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New aspects of biosynthesis and metabolism of N-acyldopamines in rat tissues

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Abstract

Possible biosynthetic pathways of N-acyldopamines in rat tissues were compared. It was shown that an insignificant amount of the conjugation products was formed during the incubation of arachidonic acid and dopamine, whereas the substitution of tyrosine for dopamine resulted in the productive biosynthesis of N-arachidonoyldopamine. The biosynthesis presumably involves several closely conjugated enzymatic stages, and free fatty acids rather than their CoA esters served as the starting substrates. The decarboxylation stage probably precedes the stage of catechol system formation, because N-acetyltyramine (a probable intermediate) was easily oxidized by monophenol monooxygenase to N-acyldopamine, whereas N-acyltyrosine is hydrolyzed under these conditions. Biosynthesis of N-acyldopamines in a cell-free medium was accompanied by their methylation. The possibility of oxidative metabolism of N-acyldopamines, which could serve as co-substrates or inhibitors of different oxidoreductases, was shown for the first time.

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Abbreviations

AA:

arachidonic acid

AA-DA, AA-3MDA, AA-TA, and AA-Tyr:

N-arachidonoyl derivatives of dopamine, 3′-O-methyldopamine, tyramine, and tyrosine, respectively

DHA-DA:

N-docosahexanoyl dopamine

DHA-3′MDA:

3′-O-methyldopamine

DOPA:

3,4-dihydroxyphenylalanine

NADA:

N-acyldopamine

NT:

p-iodonitrotetrazolium violet

Ol-DA:

N-oleolydopamine

Ol-3′MDA:

N-oleolyl-3′-O-methyldopamine

SAM:

S-adenosylmethionine

THP:

tetrahydrobiopterin.

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia

    M. G. Akimov, N. M. Gretskaya, M. Yu. Bobrov & V. V. Bezuglov

  2. Institute of Molecular Genetics, Russian Academy of Sciences, pl. Akademika Kurchatova 46, Moscow, 123182, Russia

    K. V. Shevchenko, V. P. Shevchenko & N. F. Myasoedov

Authors
  1. M. G. Akimov
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  2. N. M. Gretskaya
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  3. K. V. Shevchenko
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  4. V. P. Shevchenko
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  5. N. F. Myasoedov
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  6. M. Yu. Bobrov
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  7. V. V. Bezuglov
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Corresponding author

Correspondence to M. G. Akimov.

Additional information

Original Russian Text © M.G. Akimov, N.M. Gretskaya, K.V. Shevchenko, V.P. Shevchenko, N.F. Myasoedov, M.Yu. Bobrov, V.V. Bezuglov, 2007, published in Bioorganicheskaya Khimiya, 2007, Vol. 33, No. 6, pp. 648–652.

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Akimov, M.G., Gretskaya, N.M., Shevchenko, K.V. et al. New aspects of biosynthesis and metabolism of N-acyldopamines in rat tissues. Russ J Bioorg Chem 33, 602–606 (2007). https://doi.org/10.1134/S1068162007060118

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  • DOI: https://doi.org/10.1134/S1068162007060118

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