6117 LEC ALKALOIDS

“P” ALKALOIDS

• Traditionally called pyridine-piperidine alkaloids, but other alkaloids have other rings

Pyridine

• From ornithine/aspartate

• Benzene core where one =CH– grp is replaced by =N–

“P” ALKALOIDS

• Traditionally called pyridine-piperidine alkaloids, but other alkaloids have other rings

Pyridine

• From ornithine/aspartate

• Benzene core where one =CH– grp is replaced by =N–

Piperidine

• From lysine

• Cyclohexane where 1 C is replaced by N

Pyrrolidine

• From ornithine/aspartate

• 5-membered ring with 1 N and 4 C

Pyrrolizidine

• From ornithine

• 2 fused pyrrolidine rings

“P” ALKALOIDS

may come from

• plants, though some are found in insects, amphibians, and marine animals. 

TOBACCO

P

TOBACCO

Scientific Name

Nicotiana tabacum

TOBACCO

Family

Solanaceae

TOBACCO

Constituent

Nicotine

TOBACCO

Uses

• Smoking  cessation

• Stimulant

• Appetite-suppressant

• Short feeling of euphoria

TOBACCO

addtl info

• Can cause lung cancer 

• Leaves are “cured” to enhance properties

INDIAN TOBACCO

P

INDIAN TOBACCO

Scientific Name

Lobelia inflata

INDIAN TOBACCO

Family

Lobeliaceae

INDIAN TOBACCO

Constituents

Lobeline (0.25%)

INDIAN TOBACCO

Uses

• Smoking cessation

• Neuromuscular stimulation

• For spasmodic asthma and chronic bronchitis

• Antismoking preparations

• Resuscitation of newborn infants

BROOM

P

BROOM

Scientific Name

Cytisus scoparius

BROOM

Family

Fabaceae

BROOM

Constituents

• Sparteine

• cystisine

BROOM

Uses

• Mild diuretic

• cathartic

• smoking cessation (cytisine)

Cytisine

• is an α4β2 partial agonist (can also help release dopamine)

  • Used for smoking cessation

Cytisine

artificial alternative

Varenicline

POISON HEMLOCK

P

POISON HEMLOCK

Scientific Name

Conium maculatum

POISON HEMLOCK

Family

Apiaceae

POISON HEMLOCK

Constituents

Coniine

POISON HEMLOCK

Uses

• Develop strong, mouse-like odor with KOH due to liberation of coniine.

• For preparing draught (Greeks) by means of which criminals were put to death

BETEL NUT

P

BETEL NUT

Scientific Name

Areca catechu

BETEL NUT

Family

Arecaceae

BETEL NUT

Constituents

• Arecoline

• guavacine

BETEL NUT

Uses

• Cause oropharyngeal and esophageal cancer

• teanicide in the east

• chewed with Piper betel leaves and lime.

Arecatannins from betel nut

can cause oropharyngeal and esophageal cancer

POMEGRANATE

P

POMEGRANATE

Scientific Name

Punica granatum

POMEGRANATE

Family

Punicaceae

POMEGRANATE

Constituents

• Pelletierine

• isopelletierine

POMEGRANATE Uses

• Anthelmintic (Pelletierine tannate for tapeworms)

• for hemorrhoids.

BLACK PEPPER

P

BLACK PEPPER

Scientific Name

Piper nigrum

BLACK PEPPER

Family

Piperaceae

BLACK PEPPER

Constituents

• Piperine

• piperettine

BLACK PEPPER

Uses

• Once employed in treatment of gonorrhea and chronic bronchitis

• Pungency ascribed to piperine

BLACK PEPPER

Allied Drugs

• Long Pepper

• Cubeb

• Guineesine

Long Pepper

Piper retrofractum, Piper longum

Cubeb

Piper cubeba

Guineesine

• acyl-CoA:cholesterol acyltransferase inhibitor.

• Potential antihypercholesterolemic.

CLUBMOSS

P

CLUBMOSS

Scientific Name

Lycopodium clavulatum

CLUBMOSS

Family

Lycopodiaceae

CLUBMOSS

Constituents

• Lycopodiumoleic acid

• lycopodine

CLUBMOSS

Uses

• Limited extent in dusting powders and medicated snuffs

• dusting powder for pills.

• Quantitative microscopy

• Firecracker making (during the old times)

PYRROLIZIDINE ALKALOIDS

P

PYRROLIZIDINE ALKALOIDS

• Hepatotoxic alkaloids.

• Some are also carcinogenic or mutagenic.

PYRROLIZIDINE ALKALOIDS

• Comfrey

• coltsfoot

• Indicine

• Australine

Comfrey, coltsfoot

Ecologic role in some species of butterflies

Indicine

Antitumor

Australine

Glycosidase inhibitory activity

Tropane

is a bicyclo[3.2.1] structure

Tropane

Suggested precursors

Ornithine, putrescine, and acetate

Tropane

N-methyl group

from methionine

Tropane

Tropic acid fragment

from phenylalanine

THE DEADLY NIGHTSHADE

TROPANES

THE DEADLY NIGHTSHADE

Scientific Name

Atropa belladonna

THE DEADLY NIGHTSHADE

Family

Solanaceae

THE DEADLY NIGHTSHADE

Constituents

Hyoscyamine/atropine (0.30%)

THE DEADLY NIGHTSHADE

Note

Atropine is actually a racemate of dextro and levo forms of hyoscyamine.

JIMSONWEED

TROPANES

JIMSONWEED

Synonyms

• Thornapple,

• Angel's Trumpet

JIMSONWEED

Scientific Name

Datura stramonium

JIMSONWEED

Family

Solanaceae

JIMSONWEED

Allies

• D. innoxia

• D. metel

• D. fastuosa

JIMSONWEED

Constituents

Hyoscyamine (NLT 0.25%)

D. fastuosa

is the chief source of scopolamine

HENBANE

TROPANES

HENBANE

Synonym

Stinking nightshade

HENBANE

Scientific Name

Hyoscyamus niger (annual = var. β-annus; biennial = var. α-biennis)

HENBANE

Constituents

Hyoscyamine (0.05%)

HENBANE

Uses

• Used in preparations intended to burn (for relief of asthma).

• Resembles belladonna and stramonium in action but weaker.

Egyptian henbane:

H. muticus

DUBOISIA

TROPANES

DUBOISIA

Scientific Name

Duboisia myoporoides,

D. hopwoodii (Pituri)

DUBOISIA

Family

Solanaceae

DUBOISIA

Constituents

• Hyoscine

• hyoscyamine

DUBOISIA

Uses

• A good source of atropine

• Principally nicotine and related alkaloids

ASWAGANDHA

TROPANES

ASWAGANDHA

Scientific Name

Withania somnifera

ASWAGANDHA

Family

Solanaceae

AHWAGANDHA

Constituents

• Tropine

• hygrine

ASWAGANDHA

Uses

Sedative

Henbane

For asthma

Scopolamine as hyoscine N-butylbromide

For motion sickness

Hyoscine HBr

For control of secretions pre-op.

Atropine is mydriatic

For eye examinations

COCA

TROPANES

COCA

Scientific Name

Erythroxylum coca

COCA

Family

Erythroxylaceae

COCA

Constituents

(0.7%-1.5%).

• Cocaine

• ecgonine

• cuscohygrine