The 1,3,7,9-tetramethyluric acid content of cupu (Theobroma grandiflorum Schum.)

Baumann, Thomas W.; Wanner, Hans

doi:10.1590/1809-43921980102425

Cited by 17 publications

(9 citation statements)

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“…This group includes C. liberica, C. dewevrei and C. excelsa. Methyluric acids have also been found within the genera Herrania and Theobroma (38,39).…”

Section: Methyluric Acids As Intermediates In Caffeine Degradationmentioning

confidence: 99%

Catabolism of caffeine in plants and microorganisms

Mazzafera

2004

Front Biosci

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Caffeine has been found in tissues of several plants. Because of its stimulating effect on the central nervous system, a great number of reports have been published on its content in beverages and foodstuffs. However, a much more restricted number of reports have dealt specifically with caffeine metabolism in plants. This review presents, in chronological manner, the contribution of these reports to the vast knowledge accumulated on caffeine catabolism in plants and microorganisms over the last 40 years. In plants, the accumulated data indicate the operation of a main catabolic pathway: caffeine --> theophylline --> 3-methylxantine --> xanthine --> uric acid --> allantoin --> allantoic acid --> glyoxylic acid + urea --> NH3 + CO2. Some studies have shown that, depending on the plant species, other minor routes may operate with the formation of theobromine and 7-methylxantine, which are salvaged for caffeine formation since they also appear in the biosynthetic pathway. A specific group of coffee known as liberio-excelsioides has the ability to convert caffeine to the corresponding methyluric acid, which is methylated to other uric acid derivatives. In bacteria caffeine is either degraded to theobromine or paraxanthine. Both dimethylxanthines are demethylated to 7-methylxantine which in turn is demethylated to xanthine and then enters the catabolic pathway of purines. In bacteria, theobromine, paraxanthine and 7-methylxantine may also be oxidized to their corresponding methyluric acids.

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“…This group includes C. liberica, C. dewevrei and C. excelsa. Methyluric acids have also been found within the genera Herrania and Theobroma (38,39).…”

Section: Methyluric Acids As Intermediates In Caffeine Degradationmentioning

confidence: 99%

Catabolism of caffeine in plants and microorganisms

Mazzafera

2004

Front Biosci

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“…Cupu (Theobroma grandiflorum), contains 0.25% liberine in cotyledons and 0.08% in the nut shells (Baumann and Wanner, 1980). Hammerstone et al (1994) reported that theacrine is the principal purine alkaloid in seeds of eleven species of Theobroma and nine species of Herrania.…”

Section: Theobroma and Related Speciesmentioning

confidence: 99%

Caffeine and related purine alkaloids: Biosynthesis, catabolism, function and genetic engineering

Ashihara¹,

Sano²,

Crozier³

2008

Phytochemistry

332

259

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“…Conversely, many individuals, particularly those with underlying medical conditions (e.g., hypertension), report an increased incidence of anxiety, nervousness, and jitteriness at caffeine doses >400 mg/day. 18 Variation in caffeine sensitivity has spurred the discovery of wider therapeutic index natural stimulant platforms that include a unique class of purine alkaloids known as methylurates 4,7,8,19 . For example, the methylurate theacrine exerts its pharmacologic effects via adenosine receptor modulation 20 , a property shared by its structural analog caffeine 21 .…”

Section: Discussionmentioning

confidence: 99%

Caffeine and Methylliberine: A Human Pharmacokinetic Interaction Study

Mondal

Wang

Butawan

et al. 2021

Preprint

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Methylliberine and theacrine are methylurates found in the leaves of various Coffea species and Camellia assamica var. kucha, respectively. We previously demonstrated that the methylxanthine caffeine increased theacrine oral bioavailability in humans. Consequently, we conducted a double-blind, placebo-controlled study pharmacokinetic study in humans administered methylliberine, theacrine, and caffeine to determine methylliberine pharmacokinetic interaction potential with either caffeine or theacrine. Subjects (n = 12) received an oral dose of either methylliberine (25 or 100 mg), caffeine (150 mg), methylliberine (100 mg) plus caffeine (150 mg), or methylliberine (100 mg) plus theacrine (50 mg) using a randomized, double-blind, crossover design. Blood samples were collected over 24 hours and analyzed for methylliberine, theacrine, and caffeine using UPLC-MS/MS. Methylliberine exhibited linear pharmacokinetics that were unaffected by co-administration of either caffeine or theacrine. However, methylliberine co-administration resulted in decreased oral clearance (41.9 +/- 19.5 vs. 17.1 +/- 7.80 L/hr) and increased half-life (7.2 +/- 5.6 versus 15 +/- 5.8 hrs) of caffeine. Methylliberine had no impact on caffeine maximum concentration (440 +/- 140 vs. 458 +/- 93.5 ng/mL) or oral volume of distribution (351 +/- 148 vs. 316 +/- 76.4 L). We previously demonstrated theacrine bioavailability was enhanced by caffeine, however, caffeine pharmacokinetics were unaffected by theacrine. Herein, we found that methylliberine altered caffeine pharmacokinetics without a reciprocal interaction, which suggests caffeine may interact uniquely with different methylurates. Understanding the mechanism(s) of interaction between methylxanthines and methylurates is of critical importance in light of the recent advent of dietary supplements containing both purine alkaloid classes.

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The 1,3,7,9-tetramethyluric acid content of cupu (Theobroma grandiflorum Schum.)

Cited by 17 publications

References 0 publications

Catabolism of caffeine in plants and microorganisms

Catabolism of caffeine in plants and microorganisms

Caffeine and related purine alkaloids: Biosynthesis, catabolism, function and genetic engineering

Caffeine and Methylliberine: A Human Pharmacokinetic Interaction Study

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