Ratio of the R and S enantiomers of salsolinol in food and human urine

Benedetti, Μ. Strolin; Bellotti, V.; Pianezzola, E.; Moro, E.; Carminati, P.; Dostert, P.

doi:10.1007/bf01255818

Cited by 72 publications

(22 citation statements)

References 8 publications

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“…Such an enzymatic condensation has been described with DA and 3,4-dihydroxyphenylacetaldehyde as co-substrates which, incubated with (S)-norlaudanosoline synthase, selectively afford the (S)-THP enantiomer (Rueffer et al, 1981). The absolute configuration at C-1 in (S)-THP is inverse to that of the corresponding C atom (C-9) in morphine ( High concentrations of Sal have been found in some foods and beverages, particularly in the fermented, non-distilled types Strolin Benedetti et al, 1986;Dostert et al, 1987). Moreover, it was demonstrated that a large proportion of Sal is formed during the fermentation process.…”

Section: And_)l Nhmentioning

confidence: 97%

Dopamine-derived alkaloids in alcoholism and in Parkinson's and Huntington's diseases

Dostert¹,

Benedetti²,

Dordain

1988

J. Neural Transmission

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Tetrahydroisoquinoline (TIQ) alkaloids and 1-carboxy TIQ derivatives have been found in human fluids and/or tissues. The possible biosynthetic pathways of salsolinol (Sal), taken as an example of TIQs, are discussed, and the possibility that biosynthesis occurs through a stereospecific enzymatic reaction is considered. In this respect, it is reported that the R enantiomer of Sal predominates in urines of healthy volunteers, whereas the S enantiomer predominates in port wine and possibly in other beverages and foods, suggesting that Sal present in humans could have, at least partially, and endogenous enzymatic origin. TIQs and other dopamine-derived alkaloids are weak MAO inhibitors, the R enantiomer of Sal and salsolidine being more potent than the S form. The changes in monoamine oxidase activity and the nigrostriatal concentrations of dopamine and homovanillic acid in Parkinson's and Huntington's diseases and in alcoholism are reviewed. In these pathological situations, changes in the levels of dopamine-derived alkaloid levels may occur. The possibility that the modifications found might cause or contribute to changes in mental and/or neurophysiological states in these pathological situations is considered.

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Section: And_)l Nhmentioning

confidence: 97%

Dopamine-derived alkaloids in alcoholism and in Parkinson's and Huntington's diseases

Dostert¹,

Benedetti²,

Dordain

1988

J. Neural Transmission

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“…Salsolinol (SAL; 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline) is the Pictet-Spengler product of dopamine and acetaldehyde, and has been detected in foods such as banana and port wine [99] as well as in human brain tissue. [100,101] SAL has been speculated to play a role in the etiology of alcoholism, a somewhat controversial finding.…”

Section: Conclusion and Future Aspects Of The Pictetspenglerase Familymentioning

confidence: 99%

The Pictet–Spengler Reaction in Nature and in Organic Chemistry

et al. 2011

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Alkaloids are an important class of natural products that are widely distributed in nature and produced by a large variety of organisms. They have a wide spectrum of biological activity and for many years were used in folk medicine. These days, alkaloids also have numerous applications in medicine as therapeutic agents. The importance of these natural products in inspiring drug discovery programs is proven and, therefore, their continued synthesis is of significant interest. The condensation discovered by Pictet and Spengler is the most important method for the synthesis of alkaloid scaffolds. The power of this synthesis method has been convincingly proven in the construction of stereochemicaly and structurally complex alkaloids.

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“…We have recently established that the R isomer of salsolinol ( Fig. 1) is the predominant, or the only isomer present in the urine of healthy volunteers (Dostert et al, 1987;Strolin Benedetti et al, 1989a). Moreover, we have also suggested that, under physiological conditions, salsolinol should predominantly result from condensation of DA with pyruvic Proposed biosynthetic pathway of (R)-salsolinol in healthy subjects under normal conditions acid in brain (Dostert et al, 1989).…”

Section: Introductionmentioning

confidence: 88%

Biosynthesis of salsolinol, a tetrahydroisoquinoline alkaloid, in healthy subjects

Dostert

Benedetti

Bellotti

et al. 1990

J. Neural Transmission

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The R enantiomer of salsolinol was detected in the urine of two out of six healthy subjects, whereas 1,2-dehydrosalsolinol was present in the urine of all the subjects. (S)-salsolinol was never detected. Administration of Madopar for 7 days resulted in the presence of large amounts of (R)- and (S)-salsolinol in the urine of five out of the six subjects, the urinary excretion of 1,2-dehydrosalsolinol being generally not markedly increased. The presence of 1,2-dehydrosalsolinol in urine suggests that the biosynthesis of salsolinol in healthy volunteers should occur by condensation of dopamine with pyruvic acid, in keeping with Hahn's hypothesis. The absence of salsolinol in the urine of one subject after Madopar administration seems to indicate that the biological system(s) involved in the reduction of the C = N bond in 1,2-dehydrosalsolinol can be missing or not, or poorly, functional in some individuals, and suggests that there is no alternative pathway for the formation of salsolinol in healthy volunteers.

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Ratio of the R and S enantiomers of salsolinol in food and human urine

Cited by 72 publications

References 8 publications

Dopamine-derived alkaloids in alcoholism and in Parkinson's and Huntington's diseases

Dopamine-derived alkaloids in alcoholism and in Parkinson's and Huntington's diseases

The Pictet–Spengler Reaction in Nature and in Organic Chemistry

Biosynthesis of salsolinol, a tetrahydroisoquinoline alkaloid, in healthy subjects

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