Catabolism of caffeine in plants and microorganisms

Mazzafera, Paulo

doi:10.2741/1339

Cited by 74 publications

(89 citation statements)

References 60 publications

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“…On the other hand, theobromine, the long-assumed universal precursor to caffeine in plants (11), is undetectable or present only at low levels in developing buds (41). These findings are particularly intriguing, given that no enzymes have been previously reported to be specialized for these methylation reactions to form theophylline or caffeine and because theophylline is usually considered a degradation product of caffeine (42,43). We expected Citrus to use the same gene family members and pathway as Paullinia because both are members of Sapindales ( Fig.…”

Section: Resultsmentioning

confidence: 99%

Convergent evolution of caffeine in plants by co-option of exapted ancestral enzymes

Huang

O’Donnell

Barboline

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

109

156

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Convergent evolution is a process that has occurred throughout the tree of life, but the historical genetic and biochemical context promoting the repeated independent origins of a trait is rarely understood. The well-known stimulant caffeine, and its xanthine alkaloid precursors, has evolved multiple times in flowering plant history for various roles in plant defense and pollination. We have shown that convergent caffeine production, surprisingly, has evolved by two previously unknown biochemical pathways in chocolate, citrus, and guaraná plants using either caffeine synthaseor xanthine methyltransferase-like enzymes. However, the pathway and enzyme lineage used by any given plant species is not predictable from phylogenetic relatedness alone. Ancestral sequence resurrection reveals that this convergence was facilitated by co-option of genes maintained over 100 million y for alternative biochemical roles. The ancient enzymes of the Citrus lineage were exapted for reactions currently used for various steps of caffeine biosynthesis and required very few mutations to acquire modern-day enzymatic characteristics, allowing for the evolution of a complete pathway. Future studies aimed at manipulating caffeine content of plants will require the use of different approaches given the metabolic and genetic diversity revealed by this study. convergent evolution | caffeine biosynthesis | enzyme evolution | paleomolecular biology

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Section: Resultsmentioning

confidence: 99%

Convergent evolution of caffeine in plants by co-option of exapted ancestral enzymes

Huang

O’Donnell

Barboline

et al. 2016

Proc. Natl. Acad. Sci. U.S.A.

109

156

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“…Xanthine is further degraded by the conventional purine catabolism pathway to CO 2 and NH 3 via uric acid, allantoin and allantoate. A detailed review of catabolism of caffeine in plants and microorganisms has been published by Mazzafera (2004). Since exogenously supplied [8-14 C]theophylline is degraded to CO 2 far more rapidly than [8-14 C]caffeine, the initial step, namely the conversion of caffeine to theophylline, seems to be the major rate-limiting step of caffeine catabolism Ito et al, 1997).…”

Section: Degradation Of Caffeinementioning

confidence: 99%

Metabolism of alkaloids in coffee plants

Ashihara

2006

Braz. J. Plant Physiol.

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Coffee beans contain two types of alkaloids, caffeine and trigonelline, as major components. This review describes the distribution and metabolism of these compounds. Caffeine is synthesised from xanthosine derived from purine nucleotides. The major biosynthetic route is xanthosine → 7-methylxanthosine → 7-methylxanthine → theobromine → caffeine. Degradation activity of caffeine in coffee plants is very low, but catabolism of theophylline is always present. Theophylline is converted to xanthine, and then enters the conventional purine degradation pathway. A recent development in caffeine research is the successful cloning of genes of N-methyltransferases and characterization of recombinant proteins of these genes. Possible biotechnological applications are discussed briefly. Trigonelline (N-methylnicotinic acid) is synthesised from nicotinic acid derived from nicotinamide adenine nucleotides. Nicotinate N-methyltransferase (trigonelline synthase) activity was detected in coffee plants, but purification of this enzyme or cloning of the genes of this N-methyltransferase has not yet been reported. The degradation activity of trigonelline in coffee plants is extremely low. Key words: Coffea, caffeine, purine alkaloids, pyridine alkaloids, theobromine, trigonelline. Metabolismo de alcalóides em plantas de café:Sementes de café possuem dois tipos de alcalóides, cafeína e trigonelina, como principais componentes. Esta revisão descreve a distribuição e metabolismo desses compostos. Cafeína é sintetizada a partir da xantosina derivada de nucleotídeos purínicos. A principal rota biossintética é xantosina → 7-metilxantosina → 7-metilxantina → teobromina → cafeína. A atividade de degradação de cafeína em café é muito baixa, mas o catabolismo de teofilina está sempre presente. Teofilina é convertida a xantina, que entra na via convencional de degradação de purinas. Um recente desenvolvimento na pesquisa com cafeína é a clonagem de genes de N-metiltransferases e a caracterização de proteínas recombinantes desses genes. Possíveis aplicações biotecnológicas são discutidas brevemente. Trigonelina (ácido N-metilnicotínico) é sintetizada a partir de ácido nicotínico derivado de nucleotídeos de nicotinamida adenina. Atividade de nicotinato N-metiltransferase (trigonelina sintase) foi detectada em plantas de café, mas a purificação desta enzima ou a clonagem dos genes desta N-metiltransferase ainda não foi relatada na literatura. A atividade de degradação de trigonelina em café é extremamente baixa.

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“…Hence, caffeine and related methylxanthines enter soil and water easily through decomposed plant materials and other means, such as effluents from coffee-and tea-processing facilities. Therefore, it is not surprising that microorganisms capable of degrading caffeine have been isolated from various natural environments, with or without enrichment procedures (3,10). Bacteria use oxidative and N-demethylating pathways for catabolism of caffeine.…”

mentioning

confidence: 99%

“…Subsequent N demethylation of theobromine or paraxanthine to xanthine is via 7-methyxanthine. Xanthine is further oxidized to uric acid by xanthine dehydrogenase/oxidase (3,10). Although the identities of metabolites and the sequence of metabolite formation for caffeine N demethylation are well established, there is very little information on the number and nature of N-demethylases involved in this pathway.…”

mentioning

confidence: 99%

Two Distinct Pathways for Metabolism of Theophylline and Caffeine Are Coexpressed in Pseudomonas putida CBB5

Louie

Summers

et al. 2009

J Bacteriol

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Pseudomonas putida CBB5 was isolated from soil by enrichment on caffeine. This strain used not only caffeine, theobromine, paraxanthine, and 7-methylxanthine as sole carbon and nitrogen sources but also theophylline and 3-methylxanthine. Analyses of metabolites in spent media and resting cell suspensions confirmed that CBB5 initially N demethylated theophylline via a hitherto unreported pathway to 1-and 3-methylxanthines. NAD(P)H-dependent conversion of theophylline to 1-and 3-methylxanthines was also detected in the crude cell extracts of theophylline-grown CBB5. 1-Methylxanthine and 3-methylxanthine were subsequently N demethylated to xanthine. CBB5 also oxidized theophylline and 1-and 3-methylxanthines to 1,3-dimethyluric acid and 1-and 3-methyluric acids, respectively. However, these methyluric acids were not metabolized further. A broad-substrate-range xanthine-oxidizing enzyme was responsible for the formation of these methyluric acids. In contrast, CBB5 metabolized caffeine to theobromine (major metabolite) and paraxanthine (minor metabolite). These dimethylxanthines were further N demethylated to xanthine via 7-methylxanthine. Theobromine-, paraxanthine-, and 7-methylxanthine-grown cells also metabolized all of the methylxanthines mentioned above via the same pathway. Thus, the theophylline and caffeine N-demethylation pathways converged at xanthine via different methylxanthine intermediates. Xanthine was eventually oxidized to uric acid. Enzymes involved in theophylline and caffeine degradation were coexpressed when CBB5 was grown on theophylline or on caffeine or its metabolites. However, 3-methylxanthine-grown CBB5 cells did not metabolize caffeine, whereas theophylline was metabolized at much reduced levels to only methyluric acids. To our knowledge, this is the first report of theophylline N demethylation and coexpression of distinct pathways for caffeine and theophylline degradation in bacteria.Caffeine (1,3,7-trimethylxanthine) and related methylxanthines are widely distributed in many plant species. Caffeine is also a major human dietary ingredient that can be found in common beverages and food products, such as coffee, tea, and chocolates. In pharmaceuticals, caffeine is used generally as a cardiac, neurological, and respiratory stimulant, as well as a diuretic (3). Hence, caffeine and related methylxanthines enter soil and water easily through decomposed plant materials and other means, such as effluents from coffee-and tea-processing facilities. Therefore, it is not surprising that microorganisms capable of degrading caffeine have been isolated from various natural environments, with or without enrichment procedures (3, 10). Bacteria use oxidative and N-demethylating pathways for catabolism of caffeine. Oxidation of caffeine by a Rhodococcus sp.-Klebsiella sp. mixed-culture consortium at the C-8 position to form 1,3,7-trimethyluric acid (TMU) has been reported (8). An 85-kDa, flavin-containing caffeine oxidase was purified from this consortium (9). Also, Mohapatra et al. (12) purified a 65-kDa...

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Catabolism of caffeine in plants and microorganisms

Cited by 74 publications

References 60 publications

Convergent evolution of caffeine in plants by co-option of exapted ancestral enzymes

Convergent evolution of caffeine in plants by co-option of exapted ancestral enzymes

Metabolism of alkaloids in coffee plants

Two Distinct Pathways for Metabolism of Theophylline and Caffeine Are Coexpressed in Pseudomonas putida CBB5

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