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Mpharm 1 > PH1125 - Natural Products > Flashcards

PH1125 - Natural Products Flashcards

1
Q

what are natural products?

A
  • organic molecules biosynthesized by living organisms
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2
Q

what are secondary metabolites?

A
  • molecules not directly essential to the function/survival of the organism they are isolated from
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3
Q

what do natural products provide in terms of drug development?

A
  • the lead compound
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4
Q

what is phytochemistry?

A
  • the study of single molecules extracted from a plant
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5
Q

what are alkaloids?

A
  • large class of nitrogen-containing natural products very well known for their medicinal properties
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6
Q

what are the chemical properties of alkaloids? (3)

A
  • always contain nitrogen
  • often basic (although varies and can be neutral at physiological pH)
  • often white crystalline solids when pure
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7
Q

what are examples of alkaloids? (4)

A
  • nicotine
  • quinine
  • atropine
  • caffeine
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8
Q

how do tropane alkaloids work? (2)

A
  • they are competitive with acetylcholine for binding to muscarinic receptors in smooth muscle
  • this blocks the nerve impulse and hence causes the muscle to relax
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9
Q

what is morphine? (2)

A
  • well known alkaloid natural product

- classifies as isoquinoline alkaloid but has undergone further biosynthetic chemistry

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10
Q

what contains many medicinally important alkaloids?

A
  • opium; a latex produced by the opium poppy
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11
Q

what is the problem with morphine as a treatment of pain/analgesic?

A
  • in is very addictive and causes euphoria
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12
Q

what are polyketides?

A
  • large class of natural products formed by condensation of acetate monomers
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13
Q

what is a biological form of acetate?

A
  • acetyl CoA
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14
Q

what effect does senna have on body?

A

purgative effect by increasing gut motility

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15
Q

what are sennosides metabolised to?

A
  • rhein and aglycone believed to be the active species
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16
Q

what is doxorubicin?

A
  • polyketide derivative isolated from the bacterium Streptomyces peucetius
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17
Q

what is doxorubicin used for?

A
  • broad spectrum anti-cancer drug
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18
Q

what reaction do polyketides readily undergo?

A
  • aldol reactions
    The aldol reaction is used to join two identical aldehydes or ketones together (dimer), or two different aldehydes or ketones (crossed-aldol).
19
Q

what is erythromycin used for?

A
  • antibiotic often used in penicillin-resistant patients
20
Q

what is tetracycline? (2)

A
  • widely used antibiotic

- originally isolated as a trace molecule from Streptomyces aureofaciens

21
Q

what is amphotericin B and why is it IV treatment? (2)

A
  • anti-fungal drug

- used for life threatening diseases which are harder to kill due to fungi being eukaryotic and same cell types as us

22
Q

what are the difference from natural products and herbal medicine? (2)

A
  • natural products are single molecules

- herbal medicines are a mixture of many compounds

23
Q

what is the drug substance of herbal medicines?

A

dried, unprocessed plant material

24
Q

what is st johns wort used for?

A
  • herbal medication used for mild to moderate depression
25
Q

what is a significant problem for st johns wort medication?

A
  • drug interactions with prescribed drugs
26
Q

what is paclitaxel? (3)

A
  • terpenoid produced by the yew tree
  • it is used to treat ovarian, breast and other solid cancers
  • it is too complex to synthesize and is currently produced by biotechnology
27
Q

what are terpenoids?

A
  • built from isoprene building blocks
28
Q

what is an excellent biological leaving group?

A
  • pyrophosphate
29
Q

how are terpenoids classified?

A
  • they are classified by the number of carbon atoms in their structure
30
Q

what is monoterpene geraniol?

A
  • fragrant volatile oil produced by many plants and used commercially in perfumery
31
Q

what is menthol? (2)

A
  • isolated from peppermint

- its volatile properties are widely used in medicine for cold relief

32
Q

what is fusidic acid? (2)

A
  • steroidal antibiotic produced be a fungus

- narrow spectrum but can be applied topically

33
Q

what is paclitaxel? (3)

A
  • terpenoid produced by the yew tree
  • it is used to treat ovarian, breast and other solid cancers
  • it is too complex to synthesize and is currently produced by biotechnology
34
Q

what are terpenoids?

A

naturally occurring organic chemicals

- built from isoprene building blocks

35
Q

what are the intermediates used in terpenoid biosynthesis? (2)

A
  • isopentene-OPP

- dimethylallyl-OPP

36
Q

how are terpenoids classified?

A
  • they are classified by the number of carbon atoms in their structure
37
Q

what is monoterpene geraniol?

A
  • fragrant volatile oil produced by many plants and used commercially in perfumery
38
Q

what is menthol? (2)

A
  • isolated from peppermint

- its volatile properties are widely used in medicine for cold relief

39
Q

what is a precursor for steroids?

A
  • squalene
40
Q

what is fusidic acid? (2)

A
  • steroidal antibiotic produced be a fungus

- narrow spectrum but can be applied topically

41
Q

why do carbohydrates have excellent water solubility?

A
  • they contain many hydroxyl groups that can readily form hydrogen bonds with water
42
Q

what is a glycoside?

A
  • generally used to describe any natural product that contains an additional carbohydrate group
43
Q

what are O-glycosides?

A
  • natural products containing a sugar bonded via an oxygen atom
44
Q

what is digoxin solubilized by?

A
  • the very non-polar (hydrophobic) steroid portion of the drug is solubilized by the polar hydrophilic O-glycoside

Mpharm 1 (59 decks)

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