Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii

Abstract

Eight new and 10 known compounds, were isolated from an organic extract of the bulbs of Bellevalia eigii as part of a search for anticancer leads from native plants of Jordan. Of these, the series of 16 homoisoflavonoids (1-16), comprise the seven new analogues 7-O-methyl-3′-hydroxy-3,9-dihydropunctatin (3), 6-hydroxy-7-O-methyl-3,9-dihydropunctatin (6), 7,4′-di-O-methyl-3′-hydroxy-3,9-dihydropunctatin (9), 7-O-methylpunctatin (10), 7-O-methyl-3′-hydroxypunctatin (13), 5-hydroxy-7,8-dimethoxychroman-4-one (14), and 7-O-methyl-8-demethoxy-3-hydroxy-3,9-dihydropunctatin (15), as well as the known ferulic acid-derived acrylamide (17), and the new methylthioacrylate bellegimycin (18). The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 1–9, 15, and 16 were determined using ECD spectroscopy, while a modified Mosher’s ester method was used for compound 18. Optical rotation data for the known compounds 1, 2, and 8 are reported here for the first time. The cytotoxic activities of all compounds were evaluated using the MDA-MB-435 (melanoma) and HT-29 (colon) cancer cell lines. Compounds 4 and 9 were the most potent on the latter cell line with IC50 values of 1.0 and 1.1 μM, respectively. Compounds 1-18 were assessed for antimicrobial activity using a collection of bacteria and fungi; compounds 4 and 12 showed promising activity against the bacterium Mycobacterium smegmatis with MIC values of 17 and 24 μg/mL, respectively.

Design, synthesis, biological evaluation, and molecular dynamics of novel cholinesterase inhibitors as anti‐Alzheimer's agents

“…The structures of all the newly synthesized compounds were characterized by IR, 1 H NMR, 13 C NMR spectroscopies, and CHN analyses. It is well‐known that the geometry of compounds is affected by thermodynamically controlled reactions . So at room temperature and even by rising temperature up to 80°C, E isomer is obtained, while in the presence of hυ irradiation conditions, Z isomer is formed.…”

“…So at room temperature and even by rising temperature up to 80°C, E isomer is obtained, while in the presence of hυ irradiation conditions, Z isomer is formed. Therefore, the molecular configuration of all of the compounds that have been obtained at room temperature is assigned as E configuration …”

New Formyl Phloroglucinol Meroterpenoids from the Leaves of Eucalyptus robusta

“…The ROESY correlations of H-5/H-8 β , H-7/H-8 α , Me-12/H-5, Me-15/H-6, and H-6/H-1 indicated the α -orientations of H-1, H-6, and H-7 and the β -orientations of H-4 and H-5. The absolute configuration was determined by application of the Snatzke’s helicity rule1013141516. The P/M -helicity of the dihydropyran ring in FPMs controlled the signs of Cotton effects approximately between 270–310 nm (Fig.…”

Cytotoxic Homoisoflavonoids from <i>Ophiopogon japonicus</i> Tubers

“…The cytotoxic effect of homoisoflavonoids has been indicated elsewhere, 12) and the structureactivity relationship has been investigated. 13) Accordingly, the 2′-hydroxy and 4′-methoxy groups seem to have a contribution to the activity. In our study, compounds 1, 2, and 3 possessing 2′-hydroxy and 4′-methoxy substituent showed positive effect on at least one cancer cell line.…”