Show simple item record

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

Files in this item


There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record