Biosynthesis and biodegradation of caffeine, theobromine, and theophylline in Coffea arabica L. fruits

Suzuki, Takeo; Waller, George R.

doi:10.1021/jf00124a038

Cited by 62 publications

(45 citation statements)

References 16 publications

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“…Vol. 103, 1993 ~ significantly greater than reported previously for coffee fruit: compare 103 and 171 nmol of [14C]adenine incorporated into theobromine and caffeine, respectively, g-' fresh weight of leaf tissue during a 7-h incubation period in this study to 0.3 and 2.0 nmol of [14C]adenine incorporated into theobromine and caffeine, respectively, g-' of immature coffee fruit during a 36-h incubation period (Suzuki and Waller, 1984). The low rate of incorporation observed for coffee fruit may be due to the duration of the incubation period.…”

Section: Dlscussloncontrasting

confidence: 45%

“…and Waller, 1984;Negishi et al, 1985c), whereas the radiolabeled ribosides were first incorporated into 7-methylxanthosine and then into 7-methylxanthanine, theobromine, and caffeine (Negishi et al, 1992). Both 7-methylxanthosine and 7-methylxanthine were methylated to form theobromine and caffeine, but 7-methylinosine and 7-methylguanosine were not (Looser et al, 1974;Baumann and Wanner, 1977).…”

mentioning

confidence: 99%

“…Both 7-methylxanthosine and 7-methylxanthine were methylated to form theobromine and caffeine, but 7-methylinosine and 7-methylguanosine were not (Looser et al, 1974;Baumann and Wanner, 1977). In view of these results, there is much speculation regarding the substrate of the first methylation step and subsequent enzyme reactions leading to the synthesis of theobromine (Ogutuga andNorthcote, 1970a, 1970b;Baumann and Wanner, 1977;Baumann et al, 1978;Roberts and Waller, 1979;Waller et al, 1983;Suzuki and Waller, 1984;Suzuki et al, 1992). In addition, the relationship between theobromine and caffeine (1,3,7-trimethylxanthine) remains equivocal.…”

mentioning

confidence: 99%

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Separate de Novo and Salvage Purine Pools Are Involved in the Biosynthesis of Theobromine but Not Caffeine in Leaves of Coffea arabica L

Nazario

Lovatt

1993

Plant Physiol.

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Section: Dlscussloncontrasting

confidence: 45%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Separate de Novo and Salvage Purine Pools Are Involved in the Biosynthesis of Theobromine but Not Caffeine in Leaves of Coffea arabica L

Nazario

Lovatt

1993

Plant Physiol.

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“…It occurs mainly during the immature green stage of coffee fruit development (Suzuki and Waller, 1984 …”

Section: -Methylxanthine Nucleosidase: N-methylnucleosidasementioning

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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“…The caffeine catabolism is not included in The caffeine biosynthesis and biodegradation reactions occur more rapidly within immature than mature fruit. Both immature and mature coffee fruits and leaves degraded caffeine to theobromine, theophylline, N 3 -methylxanthine, N 7 -methylxanthine, xanthine, allantoin, allantoic acid, and urea (Kalberer, 1965;Suzuki and Waller, 1984a;Ashihara et al, 1996b). When Suzuki and Waller (1984b) studied the pattern of formation of theobromine, theophylline, and caffeine in coffee berries during the growth stages of the bean, they found evidence that theophylline arises from the caffeine breakdown in excised mature coffee berries.…”

Section: Biosynthesis Of Methylxanthines In Plantsmentioning

confidence: 99%

Intake of caffeine and other methylxanthines during pregnancy and risk for adverse effects in pregnant women and their foetuses

Andersson¹,

Hallström²,

Kihlman³

2005

TemaNord

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Biosynthesis and biodegradation of caffeine, theobromine, and theophylline in Coffea arabica L. fruits

Cited by 62 publications

References 16 publications

Separate de Novo and Salvage Purine Pools Are Involved in the Biosynthesis of Theobromine but Not Caffeine in Leaves of Coffea arabica L

Separate de Novo and Salvage Purine Pools Are Involved in the Biosynthesis of Theobromine but Not Caffeine in Leaves of Coffea arabica L

Metabolism of alkaloids in coffee plants

Intake of caffeine and other methylxanthines during pregnancy and risk for adverse effects in pregnant women and their foetuses

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