Cell Content PDF

25/10/2023 Cell contents Living contents Non- living contents Metabolism products Protoplasm Nucleus...

25/10/2023 Cell contents Living contents Non- living contents Metabolism products Protoplasm Nucleus Mitochondria Ribosome plastids The cell contents are those which can be identified by microscopical examination or by chemical tests. 44 Cell contents Non- living contents Living contents (metabolism products) Secondary products Reserve food materials [By- products of metabolism] [ primary products] Active constituents (metabolites) Non- active constituents (By- products) Carbohydrates (starch, sugar) Alkaloids, Glycosides Protein (aleuron grains) Vol.oils, anthraquinones Ca. oxalates, Lipids (fats , fixed oil) Tannins, saponins, Ca.co3, ca.so4 organic acids Ca. tartarate. 45  25/10/2023 Cell contents Non- living contents (metabolism products) Reserve food materials [ primary products] Carbohydrates (starch, sugar) Protein (aleuron grains) Lipids (fats , fixed oil) 46 Carbohydrates: Carbohydrates are organic compounds composed of carbon, huydrogen and oxygen, where the later two are present of the ratio 2:1 like that of their presence in water. These include starch, inulin, sucrose. 47  25/10/2023 1- Starch  Starch is a polysaccharides of high molecular weight, with the general formula (C6H10O5)n and is one of the most widely distributed cell contents in plants  It is formed as a result of the photosynthesis process which is carried out by the green parts of the plant. 6CO2 + 6H2O C6H12O6 + 6O2  The formed glucose molecules are condensed together to give starch nC6H12O6 (C6H10O5)n + nH2O It occurs in granules in varying size in almost all organs of plants either alone or accompanied with other reserve food particles. 48 Kinds of starch 1- Assimilatory: it is found as small granules in the chloroplasts of the green parts. It is temporary, being hydrolyzed during darkness. 2- Transitory: It is deposited in the medullary rays, xylem, phloem and pith in the form of small granules which are used up by the growing organs. 3- Reserve: It is present in storage organs as large size granules. This kind constitutes all starches used for economic and medicinal purposes. 49  25/10/2023 Chemical composition of starch granules: Starch consists of two components which differ in physical properties. 1- Amylose the inner layers of the granules More water soluble and less viscous in solution. It is responsible for the blue colour with iodine. Consist of 200-300 glucose (1, 4 linkage), and can be hydrolyzed by β- amylase into maltose. 50 2- Amylopectin the outer layers of the granules Less water soluble and more viscous. Gives bluish red or violet colour with iodine solution. Consists of 1000 glucose unites, most of which are connected with 1, 4 linkage. In addition to 1,6 linkage. Only 60% hydrolyzed by β- amylase into maltose. And the rest residue named dextrin which is 1,6 linkage 51  25/10/2023 Properties of starch: 1- It is practically insoluble in cold water, but on boiling with water, it forms a white colloidal solution which forms jelly on cooling. 2- On heating when dry at 150 °C – 160 °C it is converted to dextrin which is soluble in water. 3- It is stained blue with iodine, this colour disappear on heating and reappear on cooling. 4- It does not reduce Fehling’s solution, but on heating with dilute acids it is hydrolyzed giving glucose, which reduce Fehling’s solution. 5- Acid hydrolysis of starch gives glucose. 6-The enzyme β- amylase degrades starch to give maltose Maltose consists of two glucose units with α-1,4 linkage. 52 53  25/10/2023 Microscopical characters Shape: oval, polyhedral or round Hilum: It is the first part laid down in leucoplast, and around which the body of granule is deposited It is appears as a point or radiating It is in the centre (centric), or apart from centre (eccentric) 54 Microscopical characters Aggregation: 1- Simple: when the granule showing single hilum 2- Compound: when the granule is produced by deposition of layers around two or more hilum. 3- Semicompound: produced by deposition of layers forming a common layer of starch. Striation: Different layers of starch in the same granule forming alternate rings Concenteric, around the hilum Transverse, not around Distincit, faint, invisible, abscent. 55  25/10/2023 1- Potato starch Starch consists of the polysaccharide granules obtained from the tubers of Solanum tubersum, Family: Solanaceae Simple or few compound 2- 3 component, irregullary ovoid or subsphericlal granules Hilum is distinct eccentric point and striations are distinct 56 2- Maize starch Starch consists of the polysaccharide granules obtained from the endosperm of Zea mays, Family: Graminae Hilum is centric triangular Simple polyhedral or stellate cleft and subsphericlal granules striations are absent 57  25/10/2023 3- Wheat starch Starch consists of the Polysaccharide granules obtained from the endosperm of Triticum vulgare, Family: Graminae Small granules are rounded or oval rarely polygonal Large granules are lenticular, hilum is faint Mixture of small and large granules centric and striation are faint concentric with a few of intermediate size, they are mostly simple rarely compound 58 4- Rice starch Starch consists of the Polysaccharide granules obtained from the endosperm of Orayaza sativa, Family: Graminae Simple and compound granules. Simple granules are polyhedral with pointed angle Hilum is occasionally seen as centric and striations are absent 59  25/10/2023 Potato starch Wheat starch Maize starch Rice starch 60 Uses of starch 1. Starch suspension is used as antidote for iodine poisoning. 2. Used externally to prevent itching. 3. Used as disintegrant in tablet, when the tablet reaches stomach, the starch absorbs water and the medication release. 4. Used in paper and cloth manufacturing 5. Nutrient 6. In cosmetic 7. Used as emollient and as a base for suppositories. 8. Starting material for many products as Liquid glucose, dextrose, maltose, dextrin, soluble starch, insoluble starch, butanol, acetone and ethanol 61  25/10/2023 2- GUMS & MUCILAGE They are polysaccharide complexes formed from sugar and uronic acid units, these complexes are combined with metals. Gums are considered to be pathological products mucilage is formed by normal metabolism. 62 Gums: Formation Gums are abnormal products, formed by - Injury of the plant - Unfavourable conditions (e.g. drought; ‫)جفاف‬ - By a breakdown of cell walls (A process of extracellular formation called gummosis). Uses of gums 1.Suspending, emulsifying agents and adhesive. 2.In cosmetics, emollient. 3.In toothpastes and hand lotions. 4.As a masking agent for acrid tasting substances. 63  25/10/2023 Mucilage Mucilages are generally normal products of metabolism formed within the cell (intracellular formation). Function of Mucilages - Storage material - Water storage reservoir - Protection for germinating seeds. Mucilage is often found in - Epidermal leaf cells - Seed coats - Roots 64 Characters: 1. Solution of Ruthenium red (R.R) stains the mucilage of Senna and Buchu leaves with red color. 2. Solution of Corallin-soda stains the mucilage of Squill with red color. 3. They are stained blue with Methylene blue. 65  25/10/2023 Cell contents Non- living contents (metabolism products) Reserve food materials [ primary products] Carbohydrates (starch, sugar) Protein (aleuron grains) Lipids (fats , fixed oil) 66 Reserved food materials Proteins Proteins are nitrogenous organic substances  give on hydrolysis polypeptides, dipeptides then amino acids.  Storage protein occurs in the form of amorphous masses or small particles called aleurone grains, seen in the oily seeds.  The aleurone grain consists of a mass of protein surrounded by a thin membrane, the ground mass of protein encloses one or more rounded bodies or globoid and an angular body known as crystalloid. 67  25/10/2023 Chemical test 1. Red colour with Millon,s reagent. 2. Yellow colour with picric acid. 3. Blue-violet colour with NaOH 20% and CuSO4 solution. 68 Reserved food materials Fixed oils, fats and waxes They are reserved food materials occurring in various parts of plants and animals. They are mixture of fatty acid with glycerine CH2OCOR CH2OH H2O CHOCOR 3 RCOOH + CHOH Fatty acids CH2OH CH2OCOR Fatts and fixed oils Glycerol 69  25/10/2023 They are greasy, non-volatile Insoluble in water, soluble in ether and chloroform Leave permanent stain on paper. Hydrolyzed by alkali giving soap (sod salt of fatty acid) and glycerine saponification 70 What is saponification process? Hydrolysis of fats by boiling with alkali is a saponification process. Waxes: They are esters of fatty acids but in this case combined with higher monohydric alcohols such as ceryl or palmetic alcohol. Waxes hydrolyzed with KOH giving higher alcohols 71  25/10/2023 Uses Some oils are used in treatment of skin diseases Some oils are laxatives Some oils are used as emollient Some oil as cod liver oil used in rickets and T.B Some waxes are used as bases for ointments Some fats promote absorption of drugs through skin. 72 Cell contents Non- living contents (metabolism products) Secondary products Reserve food materials [By- products of metabolism] [ primary products] Non- active constituents (By- products) Carbohydrates (starch, sugar) Protein (aleuron grains) Ca. oxalates, Lipids (fats , fixed oil) Ca.co3, ca.so4 Ca. tartarate. 73  25/10/2023 Non-living cell contents: end products (non- active constituents) Calcium oxalates It is an organic waste product which produces characteristic crystalline forms. Formed in the plant cell as an end product of metabolism. They formed as a result of reaction between Ca++ salts + oxalic acid (absorbed from soil) (from metabolic products) 74 Different forms of ca.ox.: They occur in drugs with different forms. The form in particular drug is constant and so afford valuable diagnostic value for this drug A- Solitary or single (of common occurrence). 1- Scattered prisms e.g. hyoscyamus 2- Twinned crystals e.g. hyoscyamus 75  25/10/2023 3- - Styloid e.g. in quillaia. (columnar elongatted prism). 4- Acicular or needle shape crystals: needle-shaped crystals very narrow and pointed at the two ends found scattered in the cell sap and not in bundles e.g. cinnamon But Bundle of acicular crystals embedded in mucilage e.g squill. Named Raphides 76 B- Aggregated crystals 1- Raphides of acicular crystals 2- Cluster crystals: aggregated crystals (prisms) radiating irregularly from a central point. e.g. Datura strammonium. 3- Rosette crystals: formed of aggregated crystals (prisms) radiating from one central point but in one plane. e.g. Umbelliferae 77  25/10/2023 4- Microcrystals or crystal-sand: (Idioblastes): These are very minute crystals occurring together in large number being either: Micro-prismatic as in Cinchona Microsphenoidal as in Belladonna. 5- Sphero-crystals or Spherities: rare occurrence, formed of needle-shaped crystals radiating from common centre as in fungi 78 The arrangements of crystals of calcium oxalates in the plant tissues is sometimes of diagnostic value Crystal layer in Datura Crystal sheath in Senna Also, absence of calcium oxalates in plant tissue give a valuable aid in identification of drugs as Boldo, Digitalis, Rosmary, Mentha, Lavander and Saffron 79  25/10/2023 Calcium carbonate Calcium carbonate are embedded in the cell wall and called cystoliths (e.g. cannabis). It can be identified by its solubility with acetic acid with effervescence. 80 How could you differentiate between calcium oxalates and other crystalline substances? 1. Ca.ox. soluble in HCL without effervescent. (c.f. calcium carbonate). 2. Ca.ox. decomposes with 20% H2SO4 and forms needles of calcium sulphates. 3. Ca.ox. Do not react with barium chloride solution (c.f. calcium sulphate). 4. Very slowly affected by solution of caustic alkalis the crystals disappear within few weeks (other calcium salts dissolve rapidly). 81  25/10/2023 1- When the plant grows naturally without taking care of it by man ; it is known as ……………………….. 2- ……………… is a kind of starch, present in storage organs as large size granules. This kind constitutes all starches used for economic and medicinal purposes. 3- Mucilage is considered to be pathological products. 4- 1st part in plant name is Genius. It must begin with capital letter. 5- The enzyme β- amylase degrades starch to give glucose 82 1- When the plant grows naturally without taking care of it by man ; it is known as wild plant. 2- Reserve is a kind of starch, present in storage organs as large size granules. This kind constitutes all starches used for economic and medicinal purposes. 3- Mucilage is considered to be pathological products.× Gum is considered to be pathological products Mucilage is considered to be pathological products.× Mucilage is considered to be normal metabolism 4- 1st part in plant name is Genius. It must begin with capital letter. (true) 5- The enzyme β- amylase degrades starch to give glucose× The enzyme β- amylase degrades starch to give maltose The enzyme β- amylase degrades starch to give glucose× Dilute acid degrades starch to give glucose 83  25/10/2023 Cell contents Non- living contents Living contents (metabolism products) Secondary products Reserve food materials [By- products of metabolism] [ primary products] Active constituents (metabolites) Non- active constituents (By- products) Carbohydrates (starch, sugar) Alkaloids, Glycosides Protein (aleuron grains) Vol.oils, anthraquinones Ca. oxalates, Lipids (fats , fixed oil) Tannins, saponins, Ca.co3, ca.so4 organic acids Ca. tartarate. 84 Active constituents These are chemical compounds synthesized by the living cells and possesses physiological activity. 1. Volatile oils 2. Resins 3. Balsams 4. Bitter principles 5. Tannins 6. Alkaloids 7. Glycosides 8. Enzymes 9. Vitamins 85  25/10/2023 1-Volatile oil: General properties ♣-They are known as etherial or essential oils. ♣-They are volatile with steam and don’t leave any permanent oily stain on the filter paper. ♣-All volatile oils have characteristic aromatic odour. ♣-They can be prepared by steam distillation 86 ♣-The families rich in V.O are Labiatae, Rutaceae, Umbelliferae , Lauraceae and Compositae. ♣-They are secreted in: oil cells ex. Cinnamon secretion ducts ex. Fennel glandular hairs ex. Mentha, Chammomile. Glands ex. Buchu ♣-V.O are not saponified by alkalies. 87  25/10/2023 Roles of V.O in plants 1. Eliminate certain abnormal metabolic products and thus may be detoxification products. 2. Attract the insects, thus aid in pollination of the flower. 3. Act as repellents to insects (defense agent). 4. Serve as solvent for wound healing resins. Frequently they associated with substance as resins (Oleoresin) or gums (Oleo gum resin). 88 Uses of Volatile oils 1. Carminative: 2. Diuretic: 3. Mild antiseptic: 4. Anthelmintic: 5. Parasiticid: 6. Used in perfumery. 7. Used as flavoring agent 89  25/10/2023 Chemical tests 1. Suddan III reagent-------- red colour 2. Alkanna Tr.--------- red colour. 3. Osmic acid -------- brown colour. 4. On spotting on filter paper -------- no permanent stain 90 Composition of Volatile Oils  Volatile oils are generally mixtures of hydrocarbons and oxygenated compounds derived from these hydrocarbons.  The unit of them is isoprene unit.  Almost any type of organic compound may be found in volatile oils (hydrocarbons, alcohols, ketones, aldehydes, ethers, oxides, esters, and others). “usually volatile oils are classified according to the type of organic compounds”. CH3 CH2 H2 C C CH CH2 CH3 C CH CH CH C CH CH 2 2 2 Head CH3 Tail Monoterpene Isoprene unit Myrcene 91  25/10/2023 Difference between Volatile and Fixed Oils Items Volatile oil Fixed oil mixtures of hydrocarbons mixture of ester of fatty nature and oxygenated compounds acids with glycerol derived from these hydrocarbons condition Volatile Non volatile separation Steam distillation expression occurrence Secretory structures Endosperm and embryo Stain on paper Give No stain Give stain saponification Not saponified saponified alcohol soluble Sparingly soluble 92 2-Resins ‫مواد صمغيه‬ Resins are solid or semisolid organic compounds of complex chemical nature but free from nitrogen. Resins on heating soften and finally melts. They are water insoluble but soluble in alcohols , fixed and volatile oils. They are heavier than water. 93  25/10/2023 Resins are prepared from pants by incision or by extraction with alcohol, then precipitation with water. Resins are often associated with: ◊- volatile oil oleo- resin ◊- gums gum - resins. ◊- oil + gum oleo – gum – resins. ◊- sugars glucoresin 94 3-Balsams: Balsams are resinous mixtures that contain balsamic acids (benzoic acid or cinnamic acid) or esters of these acids. Balsams have aromatic odour Example: balsam tolu, balsam peru 95  25/10/2023 4-Bitter Principals: Bitter Principals are compounds composed of carbon, hydrogen and oxygen and free from nitrogen. They have bitter taste Found in families: Compositae, Labiatae. 96 5-Tannins: They are soluble in alcohol, acetone & alkali. They are soluble in water forming colloidal solutions having astringent taste. They are precipitated from aqueous solutions by lead acetate. 97  25/10/2023 Uses of Tannins 1. They are used as antidote in alkaloid or heavy metal poisoning, they form precipitates with many alkaloids. 2. Used as reagent for detection of proteins, gelatin and alkaloids (precipitation). 3. Used in tanning process Tannins combine with protein in animal hides, prevent putrefaction and convert them into leather. 4. Used in treatment of burns and GIT disorders because they are astringent. 98 When tannins are applied to the non-living tissue the process is know as tanning process. When tannins are applied to the living tissue the process is know as astringant. Used in treatment of burns. Tannins combine with protein and form insoluble compound, the skin becomes less permeable to water and less susceptible to putrefaction and swelling 99  25/10/2023 Tannins can be classified into 2 main groups according to phenolic compounds enter in constitution of tannins Pyrogallol tannins Catechol tannins Hydolysable or Condensed or Phlobatannins Non-Phlobatannins Structure Have glucose esterified by phenolic Formed of condensation of 3 molecules acids (gallic acid) of flavonoids, have no sugars Hydrolysis with acid Hydrolyzed Not hydrolyzed Effect of heat Give pyrogallol Give catechol Bromine water no ppt yellow or brown ppt Ferric chloride blue black colour green colour 100 101  25/10/2023 Questions 1- Starch does not reduce Fehling’s solution, but on heating with dilute acids it is hydrolyzed giving Maltose, which reduce Fehling’s solution. 2- When tannins are applied to the living tissue the process is known as tanning process 3- Fixed oil attract the insects, thus aid in pollination of the flower 4- Starch is used as antidote in alkaloid or heavy metal poisoning 5- Official drug is listed and described in a book by governments as the legal authority for standards (Pharmacopoeia). 102 1- Starch does not reduce Fehling’s solution, but on heating with dilute acids it is hydrolyzed giving Maltose, which reduce Fehling’s solution. 2- When tannins are applied to the living tissue the process is known as tanning process 3- Fixed oil attract the insects, thus aid in pollination of the flower 4- Starch is used as antidote in alkaloid or heavy metal poisoning 5- Official drug is listed and described in a book by governments as the legal authority for standards (Pharmacopoeia). 103  25/10/2023 6- Alkaloids Definition: Alkaloids are basic nitrogenous compounds found in plants and possess marked physiological activity but some of them are highly toxic. Most alkaloids are crystalline substances and contain the elements C, H, O and N in their molecules ; but few are liquids and oxygen free as nicotine and coniine. 104 Nomenclature: names should end by "ine". These names may refer to: 1. The genus of the plant, such as Atropine from Atropa belladona. 2. The plant species, such as Belladonnine from Atropa belladona. 3. The common name of the drug, such as Ergotamine from ergot. 4. The name of the discoverer, such as Pelletierine that was discovered by Pelletier. 5. The physiological action, such as Emetine that acts as emetic. 6. A prominent physical character, such as Hygrine that is hygroscopic. 105  25/10/2023 Classification: True (Typical) alkaloids that are derived from amino acids and have nitrogen in a heterocyclic ring. e.g Atropine Protoalkaloids (Atypical) that are derived from amino acids and do not have nitrogen in a heterocyclic ring, but in side chain. e.g Ephedrine Pseudo alkaloids that are not derived from amino acids but have nitrogen in a heterocyclic ring. e.g Caffeine False alkaloids are non alkaloids give false positive reaction with alkaloidal reagents. 106 Basic nucleus of alkaloids 107  25/10/2023 Function in Plants Dicots are more rich in alkaloids than Monocots. Families rich in Alkaloids: Apocynaceae, Rubiaceae, Solanaceae and Papaveracea. Families free from Alkaloids: Rosaceae, Labiatae 1. They may act as protective against insects due to their bitterness and toxicity. 2. Source of nitrogen in case of nitrogen deficiency. 3. They, sometimes, act as growth regulators in certain metabolic systems. 4. They may be utilized as a source of energy in case of deficiency in carbon dioxide assimilation. 108 General physical properties: 1. Alkaloids are usually colourless, odourless, crystalline, non- volatile and bitter in taste. 2. Only few are coloured e.g. berberine and colchicine are yellow in colour. 3. Few are liquids and odourous ( oxygen free) as nicotine and coniine. 4.. Some alkaloids contain phenolic group or carboxylic group, they are amphoteric forming salt with acids and alkali. ex morphine 109  25/10/2023 Tests for alkaloids: A- Alkaloidal preciptants: Most alkaloids are precipitated by: 1- Mayer’s reagent ---------- immediate white ppt. 2- Wagner’s reagent ---------- chocolate brown ppt. 3- Dragenddorf’s reagent ---------- orange red N.B.: other plant constituents as proteins give ppt. with many of the above reagents; so all alkaloidal tests should be done after extraction of alkaloids from the plant using organic solvents. 110 B- Alkaloidal colour reagents: These are some reagents give specific colour with some alkaloids 1- Froehd’s Reagent: 2- Marqui’s Reagent: 3- Mandalin’s Reagent: 4- Erdmann’s Reagent: 111  25/10/2023 Examples of some important alkaloids of common uses Atropine & Pilocarpine Physostigmine Hyoscyamine (Eserine) Source Hyoscyamus Pilocarpus Phyostigma muticus, F. jaborandi, F. venenosum, F. Solanaceae Rutaceae Leguminosae Nucleus Tropane Imidazole Indole N NCH3 OH N N H 112 Atropine & Pilocarpine Physostigmine Hyoscyamine (Eserine) Uses 1. Relaxation of bronchial Reduce the intra- Used in muscles, relief bronchial occular pressure of ophthalmic asthma. the eyes in case of preparation to 2. Relaxation of internal glucoma produce miosis, smooth muscles, anagonist the antispasmodic. 3. Dilatation of eye pupils, mydriatic action mydriatic. of atropine 4. Decease salivary and sweet glands secretions. Note: Contraindicated in Glucoma 113  25/10/2023 114 7- Glycosides Glycosides are non-reducing substances, consist of a sugar part bound to a different structure called the aglycone or genin. Classifications according to the Glycosidic Linkages between sugar and aglycone The sugar moiety can be joined to the aglycone in various ways: 1. Oxygen (O-glycoside) 2. Sulphur (S-glycoside) 3. Nitrogen (N-glycoside) 4. Carbon (Cglycoside) 115  25/10/2023 O-Glycosides can easily be cleaved into sugar and aglycone by hydrolysis with acids or enzymes. Almost all plants that contain glycosides also contain enzymes that bring about their hydrolysis (glycosidases). Glycosides are usually soluble in water, whereas aglycones are normally insoluble or only slightly soluble in water. 116 Hydrolysis of glycosides Glycosides do not reduce Fehling solution except after hydrolysis. 1- Acid hydrolysis The linkage between sugar and aglycone is hydrolysis in acid medium. The linkage is more split than the linkage between the individual sugars of the saccharide part of the glycoside. Note: C-glycoside is strongly resistant to normal acid hydrolysis. In aloin, the sugar is joined to aglycone with a direct C-C linkage 117  25/10/2023 2- Alkali hydrolysis Certain glycosides are modified or brocken down to the aglycone or sugar part by alkali. The lactone ring in cardiac glycosides is opened by strong alkali and loss activity. 3- Enzyme hydrolysis The glycoside is easily hydrolyzed by an enzyme which occurs in the same plant, in different cells. Example. Myrosin & emulsin 118 Pharmacological activity The physiological action of glycosides is due to aglycone. The role of sugar is stabilization and solubilization. The sugar is necessary to carry the aglycone to site of action where the pharmacological action is intended. 119  25/10/2023 Types of glycosides Classifications according to the Glycosidic Linkages between sugar and aglycone Classifications according to pharmacological action (Cardiac glycosides, Renal disinfectants, Anti- inflammatory glycosides. Laxative glycosides) Classification based on chemical nature of aglycone: 1- Phenolic glycosides: A-Simple Phenolic glycosides B- Anthracene glycoside C- Flavonoid glycoside D- Coumarin glycoside 2- Saponins 3- Cyanophore glycosides 4- Thioglycosides 5- Cardiac glycosides 120 1- Phenolic glycosides: A-Simple Phenolic glycosides They have aglycone containing phenolic groups together with either alcoholic group or carboxylic acid group. e.g arbutin and salicin Test: 1- with ferric chloride gives blue colour. 121  25/10/2023 Uses 1- antiseptic activity 2- diuretic activity (caution need to replenish potassium) 3- Arbutin, is effective in the topical treatment of hyperpigmentations. Melanin production was inhibited significantly by arbutin. 122 1- Phenolic glycosides: B-Anthracene glycosides  The aglycones are anthracenes derivatives and having laxative action.  These anthracene glycosides are sometimes referred to as the anthraquinone glycosides or the anthraglycosides.  The anthracene derivatives occur in vegetable drugs in different forms at different oxidation levels; like anthraquinones, anthrones, anthranols, oxanthrones or dimeric form (dianthrone). 123  25/10/2023 OH Anthranol (enol form) Taut. O O 8 1 7 9 2 4H A B C 6 10 3 5 4 Anthrone (keto form) O Anthraquinone 2 H 2H O O H OH Oxanthrone O Dianthrone 124 Chemical test Test for free anthraquinone Add KOH to the powder extract, rose-pink colour is formed Test for combined anthraquinone Borntrager's test 1- Boil powdered drug with 10% H2SO4 for 2 minutes to hydrolyze the glycoside 2- Filter while hot, cool, extract with benzene 3- To the benzene layer add half of its volume ammonia, shake well and allow separating, the amonnical layer will take a rose-pink colour Note: this test will be negative if there is very stable anthraquinone glycoside or reduced form of anthranol type Microsublimation test gives needles or droplets of anthrquinones, which gives a red colour with alkali. 125  25/10/2023 Uses Stimulant laxative Increase intestinal motility by direct local irritation of the mucosa. Anthraquinones are more active when they reduced by intestinal flora to anthranols Notes Site of action is colon Should not be given more than 7 days. Prolonged use cause habit formation, pigmentation of epithelial cells in colon, increase incidence of cancer. 126 Side effects Electrolyte imbalance Loss of body fluids Weight loss. Abdominal pain and cramps,( mentha should taken) Containdications Pregnancy and lactation Appendix and colon inflammation Heart disease, because it decease potassium level (hypokalemia) and so decease tone of heart muscle. 127  25/10/2023 Types of glycosides Classification based on chemical nature of aglycone: 1- Phenolic glycosides: A-Simple Phenolic glycosides B- Anthracene glycoside C- Flavonoid glycoside D- Coumarin glycoside 2- Saponins 3- Cyanophore glycosides 4- Thioglycosides 5- Cardiac glycosides 128 1- Phenolic glycosides: C-Flavonoid glycosides These are the largest group of phenolic glycosides. They present both in free state and as glycosides. This group is described as a series of C6-C3-C6. The flavones are yellow (Flavus = yellow). The intensity of yellow colour increase with number of hydroxyl groups. 129  25/10/2023 Therapeutic uses of flavonoids 1. Diuretic. 2. Antispasmodic. 3. Diaphoretic. 4. Increase strength of capillary walls, decrease capillary fragility.. 5. Decrease bleeding tendency in scurvy (deficiency of vit C. 6. Antioxidant 7. These compounds have high importance in nature as colour attractants to insects and birds as an aid to plant pollination. 130 Test 1. With aluminum chloride give yellow colour. 2. With KOH give yellow colour. 3. Alcoholic solution of flavonoids when treated with magnesium metal and HCl give an orange, red or violet colour (shinoda test) 131  25/10/2023 Examples of flavonoides Diosmin It is diuretic and urinary tract antiseptic. Diosmin is used for various disorders of blood vessels including hemorrhoids, poor circulation in the legs ,and bleeding (hemorrhage) in the eye or gums. Silymarin Occur in fruits of Silybum Used as antihepatotoxic 132 1- Phenolic glycosides: D-Coumarin glycosides They are derivatives of benzo-pyrone Some coumarins are phytoalexins and are synthesized by the plant following infection by a bacterium or fungus. Phytoalexins: any of a group of compounds formed in plants in response to fungal infection, physical damage, chemical injury, or a pathogenic process. Phytoalexins inhibit or destroy the invading agent. 133  25/10/2023 Uses 1. As flavouring agent and in perfumary. 2. Insecticidal 3. Antitumors. 134 Examples of coumarins scopoletin Antimicrobial, it is synthesized by the potato (Solanum tuberosum) following fungal infection. Khellin Natural product from Ammi Visnaga and has activity in: Kidney stones (khellin relaxes smooth muscle of ureters and ease the passage of renal calculi) Asthma ( vasodilator and relieve attacks of angina pectoris) 135  25/10/2023 Psoralen and Bergapten. Natural product from Ammi majus These compounds may be produced by the plant as a protection mechanism against high doses of sunlight. They are formulated into sunscreens and cosmetics for this purpose. It is used externally for treatment of (Vitiligo) (leukoderma), stimulates pigment production in skin exposed to UV light. 136 Chemical test There is no specific test for coumarin , but each compound is tested separately. A rose red colour is produced when the powder of Ammi visnaga is treated with solid KOH. The alcoholic extract of A. majus gives a blue fluorescence in Ultraviolet light. 137  25/10/2023 Types of glycosides Classification based on chemical nature of aglycone: 1- Phenolic glycosides: A-Simple Phenolic glycosides B- Anthracene glycoside C- Flavonoid glycoside D- Coumarin glycoside 2- Saponins 3- Cyanophore glycosides 4- Thioglycosides 5- Cardiac glycosides 138 2- Saponins They are group of glycosides(Latin Sapo, means Soap) The aglycones of the saponins are referred to as Sapogenins. General characters: 1. They foam in aqueous solution, persistent foam. 2. They cause haemolysis of red blood cells. 3. have sternutatory odour, and cause irr itation to mucous membrane of eyes and nose. 4. Have emulsifying properties so can be used as detergents. 139  25/10/2023 Saponins have the ability to cause haemolysis of red blood cells and to destroy them. When injected into the blood stream, they are highly toxic especially to cold- blooded animals e.g. frogs. Many are used as fish- poisons. When taken by mouth, Saponins are comparatively harmless, being not absorbed from the intestinal tract. The actual cause of the haemolysis: The red blood cells carry sterols in their membranes, and when brought into contact with saponins, the sterols of the RBCs are precipitated , this will lead to disturbance of the walls ending with rupture of R.B.Cs and this may cause 140 Structure of Saponins: According to the structure of the aglycone or sapogenin, two kinds of saponin are recognized: 1. The steroidal type (commonly tetracyclic C-27). 2. The pentacyclic type, ( C-30). Both of these have a glycosidal linkage at C-3. Steroidal saponins are of great pharmaceutical importance because of their relationship to compounds such as the sex hormones, cortisone, and vitamin D. 141  25/10/2023 142 Chemical test 1. On shaking the powdered drug containing saponins vigorously with water, a persistant froth is obtained. 2. On adding their solution to blood, haemolysis occurs, 143  25/10/2023 Uses of saponins 1. Expectorant 2. Steroidal saponins are used as precursors for synthesis of testesterone and cortisone. 3. Treatment of addison disease. 4. Used to increase viscosity and secretion of gastric mucousa. 144 Example of saponin Ginseng Uses of ginseng 1. Activate the synthesis of proteins 2. Stimulate the synthesis of bone marrow. 3. Normalize the blood pressure and blood sugar level. 4. Protect liver cells. 5. Increase physical and mental performance. 6. antifatigue 145  25/10/2023 Types of glycosides Classification based on chemical nature of aglycone: 1- Phenolic glycosides: A-Simple Phenolic glycosides B- Anthracene glycoside C- Flavonoid glycoside D- Coumarin glycoside 2- Saponins 3- Cyanophore glycosides 4- Thioglycosides 5- Cardiac glycosides 146 3- Cyanophore glycosides They named also Cyanogenetic glycosides (Cyanide glycosides). These compounds, in presence of enzymes such as - glucosidase, lose their sugar portion to form a cyanohydrin which, in the presence of water, can undergo hydrolysis to give benzaldehyde and the highly toxic hydrogen cyanide (HCN). 147  25/10/2023 148 Uses Cyanophore glycosides do not have wide range of applications, because of poisonous properties of hydrocyanic acid, which is evolved through enzymatic hydrolysis. They can be used as sedatives and in cough syrups 149  25/10/2023 Chemical tests Guignard reaction Freshly crushed linseed boiled in w.b with water for 30 min at 37 C, at top of tube put paper wetted with sodium picrate (yellow) _____HCN will formed and the paper turned red (sod picramate) 150 Examples: 1. Amygdalin in bitter almonds 2. Linamarin in linseed 151  25/10/2023 4- Thioglycosides They named also thiocyanate or sulfurated glycosides. They contain sulfur. Chemical Test: on paper chromatography, spray with silver nitrate, dry, respray with potassium dichromate, the glycosides appear as yellow spots against a red back ground of silver dichromate 152 Example of Thioglycosides Sinigrin In presence of water, the enzyme myrosin will hydrolyse it producing glucose, potassium acid sulphat and Allylisothiocyanate which is Pungent taste, pungent odour volatile liquid No odour, when soaked with water strong pungent odour evolved War gas is Allylisothiocyanate Irritation of the eye, lacrimation, irritation of respiratory system, increase secretion of mucous membrane, asphyxia and finally death. 153  25/10/2023 5- Cardioactive glycosides (Cardiac) Cardiac glycosides are a group of natural products characterized by their specific effect on myocardial contraction. In large doses they are toxic and bring about cardiac arrest, but in lower doses they are important drugs in the treatment of congestive heart failure. They have a diuretic activity. Since, the improved circulation tends to improve renal secretion, which relieves the edema often associated with heart failure. 154 Chemical Structure of glycosides Sugar- aglycone- lactone ring 155  25/10/2023 Lactone ring On the basis of the lactone ring structure, the aglucone in cardiac glycosides are devided into two main groups: 1- Cardenolide have unsaturated 5-membered lactone ringattached to C17. ex. Digitalis & Strophanthus. 2- Bufadienolide have unsaturated 6-membered lactone ring attached to C17. ex. Squill. 156 The existence of the unsaturated lactone rings play the largest role in the cardioactivity. The attachment with the receptor and hence the action of cardiac glycosides is achieved through a hydrogen bonding between the receptor and the lactone ring. If the lactone ring is saturated , the activity is reduced to 1|10 to 1|20 of the original, while opening of the ring will abolishes the activity. (remember alkaline hydrolysis 157  25/10/2023 Squill glycosides bufadienolides White variety: Proscillaridin A, scillaren A Red variety: scilliroside and glucoscilliroside; proscillaridin A and scillaren A as in the white variety 158 Pharmacological properties of squill White squill: Cardiotonic (proscillaridin A), and diuretic properties. it is an expectorant, but it also possesses emetic Red squill: it is used as a rat poison (scilliroside), because rodents lack the vomiting reflex, which makes red squill particularly lethal to these animals. 159  25/10/2023 Digitalis glycosides Cardenolide Digitalis purpurea and Digitalis lanata. 1. Digitalis purpurea (Red foxglove leaves) Purpurea glycosides A and B 1ry glycoside ) ,digitoxin and gitoxin (2ry glycoside) 2. Digitalis lanata (White foxglove leaves) Lanatosides A, B, C and D 160 Chemical test Keller-Kiliani test: Extract the powder with chloroform. Evaporate to dryness. Dissolve the residue in glacial acetic acid containing traces of FeCl3. Transfer to test tube, add conc. H2SO4 on the wall. An intense blue colour develop at the surface between the two layers. 161  25/10/2023 Active constituents These are chemical compounds synthesized by the living cells and possesses physiological activity. 1. Volatile oils 2. Resins 3. Balsams 4. Bitter principles 5. Tannins 6. Alkaloids 7. Glycosides 8. Enzymes 9. Vitamins 162 8- Enzymes They are high molecular weight proteins, they are organic biocatalyst produced by living cells. The action may be 1- specific : ex. Invertase enzyme which hydrolyses sucrose into glucose and fructose. 2- general : ex. Emulsin which hydrolyses most glycosides. Enzymes are inactivated by heat. 163  25/10/2023 9- Vitamins They are organic substances necessary to the normal growth and maintenance of life. Some are oil soluble A,D,E,K Some are water soluble C, B-complex 164