PHARMACOGNOSY I (6)
Page 1: Introduction to Flavonoid Glycosides
Slide Title
PHARMACOGNOSY I PHAR301
Lecturer: Dr. Beste Atli
Topic: Flavonoid Glycosides
Page 2: General Characteristics of Flavonoids
Solubility
Flavonoid glycosides are soluble in water and water-alcohol mixtures.
Insoluble in organic solvents.
Aglycones are soluble in non-polar solvents.
Crystallization
Mostly crystallized compounds that yield a yellow solution in alkaline medium.
Addition of acid causes the yellow color to disappear.
Page 3: Extraction Methods for Flavonoids
Techniques Used
Different extraction methods employed when both flavonoids and glycosides are present.
Elution with:
Acetone, ethanol, or methanol-aqueous solutions.
Liquid-liquid extraction techniques (e.g., petroleum ether for chlorophyll, diethyl ether, or CHCl3 for aglycones).
Page 4: Concentration Technique
Steps Involved
Begin with concentrated extract (acetone-, ethanol-, or methanol-aqueous solutions) to isolate residual components (e.g., pigments).
Use CHCl3 or DEE for separation of free flavonoids.
Employ EtOAc to isolate glycosides.
Page 5: Types of Flavonoids and Their Solvents
Classification of Flavonoids
Discusses various types such as:
Isoflavones
Flavanones
Dihydroflavonol
Methylated flavone/flavonol derivatives
Common solvents: acetone, alcohol, water.
Page 6: Chromatographic Techniques
Separation Processes
Various chromatographic methods employed for the separation and purification process including:
Polyamide
Sephadex
Silica gel
Alumina (Al2O3)
HPLC.
Page 7: Determination Reactions for Glycosides
Chromatographic Identification
Chromatographic methods give fluorescence under UV light.
In alkaline medium, a yellow color indicates the presence of certain compounds.
Aurones and chalcones can be visually detected with ammonia vapors (producing orange/red colors).
Page 8: Color Tests for Flavonoids
Reagent Specific Tests
1% AlCl3/EtOH gives a yellow fluorescence for flavones.
1% PbOAc indicates flavonols with an orange color.
1% FeCl3 detects dihydro derivatives (green) and polyhydroxy derivatives (blue).
Page 9: Classical Color Reactions for Antioxidants
Specific Reactions
Cyanidin reaction (Shinoda reaction).
Color reactions with HCl and Mg/Zn powder facilitate color identification:
Flavones yield orange, flavonols yield red, flavanones yield purple, chalcones yield colorless.
Page 10: Further Color Reactions
Specific Tests
In alkaline conditions, flavones with H2SO4 yield yellow while chalcones with SbCl5/CCl4 yield red-violet.
Boric acid in dilute H2SO4 and FeCl3 tests provide color indications of hydroxyl groups.
Page 11: Identification Tests for Anthocyanins
Test Procedures
Use of diluted HCl generates red, NaOH produces blue, and lead acetate gives green colors for identification.
Reaction with amyl alcohol accompanied by heating leads to specific coloration (wine-red, pink-red).
Page 12: Quantitative Determination
Techniques
Use of colorimeters for % transmission readings, calibrated at 740 nm with specific sample preparations homing on red wavelengths.
Employing HPLC for sample filtration.
Page 13: Biological Activities of Glycosides
Highlighted Activity: Vitamin P
Structures with hydroxyl groups at positions 3', 4' reduce capillary permeability.
Associated with treatments for circulatory disorders (e.g., arteriosclerosis, varicose veins).
Sources include orange, lemon, rose hip, and red pepper.
Page 14: Diuretic and Diaphoretic Effects
Notable Compounds
Luteolin, apigenin, rutin, kaempferol, quercetin noted for diuretic properties.
Commonly used plants include Chamomillae flos and Tiliae flos.
Page 15: Antispasmodic Activities
Key Plants
Chamomillae flos, Tiliae folium, Rutae herba, Crataegi flos, and Viburni cortex recognized for antispasmodic effects.
Page 16: Chemical Structures
Structure Examples
Explains the structural characteristics and hydroxyl groups in compounds such as Quercetol and Rutin which influence their functions.
Page 17: Anti-inflammatory Properties
Highlighted Compounds
Discusses Apigenin and Hypolaetin-8-glucuroside for their anti-inflammatory benefits.
Page 18: Antimicrobial Effects
Summary of Effects
Compounds like Rutin and Quercetol described for their antibacterial, antifungal, and antiviral properties.
Phytoalexins are categorized by their unique structures.
Page 19: Antihistaminic Effects
Notable Plant
Scutellaria baicalensis identified for its antihistamine effects.
Page 20: Estrogenic and Antiestrogenic Properties
Isoflavonoids
Examples include Glycine max (soybean), Lepidium capitatum, and Trifolium repens.
Page 21: Insecticidal Effects
Example Compounds
Rotenoids detailed for their insecticide effects, particularly those with tetrahydrofurane structure from Derris eliptica.
Page 22: Cardiovascular Actions
Heart Health
Crataegus monogyna mentioned for effects on heart contractions & as a coronary vasodilator with antiarrhythmic properties.
Page 23: Purgative Properties
Caution
Noted that misuse is unauthorized (referring likely to Prunus japonica).
Page 24: Hepatoprotective Properties
Specific Compounds
Flavonolignans (Silybum marianum) detailed for their liver-protective functions.
Page 25: Anthocyanins as Dyes
Industrial Uses
Highlights practical uses of anthocyanins from plants (e.g., red cabbage, grape) in coloration within industries.
Page 26: Therapeutic Applications
Specific Treatments
Target conditions like capillary and venous disorders, my having symptoms like leg pain, weakness, and muscle cramps.
Page 27: Therapeutic Uses Continued
Specific Applications
Addressing menorrhagia, impaired retinal circulation, and symptoms associated with menopause through products like Diosmin and Rutin.
Page 28: Flavonoid-Bearing Plants
Example and Use
Ginkgo biloba (Ginkgoaceae) mentioned for its medicinal properties and preparations from the leaves.
Page 29: Ginkgo Compounds
Active Components
Bilobalide and ginkgolides, as well as flavonoid derivatives like Quercetin.
Page 30: Ginkgo Effects
Health Benefits
Mainly used for cognitive issues including amnesia, tinnitus, and dementia.
Page 31: Tebokan® and Its Uses
Product Overview
Tebokan® designed for symptoms relating to brain and limb perfusion disorders, aiding in memory and anti-vertigo functionality.
Page 32: Passiflora incarnata
Characteristics
Details features of the purple passion flower including key constituents like Vitexin.
Page 33: Thymus vulgaris Overview
Overview
Common thyme noted for its medicinal uses; includes its derivatives and oil extracts.
Page 34: Chemical Structures of Thymus
Relevant Compounds
Attributes of apigenin and luteolin are discussed, along with their significance.
Page 35: Thyme Species
Variants of Thyme
Lists known species with noted uses, such as Coridothymus capitatus and Thymbra spicata.
Page 36: Thyme Species Continued
Additional Species
Continuation of thyme species identification.
Page 37: Citrus Family Overview
Highlighted Species
Discusses various Citrus species and their uses in therapy, including drug names and origins.
Page 38: Flavonoid Structures in Citrus
Compounds
Representation of specific flavonoids such as Rutin and Diosmin from citrus sources.
Page 39: Silybum marianum Overview
Key Characteristics
Description of the plant family, name, and preparation in pharmaceutical forms.
Page 40: Silymarin Composition
Active Components
Silymarin acts on the liver, constituting 1.5-3% of the drug composition from flavonolignans.
Page 41: Achillea millefolium Overview
Identification
Common yarrow, its family, and drug uses highlighted.
Page 42: Active Constituents of Achillea
Therapeutic Activities
Discusses essential oils and their various therapeutic benefits including choleretic and anti-inflammatory properties.
Page 43: Equisetum arvense Overview
Characteristics
Describes the field horsetail, its height and structure, and key family classification.
Page 44: Morphology of Equisetum
Visual Description
Detailed examination of the morphology with focus on reproductive structures and characteristics during seasons.
Page 45: Growth Features
Botanical Attributes
Addresses the clear distinction of fertile and sterile forms in horsetail plants.
Page 46: Chemical Structures
Key Compounds
Highlights the structures of Kaempferol and Quercetin derivatives and their relevance in pharmacognosy.