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Questions and Answers
What is the primary pharmacological activity of Passion Flower?
What is the primary pharmacological activity of Passion Flower?
- Sedative and anxiolytic (correct)
- Antioxidant
- Antibiotic
- Anti-inflammatory
Which of the following flavonoids is NOT listed as part of the chemical composition of Passion Flower?
Which of the following flavonoids is NOT listed as part of the chemical composition of Passion Flower?
- Shaftoside
- Isovitexin
- Isoorientin
- Quercetin (correct)
How does Passion Flower show its activity in the body?
How does Passion Flower show its activity in the body?
- By modulation of the GABA system (correct)
- By enhancing the norepinephrine system
- By inhibiting the dopamine system
- By stimulating the serotonin system
Which of the following constituents is found in Passion Flower in a minor quantity?
Which of the following constituents is found in Passion Flower in a minor quantity?
What other drug is commonly combined with Passion Flower for its sedative effects?
What other drug is commonly combined with Passion Flower for its sedative effects?
Which of the following statements about the chemical composition of Passion Flower is incorrect?
Which of the following statements about the chemical composition of Passion Flower is incorrect?
Which part of Passion Flower is primarily used for medicinal purposes?
Which part of Passion Flower is primarily used for medicinal purposes?
What is a characteristic of flavonoid-containing drugs like Passion Flower?
What is a characteristic of flavonoid-containing drugs like Passion Flower?
What pharmacological activity is thyme known for?
What pharmacological activity is thyme known for?
Which flavonoid is found in Field Horsetail (Equisetum arvense)?
Which flavonoid is found in Field Horsetail (Equisetum arvense)?
What is a traditional use of Equisetum arvense?
What is a traditional use of Equisetum arvense?
What type of compounds contribute to the spasmolytic activity of thyme?
What type of compounds contribute to the spasmolytic activity of thyme?
Which component does NOT typically belong to the chemical composition of Equisetum arvense?
Which component does NOT typically belong to the chemical composition of Equisetum arvense?
What is the highest percentage of silica (SiO2) found in Equisetum arvense?
What is the highest percentage of silica (SiO2) found in Equisetum arvense?
Which of the following is NOT a use of Field Horsetail in cosmetology?
Which of the following is NOT a use of Field Horsetail in cosmetology?
What type of toxicity is associated with Equisetum palustre?
What type of toxicity is associated with Equisetum palustre?
What is a pharmacological use of Roman Camomile?
What is a pharmacological use of Roman Camomile?
Which flavonoid is notably found in Immortelle flower?
Which flavonoid is notably found in Immortelle flower?
Which of the following is an essential oil component found in Yarrow?
Which of the following is an essential oil component found in Yarrow?
What is traditionally used for treating gastrointestinal disorders?
What is traditionally used for treating gastrointestinal disorders?
What type of compound is predominantly found in the chemical composition of Roman Camomile?
What type of compound is predominantly found in the chemical composition of Roman Camomile?
Which property is NOT associated with Immortelle flower?
Which property is NOT associated with Immortelle flower?
What are sesquiterpene lactones primarily known for?
What are sesquiterpene lactones primarily known for?
Which traditional use is linked to Immortelle flower?
Which traditional use is linked to Immortelle flower?
Which is a characteristic of flavonoids found in Yarrow?
Which is a characteristic of flavonoids found in Yarrow?
What role do flavonoids from Roman Camomile play?
What role do flavonoids from Roman Camomile play?
Which class of flavonoids is characterized by the absence of a 2,3-double bond?
Which class of flavonoids is characterized by the absence of a 2,3-double bond?
What is the primary role of flavonoids in plants?
What is the primary role of flavonoids in plants?
Which of the following describes the structural feature of flavonoids?
Which of the following describes the structural feature of flavonoids?
Which of the following flavonoids is known to accumulate in the leaf cuticle?
Which of the following flavonoids is known to accumulate in the leaf cuticle?
What determines the glycosidic forms of flavonoids?
What determines the glycosidic forms of flavonoids?
Which class of flavonoids is primarily found in the families Lamiaceae, Rutaceae, and Asteraceae?
Which class of flavonoids is primarily found in the families Lamiaceae, Rutaceae, and Asteraceae?
What is a significant feature of chalcones in flavonoid classification?
What is a significant feature of chalcones in flavonoid classification?
In which class of flavonoids would you find compounds like catechin and leucocyanidin?
In which class of flavonoids would you find compounds like catechin and leucocyanidin?
Which of the following can be a product of flavonoid bonding?
Which of the following can be a product of flavonoid bonding?
Which of the following is a characteristic of isoflavones?
Which of the following is a characteristic of isoflavones?
Which flavonoid structure typically has at least one asymmetric center?
Which flavonoid structure typically has at least one asymmetric center?
Which of the following statements about structural diversity in 2-phenylchromones is true?
Which of the following statements about structural diversity in 2-phenylchromones is true?
What is the significance of structural features in flavonoids regarding chemotaxonomy?
What is the significance of structural features in flavonoids regarding chemotaxonomy?
Which variant of flavonoids can exhibit a C-C type interflavonoid linkage?
Which variant of flavonoids can exhibit a C-C type interflavonoid linkage?
What types of sugars can flavonoid glycosides consist of?
What types of sugars can flavonoid glycosides consist of?
Which bond is characteristic of C-glycosides in flavonoids?
Which bond is characteristic of C-glycosides in flavonoids?
What is the common property of flavonoids involving vascular health?
What is the common property of flavonoids involving vascular health?
Which structural elements are required for optimal free radical scavenging activity in flavonoids?
Which structural elements are required for optimal free radical scavenging activity in flavonoids?
Which chromatographic techniques are used for the separation and purification of flavonoids?
Which chromatographic techniques are used for the separation and purification of flavonoids?
How are glycosides extracted efficiently?
How are glycosides extracted efficiently?
What are common methods of qualitative analysis for flavonoids?
What are common methods of qualitative analysis for flavonoids?
Which flavonoid is extracted from buckwheat?
Which flavonoid is extracted from buckwheat?
What biological property do several flavonoids exhibit regarding enzymes?
What biological property do several flavonoids exhibit regarding enzymes?
Which structural adaptation makes rutin more soluble?
Which structural adaptation makes rutin more soluble?
Which compound is known as a citroflavonoid derived from citrus fruits?
Which compound is known as a citroflavonoid derived from citrus fruits?
What common pharmacological application do flavonoids have?
What common pharmacological application do flavonoids have?
What solvent types do flavonoid glycosides typically dissolve in?
What solvent types do flavonoid glycosides typically dissolve in?
Flashcards
What are flavonoids?
What are flavonoids?
Plant pigments responsible for colors in flowers, fruits, and sometimes leaves. They absorb near-UV radiation to attract insects and protect plant tissue.
What are chalcones and aurones?
What are chalcones and aurones?
A group of flavonoids that give yellow color to plants.
What is a copigment?
What is a copigment?
Flavonoids like anthocyanins can act as copigments, enhancing the color of other pigments.
Where are flavonoids found?
Where are flavonoids found?
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Where are glycosidic flavonoids and aglycones found?
Where are glycosidic flavonoids and aglycones found?
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What is the basic structure of flavonoids?
What is the basic structure of flavonoids?
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How are flavonoids classified?
How are flavonoids classified?
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What are some examples of 2-phenylchromones?
What are some examples of 2-phenylchromones?
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What are isoflavones and isoflavanones?
What are isoflavones and isoflavanones?
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What are chalcones and dihydrochalcones?
What are chalcones and dihydrochalcones?
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What are aurones?
What are aurones?
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What are anthocyanidins?
What are anthocyanidins?
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What are biflavonoids?
What are biflavonoids?
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What are apigenin and luteolin?
What are apigenin and luteolin?
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What are kaempferol and quercetin?
What are kaempferol and quercetin?
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Biflavonoid
Biflavonoid
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Biflavanone
Biflavanone
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Flavone-flavanone
Flavone-flavanone
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Flavonoid glycosides
Flavonoid glycosides
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C-glycosidic flavonoid
C-glycosidic flavonoid
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Flavonoid glycosides solubility
Flavonoid glycosides solubility
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Flavonoid aglycone solubility
Flavonoid aglycone solubility
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Chalcone
Chalcone
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Aurone
Aurone
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Citroflavonoid
Citroflavonoid
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Hesperidin
Hesperidin
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Ginkgo biloba extract
Ginkgo biloba extract
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Ginkgolide B
Ginkgolide B
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Rutin
Rutin
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Rutin (Sophora japonica)
Rutin (Sophora japonica)
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What is Passion Flower?
What is Passion Flower?
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What are the main active compounds in Passion Flower?
What are the main active compounds in Passion Flower?
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What are the active constituents in Passion Flower?
What are the active constituents in Passion Flower?
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What are the pharmacological activities of Passion Flower?
What are the pharmacological activities of Passion Flower?
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What is Thyme?
What is Thyme?
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What are the primary active compounds in Thyme?
What are the primary active compounds in Thyme?
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What are the traditional medicinal uses of Thyme?
What are the traditional medicinal uses of Thyme?
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What are some important precautions when using herbs like Thyme?
What are some important precautions when using herbs like Thyme?
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What is Thyme used for?
What is Thyme used for?
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What are the benefits of Field Horsetail?
What are the benefits of Field Horsetail?
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What is the difference between Field Horsetail and Marsh Horsetail?
What is the difference between Field Horsetail and Marsh Horsetail?
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What are Apigenin and Luteolin and what do they do?
What are Apigenin and Luteolin and what do they do?
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Why are flavonoids important?
Why are flavonoids important?
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What are the medicinal properties of thyme essential oil?
What are the medicinal properties of thyme essential oil?
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How does Field Horsetail benefit hair, nails, and skin?
How does Field Horsetail benefit hair, nails, and skin?
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What properties do Thyme and Field Horsetail share?
What properties do Thyme and Field Horsetail share?
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Apigenin and Luteolin glycosides
Apigenin and Luteolin glycosides
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6-Methoxylated Flavones
6-Methoxylated Flavones
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Apigenin-7-glucoside
Apigenin-7-glucoside
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Kaempferol and Quercetin glycosides
Kaempferol and Quercetin glycosides
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Study Notes
Flavonoids - General Overview
- Flavonoids are universal plant pigments
- They are responsible for the color of flowers, fruits, and sometimes leaves
- Yellow flavonoids include chalcones and aurones
- Red, blue, or purple flavonoids are anthocyanins
- Flavonoids can sometimes act as copigments, affecting the color of other pigments (e.g., protecting anthocyanins)
- Flavonoids are widespread in the plant kingdom, except for algae
- Structural diversity of flavonoids is maximal in angiosperms
- Glycosidic forms of flavonoids are water-soluble and accumulate in vacuoles
- Free aglycones are located in leaf cuticles
Flavonoid Chemistry and Classification
- Flavonoids have a "2-phenylchromane" skeleton
- They are classified based on the degree of oxidation of the "pyran" ring
- 2-phenylchromones include flavones, flavonols, flavanones, and dihydroflavonols
- 2-phenylchromanes include flavans, flavan-3-ols, and flavan-3,4-diols
- 3-phenylchromones include isoflavones and isoflavanones
- Chalcones and dihydrochalcones have an open pyran ring
- 2-benzylidene coumaranones are also known as aurones
- 2-phenylbenzopyriliums are anthocyanins
Flavonoid Structure Diversity
- Substitution at C-5 and C-7 by -OH groups occurs in 90% of flavonoids.
- Flavonoids can be free or etherified (-OMe)
- Commonly, they are engaged in glycosidic linkages (O-glc...)
- These can also be substituted at C-6 and C-8;
- Â Free or etherified -OH groups
- Isoprenylation
- Methylation
- C-glycosylation and substitution at B ring
- Examples of B-ring substitutions include C-4'-OH, 3',4'-di OH, and 3',4',5'-tri OH.
Flavonoid Characterization
- Flavones and dihydroflavonols are characterized by the absence of a 2,3-double bond
- At least one asymmetric center is present
- C-2 is generally in the S configuration
Flavonoid-3-ol and Flavon-3,4-diols
- These are 2-phenylchromanes
- Examples include catechin and leucocyanidin
3-Phenylchromones (Isoflavonoids)
- Isoflavones and isoflavanones are included in this category
Chalcones
- The C-ring of chalcones is open
- They are characterized by a 3C-chain with a ketone function and alpha,beta-unsaturation
2-Benzylidenecoumaranone (Aurones)
- Hispidol is an example in this category
Biflavonoids
- Two flavonoid structures are connected to each other
- Interflavonoid linkages can be C-C type (e.g., amentoflavone) or C-O-C type (e.g., hinokiflavone).
- The two flavonoid units may or may not be the same type (e.g., biflavone, biflavanone, flavone-flavanone)
Flavonoid Glycosides
- Flavonoid glycosides (O-glycosides) are mono, di, and trisaccharides
- Common sugars include D-glucose, D-galactose, D-allose, D-apiose, L-arabinose, L-rhamnose, and D-xylose.
- Uronic acids (D-glucuronic acid, D-galacturonic acid) are also present
- Glycosation often happens at C-7 (OH) in flavones or C-3 (OH) in flavonols
- Aliphatic acids (e.g., acetic, malonic, tiglic) and aromatic acids (e.g., gallic, benzoic, cinnamic) can also be attached
- Flavonoid glycosides also have C-glycosides where the glycosidation bond occurs between the anomeric carbon of the sugar and C-6 or C-8 of the aglycone. (e.g., orientin and saponarin )
Biosynthetic Origin of Flavonoids
- Flavonoids are biosynthesized from different starting points, leading to various classes.
Flavonoid Physicochemical Properties
- Flavonoid glycosides are generally soluble in water and alcohols (e.g., ethanol, methanol).
- Rutin and hesperidin are exceptions and are only sparingly soluble.
- Aglycones are generally soluble in non-polar solvents.
- Flavonoids that have at least one free phenolic group dissolve in alkaline hydroxide solutions.
- Glycosides are usually extracted using mixtures of acetone or ethanol/methanol/water.
- Common fractionation methods include liquid-liquid extraction (using immiscible solvents like petroleum ether, diethyl ether, dichloromethane, and ethyl acetate), to separate flavonoids from plant material
- Chromatographic purification can be used to separate flavonoids (e.g. polyamide, sephadex, silica gel)
- Qualitative analysis (TLC) and quantitative analysis (spectrophotometry, HPLC-DAD) are used.
Flavonoids - Biological properties
- Flavonoids have various biological properties and uses, including reducing capillary fragility and permeability.
- They act as Vitamin P, venous tonics, and can be used as topical agents in phlebology.
- They are used for treating symptoms of venous and lymphatic insufficiency, acute piles, metrorrhagias, lymphedema.
- Flavonoids also demonstrate free radical scavenging activity, structural requirements include two ortho-hydroxyl groups on the B ring, ketone function at C-4, and 2,3-unsaturation.
- Some flavonoids inhibit or stimulate different enzymes (e.g., CAMP phosphodiesterase, aldose-reductase, lipooxygenase, cyclooxygenase, proline hydroxylase)
- Other flavonoid properties include anti-inflammatory, anti-allergic, hepatoprotective, antispasmodic, blood cholesterol-decreasing, diuretic, antibacterial, antiviral, and cytostatic activity
Flavonoids - Chief Flavonoids on the Market
- Citroflavonoids, isolated from citrus fruits
- Rutin, from various plants (e.g., Japanese pagoda tree, buckwheat)
- Flavonoids are extracted from pericarp and pulp as Ca and Mg derivatives
- Flavonoids from these sources can be used alone or in combination with other compounds Also used to treat and prevent conditions like leg symptoms of chronic venous insufficiency, and the acute attack of piles.
Flavonoid-Containing Drugs
- Different plants contain various flavonoid concentrations.
- These flavonoids can differ in the way they are used, and in their chemical composition.
- Examples include: Ginkgo biloba (leaves), Passiflora incarnata (aerial parts), Thymus vulgaris (aerial parts), Equisetum arvense (aerial parts), Chamaemelum nobile (flowers), and Achillea millefolium (flowers), and Helichrysum plicatum (flowers).
- Some plants also have toxicity concerns related to their flavonoid content.
Flavonoid toxicity
- Some flavonoids can be toxic, especially as concerns some plants used in livestock, or as adulterants of other products
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