Non-Alkaloidal Compounds from the Bulbs of the Egyptian Plant Pancratium maritimum

Abstract

Phytochemical investigation of the cytotoxic fractions of fresh bulbs of Pancratium maritimum L. led to the isolation and structure identification of two new compounds, pancricin (1) and pancrichromone (4), together with four known compounds, including 2,4-dihydroxy-6- methoxy-3-methyl acetophenone (2), 5-formylfurfuryl acetate (3), 7-β-D-glucosyloxy-5-hydroxy-2- methylchromone (5), and ethyl-b-D-glucopyranoside (6). Their structures were established on the basis of 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC, and HMBC), as well as HR mass spectral analyses. The compounds were evaluated for their antimigratory and antiproliferative activities against the highly metastatic human prostate cancer cell line (PC-3M). Compound 5 was the most active compound displaying good activity in the proliferation assay comparable to that of the positive control 4-hydroxyphenylmethylene hydantoin, while it displayed only weak antimigratory activity compared to the positive control 4-ethylmercaptophenylmethylene hydantoin.

Naturally Occurring Chromone Glycosides: Sources, Bioactivities, and Spectroscopic Features

“…Scindapsus officinalis stems [31] Ammi visnaga fruits [32] Knoxia corymbosa [33] Pancratium biflorum roots [34] Panacratium biflorum flowering bulbs [35] Pancratium maritimum L. fresh bulbs [36] Peucedanum austriacum [37] Tecomella undulata bark [38] Adina rubescens leaves [39] Dryopteris fragrans [40] Staphylea bumalda leaves [20] Immunomodulatory activity inhibited the proliferation of murine B lymphocytes in vitro at 10 Hypericum henryi aerial parts [41] Hypericum erectum [42] No reported biological activity Hyperimone A Urachromone B Hypericum henryi aerial parts [41] No reported biological activity…”

“…The scale-insect pathogenic fungus Orbiocrella sp. [23] No reported biological activity Lobodirin Lobodirina cerebriformis lichen [51] No reported biological activity Galapagin Lichens (Roccellaria mollis, Schismatomma accedens, Roccella galapagoensis) [51] No reported biological activity Uncinoside A (5-hydroxy-2,6,8trimethylchromone 7-O-β-D-glucopyranoside) Selaginella uncinate Herb [24] Antiviral activity against respiratory syncytial virus (RSV) with an IC 50 value of 6.9 µg/mL, against parainfluenza type 3 virus (PIV 3) with an IC 50 value of 13.8 µg/mL [24] Pancrichromone Pancratium maritimum L. fresh bulbs [36] No reported biological activity Uncinoside B ( [53] Rumex gmelini Turcz. roots [54] Anti-oxidant activity (DPPH radical scavenging capacity with an IC 50 value of 66.9 ± 1.3 µM) [53] 5-acetonyl-7-β-D-glucopyranosyl-…”

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

“…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 ].…”

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

“…On the contrary, the non-alkaloidal constituents of Amaryllidaceae plants have been overlooked by researchers. However, since the identification of chromones, chromones, acetophenones, and their glycosides from Pancratium biflorum [20][21][22], several studies were carried out to explore the non-alkaloidal constituents of the genus Pancratium [23][24][25], resulting in identification of different chromones and acetophenones and their glycosides, flavonoids, chalcones, and others [20][21][22][23][24][25].…”