Cytotoxic Phenylpropanoid Derivatives and Alkaloids from the Flowers of Pancratium maritimum L.

Abstract

Regarding our growing interest in identifying biologically active leads from Amaryllidaceous plants, the flowers of Pancratium maritimum L. (Amaryllidaceae) were investigated. Purification of the cytotoxic fractions of the alcoholic extract of the flowers gave a new glycoside, 3-[4-(β-D-glucopyranosyloxy)phenyl]-2-(Z)-propenoic acid methyl ester (1), together with the previously reported compounds 3-methoxy-4-(β-D-glucopyranosyloxy)benzoic acid methyl ester (2), 3-(4-methoxyphenyl)propan-1-ol-1-O-β-D-glucopyranoside (3), (E)-3-(4-hydroxyphenyl)acrylic acid methyl ester (4), caffeic acid (5), dihydrocaffeic acid methyl ester (6), and pancratistatin (7). Interestingly, compounds 1 and 2 are phenolic-O-glycosides, while the glucose moiety in 3 is attached to the propanol side chain. This is the first report about the existence of 1–6 in the genus Pancratium. Further, glycosides 1–3 from the Amaryllidaceae family are reported on here for the first time. The structures of 1–7 were determined by analyses of their 1D (1H and 13C) and 2D (COSY, HMQC, HMBC) NMR spectra, and by high-resolution mass spectral measurements. Pancratistatin displayed potent and selective growth inhibitory effects against MDA-MB-231, HeLa, and HCT 116 cells with an IC50 value down to 0.058 µM, while it possessed lower selectivity towards the normal human dermal fibroblasts with IC50 of 6.6 µM.

Asperopiperazines A and B: Antimicrobial and Cytotoxic Dipeptides from a Tunicate-Derived Fungus Aspergillus sp. DY001

“…The evaluation of the antiproliferative and growth inhibitory effects of the compounds was carried out using MTT assay, as described before [ 45 , 46 , 47 , 48 ]. Briefly, the cells were incubated overnight in 5% CO 2 /air at 37 °C.…”

“…The evaluation of the antiproliferative and growth inhibitory effects of the compounds was carried out using MTT assay, as described before [45][46][47][48]. Briefly, the cells were incubated overnight in 5% CO 2 /air at 37 • C. The compounds were added at the top row of a 96-well microtiter plate, and descendant serial dilutions (1:4) of the concentration were carried out.…”

Chemical Characterization and Cytotoxic and Antioxidant Activity Evaluation of the Ethanol Extract from the Bulbs of Pancratium maritimun Collected in Sicily

“…Since then, several other studies have shown the occurrence of many alkaloids belonging to the lycorine-, lycorenine-, montaninetazettine-, galanthamine-, haemanthidine-, crinine-, isocarbostiryl-, narciclasine-, and pancratistatin groups, all biogenetically formed from norbelladines [ 8 ]. Alkaloids with these skeletons have been identified in plants, mainly bulbs, collected in Egypt [ 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 ], Bulgaria [ 17 ], Turkey [ 18 , 19 , 20 , 21 , 22 ], Tunisia [ 23 ], Portugal [ 24 ], Spain [ 25 , 26 ], and Italy (Calabria) [ 27 ]. The occurrence of the alkaloids in the bulbs of the different accessions is reported in Table 1 .…”

“…Apart from alkaloids, other metabolites have been identified in the bulbs or aerial parts of Pancratium maritimum L. ( P. maritimum) such as chromones, [ 30 , 31 , 32 ], flavonoids [ 30 , 31 , 33 ], phenylpropanoids [ 16 ], phenolic acids [ 33 , 34 ], and alginates [ 23 , 35 ].…”

Sternbergia Clusiana Bulb Ethanolic Extracts Induce Apoptosis in MCF-7 Breast Cancer Cells. (c2022)

“…In fact, the anti-proliferative impact of various species belonging to the Amaryllidaceae family was shown to be promising by a number of studies wherein the percentage of proliferation in cancer cells decreased with respect to time and concentration of plant extract used (Tayoub et al, 2018); (D. T. A. Youssef et al, 2022); (Silva et al, 2008). It is important to mention that the most prominent effect was detected with the highest dose after 48 h, revealing that therapeutic levels of proliferation inhibition are best reached after an incubation of 48 h. Nonetheless, the remaining experiments of this study were performed by incubating SbBEE for 24 h in aims of elucidating its mechanism of action and in order to detect earlier the induced apoptosis at a molecular level.…”