Biosynthetic Relationship Between Indole Alkaloids Produced by Cell Cultures of Ailanthus altissima

Crespi‐Perellino, N.; Guicciardi, A.; Malyszko, G.; Minghetti, A.

doi:10.1021/np50047a009

Cited by 29 publications

(9 citation statements)

References 7 publications

(15 reference statements)

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“…The biosynthesis of canthinone‐type alkaloids was, in part, demonstrated by the Guicciardi group by feeding experiments using cell cultures of Ailanthus altissima (Simaroubaceae) 12. A general biosynthetic pathway starting from tryptophan ( 5 ) is presented in Scheme .…”

Section: Introductionmentioning

confidence: 99%

Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin‐6‐one β‐Carboline Series and Study of Phenotypic Properties on C. elegans

et al. 2013

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Based on the biosynthetic line of canthin‐6‐one alkaloids from their simple precursors such as tryptamine, the present work is focused on the study of alternative protocol of the Bischler‐Napieralski reaction and has led to a full coverage of the different biosynthetic intermediates. Nanoparticles were also prepared as mimics of biosynthetic assembly lines and some interesting biological results in term of chemical ecology are also reported.

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Section: Introductionmentioning

confidence: 99%

Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin‐6‐one β‐Carboline Series and Study of Phenotypic Properties on C. elegans

et al. 2013

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“…In another route, the precursor i would undergo cyclization between the secondary amino and the carboxy carbonyl groups to give the key intermediate iv, which may be oxidized, leading to the formation of kumucarboline D (5). The cleavage of the N-4 -C-5 bond in iv would yield the 4,5-seco-β-carboline 6 [25,26].…”

Section: Resultsmentioning

confidence: 99%

Effects of Enantiomerically Pure β-Carboline Alkaloids from Picrasma quassioides on Human Hepatoma Cells

et al. 2019

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Four pairs of β-carboline enantiomers (1a/1b–4a/4b), 2 β-carboline derivatives (5 – 6) with a single enantiomeric configuration, together with 2 known achiral congeners (7 – 8) were isolated from the stems of Picrasma quassioides. Their structures were elucidated on the basis of extensive spectroscopic analyses and quantum mechanical calculations. Compound 5 possesses a 4,5-seco β-carboline framework and represents the first example of this type of β-carboline alkaloids from nature. A possible biosynthetic pathway is proposed to generate the racemate 4 and the enantiomerically pure compounds 5 and 6. All isolates were screened for their cytotoxicity against hepatocellular carcinoma Hep3B and HepG2 cells, which revealed that enantiomeric compounds 4a and 4b had distinctive effects in HepG2 cells. Further investigation showed that 4b could induce apoptosis in HepG2 cells.

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“…For compound 4, in addition to the comparison of chemical shifts described by Giesbrecht et al Giesbrecht, et al, [15] differential nuclear Overhauser enhancement (NOEDIFF) analysis allowed observation of an increase in H-4 alone when the hydrogens of the methoxyl group were irradiated, confirming the presence of the methoxyl group bound to N-3. The NMR data were compared with the literature data [15][16][17] and are available in the supporting information.…”

Section: Isolation and Identification Of Fluorescent Compoundsmentioning

confidence: 99%

Fluorescent Canthin‐6‐one Alkaloids from Simaba bahiensis: Isolation, Identification, and Cell‐Labeling Properties

et al. 2019

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Canthin‐6‐one alkaloids, which are present in plants of the genus Simaba, are natural compounds that are capable of acting as fluorescent probes. However, the chemical composition and fluorescent properties of most species of this genus have not been analyzed. The objective of this study was to characterize the fluorescent properties of an extract of S. bahiensis and identify the chemical entities responsible for these properties. In addition, the cell‐labeling properties of the fluorescent dye from A and of the isolated compounds were characterized by confocal fluorescence microscopy and flow cytometry. One quassinoid and three fluorescent alkaloids were isolated from S. bahiensis, all compounds were identified by using NMR spectroscopy and high‐resolution mass spectrometry. Staining experiments and HPLC‐FL analysis shown that canthin‐6‐one alkaloids are the main green fluorescent compounds in the analyzed dyes. All compounds evaluated showed a cytoplasmic marker with a residence time of 24 h. The present study is the first to describe the presence of canthin‐6‐one alkaloids in S. bahiensis, in addition to demonstrating promising cell‐labeling properties of fluorescent compounds from S. bahiensis with broad emission wavelengths.

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Biosynthetic Relationship Between Indole Alkaloids Produced by Cell Cultures of Ailanthus altissima

Cited by 29 publications

References 7 publications

Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin‐6‐one β‐Carboline Series and Study of Phenotypic Properties on C. elegans

Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin‐6‐one β‐Carboline Series and Study of Phenotypic Properties on C. elegans

Effects of Enantiomerically Pure β-Carboline Alkaloids from Picrasma quassioides on Human Hepatoma Cells

Fluorescent Canthin‐6‐one Alkaloids from Simaba bahiensis: Isolation, Identification, and Cell‐Labeling Properties

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