Lesson 7. Alkaloids (FULL)

Derosne

isolated narcotine in 1803

Serturner

isolated morphine in 1816

Pelletier and Caventou

isolated strychnine, emetine, brucine, piperine, caffeine, quinine, colchicine, coniine in 1817 to 1826

Coniine

first alkaloid with established structure isolated by Schiff

True alkaloids

a. ________________ are of rare occurrence in other organisms

b. In fungi, the ______________________________________ are best known

c. Also present in __________________ (many are antimicrobial)

d. includes Ephedra, Taxus

a = ?

lysergic acid derivatives and sulfur-containing alkaloids

a. ________________ are of rare occurrence in other organisms

b. In fungi, the ______________________________________ are best known

c. Also present in __________________ (many are antimicrobial)

d. includes Ephedra, Taxus

b = ?

amphibians

a. ________________ are of rare occurrence in other organisms

b. In fungi, the ______________________________________ are best known

c. Also present in __________________ (many are antimicrobial)

d. includes Ephedra, Taxus

c = ?

Pteridophytes

a. ________________ are of rare occurrence in other organisms

b. In fungi, the ______________________________________ are best known

c. Also present in __________________ (many are antimicrobial)

d. includes Ephedra, Taxus

d = ?

nitrogen

GENERAL STRUCTURE OF ALKALOIDS

• Alkaloids are alkali due to the universal presence of __________

acids

GENERAL STRUCTURE OF ALKALOIDS

• Nitrogenous compounds and unite with _____ to form salts.

crystalline

GENERAL STRUCTURE OF ALKALOIDS

• Most alkaloids are ______________ solids

salts or N-oxides

GENERAL STRUCTURE OF ALKALOIDS

• Alkaloids may exist in the free state as _______________________

oxygen

GENERAL STRUCTURE OF ALKALOIDS

• Most alkaloids contain a._______________

• Some that don’t contain these are b.___________ at room temperature which includes c.____________________________.

a = ?

liquids

GENERAL STRUCTURE OF ALKALOIDS

• Most alkaloids contain a._______________

• Some that don’t contain these are b.___________ at room temperature which includes c.____________________________.

b = ?

sparteine, coniine, arecoline, and nicotine

GENERAL STRUCTURE OF ALKALOIDS

• Most alkaloids contain a._______________

• Some that don’t contain these are b.___________ at room temperature which includes c.____________________________.

c = ?

color

GENERAL STRUCTURE OF ALKALOIDS

• Alkaloids rarely have a.__________

• exemptions: berberine is b.______________ and sanguinarine is c.____

a = ?

yellow

GENERAL STRUCTURE OF ALKALOIDS

• Alkaloids rarely have a.__________

• exemptions: berberine is b.______________ and sanguinarine is c.____

b = ?

red

GENERAL STRUCTURE OF ALKALOIDS

• Alkaloids rarely have a.__________

• exemptions: berberine is b.______________ and sanguinarine is c.____

c = ?

water

GENERAL STRUCTURE OF ALKALOIDS

• Free bases are sparingly soluble in a.______ and soluble in b._________

• The solubility is reversed when converted to c.___________

a = ?

organic solvent

GENERAL STRUCTURE OF ALKALOIDS

• Free bases are sparingly soluble in a.______ and soluble in b._________

• The solubility is reversed when converted to c.___________

b = ?

alkaloidal salts

GENERAL STRUCTURE OF ALKALOIDS

• Free bases are sparingly soluble in a.______ and soluble in b._________

• The solubility is reversed when converted to c.___________

c = ?

Mescaline

CLASSIFICATION OF ALKALOIDS BASED ON THE TYPE OF AMINE:

• primary

ephedrine

CLASSIFICATION OF ALKALOIDS BASED ON THE TYPE OF AMINE:

• secondary

atropine

CLASSIFICATION OF ALKALOIDS BASED ON THE TYPE OF AMINE:

• tertiary

tubocurarine

CLASSIFICATION OF ALKALOIDS BASED ON THE TYPE OF AMINE:

• quaternary

True Alkaloids

CLASSIFICATION OF ALKALOIDS

• alkaloids that have a nitrogenous heterocycle and is derived from an amino acid

Pseudoalkaloids

CLASSIFICATION OF ALKALOIDS

• heterocyclic alkaloids not derived from amino acids

Protoalkaloids

CLASSIFICATION OF ALKALOIDS

• non-nitrogenous heterocycle derived from amino acids

Lysine

ORIGINS OF ALKALOIDS:

• Coniine (Piperidine)

Ornithine Aspartate

ORIGINS OF ALKALOIDS:

• Nicotine (Pyridine, Pyrrolidine)

Ornithine

ORIGINS OF ALKALOIDS:

• Cocaine (Tropane)

Tryptophane

ORIGINS OF ALKALOIDS:

• Quinine (Quinoline)

Tyrosine

ORIGINS OF ALKALOIDS:

• Morphine (Isoquinoline)

Purine (Aspartate, Glycine, Glutamine)

ORIGINS OF ALKALOIDS:

• Caffeine (Purine)

water

METHODS OF EXTRACTION

Process A:

1. Powdered material is moistened with ________, mixed with lime

2. Extraction is done with organic solvents like ____________________

3. Organic liquid is then shaken with ___________ and allowed to separate

4. ____________ now in aqueous liquid

5. ___________ are in organic liquid

1 = ?

ether or petroleum spirit

METHODS OF EXTRACTION

Process A:

1. Powdered material is moistened with ________, mixed with lime

2. Extraction is done with organic solvents like ____________________

3. Organic liquid is then shaken with ___________ and allowed to separate

4. ____________ now in aqueous liquid

5. ___________ are in organic liquid

2 = ?

aq. acid

METHODS OF EXTRACTION

Process A:

1. Powdered material is moistened with ________, mixed with lime

2. Extraction is done with organic solvents like ____________________

3. Organic liquid is then shaken with ___________ and allowed to separate

4. ____________ now in aqueous liquid

5. ___________ are in organic liquid

3 = ?

Alkaloid salts

METHODS OF EXTRACTION

Process A:

1. Powdered material is moistened with ________, mixed with lime

2. Extraction is done with organic solvents like ____________________

3. Organic liquid is then shaken with ___________ and allowed to separate

4. ____________ now in aqueous liquid

5. ___________ are in organic liquid

4 = ?

impurities

METHODS OF EXTRACTION

Process A:

1. Powdered material is moistened with ________, mixed with lime

2. Extraction is done with organic solvents like ____________________

3. Organic liquid is then shaken with ___________ and allowed to separate

4. ____________ now in aqueous liquid

5. ___________ are in organic liquid

5 = ?

water or aqueous alcohol

METHODS OF EXTRACTION

Process B:

1. Powdered material is extracted with ________________________ containing dilute acid

2. Pigments and other unwanted materials are removed by shaking with ____________________

3. Free alkaloids are precipitated with _____________________________ and separated by filtration

1 = ?

chloroform or other organic solvents

METHODS OF EXTRACTION

Process B:

1. Powdered material is extracted with ________________________ containing dilute acid

2. Pigments and other unwanted materials are removed by shaking with ____________________

3. Free alkaloids are precipitated with _____________________________ and separated by filtration

2 = ?

sodium bicarbonate or ammonia

METHODS OF EXTRACTION

Process B:

1. Powdered material is extracted with ________________________ containing dilute acid

2. Pigments and other unwanted materials are removed by shaking with ____________________

3. Free alkaloids are precipitated with _____________________________ and separated by filtration

3 = ?

Pyridine-Piperidine

P Alkaloids are traditionally called ____________________ alkaloids.

Pyridine

P ALKALOIDS MONOCYCLIC STRUCTURES:

• from ornithine/aspartate

Piperidine

P ALKALOIDS MONOCYCLIC STRUCTURES:

• from lysine

Pyrrolidine

P ALKALOIDS MONOCYCLIC STRUCTURES:

• from ornithine/aspartate

ornithine

P ALKALOIDS MONOCYCLIC STRUCTURES:

• from pyrrolizidine

Nicotiana tabacum

P ALKALOIDS

Tobacco

Scientific Name: ?

Family:

Constituents:

Solanaceae

P ALKALOIDS

Tobacco

Scientific Name:

Family: ?

Constituents:

Nicotine

P ALKALOIDS

Tobacco

Scientific Name:

Family:

Constituents: ?

Smoking Cessation

P ALKALOIDS

Tobacco

• use

Lung Cancer

P ALKALOIDS

Tobacco

• can cause _______________

Lobelia inflata

P ALKALOIDS

Indian Tobacco

Scientific Name: ?

Family:

Constituents:

Lobeliaceae

P ALKALOIDS

Indian Tobacco

Scientific Name:

Family: ?

Constituents:

Lobeline (0.25%)

P ALKALOIDS

Indian Tobacco

Scientific Name:

Family:

Constituents: ?

smoking cessation

P ALKALOIDS

Indian Tobacco Uses:

1. For _________________________

2. _____________________ stimulation

3. Treats _______________________________________

4. __________________________ preparations

5. _____________________ of newborn infants

1 = ?

neuromuscular

P ALKALOIDS

Indian Tobacco Uses:

1. For _________________________

2. _____________________ stimulation

3. Treats _______________________________________

4. __________________________ preparations

5. _____________________ of newborn infants

2 = ?

spasmodic asthma and chronic bronchitis

P ALKALOIDS

Indian Tobacco Uses:

1. For _________________________

2. _____________________ stimulation

3. Treats _______________________________________

4. __________________________ preparations

5. _____________________ of newborn infants

3 = ?

antismoking

P ALKALOIDS

Indian Tobacco Uses:

1. For _________________________

2. _____________________ stimulation

3. Treats _______________________________________

4. __________________________ preparations

5. _____________________ of newborn infants

4 = ?

Resuscitation

P ALKALOIDS

Indian Tobacco Uses:

1. For _________________________

2. _____________________ stimulation

3. Treats _______________________________________

4. __________________________ preparations

5. _____________________ of newborn infants

5 = ?

paralytic

P ALKALOIDS

Indian Tobacco

• It becomes a ________________ in toxic doses.

Cytisus scoparius

P ALKALOIDS

Broom

Scientific Name: ?

Family:

Constituents:

Fabaceae

P ALKALOIDS

Broom

Scientific Name:

Family: ?

Constituents:

Sparteine, Cytisine

P ALKALOIDS

Broom

Scientific Name:

Family:

Constituents: ?

Mild diuretic and cathartic

P ALKALOIDS

Broom

• uses

a4B2

P ALKALOIDS

Broom

• Due to its cytisine content, it is a partial agonist at a.__________ and is used for b.____________________

a = ?

smoking cessation

P ALKALOIDS

Broom

• Due to its cytisine content, it is a partial agonist at a.__________ and is used for b.____________________

b = ?

Varenicline

P ALKALOIDS

Broom

• artificial alternative is ________________

Conium maculatum

P ALKALOIDS

Poison Hemlock

Scientific Name: ?

Family:

Constituents:

Apiaceae

P ALKALOIDS

Poison Hemlock

Scientific Name:

Family: ?

Constituents:

Coniine

P ALKALOIDS

Poison Hemlock

Scientific Name:

Family:

Constituents: ?

KOH

P ALKALOIDS

Poison Hemlock

• When mixed with a._______, it develops a b._________________ due to c.______________________.

a = ?

strong, mouse-like odor

P ALKALOIDS

Poison Hemlock

• When mixed with a._______, it develops a b._________________ due to c.______________________.

b = ?

liberation of coniine

P ALKALOIDS

Poison Hemlock

• When mixed with a._______, it develops a b._________________ due to c.______________________.

c = ?

draught

P ALKALOIDS

• Poison Hemlock are used by the Greeks for preparing a ___________ by means of which criminals were put to death.

Areca catechu

P ALKALOIDS

Betel Nut

Scientific Name: ?

Family:

Constituent:

Arecaceae

P ALKALOIDS

Betel Nut

Scientific Name:

Family: ?

Constituent:

Arecoline and Guavacine

P ALKALOIDS

Betel Nut

Scientific Name:

Family:

Constituent: ?

Taenicide

P ALKALOIDS

Betel Nut

• used as a ___________ in the east

leaves of Piper betle and lime

P ALKALOIDS

Betel Nut

• chewed with a.___________________________________

• its b._________________ content can cause c.______________________

a = ?

Arecatannins

P ALKALOIDS

Betel Nut

• chewed with a.___________________________________

• its b._________________ content can cause c.______________________

b = ?

oropharyngeal and esophageal cancer

P ALKALOIDS

Betel Nut

• chewed with a.___________________________________

• its b._________________ content can cause c.______________________

c = ?

Punica granatum

P ALKALOIDS

Pomegranate

Scientific Name: ?

Family:

Constituents:

Punicaceae

P ALKALOIDS

Pomegranate

Scientific Name:

Family: ?

Constituents:

Pelletierine and Isopelletierine

P ALKALOIDS

Pomegranate

Scientific Name:

Family:

Constituents: ?

anthelminthic for tapeworms

P ALKALOIDS

Pomegranate Uses:

1. Pelletierine tannate is an ____________________________

2. Treatment for __________________________

1 = ?

hemorrhoids

P ALKALOIDS

Pomegranate Uses:

1. Pelletierine tannate is an ____________________________

2. Treatment for __________________________

2 = ?

Piper nigrum

P ALKALOIDS

Black Pepper

Scientific Name: ?

Family:

Constituents:

Piperaceae

P ALKALOIDS

Black Pepper

Scientific Name:

Family: ?

Constituents:

Piperine and Piperettine

P ALKALOIDS

Black Pepper

Scientific Name:

Family:

Constituents: ?

piperine

P ALKALOIDS

Black Pepper

• Its pungency is ascribed to _________________

gonorrhea and chronic bronchitis

P ALKALOIDS

Black Pepper

• used in the treatment of ____________________________

Piper retrofractum or Piper longum

P ALKALOIDS

Black Pepper Allied Drugs:

1. scientific name of long pepper

2. scientific name of cubeb

3. used as a potential antihypercholesterolemic because it is used as an acyl-CoA: cholesterol acyltransferase inhibitor

1 = ?

Piper cubeba

P ALKALOIDS

Black Pepper Allied Drugs:

1. scientific name of long pepper

2. scientific name of cubeb

3. used as a potential antihypercholesterolemic because it is used as an acyl-CoA: cholesterol acyltransferase inhibitor

2 = ?

Guineesine

P ALKALOIDS

Black Pepper Allied Drugs:

1. scientific name of long pepper

2. scientific name of cubeb

3. used as a potential antihypercholesterolemic because it is used as an acyl-CoA: cholesterol acyltransferase inhibitor

3 = ?

Lycopodium clavulatum

P ALKALOIDS

Clubmoss

Scientific Name: ?

Family:

Constituents:

Lycopodiaceae

P ALKALOIDS

Clubmoss

Scientific Name:

Family: ?

Constituents:

Lycopodiumoleic acid and Lycopodine

P ALKALOIDS

Clubmoss

Scientific Name:

Family:

Constituents: ?

dusting powder for pills and medicated snuffs

P ALKALOIDS

Clubmoss Uses:

1. Limited extent in ______________________________

2. Used in ________________________

1 = ?

quantitative microscopy

P ALKALOIDS

Clubmoss Uses:

1. Limited extent in ______________________________

2. Used in ________________________

2 = ?