Medicinal Plants

David S. Seigler
Department of Plant Biology
University of Illinois
Urbana, Illinois 61801 USA
seigler@life.illinois.edu
http://www.life.illinois.edu/seigler

Outline:MedicinalPlants
Importance
o Primitive cultures
+ Link to religion
+ Link to psychoactive drugs
Economics
Botanical
o Many families

Chemical
o Terpenes
+ Cardiac glycosides
+ Steroids
+ Metabolically altered
triterpenes
o Alkaloids
+ Analgesic drugs
+ Antitumor drugs
+ Emetics

o Anthraquinone glycosides
+ Laxatives
o Polyketides
+ Aspirin
o Mode of action
Herbal medicines

Reading

CHAPTER 11, pp. 262 ff.

Introduction
The use of medicinal plants is
found in almost all cultures. In
some, many types of plants are
used. Some are efficacious and
others are not.
The science of botany originated
in the study of medicinal plants.
Chemistry, botany, and medicine
were all considered one field
until the 1700's.

HerbalmedicinesinMadagascar

CourtesyDr.VoaraRandrianasolo

MedicinalplantsinTolucamarket

 Many plant and fungal

derivatives are important
medicinally.
The most important of the plantderived compounds are terpenoids
(such as steroids) and
alkaloids.
Substances such as anthraquinone
glycosides as well as a variety
of other types of glycosides are
also widely used.

 These include the active

principles of Salix (Salicaceae),
Artemisia cina (Asteraceae or
Compositae) (santonin used as an
anthelmintic drug), quassia (used
to control lice etc.).
Table of some important medicinal
plants on page 263.

 Presumably curative agents were

discovered by trial and error.
Sumerian drawings of opium from
2500 B.C. suggest that they were
knowledgeable about medicinal
plants.
In 1770 B.C., from the Code of
Hammurabi, a series of plants such
as henbane (Hyoscyamus niger,
Solanaceae), licorice (Glycyrrhiza
sp., Fabaceae), and mints (Mentha
spp., Lamiaceae) were mentioned.

 The ancient Egyptians

recorded much of their
knowledge of plant drugs as
well. Many of the plants used
by them are still used in
medicine.

TheGreeks
The Greeks made other significant
contributions to medicine.
The number of effective medicinal
plants came to be about 300-400
species.
Hippocrates (460-377 B.C.),
Aristotle (384-322 B.C.) and
Theophrastus (372-287 B.C.)
essentially started the science of
botany.

Dioscorides
The most significant contribution
however, was Dioscorides (ca. 4090 A.D.) He wrote a 5 volume work,
De materia medica, that became the
standard work for 1500 years.
Because of later historical
developments and the fact that
Europe went into intellectual
decline, the book was blindly
followed and accepted without
question until the fifteenth
century.

Doctrine of Signatures
Finally, a contemporary of da Vinci,
Paracelsus (1393-1451), broke
publicly with the works of the Greeks
and advocated the "Doctrine of
Signatures". This was soon displaced
by more objective methods.

 In the 19th century, such

compounds as quinine, strychnine,
morphine, and ephedrine were
isolated and studied.
Later (mostly in the twentieth
century) many of the compounds
were synthesized and some became
available from that source.

 Most of the drugs used in

western culture come from
Europe and Asia, although a
number of extremely important
ones come from other sources.

Types of active compounds

The most important types of
compounds are terpenoids and
alkaloids. Others such as fatty
acids (e.g., chaulmoogra oil) are
also used, however.
The chemical structures of
several important drug materials
are given in this chapter.

Malaria and quinine

Historically, malaria has been one
of the worst of all human diseases.
In some countries malaria is common
and millions of people suffer from
the disease throughout the world.
Malaria is caused by a sporozoan of
the genus Plasmodium and is passed
from one human to another by
mosquitoes.

 In the 17th century, Jesuits in

South America discovered that a
native remedy for other
diseases made from an infusion
of the bark of cinchona
(Cinchona spp., Rubiaceae)
coincidentally controlled
malaria.

Peruintheearly1940s

CourtesyDr.WalterHodge

Quinine,Cinchona
officinalis,Rubiaceae
Calisayatype

CourtesyDr.WalterHodge

Harvestingcinchona
bark

CourtesyDr.WalterHodge

Dryingandstoring
cinchonabark

CourtesyDr.WalterHodge

TypesofCinchonabark

CourtesyDr.WalterHodge

 The Dutch acquired seeds from a highyielding plant near Lake Titicaca,
Bolivia. After several years of trying
to grow the plants and improve them,
they were able to begin to cultivate
high quality lines in the Dutch East
Indies and eventually they got a
monopoly on the production of quinine.
At the time of W.W. II, the allies
were cut off from a supply of quinine.
During the war, a number of synthetic
substitutes for quinine were
developed. Many are still important,
but resistance to most is a major
problem.

 Quinine is also used in small

amounts to make tonic water
and other soft drinks such as
bitter lemon.
Although there have been
extensive searches for new
plant-derived antimalarials,
few have surfaced.
One, artemisinin from
Artemisia annua, has proven
effective and is currently
being used in southeast Asia.

Artemisiaannua,
Asteraceaeor
Compositae

Ephedra or ma huang, Ephedra spp.,

Ephedraceae
Infusions of Ephedra spp.
(Ephedraceae, a gymnosperm) have
been used for thousands of years
in China. There it is often
called "ma huang".
In the 1920's the plant was
"discovered" by western medicine
and the active compounds
isolated.

Ephedra,Ephedrasp.,Ephedraceae

 Ephedrine and a series of

related compounds are used
today as decongestants (e.g.,
in Sudafed, Robitussin etc.)
and to treat low blood
pressure.
Most of the active compounds
are made synthetically,
however.

Willows and aspirin

Even in the time of Dioscorides it
was known that extracts of willow
bark (Salix spp., Salicaceae) and
leaves alleviated pain.
The compound that is responsible is
called "salicin". Salicin is too
irritating to take internally,
however.
In the late 1800's, a German chemist
made another compound that could be
taken readily and that had similar
properties to salicin.

Willowinflower,Salix
nigra,Salicaceae

 This compound, acetylsalicylic acid,

could be taken orally and was an
effective analgesic, antiinflamatory, and antipyretic drug
and is probably the most widely used
drug in the world today.
Interestingly, we only learned how
aspirin actually functions in the
last 30 years. Aspirin inhibits the
synthesis of certain prostaglandins.

Coca and cocaine

The Indians of Andean South America
have long used coca leaves (from
Erythroxylum coca, Erythroxylaceae)
as a stimulant. The Indians chewed
the leaves mixed with lime to free
the alkaloids. The alkaloids reduced
feelings of hunger and pain.
Later when the alkaloids were
isolated, it was discovered that
they had local anesthetic
properties. Cocaine has been used
for surgery (especially dental
surgery).

Coca,Erythroxylum
coca,Erythroxylaceae

Steroids from plants

Many types of animal hormones are
steroids. Although the steroids
from plants are similar, most do not
have pronounced hormonal activity in
animals and ordinarily must be
chemically modified before use.
The most commonly used plant source
of steroids is Dioscorea spp.
(Dioscoreaceae). These are viny
plants with large tuberous roots.
Diagram p. 277.

 These steroids occur as complex

glycosides (that is, they have sugars
attached) that give them soap-like
properties and are sometimes called
saponins. These compounds are
relatively common in plants.
Dioscorea species are used because
they have relatively large amounts of
saponins and the structure of the
aglycone is particularly appropriate
for conversion to the desired
steroids.

Maleandfemale
Dioscoreaplants

Disocorearoot

 Steroids from these plants are

converted chemically into
hormonally active substances that
simulate pregnancy and serve as
antifertility or contraceptive
compounds or as anti-inflamatory
drugs such as cortisone etc. that
are used to treat a number of
diseases such as arthritis etc.

Cardiac glycosides
The use of plants to treat heart
disease goes back thousands of
years and is found in several
cultures. One of the plants found
in the folk medicine of Europe is
Digitalis purpurea
(Scrophulariaceae).

Digitalis,
Digitalis purpurea
(Scrophulariaceae)

 In 1775, William Withering, a

British physician documented that
patients treated with foxglove
improved. He standardized the
dosage of the drug.
Diagram p. 277.
Digitalis became accepted and
today is widely used in treatment
of dropsy, a condition associated
with congestive heart failure.
The active compounds are saponins,
but have an aglycone with a
special type of structure.

Opium poppy, Papaver somniferum

(Papaveraceae)
The alkaloids found in opium poppy,
Papaver somniferum (Papaveraceae),
have long been used to alleviate pain.
See diagram of the plant on page 279.
Capsules have been found in
prehistoric deposits from the
Mediterranean and from the Near East.
Pictorial representations are found in
Egyptian, Greek, Roman and other art.
Opium was used to treat dysentery from
at least the first century B.C. The
wild ancestor of the plant is no
longer known with certainty.

Poppyflowerandcapsule

CarolinaBiologicalSupplyCo.

 Opium is isolated by lightly slashing

the immature fruit capsules. The
latex oozes out and hardens after a
day or so. The latex is about 11%
morphine and 1% codeine. The exudate
is scraped off and made into bricks
of pure opium. The yields are 25-40
lbs. per acre.
Morphine is one of the principal
alkaloids of opium. These alkaloids
are very addictive, but are potent
pain killers (analgesics).
Codeine, another morphine alkaloid,
is a potent antitussive agent, that
is, it inhibits coughing.

Incisedpoppycapsuleandlatex

CarolinaBiologicalSupplyCo.

 Morphine is acetylated to produce

heroin.
Poppies are also cultivated for the
seeds which are eaten and are used as
an oilseed crop in some countries.
Opium played a role in the history of
China and (especially) British
colonialism in the last two or three
centuries.

Tropane alkaloids
A number of alkaloids from
solanaceous plants are used as
analgesics.
See p. 280.
The most commonly used alkaloids
are scopolamine (hyosine),
hyoscyamine, and atropine.
The most commonly used plants are
Atropa belladonna, Hyoscyamus
niger, and Duboisia species (the
last species native to Australia).

Henbane,Hyoscyamus
niger,Solanaceae

Jimsonweed,Datura
stramonium,Solanaceae

 Belladonna has been used since the

times of the Greeks. It was also
used in the Middle Ages in Europe to
enhance the appearance of women by
causing them to have large pupils.
Today, these alkaloids are used as
antidotes for poisoning, to treat
cardiac problems, for antidiarrhetic
preparations, and to dilate pupils
during eye examinations.

Blacknightshade,
Atropabelladonna,
Solanaceae

RauvolfiaAlkaloids
A number of plants of this group
were used medicinally in India
several centuries BC.
One of these plants is Rauvolfia
serpentina (Apocynaceae). This plant
contains alkaloids that are
extremely potent hypotensive agents.
One of the main alkaloids,
reserpine, is used to treat
hypertension and certain types of
mental illness. Relatively large
doses are used to treat
schizophrenic patients.

Rauvolfia
serpentina
(Apocynaceae)

Catharanthusalkaloids
Two complex alkaloids of
Catharanthus roseus (Apocynaceae)
are used to treat leukemia.
Vinblastine and vincristine
produce remissions or cures in up
to 50-70% of cases in certain
forms of leukemia. In lymphocytic
leukemia, even higher cures are
reported.

Periwinkle, Catharanthus roseus

(Apocynaceae)

Colchicine

Colchicine, an alkaloid from

Colchicum autumnale
(Liliaceae), is used to treat
gout. The compound is fairly
specific for the disease, but
is highly toxic and its use
must be carefully monitored.

Autumn crocus, Colchicum autumnale

(Liliaceae)

R.BentleyandH.Trimen,MedicinalPlants, London,
Churchill, 1880.

Anthraquinoneglycosides

Anthraquinone glycosides from

a number of plants [including
Aloe (Liliaceae), Rhamnus
(Rhamnaceae), Cassia
(Fabaceae or Leguminosae)]
are widely used as laxatives.
They also have other
medicinal applications.

Aloe,Aloesp.,Liliaceae

Taxol
The antitumor activity of taxol
(paclitaxel), a diterpene alkaloid
from several Taxus species, was
first discovered in the 1960's,
but the alkaloid didn't become
widely used until the mid 1980's.
Taxol is useful for treating
several types of tumors, but was
originally developed for ovarian
tumors.

 The alkaloid occurs in highest

concentration and in the most readily
purifiable form in the bark of Taxus
brevifolia, the Pacific yew.
Recently, materials from other
species of Taxus have proven useful
for sources of the drug, largely
alleviating the environmental
problems that resulted from over
harvest of the original source.

Yew,Taxusbaccata,
Taxaceae

Calabar bean,
Physostigma venenosum (Fabaceae or
Leguminosae)

Calabar beans have been used

as a trial-by-ordeal plant.
The active ingredient,
physostigmine, is presently
used to treat glaucoma.

Calabar bean,
Physostigma
venenosum
(Fabaceae or
Leguminosae)

R.BentleyandH.Trimen,Medicinal
Plants, London, Churchill, 1880

Ergot,Clavicepsspp.,Clavicepitaceae

The alkaloids from Claviceps spp.

on cereal grains have long caused
problems in human health. The
compounds are vasocontrictive and
in the Middle Ages in Europe
caused many human poisoning
problems.

Ergot,Clavicepsspp.,Clavicepitaceae

 People's hands and feet sometimes

developed gangrene when they ate
grain containing ergot.
Some of the alkaloids also cause
hallucinogenic effects and bizarre
behavior.
All together the syndrome was called
"St. Anthony's fire". The basis for
the syndrome was not understood
until about 150 years ago.
Today the alkaloids are used to
treat migraine headaches, control
hemorrhaging after childbirth, and
to induce labor.

Herbalmedicines

 Today, in Western Culture, most of the

active ingredients are isolated,
purified, and standardized, or ...
ironically (in the U.S.) are sold in
"Health Food" stores with little
assurance that the plant materials are
pure, contain the active principles,
or are effective. Recent changes in
FDA regulations promise to improve
this situation.

 In Europe, particularly in
Germany, companies that market
herbal medications are required
to establish efficacy and to
provide the materials in a form
that ensures that the active
materials are present in a
designated dosage. However, in
many cultures, the crude plant
drugs are still used directly.

HerbalmedicinesinaMexicanmarket

St. John's wort, Hypericum

perforatum, Clusiaceae
St. John's wort, Hypericum
perforatum, is effective as an
antidepressant drug.
This plant is native to Europe
and Asia, but has been introduced
into North America, where it is a
common weed.

St.Johnswort,Hypericum
perforatum,Clusiaceae

Ginkgo,Ginkgobiloba,Ginkgoaceae

Extracts from the leaves of

Ginkgo biloba, a
gymnospermous tree from
China, improve capillary
blood flow and improve memory
and some aspects of brain
function. The active
components are diterpenes.

Ginkgo,Ginkgobiloba,
Ginkgoaceae

Ginseng,Panaxginseng,Araliaceae
Ginseng has long been used by Oriental
peoples as a way of maintaining health and
for treating and curing many types of
human ailments. In Japan, Korea, and
China, the most common species is Panax
ginseng.
Because of the shape of the roots, based on
the doctrine of signatures, this plant was
presumed to treat many problems.
The Eastern North American species, Panax
quinquefolia, was one of the earliest
exports from the American Colonies to the
Orient. The
active compounds are
triterpenoid glycosides; some are called

Ginseng,Panaxginseng,
Araliaceae

Takatori. Color Atlas of

Medicinal Plants of Japan.

Echinacea,Echinaceapurpurea,Asteraceae
Echinacea was used as a medicinal plant by
American Indians. The plant was
introduced into patent medicines in the
1870s and has been used since that time to
deal with a number of problems.
Echinacea was an important plant medicine
in the 1920s, but fell into disuse as
antibiotics of various types were
introduced.
Echinacea induces an immune response in
humans
and has been used more recently to treat
colds and other viral diseases.
This plant drug is especially popular in
Europe. As the plant is often wild

Echinacea,Echinacea
purpurea,Asteraceae

Valerian,Valerianaofficinalis,Valerianaceae
Valerian has long been used as a sedative.
The dried roots and rhizomes have been used
as a tranquilizer and calmative for more
than 1000 years in cases of nervousness and
hysteria. The plant parts have a somewhat
disagreeable odor.
Interestingly, in this case, the active
components have never been conclusively
identified. However, the plant is
documented to be an effective sleep-inducing
drug.

Valerian,Valeriana
officinalis,
Valerianaceae

Blackcohosh,Cimicifugaracemosa,
Ranunculaceae
The underground parts of
Cimicifuga racemosa are used to
treat a number of female
problems.
This plant was used by many of
the American Indians of the
Eastern United States.

Blackcohosh,Cimicifugaracemosa,
Ranunculaceae
An infusion of the roots and
rhizomes is drunk to treat
rheumatism, uterine difficulties to
stimulate menstrual flow, and as an
antidiarrheal, and cough
suppressant.
It was the active component of Lydia
Pinkhams Vegetable Compound in the
1800s and early 1900s.
The plant has been shown to have
estrogenic activity and is used in
Europe to treat premenstrual
syndrome (PMS).

Blackcohosh,Cimicifuga
racemosa,Ranunculaceae