Antiprotozoal alkaloids from Galanthus trojanus

Kaya, Gulen Irem; Sarikaya, Buket Bozkurt; Önür, Mustafa; Somer, Nehir Unver; Viladomat, Françesc; Codina, Carles; Lauinger, Ina L.; Kaiser, Marcel; Taşdemir, Deniz

doi:10.1016/j.phytol.2011.05.008

Cited by 44 publications

(43 citation statements)

References 30 publications

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“…In the genus Galanthus, however, two new structural subgroups, graciline and plicamine type alkaloids, have been found (Ünver, 2007). The following new subgroups have also been reported: specific augustamine-type structures in Crinum kirkii (Machocho et al, 2004), a carboline alkaloid in Hippeastrum vittatum (Youssef, 2001), mesembrane (Sceletium)-type compounds in Narcissus pallidulus and N. triandrus (Bastida et al, 2006), and phtalideisoquinoline-, benzyltetrahydroisoquinoline-and aporphine-type alkaloids in G. trojanus (Kaya et al, 2004b(Kaya et al, , 2011. Mesembrane-type compounds are typical of the genus Sceletium of the Aizoaceae, while phtalideisoquinoline-, benzyltetrahydroisoquinoline-and aporphine-type alkaloids are found in the Papaveraceae, both families being dicotyledonous.…”

Section: Biosynthesis and Structural Types Of Amaryllidaceae Alkaloidsmentioning

confidence: 93%

“…Topoisomerase-interfering ability of these alkaloids partially correlated with cytostatic assays, using HeLa (cervix adenocarcinoma), MCF7 (breast adenocarcinoma) and A431 (skin epidermoid carcinoma) cells (Bozkurt et al, 2010). Arolycoricidine showed inhibitory activity against African trypanosomes, (Trypanosoma brucei rhodesiense) at micromolar levels (Kaya et al, 2011).…”

Section: Narciclasine-typementioning

confidence: 99%

“…This compound also possesses antimalarial activity against strains of chloroquine-sensitive Plasmodium falciparum, hypotensive effects and antiretroviral activity (Bastida et al, 2006;Kaya et al, 2011). Vittatine (24) and maritidine (30) have shown cytotoxic activity against HT29 colon adenocarcinoma, lung carcinoma and RXF393 renal cell carcinoma (Bastida et al, 2006;Silva et al, 2008).…”

Section: Haemanthamine Typementioning

confidence: 99%

See 2 more Smart Citations

The Genus Galanthus: A Source of Bioactive Compounds

Berkov¹,

Codina²,

Bastida³

2012

Phytochemicals - A Global Perspective of Their Role in Nutrition and Health

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Section: Biosynthesis and Structural Types Of Amaryllidaceae Alkaloidsmentioning

confidence: 93%

Section: Narciclasine-typementioning

confidence: 99%

Section: Haemanthamine Typementioning

confidence: 99%

See 1 more Smart Citation

The Genus Galanthus: A Source of Bioactive Compounds

Berkov¹,

Codina²,

Bastida³

2012

Phytochemicals - A Global Perspective of Their Role in Nutrition and Health

Self Cite

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“…Os métodos de arilação direta catalisada por sais de paládio aplicados à síntese de 1 tipicamente envolvem a reação de um haloareno (bromo e iodo derivados são Vol. 39,No. 3 os mais utilizados) para formar um intermediário organopaládio via adição oxidativa de Pd(0).…”

Section: Introductionunclassified

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Costa¹,

Silva²,

Lucas³

et al. 2016

Química Nova

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publicado na web em 18/02/2015 SYNTHESIS OF PHENANTHRIDINONE DERIVATIVES BY DIRECT ARYLATION. CHARACTERIZATION OF THE ABSORPTION AND EMISSION SPECTRA FOR REPRESENTATIVE EXAMPLES. The phenanthridinone heterocyclic system has attracted considerable attention in recent years due to the diverse array of physical, chemical and pharmacological properties demonstrated by natural and synthetic derivatives. As a consequence there has been considerable development of synthetic methodology for the synthesis of this and related heterocyclic ring systems. The synthetic literature is discussed and is compared with a direct arylation methodology for the intramolecular cyclization of tertiary (2-iodo)benzoylamides to generate the biaryl bond of these compounds. The efficient methodology allowed the synthesis of a number of previously unknown phenanthridinone products. The photoluminescent properties of representative examples were characterized and it is proposed that the previously unknown compound 1s reveals dual fluorescence in a manner similar to the known compound 1r.

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“…Plants of the Amaryllidaceae family, mainly those belonging to Galanthus, Leucojum, Narcissus, and Lycoris genera, are mostly used as extraction raw Correspondence: Dr. Agata Ptak (mfptak@cyf-kr.edu.pl), Department of Plant Breeding and Seed Science, Agricultural University, 31-140 Krakow, Poland Abbreviations: BAP, 6-benzylaminopurine; DW, dry weight; FW, fresh weight; MN, 4 -0-methylnorbelladine; NAA, α-naphthaleneacetic acid materials. A study of the biosynthetic pathway of galanthamine provided clues to the feasibility of the biotechnological production of this alkaloid [6][7][8][9] for which the organic total synthesis is low yielding and complex [10,11]. Studies aiming for the improvement of galanthamine and lycorine accumulation in in vitro cultures of Leucojum aestivum have been carried out in recent years.…”

Section: Introductionmentioning

confidence: 99%

4′‐O‐Methylnorbelladine feeding enhances galanthamine and lycorine production by Leucojum aestivum L. shoot cultures

Saliba

Ptak

Laurain-Mattar

2015

Engineering in Life Sciences

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Galanthamine and lycorine are Amaryllidaceae alkaloids that exhibit a wide range of pharmacological activities. Organic synthesis and plant extraction are the two main commercial sources of galanthamine. Since total organic synthesis is low yielding and complex, and the harvesting of plant biomass is causing wild plant depletion, in vitro cultures offer an alternative approach. Amaryllidaceae alkaloids can be regarded as derivatives of the common precursor 4′‐O‐methylnorbelladine via intramolecular oxidative phenol coupling. The aim of this work was to enhance the biosynthetic pathway of these alkaloids using in vitro techniques. The precursor 4′‐O‐methylnorbelladine was incorporated into the liquid medium of Leucojum aestivum shoot cultures at different concentrations (0, 0.05, 0.1, or 0.2 g/L). The cultures were conducted for various periods of time (15, 30, and 40 days). After alkaloid extraction and according to LC‐ESI‐MS analysis, the precursor highly stimulated the biosynthesis of both galanthamine (0.5 mg/g dry weight [DW], V/S 0.01 mg/g DW in the control sample, i.e. without precursor) and lycorine (0.2 mg/g DW, V/S 0.04 mg/g DW in the control sample) after its biotransformation by the shoot cultures. The optimal culture conditions for the production of both alkaloids were 0.1 g/L of precursor and 15 days of culture.

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Antiprotozoal alkaloids from Galanthus trojanus

Cited by 44 publications

References 30 publications

The Genus Galanthus: A Source of Bioactive Compounds

The Genus Galanthus: A Source of Bioactive Compounds

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

4′‐O‐Methylnorbelladine feeding enhances galanthamine and lycorine production by Leucojum aestivum L. shoot cultures

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