Genetic approach to alkaloids

Alkaloid biogenesis in an organism is determined This means that many specific genes participate in alkaloid metabolism, and gene participation in metabolism is a very important basis for understanding the alkaloids. As is widely recognized, the gene is a unit of hereditary information encoded in a discrete segment of a DNA molecule, which carries an enormous amount of genetic information. It has been generally estimated that human cells contain from 50000 to 100000 genes on 23 chromosomes. The...

Contents

Chapter 1 Definition, Typology and Occurrence of Alkaloids 1 2. Occurrence in nature 12 2.1. The Dogbane botanical family (Apocynaceae) 13 2.2. The Aster botanical family (Asteraceae) 17 2.3. The Logan botanical family (Loganiaceae) 19 2.4. The Poppy botanical family (Papaveraceae) 21 2.5. The Citrus botanical family (Rutaceae) 22 2.6. The Nightshade botanical family (Solanaceae) 25 2.7. The Coca botanical family (Erythroxylaceae) 27 2.8. The Borage botanical family (Boraginaceae) 28 2.9. The...

Regulation of stimulation

Many alkaloids are generally known to have stimulating properties, such as caffeine, cathine, theobromine and theophylline. These alkaloids are considered in many different medical applications. Caffeine is a known inhibitor of phosphodiesterase. Caffeine has an effect on calcium-mediated signalling namely it causes an increase of cAMP activity. Caffeine also has a competitive effect on the central adenosine receptor and is thought to increase analgesic activity. It is also known to be somewhat...

Alkaloids in plant protection

Many investigations have been carried out with the purpose of investigating the possibility of using alkaloids in plant protection617'618'619'620'621. Organic farming requires new possibilities to protect plants without strong synthetic pesticides. Natural botanicals and natural compounds extracted from plants are considered as possibilities. Alkaloids are considered useful for this purpose. Quinolizidine alkaloids, pure or in mixtures of plant extract, can be used to protect plants against...

Causers of locoism

Indolizidine alkaloids are also known as active biotoxins. Swansonine is especially cited in literature as a cause of locoism. This is a neurological lesion, especially in horses, cattle and sheep508. According to Elbein and Molyneux509 swansonine is toxic due to the imbibition of a-mannosidase, an enzyme needed for proper functioning of mammalian cells. It is also known that swansonine inhibits several hydrolases. In addition, Astragalus lentiginous produces lentiginosine, which is an alkaloid...

From stimulators to inhibitors and destroyers of growth

Waller and Nowacki16 distinguished the role of alkaloids in plants as growth stimulators and inhibitors and also as protective agents and reservoirs of nitrogen. Some alkaloids are known neurotransmitters in animals and can also be considered part of the signalling system. This system is constructed as a part of cell and metabolic operations controlled by functional mechanisms of biological membranes, channels, receptors and enzymes. It is known that some alkaloids, for example purine and...

Haemoglobinization of leukaemia cells

The biological activity of alkaloids can be demonstrated by fagaronine (Figure 82), an alkaloid isolated from Fagara zanthoxyloides Lam. (Rutaceae). This alkaloid alone has been tested by many research groups as biological agent of the haemoglobinization of human leukaemic cells372'373'374'375'376. One of the characteristics of leukaemic cells is escaping the normal regulatory pathway controlling cell proliferation and differentiation. As early as in 1972, Messmer et al.372 reported on...

Life regulation through the high and low cytotoxicity

Alkaloids from the plant family Amaryllidaceae are known to have a wide range of biological activities. They have analgesic, antiviral, anti-malarial, antineoplastic properties and display effects on the CNS. Elgorashi et al.354 have studied 25 Amaryllidaceae alkaloids for possible inhibitory activity of their acetylcholinesterase enzyme (AChE). This enzyme is biologically very important. According to the cholinergic hypothesis Alzheimer's disease symptoms result from AChE activity, which...

Material and methods

This case study was carried out in the Research and Teaching Laboratory of Applied Botany under the auspices of the Department of Biology of the University of Joensuu, Finland (N 62 36' E 29 40') from 1999 to 2003 as a part of the larger project, Quinolizidine alkaloids in arctic and sub-arctic flora. This large project explores the broader problem of QAs occurring in plants growing in northern ecosystems. This case study presents and discusses the research results from the first part of this...

Methods of analysis

This presentation of basic alkaloid synthesis pathways clearly reveals the diversity and complicity of this process in nature. Moreover, the large number of different pathways and synthesis routes proves the status of alkaloids as a phenomenon of the metabolic activity of organisms. Here, we have seen only the basic pathways and routes. In reality, each alkaloid has its own synthesis route. It is possible to find or to place it on one of the basic pathways. Certainly, experimental data is...

Regulation of Na ions and channels

As previously mentioned in this book, alkaloid biological activity is rather diverse, and alkaloids, therefore, have biological significance as histological regulators of metabolism. This significance is pertinent to the development of the applications. One such important role of some alkaloids is their influence on Na+ channels and interaction with receptors. Aconitine, ajmaline, sanguinarine (Figure 93) and sparteine have clinical uses in this respect. Aconitine causes an influx of Na+ ions...

Skeleton diversity

The skeleton nucleus of the alkaloid is the main criterion for alkaloid precursor determination. Many skeletons are produced in the process of alkaloid synthesis. Figure 24 illustrates some nuclei and skeletons supplied in the synthesis. Alkaloid Indole alkaloids Quinoline alkaloids Ergot alkalo Indolizine alkaloids Piperidine alkaloids Indolizine alkaloids Piperidine alkaloids Simple L-Tyrosine alkaloids Quinazoline ADP NAD L -Tryptophan ATP QH NADH2 -- - Tryptophan yAnthranilic C o Tyucinee...

The Coffee botanical family Rubiaceae

Madder) botanical family (Rubiaceae Juss.) (Table 15) consists of more than 400 genera and over 6000 species. It grows in the tropics and the sub-tropics. Plants belonging to this family include trees, bushes and liane. The Coffee plant family contains two major purines of adenine- guanine-derived alkaloids, the so-called purine alkaloids. Purine is a nitrogenous base of nucleotide, which consists of just purine and pentose sugar (D-ribose or 2 deoxy-D-ribose). Typical purine...

The Lily botanical family Liliaceae

The Lily botanical family (Liliaceae Adans., Juss.) (Table 14) is spread worldwide and contains more than 200 genera and around 3500 species. Some genera of this family produce L-tyrosine-derived alkaloids. The genus Kreysigia yields autumnaline, floramultine and kreysigine. The genus Colchicum (Colchicum L.) produces colchicine. Stereoidal alkaloids in this family are found in the Hellebore genus (Veratrum Bernch.). Jervine, cyclopamine (Figure 18), cycloposine, protoveratrine A and...

True alkaloids

True alkaloids derive from amino acid and they share a heterocyclic ring with nitrogen. These alkaloids are highly reactive substances with biological activity even in low doses. All true alkaloids have a bitter taste and appear as a white solid, with the exception of nicotine which has a brown liquid. True alkaloids form water-soluble salts. Moreover, most of them are well-defined crystalline substances which unite with acids to form salts. True alkaloids may occur in plants (1) in the free...

The Nightshade botanical family Solanaceae

The Nightshade plant family (Solanaceae Pers.), containing 90 genera and more than 2000 species distributed in all continents, particularly is abundant in alkaloids (Table 7). The plant species belonging to this family grow especially in the tropics and sub-tropics. However, the majority of the species occur in Central and South America. The L-ornithine (Figures 11 and 15) derived alkaloids occur in many species of this family. Hyoscyamine and hyoscine and cuscohygrine are in the genus...

Alkaloids as secondary metabolism molecules

Shikimic Acid

The precursors of true alkaloids and protoalkaloids are aminoacids (both their precursors and postcursors), while transamination reactions precede pseudoalka-loids (Tables 1 and 10). It is not difficult to see that from all aminoacids only a small part is known as alkaloid precursors (Table 19). Both true and proto alkaloids are synthesized mainly from the aromatic amino acids, phenylalanine, tyrosine (isoquinoline alkaloids) and tryptophan (indole alkaloids). Lysine is the Table 19 Amino acids...

Cell cultures

Alkaloids can be produced by using cell culture techniques in the same or a similar way as with other molecules624. Alkaloids such as ajmalicine, serpentine (C. roseus) and berberine (Coptis japonica) can produce remarkable quantities of alkaloids in in vitro cultures625 626. Generally, cell cultures produce species-specific alkaloids. In some cases cell cultures can produce more alkaloids than the whole plant, in relation to dry weight. This occurs, for example, in the cases of nicotine,...

List of Figures

1 Contemporary scheme of morphine. 2 2 Some alkaloids isolated by pharmaceutists Pierre Joseph Pelletier and Joseph Beiname Caventou during 1817-1821. 3 3 Schemes of taxol, vinblastine, vincristine and vincamine 5 4 An example of a true alkaloid 11 5 An example of protoalkaloids 11 6 An example of a pseudoalkaloid 12 7 The raw extraction of quinolizidine alkaloids 13 8 L-tryptophan with its aromatic side chain 15 9 The devil's-pepper genus, Rauwolfia serpentina 15 10 L-phenylalanine is a...

Mushroom

Alkaloids occur in many other botanical families. Moreover, there are alkaloids derived from L-tryptophan which occur in mushrooms genera Psilocybe mushrooms (Psilocybe), Conocybe mushrooms (Conocybe), Haymaker's mushrooms (Panaeolus) and Stoparia mushrooms (Stoparia). Serotonin, psilocin and psilocybin are basic alkaloids derived from these mushrooms (Figure 19). They are powerful psychoactive and neurotransmitter compounds. Recreational use of hallucinogenic mushrooms has been reported in...

Nicotinic acidderived alkaloids

Alkaloids derived from nicotinic acid contain a pyridine nucleus. Nicotinic acid itself is synthesized from L-tryptophan via N-formylkynurenine, L-kynurenine, 3-hydroxykynurenine, 3-hydroxyanthranilic acid and quinolinic acid. The pyridine nucleus is passed to alkaloids via dihydronicotinic acid, moving from dihydropyridine to nicotine and nornicotine (Figure 47). Dihydronicotinic acid is synthesized by the enzymatic activity of NADP and subsequently becomes 1,2-dihydropyridine by a reduction...

Applications

Abstract Alkaloid applications can be found in different areas. Some alkaloids are still used in modern medicine today as natural or modified compounds. Their use is connected to the regulation of Na+ ions and channels, mescaric, cholinergic receptor, acetylcholine esterase, opioid and opiate receptors, glycine and other receptors, as well as the regulation of micro-tubules of the spindle apparatus. Moreover, alkaloids are used in the regulation of microbial and schizonticide activity and as...

Influence on DNA

The phenethylisoquinoline alkaloids present in some members of the Lily family (Liliaceae) are known to be toxic. Wang and Wang457 have researched the activity of veratridine on rats. This alkaloid causes persistent opening of the voltage-gate Na+ channel and reduces its single-channel conductance by 75 . However, its toxicity is concentration dependent. The toxicity of iso-quinoline alkaloid berberine is low in concentrations 0.05 for living plant cells464. In these concentrations berberine...

Alkaloids in food

Alkaloidal plants used as food are small in number. The reason for this is the bioactivity and traditional use of alkaloids in medicines and drugs. Moreover, food is checked and controlled with the purposes of keeping alkaloid-contaminated food off the market. However, cases where pyrrolizidine alkaloids were found in the honey produced by bees that had foraged on the flowers of Echium and Senecio species are documented475'495'591. In these relatively old studies, bees had been feeding only on...

Regulation of schizonticide activity

Quinidine and quinine have schizonticide activity due to the inhibition of nucleic acid synthesis through DNA intercalation. This activity is also based on carbohydrate metabolism. The action of both of these alkaloids is a result of their binding to sarcoplasmic reticular vesicles and the resulting reduced uptake of Ca2+. These alkaloids are also active on Na+ and K+-ATPase, both in an encouraging or inhibiting sense. Both alkaloids therefore have been developed as strong anti-malarial...

Alkaloids - Secrets Of Life

This book is intended to be a presentation of alkaloids from chemical, biological and ecological points of view. It is a text for chemists, biologists and ecologists alike. However, the intended audience of this work is not limited to scientists, teachers and other present and future specialists. In fact, I wrote this book because I felt the need for it as a university educator and as a scientific enthusiast on the subject. My purpose was to compose a beneficial text for an academic and...

Alkaloids as biological fertilizers

Alkaloids from many plants are considered to be used as biological fertilizers in ecological cultivation. This is very important especially in cases when more attention is given to these plants, which play not only a role in production but also in the cyclical maintenance of a field, garden or forest ecosystems614'615'616. Plants containing alkaloids, for example lupines, have the ability to establish complexes with the soil and with the rhizosphere. The excretion of many chemicals from roots...

Antiparasitic activity

A parasite is an organism living in or on, and metabolically depending on, another organism. Endoparasites live inside an organism, and ectoparasites live on the surface of the host. Parasites can be carnivorous if living with animals or herbivorous if living with plants. Analyses of parasite host suggest strong evidence of anti-carnivorous anti-herbivorous action of alkaloids. A good example is with protozoan parasites Plasmodium spp. injected into humans by mosquitoes of the genus Anopheles....

The Logan botanical family Loganiaceae

The Logan plant family Loganiaceae Lindl. is abundant in species containing L-tyrosine Figure 12 derived alkaloids Table 4 . Thirty genera and more than 500 species belong to this family although new systematic research has proposed that Loganiaceae should be divided into several families319. The Logan plant genus Strychnos L. is especially rich in many of alkaloids such as strychnine, Figure 12. L-tyrosine, with its aromatic side chain, is a precursor of phenylethylamino- and isoquinoline...

Biogenesis of alkaloids

The synthesis and structural analysis of alkaloids leads to the following basic questions why are alkaloids synthesized in an organism and on which mechanism is alkaloid formation and degradation dependent in the life cycle It is known that alkaloids have a genetic nature59 and that alkaloid content is diverse inside and between the species16. In nature the same species of plants may have both high and low alkaloid content120121. Natural hybridization has been successfully used in plant...

The Legume botanical family Fabaceae

Calabar Bean

Alkaloids derived from L-ornithine, L-lysine, and L-trypthophan occur in the Legume plant family Fabaceae Juss. Table 9 . This plant family is the third largest botanical family, with 650 genera and 18000 species in the humid tropics, sub-tropics, temperate and sub-arctic zones around the Globe118. L-ornithine-derived alkaloids such as senecionine are present in the genus Crota Crotalaria L. . The most typical alkaloids for this botanical family are L-lysine Figure 16 derived alkaloids, such as...

Pseudoalkaloids

Pseudoalkaloids are compounds, the basic carbon skeletons of which are not derived from amino acids31. In reality, pseudoalkaloids are connected with amino Figure 6. An example of a pseudoalkaloid. Acetate-derived alkaloid pinidine is extracted from the Pinus species, for example, from Pinus penderosa. Photo T. Aniszewski . Pinidine has antimicrobial activity. Figure 6. An example of a pseudoalkaloid. Acetate-derived alkaloid pinidine is extracted from the Pinus species, for example, from Pinus...

Animals

Alkaloids are also found in the animal kingdom, especially in millipedes, salamanders, toads, frogs, fish and mammals. They occur particularly in the genera Saxidomus, Salamandra, Phyllobates, Dendrobates, Castor and Moschus. Moreover, alkaloid molecules are found in such genera as Solenopsis, Odon-tomachus, Glomeris and Polyzonium. Many alkaloids have been recently isolated from marine environment, especially from the sponges197. The discovery of ptilomycalin A from the sponges Ptilocaulis...

Eduline Circulatory System

Structural development of phenyl and phenylpropyl alkaloids. alkaloids e.g., eserine and ergot alkaloids e.g., ergotamine . Indole alkaloids form a very important group from the perspective of their application. The a for structural development of serotonin simple indole alkaloid is L-tryptophan, and the ft is 5-hydroxy-L-tryptophan Figure 64 . Serotonin is a monoamine. It is a bioactive alkaloid known as a neurotransmitter. It has been found in the cardiovascular system, in blood...

Alkaloid Index

25 2-hydroxy-4-methoxy-3- 3' -methyl-2'- butenyl -quinoline 24 2-methoxyl-3- 3-indolyl -propionic acid 31, 39 2-O,N-dimethylliriodendronine 35, 45 3 R -benzoyloxy-2 R -methyl-6 R - 11'-oxododecyl -piperidine 152 3'-hydroxy-N-methylcoclaurine 176 3-hydroxysarpagine 16 3-methoxy-tabernaelegantine C 16 3-R S-hydroxy-conodurine 16 16 3 8,13a-dihydroxylupanine 31 3 -hydroxylupanine 31 4-hydroxystachydrine 10, 11, 34 4'-O-methylnorbelladine 78, 79 4 -hydroxy-2-oxosparteine 101 4 -tigloyloxylupanine...

Tryptophanderived alkaloids

Diagram Alkaloids

Alkaloids derived from L-tryptophan hold the indole nucleus in a ring system. The ring system originates in the shikimate secondary compounds building block and the anthranilic acid pathway. It is known that the shikimate block, in general, and anthranilic acid, in particular, are precursors to many indole alkaloids. However, there are many rearrangement reactions which can convert the indole ring system into a quinoline ring. In this pathway, L-tryptophan is enzymatically transferred to...

The Ecological Role of Alkaloids

Abstract Alkaloids are a special group of secondary compounds and are part of an organism's adaptation mechanism to its living environment. They are not toxic when stored, but become toxic as a result of cell pH change. The defensive function of alkaloids is only secondary, and connected to internal immune and regulation processes. Animal responses to alkaloids are very diverse. Some animals can tolerate alkaloids relatively well, while others are harmed or even poisoned by them. Animal...

The Dogbane botanical family Apocynaceae

Some plant families are especially rich in alkaloids. The Dogbane botanical family Apocynaceae Lindl., Juss. is a good example Table 2 . This family is distributed worldwide, especially in tropical and sub-tropical areas. The Dogbane family is a large botanical taxa containing at least 150 genera and 1700 species. Alkaloids are especially abundant in the following Table 2 General botanical characteristics of the Dogbane family Opposite or verticillate with reduced stipules Pinnateveined...

Protoalkaloids

Protoalkaloids are compounds, in which the N atom derived from an amino acid is not a part of the heterocyclic31. Such kinds of alkaloid include compounds derived from L-tyrosine and L-tryptophan see Table 1 . Protoalkaloids are those Definition, Typology and Occurrence of Alkaloids Table 1 Main types of alkaloids and their chemical groups Cocaine Hyoscyamine Scopolamine hyoscine lycopsamine Acetyl-intermedine Europine Homospermidine Ilamine Anaferine Lobelanine Lobeline N -methyl pelletierine...