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Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral[2] and even weakly acidic properties.[3] Also some synthetic compounds of similar structure are attributed to alkaloids.[4] In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.[5] Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals, and are part of the group of natural products (also called The first individual alkaloid, morphine, was isolated in 1804 from [1] secondary metabolites). Many alkaloids can be purified poppy (Papaver somniferum). from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine; the psychedelic psilocin; the stimulant caffeine; nicotine;[6] the analgesic morphine; the antibacterial berberine; the anticancer compound vincristine; the antihypertension agent reserpine; the cholinomimeric galatamine; the spasmolysis agent atropine; the vasodilator vincamine; the anti-arhythmia compound quinidine; the anti-asthma therapeutic ephedrine; and the antimalarial drug quinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a bitter taste.[7] The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut.[8] Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines, and antibiotics are usually not called alkaloids.[2] Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids.[9] Some authors, however, consider alkaloids a special case of amines.[10][11][12]
Alkaloid
Naming
The name "alkaloids" (German: Alkaloide) was introduced in 1819 by the German chemist Carl F.W. Meissner,[13] and is derived from late Latin root Latin: alkali (which, in turn, comes from the Arabic al-qalw "ashes of plants") and the suffix Greek: - "like".[14] However, the term came into wide use only after the publication of a review article by O. Jacobsen in the chemical dictionary of Albert Ladenburg in the 1880s.[15] There is no unique method of naming alkaloids.[16] Many individual names are formed by adding the suffix "ine" to the species or genus name.[17] For example, atropine is isolated from the plant Atropa belladonna, strychnine is obtained from the seed of Strychnine tree (Strychnos nux-vomica L.).[5] If several alkaloids are extracted from one plant then their names often contain suffixes "idine", "anine", "aline", "inine", etc. There are also at least 86 alkaloids containing the root "vin" (extracted from the Vinca plant).[18]
History
Alkaloid-containing plants have been used by humans since ancient times for therapeutic and recreational purposes. For example, medicinal plants have been known in the Mesopotamia at least around 2000 BC.[19] The Odyssey of Homer referred to a gift given to Helen by the Egyptian queen, a drug bringing oblivion. It is believed that the gift was an opium-containing drug.[20] A Chinese book on houseplants written in 1st3rd centuries BC mentioned a medical use of Ephedra and opium poppies.[21] Also, coca leaves have been used by South American Indians since ancient times.[22]
Friedrich Sertrner, the German chemist who first isolated morphine from opium.
Extracts from plants containing toxic alkaloids, such as aconitine and tubocurarine, were used since antiquity for poisoning arrows.[19]
Studies of alkaloids began in the 19th century. In 1804, the German chemist Friedrich Sertrner isolated from opium a "soporific principle" (Latin: principium somniferum), which he called "morphium" in honor of Morpheus, the Greek god of dreams; in German and some other Central-European languages, this is still the name of the drug. The term "morphine", used in English and French, was given by the French physicist Joseph Louis Gay-Lussac). A significant contribution to the chemistry of alkaloids in the early years of its development was made by the French researchers Pierre Joseph Pelletier and Joseph Bienaim Caventou, who discovered quinine (1820) and strychnine (1818). Several other alkaloids were discovered around that time, including xanthine (1817), atropine (1819), caffeine (1820), coniine (1827), nicotine (1828), colchicine (1833), sparteine (1851), and cocaine (1860).[23]
Alkaloid The first complete synthesis of an alkaloid was achieved in 1886 by the German chemist Albert Ladenburg. He produced coniine by reacting 2-methylpyridine with acetaldehyde and reducing the resulting 2-propenyl pyridine with sodium.[24][25] The development of the chemistry of alkaloids was accelerated by the emergence of spectroscopic and chromatographic methods in the 20th century, so that by 2008 more than 12,000 alkaloids had been identified.[26]
Bufotenin, an alkaloid from some toads, contains an indole core and is produced in living organisms from the amino acid tryptophan.
Classification
Compared with most other classes of natural compounds, alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids.[27] First classification methods have historically combined alkaloids by the common natural source, e.g., a certain type of plants. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete.[5][28] More recent classifications are based on similarity of the carbon skeleton (e.g., indole-, isoquinoline-, and pyridine-like) or biogenetic precursor (ornithine, lysine, tyrosine, tryptophan, etc.).[5] However, they require compromises in borderline cases;[27] for example, nicotine contains a pyridine fragment from nicotinamide and pyrrolidine part from ornithine[29] and therefore can be assigned to both classes.[30] Alkaloids are often divided into the following major groups:[31] 1. "True alkaloids", which contain nitrogen in the heterocycle and originate from amino acids.[32] Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine[33]) or peptide fragments (e.g. ergotamine[34]). This group also includes piperidine alkaloids coniine and coniceine[35] although they do not originate from amino acids.[36] 2. "Protoalkaloids", which contain nitrogen and also originate from amino acids.[32] Examples include mescaline, adrenaline and ephedrine. 3. Polyamine alkaloids derivatives of putrescine, spermidine, and spermine. 4. Peptide and cyclopeptide alkaloids.[37] 5. Pseudalkaloids alkaloid-like compounds that do not originate from amino acids.[38] This group includes, terpene-like and steroid-like alkaloids,[39] as well as purine-like alkaloids such as caffeine, theobromine and theophylline.[40] Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.[40][41]
The nicotine molecule contains both pyridine (left) and pyrrolidine rings (right).
Alkaloid Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine and homoaporphines do not contain isoquinoline fragment, but are, in general, attributed to isoquinoline alkaloids.[42] Main classes of monomeric alkaloids are listed in the table below:
Class Major groups Main synthesis steps Examples
Alkaloids with nitrogen heterocycles (true alkaloids) Pyrrolidine derivatives [43] Ornithine or arginine putrescine Cuscohygrine, hygrine, N-methylputrescine hygroline, [44] [43][45] N-methyl-1-pyrroline stachydrine
Tropane derivatives
[46]
Ornithine or arginine putrescine Atropine, scopolamine, [43][46][47] N-methylputrescine hyoscyamine [] 1 N-methyl- -pyrroline
Cocaine, ecgonine
[46][48]
Pyrrolizidine derivatives
[49]
Non-esters
Retronecine, heliotridine, [49][50] laburnine Indicine, lindelophin, [49] sarracine Platyphylline, [49] trichodesmine
1-aminopyrrolizidines (lolines)
In fungi: L-proline + L-homoserine N-(3-amino-3-carboxypropyl)proline [51][52] norloline Lysine cadaverine [55] 1-piperideine
[36]
Alkaloid
[57][58] Quinolizidine derivatives [57]
5
Lupinine group Cytisine group Sparteine group
Sparteine, lupanine, [57] anahygrine Matrine, oxymatrine, [57][60][61] allomatridine Ormosanine, [57][62] piptantine Lysine -semialdehyde of -aminoadipic acid pipecolic acid [64] 1 indolizidinone Swainsonine, [65] castanospermine
Matrine group
Ormosanine group
Indolizidine derivatives
[63]
Pyridine derivatives
[66][67]
Trigonelline, ricinine, [66][69] arecoline Nicotine, nornicotine, [66][69] anabasine, anatabine Actinidine, gentianine, [70] pediculinine
Polycyclic noncondensing pyridine derivatives Polycyclic condensed pyridine derivatives Sesquiterpene pyridine derivatives Isoquinoline derivatives and related [71] alkaloids Simple derivatives of [72] isoquinoline Derivatives of 1- and [75] 3-isoquinolines Derivatives of 1- and 4-phenyltetrahydroisoquinolines [72] Derivatives of [77] 5-naftil-isoquinoline Derivatives of 1- and [78] 2-benzyl-izoquinolines Cularine group [79] [80] Nicotinic acid, isoleucine [12]
Evonine, hippocrateine, [67][68] triptonine Salsoline, lophocerine [71][72] N-methylcoridaldine, [75] noroxyhydrastinine Cryptostilin [72][76]
Ancistrocladine
[77]
Alkaloid
[72]
Protoberberines
Berberine, canadine, ophiocarpine, mecambridine, [82] corydaline [72] Hydrastine, narcotine [83] (Noscapine) Fumaricine [80]
Phthalidisoquinolines
Spirobenzylisoquinolines
[72]
Emetine, protoemetine, [84] ipecoside Sanguinarine, oxynitidine, [85] corynoloxine Glaucine, coridine, [86] liriodenine Pronuciferine, glaziovine [72][81] Kreysiginine, multifloramine [87] Bulbocodine [79]
Benzophenanthridines
[72]
Aporphines
[72]
Proaporphines
[72]
Homoaporphines
[87]
[87]
Morphine, codeine, thebaine, [89] sinomenine [90] Kreysiginine, androcymbine [88] [72] Imerubrine [72] [91]
Homomorphines
Tropoloisoquinolines Azofluoranthenes
[72]
Rufescine, imeluteine
Lycorine, ambelline, tazettine, galantamine, [93] montanine Erysodine, erythroidine [72] Atherosperminine [76]
[72][82]
[72]
Alkaloid
7
Ibotenic acid Muscimol Ibotenic acid, Muscimol
Isoxazole derivatives
Thiazole derivatives
[97]
Quinazoline derivatives
[100]
[102] Febrifugine
Acridine derivatives
[94]
Anthranilic acid
[103]
Quinoline derivatives
[106][107]
Simple derivatives of quinoline derivatives of 2 quinolones and 4-quinolone Tricyclic terpenoids Furanoquinoline derivatives
Flindersine
Dictamnine, fagarine, [107][112][113] skimmianine Tryptophan tryptamine strictosidine (with secologanin) [74][] korinanteal cinhoninon Quinine quinidine [111] cinchonine, cinhonidine
Quinines
Alkaloid
[89] Simple indole derivatives [114]
8
Non-isoprene indole alkaloids Tryptophan tryptamine or [115] 5-hydroxitriptofan Serotonin, psilocybin, dimethyltryptamine (DMT), [116][117] bufotenin Harman, harmine, harmaline, [114] eleagnine [119] Physostigmine (eserine), etheramine, physovenine, [119] eptastigmine Semiterpenoid indole alkaloids Ergot alkaloids [89] Tryptophan chanoclavine agroclavine elimoclavine [119] paspalic acid lysergic acid Monoterpenoid indole alkaloids [115] Corynanthe type alkaloids Tryptophan tryptamine [115] strictosidine (with secologanin) Ajmalicine, sarpagine, vobasine, ajmaline, yohimbine, reserpine, [121][122] mitragynine, group strychnine and (Strychnine brucine, aquamicine, [123] vomicine ) Ibogamine, ibogaine, [115] voacangine Vincamine, vinca alkaloids, vincotine, [124][125] aspidospermine Directly from histidine [126] Histamine, pilocarpine, [94][126] pilosine, stevensine Ergotamine, ergobasine, [120] ergosine
Indole derivatives
Imidazole derivatives
[94]
Purine derivatives
[127]
Xanthosine (formed in purine Caffeine theobromine biosynthesis) 7 methylxantosine theophylline saxitoxin [128][129] 7-methyl xanthine theobromine [74] caffeine
Alkaloid
[81]
-Phenylethylamine derivatives
Tyrosine or phenylalanine dioxyphenilalanine dopamine adrenaline and mescaline tyrosine tyramine phenylalanine 1-phenylpropane-1,2-dione cathinone ephedrine and [12][41][130] pseudoephedrine
Tyramine, ephedrine, pseudoephedrine, mescaline, cathinone, catecholamines (adrenaline, noradrenaline, [12][131] dopamine)
Colchicine alkaloids
[132]
Colchicine, colchamine
[132]
Muscarine
[134]
Glutamic acid 3-ketoglutamic acid Muscarine, allomuscarine, muscarine (with pyruvic epimuscarine, [135] [134] acid) epiallomuscarine
Benzylamine
[136]
Polyamines alkaloids [139] Putrescine derivatives ornithine putrescine spermidine Paucine [140] spermine [139]
Spermine derivatives
[139]
Alkaloid
[37]
10
Nummularine C type
Nummularine C, [37] Nummularine S Ziziphine A, sativanine H [37] Frangulanine, scutianine J [141] Scutianine A [37] [141]
Ziziphine type
Frangulanine type
Integerrine, discarine D
Amfibine B type Peptide alkaloids with a 15-membered [141] cycle Mucronine A type
Pseudoalkaloids (terpenes and steroids) Diterpenes [34] Lycoctonine type Mevalonic acid izopentenilpyrophosfate geranyl [142][143] pyrophosphate Aconitine, delphinine [34][144]
Steroids
[145]
Cholesterol, arginine
[146]
Alkaloid
11
Properties
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as nicotine[148] or coniine,[24] are typically volatile, colorless, oily liquids.[149] Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange).[149] Most alkaloids are weak bases, but some are amphoteric, for example theobromine and theophylline.[150] Most alkaloids are poorly soluble in water but readily dissolve in organic solvents, such as diethyl ether, chloroform and 1,2-dichloroethane. However, caffeine dissolves well in boiling water.[150] With acids, alkaloids form salts of various strengths. Those salts are usually soluble in water and alcohol and poorly soluble in most organic solvents. Exceptions include scopolamine hydrobromide, which is soluble in organic solvents and water-soluble quinine sulfate.[149] Most alkaloids have a bitter taste. It is believed that plants evolved the the corn lily plant. The cyclopia in the calf is ability to produce these bitter substances, many of which are induced by the alkaloid cyclopamine present in the plant. poisonous, in order to protect themselves from animals; however, [151] animals in turn evolved the ability to detoxify alkaloids. Some alkaloids can produce developmental defects in the offspring of animals that consume them but cannot detoxify them. A characteristic example is the alkaloid cyclopamine, which is present in the leaves of corn lily. During the 1950s, up to 25% lambs born by sheep that had grazed on corn lily suffered serious facial defects. Those defects ranged from deformed jaws to cyclopia (see picture). After decades of research, in 1980s, the substance that was responsible for the deformities was identified as the alkaloid 11-deoxyjervine, which was renamed cyclopamine.[152]
Head of a lamb born by a sheep that ate leaves of
Distribution in nature
Alkaloids are generated by various living organisms, especially by higher plants about 10 to 25% of those contain alkaloids.[153][154] Therefore, in the past the term "alkaloid" was associated with plants.[155] The alkaloids content in plants is usually within a few percent and is inhomogeneous over the plant tissues. Depending on the type of plants, the maximum concentration is observed in the leaves (black henbane), fruits or seeds (Strychnine tree), root (Rauwolfia serpentina) or bark (cinchona).[156] Furthermore, different tissues of the same plants may contain different alkaloids.[157] Beside plants, alkaloids are found in certain types of fungi, such as psilocybin in the fungus of the genus Psilocybe, and in animals, such as bufotenin in the skin of some toads.[16] Many marine organisms also contain alkaloids.[158] Some amines, such as adrenaline and serotonin, which play an important role in higher animals, are similar to alkaloids in their structure and biosynthesis and are sometimes called alkaloids.[159]
Alkaloid
12
Extraction
Because of the structural diversity of alkaloids, there is no single method of their extraction from natural raw materials.[160] Most methods exploit the property of most alkaloids to be soluble in organic solvents but not in water, and the opposite tendency of their salts. Most plants contain several alkaloids. Their mixture is extracted first and then individual alkaloids are separated.[161] Plants are thoroughly ground before extraction.[160][162] Most alkaloids are present in the raw plants in the form of salts of organic acids.[160] The extracted alkaloids Crystals of piperine extracted from black pepper. may remain salts or change into bases.[161] Base extraction is achieved by processing the raw material with alkaline solutions and extracting the alkaloid bases with organic solvents, such as 1,2-dichloroethane, chloroform, diethyl ether or benzene. Then, the impurities are dissolved by weak acids; this converts alkaloid bases into salts that are washed away with water. If necessary, an aqueous solution of alkaloid salts is again made alkaline and treated with an organic solvent. The process is repeated until the desired purity is achieved. In the acidic extraction, the raw plant material is processed by a weak acidic solution (e.g., acetic acid in water, ethanol, or methanol). A base is then added to convert alkaloids to basic forms that are extracted with organic solvent (if the extraction was performed with alcohol, it is removed first, and the remainder is dissolved in water). The solution is purified as described above.[160][163] Alkaloids are separated from their mixture using their different solubility in certain solvents and different reactivity with certain reagents or by distillation.[164]
Biosynthesis
Biological precursors of most alkaloids are amino acids, such as ornithine, lysine, phenylalanine, tyrosine, tryptophan, histidine, aspartic acid, and anthranilic acid.[165] Nicotinic acid can be synthesized from tryptophan or aspartic acid. Ways of alkaloid biosynthesis are too numerous and cannot be easily classified.[74] However, there are a few typical reactions involved in the biosynthesis of various classes of alkaloids, including synthesis of Schiff bases and Mannich reaction.[165]
In the biosynthesis of alkaloids, such reactions may take place within a molecule,[165] such as in the synthesis of piperidine:[30]
Alkaloid
13
Mannich reaction
An integral component of the Mannich reaction, in addition to an amine and a carbonyl compound, is a carbanion, which plays the role of the nucleophile in the nucleophilic addition to the ion formed by the reaction of the amine and the carbonyl.[167]
Alkaloid
14
Dimer alkaloids
In addition to the described above monomeric alkaloids, there are also dimeric, and even trimeric and tetrameric alkaloids formed upon condensation of two, three, and four monomeric alkaloids. Dimeric alkaloids are usually formed from monomers of the same type through the following mechanisms:[170] Mannich reaction, resulting in, e.g., voacamine Michael reaction (villalstonine) Condensation of aldehydes with amines (toxiferine) Oxidative addition of phenols (dauricine, tubocurarine) Lactonization (carpaine).
Voacamine
Villalstonine
Toxiferine
Dauricine
Tubocurarine
Carpaine
Alkaloid
15
Applications
In medicine
Medical use of alkaloid-containing plants has a long history, and, thus, when the first alkaloids were isolated in the 19th century, they immediately found application in clinical practice.[174] Many alkaloids are still used in medicine, usually in the form of salts, including the following:[8][175]:
Alkaloid Ajmaline antiarrhythmic Action
Atropine, scopolamine, hyoscyamine anticholinergic Vinblastine, vincristine Vincamine Codeine Cocaine Colchicine Morphine Reserpine Tubocurarine Physostigmine Quinidine Quinine Emetine Ergot alkaloids antitumor vasodilating, antihypertensive cough medicine anesthetic remedy for gout analgesic antihypertensive Muscle relaxant inhibitor of acetylcholinesterase antiarrhythmic antipyretics, antimalarial antiprotozoal agent sympathomimetic, vasodilator, antihypertensive
Many synthetic and semisynthetic drugs are structural modifications of the alkaloids, which were designed to enhance or change the primary effect of the drug and reduce unwanted side-effects.[176] For example, naloxone, an opioid receptor antagonist, is a derivative of thebaine that is present in opium.[177]
Thebaine
Naloxone
Alkaloid
16
In agriculture
Prior to the development of a wide range of relatively low-toxic synthetic pesticides, some alkaloids, such as salts of nicotine and anabasine, were used as insecticides. Their use was limited by their high toxicity to humans.[178]
Notes
[1] Andreas Luch (2009). Molecular, clinical and environmental toxicology (http:/ / books. google. com/ ?id=MtOiLVWBn8cC& pg=PA20). Springer. p.20. ISBN3-7643-8335-6. . [2] IUPAC. Compendium of Chemical Terminology (http:/ / goldbook. iupac. org/ A00220. html), 2nd ed. (The "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997) ISBN 0-9678550-9-8 doi:10.1351/goldbook [3] R. H. F. Manske. The Alkaloids. Chemistry and Physiology. Volume VIII. New York: Academic Press, 1965, p. 673 [4] Robert Alan Lewis. Lewis' dictionary of toxicology (http:/ / books. google. com/ books?id=caTqdbD7j4AC& pg=PA51). CRC Press, 1998, p. 51 ISBN 1-56670-223-2 [5] Chemical Encyclopedia: alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 119. html) [6] "Alkaloid" (http:/ / science. howstuffworks. com/ alkaloid-info. htm). . [7] Rhoades, David F (1979). "Evolution of Plant Chemical Defense against Herbivores". In Rosenthal, Gerald A., and Janzen, Daniel H. Herbivores: Their Interaction with Secondary Plant Metabolites. New York: Academic Press. p.41. ISBN0-12-597180-X. [8] Robert A. Meyers Encyclopedia of Physical Science and Technology Alkaloids, 3rd edition. ISBN 0-12-227411-3 [9] Leland J. Cseke Natural Products from Plants (http:/ / books. google. com/ books?id=wV2T41nGFc4C& pg=PA30) Second Edition. CRC, 2006, p. 30 ISBN 0-8493-2976-0 [10] A. William Johnson Invitation to Organic Chemistry (http:/ / books. google. com/ books?id=0X4cQus2gz8C& pg=PA433), Jones and Bartlett, 1999, p. 433 ISBN 0-7637-0432-6 [11] Raj K Bansal A Text Book of Organic Chemistry (http:/ / books. google. com/ books?id=1B6ijcTkD5EC& pg=PA644). 4th Edition, New Age International, 2004, p. 644 ISBN 81-224-1459-1 [12] Aniszewski, p. 110 [13] Biographical information about German pharmacist Carl Friedrich Wilhelm Meiner (17921853) is available in the German Wikipedia: http:/ / de. wikipedia. org/ wiki/ Carl_Friedrich_Wilhelm_Mei%C3%9Fner (in German). [14] In the penultimate sentence of his article [W. Meissner (1819) "ber Pflanzenalkalien: II. ber ein neues Pflanzenalkali (Alkaloid)" (On plant alkalis: II. On a new plant alkali (alkaloid)), Journal fr Chemie und Physik, vol. 25, pp. 377381] Meissner wrote "berhaupt scheint es mir auch angemessen, die bis jetzt bekannten Pflanzenstoffe nicht mit dem Namen Alkalien, sondern Alkaloide zu belegen, da sie doch in manchen Eigenschaften von den Alkalien sehr abweichen, sie wrden daher in dem Abschnitt der Pflanzenchemie vor den Pflanzensuren ihre Stelle finden." (In general, it seems appropriate to me to impose on the known plant substances not the name "alkalis" but "alkaloids", since they differ greatly in some properties from the alkalis; among the chapters of plant chemistry, they would therefore find their place before plant acids [since "Alkaloid" would precede "Sure" (acid)].) [15] Hesse, pp. 13 [16] Hesse, p. 5 [17] The suffix "ine" is a Greek feminine patronymic suffix and means "daughter of"; hence, for example, "atropine" means "daughter of Atropa (belladonna)". (https:/ / webspace. yale. edu/ chem125/ 125/ history99/ 5Valence/ Nomenclature/ alkanenames. html) [18] Hesse, p. 7 [19] Aniszewski, p. 182 [20] Hesse, p. 338 [21] Hesse, p. 304 [22] Hesse, p. 350 [23] Hesse, pp. 313316 [24] TSB: Coniine (http:/ / slovari. yandex. ru/ dict/ bse/ article/ 00036/ 77600. htm) [25] Hesse, p. 204
Alkaloid
[26] Begley, Natural Products in Plants [27] Hesse, p. 11 [28] Orekhov, p. 6 [29] Aniszewski, p. 109 [30] Dewick, p. 307 [31] Hesse, p. 12 [32] Plemenkov, p. 223 [33] Aniszewski, p. 108 [34] Hesse, p. 84 [35] Hesse, p. 31 [36] Dewick, p. 381 [37] Dimitris C. Gournelif, Gregory G. Laskarisb and Robert Verpoorte (1997). "Cyclopeptide alkaloids". Nat. Prod. Rep. 14 (1): 7582. doi:10.1039/NP9971400075. PMID9121730. [38] Aniszewski, p. 11 [39] Plemenkov, p. 246 [40] Aniszewski, p. 12 [41] Dewick, p. 382 [42] Hesse, pp. 44, 53 [43] Plemenkov, p. 224 [44] Aniszewski, p. 75 [45] Orekhov, p. 33 [46] Chemical Encyclopedia: Tropan alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 4609. html) [47] Hesse, p. 34 [48] Aniszewski, p. 27 [49] Chemical Encyclopedia: Pyrrolizidine alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 3370. html) [50] Plemenkov, p. 229 [51] Blankenship JD, Houseknecht JB, Pal S, Bush LP, Grossman RB, Schardl CL (2005). "Biosynthetic precursors of fungal pyrrolizidines, the loline alkaloids". Chembiochem 6 (6): 10161022. doi:10.1002/cbic.200400327. PMID15861432. [52] Faulkner JR, Hussaini SR, Blankenship JD, Pal S, Branan BM, Grossman RB, Schardl CL (2006). "On the sequence of bond formation in loline alkaloid biosynthesis". Chembiochem 7 (7): 10781088. doi:10.1002/cbic.200600066. PMID16755627. [53] Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP (2007). "Loline alkaloids: currencies of mutualism". Phytochemistry 68 (7): 980996. doi:10.1016/j.phytochem.2007.01.010. PMID17346759. [54] Plemenkov, p. 225 [55] Aniszewski, p. 95 [56] Orekhov, p. 80 [57] Chemical Encyclopedia: Quinolizidine alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 5011. html) [58] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. London: The Chemical Society, 1971, p. 93 [59] Aniszewski, p. 98 [60] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. London: The Chemical Society, 1971, p. 91 [61] Joseph P. Michael (2002). "Indolizidine and quinolizidine alkaloids". Nat. Prod. Rep 19: 458475. doi:10.1039/b208137g. [62] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. London: The Chemical Society, 1971, p. 92 [63] Dewick, p. 310 [64] Aniszewski, p. 96 [65] Aniszewski, p. 97 [66] Plemenkov, p. 227 [67] Chemical Encyclopedia: pyridine alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 3336. html) [68] Aniszewski, p. 107 [69] Aniszewski, p. 85 [70] Plemenkov, p. 228 [71] Hesse, p. 36 [72] Chemical Encyclopedia: isoquinoline alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 1642. html) [73] Aniszewski, pp. 7778 [74] Begley, Alkaloid Biosynthesis [75] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. London: The Chemical Society, 1973, p. 122 [76] Hesse, p. 54 [77] Hesse, p. 37 [78] Hesse, p. 38 [79] Hesse, p. 46 [80] Hesse, p. 50
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Alkaloid
[81] Kenneth W. Bentley (1997). "-Phenylethylamines and the isoquinoline alkaloids". Nat. Prod. Rep 14 (4): 387411. doi:10.1039/NP9971400387. PMID9281839. [82] Hesse, p. 47 [83] Hesse, p. 39 [84] Hesse, p. 41 [85] Hesse, p. 49 [86] Hesse, p. 44 [87] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. London: The Chemical Society, 1973, p. 164 [88] Hesse, p. 51 [89] Plemenkov, p. 236 [90] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. London: The Chemical Society, 1973, p. 163 [91] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 3. London: The Chemical Society, 1973, p. 168 [92] Hesse, p. 52 [93] Hesse, p. 53 [94] Plemenkov, p. 241 [95] Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. Academic Press, 1989, p. 261 [96] Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 35. Academic Press, 1989, pp. 260263 [97] Plemenkov, p. 242 [98] Begley, Cofactor Biosynthesis [99] John R. Lewis (2000). "Amaryllidaceae, muscarine, imidazole, oxazole, thiazole and peptide alkaloids, and other miscellaneous alkaloids" (http:/ / www. rsc. org/ publishing/ journals/ NP/ article. asp?doi=a809403i). Nat. Prod. Rep 17 (1): 5784. doi:10.1039/a809403i. PMID10714899. . [100] Chemical Encyclopedia: Quinazoline alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 5003. html) [101] Aniszewski, p. 106 [102] Aniszewski, p. 105 [103] Richard B. Herbert; Herbert, Richard B.; Herbert, Richard B. (1999). "The biosynthesis of plant alkaloids and nitrogenous microbial metabolites" (http:/ / www. rsc. org/ publishing/ journals/ NP/ article. asp?doi=a705734b). Nat. Prod. Rep 16: 199208. doi:10.1039/a705734b. . [104] Plemenkov, pp. 231, 246 [105] Hesse, p. 58 [106] Plemenkov, p. 231 [107] Chemical Encyclopedia: Quinoline alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 5014. html) [108] Aniszewski, p. 114 [109] Orekhov, p. 205 [110] Hesse, p. 55 [111] Plemenkov, p. 232 [112] Orekhov, p. 212 [113] Aniszewski, p. 118 [114] Aniszewski, p. 112 [115] Aniszewski, p. 113 [116] Hesse, p. 15 [117] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. London: The Chemical Society, 1971, p. 467 [118] Dewick, p. 349-350 [119] Aniszewski, p. 119 [120] Hesse, p. 29 [121] Hesse, pp. 2326 [122] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 1. London: The Chemical Society, 1971, p. 169 [123] J. E. Saxton The Alkaloids. A Specialist Periodical Report. Volume 5. London: The Chemical Society, 1975, p. 210 [124] Hesse, pp. 1718 [125] Dewick, p. 357 [126] Aniszewski, p. 104 [127] Hesse, p. 72 [128] Hesse, p. 73 [129] Dewick, p. 396 [130] PlantCyc Pathway: ephedrine biosynthesis (http:/ / www. plantcyc. org:1555/ PLANT/ NEW-IMAGE?type=NIL& object=PWY-5883) [131] Hesse, p. 76 [132] Chemical Encyclopedia: colchicine alkaloids (http:/ / www. xumuk. ru/ encyklopedia/ 2069. html) [133] Aniszewski, p. 77 [134] Hesse, p. 81
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[135] Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. Academic Press, 1984, p. 376 [136] Hesse, p. 77 [137] Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. Academic Press, 1984, p. 268 [138] Arnold Brossi The Alkaloids: Chemistry and Pharmacology, Volume 23. Academic Press, 1984, p. 231 [139] Hesse, p. 82 [140] Spermine Biosynthesis (http:/ / www. chem. qmul. ac. uk/ iubmb/ enzyme/ reaction/ misc/ spermine. html) [141] Plemenkov, p. 243 [142] Chemical Encyclopedia: Terpenes (http:/ / www. xumuk. ru/ encyklopedia/ 2/ 4392. html) [143] Begley, Natural Products: An Overview [144] Atta-ur-Rahman and M. Iqbal Choudhary (1997). "Diterpenoid and steroidal alkaloids" (http:/ / www. rsc. org/ publishing/ journals/ NP/ article. asp?doi=NP9971400191). Nat. Prod. Rep 14 (2): 191203. doi:10.1039/np9971400191. PMID9149410. . [145] Hesse, p. 88 [146] Dewick, p. 388 [147] Plemenkov, p. 247 [148] TSB: Nicotine (http:/ / slovari. yandex. ru/ dict/ bse/ article/ 00052/ 84600. htm) [149] Grinkevich, p. 131 [150] G. A. Spiller Caffeine (http:/ / books. google. com/ books?id=Rgs_rVOceZwC& pg=PA140), CRC Press, 1997 ISBN 0-8493-2647-8 [151] Fattorusso, p. 53 [152] Thomas Acamovic, Colin S. Stewart, T. W. Pennycott (2004). Poisonous plants and related toxins, Volume 2001 (http:/ / books. google. com/ ?id=nixyqfGIGHcC& pg=PA362). CABI. p.362. ISBN0-85199-614-0. . [153] Aniszewski, p. 13 [154] Orekhov, p. 11 [155] Hesse, p.4 [156] Grinkevich, pp. 122123 [157] Orekhov, p. 12 [158] Fattorusso, p. XVII [159] Aniszewski, pp. 110111 [160] Hesse, p. 116 [161] Grinkevich, p. 132 [162] Grinkevich, p. 5 [163] Grinkevich, pp. 132134 [164] Grinkevich, pp. 134136 [165] Plemenkov, p. 253 [166] Plemenkov, p. 254 [167] Dewick, p. 19 [168] Plemenkov, p. 255 [169] Dewick, p. 305 [170] Hesse, pp. 91105 [171] Aniszewski, p. 142 [172] Hesse, pp. 283291 [173] Aniszewski, pp. 142143 [174] Hesse, p. 303 [175] Hesse, pp. 303309 [176] Hesse, p. 309 [177] Dewick, p. 335 [178] Gyrgy Matolcsy, Mikls Ndasy, Viktor Andriska Pesticide chemistry (http:/ / books. google. com/ books?id=fPiRSsUOpLEC& pg=PA21), Elsevier, 2002, pp. 2122 ISBN 0-444-98903-X [179] Veselovskaya, p. 75 [180] Hesse, p. 79 [181] Veselovskaya, p. 136 [182] Geoffrey A. Cordell The Alkaloids: Chemistry and Biology. Volume 56, Elsevier, 2001, p. 8 [183] Veselovskaya, p. 6 [184] Veselovskaya, pp. 5152
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References Bibliography
Aniszewski, Tadeusz (2007). Alkaloids secrets of life. Amsterdam: Elsevier. ISBN978-0-444-52736-3. Begley, Tadhg P. (2009). Encyclopedia of Chemical Biology. Wiley. doi:10.1002/cbic.200900262. ISBN978-0-471-75477-0. Dewick, Paul M (2002). Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. ISBN0-471-49640-5. Fattorusso, E. and Taglialatela-Scafati, O. (2008). Modern Alkaloids: Structure, Isolation, Synthesis and Biology. Wiley-VCH. ISBN978-3-527-31521-5. Grinkevich NI Safronich LN (1983). The chemical analysis of medicinal plants: Proc. allowance for pharmaceutical universities. M. Hesse, Manfred (2002). Alkaloids: Nature's Curse or Blessing?. Wiley-VCH. ISBN978-3-906390-24-6. Knunyants, IL (1988). Chemical Encyclopedia (http://www.cnshb.ru/AKDiL/0048/base/RA/140004.shtm). Soviet Encyclopedia. Orekhov, AP (1955). Chemistry alkaloids (Acad. 2 ed.). M.: USSR. Plemenkov, VV (2001). Introduction to the Chemistry of Natural Compounds. Kazan. Veselovskaya, N. B., Kovalenko, A.E Drugs, M.: Triada-X, 2000
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