Terrestrial Natural Product Chemistry
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Questions and Answers

Which of the following is considered a major class of phytoestrogens?

  • Flavonoids
  • Lignans (correct)
  • Stilbenes
  • Terpenes

What is the primary lignan precursor found in flaxseed?

  • Secoisolariciresinol diglucoside (correct)
  • Pinoresinol
  • Enterodiol
  • Matairesinol

Which compound is NOT a type of plant lignan?

  • Pinosylvin (correct)
  • Secoisolariciresinol
  • Enterolactone
  • Lariciresinol

How much do Lariciresinol and Pinoresinol contribute to total dietary lignan intake?

<p>75% (C)</p> Signup and view all the answers

Which substance is formed from plant lignans by intestinal bacteria?

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

What is formed by the reduction of the carboxylic acid functional groups in cinnamic acids?

<p>Monolignols (A), Cinnamic aldehydes (B), Cinnamaldehyde (D)</p> Signup and view all the answers

Which acid is a precursor to p-coumaric acid?

<p>Cinnamic acid (D)</p> Signup and view all the answers

Which substance is derived from monolignols and is a primary constituent of essential oils?

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

What is the structural role of lignin and suberin in plants?

<p>They form structural components of plant cell walls (D)</p> Signup and view all the answers

What is chalcone a precursor for?

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

Which of the following is a hydroxylated derivative of p-coumaric acid?

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

Which of these compounds absorbs ultraviolet light strongly and is used in sunscreens?

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

Which compound is NOT derived from monolignols?

<p>P-coumaric acid (C)</p> Signup and view all the answers

What primary metabolites are converted in the Shikimate pathway to produce chorismate?

<p>Phosphoenolpyruvate and erythrose-4-phosphate (B)</p> Signup and view all the answers

Which of the following amino acids are synthesized through the Shikimate pathway?

<p>Phenylalanine, tyrosine, tryptophan (A)</p> Signup and view all the answers

What is one key role of chorismate in plant metabolism?

<p>It is essential for the biosynthesis of certain aromatic amino acids. (B)</p> Signup and view all the answers

Which compound is NOT a product of the phenylpropanoid pathway derived from phenylalanine?

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

In the context of biochemistry, which of the following pathways is primarily associated with terpenoids and steroids?

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

The Shikimate pathway is often referred to as the common aromatic biosynthetic pathway due to its role in producing which type of compounds?

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

What role does phenylalanine play in protein synthesis?

<p>It is an essential amino acid utilized in protein synthesis. (C)</p> Signup and view all the answers

Which of the following aromatic compounds is synthesized directly through the pathway involving chorismate?

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

What role does indoleacetic acid, derived from tryptophan, play in plants?

<p>Cell expansion and maintenance of apical dominance (A)</p> Signup and view all the answers

Which amino acids are involved in the biosynthesis of phenylpropanoids?

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

What is the function of phenylpropanoids in plants?

<p>Defense, structural integrity, and signaling (A)</p> Signup and view all the answers

Which enzyme converts phenylalanine to cinnamic acid?

<p>Phenylalanine ammonia-lyase (PAL) (A)</p> Signup and view all the answers

What process synthesizes aromatic amino acids in plants?

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

What is the primary function of phytoalexins in plants?

<p>To protect against microbial infections (B)</p> Signup and view all the answers

Which compound is a common example of a volatile component derived from phenylpropanoids?

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

Which of the following statements about the shikimate pathway is true?

<p>It synthesizes aromatic amino acids. (D)</p> Signup and view all the answers

Which of the following compounds is an example of a stilbenoid?

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

What series of reactions occur after the formation of cinnamic acid?

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

How are stilbenoids chemically classified?

<p>As hydroxylated derivatives of stilbene (C)</p> Signup and view all the answers

What is one reported health benefit of resveratrol?

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

Which method is commonly used for the synthesis of umbelliferone?

<p>Pechmann condensation (D)</p> Signup and view all the answers

What characteristic distinguishes stilbenoids from other phytoalexins?

<p>Their common structure as stilbene (A)</p> Signup and view all the answers

What role do stilbenoids potentially play in tree diseases?

<p>They enhance resistance to certain diseases (D)</p> Signup and view all the answers

How do stilbenoids exert their biological activities?

<p>Through antimicrobial effects (B)</p> Signup and view all the answers

Flashcards

Shikimate Pathway

A metabolic pathway in plants that creates aromatic amino acids and phenylpropanoids.

Chorismate

A key intermediate in the Shikimate Pathway, used to build aromatic compounds.

Aromatic Amino Acids

Phenylalanine, tyrosine, and tryptophan, essential for proteins.

Phenylpropanoids

A group of plant compounds derived from phenylalanine, including lignin and anthocyanins.

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Mevalonate Pathway

A pathway for creating terpenoids/steroids, from mevalonic acid.

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Terpenoids

A large group of natural products, including limonene, and other plant compounds.

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Essential Amino Acids

Amino acids our bodies cannot make, need to be consumed.

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Phenylalanine

An aromatic amino acid in plants, building block in proteins and phenylpropanoids.

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Cinnamic Acid

A naturally occurring organic compound, the starting point for many plant compounds like lignin and flavonoids.

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Coumaric Acid

A type of cinnamic acid with an added hydroxyl group, crucial for building flavonoids.

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Monolignols

Building blocks for lignin, a structural component of plant cell walls.

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Cinnamaldehyde

A common fragrant compound, used to create the smell of cinnamon.

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What are phenylpropenes?

A group of plant compounds, including eugenol and safrole, found in essential oils, often contributing to aroma and flavors.

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Umbeliferone

A type of coumarin found in plants like carrots and coriander.

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What is coumaroyl-CoA?

A crucial intermediate in the production of chalcones, which are precursors for flavonoids.

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Chalcones

Precursors to flavonoids, a diverse group of plant pigments and antioxidants.

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What is the Shikimate Pathway?

The Shikimate Pathway is a metabolic route in plants, microorganisms, and fungi that produces aromatic amino acids (like phenylalanine, tyrosine, and tryptophan) and phenylpropanoids. Animals cannot perform this pathway.

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Tryptophan

Tryptophan is an aromatic amino acid synthesized through the Shikimate Pathway. It is vital for protein production and serves as a precursor for the plant hormone indoleacetic acid (IAA).

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Indoleacetic Acid (IAA)

Indoleacetic Acid (IAA), a plant hormone derived from tryptophan, plays a central role in plant growth, controlling cell expansion, maintaining apical dominance, and other regulatory processes.

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What are Phenylpropanoids?

Phenylpropanoids are a diverse group of plant compounds synthesized from phenylalanine. They have various functions, including defense against herbivores, microbial attack, ultraviolet radiation, and structural support, as well as acting as pigments and signaling molecules.

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PAL (Phenylalanine ammonia-lyase)

PAL is an enzyme that plays a crucial role in plant defense. It catalyzes the conversion of phenylalanine to cinnamic acid, the first step in the synthesis of many phenylpropanoids.

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What are lignans?

Lignans are a group of plant compounds that are derived from phenylalanine and act as antioxidants and phytoestrogens.

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What are the main classes of phytoestrogens?

The three main classes are lignans, isoflavones, and coumestans.

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What are the mammalian lignans?

Enterodiol and enterolactone are the mammalian forms of lignans, produced by gut bacteria.

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What are the main sources of lignans in the diet?

Flaxseed, sesame seeds, pumpkin seeds, rye, soybeans, broccoli, beans, and some berries.

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What are the two most common plant lignans?

Secoisolariciresinol and matairesinol are the most frequently found in foods.

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Stilbenoids

Naturally occurring phenolic compounds found in plants, derived from stilbene with various substituents.

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Phytoalexins

Antimicrobial compounds produced by plants in response to pathogen attack or stress, providing defense.

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Resveratrol

A phytoalexin found in grapes and other plants, known for its potential health benefits.

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Coumarin

A naturally occurring compound found in various plants, known for its fragrance and medicinal properties.

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What is the Pechmann Condensation?

A chemical reaction used to synthesize coumarin derivatives, specifically umbelliferone, from resorcinol and formylacetic acid.

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How do stilbenoids act as phytoalexins?

Stilbenoids are produced in plants when stressed, acting as antimicrobial compounds to fight off pathogens or toxins.

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What are some of the benefits associated with resveratrol?

Resveratrol has been linked to potential health benefits like anti-cancer, antiviral, neuroprotective, anti-aging, anti-inflammatory, and life-prolonging effects.

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Study Notes

Terrestrial Natural Product Chemistry

  • Shikimate Pathways (or Shikimic Acid Pathways): A crucial biosynthetic pathway in plants and some microbes, responsible for producing aromatic amino acids and secondary metabolites.
  • Shikimate pathway overview: Converts primary metabolites phosphoenolpyruvate and erythrose-4-phosphate to chorismate.
  • Chorismate's role: Essential for the biosynthesis of diverse aromatic plant metabolites, including phenylalanine, tyrosine, and tryptophan (essential for protein synthesis) and other compounds like tetrahydrofolate, ubiquinone, and vitamin K.
  • Phenylalanine's role: Used in protein synthesis and as a substrate for the phenylpropanoid pathway. This path creates a variety of secondary products like anthocyanins, lignin, growth promoters, and phenolics.
  • Indoleacetic acid: A plant hormone derived from tryptophan, essential for cell expansion, maintaining apical dominance, and other regulatory functions in plants.
  • Biosynthesis Pathways: Different pathways exist for different types of natural products - Mevalonate Pathways (terpenoids/steroids), Polyketide/acetogenin/acetate-malonate pathways (aromatic compounds), and Alkaloids Pathways (alkaloids)

### Phenylpropanoids

  • Definition: A diverse group of natural products.
  • Biosynthesis: Synthesized from phenylalanine or tyrosine amino acids through a series of enzymatic reactions.
  • Functions: Provide a diverse array of functions, including defense against herbivores, protection from microbial attack, structural components of cell walls, UV protection, pigments, and signaling molecules.

Coumarins

  • Biosynthesis: p-coumaric acid is hydroxylated in the 4-position.
  • Modifications: Can be further modified into hydroxylated derivatives.
  • Key Role: Production of chalcone. Achieving this involves adding three malonyl-CoA molecules then cyclizing into a second phenyl group.

Umbelliferone

  • Natural Product: 7-hydroxycoumarin.
  • Occurrence: Found in members of the Apiaceae family, like carrots and coriander.
  • Chemical Properties: Yellowish-white crystalline solid, with limited water solubility but increased solubility in ethanol. Strong absorption of UV light at specific wavelengths.
  • Uses: Composed in sunscreen creams and lotions due to UV absorption.

Umbelliferone Synthesis

  • Method: Traditionally made through the Pechmann condensation, involving resorcinol and formylacetic acid (formed from malic acid in situ).

Stilbenoids

  • Derivatives: Hydroxylated derivatives of stilbene.
  • Biosynthesis: Formed through an alternative cyclization of cinnammoyl-CoA or 4-coumaroyl-CoA.
  • Examples: Resveratrol, an example.
  • Properties: Secondary plant products involved in heartwood formation, acting as phytoalexins.
  • Biochemical class: Belong to the phenylpropanoid family, sharing biosynthetic pathways with chalcones.

Phytoalexins

  • Definition: Antimicrobial substances made by plants.
  • Formation: Accumulates rapidly in plant cells at sites of incompatible pathogen infection.
  • Diversity: Exhibit chemical diversity and are specific to certain plant species.
  • Classes: Some classes include terpenoids, glycosides, and alkaloids.
  • Role: Play a protective role in plant defense.

Resveratrol

  • Type: Phytoalexin produced by several plants.
  • Method of Production: Can be synthesized chemically as well.
  • Purpose: Sold as a nutritional supplement.
  • Health Benefits: Reported to have anti-cancer, antiviral, neuroprotective, anti-aging, and inflammatory effects.
  • Source: Found in the skin of red grapes.

Lignans

  • Definition: Chemical compounds found in plant foodstuffs.
  • Type: Phytoestrogens acting as antioxidants.
  • Biosynthesis Via: Formed by the dimerization or joining of substituted cinnamic alcohols.
  • Examples: Pinoresinol, podophyllotoxin, and steganacin.
  • Dietary Conversion: When consumed, they are converted into mammalian lignans (enterodiol and enterolactone) by intestinal bacteria.

Lignin

  • Complex Structure: A complex polymer made up of various repeating structural units and joined coniferyl/hydroxyconiferyl alcohols.
  • Role: Acts as a major structural component of the cell walls of plants.

Phenylpropenes

  • Other Derivatives: Includes eugenol, chavicol, safrole, and estragole.
  • Source: Derived from monolignols.
  • Role: Primary components of various essential oils.

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STK31003 Terrestrial Natural Product Chemistry PDF

Description

Explore the intricate shikimate pathway integral to plant metabolism. This quiz covers the conversion of primary metabolites into essential aromatic amino acids and their role in synthesizing secondary metabolites. Test your knowledge on the significance of phenylalanine and its derivatives in plant biology.

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