Tetrahydropapaveroline in Parkinson’s Disease and Alcoholism: A Look Back in Honor of Merton Sandler

doi:10.1016/S0161-813X(03)00145-1

NeuroToxicology

Volume 25, Issues 1–2, January 2004, Pages 117-120

https://doi.org/10.1016/S0161-813X(03)00145-1 Get rights and content

Abstract

Although Dr. Merton Sandler’s extensive and vigorous research program over the years has been concerned mainly with classical biogenic amines, monoamine oxidase (MAO), and MAO inhibitors, he and his group contributed a significant early Parkinson’s disease-related study of a non-classical or “aberrant” biogenic amine. The formation and production of this amine, the dopamine-derived mammalian alkaloid, tetrahydropapaveroline (THP), is in fact dependent on MAO activity. As reviewed here, that study provided the groundwork for and indeed stimulated many later investigations of mammalian alkaloids in numerous laboratories around the world.

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Citation Excerpt :
They are also known to be present in some microorganisms such protists (Rhizaria, Alveolata and Amoebozoa), fungi (Opisthokonta), algae (Stramenopiles), eukaryote (Choanozoa), ascidians (Urochordata), and insects (Arthropoda) (Rasse-Suriani et al., 2017). The endogenous human brain, heart, plasma, kidney, liver cerebrospinal fluid, animal tissue, and some metabolites in mammals have also been reported to contain βCs in measurable amounts (Carlini, 2003; Jaqueline et al., 2006), such as, THβCs and tetrahydroisoquinolines (TIQs) are often referred to as ‘mammalian alkaloids’ (Collins, 2004). They are also found in common staple foods (Herraiz and Galisteo, 2018) such as grains and nuts, coffee (Casal, 2015), processed foods like roasted sugar beets, roasted chokeberries (Wojtowicz et al., 2015), alcoholic beverages (Park et al., 2010), natural products like banana, tomato juice, fish, meat (Piechowska et al., 2019), and even in cigarette smoke (Pfau and Skog, 2004).
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Mild Pictet–Spengler-type condensation was applied to the synthesis of several tetrahydro-β-carboline and tetrahydro-isoquinoline derivatives. l-Amino acids were promoters of 1,4-chirality transfer with up to 100% de. The stereochemistry of the final diketopiperazines strongly depended on the structure of the l-amino acids used: acyclic amino acids gave predominantly the (R)-configuration at the newly created stereogenic centre, whereas l-proline afforded the opposite configuration, as established by X-ray crystallography.
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Tetrahydropapaveroline in Parkinson’s Disease and Alcoholism: A Look Back in Honor of Merton Sandler

Abstract

Lancet

J. Chromatogr. A

Alcohol

Biochem. Pharmacol.

Metab. Clin. Exp.

Neurosci. Lett.

Brain Res. Bull.

Alcohol

Neurosci. Lett.

Trends Neurosci.

Biochem. Pharmacol.

Life Sci.

Effect of acute ethanol administration on brain levels of tetrahydropapaveroline in l-DOPA-treated rats

J. Neurosci. Res.

Acetaldehyde and its amine condensation products as markers in alcoholism

Rec. Dev. Alc.

Occurrence of a new class of tetrahydroisoquinoline alkaloids in l-DOPA-treated parkinsonian patients

Nature

Alcohol, amines, and alkaloids: a possible biochemical basis for alcohol addiction

Science