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Natural Sciences Bath Final Year > Natural Products > Flashcards

Natural Products Flashcards

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1
Q

What does helodermatine do? Vaso

A

Hypotensive effect

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2
Q

What does dopamine and noradrenalin do?

A

pain and vasodilation (leading to ischemia)

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3
Q

How can DOX generate radicals?

A

NADPH dependent reduction generate semi-quinone radicals. Lead to O2 radicals and H2O2.

Association with iron from ferritin generate OH radicals

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4
Q

Name 4 improvements on DOX

A

Epirubicin - faster elimination by glucuronidation

Idarubicin - Oral administration, increased fat solubility and cellular uptake

Mitoxantrone - very toxic and selective against cancer, use different mechanism

AQ4N - activates in hypoxic cells, target solid tumours.

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5
Q

Name the 11 chemicals in doxorubicin synthesis.

A
  1. CH3CH2COSCOA + HO2CCH2COSCOA 2. 12-deoxyaklanonic acid 3. aklanonic acid/methyl ester 4. aklaviketone 5. aklavinone 6. E-rhodomycinone 7. Rhodomycin D 8a/8b/9a 9b. Carminomycin 10. Daunorubicin 11. Doxorubicin
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6
Q

What does a sting from a honey bee cause?

A

Typically anaphylaxis, high dose lead to vomitting, fever, cramps and hypotension.

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7
Q

What do helokinestatins do? vaso

A

Inhibit bradykinin and its relaxant effect

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8
Q

What does helothermine do? recep.

A

Block ryanodine receptors and calcium receptors, blocking Ca induced Ca release - lethargy, hypothermia and paralysis

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9
Q

What is interesting about gila monster venom?

A

Defensive, from a modified salivery gland and chewing.

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10
Q

What do tachykinins do? What are they?

A

inflammatory, nociceptive

Substance P, Neurokinin A+B

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11
Q

What does secapin do? (Coag.)

A

Plasmin inhibitor, preventing clot degradation.

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12
Q

Which J coupling is important?

A

2-3 = meta

7-8 = ortho

7-9 = axial (sugar)
9-11 = equitorial (sugar)
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13
Q

What are the topics of the cell receptor paragraph?

A

Helothermine (GM)

Mipartoxin (Mm-8) (CS)

Micrurotoxins (MmTX1 and MmTX2) (CS)

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14
Q

What does helothermine do? ion

A

Affect K channels, affect Ia current and action potential

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15
Q

What are the topics of the ion channel block paragraph?

A

Mast cell degranuating peptide (HB)
Tertiapin (HB)
Helothermine (GM)

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16
Q

What are the 5 steps of topoisomerase II enzymes?

A
  1. Bind helix and ATP
  2. ATP hydrolysis and double-stranded cleavage.
  3. Second helix enter in-gate, go through cleavage, exit out-gate.
  4. Re-ligase
  5. Release ADP and reset the system
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17
Q

What does polarimetry tell us?

A

That there is a chiral centre

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18
Q

How does DOX enter the nucleus?

A
  1. Diffuse into cells
  2. Associate with proteasome
  3. translocate to nucleus
  4. Dissociate and intercalate with DNA
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19
Q

What are the topics if allergic paragraph?

A

Icarapin
Vitellogenin
Procamine
Royal jelly proteins
Histamine

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20
Q

Which UV peaks are important?

A

254 benzene

300 phenol, with shift in base

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21
Q

What natural products are of use from HB?

A

Adolapin - pain killer

Melittin - anti-arthritis/inflammatory

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22
Q

What does mast cell degranulating peptide do? Ion

A

Block voltage-gated ionic channels on mast cells, affecting histamine release

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23
Q

Give the structure of idarubicin.

A

Removal of MeO on first ring

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24
Q

What does Horridum toxin do? (Spread)

A

Haemorrhagic

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25
What does a bite from a gila monster cause?
Vomitting, hypotension and chest/abdo pain.
26
Give the enzymes in order for doxorubicin synthesis.
1. dps ABCD EFGH 2. dnrG/dnrC 3. dnrD 4. dnrE 5. dnrF 6. dnmS + TDP-L-daunosamine 7. dnrP 8. doxA 9. dnrK 10. doxA
27
What are the topics of the small molecule paragraph?
Serotonin (GM HB) Dopamine/Noradrenalin (HB) Histamine (HB)
28
What does C-type lectin do? (Coag.)
Inhibit prothrombinase cleavage, prevent fibrinogen cleavage
29
What does PLA2 do? (Spread.)
Release arachidonic acid, inflammation and vasodilation. CS: myotoxic capability, less anticoagulant.
30
What do the DEPT shifts show with C NMR?
C = none none CH = up up CH2 = Down none CH3 = Up none
31
What natural products are of use from CS?
Anti-coagulant
32
If *Streptomycin* is grown on 1-14C-propionate or methyl-[14C]-methionine, which carbons are radiolabelled?
The 4th ring hydroxyl carbon.
33
What is the nmr peaks for an anomeric carbon/hydrogen?
C = 100 H = 4.9
34
What is the proteins and what percent make up CS venom?
60% - 3FT 30% - PLA2
35
If *Streptomycin* is grown on 1-[13C]acetate, which carbons are radiolabelled?
The carbon linking the sugar, then every other one. Not including the 4th ring hydroxyl carbon.
36
What does adolapin do? Inflam
Anti-inflammatory, inhibit cyclooxygenase
37
How does DOX lead to double-stranded breaks?
Stabilities transition state of Topoisomerase II.
38
What does helofensin do? Resp
inhibit direct electrical stimulation of isolated mouse hemi-draphragm
39
What does the coral snake venom cause?
bilateral ptsosis and respiratory failure
40
What does melittin do?
Haemorrhagic and increase cellular permeability (cell membrane lytic) by associating with bilayer and inhibiting PKC
41
Give the structure of Mitoxantrone.
42
Give the structure of AQ4N.
43
What is the structure of helothermine?
16 cysteine residues Cysteine rich secretory protein (CRISP)
44
What does cardiopep do?
Beta-adrenergic and anti-arrhythmic effect
45
What does Mast Cell Degranulating peptide do?
Inflammatory at low concentration Anti-inflammatory at high concentration
46
What does Gilatoxin do? (Coag.)
Degrade fibrinogen without producing clots
47
What is mass spec peaks are important?
Odd number = odd number of nitrogens
48
What is in the spreading factors paragraph?
Hyaluronidase (all) L-AAO (CS and GM) Horridum toxin (GM) Melittin (HB)
49
What does hyaluronidase do? (Spread)
Cleave hyaluronic acid, which is involved in repair, leading to inflammatory precursors and vasodilation.
50
If *Streptomycin* is grown on 2-[13C]acetate, which carbons are radiolabelled?
The carbon **_NOT_** linking the sugar, then every other one. Not including the 4th ring hydroxyl carbon.
51
What are the paragraph topics? (In order)
Introduction, coagulation, spreading factors, inflammation and allergy, ion channels, cell receptors, small signalling, vasodilators, respiratory system and conclusion.
52
Why are cardiomyocytes more susceptible to DOX damage?
Cardiomyocytes have a higher reliance on oxidative substrate mechanisms.
53
What are the topics of vasodilation paragraph?
Helokinestatins (GM) Exendin-1/2/3/4 (GM) Helodermatine (GM) Tachykinins (HB) Compound 48/80 (HB)
54
If *Streptomycin* is grown on 14O labelled acetate, which oxygebs are radiolabelled?
The bottom five
55
What does Serotonin do?
gut movement and happiness Pain and convulsions of muscle
56
What does melittlin do? Inflam
Anti-inflammatory
57
What do exendins do? Vaso
Act like vasoactive intestinal peptides and increase cellular cAMP lead to hypotensive effect
58
What is the strucure of 12-deoxyaklanonic acid?
59
What natural products are of use from GM?
Exendin-4 led to Exenatide (GLP mimic)
60
What are the 10 steps of doxorubicin synthesis?
1. Form first compound 2. Top ketone 3. Make 4th ring (alcohol) 4. +Alcohol (3rd ring) 5. Add sugar 6. Remove ester (-me, -CO2H) 7. Add keto (+OH, +=O) 8. Add ester (1st ring) 9. Add OH (far right)
61
Which proteins are involved in the coagulation paragraph? (Which species)
C-type lectin (CS) Gilatoxin (GM) Secapin (HB) PLA2 (All)
62
What do MmTX1/2 do? Recep
GABA receptors, increase susceptibility to agonist Reduced activity -\> seizures
63
What does Mm-8 do? recep
Affect post-synaptic nicotinic receptors function Reduced function -\> respiratory failure and death
64
What do L-AAOs do? (Spread)
Haemorrhagic and anti-coagulant.
65
Which IR peaks are important?
Double at 1600 is aromatic 1700 is C=O 3500 is OH
66
What does tertiapin and compoud 48/80 do? Inflam
Inflammatory and other roles.
67
What are the topics if inflammatoryparagraph?
Melittin Tachykinins (substance P, neurokin A+B) Tertiapin Compound 48/80 Mast cell degranulating peptide Adolapin
68
What does topoisomerase enzymes facilitate?
The unwinding and winding of supercoiled DNA, to allow DNA replication and transcription
69
Give the structure of epirubicin.
Inverted hydroxyl on glycone.
70
What is interesting about coral snake venom administration?
Cannot retract fangs, only small amount of venom, and bites/chews prey.
71
What are the topics of the respiratory system paragraph?
Helofensin (GM) Cardiopep (HB)
72
What do radicals do?
Proton abstraction of DNA Perioxidate lipids, lead to malondialdehyde-DNA Lead to AMP-activated protein kinase activation Leads to p53-induced cell death
73
What does tertiapin do? (Ion)
Blocks potassium ion channels: Calcium activated large conductance K - prolong AP + increase excitability Inward rectifier K - shorten AP Both on cardiac cells
74
Why does DOX have dose-limiting cardiotoxicity?
Irreversible accumulation of 8-hydroxyguanosine adducts in cardiac mRNA.
75
What does histmine do?
Inflammatory mediator
76
What does PLA2 do? (Coag.)
Thrombokinase inhibitor

Natural Sciences Bath Final Year (5 decks)

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