A Bioassay Using the Human Hepatoblastoma Cell Line HepG2 for Detecting Phototoxicity of Furocoumarins

Colombain, Michel; Goll, Valérie; Muyard, Frédéric; Girard, Christian; Bévalot, Françoise; Richert, Lysiane

doi:10.1055/s-2001-17364

Cited by 20 publications

(13 citation statements)

References 2 publications

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“…When tested as an anti-inflammatory agent it exerted a remarkable inhibitory activity on lipopolysaccharide-induced production of prostaglandin E 2 in rat peritoneal macrophages [44], and showed a significant effect on 5-lipoxygenase [62]. As it was shown to be phototoxic [103][104], imperatorin might be used for the treatment of skin diseases such as psoriasis, mycoses and vitiligo, although this therapeutic potential has not been assessed until now.…”

Section: Isopentenyloxy-furocoumarinsmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

272

170

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Prenyloxycoumarins and prenyloxyfuranocoumarins (isopentenyloxy-, geranyloxy-, linear and cyclic sesquiterpenyloxy compounds and their biosynthetic derivatives) represent a family of secondary metabolites that have been considered for years just as intermediates of other coumarin-based compounds. Only in the last two decades these secondary metabolites have been recognized as interesting and valuable biologically active natural products. Up to now more than 160 compounds have been isolated from plants mainly belonging to the families of Rutaceae and Umbelliferae, comprising common edible vegetables and fruits like lemons, oranges and grapefruits. In view of the biological activity of some natural prenyloxycoumarins, very recently syntheses of structurally related analogs aimed to establish detailed structure-activity relationships have also been carried out. Many of the isolated prenyloxy- and prenyloxy-furanocoumarins and their semisynthetic derivatives were shown to exert in vitro and in vivo remarkable anti-tumoral, anti-inflammatory and anti-viral effects. The object of this review is to examine in detail the different types of prenyloxycoumarins and prenyloxyfuranocoumarins from the chemical, phytochemical and biological point of view.

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Section: Isopentenyloxy-furocoumarinsmentioning

confidence: 99%

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Curini¹,

Cravotto²,

Epifano³

et al. 2006

CMC

272

170

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“…Briefly, the test tumor cells in exponential growth were plated at a final concentration of 2.5 Â 10 3 cells/well in 96-well tissue culture dishes for 24 h. The cells were then treated with compounds at varying concentrations. To exclude phototoxicity [33], the operation process was kept away from bright light, and the cells were incubated in a dark incubator. After 48 h, the cells were incubated in fresh cell culture medium and washed carefully [34].…”

Section: Experimental Partmentioning

confidence: 99%

Triterpenoids and Iridoid Glycosides from Gentiana dahurica

Zang

Zhang

et al. 2010

Helvetica Chimica Acta

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One new and six known pentacyclic triterpenoids, 1 and 4 -9, resp., along with two new and three known iridoid glycosides, 2 and 3, and 10 -12, resp., were isolated from the roots of Gentiana dahurica (Qin-Jiao). The new structures were elucidated by means of spectroscopic and chemical methods as 1b,2a,3a,24-tetrahydroxyursa-12,20(30)-dien-28-oic acid (1), 6'-O-acetylgentiopicroside (2), and 3'-acetylgentiopicroside (3). Isolated compounds were tested for their cytotoxicity against the MCF-7 human breast cancer cell line using the MTT assay. Among them, triterpenoids 2a,3b,24-trihydroxyurs-12-en-28-oic acid (6) and 3b,24-dihydroxyurs-12-en-28-oic acid (9) were found to have moderate cytotoxic effects with IC 50 values of 20.9 and 21.7 mg/ml, respectively. Additionally, the chemotaxonomic significance of the identified secondary metabolites is briefly discussed.

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“…The presence of this furocoumarin could be considered as chemotaxonomically significant in all these Apiaceae genera [2][3][4]. Peucedanin was previously found to be cytotoxic to Ehrlich's tumor cells and human carcinoma cell line HepG2 [5], and to have Ca 2+ channel blocking activity [6]. In our previous study, peucedanin showed its therapeutic potential in experiments using HeLa cells [7] presenting induction of early stages of apoptosis in tests with Annexine V, and also increased levels of anti-apoptotic heat shock proteins (Hsp) Hsp 27 and Hsp 72, which may be important from the potential anticancer properties of this furanocoumarin [7,8].…”

mentioning

confidence: 99%

Single Crystal X-ray Diffraction, Spectroscopic and Mass Spectrometric Studies of Furanocoumarin Peucedanin

Bartnik

Arczewska

Hoser

et al. 2014

Natural Product Communications

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The structure of peucedanin, isolated from Peucedanum tauricum Bieb. (Apiaceae), has been established using single crystal X-ray diffraction. This furanocoumarin isolated from the light petroleum extract of P. tauricum fruits was characterized by high resolution EI-MS, sATR-FTIR and 2D NMR spectroscopic techniques. The EI-MS showed the typical fragmentation pattern of methoxyfuranocoumarins. Extensive 1D (1 H and 13 C) as well as 2D NMR data enabled complete assignment of the carbon atoms in the peucedanin molecule. The FTIR data confirms intermolecular hydrogen bonding between peucedanin molecules in polar solvents. Peucedanin crystallises in the R-3 space group from the trigonal system with one molecule in the asymmetric part of the unit cell. The crystal lattice of peucedanin consists of the molecules arranged in separate columns. They are related by two fold screw axes and centres of symmetry. Interestingly, peucedanin columns form two channels per unit cell with a diameter of 7.5Å going through the crystal lattice in the Z-direction. These channels are filled with disordered water molecules, which are surrounded by hydrophobic methyl groups and are located exactly at the centres of the channels. The peucedanin molecules are stacked in a single column with the opposite orientation of the neighbouring molecules. These results could be interesting in further application of this molecule, for example in biological tests of its activity.

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A Bioassay Using the Human Hepatoblastoma Cell Line HepG2 for Detecting Phototoxicity of Furocoumarins

Cited by 20 publications

References 2 publications

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Chemistry and Biological Activity of Natural and Synthetic Prenyloxycoumarins †

Triterpenoids and Iridoid Glycosides from Gentiana dahurica

Single Crystal X-ray Diffraction, Spectroscopic and Mass Spectrometric Studies of Furanocoumarin Peucedanin

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