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Chemistry of alkaloid
1. Chemistry of alkaloid
NORSYAMIMI BT CHE
SULAMAN (153504)
NUR FATIHAH BT ABAS
(154120)
G4
NURUL FADZILLAH BT
MOHD HATA (152266)
NOR HIDAYAT BT YUSOF
(152356)
2. INTRODUCTION
• Alkaloid~ an example of secondary metabolites
• Naturally occurring organic compounds
containing nitrogen moiety, and are usually
heterocyclic in nature.
• Contains nitrogen ~ usually derived from an
amino acid.
• Normally have a significant physiological action
on humans and animals.
3. CHARACTERISTICS OF ALKALOIDS
• Basic in nature due to the presence of
nitrogen in their ring
• Mostly obtained from plant materials.
• Have bitter tasting.
• Give a precipitate with heavy metal
iodides
• Have high pharmacological and
physiological activities.
4. Quinine •an antipyretic alkaloid
•Functional groups present in
quinine are: methoxy –OCH3,
hydroxyl –OH, tertiary amine group,
and etc
Cocaine •obtained from coca leaves.
•highly narcotic.
•stimulates the central nervous
system i.e. CNS depressant.
•can lead to psychiatric problem
when taken in high dose or when
addicted to it.
Caffeine •obtained from tea leaves.
•also a strong stimulant which can
increases alertness, thereby causing
insomnia when the body gets
addicted.
6. Occurrence of Alkaloids
• Occur in bacteria (Pseudomonas aeruginosa) and rarely
in fungi (pscilocin from hallucinogenic mushrooms).
• Some alkaloids occur in several genera from different
species (caffeine), but most occur in closely related
species.
• Some occur in certain families (hyoscyamine), while
others occur only in a specific species (morphine).
• Rarely do plants contain more than 1 type of alkaloid.
• All alkaloids of one plant will have a common
biogenenetic origin
7. • Alkaloids occur in all plant parts, but are usually
localized in one organ (e.g. the bark or seeds).
• Within the plant, [alkaloid] can vary widely from
part to part – some parts may contain no
alkaloids.
• Occasionally, different alkaloids also form in
different parts of the plant.
• Alkaloid concentrations occur in wide ranges –
e.g. Madagascan periwinkle contains 3g per (anti-
cancer) alkaloids per tonne of leaves.
8. Classification of alkaloids
Alkaloids have a large variety in their botanical &
biochemical origin, in chemical structure and
pharmaceutical action. Therefore, like flavonoids, a range
of different classification systems exist for grouping
alkaloids.
They can therefore be classified according to their
• Biological origin
• Chemical structure - 2 divisions
• i. Atypical/non-heterocyclic alkaloids (protoalkaloids or
biological amines)
• ii. Typical/heterocyclic alkaloids (divided into 14 groups
according to their ring structure)
• Biosynthetic pathway
10. Terpenoid Indole Alkaloids
• Large group of about 3,000 compounds
• Indole moiety provided by Tryptamine
(derived from Tryptophan) and a Terpenoid
component
• Moneterpenenoid indole alkaloid:
• the iridoid glycoside secologanin (derived
from the monoterpene Geraniol) and
Tryptamine
11. Benzylisoquinoline Alkaloids
• A large and diverse class present in a range of
plant families.
• The first biosynthetic step is decarboxylation of
Tyrosine by Tyrosine Decarboxylase (TYDC) to
form Tyramine.
• Coupling of two Tyramine derivatives yields (S)-
Norcoclaurine.
• Norcoclaurine is the precursor of several
thousand benzylquinoline alkaloids.
12. Tropane Alkaloids
• Plants containing these alkaloids have been used
throughout history as poisons, but many of the
alkaloids do have valuable pharmaceutical
properties.
• Known to be present in the Solanaceae family
• The TA Cocaine was found in very small amounts
in the original Coca-Cola formula, but was not the
main concern of the USDA at the time. Caffeine
was considered to be the major problem with the
drink.
Cocaine
13. Purine Alkaloids
• Caffeine the most important example in
coffee, tea, mate', cacao, camellia.
• Purine alkaloid biosynthesis starts with
xanthosine, a nucleotide degradation product.
14. Pyrrolizidine Alkaloids
• The leading plant toxins.
• Over 360 different structures, found in 3% of
the world flowering plants.
• Primarily restricted to; Boraginaceae,
Asteraceae, Fabaceae, and Orchidaceae.
• Most of them are esters of basic alcohols
known as necine bases.
15. Alkaloids in modern medicine
Atropine-antidote to nerve gas
poisoning Codeine, Morphine -Analgesic
(painkiller)
16. Alkaloids in modern medicine
Sanguinarine
Antibacterial showing
Caffeine-central nerve
anti plaque activity, used
system stimulant
in toothpastes and oral
rinses
Quinine-anti malarial, facilitated
exploration of the tropics
17. Biosynthesis of morphine
MORPHINE CODEINE
•Obtained from the opium •Occur naturally which
poppy Papaver somniferum. simply the methyl ether of
• used in medical field for morphine and converted to
relief the pain since early morphine in the body
1500s. •Used in prescription cough
medicines and as analgesic.
HEROIN
•Does not occur
naturally but
synthesized in
laboratory by
diacetylation of
morphine.
19. (S)-Reticuline: the Chemical Cameleon
(twisted and turned before being oxidized to generate different structures)
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