Metabolites and Pathways Quiz
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Questions and Answers

What condition can develop from long-term use of anthraquinones associated with a change in the colon lining?

  • Cirrhosis
  • Crons Disease
  • Melanesia coli (correct)
  • Irritable bowel syndrome

    • Which of the following is a noted side effect of chronic anthraquinone use?

  • Diarrhea
  • Hypokalemia (correct)
  • Iron deficiency
  • Gastroesophageal reflux

    • For how long is it considered unsafe to use laxatives containing anthraquinones?

  • More than two weeks
  • More than one week (correct)
  • More than three weeks
  • More than one month

    • Which of the following could result from laxative dependence?

    <p>Reduction of bowel function (D)</p> Signup and view all the answers

    What are albuminuria and hematuria indicative of in the context of laxative use?

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

    What are the main components of Sennoside A and B?

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

    Which compound has the aglycone as Rhein?

    <p>Both Sennoside A and B (C)</p> Signup and view all the answers

    What type of glycosides are derived from anthrones in the leaves?

    <p>Dimeric anthracene glycosides (A)</p> Signup and view all the answers

    Which moieties are involved in the structure of dimeric anthracene glycosides?

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

    Which of the following is primarily found in the structure of Aloe-emodin anthrone?

    <p>Hydroxyl groups (A)</p> Signup and view all the answers

    What distinguishes aloin A from aloin B?

    <p>The orientation of the substituents on C-10 (C)</p> Signup and view all the answers

    Which of the following is NOT a warning associated with the ingestion of Aloe preparations?

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

    Which adverse effect is common with the use of Aloe preparations?

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

    What severe reaction can occur as a result of Aloe preparations?

    <p>Kidney failure (A)</p> Signup and view all the answers

    Which condition might result from Aloe ingestion due to loss of potassium?

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

    What is the primary form of application for the treatment of chronic eczema and psoriasis?

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

    In addition to treating chronic eczema and psoriasis, what other use is mentioned for this substance?

    <p>As a purgative (A)</p> Signup and view all the answers

    Which condition is NOT treated by the ointment mentioned?

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

    What is the main therapeutic function of the ointment in the context provided?

    <p>To cure skin conditions (B)</p> Signup and view all the answers

    Which of the following is a characteristic feature of the conditions treated by the ointment?

    <p>They are chronic skin disorders (C)</p> Signup and view all the answers

    What is malic acid primarily known for in plants?

    <p>Contributing to the sour taste of fruits and vegetables (D)</p> Signup and view all the answers

    From which insect is carminic acid derived?

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

    Which of the following correctly identifies carminic acid?

    <p>A C-glycoside of an anthraquinone derivative (D)</p> Signup and view all the answers

    What is one of the specific code names for the pigment derived from carminic acid?

    <p>C.I. 75470 (A)</p> Signup and view all the answers

    What percentage of the cochineal crude drug consists of carminic acid?

    <p>10% (C)</p> Signup and view all the answers

    What type of compound is hypericin?

    <p>An anthraquinone derivative (B)</p> Signup and view all the answers

    In which parts of the Hypericum perforatum plant is hypericin predominantly found?

    <p>Leaves and flowers (D)</p> Signup and view all the answers

    What is the primary color of hypericin?

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

    What structural form does hypericin exist as?

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

    Which of the following statements about hypericin is correct?

    <p>It is derived from a class of compounds known as anthraquinones. (D)</p> Signup and view all the answers

    Flashcards

    Long-term anthraquinone use

    Prolonged use of anthraquinone-based laxatives might cause significant side effects.

    Melanosis coli

    A condition where colon lining darkens, potentially increasing cancer risk.

    Anthraquinone laxative safety

    Avoid using anthraquinone laxatives for over a week.

    Laxative dependence

    Regular laxative use can lead to reliance on laxatives to have bowel movements.

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    Hypokalemia

    Low potassium levels in the body, a possible side effect of certain laxatives.

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    Anthracene glycosides

    Compounds derived from anthrones, linked together.

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    Aloe-emodin

    One type of anthrone moiety in anthracene glycosides.

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    Rhein

    Another anthrone moiety in anthracene glycosides.

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    Sennoside A&B

    Main components of a compound, dianthrones with rhein aglycones.

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    Stereoisomers

    Identical molecules but with different spatial arrangement.

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    Aloe A vs. Aloe B

    Aloe A and Aloe B are similar molecules, differing only in the arrangement of parts on the C-10 carbon atom.

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    Aloe Preparations: Side Effects

    Using Aloe products internally can cause various problems like diarrhea, low potassium levels, colon discoloration, kidney issues, sun sensitivity, and allergic reactions.

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    Diarrhea from Aloe

    Ingestion of Aloe can lead to loose stools and frequent bowel movements.

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    Pseudomelanosis Coli

    A condition where the lining of the colon darkens due to Aloe use.

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    Aloe and Kidney Issues

    Aloe intake is associated with potential problems related to kidney function.

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    Anthraquinone use

    Using medications containing anthraquinones, often in the form of ointments, for conditions like eczema and psoriasis.

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    Chronic eczema

    A long-lasting skin condition causing dryness, itching, and inflammation.

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    Psoriasis

    A chronic skin condition causing red, scaly patches.

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    Purgative effect

    A strong laxative effect causing frequent bowel movements.

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    Anthraquinone ointment

    A topical medication containing anthraquinones, used for skin conditions.

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    Malic acid

    A naturally occurring acid found in many fruits and vegetables, responsible for their sour taste.

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    Carmine

    A vibrant red pigment extracted from the cochineal insect. It's used as a natural food coloring.

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    Cochineal

    The dried female cochineal insect, a source of carmine pigment.

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    Carminic acid

    The main component of carmine pigment, a water-soluble anthraquinone derivative.

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    Anthraquinone derivative

    A type of chemical compound with a specific structure, responsible for the color of carmine.

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    Hypericin

    A reddish substance found in St. John's Wort, belonging to a group called anthraquinones.

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    Anthraquinone

    A large group of chemical compounds, including Hypericin, often found in plants.

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    Dimeric

    Means that the molecule is made up of two identical parts.

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    Hypericum perforatum

    The scientific name for the plant commonly known as St. John's Wort.

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    What is Hypericin?

    Hypericin is a red-colored, dimeric anthraquinone derivative found in the leaves and flowers of Hypericum perforatum (St. John's Wort).

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    Study Notes

    Primary Metabolites

    • Primary metabolites are essential compounds produced by living organisms for growth and life.
    • They are derived from sugars via primary metabolic pathways.
    • Examples include sugars, lipids, amino acids, peptides, and proteins.

    Secondary Metabolites

    • Secondary metabolites are low molecular weight compounds.
    • They are not essential for growth but are produced for adaptation and specific functions.
    • They are considered a phenotype of the organism.
    • They are derived from primary metabolites via secondary metabolic pathways.
    • They are more important than primary metabolites as therapeutic agents.

    Acetate-Malonate Pathway

    • The pathway synthesizes fatty acids and aromatic metabolites.
    • Key precursors are Acetyl-CoA and Malonyl-CoA.
    • End products can be saturated or unsaturated fatty acids or polyketides.
    • Polyketides are natural products synthesized by bacteria, fungi, and plants.

    Anthraquinone Glycosides

    • Most anthraquinone glycosides and aglycones are derived from the acetate pathway.
    • They start from acetic acid units forming acetyl-CoA and then malonyl-CoA.
    • The octa-β keto methylene chain loses CO2 and undergoes cyclization to form anthraquinones.
    • Anthraquinones are important chemical groups with a large, aromatic structure.
    • They are found in fungi, lichens, and plants.
    • They are sparingly soluble in cold water but soluble in organic solvents and alcohols.
    • Anthranol and antrone oxidation during plant storage increases laxative effects.

    Glycosides

    • Glycosides are compounds where an aglycone (non-sugar component) is linked to a sugar unit.

    Anthraquinone Glycosides Types

    • 1-O-glycosides: Glycone moiety is 1,8 dihydroxyanthraquinone.
      • Examples include Aloe-emodin-8-glycoside, Rhein-8-glycoside, and Chrysophanol-8-glycoside.
    • 2-O-glycosides: Aglycone moiety is partially reduced 1, 8 dihydroxyanthraquinone.
      • Example includes Emodin-oxanthrone-9-glucoside
    • 3-C-glycosides: Aglycone structure is an anthrone derivative.
      • Example includes Aloin
    • 4-C- and O-glycosides: Include Cascarosides A&B (barbaloin/aloin) and Cascarosides C&D (chrysaloin).

    Pharmacologic Actions of Anthraquinones

    • They are stimulant cathartics that increase colon smooth muscle tone and water/electrolyte secretion.
    • Hydrolysis in the colon results in active aglycones that act within 8-12 hours.
    • They are used to treat constipation and to prepare for procedures requiring bowel evacuation.

    Adverse Effects of Anthraquinones

    • Long-term use or high doses can cause severe adverse effects, like laxative dependence, hypokalemia, albuminuria, hematuria, heart arrhythmia, nephropathy, edemas, and accelerated bone deterioration.
    • Colon lining can take on a dark brownish-black hue (melanosis coli), increasing cancer risk.
    • Should not be used in cases of dehydration, diarrhea, or loose stools.

    Uses

    • Important laxative agents
    • Used in the treatment of constipation.
    • Used for bowel evacuation prior to medical procedures.

    Plant Sources

    • Senna ( Cassia acutifolia and Cassia angustifolia)
    • Aloe (Aloe barbadensis)
    • Cascara sagrada (Frangula purshiana)
    • Rhubarb (Rheum palmatum)

    Additional Notes

    • There are various chemical compounds within these plant families that are relevant and useful in treatment

    Chemistry of Compounds

    • Chemical structures for specific anthraquinones, glycosides, and their related compounds are described.

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    Description

    Test your knowledge on primary and secondary metabolites, their significance, and the acetate-malonate pathway. This quiz covers essential compounds, their functions, and the synthesis of fatty acids and natural products. Dive into the world of biochemistry and explore the roles of these metabolites in living organisms.

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