Flavonoids and Phenolic Compounds

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Questions and Answers

Which of the following statements correctly describes a phenolic compound?

  • It consists only of carbohydrates.
  • It contains a carbon ring with multiple double bonds.
  • It contains a benzene ring substituted with a ketone group.
  • It contains a benzene ring substituted with a hydroxyl group. (correct)

Flavones are characterized by a double bond between positions 2 and 3 of the C ring.

True (A)

What is the systematic name of phenol?

hydroxybenzene

Flavonols have a hydroxyl group in position ______ of the C ring.

<p>3</p> Signup and view all the answers

Match the following flavonoids with their characteristics:

<p>Flavanones = C ring is saturated, no double bond between positions 2 and 3 Isoflavones = Structurally similar to estrogens such as estradiol Flavonols = Have a hydroxyl group in position 3 of the C ring Flavanonols = 3-hydroxy derivatives of flavanones</p> Signup and view all the answers

What is the characteristic feature of flavanones?

<p>They have a saturated C ring. (A)</p> Signup and view all the answers

Isoflavones resemble estrogens such as estradiol.

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

What is the general formula of phenolic compounds mentioned?

<p>C6—C3—C6</p> Signup and view all the answers

Match the flavonoids with their descriptions:

<p>Flavones = Double bond between positions 2 and 3 Flavonols = Hydroxyl group in position 3 Flavanones = C ring is saturated Isoflavones = B ring attached to position 3</p> Signup and view all the answers

Which flavonoid is also known as dihydroflavonols?

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

Neoflavonoids are not considered polyphenolic compounds.

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

This structural feature of flavonoids, the double bond between positions 2 and 3, is lost in ______.

<p>Flavanones</p> Signup and view all the answers

Which group of flavonoids is characterized by having a hydroxyl group and might be glycosylated?

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

Which of the following best describes a distinguishing feature of flavanones?

<p>They have a saturated C ring. (C)</p> Signup and view all the answers

Isoflavones have structural similarities to estrogens.

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

The general formula for phenolic compounds is ______.

<p>C6—C3—C6</p> Signup and view all the answers

Match each subgroup of flavonoids with its description:

<p>Flavones = Double bond between positions 2 and 3 Flavonols = Hydroxyl group in position 3 Flavanones = C ring is saturated Isoflavones = Phytoestrogens</p> Signup and view all the answers

Which flavonoid subgroup is recognized for having highly diversified and multisubstituted structures?

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

Neoflavonoids are considered a subgroup of flavonoids.

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

In flavonols, the hydroxyl group appears in position ______ of the C ring.

<p>3</p> Signup and view all the answers

What unique feature is associated with the B ring in isoflavones?

<p>Attached to position 3 of the C ring</p> Signup and view all the answers

Which structure is characterized by having a ketone in position 4 of the C ring?

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

What is the primary structure of phenol?

<p>A benzene ring with a hydroxyl group (A)</p> Signup and view all the answers

All flavonoids contain a ketone group in their structure.

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

Identify the class of compounds that is characterized by having structural similarities to estrogens.

<p>Isoflavones</p> Signup and view all the answers

Match the flavonoids with their corresponding descriptions:

<p>Flavones = Double bond between positions 2 and 3 Flavonol = Hydroxyl in position 3 Flavanones = C ring saturated Isoflavones = Similar to estrogens</p> Signup and view all the answers

Which subgroup of flavonoids does NOT contain a double bond between positions 2 and 3?

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

Neoflavonoids are a category of polyphenolic compounds.

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

What modification distinguishes flavonols from flavones?

<p>Hydroxyl group in position 3</p> Signup and view all the answers

Match each flavonoid with their unique feature:

<p>Flavones = Contains a ketone group Flavanonols = 3-hydroxy derivatives of flavanones Isoflavones = B ring attached to C ring at position 3 Flavanones = C ring is saturated</p> Signup and view all the answers

Flashcards

Phenolic compound definition

A compound containing a phenol moiety, which is a benzene ring with a hydroxyl group.

Flavonoid subgroups (Flavones)

A subgroup of polyphenolic compounds with a double bond between carbons 2 and 3, and a ketone at position 4 of the C ring.

Flavonoid subgroups (Flavonols)

A subgroup of flavonoids, similar to flavones but with a hydroxyl group (OH) at position 3 of the C ring.

Isoflavones (phytoestrogens)

Flavonoids where the B ring is attached to position 3 of the C ring, structurally similar to estrogens.

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Neoflavonoids

A class of polyphenolic compounds; a subgroup of flavonoids.

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Phenol Moiety

A benzene ring with a hydroxyl group attached. This structure is the defining feature of phenolic compounds.

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Flavonoid General Formula

The general formula for flavonoids is (C6—C3—C6). This structure represents the three rings that make up most flavonoid molecules.

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Flavones

A type of flavonoid with a double bond between carbons 2 and 3, and a ketone at position 4 of the C ring.

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Flavonols

Similar to flavones, but with a hydroxyl group (OH) at position 3 of the C ring.

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Flavanones (Dihydro-flavones)

A type of flavonoid where the C ring is saturated, leading to no double bond between carbons 2 and 3.

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Flavanonols (Dihydroflavonols)

Flavanones with a hydroxyl group at position 3. Highly diverse and multisubstituted.

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Ruta Graveolens

A plant species known for its medicinal properties and often used in traditional medicine.

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Phenolic Compound

A compound that contains a phenol moiety (benzene ring with a hydroxyl group attached).

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Phytoestrogens

Plant compounds with estrogen-like activity, often found in isoflavones.

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What is a phenolic compound?

A compound containing a phenol moiety, which is a benzene ring with a hydroxyl group attached.

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What makes a flavonoid special?

Flavonoids are polyphenolic compounds with a specific structure: (C6—C3—C6), which represents three linked rings.

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Difference between flavones and flavonols?

Flavones have a double bond between carbons 2 and 3 and a ketone at position 4. Flavonols are similar, but have an additional hydroxyl group (OH) at position 3.

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What is the difference between flavones and flavanones?

Flavanones have a saturated C ring, meaning the double bond between carbons 2 and 3 is lost. Flavones have this double bond.

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What are flavanonols?

Flavanonols are 3-hydroxy derivatives of flavanones, meaning they have a hydroxyl group at position 3.

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What are isoflavones?

Isoflavones have their B ring attached to position 3 of the C ring, which makes them structurally similar to estrogens.

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Why are isoflavones called phytoestrogens?

Isoflavones are called phytoestrogens because they have a structure similar to estrogens, but they come from plant sources.

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What are neoflavonoids?

Neoflavonoids are a class of polyphenolic compounds, and are considered a subgroup of flavonoids.

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What is Ruta Graveolens?

Ruta Graveolens is a plant species known for its medicinal properties and often used in traditional medicine.

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What is the difference between flavones and flavanonols?

Flavones have a double bond between carbons 2 and 3 and a ketone at position 4. Flavanonols have the same structure as flavones but with an additional hydroxyl group (OH) at position 3 of the C ring.

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Study Notes

Flavonoids

  • Flavonoids are a class of polyphenolic secondary metabolites found in plants.
  • Humans commonly consume them in their diet.
  • Flavonoids have the general formula (C6 -C3 - C6).
  • Phenolic compounds contain a phenol moiety.
  • Phenol is a benzene ring substituted with a hydroxyl group.
  • The systematic name for phenol is hydroxybenzene.

Chemical Classification of Natural Phenolic Compounds

  • Phenolics are categorized into simple phenols, polyphenols, flavonoids, and non-flavonoids.
  • Phenolic acids include hydroxycinnamic acids (e.g., caffeic acid, p-coumaric acid, ferulic acid) and hydroxybenzoic acids (e.g., gallic acid, protocatechuic acid).
  • Coumarins include coumarin, psoralen, scopaletin, and esculetin.
  • Flavonoids include flavones, flavonols, flavanones, flavanols, isoflavonols, anthocyanins, and chalcones.
  • Non-flavonoids include tannins, lignans, and stilbenes.

Flavonoid Classification

  • 1-Flavones have a double bond between positions 2 and 3 and a ketone in position 4 of the C ring.
  • 2-Flavonols have a hydroxyl group in position 3 of the C ring, which can be glycosylated.
  • 3-Flavanones have a saturated C ring, and the double bond between positions 2 and 3 is absent.
  • 4-Flavanonols are 3-hydroxy derivatives of flavanones.
  • 5-Isoflavones have the B ring attached to position 3 of the C ring and are structurally similar to estrogens (phytoestrogens).
  • 6-Neoflavonoids are a class of polyphenolic compounds.

Pharmacological Effect of Flavonoids

  • Flavonoids have various pharmacological effects including:
    • Anti-oxidant
    • Anti-inflammatory
    • Immune defense
    • Anti-microbial
    • Anti-mutagenic
    • Anti-carcinogenic
    • Anti-hepatic

Example Flavonoids

  • Quercetin
  • Kaempferol

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