PCOG CEE - Alkaloids (My version/ No chem tests)

• Basic nitrogenous plant constituents which are physiologically active

• Most of them end in -ine

Alkaloids

Functions of Alkaloids in Plants

• Poisonous agents

• End product of detoxification

• Regulatory growth factors

• Reserve substances for nitrogen supply

Mnemonic for not solid alkaloids

Liquid “CANS”

All alkaloids are solids, except?(liquids)

• Coniine

• Arecoline

• Nicotine

• Sparteine

Coniine origin

from poison hemlock, Conium maculatum

Arecoline origin

from betel nut, Areca catechu

Nicotine origin

from tobacco, Nicotiana tabacum

Sparteine origin

from Scotch broom, Cystisus scoparius, and lupin, Lupinus mutabilis

EXTRACTION OF ALKALOIDS:
Alkaloid: Pyridine-Piperidine
Origin:?

Ornithine

EXTRACTION OF ALKALOIDS:
Alkaloid: Tropane/Solanaceous
Origin:?

Tropic acid, Phe, Ornithine
with 3-acetate derived carbon

EXTRACTION OF ALKALOIDS:
Alkaloid: Quinoline
Origin:?

Trp (W)

EXTRACTION OF ALKALOIDS:
Alkaloid: Isoquinoline
Origin:?

Tyr (Y)

EXTRACTION OF ALKALOIDS:
Alkaloid: Imidazole
Origin:?

His (H)

EXTRACTION OF ALKALOIDS:
Alkaloid: Steroidal
Origin:?

CPPP

EXTRACTION OF ALKALOIDS:
Alkaloid: Indole
Origin:?

Trp (W)

EXTRACTION OF ALKALOIDS:
Alkaloid: Alkaloidal Amines
Origin:?

Phe, Tyr, Trp

EXTRACTION OF ALKALOIDS:
Alkaloid: Purine/Methylxanthines
Origin:?

Gly, Gln, Asp, CO2, Tetrahydrofolate

PYRIDINE-PIPERIDINE examples

• Tobacco

• Areca, Betel nut

• Lobelia, Indian Tobacco

PYRIDINE-PIPERIDINE:

Tobacco SN

Nicotiana tabacum

PYRIDINE-PIPERIDINE:
Tobacco AC

Nicotine

PYRIDINE-PIPERIDINE:
Tobacco Uses

CNS stimulant, Smoking deterrent (Nicorette©)

PYRIDINE-PIPERIDINE:
Betel nut SN

Areca catechu

PYRIDINE-PIPERIDINE:
Betel nut AC

Arecoline

PYRIDINE-PIPERIDINE:
Betel nut Uses

Anthelmintic

PYRIDINE-PIPERIDINE:
Areca, Betel nut Preparation

Punsupari (Areca, Lime, leaves of Piper beetle) – stimulant masticatory

PYRIDINE-PIPERIDINE:
Tannin content can cause esophageal cancer

Areca, Betel nut

PYRIDINE-PIPERIDINE:
Indian Tobacco SN

Lobelia inflata

PYRIDINE-PIPERIDINE:
Lobelia other name

Indian Tobacco

PYRIDINE-PIPERIDINE:
Indian Tobacco AC

Lobeline

PYRIDINE-PIPERIDINE:
Indian Tobacco Uses

CNS stimulant, Smoking deterrent (Bantron©)

TROPANE/SOLANACEOUS examples (10)

• Belladona, Deadly nightshade

• Hyoscyamus, Henbane

• Egyptian henbane

• Stramonium, Jimson weed, Jamestown weed

• Withania

• Duboisia

• Pituri, Australian tobacco

• Mandragora, European mandrake

• Datura fastuosa

• Coca, Divine plant of the Incas

TROPANE/SOLANACEOUS:
Belladona, Deadly nightshade SN

Atropa belladona

TROPANE/SOLANACEOUS:
Belladona, Deadly nightshade AC

Hyoscyamine ➔ Atropine

TROPANE/SOLANACEOUS:
Henbane SN

Hyoscyamus niger

TROPANE/SOLANACEOUS:
Henbane Contanins____ alkaloid

0.04%

TROPANE/SOLANACEOUS:
Hyoscyamus, Henbane AC

Scopolamine, Hyoscyamine

TROPANE/SOLANACEOUS:
Egyptian henbane SN

Hyocyamus muticus

TROPANE/SOLANACEOUS:
Egyptian henbane Contains ___ alkaloid

1.5%

TROPANE/SOLANACEOUS:
Egyptian henbane AC

Scopolamine, Hyoscyamine

TROPANE/SOLANACEOUS:
Stramonium other names

Jimson weed, Jamestown weed

TROPANE/SOLANACEOUS:
Jimson weed, Jamestown weed SN

Datura stramonium
D. metel (talumpunay, thorn apple)

TROPANE/SOLANACEOUS:
Jimson weed, Jamestown weed AC

Scopolamine/Hyoscine

TROPANE/SOLANACEOUS:
Stramonium, Jimson weed, Jamestown weed Uses

Vapor is used for asthma treatment

TROPANE/SOLANACEOUS:
Withania SN

Withania somnifera

TROPANE/SOLANACEOUS:
Withania Use

Contains withanolides (steroidal lactones); used as adaptogen

TROPANE/SOLANACEOUS:
Duboisia SN

Duboisia myoporoides

TROPANE/SOLANACEOUS:
Duboisia Uses

Currently the commercial source of Atropine

TROPANE/SOLANACEOUS:
Duboisia AC

Also contains scopolamine and hyoscyamine

TROPANE/SOLANACEOUS:
Pituri, Australian tobacco SN

Duboisia hopwoodii

TROPANE/SOLANACEOUS:
Pituri other name

Australian tobacco

TROPANE/SOLANACEOUS:
Pituri, Australian tobacco Uses

CNS stimulate

TROPANE/SOLANACEOUS:
Pituri, Australian tobacco AC

Nicotine

TROPANE/SOLANACEOUS:
European mandrake SN

Mandragora officinarum

TROPANE/SOLANACEOUS:
European mandrake AC

mandragorine(related to tropane alkaloids), hyoscyamine, and scopolamine

TROPANE/SOLANACEOUS:
Mandragora, European mandrake Uses

Emetic

TROPANE/SOLANACEOUS:
Datura fastousa origin

Datura metel or Datura fastuosa

TROPANE/SOLANACEOUS:
Datura fastousa Uses

Commercial chief source of Scopolamine

TROPANE/SOLANACEOUS:
Coca other name

Divine plant of the incas

TROPANE/SOLANACEOUS:
Coca, Divine plant of the Incas SN (Huanuco)

Erythroxylum coca

TROPANE/SOLANACEOUS:
Coca, Divine plant of the Incas SN (Peruvian)

Erythroxylum spruceanum

TROPANE/SOLANACEOUS:
Coca, Divine plant of the Incas SN (Truxillo)

Erythroxylum novogranatense var. truxillense

TROPANE/SOLANACEOUS:
Coca, Divine plant of the Incas AC

Cocaine (methyl ester of benzoylecgonine)

TROPANE/SOLANACEOUS:
Coca preparation
-analgesic for cancer pain (Cocaine + Morphine + Chlorpromazine + 90% EtOH)

Brompton’s cocktail –

TROPANE/SOLANACEOUS:
Coca preparation
-inhalation of vapors of cocaine

Free-basing

TROPANE/SOLANACEOUS:
Coca uses

Psychomotor stimulant with a strong abuse potential, euphoric, vasoconstrictor, sedative

QUINOLINE examples

• Cuprea

• Cinchona, Peruvian bark, Jesuit’s bark

QUINOLINE:
Cuprea SN

Remijia purdieana
R. pedunculata

QUINOLINE:
Cuprea uses

Commercial source of Quinidine

QUINOLINE:
Cinchona other names

Peruvian bark, Jesuit’s bark

QUINOLINE:

Peruvian bark, Jesuit’s bark SN (RED)

Cinchona succirubra

QUINOLINE:

Peruvian bark, Jesuit’s bark SN (YELLOW)

Cinchona calisaya

QUINOLINE:
Cinchona
Age of bark that has the maximum amt of alkaloids:__

6-9 yrs

QUINOLINE:
Cinchona was studied by?

Pelletier and Caventou

QUINOLINE:
Cinchona AC

Quinidine (anti-arrhythmic), Quinine (antimalarial)

QUINOLINE:
Cinchona AC anti-arrythmic

Quinidine

QUINOLINE:
Cinchona AC antimalarial

Quinine

QUINOLINE:
6-demethoxy analogs of Cinchonine

Quinidine

QUINOLINE:
6-demethoxy analogs of Cinchonidine

Quinine

QUINOLINE:
Peruvian bark, Jesuit’s bark toxicity

Cinchonism

ISOQUINOLINE:
Ipecac SN (Brazilian)

Carapichea ipecacuanha (formerly Cephalis ipecacuanha)

ISOQUINOLINE:
Ipecac SN (Panama)

Carapichea acuminata (formerly Cephalis acuminata)

ISOQUINOLINE:
Ipecac AC

Emetine/ Methylcephaeline

ISOQUINOLINE:
Ipecac syrup use

Emetic(used to induce vomiting)

ISOQUINOLINE:
Ipecac fluidextract how potent?

14 times more potent than syrup

ISOQUINOLINE:
Dover’s powder content and use

(Ipecac + Opium); Diaphoretic (Induce sweating)

ISOQUINOLINE:
Ipecac original use

Anti-amoebic agent

ISOQUINOLINE:
Golden seal SN

Hydrastis canadensis

ISOQUINOLINE:
Hydrastis other name

golden seal

ISOQUINOLINE:
Hydrastis/Golden seal AC

Hydrastine, Berberine

ISOQUINOLINE:
Hydrastis/Golden seal Use

Astringent

ISOQUINOLINE:
Blood root SN

Sanguinaria canadensis

ISOQUINOLINE:
Sanguinaria other name

Blood root

ISOQUINOLINE:
Blood root AC

Sanguinarine

ISOQUINOLINE:
Blood root, Sanguinaria use

Expectorant, emetic

ISOQUINOLINE:
Curare, South American Arrow Poison SN

Strychnos castelnei

S. Toxifera

Chondrodendon tomentosum

ISOQUINOLINE:

Curare, South American Arrow Poison which type: in a gourd

Calabash

ISOQUINOLINE:

Curare, South American Arrow Poison which type: in a bamboo

Tube

ISOQUINOLINE:

Curare, South American Arrow Poison which type: in a clay pot

Pot

ISOQUINOLINE:

Curare, South American Arrow Poison AC

Tubocurarine

ISOQUINOLINE:

Curare, South American Arrow Poison uses

Skeletal muscle Relaxant (curariform effect), anticonvulsant in strychnine poisoning