Che106 Technical Communicatin Chemical Engineering Departmant Engineering Faculty Ege University Bornova/İzmir

ALKALOIDS

Prepared by Alper Baran SÖZMEN

Applications a. Bio-synthesis 9.Table of Contents 1. d. History. Classification a. In Medicine b. True alkaloids Protoalkaloids Polyamine alkaloids Peptide (cyclopeptide) alkaloids Pseudalkaloids 5. Naming and Definition 4. References . Properties 6. Summary 2. Introduction 3. b. Distribution in Nature 7. e. c. Extraction 8. In Agriculture 10.

Introduction .

Summary .

and proved a significant step forward in chemistry and pharmacology. "-inine". "-aline".W. which have strong physiological activity. chemists stressed that alkaloids were biogenic. first isolated morphine. peptides. Meißner .W. Later. Scientists are recognizing the vital importance of these products for biology. If several alkaloids are extracted from one plant then their names often contain suffixes "-idine". medicine and chemistry. nitrogen-containing and mostly N-heterocyclic compounds. Difficulties with the definition of such a group of secondary and natural molecules as alkaloids stem from similarities of alkaloids with other secondary compounds. Meißner observed that these compounds appeared “like alkali”. and is in many cases a source of academic controversy. This was in 1805. indeed almost identical. atropine is isolated from the plant Atropa belladonna. Friedrich Sertürner. quinine. Meißner. medicine and chemistry.[and is derived from late Latin root Latin:alkali (which. [3] . strychnine is obtained from the seed of Strychnine tree. The term “alkaloid” was first mentioned in 1819 by W. a remarkable range of other alkaloids. and so named them alkaloids. an apothecary’s assistant from Westphalia. and a very small unit of global nature both in the material sense and in processes as they occur. Carl F. an apothecary from Halle. However. [1] The name "alkaloids" (German: Alkaloide) was introduced in 1819 by the German chemist Carl F. etc. [2] Chemistry has provided a definition of alkaloids in purely chemical terms. and the fact that there remain some differences of accentuation in alkaloid definitions. Many individual names are formed by adding the suffix "-ine" to the species or generic alkaloids.History. In this definition it is also stated that amino acids. the term came into wide use only after the publication of a review article by O. What has been learnt about alkaloids from the last 200 years of studies? It is fascinating that alkaloids are just a product of nature. For example. Inspite of differences between the research fields of biology. In another chemical definition. Using the method developed by Friedrich Sertürner. comes from the Arabic al qualja . such as febrifuge. are often toxic. it is stated only that alkaloids are nitrogen-containing compounds derived from plants and animals30."ashes of plants") and the suffix Greek: ειδοσ "like". amino sugars and antibiotics are not considered as to be alkaloids. Jacobsen in the chemical dictionary of Albert Ladenburg in the 1880s. There are also at least 86 alkaloids containing the root "vin" (extracted from the Vinca plant). caffeine and veratrine. and retain their own basic chemical properties. "-anine". from 1817 to 1821. Naming and Definition The definition of the term alkaloid is not a simple one. the pharmacists Pierre Joseph Pelletier and Joseph Benaimé Caventou isolated. in turn. It is also stated that there are a few exceptions to this definition29. Chemists stress that alkaloids are any group of complex heterocyclic nitrogen compounds. one of the most important alkaloids in the applied sense. such definitions are very similar. nucleosides. There is no unique method of naming alkaloids. Attempts to define the term “alkaloid” originated at the time of the discovery of these compounds.

Alkaloids are generally classified by their common molecular precursors. it is possible to divide alkaloids into (1) neutral or weakly basic molecules (e. the group of compounds mentioned as non-natural alkaloids is growing especially rapidly as a result of bio-organic and stereochemistry research.. they require compromises in borderline cases. From the point of view of biological activity. first classification methods combined alkaloids by the common natural source.g. However. certain N-oxides such as indicine). (2) chemical structures and (3) biosynthetic pathway. (3) marine alkaloids. Nowadays.[6] Alkaloids are often divided into the following major groups: PİCTURE HERE .g. This is necessary since the sources of infections (micro-organisms) are constantly changing their species and infection ability. lactams such as ricinine. whereas pseudoalkaloids are not derived from these compounds.Classification Compared with most other classes of natural compounds. From a structural point of view. anuran. (2) protoalkaloids and (3) pseudoalkaloids. e. (4) moss alkaloids. based on the biological pathway used to construct the molecule. becoming resistant to medicines and antibiotics. [4] More recent classifications are based on similarity of the carbon skeleton or biogenetic precursor.. There are three main types of alkaloids: (1) true alkaloids.. (5) fungal and bacterial alkaloids and (6) non-natural alkaloids (structurally modified or analogues). alkaloids are divided according to their shapes and origins. mammalian and arthropod alkaloids). alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids. a certain type of plants. (2) animal-derived alkaloids (e. Pharmacological research and the drug industry rapidly advance and promote the most promising new molecules for possible production applications. [5] Alkaloids can be classified in the terms of their (1) biological and ecological activity.g. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete. True alkaloids and protoalkaloids are derived from amino acids. nicotine contains a pyridine fragment from nicotinamide and pyrrolidine part from ornithine and therefore can be assigned to both classes. for example. Historically.

in which the N atom derived from an amino acid is not a part of the heterocyclic31.a. All true alkaloids have a bitter taste and appear as a white solid. Chini et al. l-phenylalanine/l-tyrosine.33 have found new alkaloids. stachydrine and 4-hydroxystachydrine. Hordenine. Protoalkaloids are those with a closed ring. and are those compounds in which decarboxylated amino acids are condensed with a nonnitrogenous structural moiety. True alkaloids may occur in plants (1) in the free state. Boscia angustifolia is used for the treatment of mental illness. and occasionally to combat pain and neuralgia. Moreover. being perfect but structurally simple alkaloids.[7] PİCTURE HERE b. (2) as salts and (3) as N-oxides. morphine and usambarensine. True alkaloids True alkaloids derive from amino acid and they share a heterocyclic ring with nitrogen. dopamine. Such kinds of alkaloid include compounds derived from l-tyrosine and l-tryptophan. True alkaloids form water-soluble salts. most of them are well-defined crystalline substances which unite with acids to form salts. with the exception of nicotine which has a brown liquid. quinine. They form a minority of all alkaloids. The species from this genus have been used in folk medicine in East and South Africa. These alkaloids have a pyrroline nucleus and are basic alkaloids in the genus Boscia. The primary precursors of true alkaloids are such amino acids as l-ornithine.[8] PİCTURE HERE . l-lysine. Examples of true alkaloids include such biologically active alkaloids as cocaine. l-tryptophan and l-histidine23_32. a plant belonging to the Capparidacea family. Protoalkaloids Protoalkaloids are compounds. These alkaloids occur in a limited number of species and families. derived from Boscia angustifolia. mescaline and yohimbine are good examples of these kinds of alkaloid. These alkaloids are highly reactive substances with biological activity even in low doses.

Peptide (Cyclopeptide) alkaloids Cyclopeptide alkaloids are defined as basic compounds embodying an ansa structure. i. ephedrine. Pandaceae. They can also result from the amination and transamination reactions32 of the different pathways connected with precursors or postcursors of amino acids. the basic carbon skeletons of which are not derived from amino acids31.or polycyclic.Polyamine alkaloids Polyamines either in their free basic form or conjugated to other molecules such as fatty acids.e. capsaicin. connected by a C16 diamido bridge.[10] PİCTURE HERE e. if there is a suitable aldehyde or ketone. as well as steroidal alkaloids. Cellastraceae. In reality. animals. Sterculiaceae and Urticaeae. the N atom can also be donated by an amino acid source across a transamination reaction. They are widely distrubuted among plants of the Rhamnaceae family. but their occurence has also been confirmed in representatives of Asteraceae. Menispermac eae. Pseudoalkaloids can be acetate and phenylalaninederived or terpenoid. The N atom is inserted into the molecule at a relatively late stage. They are derived from the precursors or postcursors (derivatives the indegradation process) of amino acids. cinnamic acids or other biomolecules occur in nature and show a large variety of biological activities. pseudoalkaloids are connected with amino acid pathways.3 or 1. Rubiaceae. mono. Euphorbiaceae.Pseudoalkaloids Pseudoalkaloids are compounds.4 positions of a benzene ring. in which a 10 or 12 membered peptide type bridge spans 1. theobromine and pinidine. In 1996 we reported the first isolation of a compound containing both polyamines. These alkaloids can also be derived from nonaminoacid precursors. spermidine and spermine. This alkaloid was called tenuilobine) because of its natural source the plant Oncinotis tenuiloba Stapf (Apocynaceae). Examples of pseudoalkaloids include such compounds as coniine. The structures of these compounds can be linear. [9] PİCTURE HERE d. [11] . Certainly.c. plants and microorganisms. for example. in the whole biosphere. in the case of steroidal or terpenoid skeletons. They occur in humans. caffeine. solanidine.

PİCTURE HERE Properties .