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Botany - Topic list A > Topic 11 - The major groups of azotoids > Flashcards

Topic 11 - The major groups of azotoids Flashcards

1
Q

Azotoids

A

Compounds derived from nitrogen metabolism

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2
Q

Types of azotoids

A 
Universal azotoids
Simple specific azotoids
Cyanogenic compounds
Glucosinolates
Alkaloids
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3
Q

Universal azotoids

A

Universal proteinogenic amino acids and metabolic intermediates (e.g. ornithine)

Universal amino acid derivatives - chlorophyll, auxins

Proteins (polypeptides and glycoproteins →lectins)

Universal purine and pyrimidine nucleotides (ATP, GTP, CTP, UTP, TTP) and derivatives (NAD, FAD, CoA)

Nucleic acids

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4
Q

Lectins

A

Specific glycoproteins (protein + oligosaccharide chain)

Bounds with the cell membrane

Ricine and abri toxalbumin - a disulfide bond connects two polypeptide chains

Fazin in bean species

Viscumine in misteltoe

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5
Q

Non-proteinogenic amino acids

A

About 200-400 biogenic amino acids

Never found in the protein structure, but perform several biological functions

Derived from universal amino acids with N, S and C, or stereoisomer molecules

Natural occurrence mainly in Fabaceae family

e.g. Lathyrogenes ro canavanine

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6
Q

Biogenic amines and amides

A

Simple specific azotoids

Nitrogenous compounds derived from amino acid by decarboxylation

With various biological effects

Tryptamine, phenethylamine – psychoactive and simulant effect, increased heart functions

Histamine – local immune and inflammatory response (e.g. nettle)

Alliin – in the garlic

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7
Q

Cyanogenic compounds

A

Biosynthesised from aliphatic or aromatic amino acids

In glycosidic form

Widely distributed in the plant kingdom, as a defense mechanism against herbivores and pests

Upon plant injury, specific enzymes remove the sugar parts aglycones are activated and HCN is often produced spontaneously poisoning

E.g. amygdalin, lotaustralin, linamarin, dhurrin, taxiphyllin, prunasin

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8
Q

Glucosinolates

A

Biosynthesised from amino acids glucose bounds with S-glycosidic bond (thioglycoside) and with another sulphate group

Natrual occurrence only in a few families, mainly Brassicaceae

Hydrolysis results isothiocyanates (mustard oil) goitrogen effect

E.g. sinigrin, sinalbin

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9
Q

Alkaloids

A

Specific, mainly alkaline plant metabolites with a nitrogen content

Products of the nitrogen metabolism

Approximately 21 000 different alkaloids described from 4000 plant taxons

Stored in vacuoles

Even a small dose can lead strong biological effects

Plants are able to decompose the stored alkaloids and re-use them again

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10
Q

Plant families with characteristic alkaloids

A 
o	Papaveraceae
o	Ranunculaceae
o	Fabaceae
o	Apocyanaceae
o	Asclepiadaceae
o	Solanaceae
o	Liliaceae 
o	Amaryllidaceae
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11
Q

Alkaloids derived from amino acids

A

True alkaloids

Protoalkaloids

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12
Q

Alkaloids not derived from amino acids

A

Pseudoalkaloids:

  • Nucleotide alkaloids
  • Terpenoid alkaloids
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13
Q

Major effects of alkaloids

A

Stimulate the CNS – caffeine

Paralyze the CNS – scopolamine

Stimulate the PNS – efedrin

Paralyze the PNS – hyoscamine

Vasoconstrictor effect – ergot alkaloids

Vasodilator effect – theophylline

Increase blood pressure – vincamine

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14
Q

True alkaloids dervied from ornithine, lysine and nicotinic acid

A

Tropane alkaloids

Pyrrolizidine alkaloids (PA)

Quinolizidine alkaloids

Piperidine alkaloids

Pyridine alkaloids

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15
Q

Tropane alkaloids

A

Natural occurrence: Solanaceae, Erythroxylaceae, Convolulceae

Major alkaloids are S and R hyoscyamine, scopolamine and cocaine

Ecgonine alkaloids (tropane derivates)

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16
Q

Muscarinic cholinergic receptors

A

competitive antagonist of acetylcholine

Inhibition → anticholinergic effects

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17
Q

Cocaine

A

Block ion channels in neurons → local analgesic, and strong (psycho)stimulant effect

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18
Q

Pyrrolizidine alkaoids

A

Natural occurrence: Heliotropium spp., Cyneglossum spp., symphytum spp., Senecio spp., Eupaotrium spp.

At least 560 types described → most important: jacobins and senecionine

Hepatotoxic effect → secondary photosensitisation

Accumulation in organs

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19
Q

Quinolizidine alkaloids

A

Natural occurrence: Fabaceae family (esp. lupines, cytisus, laburnum genera)

No accumulation in organs

Binding to nicotinic receptors as ACh agonists

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20
Q

effects of quinolizidine alkaloids

A

Inhibits phenylalanine tRNA binding to ribosomes and interfere with aspects of translation

Tetratogenic, antibacterial, anti fungal activity

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21
Q

Major quinolizidine alkaloids

A 
Sparteine
Cytisene
Lupinine
Lupanine
Anagyrin
22
Q

Lysine derived Piperidine alkaloids

A

Lobelia alkaloids

Piperine alkaloids

23
Q

Lobelia alkaloids

A

Respiratory and ganglionic stimulants → open nicotinic ACh receptors → nicotine-like, but weaker effect

24
Q

Piperine alkaloids

A

An amide of piperidine: responsible of pungency of black pepper depressant and anticonvulsant effect

25
Q

Non-lysine derived piperidine alkaloids

A

Piperidine alkaloids → pseudoalkaloids

26
Q

Piperidine alkaloids

A

Lysine derived

Non-lysine derived

Conium alkaloids

27
Q

Conium alkaloids

A

Absorbed through the skin, mucous membranes and it can cross the placenta

In the peripheral nervous system coniine block the nicotine receptors on the post-synaptic membrane of neuromuscular junctions → blocking movements

28
Q

Pyridine alkaloids

A

Synthesised from nicotinic acid → the heterocyclic ringed, nitrogen containing nucleus is unsaturated

Widely distributed in nature, provide aroma of food stuffs

29
Q

Use and effects of pyridine alkaloids

A

Natural insecticides → Synthesis increase after insect attack

Respiratory stimulant, but larger dose causes respiratory depression

Nicotine acts as an agonist at nicotinic acetylcholine receptors

30
Q

Major pyridine alkaloids

A

Nicotine, anabasine, arecholine

31
Q

True alkaloids derived from phenylalanine and tyrosine

A

Isoquinoline alkaoids

Benzylisoquinoline alkaloids

Phenylethylisoquinoline alkaloids

32
Q

Isoquinoline alkaoids

A

Two six membered aromatic rings with nitrogen

Various effects:

  • Antispasmodic
  • Antibilious but also cytotoxic → anti-tumor drugs
33
Q

Major isoquinoline alkaloids

A

Cheliodnine
Chelerythrine
Sanguinarine

34
Q

Benzylisoquinoline alkaloids

A

Synthesised from two units of tyrosine

Important as medicine, but large dose can be highly toxic

Act on the opioid receptors: suppression of transmission of pain signals

Carcinogenic effects

35
Q

Types of Benzylisoquinoline alkaloids

A

Papaverin: basic Benzylisoquinoline backbone

Morphinian derivates: opiates

Codeine and noscapine: antitussive effect (cough suppressive)

Morphine and thebaine: painkillers, sedative

36
Q

Phenylethylisoquinoline alkaloids

A

Small group with only a few molecules

Treatment of gout

37
Q

colchicine

A

binds with tubulin dimers → inhibition of microtubule formation → inhibition of cell division

38
Q

True alkaloids derived from tryptophan

A

Quinoline alkaloids

Indole alkaloids

39
Q

Quinoline alkaloids

A

Nitrogene in different position than isoquinoline alkaloids

With a monoterpenoid chain (C10)

The most important antimalarial drugs

Quinine (Cinchona officinalis)

40
Q

Indole alkaloids

A

Simple indole derivates or isoprenoid alkaloids with a C9 or C10 monoterpenoid fragment

Molecules are similar to serotonin, dopamine and epinephrine → bind to receptors as agonists

41
Q

Effect of indole alkaloids

A

Vasodilator effect → increased blood and oxygen supply to the brain

Cytotoxic activity → anticancer drug

Psilocybin → psychedelic compound

Vasoconstrictor, styptic and psychedelic effects

42
Q

Protoalkaloids

A

N atom derived from an amino acid but it’s not of the heterocyclic

43
Q

Types of protoalkaloids

A

Ephedrine: a bronchodilator with psychostimulant effect, act as adrenaline

Mescaline: strong hallucinogene effect

Cathinone: amphetamine-like effect, psychostimulant

Capsaicin: active component of chili peppers

44
Q

Pseudoalkaloids

A

The classification based on the precursor molecule

The backbone not derived from the nitrogen pathway the nitrogen incorporated in a different way

45
Q

Terpenoid alkaloids

A

Monoterpenoid alkaloids

Diterpenoid alkaloids

(Triterpene) Steroid alkaloids

46
Q

Diterpenoid alkaloids

A

Various molecules due to the basic terpenoid structure

Nitrogen bounds with amination (an amine group introduction to the molecule)

Affects ion channels → CNS and cardiac effects

47
Q

(Triterpene) Steroid alkaloids

A

Steroidal backbones are triterpene derivates, nitrogen bounds with amination

Many of them occur as glycosides

Open Na+ channels permanently – paralyzing effect

48
Q

Alkaloids derived from nucleotids

A

Purine alkaloids
Pyrimidine alkaloids
Pyridine alkaloids

49
Q

Purine alkaloids

A

Synthesised from purine nucleotids

Their role in plants is currently undetermined (chemical defense or allelopathic effect)

Stimulate the CNS

50
Q

Pyrimidine alkaloids

A

Synthesized from purine nucleotides

Many of them occur as glycosides

During degradation, oxidizing agents (H2O2) produced

Botany - Topic list A (17 decks)

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