An Efficient Total Synthesis of (±)-Galanthamine

Guillou, Catherine; Beunard, Jean‐Luc; Gras, Emmanuel; Thal, C.

doi:10.1002/1521-3773(20011217)40:24<4745::aid-anie4745>3.0.co;2-5

Cited by 78 publications

(40 citation statements)

References 26 publications

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“…Since Overman's approach to (7)-tazettine (62) using an intramolecular Heck reaction (225), this methodology for the construction of the critical quaternary stereogenic center has been imple mented for the preparation of many alkaloids. An efficient total synthesis of racemic galanthamine (75) following this approach has been recently disclosed (227). An efficient total synthesis of racemic galanthamine (75) following this approach has been recently disclosed (227).…”

Section: B Organometallic-promoted Reactionsmentioning

confidence: 99%

Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

Bastida

Lavilla

Viladomat

2006

The Alkaloids: Chemistry and Biology

182

273

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Section: B Organometallic-promoted Reactionsmentioning

confidence: 99%

Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

Bastida

Lavilla

Viladomat

2006

The Alkaloids: Chemistry and Biology

182

273

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“…Galanthamine, an isoquinoline alkaloid, is obtained on a commercial scale for its pharmacological interest from Narcissus spp. and Leucojum aestivum as well as synthetically (Guillou et al, 2001;Marco-Contelles et al, 2006). Lycorine, a pyrrolophenanthridine alkaloid, displays a strong antiviral effect against poliovirus, measles and Herpes simplex type 1 viruses, as well as high antiretroviral (Szlávik et al, 2004) and strong antimitotic activities (Kukhanova et al, 1983).…”

Section: Introductionmentioning

confidence: 99%

New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures.

Tahchy

Boisbrun²,

Ptak³

et al. 2010

Acta Biochim Pol

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Biotransformation of deuterated-4'-O-methylnorbelladine into alkaloids galanthamine and lycorine in tissue cultures of Leucojum aestivum was demonstrated using HPLC coupled to mass spectrometry. GC-MS screening was also carried to investigate other native and deuterated alkaloids. A total of six labeled alkaloids were identified indicating that 4'-O-methyl-d(3)-norbelladine is incorporated into three different groups of Amaryllidaceae alkaloids that are biosynthesized by three modes of intramolecular oxidative phenol coupling.

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“…In some fractions even a small percentage of galanthamine, was observed. As mentioned above it increases ACh concentration in synapses of CNS [ 24 , 25 , 26 , 27 ]. The first published work on inhibition of AChE by galanthamine appeared thanks to Maskowski and Kruglikov-Lvov in 1951.…”

Section: Introductionmentioning

confidence: 99%

The Bioassay-Guided Fractionation and Identification of Potent Acetylcholinesterase Inhibitors from Narcissus c.v. ‘Hawera’ Using Optimized Vacuum Liquid Chromatography, High Resolution Mass Spectrometry and Bioautography

et al. 2020

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Bioassay-guided isolation of bioactive compound is a modern and efficient technique in metabolites screening. It may shorten the total time of the entire process and reduce some costs of it. The aim of this paper was to fractionate and isolate alkaloids by developing an innovative vacuum liquid chromatography method for a species of Narcissus c.v. ‘Hawera’ rarely investigated so far and establishing the inhibitory activity of acetylcholinesterase (AChE). The studies consisted of the extraction of plant material by modern pressurized liquid extraction (PLE), followed by the isolation of alkaloidal fractions. For this purpose, the pioneering gradient vacuum liquid chromatography (gVLC) technique was employed by using two sorbents in various proportions packed in polypropylene cartridges for the first time. This step was performed in order to pre-clean the samples but also to establish the best combination of sorbents which permits obtaining potentially strong AChE inhibitors. The collected fractions were examined by HPLC/ESI-QTOF-MS in order to compare which combination of sorbents would allow us to obtain the highest concentration of alkaloids. The combination of these techniques confirmed the presence of the alkaloids and enabled the development of a modern method for the fractionation and isolation of the compounds with strong anti-AChE activity.

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An Efficient Total Synthesis of (±)-Galanthamine

Cited by 78 publications

References 26 publications

Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

Chapter 3 Chemical and Biological Aspects of Narcissus Alkaloids

New method for the study of Amaryllidaceae alkaloid biosynthesis using biotransformation of deuterium-labeled precursor in tissue cultures.

The Bioassay-Guided Fractionation and Identification of Potent Acetylcholinesterase Inhibitors from Narcissus c.v. ‘Hawera’ Using Optimized Vacuum Liquid Chromatography, High Resolution Mass Spectrometry and Bioautography

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