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Special Issue "Aporphines and Oxoaporphines"

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

Deadline for manuscript submissions: closed (30 June 2009)

Special Issue Editor

Guest Editor
Prof. Dr. Eduardo Sobarzo-Sánchez

Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, Spain, and Vicerrectoria Académica, Universidad Central de Chile, Santiago, Chile
Website | E-Mail
Phone: +34 8818 14887
Fax: +34 981 59 49 12
Interests: medicinal chemistry; natural products; photochemistry reactivity; aporphine and oxoaporphine; oxoisoaporphine; coumarins

Keywords

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

Published Papers (7 papers)

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Research

Open AccessArticle Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine
Molecules 2012, 17(9), 10958-10970; doi:10.3390/molecules170910958
Received: 6 June 2012 / Revised: 27 August 2012 / Accepted: 6 September 2012 / Published: 12 September 2012
Cited by 5 | PDF Full-text (256 KB)
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)
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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; doi:10.3390/molecules16119714
Received: 13 October 2011 / Revised: 17 November 2011 / Accepted: 17 November 2011 / Published: 23 November 2011
Cited by 29 | PDF Full-text (203 KB)
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)
Open AccessArticle (+)-N-(2-Hydroxypropyl)lindcarpine: A New Cytotoxic Aporphine Isolated from Actinodaphne pruinosa Nees
Molecules 2009, 14(8), 2850-2856; doi:10.3390/molecules14082850
Received: 30 June 2009 / Revised: 22 July 2009 / Accepted: 27 July 2009 / Published: 31 July 2009
Cited by 8 | PDF Full-text (381 KB) | HTML Full-text | XML Full-text
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)
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Open AccessArticle Grandine A, a New Proaporphine Alkaloid from the Bark of Phoebe grandis
Molecules 2009, 14(3), 1227-1233; doi:10.3390/molecules14031227
Received: 23 December 2008 / Revised: 13 February 2009 / Accepted: 18 February 2009 / Published: 23 March 2009
Cited by 5 | PDF Full-text (182 KB) | HTML Full-text | XML Full-text
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)
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Open AccessArticle Total Syntheses of Telisatin A, Telisatin B and Lettowianthine
Molecules 2009, 14(3), 917-924; doi:10.3390/molecules14030917
Received: 2 February 2009 / Revised: 17 February 2009 / Accepted: 26 February 2009 / Published: 26 February 2009
Cited by 2 | PDF Full-text (145 KB) | HTML Full-text | XML Full-text
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)
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Open AccessArticle Total Synthesis and the Biological Activities of (±)-Norannuradhapurine
Molecules 2009, 14(1), 89-101; doi:10.3390/molecules14010089
Received: 2 December 2008 / Revised: 19 December 2008 / Accepted: 23 December 2008 / Published: 29 December 2008
Cited by 3 | PDF Full-text (114 KB) | HTML Full-text | XML Full-text
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)
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Open AccessArticle Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one
Molecules 2008, 13(12), 2935-2947; doi:10.3390/molecules13122935
Received: 8 November 2008 / Revised: 19 November 2008 / Accepted: 25 November 2008 / Published: 28 November 2008
PDF Full-text (136 KB) | HTML Full-text | XML Full-text
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)
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