Alkaloids Structure based on indole ring Structure based on indole ring Starting amino acid is tryptophan Starting amino acid is tryptophan All ergot alkaloids are derivatives of (+)-Lysergic Acid All ergot alkaloids are derivatives of (+)-Lysergic Acid

General Biosynthesis of Alkaloids

Biosynthesis of Lysergic Acid

Important Derivatives Natural Products: ErgonovineErgotamine Semisynthetic Products: Methylergonovine maleate Dihydroergotamine mesylate Lysergic acid diethylamine Synthetic Products: sumatriptan (Imitrex®)

1630…fed to animals (all died) 1778…duck and drake fed ergot 1831…fed rooster ergot extracts 1909…tyramine 1910…histamine 1884…calmodulin alkaloid …ergotoxine and ergotamine History of Clinical History of ClinicalTrials

Peripheral Effects smooth muscle contractions smooth muscle contractions Cures migraine headaches Cures migraine headaches lowers blood pressure lowers blood pressure extracts used extracts used Ergotamine tartrate + caffeineErgotamine tartrate + caffeine dihydroergotaminedihydroergotamine

Uterotonic Effects childbirthchildbirth accelerate childbirthaccelerate childbirth arrest hemorrhagingarrest hemorrhaging Extracts usedExtracts used ergonovine maleateergonovine maleate ergometrineergometrine ergotamine (prolonged effects)ergotamine (prolonged effects)

Neurohormonal Effects Serotonin antagonism ExtractExtract methysergidemethysergide TreatmentsTreatments prophylaxis for migraineprophylaxis for migraine carciniod syndromecarciniod syndrome rhuematic affectionsrhuematic affections

Neurohormonal Effects Adrenergic blockade TreatmentsTreatments high blood pressurehigh blood pressure cerebral circulatory disorderscerebral circulatory disorders vascular disordersvascular disorders cervical syndromecervical syndrome Extracts usedExtracts used dihydroergocorninedihydroergocornine dihydroergokryptinedihydroergokryptine dihydroergocristinedihydroergocristine

Central Effects Bulbomedullary effects EffectsEffects bradycardiabradycardia vomitingvomiting inhibition of vasomotor centerinhibition of vasomotor center inhibition of pressoreceptor reflexesinhibition of pressoreceptor reflexes ExtractsExtracts ergot alkaloids aloneergot alkaloids alone (has sedative effect)(has sedative effect)

Central Effects Mesodrencephalic effects EffectsEffects hyperthermiahyperthermia hyperglycemiahyperglycemia mydriasismydriasis piloerectionpiloerection tachypneatachypnea hyperreflexiahyperreflexia general motorgeneral motor hyperactivityhyperactivity ExtractExtract lysergidelysergide

LSD

References Robbers, J.E., Speedie, M.K. & Tyler, V.E. (1996) Pharmacognosy and Pharmacobiotechnology. Williams & Williams: Media, PA. Etc.