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AuthorAlali, Feras
AuthorEl-Elimat, Tamam
AuthorAlbataineh, Hanan
AuthorAl-Balas, Qosay
AuthorAl-Gharaibeh, Mohammad
AuthorFalkinham, III, Joseph O.
AuthorChen, Wei-Lun
AuthorSwanson, Steven M.
AuthorOberlies, Nicholas H.
Available date2016-11-10T06:53:36Z
Publication Date2015-07-06
Publication NameJournal of Natural Productsen_US
CitationAlali F, El-Elimat T, Albataineh H, et al. Cytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii. Journal of natural products. 2015;78(7):1708-1715.
AbstractEight 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.
SponsorDeanship of Research, Jordan University of Science and Technology, Irbid, Jordan, and via program project grant P01 CA125066 from the National Cancer Institute/National Institutes of Health, Bethesda, MD, USA.
PublisherAmerican Chemical Society
SubjectHT29 cells
SubjectInhibitory Concentration 50
SubjectMicrobial Sensitivity Tests
SubjectMolecular Structure
SubjectStructure-Activity Relationship
TitleCytotoxic Homoisoflavones from the Bulbs of Bellevalia eigii
Issue Number7
Volume Number78
dc.identifier.essn 1520-6025

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