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Aporphines and Their Oxidized Derivatives: Synthesis and Pharmacological Behavior

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (29 February 2012) | Viewed by 19983

Special Issue Editor

Special Issue Information

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

Keywords

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

Published Papers (2 papers)

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Article
Bio-Functional Constituents from the Stems of Liriodendron tulipifera
by Chien-Chih Chiu, Han-Lin Chou, Pei-Fang Wu, Hsin-Liang Chen, Hui-Min Wang and Chung-Yi Chen
Molecules 2012, 17(4), 4357-4372; https://doi.org/10.3390/molecules17044357 - 10 Apr 2012
Cited by 32 | Viewed by 8480
Abstract
Four known compounds have been isolated from the stems of Liriodendron tulipifera, and the structures of these pure constituents were determined using spectroscopic analysis. Isolated compounds were screened for free radical scavenging ability, metal chelating power assay and ferric reducing antioxidant power [...] Read more.
Four known compounds have been isolated from the stems of Liriodendron tulipifera, and the structures of these pure constituents were determined using spectroscopic analysis. Isolated compounds were screened for free radical scavenging ability, metal chelating power assay and ferric reducing antioxidant power assay (FRAP). The anti-tyrosinase effects of L. tulipifera compounds were calculated the inhibition of hydroxylation of L-tyrosine to L-dopa according to an in vitro mushroom tyrosinase assay. The study also examined the bio-effects of the four compounds on the human melanoma A375.S2, and showed that liriodenine (1) and (-)-norglaucine (4) significantly inhibited the proliferation of melanoma cells in the cell viability assay. Wound healing results indicated that liriodenine (1), (-)-glaucine (3) and (-)-norglaucine (4) exerted anti-migration potential. Interestingly, (-)-glaucine (3), neither liriodenine (1) nor (-)-norglaucine (4) showed promising anti-migration potential without inducing significant cytotoxicity. Furthermore, a dramatically increased level of intracellular reactive oxygen species (ROS) was detected from (-)-glaucine (3). The cell cycle assessment demonstrated a moderate G2/M accumulation by (-)-glaucine (3). The above results revealed the anti-cancer effects of L. tulipifera compounds, especially on the anti-migration ability indicating the promising chemopreventive agents to human skin melanoma cells. Full article
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581 KiB  
Review
The Pharmacological Properties and Therapeutic Use of Apomorphine
by Samo Ribarič
Molecules 2012, 17(5), 5289-5309; https://doi.org/10.3390/molecules17055289 - 07 May 2012
Cited by 68 | Viewed by 10964
Abstract
Apomorphine (APO) is an aporphine derivative used in human and veterinary medicine. APO activates D1, D2S, D2L, D3, D4, and D5 receptors (and is thus classified as a non-selective dopamine agonist), [...] Read more.
Apomorphine (APO) is an aporphine derivative used in human and veterinary medicine. APO activates D1, D2S, D2L, D3, D4, and D5 receptors (and is thus classified as a non-selective dopamine agonist), serotonin receptors (5HT1A, 5HT2A, 5HT2B, and 5HT2C), and α-adrenergic receptors (α1B, α1D, α2A, α2B, and α2C). In veterinary medicine, APO is used to induce vomiting in dogs, an important early treatment for some common orally ingested poisons (e.g., anti-freeze or insecticides). 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 patients with Parkinson's disease (PD). Currently, APO is used in patients with advanced PD, for the treatment of persistent and disabling motor fluctuations which do not respond to levodopa or other dopamine agonists, either on its 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 in an animal model and cell culture, thus reducing the rate of Ab oligomerisation and consequent neural cell death. Full article
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