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.
Highlights
The Amaryllidaceae family consist of about 85 genera and 1100 species; they are well known for their ornamental values and biologically-active alkaloids [1]
Pancratium includes about 15 species, distributed throughout the Mediterranean, Africa, and Asia, only three species of this genus, P. maximum, P. sickenbergeri, and P. tortuosum, are indigenous to Saudi Arabia [3]
The 1H Plants 2022, 11, x FOR PEER REVIEWand 13C NMR data of 1 (Table 1) showed signals for 1,4-disubstituted benzene m3 ooife1t4y linked to Z-propenoic acid methyl ester and O-β-glucopyranoside units
Summary
The Amaryllidaceae family consist of about 85 genera and 1100 species; they are well known for their ornamental values and biologically-active alkaloids [1]. Pancratium includes about 15 species, distributed throughout the Mediterranean, Africa, and Asia, only three species of this genus, P. maximum, P. sickenbergeri, and P. tortuosum, are indigenous to Saudi Arabia [3]. In Egypt, there are four species belonging to the genus Pancratium, namely P. arabicum, P. maritimum L., P. sickenbergeri, and P. tortuosum [4]. The extracts of the bulbs and flowers of P. maritimum possess analgesic, antifungal, and anticancer activities. These extracts possess purgative, hypotensive, emetic, and anti-inflammatory effects [5]
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