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ErgotErgot
Ann BakerAnn BakerKatie DitterKatie Ditter
Carrie Carrie PetersonPeterson
Botanical Botanical CharacteristCharacterist
icsics• ParasiteParasite
• SclerotiumSclerotium
• ConidiaConidia
• ReproductionReproduction
History of History of ErgotErgot
• DiscoveryDiscovery• FamilyFamily• • NamesNames• • Medicinal PurposesMedicinal Purposes• FolkloreFolklore
History of LSDHistory of LSD
• • DiscoveryDiscovery
• Original PurposeOriginal Purpose
• Social ImpactSocial Impact
Chemistry of Chemistry of AlkaloidsAlkaloids• • Nitrogenous and BasicNitrogenous and Basic
• • Physiologically ActivePhysiologically Active
• • Salt and Free Amine FormationSalt and Free Amine Formation
• • SolubilitySolubility
• • Crystalline SolidCrystalline Solid
• Bitter TasteBitter Taste
The Ergot The Ergot AlkaloidsAlkaloids
• • Structure based on indole ringStructure based on indole ring• • General biosynthesis of alkaloidsGeneral biosynthesis of alkaloids• • Starting amino acid is tryptophanStarting amino acid is tryptophan
• • All ergot alkaloids are derivatives of (+)-All ergot alkaloids are derivatives of (+)-Lysergic AcidLysergic Acid
The Ergot The Ergot AlkaloidsAlkaloids
• • Structure based on indole ringStructure based on indole ring• • Starting amino acid is tryptophanStarting amino acid is tryptophan• • All ergot alkaloids are derivatives of All ergot alkaloids are derivatives of (+)-Lysergic Acid(+)-Lysergic Acid
General General Biosynthesis of Biosynthesis of
AlkaloidsAlkaloids
Biosynthesis Biosynthesis of Lysergic of Lysergic
AcidAcid
Important DerivativesImportant Derivatives
Natural Products:Natural Products:ErgonovineErgonovineErgotamineErgotamine
Semisynthetic Semisynthetic Products:Products:
Methylergonovine maleateMethylergonovine maleateDihydroergotamine mesylateDihydroergotamine mesylateLysergic acid diethylamineLysergic acid diethylamine
Synthetic Products:Synthetic Products:sumatriptan (Imitrexsumatriptan (Imitrex®)®)
1630…fed to 1630…fed to animals (all died)animals (all died)1778…duck and 1778…duck and drake fed ergotdrake fed ergot1831…fed rooster ergot extracts1831…fed rooster ergot extracts
1909…tyramine 1909…tyramine 1910…histamine1910…histamine
1884…calmodulin 1884…calmodulin alkaloidalkaloid
1906-1918…1906-1918…ergotoxine ergotoxine
and and ergotamineergotamine
History of Clinical History of Clinical TrialsTrials
Peripheral Effects
• smooth muscle contractionssmooth muscle contractions• Cures migraine headachesCures migraine headaches• lowers blood pressurelowers blood pressure
• extracts usedextracts 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 EffectsBulbomedullary 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 EffectsMesodrencephalic effects•EffectsEffects
•hyperthermiahyperthermia•hyperglycemiahyperglycemia•mydriasismydriasis•piloerectionpiloerection•tachypneatachypnea•hyperreflexiahyperreflexia•general motorgeneral motor•hyperactivityhyperactivity •ExtractExtract
•lysergidelysergide
LSD
ReferencesReferencesRobbers, J.E., Speedie, M.K. & Tyler, V.E. (1996) Robbers, J.E., Speedie, M.K. & Tyler, V.E. (1996) Pharmacognosy and Pharmacognosy and
Pharmacobiotechnology.Pharmacobiotechnology. Williams & Williams: Media, PA.Williams & Williams: Media, PA.
Etc.Etc.