292
Chapter 16 · Nature’s Pharmacy - Natural Pharmaceuticals
16
from coffee beans by “distraction”, i.e.
by extraction with supercritical carbon
dioxide; alternatively there is also a
five-stage chemical synthesis.
5 Quinine, an alkaloid of the quinoline
type, is obtained from the bark of the
quinine bark tree. For a long time, it was
the only known anti-malaria drug. Today
it is used especially in soft drinks. The
required quantities are still obtained by
extracting the bark.
5 Morphine comes from opium, the dried
latex of the opium poppy. It is a very
powerful analgesic and intoxicant that
leads to addiction. Morphine is also an
alkaloid and belongs to the isoquinoline
group. Since the enantioselective
synthesis of the natural (-)-morphine is
very complex, it is still being isolated
from opium.
5 Penicillins and cephalosporins belong
to the β-lactam antibiotics used for
the treatment of infectious diseases.
They are produced biosynthetically
in fermentation processes using
microorganisms. In “partial-synthetic”
antibiotics, the substituents on the two
basic structures are later chemically
varied.
5 Steroids belong to the group of lipids
and contain the tetracyclic sterane as
their basic structure. Their biosynthesis
takes place from terpenes, e.g. squalene,
via cyclization reactions. Natural
steroids are present in small amounts
in numerous animals, plants and fungi.
Cholesterol is an important steroid in the
human body.
5 Steroid hormones include cortisol,
which is essentially involved in
controlling metabolism, the male sex
hormone testosterone and the female
sex hormones, estrogens and gestagens.
In recent decades, several generations of
contraceptives have been developed on
the basis of these hormones.
5 The first-generation contraceptives contained
relatively high doses of estrogen and gestagen,
leading to an increased risk of thrombosis.
5 In the second generation, levonorgestrel has
been used as gestagen since 1966. It can
also be used as the sole active ingredient in
minipills. In high doses, it is also used as a
“morning after pill”.
5 In the third generation, desogestrel was used
as gestagen. It can be used in very small
doses. In the 1990s, it was the world’s leading
contraceptive.
5 The “pill” of the most recent generation
contains drospirenone, which is characterized
by a very reliable efficacy and low side effects.
Chemically remarkable are the two cyclopropane rings and the spirolactone.
Great progress has been made in the development of contraceptives in recent decades. However, the synthesis of these substances is relatively
complex and therefore expensive. An active substance that could also be applied in poorer countries would be highly desirable.
Summary (Take-Home Messages)
5 Natural pharmaceuticals have been
used by mankind for thousands of
years. Today’s pharmaceutical industry
is still looking for new active ingredient
structures from nature.
5 The analgesic and antipyretic Aspirin
consists of acetylsalicylic acid. The natural
model was salicylic acid, which occurs in
willow bark. Today the chemical synthesis
takes place according to the “Kolbe–
Schmitt method” from sodium phenolate
and carbon dioxide under pressure.
5 Many natural active ingredients
were combined to form the group
of alkaloids. Due to their nitrogencontaining skeletal structures, they have
an “alkali-like” behavior, which led to
their group name.
5 The stimulant caffeine is an alkaloid of
the xanthine group. It can be extracted
Chapter 16 · Nature’s Pharmacy - Natural Pharmaceuticals
16
from coffee beans by “distraction”, i.e.
by extraction with supercritical carbon
dioxide; alternatively there is also a
five-stage chemical synthesis.
5 Quinine, an alkaloid of the quinoline
type, is obtained from the bark of the
quinine bark tree. For a long time, it was
the only known anti-malaria drug. Today
it is used especially in soft drinks. The
required quantities are still obtained by
extracting the bark.
5 Morphine comes from opium, the dried
latex of the opium poppy. It is a very
powerful analgesic and intoxicant that
leads to addiction. Morphine is also an
alkaloid and belongs to the isoquinoline
group. Since the enantioselective
synthesis of the natural (-)-morphine is
very complex, it is still being isolated
from opium.
5 Penicillins and cephalosporins belong
to the β-lactam antibiotics used for
the treatment of infectious diseases.
They are produced biosynthetically
in fermentation processes using
microorganisms. In “partial-synthetic”
antibiotics, the substituents on the two
basic structures are later chemically
varied.
5 Steroids belong to the group of lipids
and contain the tetracyclic sterane as
their basic structure. Their biosynthesis
takes place from terpenes, e.g. squalene,
via cyclization reactions. Natural
steroids are present in small amounts
in numerous animals, plants and fungi.
Cholesterol is an important steroid in the
human body.
5 Steroid hormones include cortisol,
which is essentially involved in
controlling metabolism, the male sex
hormone testosterone and the female
sex hormones, estrogens and gestagens.
In recent decades, several generations of
contraceptives have been developed on
the basis of these hormones.
5 The first-generation contraceptives contained
relatively high doses of estrogen and gestagen,
leading to an increased risk of thrombosis.
5 In the second generation, levonorgestrel has
been used as gestagen since 1966. It can
also be used as the sole active ingredient in
minipills. In high doses, it is also used as a
“morning after pill”.
5 In the third generation, desogestrel was used
as gestagen. It can be used in very small
doses. In the 1990s, it was the world’s leading
contraceptive.
5 The “pill” of the most recent generation
contains drospirenone, which is characterized
by a very reliable efficacy and low side effects.
Chemically remarkable are the two cyclopropane rings and the spirolactone.
Great progress has been made in the development of contraceptives in recent decades. However, the synthesis of these substances is relatively
complex and therefore expensive. An active substance that could also be applied in poorer countries would be highly desirable.
Summary (Take-Home Messages)
5 Natural pharmaceuticals have been
used by mankind for thousands of
years. Today’s pharmaceutical industry
is still looking for new active ingredient
structures from nature.
5 The analgesic and antipyretic Aspirin
consists of acetylsalicylic acid. The natural
model was salicylic acid, which occurs in
willow bark. Today the chemical synthesis
takes place according to the “Kolbe–
Schmitt method” from sodium phenolate
and carbon dioxide under pressure.
5 Many natural active ingredients
were combined to form the group
of alkaloids. Due to their nitrogencontaining skeletal structures, they have
an “alkali-like” behavior, which led to
their group name.
5 The stimulant caffeine is an alkaloid of
the xanthine group. It can be extracted