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Cognosy > Shikimic acid derivatives > Flashcards

Shikimic acid derivatives Flashcards

1
Q

Shikimic acid products are precursors for

A

Natural products
Aromatic amino acids eng phenylalanine, tyrosine, tryptophan

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2
Q

Which classes are under Shikimic acid? (Soccer’s FCL ParTy)

A
  1. Phenylpropenes
  2. Lignans
  3. Coumarins
  4. Flavanoids
  5. Tannins
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3
Q

How are Phenylpropenes bio synthesized into Cinnanic acid

A

Oxidation of phenylalanine by the enzyme phenylalanine ammonia lyase

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4
Q

Phenylpropenes come from which acid precursor

A

Cinnamic acid

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5
Q

Describe the phenylpropenes biopathway

A

Cinnamic acid is reduced to corresponding aldehyde, cinnamaldehyde
Cinnamaldehyde (component of cinnamon oil) is from Lauraceae
Used as spice and flavoring agent

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6
Q

What is Myristicin, from nutmeg, used for?

A

Hallucinogenic

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7
Q

Safrole and trans-anetgole from star anise
Fennel apiaceae are used as

A

Essential oils

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8
Q

How are ligands formed?

A

Coupling 2 phenylpropenes units

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9
Q

What is the precursor for lignans

A

Cinnamylalcohol

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10
Q

North Indian Americans treat warts using

A

Podophyllotoxic (toxic)
40-demethylpodophyllotoxin
alpha and beta petatin (from Podiphyllum pet Tatum and Podiphyllum hexandrum, Berberidaceae)

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11
Q

Coumarins are formed when

A

Phenylalanine is deaminated and hydroxylated to trans-hydroxycinnamic acid
It then readily converts to Cis form which readily undergoes lactonization run to form coumarin itself

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12
Q

What are the 2 types of coumarins

A

Phytoalexins
Psoralens

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13
Q

How are phytoalexins made, give an example

A

Made de Novo following bac/fungal infection
Aesculetun occurs in horse chestnut, phytotherapeutic preps of bark, treat capillary fragility

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14
Q

Describe Psoralens, give example

A

Have Furan ring
They’re from citrus (Rutaceae) and celery (Apiaceae) families
Produced by plant as protection from the sun, now used as sunscreen
Increase skin pigment so it treats vitiligo too
Shape is a Caterpillar with hexagon tail and O infused at every down corner, skipping space for R2

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15
Q

Flavanoids are products of mixed Biosynthesis from…

A

Shikimic acid and polyketide pathways

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16
Q

What are the 2 main uses of flavanoids

A

Color, attract insects for pollination
Strong antioxidants e. g Quercetin
Reduce poisoning of Amanita fungi

17
Q

Which classs comprises of water soluble polyphenolic compounds?

A

Tannins

18
Q

What are the two types of tannins?

A

Hydrosolube
Non-hydrosolube

19
Q

How are hydrosolube tannins made

A

Esterification of sugar and simple phenolic acid e. g Gallic acid

20
Q

How are non hydrosolube tannins made?

A

Condensed tannins= polymerization between flavanoids

21
Q

Tannins are used to clarify beer, as astringents in meds and tan leather, due to their

A

Protein binding ability
Tannic acid is also used as a topical for cold sores.

Cognosy (8 decks)

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