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alkaloids 1 Flashcards

1
Q

confers the basicity of alkaloids, facilitating isolation and purification

A

nitrogen atoms

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2
Q

low molecular weight nitrogen containing compounds

A

alkaloids

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3
Q

alkaloids came from the word

A

alkali

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4
Q

the degree of basicity of alkaloids varies greatly depending on

A

structure of alkaloid molecule

presence and location of other functional groups

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5
Q

true or false.
the biological activity of many alkaloids is dependent on the amine function being transformed into quarternary system by protonation at physiological pH values.

A

true

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6
Q

the subdivisions of alkaloids into groups are based on

A

amino acid precursors

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7
Q

true or false
the carbon skeleton of particular aa precursor is retained intact in alkaloid structure but carboxylic acid carbon is often lost through decarboxylation

A

true

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8
Q

true or false
a large group of alkaloids are found to acquire their nitogen atoms via transamination reactions, incorporating nitrogen from amino acid, while the rest of the molecule may be derived from acetate and shikimate

A

true

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9
Q

alkaloids that are terpenoid or steroid in origin are called

A

pseudoalkaloid

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10
Q

what are the alkaloids derived from ornithine

A

polyamines
pyrrolidine and tropane alkaloids
pyrrolizidine alkaloids

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11
Q

non protein amino acid that comes from the urea cycle in animals

A

L-ornithine

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12
Q

supplies the C4N building blocks

A

ornithine

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13
Q

in animals, l- ornithine is produced from ( ) catalysed by arginase

A

arginine

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14
Q

in plants, l- ornithine is formed from

A

l- glutamic acid

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15
Q

ornithine supplies C4N building block principally as

A

pyrrolidine ring

tropane ring

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16
Q

Critical regulators of cell growth, differentiation, aand cell death

A

polyamines

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17
Q

examples of polyamines

A

putrescine
spermine
spermidine

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18
Q

it is the important target for chemotherapy

A

poylamine pathway

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19
Q

up regulates P53, tumor suppressor protein

A

polyamine analogues

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20
Q

combats cancer by inhibiting proliferation of cancer cells and increase apoptosis

A

polyamine analogues

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21
Q

reduced aging of yeast cells

A

spermidine

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22
Q

characteristic odors of sperm

A

spermine

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23
Q

drug target in malaria parasite

A

spermidine synthase

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24
Q

sci name of malaria parasite

A

Plasmodium falciparum

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25
example of pyrrolidine
hygrine
26
isolated by Carl Liebermann as an alkaloid accompanying cocaine in cola
hygrine
27
it is exracted as thick yellow oil wit h a pungent taste and odor
hygrine
28
hygrine and N methyl delta 1 pyrrolinium cation inetrmolecular mannich reaction results to
cuscohygrine
29
Tropane alkaloids occur in many members of plant family
Solanaceae
30
main classes of tropane alkaloids
anticholinergics ( atropine, hyocyamine, scopolamine) | stimulants ( cocaine, ecgonine, benzoylecgonine, hydroxytropacocaine, methylecgonine cinnamate)
31
alkaloid that is synthetic precursor of atropine
tropinone
32
Tropinone gives rise to
calystegines
33
a water soluble and polyhydroxy nortropane derivatives
calystegines
34
isolated from Calystegia sepium ( convolvulaceae)
calystegines
35
Glycosidase inhibitors
calystegin A3 and B2
36
have the potential for the development of drugs with activity against AIDS virus, or HIV
calystegines
37
Formed from tropinone via tropine
hyoscyamine
38
ester of tropine with S tropic acid,whichis formed from l phenylalanine and phenyl lactic acid
hyoscyamine
39
intermediate whoch undergoes rearrangement reaction to form hyoscyamine
littorine
40
-(- hyoscine) aka
scopolamine
41
hyoscyamine and hyoscine are important alkaloids found in
``` atropa belladonna ( deadly nightshade) datura stramonium ( thornapple) hyoscyamus niger (henbane) Duboisia spevies ```
42
responsible for toxic properties of nightshade, thornapple, and henbane
hyoscyamine | hyoscine
43
Cocaine biological source
Erythroxylum coca (erythroxylaceae)
44
diester of ecgonine
cocaine
45
used as local anesthetic and illicit drug for its euphoric properties
cocaine
46
ecgonine comes from benzoyl coa derived from blank via blank
phenylalanine | cinnamic acid
47
anatoxin a is from 2 cyanobacteria
Anabaena flos-aquae | Aphanizomenon flos aquae
48
termed as very fast death factor
anatoxin a
49
powerful agonist of nicotinic acetylcholine receptor
anatoxin a
50
useful pharmacological probe for elucidating the mechanism of acetylcholine mediated neurotransmission and disease states associated with this process
anatoxin a
51
anatoxin a has what ring system
homotropane
52
T/F the reamining carbons of anatoxin a is from acetate pathway
true
53
from highly colored skin of Ecuadorian frog
Epibatidine
54
sci name of Ecuadorian frog
Epipedobates tricolor
55
epibatidine has what ring system
nortropane
56
lead compound for analgesic compounds
epibatidine
57
200-500 more potent than morphine
epibatidine
58
act as agonist of the nicotinic acetylcholine receptor not the usual opiod mechanism
epibatidine
59
pyrrolizidine is widely distributed in
Boraginaceae ( Heliotropium, Cynoglossum and Symphytum) Compositae/Asteraceae (Senecio) Leguminosae/Fabaceae (Crotalaria)
60
occurs ias free form but most in ester with mono or dibasic acids- necic acids
pyrrolizidine
61
hepatotoxic agent prolonged use as herbal remedy for inflammation, rheumatism, GIT disorder, and toxicity
acetyl intermedine/ acetyl lycopsamine
62
potent antileukemic agent
indicine n oxide
63
indicine n oxide comes from
Heliotropium indicum (Boraginaceae)
64
alkaloids derived from lysine
piperidine quinolizidine indolizidine
65
precursor for alkaloids providing 6 piperidine ring and 5 pyrrolidine ring
l lysine
66
N methyl pelletierine is present in
Punica granatum (Punicaceae)
67
having activity against intestinal tapeworms
pseudopelletierine N methy pelletierine pelletierine
68
homologue of hygriene
n methylpelletierine
69
homologue of tropinone
pseudopelletierine
70
analogue of cuscohygriene
anaferine
71
anaferine comes from
Withania somnifera Solanaceae
72
true or false benzoylacetyl coa comes from shikimate pathway by cinnamic acid
true
73
true or false 2 intermolecular mannich rxn and reduction to form lobeline and lobelanine
true
74
lobeline comes from
Lobelia inflata
75
use as for smoking cessation and anti- asthmatic
lobeline
76
sedamine comes from
Sedum acre (Crassulaceae)
77
Piperine has piperoyl coa that comes from shikimate and acetyl pathway
true
78
from black pepper
piperine
79
black pepper sci name
Piper nigrum (piperaceae)
80
used as condiment
piperine
81
forms tertiary amide as it condenses with piperic acid CoAsh ester
piperine
82
homologs of pyrrolizidine
quinolizidine
83
quinolizidine is found in
Leguminosae | Laburnum, Cytisus, Lupinus plants
84
repel feeding herbivores and responsible for human poisoning
quinolizidine
85
from lysine via cadaverine intermediate
quinolizidine
86
Lupinine is from
Lupinus luteus ( Fabaceae)
87
Sparteine is from
Cystisus scoparius fabaceae
88
indolizidine alkaloids are found in
fabaceae ( swainsona, astragalus, oxytropis)
89
hybrid of pyrrolizidine and quinolizidine alkaloids
indolizidine alkaloids
90
from lysine via L pipecolic acid
indolizidine alkaloids
91
toxic compound from Laburnum sp fabaceae
cytisine
92
castanospermine and swainsonine comes from
Castanospernum australe- moreton bay chestnut Swainsona canescens fabaceae
93
polyhydroxyindolizidines
castanospermine | swainsonine
94
inhibits glycosidase in glycoprotein biosynthesis
castanospermine and swainsonine
95
activity against AIDS
castanospermine and swainsonine
96
causes severe GIT upset and malnutrition by inhibiting hydrolase enzymes
castanospermine and swainsonine
97
alkaloids defived from nicotinic acid
pyridine alkaloids
98
aka nicotinic acid
niacin
99
important component od coenzyme NAD and NADP
pyridine units
100
in animals nicotinic acid arise from
l tryptophan
101
in plants nicotinic acid arise from
3 phosphoglyceraldehyde | L aspartate - not sure
102
nicotine comes from
nicotiana tabacum solanaceae
103
nicotine structure consists of
pyridine ring - nicotinic acid | pyrrolidine ring - L ornithine
104
nicotine is oily and volatile liquid alkaloid
true
105
comes from nicotinic acid with piperidine and pyridine ring
anabasine
106
derived from 2 moles nicotinic acid
anatabine
107
delta 3 piperideine ring of anatabine does not come from l lysine
true
108
toxic compound from castor oil ( ricinus communis euphorbiaceae)
ricinine
109
formed from dehydration of nicotinamide derivative
ricinine
110
tetrahydronicoyinic acid
arecoline
111
from betel nuts
arecoline
112
betel nuts sci name
areca catechu arecaceae
113
has stimulant effect and agonist of muscarinic receptor
arecoline
114
used as vermicide in veterinary practice
arecoline

Medicinal chemistry (6 decks)

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