Alkaloids purines

Thin-layer chromatography of antibiotics, drugs, alkaloids, purines, pyrimidines, nucleic acids, toxins, and vitamins 98AC7R. 

The Coffee (syn. 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 (o-ribose or 2 deoxy-D-ribose). Typical purine alkaloids are caffeine, theophylline and theobromine. The same or similar purine alkaloids occur also in other plant families. 

Keywords alkaloid biosynthesis alkaloid genes nicotine tropane alkaloids pyrrolizidine alkaloids benzylisoquinoline alkaloids monoterpene indole alkaloids ergot alkaloids acridone alkaloids purine alkaloids taxol betalains... 

Biologic Background Isoquinoline Alkaloids Terpenoid Indole Alkaloids Tropane Alkaloids Purine Alkaloids... 

Adenine/guanine Purine alkaloids Purine Caffeine Theacrine Theobromine Theophylline... 

Other Sources of Imidazole Alkaloids Lythraceae alkaloids Maytansinoids Antitumor Activity Other Biological Activity Muscarine Alkaloids Naphthylisoquinoline Alkaloids Peptide Alkaloids Purine or Xanthine Alkaloids Biosynthesis... 

Purine alkaloids Purines Coffee, tea, cocoa Coffeine, theobromine, theophylline... 

Alkaloids derived from purine (10-36) and purine oxidation product xanthine (10-37), respectively, are called purine alkaloids. Purine alkaloids are the most widespread alkaloids in foods. 

Ai,A/-bis(hydroxymethyl) formamide [6921-98-8] (21), which in solution is in equiUbrium with the monomethylol derivative [13052-19-2] and formaldehyde. With ben2aldehyde in the presence of pyridine, formamide condenses to yield ben2yhdene bisformamide [14328-12-2]. Similar reactions occur with ketones, which, however, requite more drastic reaction conditions. Formamide is a valuable reagent in the synthesis of heterocycHc compounds. Synthetic routes to various types of compounds like imida2oles, oxa2oles, pyrimidines, tria2ines, xanthines, and even complex purine alkaloids, eg, theophylline [58-55-9] theobromine [83-67-0], and caffeine [58-08-2], have been devised (22). 

Astcracantha longifolia Ness (Aeanthacese). This plant, formerly named Hygrophila spinosa, contains an alkaloid, C10H12O3N4, m.p. 216-7°, which forms an oxalate, m.p. 221-2°, and a sulphate, m.p. 210-1°, and may be a purine derivative (Basu and Lai, Qtiart. J. Pharmacol., 1947, 20, 38). 

It would not be too far fetched to state that life on this planet is totally dependent on two compounds based on the purine nucleus. Two of the bases crucial to the function of DNA and flNA—guanine and adenine—are in fact substituted purines. It is thus paradoxical that the lead for the development of medicinal agents based on this nucleus actually came from observations of the biologic activity of plant alkaloids containing that heterocyclic system, rather than from basic biochemistry. 

This series in heterocychc chemistry is being introduced to collectively make available critically and comprehensively reviewed hterature scattered in various journals as papers and review articles. All sorts of heterocyclic compounds originating from synthesis, natural products, marine products, insects, etc. will be covered. Several heterocyclic compounds play a significant role in maintaining life. Blood constituents hemoglobin and purines, as well as pyrimidines, are constituents of nucleic acid (DNA and RNA). Several amino acids, carbohydrates, vitamins, alkaloids, antibiotics, etc. are also heterocyclic compounds that are essential for life. Heterocyclic compounds are widely used in clinical practice as drugs, but all applications of heterocyclic medicines can not be discussed in detail. In addition to such applications, heterocyclic compounds also find several applications in the plastics industry, in photography as sensitizers and developers, and the in dye industry as dyes, etc. 

Steroids, e.g. cholesterol, triolein, androsterone sugars, e.g. fructose, glucose, ribose amino acids, pyrimidines, purines, alkaloids 110-150°C, 2-12 h Conversion to fluorescent derivatives by heating. [5]... 

Prostaglandins 195—197, 242 — 244, 273, 274,376, 411,413, 430, 438 Protocol form example 133 Prunasin 179,181 Psychopharmaceuticals 364 Purines 44, 266, 438, 439 Pyrazolidine derivatives 426 Pyrethroid insecticides 359 Pyridine alkaloids 66 4-Pyridinecarboxylic acid hydrazide reagent 318... 

Aph, flos-aquae Strain NH-1 NH-5 (U.S., New Hampshire) Aphantoxin (neosaxitoxin) Aphantoxin II (saxitoxin) Purine alkaloid MW 315 (neoSTX) MW 299 (STX) 10... 

Purine is the parent heterocyclic compound of the methylxanthines, which are often referred to as the purine alkaloids.1-7 Purine is also the parent compound of some of the base constituents of the nucleotides, which in turn are part of the nucleic acids RNA and DNA. Thus, it appears that the purine alkaloids have similar precursors to nucleic acids. 

Suzuki, T., Ashihara, H., Waller G.R.., Purine and purine alkaloid metabolism in Camellia and Coffea plant, Phytochemistry, 31,2575,1992... 

Prenosil, J.E., Hegglin, M., Baumann, T.W., Frischkneechtt, P.M., Kappeler, A.W., Brodeliuss.P.. and Haldimann,D., Purine alkaloid producing cell cultures fundamental aspects and possible applications in biotechnology, Enzyme Microbial. Technol., 9,450,1987. 

Foods derived from cocoa beans have been consumed by humans since at least 460 to 480 AD. The source of cocoa beans, the species Theobroma, contains a variety of biologically active components. These include the purine alkaloids theobromine, caffeine, and theophylline. Structurally, they are methylated xanthines and, thus, are often referred to as methylxanthines. Theobromine (3, 7-dimethylxanthine) is the predominant purine alkaloid in cocoa and chocolate. Caffeine (1, 3, 7-trimethylxanthine), the major purine alkaloid found in coffee and tea, is found in cocoa and chocolate at about one eighth the concentration of theobromine. Only trace amounts of theophylline (1, 3-dimethylxanthine) are detected in cocoa and chocolate products. 

With the death of the bean, cellular structure is lost, allowing the mixing of water-soluble components that normally would not come into contact with each other. The complex chemistry that occurs during fermentation is not fully understood, but certain cocoa enzymes such as glycosidase, protease, and polyphenol oxidase are active. In general, proteins are hydrolyzed to smaller proteins and amino acids, complex glycosides are split, polyphenols are partially transformed, sugars are hydrolyzed, volatile acids are formed, and purine alkaloids diffuse into the bean shell. The chemical composition of both unfermented and fermented cocoa beans is compared in Table 1. 

Marx, F., Maia, J. G. S., Purine alkaloids in seeds of Theobroma species from the Amazon, Z. Lebensm. Unters. Forsch., 193, 460, 1991. 

Timbie, D., Studies on the protein and purine alkaloids of cocoa beans, Ph.D. thesis, The Pennsylvania State University, 1977. 

Saldana MDA, Mazzafera P and Mohamed RS. 1999. Extraction of purine alkaloids from mate (Ilex paraguariensis) using supercritical CO2. J Agric Food Chem 47 3804-3808. 

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