Pharmacognosy: Shikimic Acid and Coumarins
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Questions and Answers

What is the primary focus of the Shikimic acid pathway?

  • Formation of aromatic amino acids (correct)
  • Production of flavonoids
  • Synthesis of alkaloids
  • Metabolism of lipids
  • Which compounds are derived from the Shikimic acid pathway?

  • Saponins and glycosides
  • Terpenes and steroids
  • Phenolic acids and tannins
  • Coumarins and furanocoumarins (correct)
  • What is a key characteristic of furanocoumarins?

  • They are known for their antibiotic properties.
  • They often exhibit bioactive properties. (correct)
  • They are primarily aromatic hydrocarbons.
  • They are exclusively found in synthetic compounds.
  • Chromones are classified as which type of compound?

    <p>Condensed phenolic compounds (A)</p> Signup and view all the answers

    Which of the following pathways is indirectly related to the production of secondary metabolites in plants?

    <p>Shikimic acid pathway (B)</p> Signup and view all the answers

    What is the primary function of shikimic acid in relation to oseltamivir synthesis?

    <p>It is the starting material for synthesizing oseltamivir. (D)</p> Signup and view all the answers

    What type of inhibitor is oseltamivir phosphate (Tamiflu)?

    <p>Neuraminidase inhibitor (C)</p> Signup and view all the answers

    Which plant is known as the source of shikimic acid used in Tamiflu production?

    <p>Star anise (A)</p> Signup and view all the answers

    What is one of the roles of shikimic acid in plants?

    <p>Protection against microorganisms (A)</p> Signup and view all the answers

    For what specific diseases is oseltamivir phosphate intended for treatment?

    <p>Influenza viruses A and B (A)</p> Signup and view all the answers

    What is shikimic acid derived from?

    <p>Fermentation of genetically engineered E. coli (C)</p> Signup and view all the answers

    Which gene is deficient in the genetically engineered E. coli used for shikimic acid production?

    <p>Shikimate kinase gene (B)</p> Signup and view all the answers

    What role does shikimate kinase play in E. coli?

    <p>It is involved in the biosynthesis of amino acids (A)</p> Signup and view all the answers

    Why are genetically engineered E. coli strains used in shikimic acid production?

    <p>To increase the yield of shikimic acid (D)</p> Signup and view all the answers

    What is a potential application of shikimic acid obtained from E. coli?

    <p>Synthesis of antiviral medications (B)</p> Signup and view all the answers

    What type of toxins are aflatoxins classified as?

    <p>Hepatotoxins and carcinogens (A)</p> Signup and view all the answers

    From which fungus are aflatoxins produced?

    <p>Aspergillus (B)</p> Signup and view all the answers

    Which structural component is common to all aflatoxins?

    <p>Coumarin ring (A)</p> Signup and view all the answers

    What type of health issues can aflatoxins cause?

    <p>Liver damage and cancer (C)</p> Signup and view all the answers

    In which of the following conditions would you expect aflatoxins to be a concern?

    <p>High humidity and temperature in food storage (A)</p> Signup and view all the answers

    Which furanocoumarin is NOT mentioned as being found in grapefruits?

    <p>Psoralen (C), Limonin (D)</p> Signup and view all the answers

    What is the primary effect of grapefruit juice on drug metabolism?

    <p>It inhibits CYP3A4-mediated drug metabolism. (C)</p> Signup and view all the answers

    What role do furanocoumarins play in the interaction between grapefruit and drug metabolism?

    <p>They interfere with liver and intestinal enzyme CYP3A4. (C)</p> Signup and view all the answers

    Which of the following statements about CYP3A4 is accurate?

    <p>CYP3A4 is an enzyme involved in drug metabolism. (D)</p> Signup and view all the answers

    Which statement correctly describes the relation between grapefruit juice and drug interactions?

    <p>Grapefruit juice can increase the effects of certain medications. (A)</p> Signup and view all the answers

    What methods does Roche currently use to obtain shikimic acid?

    <p>Both extraction and fermentation methods (B)</p> Signup and view all the answers

    What is the primary characteristic of free coumarins?

    <p>Organic solvents-soluble (C)</p> Signup and view all the answers

    Which of the following is a coumarin glucoside found in horse chestnut?

    <p>Aesculin (C)</p> Signup and view all the answers

    What chemical is used in the conversion process from shikimic acid?

    <p>Chorismic acid (C)</p> Signup and view all the answers

    What is the effect of coumarins in medicinal applications?

    <p>Anti-inflammatory effects (D)</p> Signup and view all the answers

    Which plant is a significant source of aescin?

    <p>Aesculus hippocastanum (B)</p> Signup and view all the answers

    What possible health risk is associated with high consumption of Cassia cinnamon?

    <p>Liver toxicity (D)</p> Signup and view all the answers

    Which of the following is NOT a common family where coumarins are found?

    <p>Solanaceae (C)</p> Signup and view all the answers

    What is the main structural characteristic that differentiates derivatives of coumarins?

    <p>Substituents on the benzene ring (A)</p> Signup and view all the answers

    Which of the following compounds is involved in the synthesis of alkaloids from tyrosine?

    <p>Anthranilic acid (B)</p> Signup and view all the answers

    Flashcards

    Shikimic acid pathway

    A metabolic pathway for the biosynthesis of various aromatic compounds, including coumarins, furanocoumarins, and chromones.

    Coumarins

    A class of aromatic plant compounds with specific chemical structures.

    Furanocoumarins

    A type of coumarin with a furan ring.

    Chromones

    Another group of plant-derived aromatic compounds related to coumarins.

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    Pharmacognosy and Phytochemistry

    The study of medicinal plants and their chemical constituents.

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    Shikimic acid

    A biochemical intermediate used to make the antiviral drug Tamiflu.

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    Tamiflu

    An antiviral drug that inhibits neuraminidase, fighting flu.

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    Oseltamivir

    A compound produced from shikimic acid for flu treatment.

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    Neuraminidase inhibitor

    A drug that blocks an enzyme important for flu virus spread.

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    Shikimic acid's role

    Shikimic acid is a essential precursor for the production of Tamiflu

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    Escherichia coli

    A common bacterium found in the intestines of humans and animals, often used in genetic engineering.

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    Genetically engineered E. coli

    Modified strains of E. coli bacteria that were engineered to produce specific compounds, like shikimic acid.

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    Shikimate kinase gene

    A gene responsible for producing an enzyme that plays a crucial role in the metabolic pathway for shikimic acid production.

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    Deficient in shikimate kinase gene

    Describes E. coli strains that lack the ability to produce the enzyme shikimate kinase, thereby inhibiting their normal production of shikimic acid.

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    Aflatoxins

    A group of toxic compounds produced by the Aspergillus fungus. They can cause liver cancer and damage.

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    Mycotoxin

    A toxin produced by a fungus.

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    Hepatotoxin

    A substance that damages the liver.

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    Unsaturated lactone

    A part of the aflatoxin structure that contains a ring with double bonds.

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    What is the origin of the name 'coumarin'?

    It comes from the local Guyana name 'Coumarouna' for the seeds of Dipteryx odorata, also known as Tonka bean.

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    Umbelliferone

    A common coumarin with a hydroxyl group (OH) at position 7 of the benzene ring.

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    Aesculin

    A coumarin glucoside found in Aesculus hippocastanum (horse chestnut), known for its anti-inflammatory properties.

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    What type of effects does Aescin have?

    Aescin, a mixture of saponins found in horse chestnut, has anti-inflammatory, vasoconstrictor, and vasoprotective effects.

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    Cinnamic acid

    An aromatic acid produced via the shikimic acid pathway, crucial for the biosynthesis of many secondary metabolites in plants.

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    What is the main source of coumarin in foods?

    Cassia cinnamon contains high amounts of coumarin, which can cause liver toxicity and damage in large quantities.

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    Grapefruit Juice Effect

    Grapefruit juice inhibits the CYP3A4 enzyme, which is crucial for drug metabolism in the liver and intestines.

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    CYP3A4

    A key enzyme in the liver and intestines that breaks down many medications.

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    Bergamottin

    A specific type of furanocoumarin found in grapefruit, known to inhibit CYP3A4.

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    6',7'-Dihydroxybergamottin

    Another potent furanocoumarin in grapefruit that also disrupts CYP3A4 activity.

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    Study Notes

    Pharmacognosy and Phytochemistry (Coumarins/furanocoumarins/chromones)

    • Shikimic acid is isolated from plants of Illicium species (Japanese "shikimi," Japanese star anise)
    • The shikimic acid pathway is important for aromatic compounds
    • It's a precursor of aromatic amino acids (Phe, Tyr, Try) biosynthesis in bacteria, fungi, and higher plants
    • It's a building block for other compounds: alkaloids, coumarins, phenyl propanes, and volatile oils
    • It's a starting point for tannins in all plants
    • It provides protection of plants against microorganisms
    • Oseltamivir phosphate (Tamiflu) is an orally active neuraminidase inhibitor, developed for treating and preventing influenza viruses A and B
    • The starting material for the synthesis of oseltamivir is (-)-shikimic acid
    • Shikimic acid is currently in demand as the raw material for the synthesis of oseltamivir (Tamiflu), for defense against avian influenza (bird flu)
    • Illicium verum (star anise) contains large amounts of shikimic acid
    • The drug manufacturer Roche currently relies on both extraction and fermentation to obtain shikimic acid

    Coumarins

    • Coumarin is a derivative of Benzo-α-pyrone
    • It has a vanilla-like flavor
    • It's an oxygen heterocycle
    • Coumarin can be free or combined with glucose (coumarin glycoside)
    • Coumarins are organic solvents-soluble
    • Derivatives differ in benzene ring substitutions (OH, OCH₃, CH₃)
    • Coumarins are common in Apiaceae, Fabaceae, and Rutaceae families
    • Umbelliferone: R₁ = H, R₂ = OH
    • Aesculetin: R₁ = R₂ = OH
    • Scopoletin: R₁ = OCH₂, R₂ = OH
    • Coumarins are hepatotoxic in high doses
    • Coumarin and several derivatives have various therapeutic and pharmacological potentials.

    Furanocoumarins (Photosensitizers)

    • Often known as psoralens
    • Plants containing psoralens are used internally and externally to promote skin pigmentation and suntanning
    • Psoralen absorbs near UV light and stimulates melanin pigment formation
    • Furan ring is derived from isopentyl pyrophosphate (mevalonic acid pathway)

    Aflatoxins

    • Aflatoxins are mycotoxins produced by the fungus Aspergilus
    • Aflatoxins are potent hepatotoxins and carcinogens in the liver
    • All aflatoxins contain a coumarin ring and an unsaturated lactone moiety

    Bleeding

    • Dicoumarol is present in sweet clover ( Melilotus officinalis)
    • Dicoumarol interferes with the effects of vitamin K in blood coagulation.
    • The blood loses its ability to clot, and minor injuries can lead to severe internal bleeding

    Medical Value of Coumarins / Furanocoumarins

    • Aesculin/Aescin from Aesculus hippocastanum reduces inflammation, and is used as an anti-inflammatory agent, and also for treating cutaneous capillary fragility
    • Psoralens and derivatives used in PUVA photochemotherapy for vitiligo and psoriasis repigmentation.
    • Methoxsalen (also known as xanthotoxin), commonly found in the fruits of Ammi majus is used for skin repigmentation.

    Grapefruits

    • Grapefruit juice inhibits CYP3A4-mediated drug metabolism
    • Major furanocoumarins in grapefruits include bergamottin and 6',7'-dihydroxybergamottin

    Other Details

    • Warfarin, a coumarin derivative, is used as an anticoagulant
    • Warfarin's discovery was linked to an outbreak of hemorrhaging in cattle consuming moldy sweet clover
    • The 14th Dalai Lama's quote on happiness

    Ammi visnaga

    • Ammi visnaga contains furochromones, used traditionally as an antispasmodic and for angina pectoris treatment
    • Khellin, extracted from Ammi visnaga, is a coronary vasodilator and spasmolytic agent
    • Khellin and its analogs (e.g., amiodarone, cromolyn sodium) are also used in current medical practice

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    Description

    Explore the fascinating world of pharmacognosy and phytochemistry focusing on shikimic acid, its role in the biosynthesis of aromatic compounds, and its application in synthesizing oseltamivir for influenza treatment. This quiz covers important plant-derived compounds and their significance in both nature and medicine.

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