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13 pages, 256 KiB

Open AccessArticle

Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine

by Eduardo Sobarzo-Sánchez, Patricio González Soto, Cristóbal Valdés Rivera, Georgina Sánchez and María Eliana Hidalgo

Molecules 2012, 17(9), 10958-10970; https://doi.org/10.3390/molecules170910958 - 12 Sep 2012

Cited by 17 | Viewed by 6911

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 1–5 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 (F_D) near to unity, and greater photostability than phenalenone, oxoisoaporphines 4–6 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 B1–4 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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7 pages, 203 KiB

Open AccessArticle

Trypanocidal Activity of Oxoaporphine and Pyrimidine-β-Carboline Alkaloids from the Branches of Annona foetida Mart. (Annonaceae)

by Emmanoel Vilaça Costa, Maria Lúcia Belém Pinheiro, Afonso Duarte Leão de Souza, Andersson Barison, Francinete Ramos Campos, Rodrigo Hinojosa Valdez, Tânia Ueda-Nakamura, Benedito Prado Dias Filho and Celso Vataru Nakamura

Molecules 2011, 16(11), 9714-9720; https://doi.org/10.3390/molecules16119714 - 23 Nov 2011

Cited by 69 | Viewed by 7848

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 2–4 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)

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7 pages, 381 KiB

Open AccessArticle

(+)-N-(2-Hydroxypropyl)lindcarpine: A New Cytotoxic Aporphine Isolated from Actinodaphne pruinosa Nees

by Tiah Rachmatiah, Mat Ropi Mukhtar, Mohd Azlan Nafiah, Muhammad Hanafi, Soleh Kosela, Hiroshi Morita, Marc Litaudon, Khalijah Awang, Hanita Omar and A. Hamid A. Hadi

Molecules 2009, 14(8), 2850-2856; https://doi.org/10.3390/molecules14082850 - 31 Jul 2009

Cited by 19 | Viewed by 11745

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 IC₅₀value 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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7 pages, 182 KiB

Open AccessArticle

Grandine A, a New Proaporphine Alkaloid from the Bark of Phoebe grandis

by Mat Ropi Mukhtar, Ahmad Nazif Aziz, Noel F. Thomas, A. Hamid A. Hadi, Marc Litaudon and Khalijah Awang

Molecules 2009, 14(3), 1227-1233; https://doi.org/10.3390/molecules14031227 - 23 Mar 2009

Cited by 14 | Viewed by 14705

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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8 pages, 145 KiB

Open AccessArticle

Total Syntheses of Telisatin A, Telisatin B and Lettowianthine

by Surachai Nimgirawath and Phansuang Udomputtimekakul

Molecules 2009, 14(3), 917-924; https://doi.org/10.3390/molecules14030917 - 26 Feb 2009

Cited by 8 | Viewed by 8599

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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13 pages, 114 KiB

Open AccessArticle

Total Synthesis and the Biological Activities of (±)-Norannuradhapurine

by Surachai Nimgirawath, Rujee Lorpitthaya, Asawin Wanbanjob, Thongchai Taechowisan and Yue-Mao Shen

Molecules 2009, 14(1), 89-101; https://doi.org/10.3390/molecules14010089 - 29 Dec 2008

Cited by 8 | Viewed by 11691

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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13 pages, 136 KiB

Open AccessArticle

Total Synthesis and Antimicrobial Activity of (±)-Laurelliptinhexadecan-1-one and (±)-Laurelliptinoctadecan-1-one

by Surachai Nimgirawath, Phansuang Udomputtimekakul, Samathi Pongphuttichai, Asawin Wanbanjob and Thongchai Taechowisan

Molecules 2008, 13(12), 2935-2947; https://doi.org/10.3390/molecules13122935 - 28 Nov 2008

Cited by 3 | Viewed by 9366

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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