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From Wikipedia, the free encyclopedia
This article is about the chemical compounds alkaloids. For the pharmaceutical company in the Republic of Macedonia, see Alkaloid (company).
Alkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. 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 secondary metabolites). Many alkaloids can be purified 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 stimulant caffeine, nicotine, the analgesic morphine, or the antimalarial drug quinine. Some alkaloids have a bitter taste.
Generally speaking, alkaloids are categorized under three main categories,depending on their biogenic origin. For those containing at least a nitrogen atom in a ring system derived from amino acids (i.e. alkaloids derived from phenylalanine are not grouped in this category), they are true alkaloids. The alkaloids derived from phenylalanine are categorized as protoalkaloids. While the remaining ones, such as steroidal alkaloids and purine alkaloids, are classified as pseudoalkaloids.
Alkaloids are usually classified by their common molecular precursors, based on the metabolic pathway used to construct the molecule. When not much was known about the biosynthesis of alkaloids, they were grouped under the names of known compounds, even some non-nitrogenous ones (since those molecules' structures appear in the finished product; the opium alkaloids are sometimes called "phenanthrenes", for example), or by the plants or animals they were isolated from. When more is learned about a certain alkaloid, the grouping is changed to reflect the new knowledge, usually taking the name of a biologically-important amine that stands out in the synthesis process.[original research?]
• Pyridine group: piperine, coniine, trigonelline, arecoline, arecaidine, guvacine, cytisine, lobeline, nicotine, anabasine, sparteine, pelletierine.
• Pyrrolidine group: hygrine, cuscohygrine, nicotine
• Tropane group: atropine, cocaine, ecgonine, scopolamine, catuabine
• Indolizidine group: senecionine, swainsonine
• Quinoline group: quinine, quinidine, dihydroquinine, dihydroquinidine, strychnine, brucine, veratrine, cevadine
• Isoquinoline group: opium alkaloids (papaverine, narcotine, narceine, morphine, codeine, heroine), sanguinarine, hydrastine, berberine, emetine, berbamine, oxyacanthine
• Phenanthrene alkaloids: opium alkaloids (morphine, codeine, thebaine)
• Phenethylamine group: mescaline, ephedrine, dopamine
• Indole group:
o Tryptamines: serotonin, DMT, 5-MeO-DMT, bufotenine, psilocybin
o Ergolines (the ergot alkaloids): ergine, ergotamine, lysergic acid
o Beta-carbolines: harmine, harmaline, tetrahydroharmine
o Yohimbans: reserpine, yohimbine
o Vinca alkaloids: vinblastine, vincristine
o Kratom (Mitragyna speciosa) alkaloids: mitragynine, 7-hydroxymitragynine
o Tabernanthe iboga alkaloids: ibogaine, voacangine, coronaridine
o Strychnos nux-vomica alkaloids: strychnine, brucine
• Purine group:
o Xanthines: caffeine, theobromine, theophylline
• Terpenoid group:
o Aconitum alkaloids: aconitine
o Steroid alkaloids (containing a steroid skeleton in a nitrogen containing structure):
Solanum (e.g. potato and tomato) alkaloids (solanidine, solanine, chaconine)
Veratrum alkaloids (veratramine, cyclopamine, cycloposine, jervine, muldamine)
Fire Salamander alkaloids (samandarin)
• Quaternary ammonium compounds: muscarine, choline, neurine
• Miscellaneous: capsaicin, cynarin, phytolaccine, phytolaccotoxin
Low-molecular weight alkaloids without hydrogen bond donors such as hydroxy groups are often liquid at room temperature, examples are nicotine, sparteine, coniine, and phenethylamine.
The basicity of alkaloids depends on the lone pairs of electrons on their nitrogen atoms. As organic bases, alkaloids form salts with mineral acids such as hydrochloric acid and sulfuric acid and organic acids such as tartaric acid or maleic acid. These salts are usually more water-soluble than their free base form.
1. ^ International Union of Pure and Applied Chemistry (1995). "alkaloids". Compendium of Chemical Terminology Internet edition.
2. ^ http://www.ansci.cornell.edu/plants/toxicagents/steroid.html,
From Wikipedia, the free encyclopedia
Secondary metabolites are organic compounds that are not directly involved in the normal growth, development, or reproduction of organisms. Unlike primary metabolites, absence of secondary metabolities does not result in immediate death, but rather in long-term impairment of the organism's survivability, fecundity, or aesthetics, or perhaps in no significant change at all. Secondary metabolites are often restricted to a narrow set of species within a phylogenetic group.
• 1 Categories
o 1.1 Small "small molecules"
o 1.2 Big "small molecules", produced by large, modular, "molecular factories"
o 1.3 Non-"small molecules" - DNA, RNA, ribosome, or polysaccharide "classical" biopolymers
• 2 See also
• 3 References
Most of the secondary metabolites of interest to humankind fit into categories which classify secondary metabolites based on their biosynthetic origin. Since secondary metabolites are often created by modified primary metabolite synthases, or "borrow" substrates of primary metabolite origin, these categories should not be interpreted as saying that all molecules in the category are secondary metabolites (for example the steroid category), but rather that there are secondary metabolites in these categories.
Small "small molecules"
• Alkaloids (usually a small, heavily derivatized amino acid):
o Hyoscyamine, present in Datura stramonium
o Atropine, present in Atropa belladonna, Deadly nightshade
o Cocaine, present in Erythroxylon coca the Coca plant
o Codeine and Morphine, present in Papaver somniferum, the opium poppy
o Tetrodotoxin, a microbial product in Fugu and some salamanders
o Vincristine & Vinblastine, mitotic inhibitors found in the Rosy Periwinkle
• Terpenoids (come from semiterpene oligomerization):
o Azadirachtin, (Neem tree)
o Artemisinin, present in Artemisia annua Chinese wormwood
o tetrahydrocannabinol, present in cannabis sativa
o Steroids (Terpenes with a particular ring structure)
Saponins (plant steroids, often glycosylated)
• Glycosides (heavily modified sugar molecules):
o Phenazine-1-carboxylic acid (and derivatives)
Big "small molecules", produced by large, modular, "molecular factories"
• Fatty acid synthase products :
• Nonribosomal peptides:
• Hybrids of the above three:
Non-"small molecules" - DNA, RNA, ribosome, or polysaccharide "classical" biopolymers
• Ribosomal peptides:
1. ^ "Chemical plants". http://www.open2.net/sciencetechnologynature/worldaroundus/chemicalplants.html. Retrieved on 2008-12-19.
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