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There is some evidence that non-photoactivated psoralens may be active against breast and colon tumor cells. Therefore, we evaluated the antiproliferative, proapoptotic, and anti-migrative effect of 5-methoxypsoralen (5-MOP) isolated from Peucedanum tauricum MB fruits in human colorectal adenocarcinoma (HT-29 and SW620), osteosarcoma (Saos-2 and HOS), and multiple myeloma (RPMI8226 and U266). Dose- and cell-line-dependent effects of 5-MOP on viability and proliferation were observed, with the strongest inhibitory effect against Saos-2 and a moderate effect against the HOS, HT-29, and SW620 cells. Multiple myeloma showed low sensitivity. The high viability of human normal cell cultures (HSF and hFOB) in a wide range of 5-MOP concentrations tested (6.25–100 µM) was confirmed. Moreover, the migration of treated Saos-2, SW620, and HT-29 cell lines was impaired, as indicated via a wound healing assay. Flow cytometry analysis conducted on Saos-2 cells revealed the ability of 5-MOP to block the cell cycle in the G2 phase and trigger apoptosis, which was accompanied by a loss of mitochondrial membrane potential, caspases (-9 and -3) activation, the altered expression of the Bax and Bcl-2 proteins, and decreased AKT phosphorylation. This is the first report evaluating the antiproliferative and antimigratory impact of non-UV-activated bergapten on the abovementioned (except for HT-29) tumor cells, which provides new data on the potential role of 5-MOP in inhibiting the growth of various types of therapeutic-resistant cancers.

Pure methoxyfuranocoumarins were isolated from a crude petroleum ether extract (CPE; Soxleth extraction efficiency 12.28%) from fruits of Peucedanum tauricum MB. (Apiaceae) by counter-current chromatography in a hydrostatic equilibrium system (centrifugal partition chromatography—CPC). The optimized biphasic solvent system composed of n-heptane-ethyl acetate-methanol-water (5:2:5:2; v/v/v/v) in the ascending mode of elution was used (3 mL/min, 1600 rpm). In the single run, peucedanin (P), 8-methoxypeucedanin (8MP), and bergapten (5MOP) were obtained as pure as 95.6%, 98.1%, and c.a. 100%, respectively. The carefully optimized and developed CPC was effectively transferred from the analytical to the semi-preparative scale (where 20 mg and 150 mg of CPE were loaded, respectively). Identification and quantitative analysis of methoxyfuranocoumarins was carried out in the plant material, in the CPE, and in individual CPC fractions by use of validated high-performance liquid chromatography with diode array detection and mass spectrometry (HPLC-DAD-ESI-MS). For the separation steps, the extraction/isolation recovery was calculated. In this case, CPC proved to be an effective tool for the simultaneous isolation and separation of P, 8MP, and 5MOP from a multicomponent plant matrix, without additional pre-purification steps. The high purity of the obtained plant metabolites makes it possible to consider their use in pharmacological or biological studies.

Flavonoid glycosides from the aerial parts (leaves, flowers, and fruits) of Peucedanum tauricum Bieb. (Apiaceae) have been analyzed by thin-layer chromatography (TLC) with densitometry and by reversed-phase high-performance liquid chromatography (RP-HPLC) with diode-array detection (DAD). Solid-phase extraction (SPE) was used to isolate the flavonoid fraction from methanolic extracts of different parts of the plant. TLC separation of the compounds was performed on silica gel plates with two different mobile phases, ethyl acetate–methyl ethyl ketone—formic acid—water, 5 + 3 + 1 + 1 (v/v), and ethyl acetate—formic acid—water, 9 + 1 + 1 (v/v). HPLC separation was performed on a C18 analytical column (250 mm × 4 mm i.d., 5-μm particles) with 45% methanol in water containing 1% (v/v) acetic acid as mobile phase. Rutoside, isoquercitrin, isorhamnetin-3-glycoside, isorhamnetin-3-rutinoside, and quercetin, as the free aglycone, were detected and identified in the extracts. All the compounds investigated had flavonol-like structures and are chemotaxonomically important in plants of the genus Peucedanum. This is the first time isoquercitrin and isorhamnetin-3-glucoside have been identified in Peucedanum tauricum Bieb. The fruits of this plant have also been investigated for the presence of flavonoids, for the first time.

SummaryTwo-dimensional planar chromatography (2D TLC) on cellulose layers, solid phase extraction (SPE), and reversed-phase high-performance liquid chromatography (HPLC) have been used for purification, separation, and identification of the phenolic acids in the foliage and fruits of Peucedanum tauricum Bieb. (Umbelliferae = Apiaceae). Methanolic extracts of the foliage and fruit were purified and the free phenolic acids fractions were isolated by means of the classical method of Ibrahim and Towers. Hydrolysis of the esters and glycosides was performed by the method of Schmidtlein and Herrmann. Isolated fractions containing phenolic acids were investigated by comparison with standards, by means of analytical 2D TLC on cellulose layers, by use of derivatization reagents (gaseous NH3, 3% FeCl3 and diazotized sulfanilic acid in 20% sodium carbonate solution), and by RP HPLC with isocratic elution (mobile phase methanol—water, 20:80 (v/v) containing 1% (v/v) acetic acid) and UV spectroscopy (by means of the diode-array detector of the liquid chromatograph).By use of this procedure the cinnamic acid derivatives caffeic acid, pcoumaric acid, and ferulic acid, the benzoic acid derivatives vanillic acid, p-hydroxybenzoic acid, protocatechuic acid, gentisic acid, and syringic acid, and the depside chlorogenic acid were detected and identified in the foliage of Peucedanum tauricum Bieb. Caffeic, p-coumaric, vanillic, p-hydroxybenzoic, protocatechuic, and syringic acids were also detected and identified in the fruit of the plant. This is the first time these phenolic acids have been isolated, detected, and identified in the foliage and fruit of P. tauricum Bieb.

SummaryColumn chromatography and normal- and reversed-phase TLC have been used for the purification, separation, and isolation of coumarins from the fruits of Peucedanum tauricum Bieb. (Umbelliferae = Apiaceae). Preliminary purification of the coumarin sediment obtained from a petroleum ether extract was performed by preparative column chromatography on silica gel with a gradient of ethyl acetate in dichloromethane as mobile phase, and by preparative reversed-phase thin-layer chromatography with 90% aqueous MeOH as mobile phase. Preparative normal-phase TLC with cyclohexane and ethyl acetate as mobile phase, then re-chromatography with more selective mobile phase mixtures of ethyl acetate, dichloromethane, n-heptane, and acetonitrile enabled isolation of four crystalline coumarins (A-D). All the steps of these procedures were monitored by analytical TLC (with detection by UV illumination at λ = 366 nm and densitometric scanning at λ = 320 nm). Isolated crystalline coumarins were identified by comparison with standards in analytical TLC and in RPHPLC with gradient elution, and by melting point (m.p.) measurement and UV spectroscopy. Two were identified as isoimperatorin (A), and bergapten (C); this is the first time these compounds have been isolated from P. tauricum Bieb.