New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.

Medicinal Chemistry and Pharmacognosy Department, Faculty of Pharmacy, Jordan University of Science and Technology, P.O. Box 3030, Irbid 22110, Jordan. falali@just.edu.jo

Journal of natural products 2005 Feb

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As part of our continuing investigation of Jordanian Colchicum species, the biologically active components of Colchicum brachyphyllum were pursued. Using bioactivity-directed fractionation, nine colchicinoids were isolated and characterized. One of these has a novel ring system, to which we have ascribed the trivial name (+)-demecolcinone (9), and it represents the first naturally occurring dextrorotatory colchicinoid. Another isolated compound was a new colchicinoid analogue, (-)-2,3-didemethyldemecolcine (8), while the remaining seven known colchicinoids were new to the species: (-)-colchicine (1), (-)-3-demethylcolchicine (2), (-)-cornigerine (3), beta-lumicolchicine (4), (-)-androbiphenyline (5), (-)-demecolcine (6), and (-)-3-demethyldemecolcine (7). The brine shrimp lethality test was used to direct the isolation of these colchicinoids. Moreover, all pure compounds were evaluated for cytotoxicity against a human cancer cell panel, for antimicrobial activity in an array of bacteria and fungi (including yeast), and for their potential to be allosteric modulators of the gamma-aminobutyric acid type A receptor.

Citation

Feras Q Alali, Tamam El-Elimat, Chen Li, Amjad Qandil, Ahmad Alkofahi, Khaled Tawaha, Jason P Burgess, Yuka Nakanishi, David J Kroll, Hernán A Navarro, Joseph O Falkinham, Mansukh C Wani, Nicholas H Oberlies. New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid. Journal of natural products. 2005 Feb;68(2):173-8