Biochemistry of Natural Products Lecture 3: Flavonoids

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Questions and Answers

What is one of the mechanisms by which quercetin aids in the prevention of peptic ulcers?

  • Increasing H.pylori growth
  • Promoting mucus secretion (correct)
  • Inhibiting mucus production
  • Stimulating gastric acid secretion

How does oxidative LDL (oxLDL) contribute to atherosclerosis?

  • It directly increases HDL levels in the bloodstream
  • It enhances the immune response and inflammation (correct)
  • It decreases blood flow to the arteries
  • It promotes cholesterol absorption in the intestines

Which statement best describes the effect of flavonoids on LDL oxidation?

  • Flavonoids only affect HDL metabolism
  • Flavonoids enhance the oxidation of LDL particles
  • Flavonoids have no effect on LDL oxidation
  • Flavonoids suppress LDL oxidation and inflammation (correct)

What role does the D-alanine- D-alanine ligase (Ddl) enzyme play concerning H.pylori?

<p>It is crucial for bacterial cell wall assembly (A)</p> Signup and view all the answers

What is a primary risk factor for the development of atherosclerosis?

<p>Elevated plasma LDL concentration (A)</p> Signup and view all the answers

What effect do flavonoids like quercetin have on the inflammatory response?

<p>They inhibit the COX pathway and inflammatory mediators. (B)</p> Signup and view all the answers

Which of the following is a result of oxidized LDL accumulation in the arteries?

<p>Formation of plaque due to macrophage and lipid accumulation. (B)</p> Signup and view all the answers

Which of the following factors does NOT increase levels of oxidized LDL?

<p>Regular physical exercise. (D)</p> Signup and view all the answers

What is one potential consequence of oxidized LDL accumulation in the arteries?

<p>Coronary heart disease and dementia. (A)</p> Signup and view all the answers

Which flavonoid is specifically mentioned as having hepatoprotective activity?

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

Flashcards

Oxidized LDL

LDL cholesterol that has reacted with free radicals, increasing its reactivity and causing tissue damage.

Heart Disease Risk

Consuming red wine in moderation helps protect against heart disease and cardiovascular disease.

Vascular Plaque Formation

Oxidized LDL accumulates in artery walls, attracting inflammatory cells and lipids, forming a plaque that thickens over time.

Inflammation & COX

Inflammation is initiated by the release of arachidonic acid and Cyclooxygenase (COX) is a key inflammatory mediator.

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Flavonoids-Liver Protection

Specific flavonoids, like silymarin, apigenin, quercetin, and naringenin, help protect the liver.

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Helicobacter pylori (H. pylori)

A human bacterium linked to gastritis, peptic ulcers, and gastric cancer.

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Quercetin's role in peptic ulcers

Quercetin promotes mucus secretion, protecting the stomach lining and inhibits H.pylori bacteria growth, aiding in peptic ulcer prevention and treatment.

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Atherosclerosis

A condition where fatty substances build up in artery walls, reducing blood flow and potentially leading to heart attacks or strokes.

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LDL oxidation

LDL reacting with free radicals, becoming more harmful, and contributing to atherosclerosis development.

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Flavonoids' effect on atherosclerosis

Flavonoids suppress LDL oxidation and inflammation in artery walls, lowering risk of this blood vessel issue.

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Study Notes

Biochemistry of Natural Products, Lecture 3: Flavonoids

  • Flavonoids are polyphenolic secondary plant metabolites.
  • They comprise 15 carbons (2 aromatic rings connected with a 3-carbon bridge) and numerous hydroxyl groups (OH).
  • Flavonoids exhibit antioxidant properties by acting as free radical scavengers, singlet oxygen quenchers, hydrogen donors, and metal chelators.
  • Flavonoid sources include fruits and vegetables, tea, red wine, citrus fruits, cocoa, and berries. Specific flavonoid types within these sources include: flavanols, flavonols, flavanones, isoflavones, and anthocyanins (depending on the food type).
  • Flavonoids have several important biological properties.
    • Anti-ulcer effects: promote mucus secretion and inhibit H. pylori bacteria.
    • Anti-atherosclerotic effects: suppress LDL oxidation and inflammatory progression in arteries. Elevated LDL is a primary risk factor for atherosclerosis and coronary artery disease. Oxidized LDL reacts with free radicals, becoming more reactive and causing tissue damage; it also attracts immune cells (e.g. macrophages) and platelets to the damaged area exacerbating the process.
    • Anti-inflammatory effects: inhibit the cyclooxygenase (COX) pathway and inflammatory mediators like arachidonic acid.
    • Hepatoprotective activity: many flavonoids (e.g., silymarin, apigenin, quercetin, naringenin) protect the liver.
    • Memory improvements: through various mechanisms like anti-neuroinflammatory actions, reducing metal ion neurotoxicity, promoting autophagy, reducing oxidative stress, mitigating mitochondrial dysfunction, and reducing amyloid-β and tau levels.

Physicochemical Properties, Extraction, Characterization, and Quantification

  • Flavonoid glycosides are water-soluble and soluble in alcohols.
  • Glycosides are extracted primarily using acetone or alcohols (ethanol, methanol) mixed with water, often at high temperatures.
  • Aglycones are soluble in apolar organic solvents (like dichloromethane).

Extraction and Characterization of Flavonoids

  • Extraction methods include maceration, Soxhlet, ultrasound-assisted extraction (UAE), supercritical fluid extraction (SFE), and accelerated solvent extraction (ASE).
  • Chromatographic techniques (HPLC, TLC) are used for analysis.

Detection and Quantification of Flavonoids

  • Flavonoids can be identified and quantified using various chemical tests.
    • Shinoda, Vanillin-HCl, Zinc, and Ammonia tests produce specific color changes in the presence of flavonoids.

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