Theobromine , formerly known as xantheose , is a bitter alkaloids from cacao plants, with the chemical formula C 7 H 8 N 4 O 2 . It is found in chocolate, as well as in a number of other foods, including tea plant leaves, and kola nuts. These are classified as xanthine alkaloids, others include theophylline and caffeine. Different compounds in caffeine have an extra methyl group (see below Pharmacology section).
Despite its name, the compound does not contain bromine - theobromine derived from Theobroma , the name of the genus of cocoa trees (which itself consists of the Greek root theo (" ") and broma (" food "), meaning" food of the gods ") with the -inu suffix given to alkaloids and other basic nitrogen-containing compounds.
Theobromine is a powder that is slightly soluble in water (330Ã, mg/L), crystalline, bitter. Theobromine is white or colorless, but commercial samples can be yellowish. It has an effect similar to, but lower than, caffeine in the human nervous system, making it a lower homologue. Theobromine is a theophylline isomer, as well as paraxanthine. Theobromine is categorized as dimethyl xanthine.
Theobromine was first discovered in 1841 in cocoa beans by the Russian chemist Alexander Voskresensky. Theobromine synthesis of xanthine was first reported in 1882 by Hermann Emil Fischer.
Video Theobromine
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Theobromine is the main alkaloid found in chocolate and cocoa. Cocoa powder can vary in the amount of theobromine, from 2% theobromine, to a higher level of about 10%. There is usually a higher concentration in the dark than in milk chocolate. Theobromine can also be found in small amounts in cola nuts (1.0-2.5%), guarana berries, yerba mate ( paraguariensis ), and tea plants. 28 grams (1 oz) milk chocolate contains about 60 milligrams (1 egg) theobromine, while the same amount of dark chocolate contains about 200 milligrams (3 eggs). Cocoa beans naturally contain about 1% theobromine.
Spesies tanaman dengan jumlah theobromin terbesar adalah: Theobroma cacao Theobroma bicolor Ilex paraguariensis ilex guayusa Camellia sinensis Cola acuminata Theobroma angustifolium Guarana Coffea arabica
The average theobromine concentrations in cocoa and carob products are:
Biosynthesis
Theobromine is a purine alkaloid derived from xanthosine, nucleoside. Cleavage of ribose and N-methylation produces 7-methylxanthosine. 7-Methylxanthosine in turn is a precursor for theobromine, which in turn is a precursor for caffeine.
Maps Theobromine
Therapeutic use
Theobromine is a vasodilator (dilation of blood vessels), diuretics (urinary assistance), and heart stimulants. Currently not used as a medicinal drug.
Theobromine increases urine production. Because of the effect of this diuretic, and its ability to dilate blood vessels, theobromine has been used to treat high blood pressure. The American Journal of Clinical Nutrition notes that the historical use of theobromine as a treatment for other circulatory problems including arteriosclerosis, certain vascular disease, angina pectoris, and hypertension should be considered in future studies.
After the discovery at the end of the 19th century, theobromine was used in 1916, when it was recommended by the publication of the Principles of Medical Treatment as a treatment for edema (excess fluid in body parts), angina syphilis, and degenerative angina.
In the human body, theobromine levels are divided between 6-10 hours after consumption.
Theobromine has also been used in experimental birth defects involving rats and rabbits. Decreased fetal weights were recorded in rabbits after being force-fed, but not after other theobromine administration. Birth defects are not seen in mice. The possible future use of theobromine in such areas as cancer prevention has been patented.
Theobromine has also been shown to increase the microhardness of tooth enamel which can increase the potential resistance to tooth decay.
Pharmacology
Even without dietary intake, theobromine can occur in the body as it is a product of human metabolism of caffeine, which is metabolized in the liver to 12% theobromine, 4% theophylline, and 84% paraxanthine.
At heart, theobromine is metabolized to xanthine and subsequently to methyluric acid. Important enzymes include CYP1A2 and CYP2E1.
Like other methylated xanthine derivatives, theobromine is both:
- a competitive nonselective phosphodiesterase inhibitor, which increases intracellular cAMP, activates PKA, inhibits TNF-alpha synthesis and leukotriene, and reduces inflammation and innate immunity and
- selective adenosine receptor antagonist.
As a phosphodiesterase inhibitor, theobromine prevents the phosphodiesterase enzyme from converting the active cAMP into an inactive form. cAMP serves as the second messenger in many metabolic systems of hormones and neurotransmitters, such as glycogen damage. When cAMP inactivation is inhibited by compounds such as theobromine, the effects of neurotransmitters or hormones that stimulate cAMP production last longer. In general, the net result is a stimulatory effect.
Effects
Man
The amount of theobromine found in chocolate is small enough that chocolate can, in general, be safe for human consumption. Theobromine poisoning can occur due to large chronic or acute consumption in large numbers, especially in the elderly. At doses of 0.8-1.5 g/day (50-100 g cocoa) sweats, tremors and severe headaches are recorded. Limited mood effects are shown at 250 mg/day and negative mood effects above.
Theobromine and caffeine are similar because they are alkaloids linked. Theobromine is weaker in both the cyclic inhibition of the nucleotide phosphodiesterase and the antagonism of the adenosine receptor. Therefore, theobromine has a lower impact on the human central nervous system than caffeine. Theobromine stimulates the heart to a greater extent. While theobromine is not so addictive, it has been cited as a possible cause for chocolate addiction. Theobromine has also been identified as one of the compounds that contribute to the role of the famous chocolate as an aphrodisiac.
Because it is a myocardial stimulant as well as a vasodilator, it increases the heart rate, and also dilates the blood vessels, causing a drop in blood pressure. A paper published in 2005 showed that a drop in blood pressure may be caused by flavanols. Its drying effect allows it to be used to treat heart failure, which leads to and is aggravated by excessive accumulation of fluid in the body.
A 2004 study published by Imperial College London concluded that theobromine has an antitussive effect (reducing cough) that is superior to codeine by suppressing vagal nerve activity. In the study, 1 gram (0.035 oz) of theobromine (equivalent to ~ 71 grams (2.5 oz) dark chocolate) significantly increased the capsaicin concentration threshold required to induce cough when compared with placebo. The drug, called BC1036, is being developed by UK private companies under Healthcare and uses theobromine to treat persistent cough. Theobromine is very helpful in treating asthma, because it relaxes the smooth muscle found in the bronchi.
A study conducted in Utah between 1983 and 1986, and published in 1993, suggests a possible link between theobromine and an increased risk of prostate cancer in older men. This relationship is not linearly found for aggressive tumors. Associations may be fake, but make sense. Prenatal and infant exposure to theobromine appears to be associated with hypospadias and testicular cancer in a population study.
Like caffeine, theobromine can cause sleeplessness, tremor, anxiety, anxiety, and contribute to increased urine production. Additional side effects include loss of appetite, nausea, vomiting, and withdrawal headaches.
Animal
Animals that metabolize theobromine (found in chocolate) more slowly, like dogs, may succumb to theobromine poisoning of at least 50 grams (1.8 oz) milk chocolate for smaller dogs and 400 grams (14 oz), or about nine 44-grams 1.55 oz) Hershey chocolate milk bar is small, for an average sized dog. It should be noted that theobromine concentration in dark chocolate (about 10 g/kg (0.16 oz/lb)) up to 10 times from milk chocolate (1 to 5 g/kg (0.016-0.080 oz/lb)) - means more dark chocolate toxic to dogs per unit of weight or volume than milk chocolate.
The same risk is reported for cats as well, although cats tend not to consume sweet foods, with most cats having no sweet taste receptors. Complications include digestive problems, dehydration, stimulation, and a slow heartbeat. The next stage of theobromine poisoning includes seizures such as epilepsy and death. If caught early, theobromine poisoning can be treated. Although not common, the tobacco poisoning effects can be fatal.
In 2014, four American black bears were found dead at a feeding location in New Hampshire. The necropsy and toxicology report conducted at the University of New Hampshire in 2015 confirmed that they died of heart failure caused by theobromine after they consumed 41 kilograms (90 pounds) of chocolate and donuts placed on site as bait. A similar incident killed a black bear in Michigan in 2011.
Toxicity to birds is unknown, but is usually considered toxic to birds. Rabbits can also succumb to chocolate poisoning.
Mutation of genes in mammalian cells
Theobromine is known to induce gene mutations in eukaryotes and lower bacteria. In 1991 and 1997, research by the International Agency for Research on Cancer has shown that genetic mutations occur in higher eukaryotic cells, especially cultured mammalian cells. However, theobromine is still listed as safe for human consumption due to inadequate evidence of carcinogenicity.
See also
- The history of chocolate
- Theodrenaline
References
Further reading
-
- [1] from the Database of Dangerous Bank
Source of the article : Wikipedia
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