Introduction to Alkaloids – PST05210 Basic Pharmacognosy

NTA Level 5 • Semester 2 • PST05210

Introduction to Alkaloids

Basic Pharmacognosy • Source Session/Topic 18
Full source-text version: all educational wording from the extracted learning source is retained; only presenter/tutor metadata and web-layout noise are removed, while formatting is improved for readability.

Session 18: Introduction to Alkaloids

Total Session Time: 120 minutes

Prerequisites

• None

Learning Tasks

By the end of this session students are expected to be able to:

• Explain the occurrence and distribution of alkaloids
• Explain naming of alkaloids
• Explain properties of alkaloids

Resources Needed:

• Flip charts, marker pens, and masking tape
• Black/white board and chalk/whiteboard markers

SESSION OVERVIEW

|Step |Time |Activity/ |Content |

| | |Method | |

|1 |05 minutes |Presentation |Introduction, Learning Tasks |

|2 |35 minutes |Presentation |Occurrence and Distribution of |

| | | |Alkaloid |

|3 |35 minutes |Presentation |Naming of Alkaloids |

|4 |35 minutes |Presentation |Properties of Alkaloids |

|5 |05 minutes |Presentation |Key Points |

|6 |05 minutes |Presentation |Evaluation |

SESSION CONTENTS

STEP 1: Presentation of Session Title and Learning Tasks (5 minutes)

READ or ASK students to read the learning objectives and clarify

ASK students if they have any questions before continuing.

STEP 2: Occurrence and Distribution of Alkaloids (35 minutes)

• Alkaloids are basic naturally occurring compounds containing one or more

nitrogen atoms usually in a heterocyclic ring and have a marked

physiological action on man or other animals

• Some alkaloids occur in certain families while others only occur in

specific species

• Alkaloids are highly found in apocynaceae, rubiaceae, solanaceae and

papaveracea

• Alkaloids are not found in rosaceae and labiatae families
• Alkaloids are produced by a large variety of organisms, including

bacteria, fungi, plants, and animals

• Most alkaloids are basic (form salts with acids)
• Some alkaloids are not basic e.g. colchicine, piperine, quaternary

alkaloids.

• The nitrogen in some alkaloids is not in a heterocyclic ring e.g.

Ephedrine, Colchicine, Mescaline.

• Alkaloids are rare in lower plants and richer in dicots than in monocots
• Alkaloids may occur in free state (e.g. as free bases), as salts (e.g.

with organic acids), as glycosides, and as alkaloid N-oxides

• Alkaloids may be found in all parts of the plant, in barks, seeds, roots,

fruits, leaves and in latex

• Functions of alkaloids in the plant;

o Protect against insects and herbivores due to their bitterness and

toxicity

o Are final products of detoxification in some cases.

o Source of nitrogen in case of nitrogen deficiency

o Act as growth regulators in certain metabolic systems.

STEP 3: Properties of Alkaloids (35 minutes)

• Physical properties

o Most alkaloids are crystalline solids, a few are amorphous solids e.g.

emetine.

o Some are liquids that are either volatile or non-volatile

o Majority of the alkaloids are colorless but some are colored;

o Alkaloidal bases are soluble in organic solvents and insoluble in water

o Salts of alkaloids are usually soluble in water and, insoluble or

sparingly soluble in organic solvents.

o Alkaloids are bitter tasting

o Many alkaloids are extremely toxic to other organisms.

o Alkaloids exhibit isomerism e.g. optical isomerism i.e L-ephedrine is

3.5 times more active than d-ephedrine

• Chemical properties

o Alkaloids are amines (may be primary, secondary, tertiary and

quaternary)

o Most alkaloids contain oxygen and are solid in nature e.g.

Atropine.

o Alkaloids are decomposed by heat, except Strychnine and Caffeine

o Alkaloids react with acids to form salts

o Dilute alkalis liberate most alkaloids from their salts e.g. NH3

o Some alkaloids are unstable when exposed to light and oxygen

while others are not

STEP 5: Naming of Alkaloids (35 minutes)

• Alkaloids are named by various methods
• Names of alkaloids end by "ine". These names may be derived from:

o Generic plant name – Atropine from Atropa belladonna

o Specific name of the plant – Cocaine from Erythroxylum coca

o Names of loved ones e.g. Cathelenine

o Common name of the plant – Ergotamine from ergot (rye)

o Physiological action of the plant – Emetine producing emesis

• Prefixes and Suffixes used in naming of alkaloids
• Prefixes:
o "Nor-" designates N-demethylation or N-demethoxylation, e.g.

Norpseudoephedrine and Nornicotine.

o "Apo-" designates dehydration e.g. Apomorphine.

o "Iso-, pseudo-, neo-, and epi-" indicate different types of isomers

• Suffixes:

o "-dine" designates isomerism as Quinidine and Cinchonidine.

o "-ine" indicates, in case of ergot alkaloids, a lower pharmacological

activity e.g. Ergotaminine which is less potent than ergotamine

STEP 7: Key Points (5 minutes)

• Alkaloids are basic naturally occurring compounds containing one or more

nitrogen atoms usually in a heterocyclic ring and have a marked

physiological action on man or other animals

• Alkaloids are produced by a large variety of organisms, including

bacteria, fungi, plants, and animals and are part of the group of natural

products

• Alkaloids may occur in free state (e.g. as free bases), as salts (e.g.

with organic acids),

STEP 8: Evaluation (5 minutes)

• What are alkaloids?
• What are the functions of alkaloids in plants?
• Mention physical properties of alkaloids?

References

Trease, G. E., Evans, W. C., & Evans, D. (2009). Trease and Evans

pharmacognosy. London: Saunders.

Joanne Barnes et al (2002), Herbal medicines 3rd Edition: Pharmaceutical

Press

Wallis, T. E. (2005). Textbook of pharmacognosy. New Delhi: CBS.

Robbers, J. E., Speedie, M. K., Tyler, V. E., & Tyler, V. E. (1996).

Pharmacognosy and pharmacobiotechnology. Baltimore: Williams &

Wilkins.

Heinrich, M., Kinghorn, A. D., Maizels, D., Gibbons, S., & Phillipson, J.

D. (2012). Fundamentals of pharmacognosy and phytotherapy. Edinburgh:

Churchill Livingstone/Elsevier.

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