title: 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). The known ferulic acid-derived acrylamide (17) and the new methylthioacrylate bellegimycin (18) are also reported. 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.
authors.affiliation: †Faculty of Pharmacy, Qatar University, Doha 2713, Qatar.
authors.forename: Feras
authors.initials: F
authors.lastname: Alali
authors.forename: Tamam
authors.initials: T
authors.lastname: El-Elimat
authors.forename: Hanan
authors.initials: H
authors.lastname: Albataineh
authors.forename: Qosay
authors.initials: Q
authors.lastname: Al-Balas
authors.affiliation: ⊥Institut für Geobotanik und Botanischer Garten, Martin-Luther-Universität, Am Kirchtor 1, 06108 Halle, Germany.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Al-Gharaibeh
authors.affiliation: ∥Department of Biological Sciences, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, United States.
authors.forename: Joseph O
authors.initials: JO
authors.lastname: Falkinham
authors.affiliation: ∇Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States.
authors.forename: Wei-Lun
authors.initials: WL
authors.lastname: Chen
authors.affiliation: ∇Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States.
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.affiliation: #Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina 27402, United States.
authors.forename: Nicholas H
authors.initials: NH
authors.lastname: Oberlies
mesh_terms: D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007597:Jordan; D019668:Liliaceae / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects; D020102:Mycobacterium smegmatis / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014747:Vinblastine / Q000494:pharmacology
chemical_list: D007529:Isoflavones; D014747:Vinblastine