Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors: occurrence, metabolism and function in human brains.

@article{Naoi2004DopaminederivedSD,
  title={Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors: occurrence, metabolism and function in human brains.},
  author={Makoto Naoi and Wakako Maruyama and G M. Nagy},
  journal={Neurotoxicology},
  year={2004},
  volume={25 1-2},
  pages={
          193-204
        }
}
Salsolinol, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, is an endogenous catechol isoquinoline detected in humans by M. Sandler. In human brain, a series of catechol isoquinolines were identified as the condensation products of dopamine or other monoamines with aldehydes or keto-acids. Recently selective occurrence of the (R)enantiomers of salsolinol derivatives was confirmed in human brain, and they are synthesized by enzymes in situ, but not by the non-enzymatic Pictet-Spengler… 
Salsolinol, a Dopamine-derived Tetrahydroisoquinoline, Occur in Dopaminergic SH-SY5Y Cells Induced by Dopamine
The dopamine-derived salsolinol (Sal), 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, has been considered a potential endogenous neurotoxin involved in the etiology of PD. In the present
Salsolinol, a tetrahydroisoquinoline-derived neurotoxin, induces oxidative modification of neurofilament-L protection by histidyl dipeptides.
TLDR
Carnosine, and anserine were shown to significantly prevent salsolinol- mediated NF-L aggregation, and both compounds inhibited the generation of hydroxyl radicals induced by salolinol.
Not Just from Ethanol. Tetrahydroisoquinolinic (TIQ) Derivatives: from Neurotoxicity to Neuroprotection
TLDR
It remains to be established whether a continuous exposure to TIQs or to their metabolites might carry toxicological consequences in the short- or long-term period.
Isoquinolines as Neurotoxins: Action and Molecular Mechanism
Derivatives from the isoquinoline group were found in many plants, food as well as in the mammalian brain. The interest with these substances appeared about 20 years back, after the exploration of
Inhibition of rodent brain monoamine oxidase and tyrosine hydroxylase by endogenous compounds - 1,2,3,4-tetrahydro-isoquinoline alkaloids.
TLDR
Four different noncatecholic TIQs, cyclic condensation derivatives of beta-phenylethylamine and dopamine with aldehydes or keto acids, were examined for the inhibition of rat and mouse brain monoamine oxidase (MAO) and rat striatum tyrosine hydroxylase (TH) activity.
Regional distribution of tetrahydroisoquinoline derivatives in rodent, human, and parkinson’s disease brain
TLDR
The data support the hypothesis of endogenous synthesis of salsolinols and provide evidence for their accumulation in catecholaminergic neurons and support the pathogenesis of monoaminergic cell death in Parkinson’s disease.
An (R)-specific N-methyltransferase involved in human morphine biosynthesis.
TLDR
Determination of kinetic parameters of NMT for the four (R)-configured benzylisoquinoline alkaloids by LC-MS/MS revealed (R-norreticuline) to be the best substrate with an even higher catalytic activity as compared to the previously reported natural substrate tryptamine.
Determination of Acetaldehyde, Salsolinol and 6-Hydroxy-1-methyl-1,2,3,4-tetrahydro-β-carboline in Brains after Acute Ethanol Administration to Neonatal Rats
Acetaldehyde, salsolinol (Sal), and 6-hydroxy-1-methyl-1,2,3,4-tetrahydro-β-carboline (6-OH-MTHβC) in neonatal rat brain after acute ethanol treatment were determined by high performance liquid
Salsolinol, a derivate of dopamine, is a possible modulator of catecholaminergic transmission: a review of recent developments.
  • B. Mravec
  • Biology, Medicine
    Physiological research
  • 2006
TLDR
Based on all of the discussed data the existence of a "salsolinolergic" system using salolinol as a neuromodulator, which may be present in catecholamine synthesizing neurons, is postulated.
Changes in salsolinol production and salsolinol synthase activity in Parkinson’s disease model
TLDR
The results indicate the relationship between the oxidative stress induced by 6-OHDA and the activity of salsolinol synthase, suggesting the correlation of the endogenous neurotoxin and Parkinson's disease.
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 69 REFERENCES
Tetrahydroisoquinolines derived from catecholamines or DOPA: effects on brain tyrosine hydroxylase activity.
TLDR
It is possible that tyrosine hydroxylase is affected at other doses or times, and that the blood-brain barrier is responsible for the lack of central effects, if catecholic tetrahydroisoquinolines are administered centrally or formed in neurons from condensations of catechol-amines and aldehydes.
Dopamine-derived tetrahydroisoquinoline alkaloids--inhibitors of neuroamine metabolism.
TLDR
The data suggest that, if formed in vivo under certain pharmacological conditions, aberrant neuroamme derived alkaloids may alter the metabolic disposition of endogenous neuroamines with resultant modification of adrenergic function.
Stereospecific occurrence of a parkinsonism-inducing catechol isoquinoline, n-methyl(R)salsolinol, in the human intraventricular fluid
TLDR
The results suggest that N-methyl(R)salsolinol synthesis may not depend on dopamine level, but on the activity of enzymes related to its synthesis and/or catabolism.
A novel enzyme enantio-selectively synthesizes (R)salsolinol, a precursor of a dopaminergic neurotoxin, N-methyl(R)salsolinol
TLDR
The isolation and characterization of a novel enzyme, which enantio-selectively synthesizes (R)salsolinol from dopamine and acetaldehyde is reported, and the possible function of this enzyme under physiological and pathological conditions in the brain is discussed.
Naturally-occurring isoquinolines perturb monoamine metabolism in the brain: studied by in vivo microdialysis
TLDR
Results are discussed in relation to possible involvement of these isoquinolines to the clinical features of some neuro-psychiatric diseases, such as alcoholism or in L-DOPA therapy, as proved by in vivo microdialysis technique.
(R) salsolinol N‐methyltransferase activity increases in parkinsonian lymphocytes
TLDR
In patients with Parkinson's disease, the activity of a neutral N‐methyltransferase, measured by using (R)salsolinol as a substrate, was found to increase significantly, suggesting its possible involvement in the pathogenesis of Parkinson's Disease.
Neuroamine-derived alkaloids: substrate-preferred inhibitors of rat brain monoamine oxidase in vitro.
TLDR
Findings indicated that SAL and the tetrahydroxyberbines were substrate-preferred inhibitors of type A MAO whereas THP was a relatively nonspecific inhibitor of rat brain MAO.
Structural studies of condensation products of biogenic amines as inhibitors of trytophan hydroxylase
TLDR
Results indicated that the catechol structure recognized and combined with TPH at a binding site different from that of the substrate or cofactor and the positive charge on the dopamine-derived substance enhanced the affinity to TPH.
Effects of norlaudanosolinecarboxylic acids on enzymes of catecholamine metabolism.
  • C. Coscia, W. Burke, +6 authors B. Roth
  • Chemistry, Medicine
    The Journal of pharmacology and experimental therapeutics
  • 1980
TLDR
In vivo studies of brain tyrosine metabolism in mouse neonates corroborated results on the in vitro effect of DNLCA on tyrosin hydroxylase and the potential of high-pressure liquid chromatography was demonstrated in both enzyme assays and radiometric studies of in vivo metabolism.
Enantio-selective occurrence of (S)-tetrahydropapaveroline in human brain
TLDR
The results suggest that (S)-tetrahydropapaveroline may be enantio-selectively synthesized in human brain and it may be an intermediate of the de novo synthesis of morphine analogues.
...
1
2
3
4
5
...