1. Academic Validation
  2. Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii

Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii

  • J Nat Prod. 2015 Jul 24;78(7):1708-15. doi: 10.1021/acs.jnatprod.5b00357.
Feras Alali 1 Tamam El-Elimat Hanan Albataineh Qosay Al-Balas Mohammad Al-Gharaibeh 2 Joseph O Falkinham 3rd 3 Wei-Lun Chen 4 Steven M Swanson 4 Nicholas H Oberlies 5
Affiliations

Affiliations

  • 1 †Faculty of Pharmacy, Qatar University, Doha 2713, Qatar.
  • 2 ⊥Institut für Geobotanik und Botanischer Garten, Martin-Luther-Universität, Am Kirchtor 1, 06108 Halle, Germany.
  • 3 ∥Department of Biological Sciences, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, United States.
  • 4 ∇Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States.
  • 5 #Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, Greensboro, North Carolina 27402, United States.
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.

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