Theobromine structure

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. 

Darenthin, molecular formula and structure, 5 96t Dark chocolate, 6 361 minerals content, 6 371t theobromine and caffeine content, 6 367t tocopherols, 6 370t typical formulation, 6 362t Dark conductivity ( D), of a-Si H, 22 ... 

Phenethylamine is structurally related to a number of psychedelics, including mescaline. It also occurs in chocolate and is thought to be one of the substances responsible for the feel good effect of chocolate (other molecules contribute as well, including theobromine). Chocoholics will understand. 

After the nucleic acid purines adenine and guanine, the next most prominent purine in our everyday lives is probably caffeine. Caffeine, in the form of beverages such as tea, coffee, and cola, is one of the most widely consumed and socially accepted natural stimulants. Closely related structurally are theobromine and theophylline. Theobromine is a major constituent of cocoa, and related chocolate products. Caffeine is also used medicinally,... 

Although far less numerous than the terpenoid/isoprenoid or polyketide NPs, the alkaloids (with an estimated 20,000 different structures) have a special place in NP research because a few are of great value to humans—for example, morphine, theobromine, caffeine, vincristine, quinine, codeine, cocaine, nicotine and strychnine. These often complex chemicals are found in about 20% of vascular plants and a smaller number of fungi, marine invertebrates and a few bacteria. ... 

The major bases found in nucleic acids are adenine and guanine (purines) and uracil, cytosine, and thymine (pyrimidines). Thymine is found primarily in DNA, uracil in RNA, and the others in both DNA and RNA. Their structures, along with their chemical parent compounds, purine and pyrimidine, are shown in Figure 10.1, which also indicates other biologically important purines that are not components of nucleic acids. Hypoxanthine, orotic acid, and xanthine are biosynthetic and/or degradation intermediates of purine and pyrimidine bases, whereas xanthine derivatives—caffeine, theophylline, and theobromine—are alkaloids from plant sources. Caffeine is a component of coffee beans and tea, and its effects on metabolism are mentioned in Chapter 16. Theophylline is found in tea and is used therapeutically in asthma, because it is a smooth muscle relaxant. Theobromine is found in chocolate. It is a diuretic, heart stimulant, and vasodilator. 

Figure 16-1. Molecular structures of caffeine (left), theophylline (center), and theobromine (right)...

The prototypical structural class of nonselective PDE inhibitors is represented by the methylxanthines (Figure 9.4), a family of plant-derived alkaloids that includes theophylline (1), caffeine (2), and theobromine (3) [9], Although limited in potency, these simple naturally occurring xanthines were the parents in the later discoveries of more potent synthetic derivatives such as pentoxyfylline (4) and isobutylmethyl-xanthine (IBMX, 5). In particular, the latter compound has been widely used and has been regarded for decades as the gold standard nonselective inhibitor of all PDEs. Only recently has it become clear that some of the newer PDEs (8 and 9) are not inhibited by IBMX. Derivatives of IBMX carrying substituents at the 8 position confer increased potency [10], An example is compound 6, which retains most of... 

Coffee and tea plants seem to contain a variety of N-methyltransferase enzymes that have varying substrate specificity (168, 169). For example, a caffeine synthase enzyme isolated from tea leaves catalyzes both the N-methylation of N-methylxanthine and theobromine (176). The substrate specificity of the methyltransferases can be changed by site-directed mutagenesis (177), and the crystal structure of two of the N-methyltransferases has been reported recently (178). 

N.m.r. spectra of xanthine, theobromine, theophylline, caffeine, and their conjugate acids have been analysed. The AT-ray crystal structure of (theobromine)2 H2I8 shows it to be a polyiodide salt with alternating cationic (H-bonded protonated theobromines) and anionic (Iti ions) layers. ... 

One of a number of basic compounds found in living matter and having a purine-type molecular structure. See adenine base pair guanine hypoxanthine xanthine uric acid caffeine theobromine. 

Fig. 5. Chemical structures of naturally occurring PDE inhibitors highlighting the pyrimidinone heterocycle as a naturally occurring pharmacophore for PDE inhibition, (a) Caffeine (1,3,7-trimethylpurine-2,6-dione). (b) Theophylline (1,3-dimethyl-7H-purine-2,6-dione). (c) Theobromine (3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione). (d) IBMX (3-isobutyl-1-methyl-7H-purine-2,6-dione).

The structure of (theobromine)2H2l8 has revealed that this is a polyiodide salt containing protonated theobromine.The anion It6 is the largest discrete polyiodide ion that has been characterized until now. A projection of this centrosymmetric anion is shown in Figure 1 it is evident that the ion is nearly planar and is best described as being I3——1 3 —13—12—13. 

Early on, Fischer discovered the active ingredients in coffee and tea, caffeine and theobromine. Eventually he discovered their structures and synthesized them in the laboratory. In work that he carried out between 1882 and 1906, Eischer demonstrated that adenine and guanine, along with some other compounds found in plants and animals, all belonged to one family of compounds. He called these the purines. All the purines have the same core structure and differ from one another by the functional groups attached to the ring. 

Caffeine enters the bloodstream about ten minutes after its ingestion and stays in the body for up to twelve hours. Like other alkaloids, caffeine has powerful physiological effects on humans and animals. It stimulates heart muscle and relaxes certain structures that contain smooth muscle, including the coronary arteries and the bronchi. It is a diuretic. Theophylline and theobromine, two other plant alkaloid derivatives of xanthine, have physiological effects similar to those of caffeine. 

Triacanthine (17) has been isolated from Holarrhena mitis Details on the structure and total synthesis of eritadenine (18), a hypocholesterolemic alkaloid from Lentinus edodes, have been reported.An unsuccessful attempt to improve the imidazole ring-closure reaction in a total synthesis of eritadenine, which has been previously discussed, was also reported in this study. Concentrations of both caffeine and theobromine in the cocoa bean were shown to increase most markedly in the time period from flowering to harvest. ... 

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