Cytotoxic homoisoflavonoids from the bulbs of Bellevalia flexuosa
作者： Tamam El-Elimat , José Rivera-Chávez , Joanna E. Burdette , Austin Czarnecki , Maram B. Alhawarri
DOI: 10.1016/J.FITOTE.2018.02.022
关键词: Bellevalia flexuosa 、 Bellevalia 、 Absolute configuration 、 Chemistry 、 Stereochemistry 、 Cytotoxicity 、 Chloroform 、 Cytotoxic T cell 、 IC50 、 Cell culture
摘要: Abstract Four new homoisoflavonoids, 7-O-methyl-8-demethoxy-3′-hydroxy-3,9-dihydropunctatin (4), 6-hydroxy-8-demethoxy-4′-O-methyl-3,9-dihydropunctatin (8), 7,4′-O-dimethyl-8-demethoxy-3,3′-dihydroxy-3,9-dihydropunctatin (13), and 7-O-methyl-3-hyroxy-3,9-dihydropunctatin (14) were identified from a chloroform extract of the bulbs Bellevalia flexuosa, along with 13 known analogues. The structures determined by analysis HRMS NMR data, while ECD spectroscopy enabled assignment absolute configurations compounds 4, 8, 16. cytotoxic activities isolated (1–17) evaluated using panel human cancer cell lines. Compounds 2 7 most potent against MDA-MB-435 (melanoma) line IC50 values 1.6 2.0 μM, respectively, essentially equipotent OVCAR3 (ovarian) 9.5 10.8 μM, respectively. However, compound 7, an value 3.6 μM, was MDA-MB-231 (breast) line.
qu.edu.qa参考文章(16)
W. Heller, Ch. Tamm, Homoisoflavanones and Biogenetically Related Compounds Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. ,vol. 12, pp. 105- 152 ,(1981) , 10.1007/978-3-7091-8611-4_3
María Isabel Calvo, Three new homoisoflavanones from the bulbs of Ledebouria floribunda. Fitoterapia. ,vol. 80, pp. 394- 398 ,(2009) , 10.1016/J.FITOTE.2009.05.010
Matteo Adinolfi, Gaspare Barone, Maria Michela Corsaro, Lorenzo Mangoni, Rosa Lanzetta, Michelangelo Parrilli, Absolute configuration of homoisoflavanones from muscari species Tetrahedron. ,vol. 44, pp. 4981- 4988 ,(1988) , 10.1016/S0040-4020(01)86202-5
James M. Rae, Chad J. Creighton, Jeanne M. Meck, Bassem R. Haddad, Michael D. Johnson, MDA-MB-435 cells are derived from M14 melanoma cells--a loss for breast cancer, but a boon for melanoma research. Breast Cancer Research and Treatment. ,vol. 104, pp. 13- 19 ,(2007) , 10.1007/S10549-006-9392-8
Feras Q. Alali, Ahmad Gharaibeh, Abdullah Ghawanmeh, Khaled Tawaha, Nicholas H. Oberlies, Colchicinoids from Colchicum crocifolium Boiss.: a case study in dereplication strategies for (-)-colchicine and related analogues using LC-MS and LC-PDA techniques. Phytochemical Analysis. ,vol. 19, pp. 385- 394 ,(2008) , 10.1002/PCA.1060
Tamam El-Elimat, Huzefa A Raja, Mario Figueroa, Steven M Swanson, Joseph O Falkinham III, David M Lucas, Michael R Grever, Mansukh C Wani, Cedric J Pearce, Nicholas H Oberlies, Sorbicillinoid analogs with cytotoxic and selective anti-Aspergillus activities from Scytalidium album The Journal of Antibiotics. ,vol. 68, pp. 191- 196 ,(2015) , 10.1038/JA.2014.125
Feras Q. Alali, Chiraz Soumia M. Amrine, Tamam El-Elimat, Ahmad Alkofahi, Khaled Tawaha, Mohammad Gharaibah, Steven M. Swanson, Joseph O. Falkinham, Marisa Cabeza, Araceli Sánchez, Mario Figueroa, Nicholas H. Oberlies, Bioactive Withanolides from Withania obtusifolia Phytochemistry Letters. ,vol. 9, pp. 96- 101 ,(2014) , 10.1016/J.PHYTOL.2014.05.002
Xiaoling Zhou, Zhang Yuping, Huading Zhao, Junsheng Liang, Yi Zhang, Shuyun Shi, Antioxidant homoisoflavonoids from Polygonatum odoratum. Food Chemistry. ,vol. 186, pp. 63- 68 ,(2015) , 10.1016/J.FOODCHEM.2015.02.058
Dulcie A. Mulholland, Sianne L. Schwikkard, Neil R. Crouch, The chemistry and biological activity of the Hyacinthaceae Natural Product Reports. ,vol. 30, pp. 1165- 1210 ,(2013) , 10.1039/C3NP70008A
Matteo Adinolfi, Gaspare Barone, Margherita Belardini, Rosa Lanzetta, Guglielmo Laonigro, Michelangelo Parrilli, Homoisoflavanones from Muscari comosum bulbs Phytochemistry. ,vol. 24, pp. 2423- 2426 ,(1985) , 10.1016/S0031-9422(00)83055-1