molecules-logo

Journal Browser

Journal Browser

Special Issue "Aporphines and Oxoaporphines"

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

Deadline for manuscript submissions: closed (30 June 2009).

Special Issue Editor

Prof. Dr. Eduardo Sobarzo-Sánchez
Website
Guest Editor
Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, Spain, and Instituto de Investigación e Innovación en Salud, Facultad de Ciencias de la Salud, Universidad Central de Chile, Chile
Interests: medicinal chemistry; natural products; photochemistry reactivity; aporphine and oxoaporphine; oxoisoaporphine; coumarins
Special Issues and Collections in MDPI journals

Keywords

  • medicinal chemistry
  • natural products
  • photochemistry reactivity
  • aporphine and oxoaporphine
  • oxoisoaporphine
  • coumarins

Published Papers (7 papers)

Order results
Result details
Select all
Export citation of selected articles as:

Research

Open AccessArticle
Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine
Molecules 2012, 17(9), 10958-10970; https://doi.org/10.3390/molecules170910958 - 12 Sep 2012
Cited by 10
Abstract
The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1 [...] Read more.
The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 15 and 3-azaoxoisoaporphine (6), some of them with phenolic structures, did not present any antioxidant capacity, possibly either by formation of keto-enol tautomerism species or the formation of unstable free radicals. Due to the singlet oxygen quantum yields (FD) near to unity, and greater photostability than phenalenone, oxoisoaporphines 46 may be considered as photosensitizers for singlet oxygen production and can be used as new universal study tools. The biological application as antibacterial agents is an important and possible tool in the study of compounds with low cytotoxicity and high reactivity in antineoplastic chemotherapy. On the other hand, when boldine and its annelated derivatives B14 are irradiated, a photoprotector effect is observed (SPF = 2.35), even after 30 minutes of irradiation. They also act as photoprotectors in cell fibroblast cultures. No hemolysis was detected for boldine hydrochloride and its salts without irradiation. In solutions irradiated before incubation (at concentrations over 200 ppm) photoproducts were toxic to the nauplii of Artemia salina. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Graphical abstract

Open AccessArticle
Trypanocidal Activity of Oxoaporphine and Pyrimidine-β-Carboline Alkaloids from the Branches of Annona foetida Mart. (Annonaceae)
Molecules 2011, 16(11), 9714-9720; https://doi.org/10.3390/molecules16119714 - 23 Nov 2011
Cited by 39
Abstract
Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH2Cl2 extract of four alkaloids: Atherospermidine (1), described for the first time in this species, liriodenine (2), O-methylmoschatoline (3), [...] Read more.
Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH2Cl2 extract of four alkaloids: Atherospermidine (1), described for the first time in this species, liriodenine (2), O-methylmoschatoline (3), and annomontine (4). Their chemical structures were established on the basis of spectroscopic data from IR, MS, NMR (1D and 2D), and comparison with the literature. Compounds 24 showed potent trypanocidal effect when evaluated against epimastigote and trypomastigote forms of Trypanosoma cruzi. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Figure 1

Open AccessArticle
(+)-N-(2-Hydroxypropyl)lindcarpine: A New Cytotoxic Aporphine Isolated from Actinodaphne pruinosa Nees
Molecules 2009, 14(8), 2850-2856; https://doi.org/10.3390/molecules14082850 - 31 Jul 2009
Cited by 11
Abstract
Onenewalkaloid; (+)-N-(2-hydroxypropyl)lindcarpine (1),together with four known aporphine alkaloids, (+)-boldine (2) (+)-norboldine (3), (+)-lindcarpine (4) and (+)-methyllindcarpine (5) were isolated from the stem bark of Actinodaphne pruinosa Nees (Lauraceae). (+)-N-(2-Hydroxypropyl)lindcarpine (1) exhibited cytotoxic activity against P-388 murine leukemia cells with [...] Read more.
Onenewalkaloid; (+)-N-(2-hydroxypropyl)lindcarpine (1),together with four known aporphine alkaloids, (+)-boldine (2) (+)-norboldine (3), (+)-lindcarpine (4) and (+)-methyllindcarpine (5) were isolated from the stem bark of Actinodaphne pruinosa Nees (Lauraceae). (+)-N-(2-Hydroxypropyl)lindcarpine (1) exhibited cytotoxic activity against P-388 murine leukemia cells with an IC50 value of 3.9 μg/mL. Structural elucidation of all the compounds were performed by spectral methods such as 1D- and 2D- NMR, IR, UV, and HRESIMS. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Graphical abstract

Open AccessArticle
Grandine A, a New Proaporphine Alkaloid from the Bark of Phoebe grandis
Molecules 2009, 14(3), 1227-1233; https://doi.org/10.3390/molecules14031227 - 23 Mar 2009
Cited by 9
Abstract
The stem bark of Phoebe grandis afforded one new oxoproaporphine; (–)-grandine A (1), along with six known isoquinoline alkaloids: (–)-8,9-dihydrolinearisine (2), boldine, norboldine, lauformine, scortechiniine A and scortechiniine B. In addition to that of the new compound, complete 1H- and 13C-NMR [...] Read more.
The stem bark of Phoebe grandis afforded one new oxoproaporphine; (–)-grandine A (1), along with six known isoquinoline alkaloids: (–)-8,9-dihydrolinearisine (2), boldine, norboldine, lauformine, scortechiniine A and scortechiniine B. In addition to that of the new compound, complete 1H- and 13C-NMR data of the tetrahydroproaporphine (–)-8,9-dihydrolinearisine (2) is also reported. The alkaloids’ structures were elucidated primarily by means of high field 1D- and 2D-NMR and HRMS spectral data. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Graphical abstract

Open AccessArticle
Total Syntheses of Telisatin A, Telisatin B and Lettowianthine
Molecules 2009, 14(3), 917-924; https://doi.org/10.3390/molecules14030917 - 26 Feb 2009
Cited by 6
Abstract
Treatment of 1-(2-bromoarylmethyl)-3,4-dihydroisoquinolines with oxalyl chloride and triethylamine gave 1-(2-bromophenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione derivatives, for example, 1-(2-bromophenyl)-5,6-dihydro-8,9-dimethoxypyrrolo[2,1-a]isoquinoline-2,3-dione. Radical cyclisation of these derivatives with tributyltin hydride and 1,1-azobis(cyclohexanecarbonitrile) afforded telisatin A, telisatin B and lettowianthine. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Graphical abstract

Open AccessArticle
Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
Molecules 2009, 14(1), 89-101; https://doi.org/10.3390/molecules14010089 - 29 Dec 2008
Cited by 5
Abstract
The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, [...] Read more.
The structure previously assigned to the phenolic noraporphine alkaloid, (-)-norannuradhapurine has been confirmed by a total synthesis of the racemic alkaloid in which the key step involved the formation of the C ring by a radical-initiated cyclization. although inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028, (±)-norannuradhapurine inhibits the production of NO, PGE2, TNF-a, IL-1b and IL-6 and the expression of iNOS and COX-2 in RAW 264.7 macrophages stimulated with LPS in vitro. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Graphical abstract

Open AccessArticle
Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
Molecules 2008, 13(12), 2935-2947; https://doi.org/10.3390/molecules13122935 - 28 Nov 2008
Cited by 2
Abstract
The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated [...] Read more.
The structures previously assigned to (+)-laurelliptinhexadecan-1-one (1a) and (+)-laurelliptinoctadecan-1-one (1b) from Cocculus orbiculatus (L.) DC. (Menispermaceae) have been confirmed by total synthesis of the racemic alkaloids. The key step of the synthesis involved formation of ring C of the aporphines by a radical-intiated cyclisation. Both (±)-laurelliptinhexadecan-1-one (1a) and (±)-laurelliptinoctadecan-1-one (1b) were inactive against Staphylococcus aureus ATCC25932, Escherichia coli ATCC10536 and Candida albicans ATCC90028. Full article
(This article belongs to the Special Issue Aporphines and Oxoaporphines)
Show Figures

Graphical abstract

Back to TopTop