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BVB221 NATURE'S PHARMACY > Alkaloids > Flashcards

Alkaloids Flashcards

1
Q

most important and common feature of alkaloids

A

they contain an nitrogen atom in a heterocycle and bitter tasting and basic

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2
Q

typical alkaloids are …

A

derived from plant sources
they are basic
contain one or more nitrogen atoms
have a physiological action on humans or other animals

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3
Q

examples of common alkaloids

A

caffeine and nicotine

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4
Q

important families of alkaloids

A

apocyanceae (Dogbane)
Papveraceae (Poppy)
Fabaceae (leguma, pea)
Ranunculaceae (Buttercup)
Rubiaceae (Coffee, Madder)
Rutaceae (Rue or Citrus)
Solonaceae (Nightshades)

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5
Q

applications of alkaloids

A

medicinal - virtually every pharmaceutical applicaiton imaginable except antibiotic
agriculture - insectisides and veterinary
culturl/entheogenic - most often to idnuce an altered state of consiousness.
recreational - nicotine

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6
Q

testing for alkaloids

A

mayer’s - cream colour
dragendorffs’s - orange
wagner’s reagent - red/brown
hager’s reagent - yellow

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7
Q

physicochemical properties

A

most alkaloids that don’ contain oxygens are liquid at room temp
insoluble in water
soluble in polar or slightly polar organic solvents

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8
Q

how are alkaloids classified

A

according to their origin
eg acontium, amaryllidaceae, ergot, opium etc

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9
Q

chemical classification

A

True alkaloid
Proto alkaloid
Pseudoalkaloids
False Alkaloids

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10
Q

what are true alkaloids

A

they are derived from an amino acid and have a nitrogen in a heterocyclic ring

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11
Q

what are proto alkaloids

A

they are derived from an amino acid but their nitrogen atom is not in the heterocyclic ring

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12
Q

what are pseudo alkaloids

A

they are not derived from amino acids but the nitrogen atom is in the heterocyclic ring

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13
Q

what type of derived alkaloids are there

A

there is tryptophan, Phenylalanine/ tyroise

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14
Q

what pathway and compound produce the precursor for the derived alkaloid pathway

A

the shikimata pathway with the compound chroismate.

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15
Q

indole alkaloids

A

tryptophan poduct of tryptamine give rise to the indole alkaloids.
these contian 2 nitrogen, on is indolic nitrogen and the second is generally two carobons removed from the b-position of the indole ring.

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16
Q

what determines the type of alkaloid produced for the tryptophan reactions

A

condensation between tryptamine and an aldehyde or a keto acid.
with the rection either occuring at the alpha or beta carbon.

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17
Q

what terpene pathway is also used for alkaloids

A

the mevalonate pathway as it is used for non-trypotophan derived

18
Q

what families does a c10 monoterpenoid provide

A

the apocynaceae. loganiaceae and rubiaceae

19
Q

example of tryptophan derived alkaloid

A

physostigmine
used to treat glaucoma
originally used as a poison

20
Q

ergotamine

A

is a tryptophane derived alkaloid,
structural similiarity to several neurotransmitters
functions as a vasoconstrictor
used to treat acute migraine

21
Q

vinblastine

A

tryptophane derived,
obtianed from Catharanthus roseus (madagascar periwinkle)
a funsion of two alkaloid precursors
potent mitotic inhibitor used to treat a umber of types of cancer

22
Q

phenylalanine and tyrosine are ?

A

essential, aromatic amino acids

23
Q

benzylisoquinoline and opium are

A

well known derivatives of aromatic amino acids

24
Q

amaryllidaceae alkaloids

A

well known for toxic properties
derived from one phenylalanine and one tyramine
represented by haemanthamine, lycorine, galantamine
potential treatment of galanthamine

25
Q

Tetrahydroisoquinoline

A

derive from the condensation of dopamin with secologanin (c10 monoterpene)
cephaelis gives ipecacuanha root

26
Q

emetine

A

earliest use of emtine is an emetic.
antiprotozoal,

27
Q

Ornithine-derived alkaloid

A

the amino acid ornithine, makes the decarboxylation product putrescine, and proline constitute the basic unit of tropane, ecgonine, nicotine and others

28
Q

what are the two major ornithine-derived alkaloid groups

A

tropane and pyrrolizidine

29
Q

Tropane alkaloid

A

medical interest in atropine and hyoscine
these are both contained to nightsades

30
Q

Atropine

A

comes from deadly nightshade, dilates the pupils, increase heart rrate, reduces salvation and other secreations
used to treate nerve gas poisoning

31
Q

Hyoscine

A

antispasmodic used to prevent postoperative nausea and vomiting, treat gatrointestinal spasms,

32
Q

Pyrrolizidine alkaloids

A

constitute the natural biocides from plants of genus senecio. these are well known for their toxicity to livestock

33
Q

Piperine

A

used for cholera, dyspepsia

34
Q

Cytisine

A

also known as baptitoxine or sophorine
currently used as an alternative to nioctine in replacement therapy

35
Q

Biosynthesis of Protoalkaloid

A

derived from amino acids but do not have the nitrogen in a heterocyclic ring
are typically classified by what amino acid they came from

36
Q

Ephedra species

A

original source of ephedrine and pseudoephedrine

37
Q

Extraction methods for Alkaloids

A

Acidic or Basic
choice depends on the chemical state of the particular alkaloid

38
Q

sample preparation

A

defatting using a non polar solvent which removes the interfering compounds

39
Q

Basic Extraction

A

Moistend with water and mixed with a base so alkaloid is released.
organic solvents used for extraction by seperation. alkaloid salts igrate to teh aqueous phase.

40
Q

Acid Extraction

A

moistened with water or aqueous alcohol. unwatned materials removed with shaking with chloroform.
free alkaloids are precipitated by the addition of excess sodium bicarbonate or ammonia and separated with filtration

BVB221 NATURE'S PHARMACY (10 decks)

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