S1 L1 Introduction to

Pharmacognosy
Anna Drew
with slide contribution from Bob Hoffman
& grateful acknowledgement for inspirational teaching received at the
School of Pharmacy, University of London

 Pharmacognosy
pharmakon a drug (Greek)
gignosco to acquire knowledge of (Greek)
OR cognosco to know about (Latin)

Johann Adam Schmidt (1759-1809)

Lehrbuch der Materia Medica
Published Vienna 1811
Beethovens physician

Naturally occurring substances having

a medicinal action:

Surgical dressings prepared from natural fibres

Flavourings and suspending agents
Disintegrants
Filtering and support media

Other associated fields:

Poisonous and hallucinogenic plants

Raw materials for production of oral contraceptives
Allergens
Herbicides and insecticides

Pharmacognosy is related to:

Botany
Ethnobotany
Marine biology
Microbiology
Herbal medicine
Chemistry (phytochemistry)
Pharmacology
Pharmaceutics

Skills & techniques valuable elsewhere:

Analysis of other commodoties
Foods, spices, gums, perfumes, fabrics, cosmetics

Used by
Public analysts, forensic sciences, quality-control scientists

Role in pure sciences

Botany, plant taxonomy, phytochemistry

Botanists and chemists looking at:

Chemical plant taxonomy, genetic/enzymatic studies involving 2 y
metabolites
Artificial and tissue culture
Effects of chemicals on plant metabolites
Induction of abnormal syntheses
Bioassay-guided isolation techniques

Vegetable drugs can be arranged for study:

Alphabetical
Taxonomic**
botanical classification

Morphological
Organised drugs: leaves, flowers, fruit, seeds etc
Unorganised drugs: extracts, gums, resins, oils etc

Pharmacological/therapeutic*
Increasingly used with screening
Constituents of one drug may fall into several groups

Chemical/biogenetic
Constituents or biosynthetic pathways

CLASS
SUBCLASS

Angiospermae (Angiosperms)

Plants which produce flowers

Gymnospermae (Gymnosperms)

Plants which don't produce flowers

Dicotyledonae (Dicotyledons, Dicots)

Plants with two seed leaves

Monocotyledonae (Monocotyledons, Monocots)

Plants with one seed leaf

SUPERORDER

A group of related Plant Families, classified in the order in which they are thought to have
developed their differences from a common ancestor.
There are six Superorders in the Dicotyledonae (Magnoliidae, Hamamelidae, Caryophyllidae,
Dilleniidae, Rosidae, Asteridae), and four Superorders in the Monocotyledonae
(Alismatidae, Commelinidae, Arecidae, Liliidae)
The names of the Superorders end in -idae

ORDER

Each Superorder is further divided into several Orders.

The names of the Orders end in -ales

FAMILY

Each Order is divided into Families. These are plants with many botanical features in common,
and is the highest classification normally used. At this level, the similarity between plants
is often easily recognisable by the layman.
Modern botanical classification assigns a type plant to each Family, which has the particular
characteristics which separate this group of plants from others, and names the Family after
this plant.
The number of Plant Families varies according to the botanist whose classification you follow.
Some botanists recognise only 150 or so families, preferring to classify other similar plants
as sub-families, while others recognise nearly 500 plant families. A widely-accepted
system is that devised by Cronquist in 1968, which is only slightly revised today.
The names of the Families end in -aceae

SUBFAMILY

The Family may be further divided into a number of sub-families, which group together plants
within the Family that have some significant botanical differences.
The names of the Subfamilies end in -oideae

TRIBE

A further division of plants within a Family, based on smaller botanical differences, but still usually
comprising many different plants.
The names of the Tribes end in -eae

SUBTRIBE

A further division, based on even smaller botanical differences, often only recognisable to botanists.
The names of the Subtribes end in -inae

GENUS

This is the part of the plant name that is most familiar, the normal name that you give a plant - Papaver
(Poppy), Aquilegia (Columbine), and so on. The plants in a Genus are often easily recognisable as
belonging to the same group.
The name of the Genus should be written with a capital letter.

SPECIES

This is the level that defines an individual plant. Often, the name will describe some aspect of the plant
- the colour of the flowers, size or shape of the leaves, or it may be named after the place where it
was found. Together, the Genus and species name refer to only one plant, and they are used to
identify that particular plant. Sometimes, the species is further divided into sub-species that
contain plants not quite so distinct that they are classified as Varieties.
The name of the species should be written after the Genus name, in small letters, with no capital letter.

VARIETY

A Variety is a plant that is only slightly different from the species plant, but the differences are not so
insignificant as the differences in a form. The Latin is varietas, which is usually abbreviated to var.
The name follows the Genus and species name, with var. before the individual variety name.

FORM

A form is a plant within a species that has minor botanical differences, such as the colour of flower or
shape of the leaves.
The name follows the Genus and species name, with form (or f.) before the individual variety name.

CULTIVAR

A Cultivar is a cultivated variety, a particular plant that has arisen either naturally or through deliberate
hybridisation, and can be reproduced (vegetatively or by seed) to produce more of the same plant.
The name follows the Genus and species name. It is written in the language of the person who
described it, and should not be translated. It is either written in single quotation marks or has cv.
written in front of the name.

Example
Linnaeus (1707-1778), Swedish biologist

Division
Class
Subclass
Order
Suborder
Family
Subfamily
Tribe
Genus
Species
Varieties

Angiospermae
Dicotyledoneae
Sympetalae
Tubiflorae
Verbenineae
Labiatae (Lamiaceae)
Stachydoideae
Satureieae
Mentha
Mentha piperita Linnaeus (peppermint)
Mentha piperita var. officinalis Sole
(White Peppermint); Mentha piperita var.
vulgaris Sole (Black Peppermint)

Contribution of plants to
medicine and pharmacy
18th century drugs plant based
19th century a range of drugs was isolated:

1805 morphine
1817 emetine
1819 strychnine
1820 quinine

Famous plants/plant drugs?

Quinine
Cinchona bark, South American tree
Used by Incas; dried bark ground and mixed
with wine
First used in Rome in 1631
Extracted 1820
Large scale use 1850
Chemical synthesis 1944
Actual tree remains the most economic source

Belladonna -> atropine

Anticholinergic
syndrome:

Hot as hell
Blind as a bat
Red as a beet
Dry as a bone
Mad as a hatter

Physostigma
venosum
Calabar bean

Efik People

Efik Law
Trial by ordeal
A suspected person is given 8 beans ground and
added to water as a drink. If he is guilty, his mouth
shakes and mucus comes from his nose. His
innocence is proved if he lifts his right hand and
then regurgitates (Simmons 1952)

Deadly esere
Administration of the Calabar bean

First observed by WF Daniell in 1840

Later described by Freeman 1846 in a
Communication to the Ethnological
Society of Edinburgh

Physostigmine or Eserine
First isolated in 1864 by Jobst & Hesse

Taxol

Pacific Yew tree, Taxus brevifolia, bark

1964 activity discovered at NCI
1966 paclitaxel isolated
Mitotic inhibitor
interferes with normal microtubule growth during cell div

Used for cancer chemotherapy

lung, ovarian, breast, head & neck, Kaposis sarcoma

 1969
1200kg bark -> 28kg crude extract -> 10g pure

1975 active in another in vitro assay

1977 7000 pounds bark requested to make 600g

1978 Mildly active in leukaemic mice

1979 Horowitz; unknown mechanism
involved stabilising of microtubules
1980 20,000 pounds of bark needed

1982 Animal studies completed

 1984 Phase I trials

12,000 pounds for Phase II to go ahead

1986 Phase II trials began

Recognised 60,000 pounds miniumum needed
Environmental concerns voiced

1988
An effect in melanoma
RR of 30% refractory ovarian cases
Annual destruction of 360,000 trees to treat all US cases

1989 NCI handed over to BMS

Agreed to find alternative production pathway
1992 BMS given FDA approval & 5yrs marketing rights
Trademark Taxol Generic paclitaxel

2000 sales peaked US$1.6 billion

Now available as generic

Alternative production
1967-1993 all sourced from Pacific Yew
Late 1970s synthetic production from petrochemicalderived starting materials
1981 Potier isolated 10-deacetylbaccitin from Taxus
baccata needles
1988 published semi-synthetic route
1992 Holton patented improved process improving
yield to 80%
1995 use of Pacific Yew stopped
Now plant cell fermentation (PCF) technology used
Also found in fungi
Race for synthetic production -> docetaxel

Why do we need plants?

1. Source of drug molecules

Most drugs can be synthesised

Still more economical to use the plant
Papaver opium -> morphine, codeine (strong medicinal
pain)
Ergot fungus > ergotamine (headache), ergometrine
(direct action on uterine muscle)

Digitalis foxglove -> digoxin

(acts on cardiac muscle)

2. Source of complex molecules that can be

modified to medicinal compounds
Examples:
Droscera yam: molecule -> steroids
Soya: saponins -> steroids

3. Source of toxic molecules

To study the way the body responds to their
pharmacological use
Investigating pharmacological mechanisms
picrotoxin nerve conduction

4. Source of compounds to use as

templates for designing new drugs
Morphine:
No better painkiller. Once structure worked out wanted
to improve it. What is required?
Diacetylmorphine (heroin):
OH group -> O-O-diacetyl. Still addictive?
Codeine:
Methylate hydroxyl phenolic; O-Me. 1/5 analgesic
capacity of morphine, useful to suppress cough reflex
Dihydromorphinone:
Reduced =, oxidised 2y alc. Potential analgesic.

Dihydrocodeine:
Me-ether of previous. More powerful than codeine,
less than morphine.
Dextromethorphan:
Good against cough reflex

Is lower ring necessary?

Is middle ring needed?

Pentazocin

Pethidine

Phenazocine

Methadone

 5. Source of novel structures

these might never be thought of
Catharanthus periwinkle -> vincristine (alkaloid dimer)

 6. Source of plant drugs

As a powder or extract
The pure compound is often not isolated because:
Active ingredient is unknown
Active ingredient is unstable
Isolation process is too costly

 250,-500,000 species of higher plants on earth

<10% investigated and only for one activity
Huge potential in plant kingdom
Future: intense screening

Anticancer - NCI
Antimicrobial
Antiviral
Antimalarial
Insecticidal
Hypoglycaemic
Cardiotonic
Antiprotozoal
Antifertility - WHO

 Screening
Pharmacological in vitro testing
Chemical certain constituents Eg alkaloids

Failed screening work

Incorrect identification of plant material
Plants exist in chemical races different
constituents
Low yield of active compound
Solubility have to find correct solvent

Future
80% world population rely on natural
remedies
Westernization of societies
(traditional knowledge)

Extermination of species
conservation, retain gene pools

Natural resources exhausted

cultivation, artificial propogation

Conclusion
Natural products very important to
medicine
Exist in range of structures that one
wouldnt think of synthesizing
Can act as templates for new drug
development
Untapped reservoir of new compounds