alkaloid

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Related to Vinca alkaloids: vinblastine, vincristine, paclitaxel, Taxanes

alkaloid

alkaloid, any of a class of organic compounds composed of carbon, hydrogen, nitrogen, and usually oxygen that are often derived from plants. Although the name means alkalilike, some alkaloids do not exhibit alkaline properties. Many alkaloids, though poisons, have physiological effects that render them valuable as medicines. For example, curarine, found in the deadly extract curare, is a powerful muscle relaxant; atropine is used to dilate the pupils of the eyes; and physostigmine is a specific for certain muscular diseases. Narcotic alkaloids used in medicine include morphine and codeine for the relief of pain and cocaine as a local anesthetic. Other common alkaloids include quinine, caffeine, nicotine, strychnine, serotonin, and LSD. Aconitine is the alkaloid of aconite. Cinchonine and quinine are derived from cinchona, coniine is found in poison hemlock, and reserpine is an extract of rauwolfia roots. Emetine is an alkaloid of ipecac.
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Alkaloid

A cyclic organic compound that contains nitrogen in a negative oxidation state and is of limited distribution among living organisms. Over 10,000 alkaloids of many different structural types are known; and no other class of natural products possesses such an enormous variety of structures. Therefore, alkaloids are difficult to differentiate from other types of organic nitrogen-containing compounds.

Simple low-molecular-weight derivatives of ammonia, as well as polyamines and acyclic amides, are not considered alkaloids because they lack a cyclic structure in some part of the molecule. Amines, amine oxides, amides, and quaternary ammonium salts are included in the alkaloid group because their nitrogen is in a negative oxidation state (the oxidation state designates the positive or negative character of atoms in a molecule). Nitro and nitroso compounds are excluded as alkaloids. The almost-ubiquitous nitrogenous compounds, such as amino acids, amino sugars, peptides, proteins, nucleic acids, nucleotides, prophyrins, and vitamins, are not alkaloids. However, compounds that are exceptions to the classical-type definition (that is, a compound containing nitrogen, usually a cyclic amine, and occurring as a secondary metabolite), such as neutral alkaloids (colchicine, piperine), the β-phenyl-ethylanines, and the purine bases (caffeine, theophylline, theobromine), are accepted as alkaloids.

Alkaloids often occur as salts of plant acids such as malic, meconic, and quinic acids. Some plant alkaloids are combined with sugars, for example, solanine in potato (Solanum tuberosum) and tomatine in tomato (Lycopersicum esculentum). Others occur as amides, for example, piperine from black pepper (Piper nigrum), or as esters, for example, cocaine from coca leaves (Erythroxylum coca). Still other alkaloids occur as quaternary salts or tertiary amine oxides.

While most alkaloids have been isolated from plants, a large number have been isolated from animal sources. They occur in mammals, anurans (frogs, toads), salamanders, arthropods (ants, millipedes, ladybugs, beetles, butterflies), marine organisms, mosses, fungi, and certain bacteria.

Many alkaloids exhibit marked pharmacological activity, and some find important uses in medicine. Atropine, the optically inactive form of hyoscyamine, is used widely in medicine as an antidote to cholinesterase inhibitors such as physostigmine and insecticides of the organophosphate type; it is also used in drying cough secretions. Morphine and codeine are narcotic analgesics, and codeine is also an antitussive agent, less toxic and less habit-forming than morphine. Colchicine, from the corms and seeds of the autumn crocus, is used as a gout suppressant. Caffeine, which occurs in coffee, tea, cocoa, and cola, is a central nervous system stimulant; it is used as a cardiac and respiratory stimulant and as an antidote to barbiturate and morphine poisoning. Emetine, the key alkaloid of ipecac root (Cephaelis ipecacuanha), is used in the treatment of amebic dysentery and other protozoal infections.

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Epinephrine or adrenaline (see structure), produced in most animal species by the adrenal medulla, is used as a bronchodilator and cardiac stimulant and to counter allergic reactions, anesthesia, and cardiac arrest. See Epinephrine

McGraw-Hill Concise Encyclopedia of Bioscience. © 2002 by The McGraw-Hill Companies, Inc.

alkaloid

[′al·kə‚lȯid]
(organic chemistry)
One of a group of nitrogenous bases of plant origin, such as nicotine, cocaine, and morphine.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.

alkaloid

any of a group of nitrogenous basic compounds found in plants, typically insoluble in water and physiologically active. Common examples are morphine, strychnine, quinine, nicotine, and caffeine
Collins Discovery Encyclopedia, 1st edition © HarperCollins Publishers 2005
References in periodicals archive ?
A wide range of lipophilic chemotherapeutic agents, such as anthracenes, anthracyclines, epipodophyllotoxins, taxanes and vinca alkaloids, which can enter tumor cells by free diffusion, are substrates of P-gp and can be expelled by the transporter (Loo and Clarke 2005).
The chemotherapeutic agents most often associated with CIPN are platinum compounds, taxanes, vinca alkaloids, thalidomide, and bortezomib.
Detoxication of vinca alkaloids by human P450CYP3A4-mediated metabolism: implications for the development of drug resistance.
The Vinca alkaloids: from biosynthesis and accumulation in plant cells, to uptake, activity and metabolism in animal cellsIn: Atta-ur-Rahman (Ed.).
Meanwhile, TCC cells show resistance to Vinca alkaloids such as vincristine (Nishiyama et al., 1993; Yu et al., 1998).
It has been demonstrated that cnidiadin, a furano-coumarin found in certain traditional Chinese medications, inhibits P-gp transport and reverses the resistance of multiresistant cells overexpressing P-gp, to Vinca alkaloids (Barthomeuf et al., 2006).
P-gp is a broad-spectrum transporter, which can expel different classes of cytotoxic agents, such as Vinca alkaloids, taxanes, anthracyclines, colchicine, etc.
Vinca alkaloids are used to treat pediatric leukemia and other neoplasms today.
The vinca alkaloids are the most well known compounds of this class that are presently used in the clinics.