Special Issue "Aporphines and Their Oxidized Derivatives: Synthesis and Pharmacological Behavior"

Guest Editor
Dr. Eduardo Sobarzo-Sánchez
Department of Pharmacy and Pharmaceutical Technology, Faculty of Pharmacy, University of Santiago de Compostela, E-15782 Santiago de Compostela, Spain
Website: http://webspersoais.usc.es/persoais/e.sobarzo/
E-Mail: e.sobarzo@usc.es
Phone: +34 881 814 887
Fax: +34 981 59 49 12
Interests: medicinal chemistry; natural products; photochemistry reactivity; aporphine and oxoaporphine; oxoisoaporphine; coumarins

Dear Colleagues,

Since the beginnings of the studies about the natural products, the aporphine derivatives are the most important group of isoquinoline alkaloids in the nature, with a variety of examples of chemical structure and pharmacological application. Thus, for instance, (S)-(+)-Boldine(2,9-dihydroxy-1,10-dimethoxy-N-methyl-4H-dibenzo[de,g]quinoline) from boldo tree (Peumus boldus Molina. Monimiaceae), native to the central region of Chile, it has shown wide pharmacological activities unknown for many people. Thus, it has been characterized in the past few years as an antioxidant that effectively protects different systems against free-radical-induced lipid peroxidation or enzyme inactivation.

On the other hand, the oxidated derivatives of the aporphine called “oxoaporphine” are the compounds with major number of bibliographic citations about the pharmacology in different diseases such as antiparasitic, cancer, depression, etc. However, at the present, other groups of isoquinoline alkaloid isolated from Chinese roots called “Oxoisoaporphine” have been described with innumerable chemical and pharmacological reactivities, which to allow us to assure that these compounds have a wide applicability in the treatment either of disease or conductual disorders and oncological disease. The importance of this group of alkaloids increases constantly due to the diversity of chemical structure and the sources to isolate them.

Dr. Eduardo Sobarzo-Sánchez
Guest Editor

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• isoquinoline alkaloid
• aporphine
• oxoaporphine
• oxoisoaporphine
• depression
• oncological disease
• antiparasitic disease
• pharmacological application

Type of Paper: Article
Title: Molecular Engineering of Benzylisoquinoline Alkaloid Biosynthesis in Eschscholzia californica Using a Cytochrome P450 gene, CYP80G2, from Coptis japonica Cells
Authors: Y.L. Chow and Fumihiko Sato
Affiliation: Laboratory for Molecular and Cellular Biology of Totipotency, Graduate School of Biostudies, Kyoto University, Kyoto 606-8502, Japan; E-Mail: fsato@lif.kyoto-u.ac.jp
Abstract: Corytuberine synthase (CYP80G2) is the key entry enzyme for the production of aporphine alkaloids.  We investigate the effect of the heterologous expression of CYP80G2 gene from Coptis japonica in Eschscholzia  californica cells, which usually do not produce aporphine alkaloids. Ectopic expression of CjCYP80G2 in E. californica cells induced the accumulation of corytuberine and its N-methylated product magnoflorine. Analysis of expression level of CjCYP80G2 and some related genes in benzophenanthridine alkaloids indicated the significant effect of CjCYP80G2 expression on the modification of alkaloid profile. Biological activities assay of the crude cell extracts from transgenic E. californica cells with CjCYP80G2 using Caenorhabditis elegans is also discussed.

Type of Paper: Article
Title: Trypanocidal Activity of Aporphine and Pyrimidine-β-Carboline Alkaloids from the Branches of Annona foetida Mart. (Annonaceae)
Authors: Emmanoel Vilaça Costa, Maria Lúcia Belém Pinheiro *, Andersson Barison, Francinete Ramos Campos, Rodrigo Hinojosa Valdez , Tânia Ueda-Nakamura, Benedito Prado Dias Filho and Celso Vataru Nakamura
Affiliation: Federal University of Amazonas, Department of Chemistry, 69077-000, Manaus, AM, Brazil; E-Mail: lbelem@ufam.edu.br
Abstract: Phytochemical investigation of the branches of Annona foetida Mart. led to isolation of four alkaloids: atherospermidine (1), liriodenine (2), O-methylmoschatoline (3), and annomontine (4) from CH2Cl2 extract. Their chemical structures were established on the basis of spectroscopic data from IR, ESI-MS, NMR (including 2D experiments), and comparison with the literature. Atherospermidine is described in this species for the first time. The trypanocidal activity against epimastigote and trypomastigote forms of Trypanosoma cruzi was investigated for liriodenine, O-methylmoschatoline, and annomontine. Additionally was observed that these compounds had potent trypanocidal effect against T.  cruzi.

Type of Paper: Review
Title: Aporphines as 5-HT Receptor Ligands
Author: Wayne W. Harding
Affiliation: Chemistry Department, Hunter College, CUNY, 695 Park Avenue, New York, NY 10065, USA; E-Mail: whardi@hunter.cuny.edu
Abstract: Aporphines are promiscuous central nervous system (CNS) receptor ligands that are known to interact with dopamine (D), α-adrenergic  and serotonin (5-HT) receptors. The tetracyclic aporphine template is a promising scaffold for the development of selective or multi-potent probes that target sub-types of these receptor poulations.  Such compounds are valuable to interrogate CNS-mediated disorders such as anxiety, depression, schizophrenia and drug abuse. Although a number of reviews have appeared that focus on aporphines as dopaminergic ligands, the serotonergic activity of aporphines has not been extensively reviewed to date. This is a comprehensive review on the synthesis and pharmacological activity of aporphines as ligands that target 5-HT receptors.

Type of paper: Review
Title: The Pharmacological Properties and Therapeutic Use of Apomorphine
Author: Samo Ribarič
Affiliation: Institute of Pathophysiology, Faculty of Medicine, University of Ljubljana, Zaloška 4, SI-1000 Ljubljana, Slovenia & University Clinical Centre Ljubljana, Departement of Neurology, Laboratory for Movement Disorders, Zaloška 4, SI-1000 Ljubljana, Slovenia; E-Mail: samo.ribaric@mf.uni-lj.si; Tel.: +386-1-543-70-53; Fax: +386-543-70-21.
Abstract: Apomorphine (APO) is an aporphine derivative used in human and veterinary medicine. APO activates D₁, D_2S, D_2L, D₃, D₄, and D₅ receptors (and is thus classified as a non-selective dopamine agonist), serotonin receptors (5HT_1A, 5HT_2A, 5HT_2B, and 5HT_2C), and a-adrenergic receptors (a_1B, a_1D, a_2A, a_2B, and a_2C). In veterinary medicine, APO is used to induce vomiting in dogs, an important early treatment for some orally ingested toxin (e.g. anti-freeze or insecticide). In human medicine, it has been used in a variety of treatments ranging from the treatment of addiction (i.e. to heroin, alcohol or cigarettes), for treatment of erectile dysfunction in males and hypoactive sexual desire disorder in females to the treatment of chronic neurological diseases. Currently, APO is used in patients with advanced Parkinson's disease, for the treatment of persistent and disabling motor fluctuations which do not respond to levodopa or other dopamine agonists, either on it is own or in combination with deep brain stimulation. Recently, a new and potentially important therapeutic role for APO in the treatment of Alzheimer’s disease has been suggested; APO seems to stimulate Ab catabolism, thus reducing the rate of Ab oligomerisation and consequent neural cell death.

Type of Paper: Article
Title: Biofunctional Constituents from the Stems of Liriodendron Tulipifera
Author: Chugn-Yi ChenAffiliation: School of Medicine and Health Sciences, Fooyin University; E-Mail: xx377@mail.fy.edu.tw
Abstract: Twenty-one known compounds have been isolated from the stems of Liriodendron tulipifera. The structures of these pure constituents were determined using spectroscopic analysis. Isolated compounds were screened for radical scavenging ability using 1,1-diphenyl-2-picrylhydrazul (DPPH) free radical scavenging activity assay, metal chelating power assay, and ferric reducing /antioxidantpower assay (FRAP). Compounds were evaluated for inhibition of proliferation and migration in human melanoma cells. The anti-tyrosinase effects were to calculate the hydroxylation of L-tyrosine to L-dopa according to in vitro mushroom tyrosinase assay. In addition, all compounds were evaluated for their cell proliferation and cell migration inhibition activities on human skin melanoma cells.