Phytotherapy and Chem. of Natural Products Lectures PDF

PHYTOTHERAPY AND CHEM.OF NATURAL PRODUTS DR. KHALED TAWAHA General Introduction Phytotherapy and chem. of natural products Dr. Khaled Tawaha Phytotherapy  The branch of herbal medicine that describes the potentials and limitation of herbal drugs in the trea...

PHYTOTHERAPY AND CHEM.OF NATURAL PRODUTS DR. KHALED TAWAHA General Introduction Phytotherapy and chem. of natural products Dr. Khaled Tawaha Phytotherapy  The branch of herbal medicine that describes the potentials and limitation of herbal drugs in the treatment of human diseases and should be prescribed by physicians trained in herbalism.  Herbal Drugs: ( Phyto-pharmaceuticals=Herbal medicines)  They are products containing exclusively plant material(comminuted or powdered vegetable drugs) or vegetable preparations( extracts,tinctures,fatty or essential oils,expressed plant juices,etc…) used for treatment of diseases (usually chronic) or to maintain a condition of improved health.  They don,t include difined isolated constituents or their mixtures  -Natural products are organic and inorganic compounds that are found in various natural sources-animal, plant,mineral and microbes.  - Natural products can be entire organism like as plant,animal or micor-organism.  -As a part of an organism( leaves, or flowers of plant,isolated animalorgan.  An extract of an organism or exudates or pur compounds( alkaloids, coumarines, flavonoids, saponins, steroids,and terpenoids)  -In practice, the term Natural Products refers to secondary metabolites small molecules produced by an organism  -Alkaloids such as morphine and antibiotics such as erythromycin and penicillin are good example of secondary metabolites  BIOSYNTHETIC PATHWAYS: 1-ACETATE PATHWAY 2-SHIKIMATE PATHWAY 3-MEVALONATE PATHWAY 4-NUCLEIC ACID PATHWAY  Metabolic pathways in higher plants and their determination. The living plant may be considered as a biosynthetic laboratory not only for primary metabolites like sugars, Amino acids and fatty acids and also for a multitude of secondary products of pharmaceutical significance such as glycosides, alkaloids, flavonoids, volatile oils etc. WHAT IS PHARMACOGNOSY?  Pharmacognosy, which literally‫ ﺣﺮﻓﯿﺎ‬means a knowledge of drugs or pharmaceuticals, has been part of the healing arts and sciences since mankind first began to treat illnesses.  During the past few years, as a result of the intense concern with all aspects of ecology, there has been a renewed interest in so-called `natural` foods and drugs. The availability of an extremely wide variety of these products, ranging from fenugreek tea to ginseng chewing gum, has stimulated‫ ﺣﻔﺰ‬the public to learn more about them. * The pharmacognosy was introduced by C.A.Seydler, a medical student in Halle/Saale, Germany, in 1815 (A small work by Seydler entitled Analecta Pharmacognostica) * This name is formed from two Greek words, pharmakon, drug!, and gnosis, knowledge.  Phytotherapy and chem. of natural products Dr. Khaled Tawaha * Pharmacognosy may be defined as `an applied science that deals with the biologic, biochemical, and economic features of natural drugs and their constituents.` It is a study of drugs that originate in the plant and animal kingdoms. Modern aspects of the science include not only the crude drugs but also their natural derivatives. 1-Digitalis leaf (Digitalis lanata folium) and its isolated glycoside, digitoxin, 2-Rauwolfia root (Rauwolfia serpintina radix) and its purified alkaloid, reserpine, 3-Thyroid gland with its extracted hormone, thyroxin, are all part of the subject matter of pharmacognosy. *Natural and Synthetic Substances : Distinguished by chemical and physical tests. In some instances ‫ ﺣﺎﻻت‬drug constituents have been partially replaced in commerce by synthetic compounds of identical chemical structure and therapeutic properties; Phytotherapy and chem. of natural products Dr. Khaled Tawaha 1-For example, natural camphor is obtained from the camphor tree by steam distillation; it is dextrorotatory in its reaction to polarized light(polarimeter). In contrast, synthetic camphor may be manufactured by either of two methods: by total synthesis from vinyl chloride and cyclopentadiene (a completely synthetic process) or by semi synthesis from pinene derived from pine sumps (not entirely a synthetic process but a chemical modification of a natural product). Synthetic camphor is racemic and can be differentiated easily from the natural form. 2- Epinephrine, caffeine, codeine, ephedrine, menthol, penicillin, and other chemicals may also be partial or total synthesis. They are considered a definite part of pharmacognosy. Phytotherapy and chem. of natural products Dr. Khaled Tawaha CRUDE DRUGS Phytotherapy and chem. of natural products Dr. Khaled Tawaha The term crude, as used in relation to natural products, means any product that has not been advanced in value or improved in condition by shredding, grinding, chipping, crushing, distilling, evaporating, extracting, artificial mixing with other substances or by any other process or treatment beyond what is essential to its proper packing and to the prevention of decay or deterioration pending manufacture. Crude drugs are vegetable or animal drugs that consist of natural substances that have undergone only the processes of collection and drying. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  * Crude Drugs or Extractives (Derivatives) are Used as Therapeutic Agents *Chief principles (constituents): extractives (or derivatives) which are obtained from the crude drugs (usually by extraction). Regardless of whether the derivative or extractive is a single substance or a mixture of substances, it is considered the chief constituent of the drug. * The process of drug extraction is a generally accepted method of obtaining these active principles. Extraction removes only those substances that can be dissolved in the liquid mixture referred to as the solvent, or, more specifically, as the menstruum. The undissolved portion of the drug that remains after the extraction process is completed is called the marc Phytotherapy and chem. of natural products Dr. Khaled Tawaha Important Definitions and Aspects Related to Crude Drugs The geographic source and habitat are the region in which the plant or animal yielding the drug grows. 1-Drugs are collected in all parts of the world, though the tropics and subtropics, where plant species, abound, yield more drugs than do the artic ‫ﻗﻄﺒﻲ‬and subarctic regions. 2-The Mediterranean basin, including Asia Minor, yields more drugs than any other region of the world. 3-However, India, the East Indies, central Europe, northern South America, Mexico, Central America, North America, and other regions yield numerous and valuable drugs. *Neither the scientific name of the plant nor the commercial name of the drugs is necessarily an indication of the true habitat of drugs plants. For example , the specific name of Acacia senegal seems to indicate that this plant, which yield gum Arabic, is most abundant in Senegal. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  Plants can be Indigenous‫ اﺻﯿﻞ‬and Naturalized‫ﻣﺘﺠﻨﺲ‬ Wild and Cultivated Plants Phytotherapy and chem. of natural products Dr. Khaled Tawaha  Indigenous and Naturalized 1-Plants growing in their native countries are said to be indigenous to those regions, such as Pinus palustris in the southern United States. 2-Plants are said to be naturalized when they grow in a foreign land a locality other than their native homes, such as Datura stramonium, which was introduced into the United States from Europe (native country). Reasons for naturalized plants A-Some of these plants may have been introduced with the seeds of cultivated plants. B-Some by birds or ocean currents ‫ﺗﯿﺎرات‬. C-Others by ballast of ships, and so on. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  Wild and Cultivated Plants * Drugs can be collected from wild plants, or plants can be cultivated for the production of drugs. * Cultivated medicinal plants have been propagated for centuries in China, India, Europe, and many other lands. *Plants usually cultivated in their non- native countries for economic and therapeutic (drug)interests. →For example cacoa (native to Mexico) is cultivated in large quantities in Nigeria, Ghana and Indonesia Phytotherapy and chem. of natural products Dr. Khaled Tawaha  *But in many instances plants have been cultivated in their native habitats, either 1-Because of dwindling natural supply or 2-To improve the quality of the drug ???.. It is important to ascertain ‫اﻟﺘﺎﻛﺪ‬that plants cultivated in a certain geographic area will develop the desired type and amount of constituents. The differences in the relative amounts of volatile constituents often determine the character of the oil and, consequently, the demand ‫اﻟﻄﻠﺐ‬for that particular oil. California orange oil is marketed at more than twice the price of Florid oils. * The use of modern isolation techniques and pharmacological testing procedures means that new plant drugs usually find their way into medicine as purified substances rather than in the form of galenical preparations. →dried Catharanthus roseus(Vinca rosea) →isolated alkaloids vinblastine and vincristine. Phytotherapy and chem. of natural products Dr. Khaled Tawaha *When specific plants, including those used in traditional medicine, suddenly become of interest to the world at large, the local wild sources soon become exhausted. This necessitates, as in the case of Catharanthus roseus, Arnica montana and Taxus brevifolia,research into the cultivation or artificial propagation by cell culture, etc.,.of such species. →In order to avert the type of supply crisis that arose at the clinical trial stage with the anticancer drug taxol, isolated from T. brevifolia, the US National Cancer Institute has initiated plans for future action when a similar situation again arises. *At the 91 Congress of the Italian Society of Phytotherapy and chem. of natural products (1998) it was stated that the current return of phytotherapy was clearly reflects by the increased market of such products. In 1995 the latter, for Europe, reached a figure of $6 billion, with consumption for Germany $2.5 billion, France $1.6 billion and Italy 600 million. I the US, where the use of herbal products has never been as strong as in continental Europe, the increase in recent years →1998 approaching $700 million. Phytotherapy and chem. of natural products Dr. Khaled Tawaha *Undoubtedly, the plant kingdom still holds many species of plant containing substances of medicinal value which have yet to be discovered; →large numbers of plants arc constantly being screened for their possible pharmacological value (particularly for their anti-inflammatory, hypertensive, hypoglycemic, amoebicidal, antifertility, cytotoxic antibiotic and anti- Parkinsonism properties). Phytotherapy and chem. of natural products Dr. Khaled Tawaha THE SCOPE AND PRACTICE OF PHYTOTHERAPY AND CHEM. OF NATURAL PRODUCTS 1-Although Phytotherapy and chem. of natural products is principally concerned with plant materials, → there are a small number of animal products which are traditionally encompassed within the subject →such items as beeswax, gelatin, wool fat, vitamins, etc. 2-Materials having no pharmacological action which are of interest to pharmacognosists are natural fibers, flavoring and suspending agents, colorants and stabilizers. 3- Other areas that have natural associations with the subject are poisonous and hallucinogenic plants, herbicides, insecticides. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  Chemical or Biogenetic Pharmacological Alphabetical or Therapeutic Vegetable drugs study Morphological Taxonomic Phytotherapy and chem. of natural products Dr. Khaled Tawaha 1. Alphabetical. Either Latin or vernacular names may be used. →This arrangement is employed for dictionaries, pharmacopoeias, etc. →Although suitable for quick reference it gives no indication of interrelationships between drugs. 2. Taxonomic. On the basis of an accepted system of botanical classification , the drugs are arranged according to the plants from which they are obtained in classes, orders, families, genera and species. → It allows for a precise and ordered arrangement. →As the basic botanical knowledge of pharmacy students decreases over the years →this system is becoming less popular for teaching purposes. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 3. Morphological. The drugs are divided into groups such as the following: A →leaves, flowers, fruits, seeds, herbs and entire organisms, woods, barks, rhizomes and roots (known as organized drugs), B → dried latices, extracts, gums, resins, oils, fats and waxes (unorganized drugs). →These groupings have some advantages for the practical study of crude drugs; the identification of powdered drugs →(Lab. Of Pharmacognosy) 4. Pharmacological or Therapeutic. This classification involves the grouping of drugs according to the pharmacological action of their most important constituent or their therapeutic use (cardiac glycosides, see table) →However, it is important to appreciate that the constituent of any one drug may fall into different pharmacological groups Phytotherapy and chem. of natural products Dr. Khaled Tawaha 5. Chemical or Biogenetic. The important constituents, e.g. alkaloids, glycosides, volatile oils, saponins etc., or their biosynthetic pathways, form the basis of classification of the drugs. → This is a popular approach when the teaching of Phytotherapy and chem. of natural products is phytochemically based. → Textbook : Bruneton j, Pharmacognosy, photochemistry and medicinal plants Phytotherapy and chem. of natural products Dr. Khaled Tawaha VOLATILE OILS(THYMLO,CARVACROL), GLYCOSIDRES(HEDEROSIDE) ALKALOIDS (MORPHINE), ANTHRAQUINONE GLYCOSIDES RESEARCH AND PUBLISHED MONOGRAPHS ON MEDICINAL HERBS →The aim has been to set ‫وﺿﻊ‬standards for quality‫ﺟﻮدة‬, efficacy‫ﻓﻌﺎﻟﯿﺔ‬ and safety‫ اﻟﺴﻼﻣﺔ‬in order that the many traditional herbs meet legal requirements‫ﻣﺘﻄﻠﺒﺎت اﻟﻘﺎﻧﻮﻧﯿﺔ‬. The following are of note‫ ﺟﺪﻳﺮ ﺑﺎﻟﻤﻼﺣﻄﺔ‬: 1-German Commission E monographs. These were developed for the German Federal Health Authority between 1978-1994 and involve 324 herbs used in German traditional medicine. →The monographs give sources, constituents and considerable pharmacological and clinical information. →They have now been translated into English and published by the American Botanical Council in 1999 as a single work. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 2- ESCOP monographs. ESCOP (European Scientific Cooperative for Phytotherapy) Information is given on approved therapeutic uses ‫ﻳﺘﻢ‬ ‫ﺗﻘﺪﻳﻢ اﻟﻤﻌﻠﻮﻣﺎت ﻋﻦ اﻻﺳﺘﺨﺪاﻣﺎت اﻟﻌﻼﺟﯿﺔ اﻟﻤﻌﺘﻤﺪة‬, and unlike the Commission E monographs, provides references. 3-AHP monographs. The American Herbal Pharmacopoeia planned to have published 11-13 monographs by the end of 2000. →There is naturally a selection‫ ﻣﺨﺘﺎرة‬of American traditional herbs with some overlap‫ ﺗﺪاﺧﻞ‬with the European monographs. 4- WHO monographs. The World Health Organization published Volume I of its Monographs on Selected Medicinal Plants in 1999. It contains standards‫ ﻣﻌﺎﻳﯿﺮ‬for quality of drugs together with a therapeutic section. 5- USPmonographs. The United States Pharmacopoeia is also producing herbal monographs. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  Current awareness. -Students wishing to read original research will find many references in this book and should learn how to find similar ones for themselves. As no one can hope to read all the scientific literature that is published, special journals are devoted to the publication of brief abstracts from the original papers. Such abstracts give the author's name, the subject of the research, the reference necessary to locate the paper in the original journal and usually a brief outline of the work it contains. Most pharmacy department libraries contain Chemical Abstracts and Biological Abstracts. Some journals for example, Planta Medica, Journal of Ethno pharmacology, Phytochemistry and Journal of Natural Products-periodically contain reviews on some aspect of medicinal plants. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  BOTANICAL NOMENCLATURE The modern rules governing‫ ﺗﺤﻜﻢ‬the terminology of plant taxonomy are laid down in The International Code of Botanical Nomenclature. * Botanical Name = Scientific Name = Latin Name * Pharmaceutical Name = Pharmacop.Name = Crude Drug Name *Linnaeus : is a great Swedish biologist that we owe‫ ﻧﺪﻳﻦ‬the general adoption of the present binomial system(plants and animals), in which the first name denotes the genius (capital initial letters), while the second (specific) name denotes the species (small initial letters) , and the authority ( the name of the author who was the first to give a species or other taxon its name) the authority is given after the binomial Phytotherapy and chem. of natural products Dr. Khaled Tawaha  The 1st and the 2nd names are either written underlined or in italic( PC; most commonly used in literature) The specific name is usually chosen to indicate some striking characteristic of the plant for the example the hemlock with spotted stem is named Conium maculatum(maculatum means spotted) 1st authority and 2nd authority ( priority and How????, abbreviations ?) Aster bellidiastrum (L.) Scop. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  BIOLOGICAL AND GEOGRAPHICAL SOURCES OF DRUGS *→ Current estimates of the number of species of flowering plants range between 200 000 and 250 000 in some 300 families and 10 500 genera. *→only a small percentage of the total species has been examined chemically, and there is a large field for future research. *→ Folk medicine naturally varied according to the plants available in a particular climatic area and can be studied today in those more or less undisturbed primitive societies which still exist. *→Investigators are thus faced with the problem of making a systematic investigation from among the thousands of species still unexamined. Phytotherapy and chem. of natural products Dr. Khaled Tawaha *→For many areas of the world, the plants used in folklore have been adequately recorded; *→but for other regions for example, in South America, with its vast flora of potentially useful plants the art of folk medicine in aboriginal societies is in rapid decline owing to a changing mode of life of the people. Ethno botanists are currently fighting a battle against time to record such information before, within a generation or so, it is lost and with it a possible short cut to some medicinally useful plant. →The team-work of botanists, phytochemists, pharmacologists and clinicians →much useful Phytotherapy and chem. of natural products Dr. Khaled Tawaha  BIOLOGICAL SOURCES An examination of the list of drugs derived from natural sources, as included in any pharmacopoeia, soon reveals that the majority are derived from the Spermatophyta(the dominant seed bearing plants of the land). Phytotherapy and chem. of natural products Dr. Khaled Tawaha →Within the Spermatophyta the number of species and the number of useful medicinal plants is divided unevenly between the phyla Gymnospermae, which yields some useful oils, resins and the alkaloid ephedrine, and the Angiospermae, which is divided into 2-a Monocotyledons 2-b Dicotyledons →(both of these provide many useful drugs but especially the Dicotyledons). Phytotherapy and chem. of natural products Dr. Khaled Tawaha Of the other divisions of the plant kingdom, →the fungi provide a number of useful drugs, especially antibiotics →The algae are a source of a limited number of drugs (e.g. agar and alginic acid), but the full pharmacological importance of this large group of aquatic plants has still to be realized →Land animals provide such traditional pharmaceutical materials as gelatin, wool fat, beeswax and cochineal, and are a source of hormones, vitamins and sera. → Bacteriophyta are the production of antibiotics, their use in effecting various chemical conversions of added substrates and their employment in genetic engineering as, for example, → in the production of human insulin and the transformation of higher plant cells by incorporation of part of the DNA of a bacterial plastid into the plant genome. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  GEOGRAPHICAL SOURCES * Inspection of plants or plant- derived drugs included in the western pharmacopoeias shows them to be composed of: 1-Those which have survived from Greek and Roman eras (including some spices). 2-Those more characteristic of our own flora(e.g. digitalis in England) and introduced at latter data. 3-Pharmacologically active drugs added as a result of increased travel and colonial expansion(e.g. cinchona-quinine). 4-Drugs long used in other systems of medicine but of more recent introduction into the western medicine(e.g. rauwolfia- reserpine. 5- Recently discovered plant constituents of therapeutic value (e g. vinblastine and vincristine from Catharanthus roseus). 6- Semisynthetic products which depend on plant sources for starting material(e.g. steroidal hormones). Phytotherapy and chem. of natural products Dr. Khaled Tawaha  FACTORS WHICH DETERMINE THE COMMERCIAL GEOGRAPHICAL SOURCES OF A DRUG: 1-Suitability of the plant to a particular environment. 2- Governmental policies on the export of raw materials may affect geographical sources, as when the Indian government limited the export of crude (e.g. rauwolfia root). 3- National and international restrictions on the collection of wild plants (the Washington Convention on International Trade in Endangered‫ ﻣﮭﺪدة ﺑﺎﻻﻧﻘﺮاض‬Species (CITES) placed all species of Aloe except A. vera on the protected list without warning). Phytotherapy and chem. of natural products Dr. Khaled Tawaha 4-The economic factors associated with the production of a drug in a particular area. → Many plants grow equally well in numerous localities having similar climates; and as economic conditions change in one area, so the collection or cultivation of a drug plant may move in accordance. →The cultivation of Datura stramonium in England as a half-hardy annual has long become uneconomic and much material is now imported from eastern Europe. Similarly, the USA, which at one time utilized domestic supplies of the solanaceous drugs and digitalis, now obtains such raw materials from Yugoslavia. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  A taxonomic Approach to the Study of Medicinal Plants and Animal Derived Drugs Phytotherapy and chem. of natural products Dr. Khaled Tawaha 1-In this chapter the principal plant families of pharmaceutical interest are arranged according to the botanical scheme of Engler. 2-The chapter is divided into six parts: 2-1 Thallophytes(bacteria, algae, fungi and lichens) 2-2 Bryophytes(liverworts and mosses) 2-3 Pteridophytes(ferns,clubmoss and horsetails) 2-4 Gymnosperms(Spermatophyta→seed-bearing plants with unprotected ovules) 2-5 Angiosperms (Dicotyledons) 2-6 Angiosperms (Monocotyledons) Phytotherapy and chem. of natural products Dr. Khaled Tawaha Thallophytes Phytotherapy and chem. of natural products Dr. Khaled Tawaha 1-The old term 'thallophyte' includes those plants which are not differentiated into root, stem and leaves. Engler divides them into 13 phyla. 2-They include: A-Bacteria B- Algae C-Fungi D- Lichens. The positions of the main families of pharmaceutical interest are indicated below. For classification purposes the plant and animal kingdoms are each divided into a number of phyla and in addition to the phyla, the classification includes groupings of gradually diminishing size, namely divisions, classes, orders, suborders and families. Phytotherapy and chem. of natural products Dr. Khaled Tawaha A-BACTERIOPHYTA *-The bacteria are unicellular organisms, the great majority of which range in size from 0.75 to 8µm. ** - Bacteria exist in a number of characteristic shapes, namely: I. Rod-shaped or bacillary forms (e.g. Clostridium welchii, Escherichia coli and Bacillus subtilis). 2. Spherical or coccal forms, which can occur singly but are usually found in characteristic aggregates i.e. in chains (streptococci), in groups of two (diplococci), four (tetracocci). Aggregates of irregular pattern are said to be of staphylococcal form. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 3. Twisted or spirillar forms which, if having a single twist, belong to the genus Vibrio, while those with more than one twist belong to the genus Spirillum. 4. Branched forms which sometimes occur in the genus Mycobacterium. → Bacteria are able to carry out a very wide range of chemical reactions, some of which are used for identification and differentiation, in addition to forming the basis of many important industrial processes. →for example, in the production of vinegar, acet- one. →The production of hydrogen sulphide from and chem. of Phytotherapy organic sulphur compounds. natural products Dr. Khaled Tawaha → Bacteria are most important in medicine and pharmacy in the following respects: as disease-producing organisms (about 10% of bacteria are probably pathogenic); for producing antibiotics (Chapter 32). →In genetic engineering involving recombinant DNA (e.g. the production of human insulin). -Chemical conversion on added substrate Phytotherapy and chem. of natural products Dr. Khaled Tawaha B- Algae, ‫ طﺤﻠﺐ‬,‫طﺤﺎﻟﺐ‬ diatom,→ unicellular algae, have a silica skeleton, and show infinite variety in shape and in the sculpturing of the cell wall. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 2-Phaeophyta -Brown Algae -Red Algae → Chondrus crispus (yields carrageen or Irish moos) ‫ﻛﻨﺎﻓﺔ‬ ‫ ﻛﻮﻧﺪرس‬،‫ اﻟﻄﺤﻠﺐ اﻟﻔﺮﺿﻮﻓﻲ‬،‫اﻟﺒﺤﺮ‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha C- FUNGI ‫ ﻓﻄﺮ‬,‫ﻓﻄﻮر‬ 1- ASCOMYCETES: PROTOASCALES 1-1 Saccharomycetaceae: Dried yeast is prepared from a strain of Saccharomyces cerevisiae. 1-2 A member of the related family Cryptococcaceae is Candida utitis, which produces torula yeast, a rich source of proteins and vitamins. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 2-PLECTASCALES 2-1 Aspergillaceae → Penicillium yields important antibiotics such as penicillin and griseofulvin 3- CLAVICIPITALES 3-1 Clavicipitaceae Genera of the Clavicipitaceae include Claviceps (10 spp.) → C. purpurea (Ergot) ‫ﺻﺪى اﻟﻘﻤﺢ‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha D- LICHENS ‫اﺷﻨﺔ‬ 1- A lichen is a symbiotic association of an alga and a fungal partner. Some, particularly in arctic regions, are used as food. 2-Iceland moss, Cetraria islandica, has been used for disguising the taste of nauseous medicines and with other species for the treatment of cough. 3-Many lichens have antibiotic properties. Phytotherapy and chem. of natural products Dr. Khaled Tawaha BRYOPHYTA ‫ﺣﺰازﯾﺎت‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha 1-The phylum is divided into two classes, Hepaticae (liverworts) and Musci (mosses). 2-The pharmacologically active terpenoids (sesquiterpenes, diterpenes) and aromatic compounds of the bryophytes have been well studied. Phytotherapy and chem. of natural products Dr. Khaled Tawaha PTERIDOPHYTA ‫ﺳﺮﺧﺴﯿﺎت‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha 1- The Pteridophyta includes the Filices (ferns), Articulatae (horsetails) and Lycopsida (club mosses). 2- The dried sterile stems of the horsetail ‫أذﻧﺎب اﻟﺨﯿﻞ‬, Equisetum arvense are used in herbal medicine and are listed in the BHP. Preparations are used internally to treat inflammation and mild infections of the genito(‫)ﺗﻨﺎﺳﻠﻲ‬-urinary (‫ )ﺑﻮﻟﻲ‬tract. 3- The spores of lycopodium (Lycopodium clavatum)are used in limited extent in medicated snuffs,dusting powders and lubricants. As a dusting powder for rubber gloves it has been known to give rise to dermatitis Phytotherapy and chem. of natural products Dr. Khaled Tawaha Gymnosperm Phytotherapy and chem. of natural products Dr. Khaled Tawaha Spermatophyta(division),Gymno- and angio- spermae(subdivision),mono- and dicot(classes), -ales (order), -aceae(family), X y (G. spp.→Latin name) 1-The division Gymnospermae contains many fossil members. ‫ﻧﺒﺎت ﻣﻦ ﻋﺼﺮ ﺟﯿﻮﻟﻮﺟﻲ ﺳﺎﻟﻒ )ﻣﺘﺤﺠﺮة ﻓﻲ ادﻳﻢ‬ (‫اﻻرض‬ 2-Of the 11 orders in the Engler classification, it is only necessary to mention five orders and 10 families (In this course 4 orders and 5 families). Phytotherapy and chem. of natural products Dr. Khaled Tawaha Order Family Ginkgoales Ginkgoaceae Coniferales Pinaceae, Cupressaceae Gnetales Ephedraceae Taxales Taxaceae Phytotherapy and chem. of natural products Dr. Khaled Tawaha  GINKGOALES →Ginkgoaceae With the exception of Ginkgo biloba(‫ )ﺟﯿﻨﻜﻮ‬, maidenhair-tree, the plants of this order are found only as fossils. Ginkgo biloba (leaves) → In recent years, increasing use for the treatment of various diseases associated‫ ﻣﺮﺗﺒﻄﺔ‬with the ageing process,(improve short term memory) →Diterpenoids (constituents) flavonoids Phytotherapy and chem. of natural products Dr. Khaled Tawaha  TAXALES →Taxaceae 1- An order of only→ one family, which includes the genera Taxus (10 spp.), Pseudotaxus, 2-1 common yew Taxus baccata (‫ رﺟﻞ اﻟﺠﺮادة‬،‫)ﺧﺸﺐ اﻟﻄﻘﺴﻮس‬ → produces valuable wood. 2-2 All parts of the plant are very poisonous,and cattle and horses can die very rapidly after eating the leaves and stems. 3-In addition to alkaloids, a cyanogenetic glycoside and antitumour agent have been reported in the genus. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 4* Taxus brevifolia (the Pacific yew) 4-1The bark of this species yields the promising anticancer drug taxol, a nitrogenous diterpene. 4-2 Low yields from the bark and the scarcity of raw material leading to damage to forests by, often illegal, over-collection hampered the development of the drug. 4-3 The investigation of alternative sources has now led to tissue culture procedures for the production of taxol but the yields are still low. 4-4 A promising development involving a renewable‫ ﻣﺘﺠﺪد‬source has been the isolation of 10-deacetylbaccatin from the fresh needles of T. baccata in up to 0. I % yield →and its chemical conversion to taxol. 5- Other Taxus species investigated for taxane alkaloids.. Phytotherapy and chem. of natural products Dr. Khaled Tawaha  GNETALES →Ephedraceae 3- Various Ephedra species yield the drug ephedra and the alkaloid ephedrine (Use ?) nasal congestion! Ephedra sinica : ‫ اﻳﻔﯿﺪرا‬، ‫( ﻣﺎھﻮاﻧﻎ‬ma huang)english name of Eph.sinica Phytotherapy and chem. of natural products Dr. Khaled Tawaha  On February 9, 2004, the Food and Drug Administration (FDA) issued a final rule prohibiting the sale of dietary supplements containing ephedrine alkaloids (ephedra) because such supplements present an unreasonable risk of illness or injury. The rule will become effective in 60 days  Is it illegal to have ephedrine?  Dietary supplements containing ephedrine are illegal in the United States, with the exception of those used in traditional Chinese medicine, where its presence is noted by má huáng.  Angiosperms Monocotyledons Dicotyledons Phytotherapy and chem. of natural products Dr. Khaled Tawaha  DICOTYLEDONS Engler's classification of the Dicotyledons is given in a somewhat abbreviated form below. Phytotherapy and chem. of natural products Dr. Khaled Tawaha Subclass Archichlamydeae 2- Salicales : → Familie : Salicaceae → - Salix purpurea (Engl. Name:wilow): contains Phenolic glycosides→ Salicin) ‫ﺻﻔﺼﺎف‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha Cannabinaceae:→ (Cannabis sativa→hemp,cannabis) ‫ ﻗﻨﺐ ھﻨﺪي‬،‫ﻗﻨﺐ‬  THC(active ingredient),marijuana(leaves, flowers, resin), hashish(is only the resin of the plant) Phytotherapy and chem. of natural products Dr. Khaled Tawaha *-Santalales: → Families: Loranthaceae ‫اﻟﻌﺎﺋﻠﺔ اﻟﺪﺑﻘﯿﺔ‬ (Viscum album→ parasitic evergreen shrubs(grows on trees) Phytotherapy and chem. of natural products Dr. Khaled Tawaha  ‫ *ﺟﻮزة اﻟﻄﯿﺐ‬Myristicaceae: Myristica fragrans ( contains volatile oil and hallucinogenic substances) * Iliciaceae:Illicium verum (star anise) Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Guttiferales -1 Theaceae : Camellia sinensis ‫ ﺷﺎي‬tea (Alkaloids,Saponins, Tannins) -2 Hypericaceae: Hypericum perforatum (english: st.john’s wort) ‫ روﺟﺔ‬،‫ﺣﺸﯿﺸﺔ اﻟﻜﺒﺪ‬ -Used for depression Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Papaverales - Papaveraceae (rich alkaloids): Papaver somniferum, (white poppy, ‫)ﺧﺸﺨﺎش ﻣﻨﻮم‬, Opium: dried latex(mixture of compounds, mainly morphine ) Phytotherapy and chem. of natural products Dr. Khaled Tawaha  - Cruciferae : Brassica nigra(black mustard ‫ﺧﺮدل‬ ‫اﺳﻮد‬Cruciferae = brassicaceae - Rosales Hamamelidaceae(contains tannins, phenolic acids): Hamamelis virginiana (witch hazel ‫) ﺑﻨﺪق‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Rosaceae(contains cyanogenetic glycosides, saponins,tannins, terpenoids): Crataegus oxycanthoides Prunus amygdalus (‫ﻟﻮز‬ howthorn,‫زﻋﺮور اﻷودﻳﺔ‬ ) Phytotherapy and chem. of natural products Dr. Khaled Tawaha  - Erythroxylaceae( contains alkaloids, quinonones, saponins,flavonoids): Erythroxylum coca, E. novogranatense (coca ‫ ﺧﺸﺐ اﻻﺣﻤﺮ‬، ‫)ﻛﻮﻛﺎ‬ - Euphorbiaceae(contains latex, in some cases is poisonous or irritant): Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Hippocastanaceae: Aesculus hippocastanum(Horse chesnut ‫ طﻠﺔ اﻟﺤﺼﺎن‬،‫)ﻛﺴﺘﻨﺎء اﻟﮫﻨﺪي‬ (contains triterpenoid saponins) Phytotherapy and chem. of natural products Dr. Khaled Tawaha * Celastrales 1- Aquifoliaceae: Ilex paraguariensis(Mate) (‫ ﺷﺎي ﺑﺎرﻏﻮاي‬،‫ ﺷﺎي ﻣﺘﺔ‬،‫)ﻣﺘﺔ‬ contains alkaloids 2- Celastraceae: Catha edulis ( ‫ ﺷﺎي اﻟﺤﺒﺸﺔ‬،‫ ﺷﺎي ﺗﺨﺰﻳﻦ‬،‫ ﺷﺎي ﻳﻤﻨﻲ‬،‫)ﻗﺎت‬ (khat contains alkaloids) Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Vitaceae: Vitis vinifera ‫ ﻋﻨﺐ‬،‫ ورق اﻟﺪواﻟﻲ‬grape (red grapes(seeds) contains flavonoids,anthocyanins,phenolic acids) *- Sterculiaceae: Cola acuminate(Cola nuts) ‫ﻛﻮﻻ‬, cnotains alkaloids Theobroma cacao(Cacoa ‫ﻛﺎﻛﺎو‬, oil of theobroma,chocolate are prepared from Theobroma cacao) contains alkaloids Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Lythraceae: Lawsonia inermis ‫ﺣﻨﺎء‬: henna, leaves contain naphthoquinone( lawsone) - Caricaceae: Carica papaya‫(ﺑﺎﺑﺎي‬papaw, it is cultivated for the milky juice which is the source of the proteolytic enzyme papain. Phytotherapy and chem. of natural products Dr. Khaled Tawaha -Umbelliflorae 1- Araliaceae: Hedera helix(Ivy) (contains terpenoid saponins), ‫ ﺟﺒﻞ اﻟﻤﺴﺎﻛﯿﻦ‬،‫اﻟﻠﺒﻼب‬ Panax ginseng(contains terpenoid saponins) ‫ ﺟﻨﺴﻨﻎ‬ginseng 2- Umbelliferae= Apiaceae(contains Volatile oil, Resins, coumarins, triterpenoid saponins, alkaloids): Foeniculum vulgare‫(ﺷﻮﻣﺮ‬fennel), Pimpinella anisum‫( ﻳﺎﻧﺴﻮن‬aniseed), Ammi visnaga‫(ﺧﻠﺔ ﺑﻠﺪي‬visnaga),Carum carvi ‫(ﻛﺮاوﻳﺔ‬caraway),Coriandrum sativum‫(ﻛﺰﺑﺮة‬coriander), Conium maculatum ‫(ﺷﻮﻛﺮان‬spotted hemlock), Ferula spp.‫ﻛﻠﺦ‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Labiatae= Lamiaceae(contains volatile oils) : Melissa officinalis‫(ﻣﻠﯿﺴﺎ‬Melissa), Salvia officinalis‫( ﻣﯿﺮﻣﯿﺔ‬Sage), Thymus vulgaris(thyme)‫زﻋﺘﺮ‬, Mentha spp., Phytotherapy and chem. of natural products Dr. Khaled Tawaha * Solanaceae: Datura stramonium ‫(داﺗﻮرة‬datura,thornapple), Atropa belladonna ‫ﺳﺖ اﻟﺤﺴﻦ‬,Hyoscyamus niger ‫(اﻟﺴﻜﺮان‬henbane)Nicotiana tabacum ‫(ﺗﺒﻎ‬tobacco), Solanum spp., Capsicum spp.(‫أﻧﻮاع ﻓﻠﯿﻔﻠﺔ )ﺷﻄﺔ‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha  MONOCOTYLEDONS * As the name indicates, monocotyledons have an embryo with one cotyledon. 1- Liliiflorae 1-1 Liliaceae: -Allium sativum(garlic) -Aloe vera (aloe) ‫ﺻﺒﺎر‬ -Colchicum autumnale(autumn crocus or meadowsaffron) ‫ ﻟﺤﻼح‬،‫ﻋﯿﺼﻼن‬, Phytotherapy and chem. of natural products Dr. Khaled Tawaha - Graminea=Poacea: Oryza sativa ‫رز‬, Zea mays ‫ذرة‬, Triticum aestivum ‫ﻗﻤﺢ‬ Phytotherapy and chem. of natural products Dr. Khaled Tawaha ANIMAL PRODUCTS Phytotherapy and chem. of natural products Dr. Khaled Tawaha As with the Plant Kingdom, animals are classified into Phyla(division), Classes, Orders, Families, Genera and Species. Although the number of phar- macognostical products derived from animal sources is limited there has been, in recent years, an immense interest in the chemistry of many marine creatures as potential sources of drugs and biologically active materials. In this respect much research has been published on the simpler marine organisms. Listed below are selected animal phyla which embrace species of interest (the many animal products used in traditional medicines of Africa, India and the Orient are not included). Phytotherapy and chem. of natural products Dr. Khaled Tawaha  ARTHROPODA ‫ﻣﻔﺼﻠﯿﺎت‬ A very large phylum of jointed animals including the crustaceans, insects and arachnids. - Class Crustacea includes the shrimps, crabs, lobsters,. Of little medicinal significance, nevertheless brine shrimps are being increasingly used in place of higher animals for the preliminary testing of phytochemical for toxicity Phytotherapy and chem. of natural products Dr. Khaled Tawaha Class insecta: 1-order Hemiptera(Bugs): The cochineal beetle is an important colourant. Cochinal is the dried female insect Coccus cacti L. ‫ﺣﺸﺮة اﻟﻘﺮﻣﺰ‬ 2-Order coleopteran(Beetles): Beetles of the genus Cantharis, known as blistering beetles, posses vesicant properties and preparations of Cantharis vesicatoria were at one time used in Western medicine in the form of plasters as rubefacients. Their use continues in in the traditional medicine of Eastern Asia. Phytotherapy and chem. of natural products Dr. Khaled Tawaha 3.Order Hymenoptera (Ants. bees, etc.): → products derived from Apis millifica include honey,beeswax.royal jelly and propolis 4.Order Diptera (Flies. gnats and midges): The successful use of maggots in the treatment of wounds infected with antibiotic-resistant Staphylococcus aureus has received recent attention. →Sterile larvae of the common green bottle LuciIia sericata are used. Phytotherapy and chem. of natural products Dr. Khaled Tawaha PROPOLIS  CHORDATA 1. Class Osteichthycs (Bony fish).Cod and halibut important for their liver oils which contain vitamins A and D and eicosapentaenoic acid (dietary supplement) 2.Class Reptilia (Crocodiles, snakes and lizards)Snake venoms are important products. 3.Class Mammalia : important was the whale-product spermaceti but its collection now illegal. →Other pharmaceuticals include lard, suet,wool fat, gelatin, musk, catgut, insulin, hormones, blood and liver products, vaccines. Phytotherapy and chem. of natural products Dr. Khaled Tawaha