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AuthorTamam, El-Elimat
AuthorAlhawarri, Maram B.
AuthorRivera-Chávez, José
AuthorBurdette, Joanna E.
AuthorCzarnecki, Austin
AuthorAl-Gharaibeh, Mohammad
AuthorAl Sharie, Ahmed H.
AuthorAlhusban, Ahmed
AuthorAlali, Feras Q.
AuthorOberlies, Nicholas H.
Available date2023-06-21T04:35:45Z
Publication Date2020-10-31
Publication NameFitoterapia
Identifierhttp://dx.doi.org/10.1016/j.fitote.2020.104706
ISSN0367326X
URIhttps://www.sciencedirect.com/science/article/pii/S0367326X20302884
URIhttp://hdl.handle.net/10576/44615
AbstractThirteen compounds were isolated from the methanolic extract of the leaves of Androcymbium palaestinum Baker (Colchicaceae). Of these, three were new, two were new natural products, and eight were known. The new isolated compounds were (+)-1-demethylandrocine (5), (−)-andropalaestine (8), and (+)-2-demethyl-β-lumicolchicone (10), while the new natural products were (+)-O-methylkreysigine-N-oxide (3) and (+)-O,O-dimethylautumnaline (9). Moreover, two known compounds are reported for the first time from this species, specifically (−)-colchicine (11) and (−)-3-demethyldemecolcine (13). The structures of the isolated compounds were elucidated using a series of spectroscopic and spectrometric techniques, principally HRESIMS, 1D-NMR (1H and 13C NMR) and 2D-NMR (COSY, edited-HSQC, and HMBC). ECD spectroscopy was used for assigning the absolute configurations of compounds 3, 5, and 10. The cytotoxic activities of the isolated compounds were evaluated using the MDA-MB-435 (melanoma), MDA-MB-231 (breast), and OVCAR3 (ovary) cancer cell lines. Compound 11 was the most potent against all tested cell lines, with IC50 values of 12, 95 and 23 nM, respectively.
SponsorThis research was supported, in part, by the Deanship of Research, Jordan University of Science and Technology, Irbid, Jordan (Grant No. 258/2017) and the National Cancer Institute/National Institutes of Health, Bethesda, MD, USA via P01 CA125066. We thank Dr. L. Flores Bocanegra, J. M. Gallagher, Z. Y. Al Subeh, and Dr. N. D. Paguigan from UNCG for technical help and valuable suggestions. This work was performed in part at the Joint School of Nanoscience and Nanoengineering, a member of the Southeastern Nanotechnology Infrastructure Corridor (SENIC) and National Nanotechnology Coordinated Infrastructure (NNCI), which is supported by the National Science Foundation (Grant ECCS-1542174).
Languageen
PublisherElsevier
SubjectAlkaloids
Androcymbium
Leaves
Absolute configuration
Cytotoxicity
Human cancer cell lines
TitlePhenethyisoquinoline alkaloids from the leaves of Androcymbium palaestinum
TypeArticle
Volume Number146
dc.accessType Open Access


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