This presentation is one topic of a course given to pharmacy students (Pharmacognosy II). It gives a general information about flavonoids, definition, classification, pharmacological activity, identification and examples of drugs containing flavonoids
Glycosides are organic natural compounds found in many plants and some animals. They contain a sugar (glycone) moiety and a non-sugar (aglycone or genin) moiety linked by a glycosidic bond. The sugar is usually beta-D-glucose but can also be galactose, mannose, rhamnose, or digitoxose. Glycosides have therapeutic effects due to the aglycone part, and the sugar moiety facilitates absorption and transport of the aglycone. Glycosides are hydrolyzed to release the active aglycone. They are used traditionally and in modern medicines for various purposes such as cardiac effects, laxatives, analgesics, and
The document describes different types of glycosides, which are compounds consisting of a sugar (glycon) bonded to another part (aglycon). Some examples of glycosides mentioned include:
- Anthraquinone glycosides like senna
- Sterol or cardiac glycosides like digitalis
- Saponine glycosides like liquorice
- The document also discusses different types of sugars that can form the glycon portion (glucose, rhamnose, pentose, fructose, arabinose) and different bonds between the glycon and aglycon (C-glycosides, N-glycosides).
- Some common uses of glycosides are as laxatives, anti
Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.A glycoside is a molecule consisting of a sugar and a non-sugar group, called an aglycone. The sugar group is known as the glycone and can consist of a single sugar group or several sugar groups. The sugars is in its cyclic form and is covalently attached to the aglycon through the hydroxyl group of the hemiactal function.
There are many different kinds of aglycones. It can be a terpene, a flavonoid, a coumarin or practically any other natural occurring product (se figure 1)
The glycone can be attached to the aglycon in many different ways. The most common bridging atom is oxygen (O-glycoside), but it can also be sulphur (S-glycoside), nitrogen (N-glycoside) or carbon (C-glycoside). In general, one distinguishes between ฮฑ-Glycosides and ฮฒ-glycosides, depending on the configuration of the hemiactal hydroxyl group. The majority of the naturally occurring glycosides are ฮฒ-glycosidesGenerally glycosides are more polar than the aglycones and as a result glycoside formation usually increases water solubility. This may allow the producing organism to transport and store the glycoside more efficiently
Many biologically active compounds are glycosides. The pharmacological effects are largely determined by the structure of the aglycone.
Glycosides comprise several important classes of compounds such as hormones, sweeteners, alkaloids, flavonoids and antibiotics
This practical manual is prepared for academic purpose only and contains introduction and detail methodology regarding determination of numbers of starch grains by Lycopodium spore method, along with dummy readings to facilitate understanding of calculations thereof.
The document discusses two types of catechu: black catechu and pale catechu. Black catechu is produced from the heartwood of Acacia catechu through boiling and extraction. It contains catechin and turns black due to reaction with iron during production. Pale catechu comes from the leaves and shoots of Uncaria gambier through boiling and extraction. It is yellow-green in color and contains catechins, catechutannic acid, and catechu red. Both are used as astringents and in industries like dyeing and tanning.
The document discusses the chemistry and biosynthesis of various glycosides. It begins by defining glycosides as molecules composed of a sugar molecule (glycone) linked to a non-sugar molecule (aglycone). It then discusses the chemistry and sources of several classes of glycosides - cardiac glycosides, sennosides, steroidal saponin glycosides like diosgenin, hecogenin and sarsapogenin. The biosynthesis of these glycosides involves the transfer of a sugar molecule from a UDP-sugar to the aglycone, catalyzed by glycosyltransferases. Key cardiac glycosides discussed are digoxin and digitoxin. Sennosides are anthraquinone glycos
1. Glycosides are organic compounds found in plants and animals that contain a sugar (glycone) and non-sugar (aglycone or genin) portion. Upon hydrolysis, the sugar and non-sugar portions separate.
2. There are several types of glycosides based on the atom involved in the glycosidic linkage between the glycone and aglycone, including O-, C-, S-, and N-glycosides.
3. Two common cardiac glycoside drugs that contain glycosides are Digitalis and Aloe. Digitalis contains compounds like digitoxin and gitoxin that have cardiac effects. Aloe contains compounds like aloin that have laxative effects.
Glycosides are organic natural compounds found in many plants and some animals. They contain a sugar (glycone) moiety and a non-sugar (aglycone or genin) moiety linked by a glycosidic bond. The sugar is usually beta-D-glucose but can also be galactose, mannose, rhamnose, or digitoxose. Glycosides have therapeutic effects due to the aglycone part, and the sugar moiety facilitates absorption and transport of the aglycone. Glycosides are hydrolyzed to release the active aglycone. They are used traditionally and in modern medicines for various purposes such as cardiac effects, laxatives, analgesics, and
The document describes different types of glycosides, which are compounds consisting of a sugar (glycon) bonded to another part (aglycon). Some examples of glycosides mentioned include:
- Anthraquinone glycosides like senna
- Sterol or cardiac glycosides like digitalis
- Saponine glycosides like liquorice
- The document also discusses different types of sugars that can form the glycon portion (glucose, rhamnose, pentose, fructose, arabinose) and different bonds between the glycon and aglycon (C-glycosides, N-glycosides).
- Some common uses of glycosides are as laxatives, anti
Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.A glycoside is a molecule consisting of a sugar and a non-sugar group, called an aglycone. The sugar group is known as the glycone and can consist of a single sugar group or several sugar groups. The sugars is in its cyclic form and is covalently attached to the aglycon through the hydroxyl group of the hemiactal function.
There are many different kinds of aglycones. It can be a terpene, a flavonoid, a coumarin or practically any other natural occurring product (se figure 1)
The glycone can be attached to the aglycon in many different ways. The most common bridging atom is oxygen (O-glycoside), but it can also be sulphur (S-glycoside), nitrogen (N-glycoside) or carbon (C-glycoside). In general, one distinguishes between ฮฑ-Glycosides and ฮฒ-glycosides, depending on the configuration of the hemiactal hydroxyl group. The majority of the naturally occurring glycosides are ฮฒ-glycosidesGenerally glycosides are more polar than the aglycones and as a result glycoside formation usually increases water solubility. This may allow the producing organism to transport and store the glycoside more efficiently
Many biologically active compounds are glycosides. The pharmacological effects are largely determined by the structure of the aglycone.
Glycosides comprise several important classes of compounds such as hormones, sweeteners, alkaloids, flavonoids and antibiotics
This practical manual is prepared for academic purpose only and contains introduction and detail methodology regarding determination of numbers of starch grains by Lycopodium spore method, along with dummy readings to facilitate understanding of calculations thereof.
The document discusses two types of catechu: black catechu and pale catechu. Black catechu is produced from the heartwood of Acacia catechu through boiling and extraction. It contains catechin and turns black due to reaction with iron during production. Pale catechu comes from the leaves and shoots of Uncaria gambier through boiling and extraction. It is yellow-green in color and contains catechins, catechutannic acid, and catechu red. Both are used as astringents and in industries like dyeing and tanning.
The document discusses the chemistry and biosynthesis of various glycosides. It begins by defining glycosides as molecules composed of a sugar molecule (glycone) linked to a non-sugar molecule (aglycone). It then discusses the chemistry and sources of several classes of glycosides - cardiac glycosides, sennosides, steroidal saponin glycosides like diosgenin, hecogenin and sarsapogenin. The biosynthesis of these glycosides involves the transfer of a sugar molecule from a UDP-sugar to the aglycone, catalyzed by glycosyltransferases. Key cardiac glycosides discussed are digoxin and digitoxin. Sennosides are anthraquinone glycos
1. Glycosides are organic compounds found in plants and animals that contain a sugar (glycone) and non-sugar (aglycone or genin) portion. Upon hydrolysis, the sugar and non-sugar portions separate.
2. There are several types of glycosides based on the atom involved in the glycosidic linkage between the glycone and aglycone, including O-, C-, S-, and N-glycosides.
3. Two common cardiac glycoside drugs that contain glycosides are Digitalis and Aloe. Digitalis contains compounds like digitoxin and gitoxin that have cardiac effects. Aloe contains compounds like aloin that have laxative effects.
Pharmacognosy of Atropa belladona, biological source, geographical source, chemical constituents, uses, morphology of leaves, flower, fruits of belladona, deadly night shade leaves, chemical test, microscopy, T.S of leaves
This document discusses tropane alkaloids, specifically atropine alkaloid. It summarizes that atropine alkaloid is mainly found in plants from the solanaceae family, like Atropa belladona and Datura stromonium. It then describes the isolation, biosynthesis, identification tests, chemistry and properties, structure-activity relationships, uses, and mechanism of action of atropine alkaloid.
This document discusses glycosides, which are organic natural compounds found in many plants and some animals. Glycosides are composed of a sugar (glycone) and non-sugar (aglycone) moiety linked together by a glycosidic linkage. The sugar is often glucose but can also be other sugars. Glycosides have therapeutic effects when the aglycone is released upon hydrolysis. The document further classifies and discusses the properties, extraction, uses and examples of various types of glycosides including saponins, liquorice roots, brahmi, dioscorea, ginseng, and sarsaparilla.
Lignans and flavonoids are plant compounds with potential health benefits. Lignans are dimers of phenylpropanoids found in flaxseed and other foods. When consumed, lignan precursors are converted by gut bacteria into enterolactone and enterodiol, which have weak estrogenic activity and other biological effects. Flavonoids are polyphenols that include subclasses like flavones, flavonols, flavanones, and anthocyanins found in fruits and vegetables. They are associated with reduced disease risk due to their antioxidant and anti-inflammatory properties. Both lignans and flavonoids are derived from phenylalanine through the shikimate pathway and undergo enzymatic conversions in their
Volatile oils, also known as essential oils, are aromatic oily liquids found in many plants. They are highly volatile and evaporate easily at room temperature. Volatile oils are composed of hydrocarbons and oxidized hydrocarbons derived from terpenes. They are found stored in secretory cells, cavities, or channels located in different parts of plants. Volatile oils have various therapeutic uses and are also used in perfumes, cosmetics, and flavorings due to their strong aromas. They are extracted from plants using various techniques including water and steam distillation, solvent extraction, and enfleurage.
Artemisia is a plant from the daisy family found in parts of Asia and the Middle East. It contains the compound artemisinin, which is used to treat malaria. Artemisinin and its derivatives are the most effective drugs currently available for treating drug-resistant malaria. The plant also contains other compounds like santonin which are used as anthelmintics to treat parasitic worm infections. Solvent extraction, especially using propylene glycol methyl ether, is commonly used to separate artemisinin from the Artemisia annua plant for medicinal use.
Alkaloidal amines ephedra, colchicum Pharmacognostic studyDivya Sree M S
ย
This document provides information on the alkaloidal plants Ephedra and Colchicum. It describes their biological sources, geographical sources, cultivation methods, macroscopic and microscopic features, main chemical constituents including Ephedrine in Ephedra and Colchicine in Colchicum, chemical tests to identify the constituents, and traditional uses including as a bronchodilator and to treat gout respectively.
Metabolic Pathways in Higher Plants and their DeterminationDr. Siddhi Upadhyay
ย
a) Brief study of basic metabolic pathways and formation of different secondary metabolites through these pathways- Shikimic acid pathway, Acetate pathways and Amino acid pathway.
b) Study of utilization of radioactive isotopes in the investigation of Biogenetic studies.
The document summarizes information about the plant Catharanthus roseus, commonly known as Vinca or Periwinkle. It is native to Madagascar but cultivated in other tropical and subtropical regions. The plant contains important anticancer alkaloids vinblastine and vincristine in its leaves and roots. Vinblastine is used to treat Hodgkin's disease while vincristine is used for childhood leukemia. The flowers may also be used as a gentle laxative or gargle.
Flavonoids classification, isolation and identificationMona Ismail
ย
Flavonoids are groups of polyphenolic compounds which are found in fruits, flowers, seeds & vegetable.
(named from the Latin word flavus meaning yellow, their colour in nature)
Tannins are one of the most widely occuring group of natural substances in different families of higher plants. They are of two types-
1. Hydrolysable
2. Condensed
The pterocarpus is an example of condensed tannins which are non-hydrolysable.
Glycosides are organic compounds found in plants and animals that contain a sugar moiety bonded to a non-sugar aglycon portion. They are classified based on the chemical nature of the aglycon, the nature of the sugar moiety, and the type of linkage between the glycon and aglycon. Glycosides are isolated using the Stas-Otto method involving successive extraction with alcohol and precipitation with lead acetate. Cardiac glycosides contain steroidal aglycons and are isolated from plants like Nerium oleander through alcoholic extraction, precipitation, and partitioning between organic solvents. Anthraquinone glycosides are isolated through successive extraction of the plant material with organic solvents and purification by column
Gentian is a plant whose dried rhizome and roots are used as a bitter tonic. It contains several bitter glycosides such as gentiopicrin, which has an intensely bitter taste and is used to stimulate digestion. Gentian grows in central and southern Europe and Asia, and its rhizomes are harvested in autumn after 2-5 years of growth. Microscopically, transverse sections of gentian rhizome show a porous wood surrounded by parenchyma cells containing oil globules and calcium oxalate needles. Gentian is used as a stomachic to treat indigestion and other gastrointestinal issues.
Extraction , Isolation and Structure Elucidation of DigoxinMohammad Khalid
ย
Introduction
Mechanism of Action
Pharmacokinetics
Indication
Administration
Contraindication and Precaution
Use cautiously in
Adverse Effects
Extraction and Isolation of Digoxin
CHEMICAL TESTS
Structure Elucidation
Isolation, Identification and Analysis of PhytoconstituentsDr. Siddhi Upadhyay
ย
1) The document discusses the isolation, extraction and identification of various phytoconstituents like terpenoids, glycosides, alkaloids and resins.
2) Extraction methods like solvent extraction, fractional crystallization and chromatography are described for menthol, citral, artemisin, glycyrrhetinic acid, rutin, atropine, quinine, reserpine, caffeine and podophyllotoxin.
3) Identification tests include chemical tests and thin layer chromatography. Rf values are provided for comparison with reference standards.
Liquorice is obtained from the dried roots and stolons of Glycyrrhiza glabra. It contains glycyrrhizin as the main active constituent, which is about 50 times sweeter than sucrose. Microscopic examination shows the presence of starch grains, crystal fibers, cork cells, and border pitted vessels. Liquorice has demulcent, expectorant and anti-inflammatory properties and is used to mask bitter tastes in medicines and for flavoring purposes.
This document discusses flavonoids, which are a class of plant secondary metabolites that are commonly known for their antioxidant properties. It describes the molecular structure of flavonoids and how they are biosynthesized in plants. The document outlines some of the main biological effects of flavonoids, including their anti-inflammatory, anti-microbial and anti-cancer activities. It also notes that flavonoids themselves have little direct antioxidant value in the human body, but their consumption may provide indirect benefits through induced Phase II enzymes and effects on uric acid levels. Several important flavonoids and dietary sources of flavonoids are highlighted.
This document discusses flavonoids, a class of polyphenolic compounds found in plants. It notes that over 4,000 flavonoids have been identified in foods and beverages, and that they have antioxidant and anti-inflammatory properties. Flavonoids are categorized into subclasses including flavonols, flavones, flavanones, and isoflavones. The document explores the antioxidant activities and health benefits of specific flavonoids like quercetin and xanthohumol. High intake of flavonoids from foods is associated with reduced risk of diseases like cancer and heart disease.
Pharmacognosy of Atropa belladona, biological source, geographical source, chemical constituents, uses, morphology of leaves, flower, fruits of belladona, deadly night shade leaves, chemical test, microscopy, T.S of leaves
This document discusses tropane alkaloids, specifically atropine alkaloid. It summarizes that atropine alkaloid is mainly found in plants from the solanaceae family, like Atropa belladona and Datura stromonium. It then describes the isolation, biosynthesis, identification tests, chemistry and properties, structure-activity relationships, uses, and mechanism of action of atropine alkaloid.
This document discusses glycosides, which are organic natural compounds found in many plants and some animals. Glycosides are composed of a sugar (glycone) and non-sugar (aglycone) moiety linked together by a glycosidic linkage. The sugar is often glucose but can also be other sugars. Glycosides have therapeutic effects when the aglycone is released upon hydrolysis. The document further classifies and discusses the properties, extraction, uses and examples of various types of glycosides including saponins, liquorice roots, brahmi, dioscorea, ginseng, and sarsaparilla.
Lignans and flavonoids are plant compounds with potential health benefits. Lignans are dimers of phenylpropanoids found in flaxseed and other foods. When consumed, lignan precursors are converted by gut bacteria into enterolactone and enterodiol, which have weak estrogenic activity and other biological effects. Flavonoids are polyphenols that include subclasses like flavones, flavonols, flavanones, and anthocyanins found in fruits and vegetables. They are associated with reduced disease risk due to their antioxidant and anti-inflammatory properties. Both lignans and flavonoids are derived from phenylalanine through the shikimate pathway and undergo enzymatic conversions in their
Volatile oils, also known as essential oils, are aromatic oily liquids found in many plants. They are highly volatile and evaporate easily at room temperature. Volatile oils are composed of hydrocarbons and oxidized hydrocarbons derived from terpenes. They are found stored in secretory cells, cavities, or channels located in different parts of plants. Volatile oils have various therapeutic uses and are also used in perfumes, cosmetics, and flavorings due to their strong aromas. They are extracted from plants using various techniques including water and steam distillation, solvent extraction, and enfleurage.
Artemisia is a plant from the daisy family found in parts of Asia and the Middle East. It contains the compound artemisinin, which is used to treat malaria. Artemisinin and its derivatives are the most effective drugs currently available for treating drug-resistant malaria. The plant also contains other compounds like santonin which are used as anthelmintics to treat parasitic worm infections. Solvent extraction, especially using propylene glycol methyl ether, is commonly used to separate artemisinin from the Artemisia annua plant for medicinal use.
Alkaloidal amines ephedra, colchicum Pharmacognostic studyDivya Sree M S
ย
This document provides information on the alkaloidal plants Ephedra and Colchicum. It describes their biological sources, geographical sources, cultivation methods, macroscopic and microscopic features, main chemical constituents including Ephedrine in Ephedra and Colchicine in Colchicum, chemical tests to identify the constituents, and traditional uses including as a bronchodilator and to treat gout respectively.
Metabolic Pathways in Higher Plants and their DeterminationDr. Siddhi Upadhyay
ย
a) Brief study of basic metabolic pathways and formation of different secondary metabolites through these pathways- Shikimic acid pathway, Acetate pathways and Amino acid pathway.
b) Study of utilization of radioactive isotopes in the investigation of Biogenetic studies.
The document summarizes information about the plant Catharanthus roseus, commonly known as Vinca or Periwinkle. It is native to Madagascar but cultivated in other tropical and subtropical regions. The plant contains important anticancer alkaloids vinblastine and vincristine in its leaves and roots. Vinblastine is used to treat Hodgkin's disease while vincristine is used for childhood leukemia. The flowers may also be used as a gentle laxative or gargle.
Flavonoids classification, isolation and identificationMona Ismail
ย
Flavonoids are groups of polyphenolic compounds which are found in fruits, flowers, seeds & vegetable.
(named from the Latin word flavus meaning yellow, their colour in nature)
Tannins are one of the most widely occuring group of natural substances in different families of higher plants. They are of two types-
1. Hydrolysable
2. Condensed
The pterocarpus is an example of condensed tannins which are non-hydrolysable.
Glycosides are organic compounds found in plants and animals that contain a sugar moiety bonded to a non-sugar aglycon portion. They are classified based on the chemical nature of the aglycon, the nature of the sugar moiety, and the type of linkage between the glycon and aglycon. Glycosides are isolated using the Stas-Otto method involving successive extraction with alcohol and precipitation with lead acetate. Cardiac glycosides contain steroidal aglycons and are isolated from plants like Nerium oleander through alcoholic extraction, precipitation, and partitioning between organic solvents. Anthraquinone glycosides are isolated through successive extraction of the plant material with organic solvents and purification by column
Gentian is a plant whose dried rhizome and roots are used as a bitter tonic. It contains several bitter glycosides such as gentiopicrin, which has an intensely bitter taste and is used to stimulate digestion. Gentian grows in central and southern Europe and Asia, and its rhizomes are harvested in autumn after 2-5 years of growth. Microscopically, transverse sections of gentian rhizome show a porous wood surrounded by parenchyma cells containing oil globules and calcium oxalate needles. Gentian is used as a stomachic to treat indigestion and other gastrointestinal issues.
Extraction , Isolation and Structure Elucidation of DigoxinMohammad Khalid
ย
Introduction
Mechanism of Action
Pharmacokinetics
Indication
Administration
Contraindication and Precaution
Use cautiously in
Adverse Effects
Extraction and Isolation of Digoxin
CHEMICAL TESTS
Structure Elucidation
Isolation, Identification and Analysis of PhytoconstituentsDr. Siddhi Upadhyay
ย
1) The document discusses the isolation, extraction and identification of various phytoconstituents like terpenoids, glycosides, alkaloids and resins.
2) Extraction methods like solvent extraction, fractional crystallization and chromatography are described for menthol, citral, artemisin, glycyrrhetinic acid, rutin, atropine, quinine, reserpine, caffeine and podophyllotoxin.
3) Identification tests include chemical tests and thin layer chromatography. Rf values are provided for comparison with reference standards.
Liquorice is obtained from the dried roots and stolons of Glycyrrhiza glabra. It contains glycyrrhizin as the main active constituent, which is about 50 times sweeter than sucrose. Microscopic examination shows the presence of starch grains, crystal fibers, cork cells, and border pitted vessels. Liquorice has demulcent, expectorant and anti-inflammatory properties and is used to mask bitter tastes in medicines and for flavoring purposes.
This document discusses flavonoids, which are a class of plant secondary metabolites that are commonly known for their antioxidant properties. It describes the molecular structure of flavonoids and how they are biosynthesized in plants. The document outlines some of the main biological effects of flavonoids, including their anti-inflammatory, anti-microbial and anti-cancer activities. It also notes that flavonoids themselves have little direct antioxidant value in the human body, but their consumption may provide indirect benefits through induced Phase II enzymes and effects on uric acid levels. Several important flavonoids and dietary sources of flavonoids are highlighted.
This document discusses flavonoids, a class of polyphenolic compounds found in plants. It notes that over 4,000 flavonoids have been identified in foods and beverages, and that they have antioxidant and anti-inflammatory properties. Flavonoids are categorized into subclasses including flavonols, flavones, flavanones, and isoflavones. The document explores the antioxidant activities and health benefits of specific flavonoids like quercetin and xanthohumol. High intake of flavonoids from foods is associated with reduced risk of diseases like cancer and heart disease.
Flavonoid adalah senyawa fenol yang banyak ditemukan di alam yang memberikan warna merah, ungu, dan kuning pada tumbuhan. Struktur dasar flavonoid terdiri atas 15 atom karbon yang membentuk susunan C6-C3-C6. Flavonoid memiliki berbagai jenis seperti flavon, flavonol, antosianidin yang dapat diisolasi dari ekstrak tumbuhan melalui fraksinasi.
Flavonoids are polyphenolic compounds found in plants that act as antioxidants. They have 15 carbon atoms arranged in two benzene rings connected by a 3 carbon chain. There are over 4,000 known flavonoids that are commonly found as flower pigments but also occur in other plant parts. Major classes of flavonoids include flavones, flavonols, flavanones, and isoflavonoids. Flavonoids have important biological functions like repairing damage, protecting plants from toxins and UV radiation, and possess anti-inflammatory, antiviral and antitumor properties in humans.
Flavonoids are plant secondary metabolites that are classified based on their chemical structure. They are abundant in many plant families and occur as both free compounds and glycosides. Key classes include flavonols, flavones, flavanones, isoflavones, and anthocyanidins. Flavonoids have a variety of biological effects and are found in several plants that are used medicinally such as orange peel, garcinia, soybean, liquorice, cranberry, and buckwheat.
Plant secondary metabolites such as terpenes, phenolic compounds, and nitrogen-containing compounds help defend plants against herbivores and pathogens. Cutin, waxes, and suberin form physical barriers on plant surfaces that reduce water loss and pathogen invasion. Within plants, terpenes include volatile compounds that repel insects, as well as non-volatile triterpenes and tetraterpenes that act as toxins. Phenolic compounds include soluble and insoluble polymers like lignin that provide structural support and act as deterrents. Flavonoids contribute to pigmentation, UV protection, and attracting pollinators. Secondary metabolites are an important part of both constitutive and induced plant defenses.
Saponin glycosides are found in parts of plants and are used as detergents. Examples include the root of Saponaria officinalis. There are two types of aglycones: steroidal and triterpenoidal. Glycyrrhiza contains glycyrrhizic acid which produces glycyrrhizic acid and two molecules of glucuronic acid upon hydrolysis. It is used as a flavoring agent and for its demulcent, expectorant, and liver-protective properties. Sarsaparilla's active ingredient is sarsaponin which produces sarsapogenin and D-glucose and L-rhamnose upon hydrolysis. It is
The document discusses guidelines for quality control and standardization of herbal medicines provided by the World Health Organization (WHO). It defines key terms like quality, safety, purity and potency. It outlines the need for quality control to reduce adulteration and ensure proper authentication, validation of claims, and safety. The WHO guidelines provide standardization procedures for herbal drugs, including definitions, authentication, absence of contaminants, microscopic and chromatographic analysis. It also discusses analytical procedures like botanical, physicochemical, biological and toxicological parameters for testing herbal medicines.
Two apples, Red Delicious and Granny Smith, are among the most popular varieties. Eating apples and apple juice may help reduce the risks of Alzheimer's, Parkinson's, and pancreatic cancer by providing antioxidants and fiber. Regular apple consumption is also linked to lower cholesterol and reduced risks of gallstones and constipation due to their high fiber content.
This document provides an introduction to plant chemotaxonomy and flavonoids. It discusses that flavonoids are polyphenolic compounds found in many plants that contain 15 carbon atoms arranged in a C6-C3-C6 structure. Flavonoids are mainly water soluble, absorb UV and visible light, and can be bound to sugars. They have various biological effects like anti-inflammatory and anti-cancer properties. The document gives examples of specific flavonoids like luteolin found in Equisetum arvense and apigenin found in Petroselinum crispum.
Dokumen tersebut membahas tentang glikosida, yaitu senyawa yang terdiri dari bagian glikon dan aglikon dimana pada saat dihidrolisis akan menghasilkan gula. Dokumen tersebut menjelaskan berbagai jenis glikosida seperti antrakuinon, saponin, cyanophor, flavonol beserta sumber dan fungsinya. [/ringkasan]
Effect of heat and drought stress in pigeonpea on the expression of resistanc...ICRISAT
ย
Global warming and climate change will trigger major changes in herbivore plant interactions and efficacy of crop protection technologies (Sharma, 2014). โข Chemical composition of plants will change in direct response to global warming and climate change, affecting plant damage and growth and development of insect pests. We studied the effect of heat and water stress on expression of resistance to pod borer, Helicoverpa armigera in pigeonpea.
Saponins are plant constituents that cause foaming in aqueous solutions. They are glycosides that can be toxic if injected in the bloodstream but are harmless when taken orally. There are two main types of saponins - pentacyclic triterpenoid and steroidal. Saponins are hydrolyzed into aglycones and sugars. Aglycones determine the saponin type. Many plants contain medicinally active saponins such as diosgenin from Dioscorea villosa wild yam. Saponins have expectorant, anti-inflammatory and immune-modulating properties and are used to treat various conditions.
The document discusses different types of tannins, their properties, classification, and examples. It describes three specific types of tannins - Hamamelis, Catechu, and Nutt gall - including their botanical origins, constituents, and uses. Tannins are polyphenolic compounds that occur in plants and can precipitate proteins. They are classified as hydrolysable, condensed, or complex based on their chemical structure and properties.
Isothiocyanate glycosides yield mustard oil upon hydrolysis and provide non-specific resistance to plants against infection. These agents act as vesicants, rubefacients, and irritants. Lactone glycosides and aldehyde glycosides are also found in plants and insects, yielding active principles like cantharidin, vanillin, and gentiopicrin upon hydrolysis. Miscellaneous glycosides contain complex mixtures that are used for their bitterness, insecticidal properties, and as precursors to steroidal drugs.
Adsorption chromatography is a type of chromatography where the mobile phase is adsorbed onto the surface of a stationary solid phase. Separation occurs due to differences in how strongly components compete for active sites on the adsorbent, based on electrostatic forces. Common adsorbents include silica gel and alumina. Thin layer chromatography is a technique where the mobile phase flows over a thin layer of adsorbent on a plate, separating components by differential migration.
Glycosides are compounds that yield reducing sugars upon hydrolysis. They can be classified based on their aglycone (non-sugar portion), sugar components, number of sugar units, physiological activity, and plant source. Common cardiac glycosides contain steroidal aglycones and deoxy sugars. They increase the force of heart contractions and are found in plants like Digitalis and Strophanthus. Glycosides are isolated from plants using solvent extraction and purified via crystallization. Their properties and identities can be confirmed through hydrolysis and chemical tests.
This document discusses treatments for congestive heart failure (CHF), focusing on digitalis glycosides and other positive inotropic agents. It provides details on:
- The mechanisms of action and molecular effects of digitalis glycosides, which increase cardiac contractility and output, lowering venous pressure and edema.
- Other positive inotropic drugs used in acute CHF like dobutamine and phosphodiesterase inhibitors.
- Drugs that reduce cardiac preload and edema like diuretics and angiotensin converting enzyme inhibitors, which lower blood pressure and sympathetic tone.
The document explains the benefits, side effects and clinical uses of various CHF drugs in detail through multiple sections and diagrams.
content
Flavonoids (importance, Physiological role and Therapeutic uses).
Flavonoids biosynthesis, General Properties and Tests for identity.
Flavone Glycosides (Diosmin and Apiin)
Flavonol Glycosides (rutin and Quercetrin)
Flavanone Glycosides (Hesperidin)
Silymarin (flavonolignans)
Isoflavonoids (Genistein)
Coumarin Glycosides
Flavonoids are plant secondary metabolites that contain a 15-carbon skeleton structure. They are classified into two main classes: anthocyanins and anthoxanthins. Hesperidin is a flavonoid glycoside found abundantly in citrus fruits. It consists of the aglycone hesperitin bound to the disaccharide rutinose. Hesperidin is isolated from citrus peels and can account for up to 14% of the fresh weight of immature oranges. It has various physiological functions and properties including acting as an antioxidant and strengthening capillary blood vessels.
Structural elucidation and isolation of glycoside, purine and flavanoidsSana Raza
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Unit three of chemistry of natural products, consist of the method of extraction, isolation and structure elucidation of Glycoside(digoxin), Flavanoids( quercetin), Lignans( Podophyllotoxin), Purines (caffeine)
The document discusses flavonoids, a large group of plant metabolites that include flavones, flavonols, flavanones, isoflavonoids, anthocyanidins, and flavan-3-ols. Flavonoids are found naturally in plants and have various functions like pigments, growth regulators, and antimicrobial properties. They also have therapeutic uses like antioxidant, anticancer, antiviral, and hepatoprotective effects. The document describes the isolation, identification, and properties of various flavonoid subclasses and compounds like hesperidin, rutin, catechins, and silymarin. It provides information on the source, structure, and pharmacological activities of important flavonoids.
These are an important class of naturally occurring drugs whose actions include both beneficial and toxic effects on the heart. Plant glycosides with specific action on the heart are known as cardiac glycosides. The main cardiac glycosides are cardenolides found in plants like foxglove and bufadienolides found in toad skin. They work by inhibiting the sodium-potassium ATPase pump in cardiac muscle cells, increasing calcium levels and strengthening heart contractions. Common uses of cardiac glycosides include treatment of congestive heart failure and cardiac arrhythmias.
This document discusses flavonoids, which are secondary plant metabolites that provide color and protect plants. It defines flavonoids and describes their biosynthesis, distribution in plants, properties, classification, and various health benefits. Specifically, it summarizes different types of flavonoids like flavonols, flavanones, isoflavonoids, and anthocyanins and their sources. It also outlines several medicinal properties of flavonoids including their antioxidant, anti-inflammatory, anti-cancer, anti-bacterial, anti-ulcer, anti-atherosclerotic, and hepatoprotective effects.
This document discusses flavonoids, which are polyphenolic compounds found in plants. It provides an introduction to flavonoids, including their structure, occurrence in plants, and functions. It also describes methods for isolating, extracting, and determining the structures of flavonoids, such as using chromatography, ultraviolet and infrared spectroscopy, and nuclear magnetic resonance spectroscopy. Key tests for detecting flavonoids include the Shinoda test and sodium hydroxide test.
The document provides an overview of flavonoids, a class of secondary plant metabolites. It discusses the composition, structures, subclasses and properties of flavonoids. Key points include: flavonoids are polyphenolic compounds found in many plants; they have antioxidant effects and play roles in plant growth and pollination; major subclasses include flavones, flavonols, flavanones and anthocyanidins; glycosylation and other substitutions lead to diversity in flavonoid structures. The document also reviews the structures and properties of related subclasses like lignans and isoflavones.
The document discusses reactive oxygen species (ROS) generated during aerobic metabolism in plant tissues. ROS induce oxidative damage under environmental stress. Proline acts as an antioxidant by scavenging ROS and protecting protein integrity via molecular chaperone activity. Gamma-aminobutyric acid (GABA) maintains redox homeostasis by regulating ratios of NADH/NAD+ and NADPH/NADP+ during stress. Both proline and GABA help plants withstand stress by mitigating ROS damage.
Cardiac glycosides and flavonoids are secondary metabolites found in plants. Their biosynthesis involves multi-step pathways. Cardiac glycosides are produced from cholesterol via the mevalonate pathway and coupling of aglycone and glycone moieties. Their biosynthesis begins with squalene and involves lanosterol, pregnenolone and other intermediates. Flavonoids originate from phenylalanine through the shikimate acid pathway and are synthesized via the phenylpropanoid pathway. This involves the formation of chalcones from 4-coumaroyl-CoA and their conversion to flavonoids through enzymatic ring closures and modifications.
PHYTOCHEMISTRY ASSIGNMENT FOR PHARMACOGNOSYGanugavade
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This document discusses the importance of alkaloids and glycosides found in herbal industries. It begins by classifying alkaloids based on their taxonomic, biosynthetic, pharmacological, and chemical properties. Common chemical tests used to detect alkaloids are described. Glycosides are then defined and classified based on their aglycone and sugar components. Several important medicinal plants containing alkaloids and glycosides are discussed, highlighting their anti-inflammatory, immune-supporting, antioxidant, and other therapeutic properties. In conclusion, alkaloids and glycosides provide significant medicinal benefits and are valuable components in herbal supplements and formulations.
This document reviews flavonoids, a group of polyphenolic compounds found in plants. Flavonoids have diverse chemical structures and characteristics. They are potent antioxidants and have been shown to protect against coronary heart disease. Dietary intake of flavonoids ranges from 23-170 mg per day depending on location. Major dietary sources include tea, onions, apples, and red wine. More research is still needed to fully understand flavonoid absorption, metabolism, mechanisms of action, and relationship to heart disease risk.
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This document provides an overview of prostaglandins, leukotrienes, and thromboxanes. It discusses their introduction, classification, chemical structures, biosynthesis, regulation, mechanisms of action, functions, and applications. Specifically, it notes that prostaglandins are derived from arachidonic acid and have diverse hormone-like effects. Leukotrienes are inflammatory mediators produced from arachidonic acid oxidation. They are involved in inflammation and hypersensitivity reactions. Thromboxanes are involved in blood clotting and are derived from arachidonic acid through the action of thromboxane-A-synthase.
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SYNOPSIS
INTRODUCTION
HISTORY
DEFINITION
PRIMARY VS SECONDARY PLANT METABOLISM
SECONDARY METABOLITES
PHENOLIC COMPOUND
PHENYLPROPANOID PATHWAY METABOLITES
PHENYLPROPANOID BIOSYNTHESIS
BIOCHEMICAL PATHWAYS TO PHENOLIC CLASSES
SOME IMPORTANT PRODUCTS OF PHENYLPROPANOID PATHWAY
LIGNANS AND LIGNINS
FLAVONOIDS
METABOLIC ENGINEERING OF PHENYLPROPANOID PRODUCTION
BIOTECHNOLOGICAL APPLICATIONS
CONCLUSION
REFERENCES
This document discusses various types of bioactive compounds found in plants. It defines bioactive compounds as those that have an effect on the organism consuming them. Examples of common bioactive compounds mentioned include caffeine, flavonoids, carotenoids, and others. The document also discusses different classes of bioactive compounds such as alkaloids, flavonoids, anthocyanins, saponins, tannins, glycosides, and terpenoids; and provides some examples of compounds that fall into each class. It notes that bioactive compounds can have various effects on organisms and some are known to interact with medications.
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This document provides an overview of prostaglandins, leukotrienes, and thromboxanes. It discusses their introduction, classification, chemical structures, biosynthesis, regulation, mechanisms of action, functions, and applications. Specifically, it notes that prostaglandins are derived from arachidonic acid and have diverse hormone-like effects. Leukotrienes are inflammatory mediators produced from arachidonic acid oxidation. They are involved in inflammation and hypersensitivity reactions. Thromboxanes are involved in blood clotting and are derived from arachidonic acid through a biosynthetic pathway involving thromboxane-A-synthase.
This document provides an introduction to plant constituents and their chemical tests. It discusses that plants contain primary and secondary metabolites. Primary metabolites include carbohydrates, proteins, lipids, and nucleic acids which are essential for plant life. Secondary metabolites have therapeutic effects and include alkaloids, glycosides, terpenoids, volatile oils, tannins, and resins. The document then focuses on carbohydrates, describing monosaccharides, disaccharides, and polysaccharides. It provides examples and discusses their structures and chemical properties. Tests to identify carbohydrates are also outlined.
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The presentation is meant for academic purpose only and includes the definition, occurrence & distribution, classification, properties, chemical tests, general isolation techniques and importance of glycosides.
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There are 4 phases of wound healing: hemostasis, inflammation, proliferation, and remodeling. This document also describes the mechanism of wound healing. Factors that affect healing include infection, uncontrolled diabetes, poor nutrition, age, anemia, the presence of foreign bodies, etc.
Complications of wound healing like infection, hyperpigmentation of scar, contractures, and keloid formation.
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(๐๐๐ ๐๐๐) (๐๐๐ฌ๐ฌ๐จ๐ง ๐)-๐๐ซ๐๐ฅ๐ข๐ฆ๐ฌ
๐๐ข๐ฌ๐๐ฎ๐ฌ๐ฌ ๐ญ๐ก๐ ๐๐๐ ๐๐ฎ๐ซ๐ซ๐ข๐๐ฎ๐ฅ๐ฎ๐ฆ ๐ข๐ง ๐ญ๐ก๐ ๐๐ก๐ข๐ฅ๐ข๐ฉ๐ฉ๐ข๐ง๐๐ฌ:
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๐๐ฑ๐ฉ๐ฅ๐๐ข๐ง ๐ญ๐ก๐ ๐๐๐ญ๐ฎ๐ซ๐ ๐๐ง๐ ๐๐๐จ๐ฉ๐ ๐จ๐ ๐๐ง ๐๐ง๐ญ๐ซ๐๐ฉ๐ซ๐๐ง๐๐ฎ๐ซ:
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3. Ramzi A. Mothana, PhD
What are Flavonoids??
3PHG322, Flavonoids, Feb 2013
4. Ramzi A. Mothana, PhD
Flavane-derivatives
Chemically, they are 2-phenylchroman derivatives.
Flavonoids are virtually universal plant pigments.
They are responsible for the color of flowers, fruits
and sometimes leaves.
They ensure tissue protection against the
damaging effects of UV radiation.
4PHG322, Flavonoids, Feb 2013
5. Ramzi A. Mothana, PhD
Classification
They fall into many classes depending on the degree of oxidation
of the central pyran ring:
1- Flavanones (4-Oxo-flavane) such as naringenin.
2- Flavones (4-Oxo-flav-2-ene) such as apigenin.
3- Flavonols (3-Hydroxy-4-Oxo-flav-2-ene) such as quercetin.
4- Flavanols (3-Hydroxyflavane, Catechine) such as (+)-catechine.
5- Flavandiols (3,4-Hydroxyflavane) Leukoanthocyanidine).
6- Flavylium-salts (Anthocyanidine) such as cyanidine.
5PHG322, Flavonoids, Feb 2013
6. Ramzi A. Mothana, PhD
HO
OH O
OH
O
Flavone
HO
OH O
OH
O
OH
Falvonol
O
OH
OOH
HO
2
3
Flavanone
HO
OH
OH
O
OH
Flavanol
(Catechine)
6PHG322, Flavonoids, Feb 2013
HO
OH O
OH
O
OH
Flavylium-salt
(Anthocyanidine)
X
HO
OH OH
OH
O
OH
Flavandiol
(Proanthocyanidine)
7. Ramzi A. Mothana, PhD
Distribution
Flavonoids are common in the plant kingdom, Bryophytes
(mosses and hepaticas), and in Pteridophytes.
No flavonoids have been found in algae.
More than 3000 of these compounds are now known, with
nearly 500 aglycones.
They are abundant in the Polygonaceae, Rutaceae,
Rosaceae, Leguminosae, Umbelliferae, Lamiaceae and
Compositae.
7PHG322, Flavonoids, Feb 2013
8. Ramzi A. Mothana, PhD
Chemical structure
Many authors apply the term flavonoids to flavon-, flavanon-,
and flavonol-derivatives.
They occur in free state and as glycosides, most are O-glycosides.
But a considerable number of flavonoid C-glycosides are known.
In all the classes of flavonoids mentioned so far, biosynthesis
frequently places at least 3 phenolic OH-groups in the 5-, 7-, and
4ยด-positions of the aglycone.
8PHG322, Flavonoids, Feb 2013
O
OH
OOH
HO
2
3
Flavanone
9. Ramzi A. Mothana, PhD
Flavones and Flavonols
The essential difference between flavones and flavonols is the
presence of OH-group at C-3 in the flavonols.
Flavones and flavonols) represent about 80 % of the flavonoids.
Ring A is substituted by two phenolic OH-groups at C-5 and C-7.
These OH-groups are either free or etherified.
OHO
OH O
OH
5
7 2
3
3ยด
4ยด
R
A C
B
Apigenin: R = H
Luteolin: R = OH
B
CA
R
4ยด
3ยด
3
27
5
OH
OOH
HO O
OH
Quercetin: R = OH
Kaemferol: R = H
Flavons Flavonols
9PHG322, Flavonoids, Feb 2013
10. Ramzi A. Mothana, PhD
Flavanones and Dihydroflavonols
These molecules are characterized by the absence of a 2,3-double
bond and by the presence of at least one asymmetric center.
Two isomeric forms of each flavanone structure are possible, thus
the B ring can be in the (2S)- or in (2R)-configuration.
DihydroflavonolsFlavanons
Taxifolin: OH OH
Pinobanksin: H H
OH
OHO
OH O
R2
5
7 2
3
3ยด
4ยด
R1
A C
B
Hesperitin: OH OCH 3
Naringenin: H OH
B
CA
R1
4ยด
3ยด
3
27
5
R2
OOH
HO O
H
HH
H
H
R1 R2 R1 R2
10PHG322, Flavonoids, Feb 2013
11. Ramzi A. Mothana, PhD
Biflavonoids
They are flavonoids, which bond to one another, particularly
through their very reactive C-6 or C-8.
The interflavanic linkage can be of:
Carbon-carbon-type (3ยด,8, e.g. in amentoflavone, or 6,8, e.g. in
agathisflavone, or 8,8, e.g. in cupressiflavone).
Carbon-oxygen-carbon-type (6-O-4ยด, e.g. in hinokiflavone).
Biflavonoids are characteristic of the Gymnosperms.
OR1O
OH O
OR2
5
7 2
3
4ยด
4ยด
3
27
5
OR4
OOH
R3O O
3ยด
R1=R2=R3=R4= H, Amentoflavone
R2=Me, R1=R3=R4= H, Bilobetin
R1=R2=Me, R3=R4= H, Ginkgetin
R2=R4=Me, R1=R3= H, Isoginkgetin
11PHG322, Flavonoids, Feb 2013
12. Ramzi A. Mothana, PhD
4ยด
7
5
OH
OOH
HO
4ยด
3
27
5
OH
OOH
HO O
O
Agathisflavone
HO
OH O
OH
4ยด
HO
OH O
OH
5
7
4ยด
O
O
Cupressuflavone
OHO
OH O
OH
5
7 2
3
4ยด
HO
OH O
O
5
7 2
3
4ยด
O
Hinokiflavone
12PHG322, Flavonoids, Feb 2013
13. Ramzi A. Mothana, PhD
Flavonoid glycosides
The sugar moiety may be a mono-, di-, or trisaccharide, linear or
branched.
Monosaccharides include D-glucose, D-glalctose or D-allose, L-
rhamnose, or D-glucuronic or D-galacturonic acid.
The glycosidic bond may be established through any of the phenolic
OH-group on the aglycone (O-glycosides).
C-glycosides are not rare, more than 300 are known.
The bond is established between the asymmetric carbon on the
sugar and the C-6 or C-8 of the aglycone.
13PHG322, Flavonoids, Feb 2013
14. Ramzi A. Mothana, PhD
Types of C-glycosides
Mono-C-glycosylflavonoids
Di-C-glycosylflavonoids
C-glycosyl-O-glycosylflavonoids
Acyl-C-glycosyl-flavonoids
R4
OH
OOH
R2O O
R3
R1
Vitexin H H Glu H
Isovitexin Glu H H H
Schaftoside Glu H Ara H
Vicenin 2 Glu H Glu H
R1 R2 R3 R4
14PHG322, Flavonoids, Feb 2013
15. Ramzi A. Mothana, PhD
Identification and Characterization
with 5% AlCl3 in methanol (yellow-green fluorescent spots in UV
light)
with 1 % solution of diphenylboric acid-2-aminoethyl ester
(Naturstoff Reagenz A) (red-brown color is formed).
with FeCl3, anisaldehyde-reagent phenols.
Pachecoยดs test for dihydroflavonols (with sodium acetate/acetic
anhydrid/HCl) (Red color).
Pewยดs test for dihydroflavonols (with Zinc/HCl)
a deep purple-red with dihydroflavonols and brownish color
Flavanones and other flavonoids.
Shinoda test for flavanones and dihydroflavonols (with Mg/HCl)
Deep-red or magenta color is produced.
15PHG322, Flavonoids, Feb 2013
16. Ramzi A. Mothana, PhD
Pharmacological and biological properties
They decrease capillary permeability and fragility
They are enzyme inhibitors such as lipooxygenase,
cyclooxygenase, histidine decarboxylase, hyaluronidase,
cAMP phosphodiesterase.
Many flavonoids are antioxidants, because they react with
free radicals.
Therefore, they show anti-inflammatory, antiallergic,
hepatoprotective and antispasmodic.
They can decrease blood cholestrol, be diuretic,
antibacterial and antiviral.
16PHG322, Flavonoids, Feb 2013
17. Ramzi A. Mothana, PhD
Therapeutic uses
Treatment of the symptoms of venous and
lymphatic vessel insufficiency (tiredness or
fullness in the legs, cramps, pains and other
dysfunctions, edemas)
Treatment of circulatory disturbances.
Treatment of capillary fragility disorders of the
skin (ecchymosis, petechiae) and of mucosas
(gingival hemorrhage, epistaxis).
Treatment of dysfunctions linked to the acute
attack of piles.
Metrorrhagias linked to intra-uterine
contraceptive devices.
17PHG322, Flavonoids, Feb 2013
18. Ramzi A. Mothana, PhD
Chief flavonoids on the Market
1- Rutin
It is a flavonol glycoside. Chemically, it is quercetin-3-O-(6-O-
rhamnoside) glucoside.
It occurs as yellow crystals, soluble in boiling water and alcohol.
Rutin alone or in combination with other substances is used as
described previously, particulaly to treat hemorrhages linked to
diabetes and hypertension, and to treat the functional symptoms
of the acute attack of piles.
18PHG322, Flavonoids, Feb 2013
O
OHO
OH O
OH
5
7 2
3
3ยด
4ยด
OH
Rutin
Glu Rham
19. Ramzi A. Mothana, PhD
Sources of rutin
Ruta graveolens (Fam. Rutaceae)
Buckwheat-species: Herb of Fagopyrum esculentum (Fam.
Polygonaceae) (up 5%) and of Fagopyrum tataricum (up to 3%).
Japanese pagoda tree (Sophora japonica, Fam. Fabaceae).
The flower buds of which contain 15-23 % Rutin.
19PHG322, Flavonoids, Feb 2013
Ruta graveolens Fagopyrum Sp.
20. Ramzi A. Mothana, PhD
2- Citroflavonoids (especially Hesperidin)
They are extracted from Pericarps and pulbs of
Citrus-trees as Ca and Mg derivatives.
Hesperidin is hesperitin-7-O-(6-O-rhamnoside)
glucoside, it occurs up to 8 % in the pericarp.
Uses:
in the treatment of the leg symptoms of
chronic, functional and organic venous
insufficiency,
and as adjuvant or prophylactic with vitamin C
for the treatment of common cold and
infections.
OH
4ยด
3ยด
3
27
5
OCH3
OOH
O O
Glu
Rham
Hesperidin
20PHG322, Flavonoids, Feb 2013
21. Ramzi A. Mothana, PhD
3- Diosmin
It is a flavone glycoside found in
Buchu leaves (Barosma sp.)
It occurs in pale yellow needles or
powder.
Acid hydrolysis of diosmin yields
diosmetin (aglycone) besides one
molecule of rhamnose and glucose.
Uses:
diuretic and diaphoretic effect
also in the treatment of venous
disorders.
Diosmin
Rham
Glu
OO
OH O
OCH3
5
7
OH
21PHG322, Flavonoids, Feb 2013
Barosma betulina
22. Ramzi A. Mothana, PhD
Flavonoid containing drugs
1- Whitethorn herb
The drug consists of the herb and sometimes of
the fruits of Crataegus monogyna, C. laevigata
and of C. pentagyna (Fam. Rosaceae)
The drug contains:
2 % flavonoids (0.7 % as hyperoside), other chief
constituents are vitexin, rutoside, apigenin- and
luteolin-derivatives.
Up to 1 % oilgomeric procyanidines (4,8- or 4,6
dimeric, trimeric to hexameric flavan-3-ols).
It is used in the treatment of cardiac insufficiency
(grad I-II to NYHA), in treatment of brady
arrhythmia and to improve the circulation of the
coronary artery.
22PHG322, Flavonoids, Feb 2013
C. monogyna
23. Ramzi A. Mothana, PhD
2- Maidenhair tree
Leaves of Ginkgo biloba (Fam. Ginkgoaceae)
found in China and Japan, but also cultivated
in Europe.
The drug contains:
1- 0.4-2 % biflavonoids (amentoflavone,
bilobetin, and ginkgtin)
2- 0.5-2 % flavonol glycosides. (quercetin and
kaempferol-derivatives)
3- 4-12 % flavan-3-ols and proanthocyanidins
4- 0.02-0.2 % ginkgolides (comlexes of
diterpenlactones)
23PHG322, Flavonoids, Feb 2013
24. Ramzi A. Mothana, PhD 24PHG322, Flavonoids, Feb 2013
Uses:
In the treatment of the symptoms of senile
cerebral insufficiency (vertigo, tinnitus and
hearing loss, lack of concentration).
In the treatment of the intermittent
claudication and of Raynaudยดs disease.
26. Ramzi A. Mothana, PhD
3- Passion flower
The drug consists of the herb of Passiflora incarnata (Fam.
Passifloraceae), found in south and North America (USA and Mexico).
The drug contains:
up to 2.5 % flavonoids (C-glycosylflavonoids) such as Vitexin,
isovetexin, schaftoside and vicenin-2.
Uses:
as sedative to treat the symptoms of nervousness in adults and
children and particularly minor sleeplessness.
also used to treat abnormities of the cardiac rhythm in the adult.
26PHG322, Flavonoids, Feb 2013
R4
OH
OOH
R2O O
R3
R1
Vitexin H H Glu H
Isovitexin Glu H H H
Schaftoside Glu H Ara H
Vicenin 2 Glu H Glu H
R1 R2 R3 R4
28. Ramzi A. Mothana, PhD
4- Birch leaf
The drug consists of the leaves of Betula
pendula or Betula pubenscens (Fam.
Betulaceae), which is found in Europe
and in China.
The drug contains:
3 % flavonoids, paticularly
Hyperoside and quercitrin
used as diuretic (in the bacteriuria),
particularly in the urinary tract
infections such as pyelonephritis,
ureteritis, cystitis and urethritis.
28PHG322, Flavonoids, Feb 2013
29. Ramzi A. Mothana, PhD
5- Lime tree flowers or Linden flowers
The drug consists of the flowers of Tilia
cordata or Tilia platyphyllos (Fam.
Tiliaceae), which is found in Europe and
in Asia (China).
The drug contains 1% flavonoids, specially
glycosides of quercetine such as rutin,
hyperoside and quercitrine and glycosides
of kaemferol such as tiliroside.
The drug is used as expectorant for the
treatment of cough and as diaphoretic
(common cold and fever).
29PHG322, Flavonoids, Feb 2013
Tilia cordata
31. Ramzi A. Mothana, PhD
Catechines
They are flavan-3-ol derivatives.
They are the mother substances of condensed tannins.
The representative substances of this group are the diastereomeric
pairs (+)-catechine and (-)-epicatechine as well as (+)-gallocatechine
and (-)-epigallocatechine (2R: 3S or 2R: 3R).
OH
H
R
4ยด
3ยด
3
27
5
OH
OH
HO O
H
OH
H
R
4ยด
3ยด
3
27
5
OH
OH
HO O
H
OH OH
(+)-Catechine (R = H)
(+)-Gallocatechine (R = OH)
(-)-Epicatechine (R = H)
(-)-Epigallocatechine (R = OH)
31PHG322, Flavonoids, Feb 2013
32. Ramzi A. Mothana, PhD
Chemical test:
1- with FeCl3, it gives green color.
2- on heating with acids, it forms phloroglucinol (lignin-test)
Uses:
โข Immunostimulant.
โข Adjuvant in the treatment of infections with chemotherapy,
also in the treatment of liver-diseases especially hepatitis.
Sources:
1- Gambir (extract of Uricaria gambir) 20-50%.
2- Black Catechu (extract of Acacia Catechu) 4-12%.
32PHG322, Flavonoids, Feb 2013
33. Ramzi A. Mothana, PhD
Isoflavonoids
โข Isoflavonoids are distinct from other flavonoid classes in that they
contain a rearranged C15 skeleton based on 3-phenylchroman.
โข They are about 700 known structures.
Distribution:
โข Isoflavonoids are very limited in the plant kingdom, they occur in the
Leguminosae.
OH
O
33PHG322, Flavonoids, Feb 2013
34. Ramzi A. Mothana, PhD
Isoflavonoides may be classified into a dozen structural types
according to their oxidation level and variation in the complexity
of the skeleton (by the existence of added heterocycles):
1- Isoflavones
โข They form the largest group (with 234 known structure).
โข They occur in the free state or more rarely as glycosides.
โข e.g. daidzein, formononetin and genistein.
O
7
OOR1
HO
OR2
Daidzein: H H
Formononetin: H CH3
Genistein: OH H
R1 R2
34PHG322, Flavonoids, Feb 2013
Classification
35. Ramzi A. Mothana, PhD
2- Isoflavanones, isoflavenes and isoflavanes
- are much rarer than isoflavones.
OH
O
O
O
OH
O
OH
3- Rotenoids
๏ฎ Rotenoids are a chromanochromanones.
๏ฎ They are insecticidal. (representative of the group is rotenone.)
O
O
1
2
4
5
6
6 a
8
9
11
12 12 a
Rotenoid skeleton
9
O
OO
O
OCH3
OCH3
Rotenone
O
35PHG322, Flavonoids, Feb 2013
36. Ramzi A. Mothana, PhD
4- The pterocarpans
They are the second largest class of isoflavonoids after the
isoflavones.
They all have a tetracyclic ring system.
5- The Coumestans
They represent the highest possible level of oxidation for the
isoflavonoid skeleton.
Coumestrol is the best-known member of this group.
11
9
8
6 a
6
5
4
2
O
O
1
10
7
11 a
O
OHO
OCH3
Pterocarpan skeleton Medicarpin
36PHG322, Flavonoids, Feb 2013
CoumestrolCoumestan skeleton
OH
HO O
O
11 a
7
10
1
O
O
2
4
5
6
6 a
8
9
11
O O
37. Ramzi A. Mothana, PhD
Isoflavonoids show three important activities, these are:
1- Oestrogenic activities (simple isoflavones and coumestans)
2- Antibacterial properties (the isoflavonoid phytoalexins)
3- Insecticidal properties (rotenoids)
Pharmacological and biological properties
37PHG322, Flavonoids, Feb 2013